I came home pretty late; mom was watching TV, and Kim was in her room studying. I reported it to her and told her what Jenny made me do. I skipped the part where she said she'd fuck someone else; my ego couldn't handle it, and I knew Kim would have to allow it first anyway.

She told me we're going down to see mom, but I'm to excuse myself after ten minutes, and I have to go to my room. She came down first, and I came just moments after her. We chatted with mom a bit, and as I was told, I said I'm going to my room and left. I don't know what Kim's intentions were, so I sat on my bed and waited. Just like the last few nights, mom knocked and said "good night" to me, and then Kim came minutes later.

"Knees," she said as she entered the room, and I fell down like I was programmed. She collared me and sat down on my bed, crossing her legs.

"How did it feel?" she asked.

"What?" I asked back, as her question was unspecified.

"Fucking my girlfriend," she specified now, using a possessive pronoun that indicated I had no right to do it.

"It was weird, but ok." 

"Just ok?"

"I didn't get any physical satisfaction, but for a moment I felt like a man again," I answered, after taking a moment to get my thoughts straight.

"You do realize I fucked her the same way you did, and it still didn't make me a man?" She said it with a grin, wiping away that small satisfaction I got from it. I just looked down.

"It's ok, Tommy; not every male needs to be a man; it's just a stupid expectation society puts on everyone. I'll make sure you can enjoy being yourself just how you  are." She said and gave me a pet on the head, which hasn't felt so good at the moment.

"Talking about that, I want you to pack all your male underwear in a bag while I finish the bathroom, and we'll put it somewhere safe until you'll need it again. You're going to replace them with that nice underwear we bought you yesterday. OK?" She asked me, and I looked back up at her. No way, I'll just have those silly pants in my drawer. Mom could see it. And what if I need to go somewhere?

I opened my mouth to protest, but she instantly put her index finger in the air as a sign to stop.

"I told you what to do; you'll say, "Yes, sis,"  kiss my foot, and do as you're told. As you've been a good boy lately, I'll let you keep one pair of your underwear, and they have to be white briefs, which you'll keep at the bottom, beneath everything else, and you can only wear them with my approval. OK?" She said, and she rotated her open fist as a sign for me to now say as she told me before. I was so angry and nervous that I had to clench my fist, but I knew I had no choice.

"Yes, sis," I said, almost through my teeth. Her opened palm now moved, and it directed down to her feet, and I lowered my head and started kissing it.

"Thank you," I heard from above me, and I moved my head back up. She stood up, told me she'd come back after a few minutes, and expected me to be done and ready for her inspection. 

As she left, I took some bag I found in the corner and placed all my underwear in it, except for those white briefs I got to keep. In my now empty drawer, I placed the underwear she bought for me yesterday. It felt so ridiculous to see that at the place I had had normal underwear all my life.

Kim came in after I was already done; she took a peek in the drawer, took the bag with my normal underwear, and said good night without giving me any instructions for this evening or next morning. I've done what I had to do in the bathroom and gone to sleep. There was no call from Jenny that evening.

When I woke up, I did as I did days before: I made myself coffee and breakfast and then went to kneel in her room before waking her up. Morning routine as usual: I made her breakfast while she showered, she ate, and she said she needed to study. I was given a task to do some yard work, so I spent the morning pushing the mover, trimming, and cleaning around.

I came in at noon, as I was mostly done, and it became too hot to be in the sun. Kim told me to get in the tub and wash myself, but not to come out before she came. She came with handcuffs, which meant my cage was coming down. But to my utter surprise, she handcuffed my hands in front, not in the back as usual.

"Can I trust you?" She asked me, and I said, "Yes.".

"I'll unlock you and let you wash yourself down there. Don't even try to do something stupid, or I'll break your balls, I swear to God," she said as she unlocked my cage and pulled it off my dick. For the first time in weeks, I got to feel my dick in my hand, and I couldn't believe how good it felt. I forgot the feeling, and now it was better than ever. But I respected our deal, I washed it thoroughly, enjoying the touch, and at one moment she told me it's enough. I reluctantly removed the hands and was given a towel to dry myself. After I came out of the tub and dried off completely, she put the collar back on me and told me to put my hands under my chin. With a padlock she pulled out of somewhere, she locked the chain on the cuffs to the ring that still held that degrading inscription, so my hands were now locked under my neck. 

She pulled me out of the bathroom and took me to her room. My cock was so hard, she could have led me by it.

She placed me in the middle of the room and went to her closet, where she pulled out a silk scarf. She folded it in half and gave me the ends to hold it in my hands. At first, I was confused by her action, but then I felt the soft fabric of the scarf on the tip of my fully erected, sensitive cock. It felt so good, so soft and light. Too light. She turned around, sat at her desk, and started reading some books, while my hips started to rock back and forth in a futile attempt to get some more friction on my cock. But it was in vain, and even though I realized it, I just couldn't stop. I was trying to shake it, to move it somehow, and to fold it once more. But nothing helped; I just couldn't get any real grip. It was so frustrating that I started to whine and cry at some point.

Hearing me, Kim turned around and smiled.

"Please, Kim," I whined.

"What?" she asked, and I had no idea what I even wanted.

"Let me hump something." I managed to explain my need to both of us.

"You're doing it," she answered, and she was right.

"I need something firmer, please," I begged, but she just smiled and said, "No." I let out a sound of frustration. And then I realized it was easier to just let it go, as it wouldn't touch my cock. 

I let go of it, and it felt down on the floor.

"Bad boy, I told you to hold it," Kim said, raising up from the chair.

"I can't; no more, please," I begged as she walked towards me. She picked it up and folded it again, this time squeezing the ends and tying them on the chain of the cuffs, so it again fell down over my cock. I couldn't reach the knot to undo it; there was nothing I could do about it. 

"Please no, Kim," I whimpered, and she came closer to me, gave me a peck on the cheek, and I suddenly felt her leg on the other side of the scarf. I humped it hard twice, and then she moved back with a laugh. 

"Stay quiet; I need to study," she said and turned around, walking back to her chair.

"Please remove it, Kim; I'll whine until you do; I can't handle it anymore," I said, and she stopped in her tracks. She came a few steps back and suddenly clipped the waist of her pants and pulled them down. She stepped out of them by making a step forward, and then she did the same with her panties, giving me a clean look at her pussy. I shut up in shock, waiting for her next move.

She pulled them off her legs and came back to me.

"Open your mouth," she said, and I just spread them a bit more as they were opened from the shock. She stuffed her pants in between my lips as much as she could. They didn't fit in completely, but they were enough to fill my mouth. They were warm and soft. I was now humping that scarf three times faster than before.

She turned around and walked away, swinging her butt more than she should with a normal walk. She sat on her chair, took a book in her hand, and turned around to face me. She sat like that for a moment, putting her book in front of her face. And then her knees went wide, and her spread pussy was in my sight. I stared like an idiot while my hips still rocked back and forth at a steady pace. I knew I wouldn't come from it, but it felt good even though my frustration grew.

She stayed like that for a while, giving me a look above the book now and then, just to make sure I'm still suffering. After maybe fifteen minutes, I managed to calm down a bit and even remove my focus from her pussy as I realized it would be easier for me. But she must have noticed it, and I realized she moved a bit. I looked back at her, and now her hand was on her crotch, playing with her cunt. She was stroking her clitoral area first and then entering her pussy with her finger. And then with two. And again, stroking the clit. I went nuts again; I wanted to bite through that fabric in my mouth as frustrated as I was. 

I watched her play with herself until she came. She sucked her fingers clean before she used the paper tissues to clean herself up. And like nothing happened, she took that book that fell down from her hand at one moment during her solo and continued to read it like nothing happened. I couldn't handle it anymore. I fell down on my knees, then threw myself down on my stomach and started to hump the hard floor I was lying on. I didn't even look at her; I was too embarrassed.

I heard her walk, and her foot came into my view after the steps came close. I started kissing it even though neither said anything; I just knew what I needed to do.

"Turn around," she said, and it was hard to stop humping that floor; it was the most physical touch I got in a while. But I was hoping she'd sit on my face or something, so I turned anyway. But no, she just placed her foot on my face, and I gave it a few more kisses. Then she told me, "Stay," and I went back to read. My cock stood like a pole for a good 20 minutes after that.

When the clock turned time mom usually got home; she came to me and unlocked me so I could dress myself. She watched me so I wouldn't touch myself, and I had to massage her feet until mom entered the house, so my hands were busy. She sent me down immediately, saying I have to help mom get the launch done but that I can't do it on my own. As much as wearing tight pants over a cage felt weird, wearing them with my cock straining in them was much worse. I constantly looked down to make sure it didn't stick out.

I talked with mom while we made food, asked her about her day, and she asked about mine, with the remark that it was nice that at least some work got done after I told her I moved the lawn. We drank coffee together and prepared everything before Kim came down. We ate, and Kim cleaned up while two of us went in front of the TV. She walked through the living room, saying she needs to study. Three minutes later, my phone pinged, and I looked at it. The lock screen said, "Your room, 2 minutes," and I knew where I needed to go. She waited for me there and told me to undress, so I was in my birth suit in front of her. She told me to lay down on my back, cuffed one, and tied my other hand to the bedpost so they were spread wide.

"Take a rest; you're about to have a tough evening," she said, leaving the room and locking me in it. I had no idea what it meant, but I didn't like it a bit. Again, I tried to see if I could position myself to get a chance to hump something, but my tied hands kept me on my back, so I gave up and just rested. I was in a light nap when the key turning in a lock woke me up.

I looked at the door, and Kim entered. I could see her clearly even though night started to fall slowly. She sat on the bed next to me and petted my chest.

"Tonight some things are going to change, and you'll be the one to make the most important move. I got a feeling that lately you accepted your position and that you are more obedient than ever. I'm really happy about it, and I want you to continue being like that," she said with a smile and caressed my face.

"But there is one thing we have to change because I don't want to hide in front of mom anymore; it just takes too much effort, and I can't get your service for a whole day. Because of that, we are going to include her in our dynamic," she said, and I paused to see my reaction.

"I don't understand," I said honestly, because I had no idea what it meant exactly.

"Don't worry, I've planned it all. After we agree on everything, I'm going to set you free; you're going to put on your only male underwear and dress normally; and you're going to go down in front of mom and tell her you want to be locked up by me again." She said it dead serious. I think I went pale because, in that moment, I felt so cold that I was sure all my blood had gone out of my body.

"I won't do that," I managed to utter through my shock.

"You will, and you're going to convince her you really want it. You're going to do whatever it takes for her to really believe you and to send you to me to put you back where you should be." She planned everything, and my only job was to make it happen. But I really had no intention of doing it, and I said it clearly.

"No, Kim, I can't do that. Not after I asked her to help me out. It will make me look like a creepy nutjob; what will she think of me?"

"I think she'll be happy to hear it, and you won't even have to try that hard. But like I said, you'll do whatever is needed to convince her you really want it. After all, that is the truth, isn't it?" she explained, pretty sure in her words. Before she said the last part of the sentence, she started to rub my nipples gently. But even though my mind started to melt instantly, I managed to say no.

"I can't, Kim, please," I said, already moaning softly. She stopped rubbing me instantly.

"It will happen, Tommy; she'll find out you're back in the cage one way or another. I'd rather you tell her yourself than me showing her a video of you begging me to kiss my ass. Can you imagine what she'll think of you after that?" Kim asked me, and I started shaking out of fear. She can't do that, can she?

"Or maybe I could show her that essay you wrote," she continued.

Seeing my anxiety, she stroked my face gently. "Calm down; we don't need to go that way. I'm just mentioning possibilities." She tried to calm me, or at least faked it. I was on the verge of crying.

"There is also a video I haven't shown anyone yet," she said, pulling out her phone from somewhere before continuing. "I think it would be enough too." She finished and turned the screen of her phone to me.

The screen showed me in mom's room, sitting on her bed and going through her drawers. Then I pull out her vibrator and check it out before I decide to place it on my crotch. There was no sound, but the look on my face gave out my satisfaction. And then I started to pick up some clothes to collect my cum after I finish. She turned the phone back to her before the part where the vibrator died. Where the hell did she get that tape?

"What do you think mom will think of you violating her privacy? Or seeing her son playing with her magic wand like a girl?" Kim asked me, and now I did cry. I didn't want her to see that or to hear me beg Kim to kiss her ass.

"Don't cry," she said, wiping my tears with her hands. "There is no need for her to see that. You just have to be brave and tell her what you want. And I'll be more than happy to reward you for it. Would you like that?" She asked again and started to rub my nipples.

I managed to collect myself together, and I realized there was nothing I could do but obey her and do as she said. That will be the most painless way. And her fingers on my nipples felt so good.

"I would," I whispered to her as my voice broke.

"Of course you would," she said as her rubbing got harder and faster, and I moaned like a girl. 

"So, have we agreed?" She asked me, and with a lot of willpower, I said, "Yes.".

Sorry for the very late delay but here is what happened after the mall.

After driving home and getting inside she let me clean off my face and take the gag off, I never realized how soar my jaw was until now. It hurt to talk, she then asked if I was ready and led me to the bedroom. After blind folding me and strapping me down she started using a vibrator on my cage. Coming close to multiple orgasms, I then heard the popping of the lid to the bottle of lube and felt her cold fingers fill my hole. After a few minutes of her fingering Me I felt the pressure of something larger going in.

I let out a moan as I felt her enter me, feeling her going in and out felt so good, letting out moans of pleasure I loved it, Her calling me her little bitch and that I’m her cock whore. Then I felt it I knew I was finally going to cum while caged. I had never been caged this long before so I had been building up for a while. After a few more thrusts of her cock I felt it Right as my cum started to explode from my cage I felt her rip the blindfold off, and that’s when I saw it. There was no strap-on there was no fake cum. It was all real. It felt so unreal, I was in so much shock I didn’t even realize she was collecting my cum and shoving it into my mouth.

She asked How I felt now knowing the truth about her and I couldn’t even respond. She finally jolted me back to life by sticking her cock back into my ass and going to town while I was laying there. I told her to stop and that I needed a minute, she told me no and that it was too late. I belonged to her. She was videotaping the whole thing so she said she would post it if I ever left her. After reassuring her I wasn’t going anywhere and that I needed a moment to process things we took a break.

I hopped in the shower and just sat for what felt like years until I once again felt her cock enter me, it startled me back to focus but I felt nothing but pleasure, I moaned as she fucked me until I again exploded cum all over the shower glass. She told me good boy and to get on my knees and clean her off, I did as I was told. Never sucking cock before I had no clue what I was doing, but apparently I was a natural because she exploded in my mouth after about 30 seconds and forced her cock down my throat until she dumped 2 more loads and forced me to swallow. After the shower we went at it again for another hour. After filling my ass with countless loads of her cum she plugged me with a bigger plug and told me I was to sleep naked and plugged for now on. I swear when my head hit my pillow I was gone.

After waking up to her cock poking me in the back I returned the favor by taking out my plug and shoving her up my ass to fall back asleep while spooning. I woke up again to her thrusting inside of me until she explained. I felt ropes of cum fill my ass. she then explained to me that I was now her toy. When I talk to her it was now mistress, and that I was now her sissy slave. Now that I could cum in my cage it was permanent and anal was the only was to release. I was to only wear girl clothes 24/7 since I only worked from home this wouldn’t be an issue. and I was to be plugged 24/7 unless we were fucking. My normal life was now
over.

This ist Part 6 of a fictional story about a horny 19 year old, who is turned into a prejac against his will and held in chastity for days or weeks. He gets lots of teasing, a few ruined orgasms and some ballbusting for many weeks [F/M and M/M] – getting worse and worse.

This Part contains hard ballbusting. Parts 6 und 7 are more about how Luke gets out of his cage and then permanantly caged. If you are not interested you can skip these and continiue with part 8 once its ready.

In case you missed the previous Part 5 - Take your time or the Beginning

Luke was left caged and chained after his sperm donation. Saving humanity wasn't as fun as he'd expected… again just a ruined orgasm…. and a pretty premature one. He blushed again.

Luke's goaler went straight back to her office. She was soaking wet. She had never seen such a quick cummer before. It had taken him just seconds to loose control. And it was driving her crazy to also ruin his orgasms! Of course she was allowed to give him full relief during the sperm donations, but this was so much better!

She turned on the stream surveillance cameras with Luke still chained and started to masturbate. Now the best part would start!

Luke stayed chained and caged for a while. His arms were aching when a well known guard (the one he had bit before) entered, accompanied by a female guard.

‘Oh no….’ Luke whispered and tried to back off, but the chains held him in place.

‘Hey there’ the guard greeted him in a good mood. ‘I am supposed to get the last drops of your precious spunk out of your dick, so nothing gets lost. I've really been looking forward to this!’

The female guard looked him up and down before she pinned her eyes on his caged dick. ‘I heard you couldn't hold it longer than a few seconds this time.’ Luke blushed again.

The guard took the key and put it into the lock of his chastity cage, but didn't turn it.

‘Let's be thorough about these last drops’ with a sadistic grin he grabbed Luke's exposed balls and squeezed them hard. Intense pain shot through Luke's lower body. Luke yelped and tried to turn away, but the chains wouldn't let him.

The guard slowly increased the pressure and watched Luke starting to panic. Then he turned the key and the cage opened, releasing Luke's cock from its way too small prison into the donation tube.

It quickly grew from being squeezed down to less than 3 inches to about 8 inches - due to his pain and panic not to its full 9 inches. By doing so it slowly released a trickle of cum into the tube that was left of his ejaculation while caged.

The guard squeezed and twisted his delicate balls. ‘Get it aaaall out!’ he said. The pain made Luke shriek - but he still tried to keep his reaction under control.

The female guard watched the muscles of Luke's lean body flex when he suppressed another shriek. ‘I like your new friend. He tries to act tough.'

She slammed her fist into Luke's stomach, making him cough and breaking the remains of his self control. The male guard pressed the thumb of his second hand hard on his left ball and made him cry out.

Luke had only heard before, that you feel intense pain to your balls also in your kidneys. … at the moment it felt like his left ball and left kidney were both in a vice!

The female guard dug her thumb into his right ball making him scream ‘Aaaaaaah, pleeeeeaaaase, stooooop!’

‘Oh he's already begging’ she stated. ‘Time to really get started!’

That made Luke panic even more. They both took their time and kept squeezing his balls alternately. He could feel them get flattened more and more and screamed at the top of his lungs. Tears filled his eyes. By now his whole lower body was in agony and he was shaking.

‘Too bad I can't go as far as I would like to. He still needs to produce sperm…,’ said the guard and sank his fist into Luke's balls. A different kind of pain flooded his body and made him whimper.

‘I think he can take a little more,’ added the female guard and punched his now swelling and extremely delicate orbs three more times, making Luke grunt. By now he felt too weak to scream.

Next the guards ripped the ring of the already opened cage from his balls - pulling and squeezing them hard. The pain made Luke cough and drop into his chains, his feet dangling on the floor.

‘That looks like an invitation I'll gladly follow,’ his tormentor said, looking at Luke's widely opened legs. The Kick he sent into his exposed balls lifted him in his chains. Luke thought he would throw up. But that was interrupted by a second and a third kick by the boots of the female guard.

The pain felt so intense, Luke almost got unconscious, his vision blurred. His whole lower body was throbbing in agony, his dick almost soft now. It felt surreal when his chains were opened and he fell to the floor face first.

‘Do you want to walk or prefer to be dragged by your balls?’ he heard like from a distance, grasping the meaning a few moments later.

To protect his balls from any more tormenting he gathered his last strength and pulled himself up by the chains. It surprised him that his shaking legs actually still carried his weight.

Luke grabbed his clothes like in trance and stumbled behind the guards. He clutched his balls, close to throwing up with every step.

‘Too bad...’ the female guard said as they led him to his quarters.

‘Yes, too bad!’ Lukes goaler sight in her office, watching the camera feed. She knew he would be caged again very soon. And this time she would make sure it was for good!

With these thoughts she intended to watch Luke's walk to his quarters while clutching his balls. But now she was the one who couldn't hold back any longer as her orgasm built.

When they reached their destination Luke had to steady himself on the doorframe, exposing his still naked and dangling balls from behind.

When the guard's boot hit his balls from behind (he didn't know which ones), Luke's legs gave in and he fell into his room. The door closed behind him when he curled into a ball.

Mike rushed to his side. ‘Are you OK?’

Luke just whimpered.

‘That was the one you bit, wasn't it? You should be very careful to make enemies here…’

Part 7 will follow soon

ALL CHARACTERS ARE OVER 18

4AM: Nick wakes up from an erection. Nick checks his phone and is shocked that this is the first time he woke up at after sleeping for hours. He goes to pee as that settled his erection the night before. It works and he goes back to bed. He plays a game on his phone for a bit and then tries to fall asleep. It takes about 10 minutes but then he is back asleep again.

He wakes up a second time at 8AM. He checks the time again and is shocked. He was gonna wake up around 10 so he decides to just stay awake for the day now. He is in disbelief at how few times he woke up from the cage. For the first time he has a little bit of hope that this chastity agreement will work out. He gets ready for the day and goes downstairs to get breakfast. He makes himself a bowl of cereal then hears his dad walking down the stairs. “How’d you sleep?” His dad asks. “Not bad actually its getting better.” Nick tells him. “See son with time things will get better.” Joe tells Nick.

They eat breakfast together and make casual conversation without mentioning their cages. Then Joe gets ready to leave for work and Nick goes in the living room to play video games. Joe heads to work and says bye. While Nick is doing better wearing the cage he still feels just as horny. And curiosity is starting to get the best of him with his dad. He feels like his dad knows too much about chastity for someone who has only been wearing a cage for 2 days.

So after watching Joe drive off Nick goes up to his bedroom to see if he can find anything. This is unlike Nick is bisexual but he has never thought about his dad in a sexual context before. Nick arrives at his dads room and opens the door.

He walks in and to the right of the door is his dads dresser and on it he sees the chastity cage that his dad is wearing. Nick is furious, his dad agreed to wear the cage along with Nick and now he is cheating on their deal. Nick is so mad now he wants to rip his cage off but he keeps looking to find more things in his dads room.

He opens his dads top draw and sees underwear in it. However he doesn’t just find boxers in the drawer, there are also jockstraps and women’s panties. As far as Nick knows his dad isn’t seeing anyone so by that and the size of them he can only assume that his dad was wearing them. He looks in all of his dads drawers but he doesn’t find anything else interesting. He moves on to looking in the bathroom. He goes in his dads bathroom and opens the cabinet underneath the sink. He finds the usual, Toothbrush, Toothpaste, Deodorant, Razors. But then there is a small cardboard box and he pulls it out on the floor and opens it. It is a box full of more than 100 condoms. He is so confused. He thinks again about who his dad has dated and the last time he met any of his dads girlfriends had to have been more than 3 years ago. He is trying to think why anyone would have this many condoms. He can’t figure out why but he doesn’t find anything else in the bathroom so he moves on to his dad’s closet.

He walks over to his dad’s closet and opens the door. He sees his dad’s clothes hung up on the rack and then he sees a large clear bin on the floor. The bin is clear but there is some sort of bubble rap or paper hiding what is inside. This intrigues Nick and he open it. He doesn’t know where to look first. He sees another small box of condoms, Multiple dildos, 2 fleshlights, Butt plugs, Enema’s, Gags, Whips, And Then he sees 7 chastity cages ranging in size. This confirms his suspicions that his dad has worn a cage before. And it makes him think maybe his dad wasn’t cheating on their agreement and he was just wearing another cage he had. He had almost no hope it would work but he grabs the keys attached to each of the cages and tries all of them in his cage’s lock. He isn’t surprised when not a single one opens his cage.

Nick is just sitting on the floor of his dads bedroom with a box full of his fathers sex toys. He cannot believe that this is really happening and that he found what he did. His mind wanders to: Who did he use these with, Or even did someone use these on him. Was his father gay or bisexual. He had to be into men somehow if he had a dildo Nick thought. Unless he was using it on a girlfriend. But he still cannot figure out why his father would have so many chastity cages. Nick looks in the rest of the closet and doesn’t find much except more underwear, Both mens and women’s.

He puts all of his father’s belongings back and wonders what he should do. He can’t tell his dad what he found because then his father will know he looked in his room. But this is gonna kill him wondering about this forever.

Day 28:

Jenna and Brian slept in after last night's endeavors. Even Jenna was tired. Brian, however, was sore, and battered up in his rear. He groaned when he got up to go to the bathroom and piss through his cage. He realized he had the smell of precum all over his cage. After some surface level cleaning of his cock and brushing his teeth, he walked back into the room to see a softly snoring Jenna.

She looked so innocent and adorable in her sheets wrapped around her like she was some burrito. Brian knew the sadist she really was and his cock twitched and strained in his cage as if agreeing. He went downstairs to make her a surprise breakfast.

As the morning grew older, she eventually woke up to a full breakfast in bed.

"Aw, Brian, thank you," she said with a cozy smile.

Brian beamed with pride.

"I really fucked you that hard huh?" she asked with a coy look on her face.

Brian averted her gaze, cheeks reddening.

"Well, maybe I'll give you the privilege again," she said with a scoff as she dug in.

He didn't know if she was serious or not, and he definitely didn't know if he was excited or not. Eventually she finished, and freshened up further. Eventually they both showered and Jenna occasionally teased his cage in the shower.

Finally, after all of that, noon rolled around and the two lazed about on the couch. Brian watched his memes while Jenna read her book. After some time, she shut her book, yanked Brian's head down to her crotch. She had been wearing panties to feel comfortable. Brian smelled her scent as she shoved his nose into her pussy. He slid the panties off and dug in.

After another hour of just eating pussy, she ordered him to go upstairs. He obeyed, feeling that tinge of excitement and a wave of horniness as usual.

She came up and mounted his face as usual. This time she just wanted her asshole licked. She laughed as he strained in his cage.

he heard the keys dangled and excitement flooded his heart (and cock). She slowly unlocked him, not saying anything about it. He felt his cock spring up, eager to please and be pleased. She gently started stroking it, and Brian already felt on the edge of exploding. he let her know by holding her ass, firmly.

"So I have a deal for you," she said in a sultry voice

Brian hummed in response, diligently licking her asshole.

"I have this friend named Katlyn. You know Katlyn?" she asked.

"Mhm!" he hummed again.

"Well I will let you have a full orgasm if you let me tell her about this whole situation we have going on. and also if you agree to let me involve her."

Brian's heart could have exploded through his cage. He didn't know if it was due to the prospect of having another woman involved, or whether it was at the idea of having a full orgasm."

"So what do you say?" asked Jenna.

Brian almost begged as he agreed. "Yes Queen Jenna, please!"

"Okay!" she said, in a bubbly voice as she began stroking his cock at a merciless speed.

What happened next was biblical. Brian immediately felt his cock not only tip past the edge of a full orgasm, but rocket into the stratosphere. The orgasm hit hard and fast and was unrelenting. Waves of pleasure overwhelmed his senses. He could feel it in his gut and his vision blurred from the blood rushing around. Jenna's asshole became his focus point to not lose himself, and he licked her out religiously as god's own wrath followed his explosive orgasm.

For Jenna did not stop stroking. she did not even slow her pace. she stroked faster if anything and Brian went from revolutionary pleasure to mind bending pleasure-pain. He bucked and heaved and protested, but Jenna through her laughter held him down and continued stroking. this went on for an eternity it seemed before Jenna grew fatigued from fighting and stroking.

Eventually she let go and the two gathered their breath.

"Wow that is a huge fucking load," she said with a hint of awe. "How was it, my little butt licker?" she asked in a patronizing voice. "Worth the wait?"

Brian couldn't respond properly.

"I'll take that as a yes. Jeez, I know I ruined your orgasm last time, but I really RUINED you today. I mean I wonder how it'll be if I rail your ass as I stroke your cock."

Brian gulped and didn't respond again, but he noticed Jenna already thinking of the possibilities.

"I wonder what Katlyn will want to do with you," she said with a mean smile. "She's been in kinky relationships before. She's far more experienced than I am."

Eventually, Jenna locked him back up, and ordered him to clean the mess. The day ended with lazing about, and Jenna locked to her phone, texting Katlyn about who knew what.

My table of contents for not just the chapters of this story, but all the stories I have available and where to get them, updated daily.

This is a gender swap rewrite of the original femdom story, Lifelong Friends Become More.

​

Chapter 46

Megan was vaguely aware of Josh starting to untie Kelsey, and she let out a tired yet satisfied moan as she sort of lay on top of Kelsey’s back. She had gone completely limp and her Feeldoe was still buried inside of her. Summoning the energy, she straightened up and carefully and gently pulled out. Kelsey moaned with it, but didn’t move. Megan’s legs felt like jelly, but she carefully removed the Feeldoe entirely.

Josh was just finishing untying Kelsey’s ankles and yet she still just lay there in the same position, bent over. “What can I do to help,” Megan asked.

“Maybe just take the Feeldoe to the bathroom to clean it up? I will tend to Kelsey,” Josh replied with a smile.

“Of course Josh,” Megan said happily, eager to help. She was a little concerned with Kelsey’s lethargy and worried that maybe she had been too rough. But Josh would take care of her initially. She washed off the dildo and then came back to the bedroom. Josh had gotten Kelsey to move and she was now laying on her back in the center of the bed, with her eyes closed.

“Is she okay?” Megan said worriedly.

“Oh yes,” Josh said and could see and appreciate Megan’s concern. “That orgasm that she had was nothing like she had ever experienced. She said it was like her whole body orgasmed. She is completely drained of energy and even will, but she is absurdly happy and very deep in submissive space. I went to unhook the cuffs on her and she asked to leave them as they are,” he chuckled. “You did wonderfully Megan and Kelsey is in blissful rest. I hope you enjoyed it as much as it looked like you did?”

Megan was so relieved that not only was Kelsey okay, but she had loved every second of it, and that she herself had been the cause of a mindblowing orgasm for Kelsey. She did look very peaceful laying there on her back, her hands under her body. “You have no idea Josh. You were so right. I just kind of completely lost control and it was one of the best orgasms of my life too. My legs still feel like jelly,” she laughed.

“Well, let’s get you into bed too,” Josh said and placed an affectionate arm around Megan and escorted her to one side of the bed. Josh then grabbed the blankets, covered the both of them, and got into bed on the other side of Kelsey. They both ended up draping themselves over her, all three of them still nude. They both rested their heads on her chest where they could see each other and resume talking, using Kelsey’s breasts almost as pillows. The arm they each draped over her waist met and they caressed each other as they spoke. Kelsey seemed oblivious.

“Thank you so much for this experience, Josh. It was so much fun and really helped me to realize how much I want this for myself. The two of you have been so welcoming and warm to me, a relative stranger, and made me feel so good. To experience not only these dominant desires made real, but also sex with another woman was truly mind blowing. I will remember this night for the rest of my life. I can not thank you enough,” Megan said quietly.

“Oh Megan, you are more than welcome,” Josh replied, stroking her arm. “It was so much fun for us too and I think it also brought us closer together than we even were before. I think we got very lucky in the kind of person you are and how your desires so meshed with ours. What had started out as just a treat to watch Kelsey submit to another for me turned into far more I think. She genuinely wanted to serve you and please you, and it was wonderful to see. And for me to experience sex with you was also wonderful. I um…I hope you can stay tomorrow?” Josh asked, aware that his question had come just after talking about sex with each other.

“I can stay as long as you like,” Megan said with a pleased smile. “I have to work on Sunday, but I am free all day tomorrow and would be very happy to enjoy the day with you if you like.”

“I very much would like,” Josh said softly and then closed the distance over Kelsey’s chest to kiss Megan’s lovely lips, feeling such affection for her over sharing Kelsey like they had. As much as he wanted to explore more sexually with Megan tomorrow, they should probably also plan to go out for lunch or something and just get to know each other better. Josh wanted to develop at least a lasting friendship with Megan, but based on tonight, he was also hoping for more. He knew he should go slowly though. He didn’t know what he wanted in regards to Megan for the long term, but for the short term that meant some more fun tomorrow and trying to develop a friendship. What happened beyond that was not clear, but it would happen naturally.

Megan was actually a bit frightened by her own feelings tonight and how they might end up hurting her in the end. When Josh kissed her, she felt such a surge of emotional warmth that she almost cried. Even in her wildest imaginings of tonight, she had not thought of how far the sex would go. And it was all as wonderful as she said. But they had been so warm and welcoming of her that it wasn’t just the kinky sex. She felt like she was a part of them for tonight and for the first time, felt that inner loneliness she always carried with her, start to crack.

Megan had dated plenty, but she had never felt even a little of what she felt tonight with Josh and Kelsey, and she wanted it to continue so badly. She wanted to explore these feelings to their depths and embrace them, but she had to keep reminding herself that they were an established couple and she was really an outsider. She had jumped on the chance to continue things tomorrow because Josh and Kelsey made her not feel alone any more, but she knew that it could all end just as quickly. She was afraid that if and when it did, it would send her back into depression and send her life back into a spiral of depression.

On the surface that sounded kind of absurd, as it was just a weekend of sex. But she felt such a connection with them that she knew it wouldn’t take much of a trigger to send her into depression again. Years of therapy reversed. So she very much wanted more with them and hoped there could be. She kissed Josh back just as gently and let out a very contented sigh.

Kelsey hadn’t moved when they had climbed into bed on either side and draped their amazing nude bodies over her. She was quite aware of them talking softly over her chest. And kissing. It was an amazing end to an amazing evening. She didn’t have the lofty thoughts or worries that either of them were having though, she was just happy to be a part of it. As Josh had said, she was in submissive bliss and didn’t want it to end. She was completely drained, but it was a good feeling. She wanted nothing more than to keep serving and that was really what filled her head at the moment. Her happiness at serving in whatever way she could.

The three of them slowly drifted off to sleep, entangled with each other, but warm and comfortable, both physically in the bed, and with their shared feelings…

​

End of ‘Lifelong Friends - A Female Submission Story'

Final word count - 79925

“Okay, i think mom might know where she is” she’s sending a text to her mom.

“Where who is Miss Chelsea?” Muse is standing behind us as we are at the door to the pool area. Her eyes are clear, she seems somewhat lucid, as if she was a different person. Her latex suit off, replaced by a tight fitting black T-shirt over her bathing suit. Her prosthetic arm not there, the rest of the arm missing from right above the elbow.

“Oh, Muse, you’re not-“

“Miss Eva finally got my medicine.” She smiles wide, her sharpened teeth creating a gnarly grin. “And she’s on her way down to join us.”

“Good. I always say Eva evaded the sun.” Chelsea chuckles. “I’m kidding of course muse”

“We do need to get more sun.” Muse laughs sheepishly. “Today does seem like a good day to do that”

I smile and go to shake her hand, i feel myself starting to slip out of the bikini bottom, leaving myself nude in front of everyone. I blush super deep and try to cover my quickly growing erection. Muse winks and heads to the pool.

Chelsea puts an arm around me. “Was that too embarrassing?”

“No ma’am” I’m looking down at the ground letting out a squeak. she giggles a little and kisses my cheek. “You….”

“I might’ve untied the side of your bikini.” She gets in close, helping me secure it while whispering. “You didn’t tie it off too well to begin with my sweet puppy”

Heading outside, the pool has lounge chairs all around it. It’s fairly big with a slide and a diving board. Muse is already laid out on one of the loungers, smiling contently. Pulling a lounge chair near a table i lay out one of the towels I’m holding for Chelsea.

“Thank you puppy” chelsea lays down on the lounger and begins stretching out. As she lifts her arms above her head, her chest lifts subtly, she lets out a cute little grunt as she stretches. After seeing me watching her stretch, she grins, “Pull your chair over to me puppy, time for another present.”

Pulling my lounge chair up next to her i look over and see Muse watching us.

“Hey Muse,” not paying attention to anything, “what’s going on with your teeth? They’re all sharpened.”

“Oh, these?” Muse smiles wide, moving her cheeks to show more of her teeth, “they’re just in case i need to get myself out of a tie in case of an actual emergency, like if Miss Eva had me suspended midair and the venue had to evacuate. the safety knot is useful and all but i need a quick breakout strategy.”

“Plus that witch at The School had done a lot of damage to Muse’s teeth already.” Eva joins us poolside, putting her chair next to Muse’s. “Sorry Cait, you should’ve told him yourself”

“No…. Don’t call me that. please, Eva?” she looks almost afraid of being called her real name. “Never again”

“I’m sorry, it was a slip my Muse” She holds muse comfortingly as Chelsea puts an arm around me.

“I want you to tell me right before you’re about to cum, i want you ready to burst tonight.” She whispers in my ear and starts to slowly rub my cock through the bikini bottom, i start to get more erect through her touch. She undoes the front of my bikini and starts to stroke me while nibbling on my earlobe, causing me to squirm and whimper. “About to blow already? Maybe you do need more time in your cage”

Eva looks over at us and laughs a little, “little sister i think he’s nervous. Isn’t that right little fly?”

“Y…” i start to moan from pleasure. Feeling myself get erect from being called little fly, a look of guilt and pleasure shows on my face. “N… no ma’am”

“You like being belittled, little puppy?” Chelsea whispers seductively into my ear as her touch gets more tender, almost tickling the tip of my cock with her nails. “Don’t want to be embarrassed in front of mommy and her sister?”

Hearing this sends me into an almost orgasmic state and i start to tap on my thigh with my hand, my nonverbal cue that im close to cumming.

“Use your words, is someone close?”

“I’m close, I’m about to-“ i feel chelsea’s hand leaving my cock as i start to twitch, wanting to cross the edge unsuccessfully, my cock starting to get flacid again. She kisses the top of my head.

“It might be your birthday but i still get to have my fun.” She whispers into my ear just loud enough for me to hear.

After being edged repeatedly i look over to Chelsea with a pleading whimper to stop. Eva is chuckling a little.

“I think he’s ready for a break little sister” Eva looks over at chelsea. “Don’t break the poor boy”

“Oh fine, fine.” She kisses me on the forehead. “I had my fun for now anyway.”

My table of contents for not just the chapters of this story, but all the stories I have available and where to get them, updated daily.

This is a gender swap rewrite of the original femdom story, Lifelong Friends Become More.

​

Chapter 45

This would be a lovely culmination of the evening’s activities, Josh thought. Watching this sexy tiny girl fuck his Kel hard and watching and hearing her pleasure from it. Even now, with the Feeldoe buried deep inside Kelsey, Josh could see how much effort it was taking Megan to hold herself back, and it was so fricken hot to see the restrained desire on that freckled face. She continued to sooth Kelsey with her words and caressing hand, but Josh could see that she was raring to go. This would probably exhaust both of them.

He was satisfied though, and wasn’t sure if he would just continue to stroke Kelsey’s hair, or have her suck his cock while Megan brutally fucked her. Both had their appeal, and after they would at least take a break. Megan was spending the night after all, and perhaps they would also have all day on Saturday.

Kelsey once again felt that all encompassing sensation of being uncomfortably filled, this time by Megan. She was still grateful for her gentle empathy though as Megan told her how well she was doing and continued to caress her back. It helped to relax her more and reduce the pain. Josh then gently lifted her head and said, “Why don’t you see how deep you can take me into your mouth while you get used to Megan filling you?” he said, repositioning himself so that his cock was just below her mouth. Without a word, Kelsey opened her mouth and took it in and for the first time, she was being penetrated from both ends. She moaned, feeling how helpless she was and how fortunate to be used in such a manner by these two amazing people.

Megan was having difficulty restraining herself, but knew the effort was worth it. She had anal sex once before and it could be hard to take, and Kelsey really was doing so well being filled, and by a cock much harder and larger than the one she had taken herself. She wanted Kelsey to enjoy this, but so far much preferred being on this side of anal. She also had a good time teasing Josh about using it on him, but she would in a heartbeat.

As she watched Josh reposition himself for Kelsey to start sucking him, they shared a smile. It was warm and conveyed without words just how pleasant the evening was. Megan had long since lost her nerves and both of them were responsible for it. They were so open and welcoming. She started to very slowly move her hips as Kelsey got part of the way down on Josh’s cock.

Perhaps she should have held still longer though. Even the little slow movement increased her desire exponentially, as did Kelsey’s now muffled whimpers. She slowly started to pull out a little further, feeling the bulb inside of her press against the top of her pussy in a delightful way, only to reverse her hips and slide it back in and feel it rubbing against her clit. She let out a high pitched moan of desire and there would be no stopping her now.

Josh could see it too as Megan started to gently thrust. He could see how much she was holding herself back but could see that it wouldn’t last long, and it was exactly what had happened to him. The feeling of power from the dynamic along with the physical feedback from the Feeldoe was too much for Megan to overcome. He could hear (and feel through his cock a little) Kelsey’s whimpers, but knew she was in a good place for Megan to start to lose her control. So he just leaned back and alternated his view of Kelsey trying to deep throat him, and Megan trying to keep herself in check. It was admirable, but Josh knew it wouldn’t be long now.

It wasn’t. Every time Megan pulled back, she pulled back a little further before going back in again a little faster. She kept this up for as long as she could until she pulled back so far, she could see the head of the Feeldoe once again. She thrust her hips forward hard this time and Kelsey let out a muffled squeal. That made Megan laugh softly and do it again. And again.

At that point, she couldn’t return to slow. She kept doing the long pull outs followed by swift thrusts in, adoring the sounds that Kelsey made and feeling so powerful. She started to develop a regular rhythm now and it didn’t take all that long from there to start fucking her hard, desperate to hear Kelsey’s noises and to stimulate herself. The Feeldoe was definitely working its magic on her with every thrust.

Kelsey could no longer concentrate on trying to get Josh’s cock deeper into her mouth as Megan started to fuck her. Every thrust seemed to get harder and harder and it hurt, but it was also absolutely wonderful to be subject too. The feelings of submission washed over her like a giant wave of emotion and she relaxed more as she completely surrendered to it. She didn’t have a choice regardless and her brain was able to take that to set itself free and just surrender to it completely.

Josh let her come up off his cock and she moaned as Megan’s hips started to smack against her still sore ass. The sounds that Megan was starting to make were amazing too. Such cute notes of pleasure and her pleasure did more than anything else to arouse Kelsey more. She was glad she was Megan’s first and would volunteer again gladly whenever Josh allowed. Her goal tonight was both the dominant's pleasure and she was doing her best to make sure they were happy.

She was being well used and she could really feel it, especially in this position, but she wouldn’t want it any other way. This was what she was meant to be.

It was then that Kelsey felt something building within her. She had felt it before the last time that Josh had fucked her ass. She moaned louder as the sensations built and looked at Josh with hope and worry. He seemed to read her mind and her expression. He reached down and cupped her face. Her entire body was moving with the forces of Megan’s thrusts now, but her face was a mix of emotions and sensations. “Let it happen baby…Just let it go and let it happen…” he said softly, encouraging her. He knew what part of her facial expression was because she had shown it last time as she was building towards an orgasm.

She moaned and whimpered and surrendered more and felt that sensation slowly building. She needed to show Josh her gratitude, and so she stretched for his cock again, taking it into her mouth and blowing him normally. Megan’s thrusting naturally helping her to go up and down on it. Megan’s cries of pleasure riding over the top of everything, the sensation grew in her causing her limbs to start tingling. She looked up at Josh and saw his happiness and the love in his eyes as he leaned back and enjoyed the attention from her mouth. Megan thrust into her and she was starting those loud squeals of pleasure that meant she was approaching her own orgasm. Kelsey felt like her limbs were going numb as pins and needles traveled up them. The sensations were intense and overwhelming. She sucked Josh’s cock wantonly needing his pleasure and approval.

Megan had lost all semblance of control and wasn’t trying to control herself any longer, taking Kelsey’s ass as hard as she could. Kelsey’s noises were starting to change into something she hadn’t heard before but they were hot and her own noises were starting to drown them out. She knew she was loud during sex, but she didn’t care. They accepted her for who she really was and that was all that mattered. She was able to just let go and be herself. Her orgasm was building quickly and she could tell it was going to be a monster that would completely wipe her out.

It crashed over her like a tidal wave as she slammed one final time into Kelsey, practically screaming with it. Simultaneously, Kelsey cried out and her entire body started to shake. Her body shook uncontrollably as the most intense orgasm of her life hit her like a tidal wave.

Josh watched them both orgasm in ecstasy and was so pleased and decided it was time, right in the middle of Kelsey’s orgasm. He thrust into her mouth a few times and let go, his orgasm mixing with theirs and sending jets of cum deep into Kelsey’s mouth, which she somehow had enough control to reflexively swallow.

Finally, Kelsey suddenly went completely limp on the bed and after Josh had shot his whole load, he started to get up. Megan was still buried inside of her, but she had half fallen on top of Kelsey as her orgasm subsided and her little body occasionally trembled.

First things first, Josh started to untie Kelsey’s ankles…

Everyone in this story is 18 or older.

Parts 1, 2, 3 and 4

My mom and sisters made very clear that 'Jimmy' wasn't to be seen around the place any more. Even when Tyrone was gone, I had to stay as Britney. That way he wouldn't ever need to call ahead or double check, he could come and go, using Samantha, Mary and my Mom as he pleased.

With Tyrone listed as an actual keyholder now, I was too nervous to put in a request for orgasm. Sometimes I got so horny I felt physically weak... but the idea of begging to cum and my long-time bully officially vetoing it was way too much to handle.

But that didn't seem to stop the girls being demanding with me. After all, they were very busy now with Tyrone's cock, so many of the domestic duties fell to me. In return, instead of orgasms, my mom and sisters taught me to put on my own makeup, to walk in heels, even how to talk more like a girl.

At first I resented my feminisation. But, just like Anita promised, the girlier and more sissified I acted around Tyrone, the less aggressive he was with me. I stopped having to fear him bodyslamming or bitch-slapping me. Though he did tend to grab my ass as he walked by.

When the school week started again I was allowed to wear masculine clothes, so long as I wore a pair of panties underneath. I kept out of Tyrone's way as much as possible, knowing on some level this wouldn't be enough. And I made an appointment, as early as I could, to see Anita, the school counsellor and the woman who'd put all this in motion.

Anita is in her late twenties and has a short bob of blonde hair, along with girl-next-door good looks that remind me of Taylor Swift. She is very curvy and, whilst she never dresses scandalously I've often wondered if she knows what those tiny skirts and low cut tops she wears do to guys like me. I had a crush on her since our first one-to-one, and the fact she knows all my naughtiest secrets only makes me feel even weaker around her.

Still, she's always given the impression she at least cares about what's best for me - even if I can't always be her top priority. So it's with a locked, leaking dick and a huge blush on my face that I explain the issue.

"I'm doing everything you and mom and my sisters... and god, even Abigail... I'm doing everything you told me to. And, yeah, I guess it's 'working'. But... Miss... I need to cum. And he's on the app now. What if he won't let me? I... I don't think I could take that humiliation."

Anita - Miss Jones - gave me a long, pitiful look.

"I won't lie to you sweetie. Tyrone probably will do that. Veto you. But... he'll need a reason. And I can override it if his reason is dumb or unfair or impossible." She leant forward a little, her perfect tits bouncing beneath her blouse in a way that made it seem like the buttons could pop off at any second "But if he... I don't know, makes you clean his room or do his homework for a week, then that's just part of showing respect. And it's not like you have to do anything he tells you to. According to the most recent studies, beta males like you don't need to orgasm at all."

She said this last part so nonchalantly I thought my balls were going to shrivel up into my body. Like it would be no big deal if I never came again, if Tyrone intimidated me out of even jerking off while he used all the women in my life as fleshlights.

"I know you're scared of him. But, like you said, he's stopped being so aggressive now you're openly a sissy around him. So get out the app and make a request. Ask me, right now, to let you cum. I promise if he vetoes it unreasonably, I'll override it."

I was scared but the sight of Anita's round, jiggling tits was too much for me to bear and I nervously keyed in the request, my thumb quivering as I pressed send.

The veto response was immediate - Tyrone must have added it pre-emptively, ready for if and when I made this request. I was too scared to read it. I scrunched up my eyes and asked Anita to read it for me.

"Britney needs to act like a real girl. That means learning to suck cock like her sisters."

I blinked a few times, like a rabbit in the headlights.

"I... I did already." I protested, and told Anita all about how Tyrone had rammed his huge dick down my throat on Friday night "So... you'll override it?"

Anita seemed to ignore me at first, texting back and forth with someone. Eventually she told me, like it was the most reasonable thing in the world:

"He wants you to learn to do it well. Really get him off with your eager little sissy mouth." I felt like my insides were melting. Anita picked up on the terrified look on my face "Don't worry... I'll judge when you're 'good enough'. Not him. I'll help train you, so I'll be able to tell when you're good enough."

I felt like I was about to cry. As if comforting me she continued

"You don't have to do it. Like I said, boys like you really don't 'need' orgasms - men like Tyrone do, often, and not just through masturbation. But for you" she shrugged "denial is a natural state. So it's up to you - come to my office each lunch time and practice, or just stay locked up."

It had been one thing submitting to him, briefly, letting him use my mouth a few nights before. Yes it had been degrading but at the time I'd told myself it would be a one-off, a way of showing I knew my place. The idea of instead learning to worship his cock, day in, day out. Learning how to make him really feel good...

I swore to myself I wouldn't do it. I could go the rest of the school year without an orgasm, then move out of my mom's place and... and...

Even as i made the promise to myself I wondered, deep down, how long it would be before I was on my knees.

ALL CHARACTERS ARE OVER 18

First Night in the cage:

1AM: Nick wakes up for the first time. Nick is awoken by a raging erection trapped inside of the chastity cage that is too small for even his flaccid penis. His dick is in so much pain as it tries desperately to get free from the metal cage. Nick does not know how he will be able to sleep the rest of the night. But to try and get some relief he gets up and goes to the bathroom to take a piss. This does the trick for now and his erection goes down. But he is having trouble falling back to sleep. He finally falls asleep again after 20 minutes.

3AM: Nick is awake again. His cock once again fighting for its life to get hard. He is so frustrated he doesn’t know what to do. He goes on his phone trying to think of anything but sex to make his raging hard on go down. It takes a while but his dick finally goes down to a point where Nick tries once again to fall asleep. He falls asleep right away this time.

5AM: Nick wakes up a third time again from an erection. This time he is so frustrated and pissed off that he gets up and punches a hole in the wall. He immediately realizes what a big mistake he just made and that his dad will be so mad at him. He is now even more frustrated with himself. All he wants to do is sleep and now he has a cock that is trying to break free from a chastity cage and a hole in his wall that he knows his dad will be pissed off about. He wishes this were all just a terrible dream. But it isn’t it is a nightmare come true that will only go worse as the day goes on. He realizes he will not be able to go back to sleep since he can’t take his mind off of what his dad will think when he sees the hole in his room.

He tries to come up with a plan to patch the hole in his wall and then he paint over it. But he also realizes that he cannot stay in this chastity cage any longer. He decides that he will go to his dad in the morning and tell him that he needs to unlock himself.

At 7AM he gets dressed and grabs his keys. It is Saturday so he knows he will have some time before his dad will wake up. He drives to the home improvement store and gets a kit to patch his wall. He pulls into the driveway still assuming that he has plenty of time before his dad wakes up.

He walks in the door and is confronted with his dad standing right inside. “Where were you?” His dad asks, In a confrontational way but also somewhat friendly. Nick knows he cannot lie to his dad because he is has the bag with the patch kit in his hands. “I got so angry this morning because I kept waking up with an erection and when I was half awake I punched a hole in the wall.” Nick tells his dad. Joe says “I know I heard your car and checked your room, I am so disappointed how could you do this?”

“I just needed to get the anger out of me, Dad I’m sorry.” says Nick. “Well you will be sorry boy.” Joe tells Nick. Now Nick is scared. What does his dad mean by that. Nick goes up to his room and just sits for a minute thinking about what just happened and the events of the last 24 hours. He decides to just go tell his dad the truth, That the chastity cage is not helping him and he needs to be unlocked.

Nick walks downstairs to find his dad fuming. “Dad I need to be let out of the chastity cage I can’t take it anymore” Nick tells his father. “Do you think I care? I was trying to help you do something more with your life than just sit in your room and masturbate all day. I won’t be letting you out of that cage until I see some real improvement in your self control and your attitude.” Nick does not say a word and just walks upstairs.

Nick fixes the wall with the patch kit he bought. He thinks about what to do next with his dad. He is scared because he has never seen his dad like this before. Joe was not a strict father and was never one for punishment, and definitely not one for strict punishment like this. So Nick thinks it would be best to give his dad a little space and then apologize. Nick goes downstairs to make himself lunch and cannot find his dad. He looks outside and his car isn’t there. So he goes about what he was doing and makes his lunch. Around 4PM Nick hears Joe come in through the front door. Nick gives his dad a little time and then goes downstairs.

Joe is sitting at the kitchen table and Nick sits next to him. “Look Dad I’m really sorry about your wall. I snapped when the cage was interrupting my sleep and I was just so frustrated. I promise I won’t do it again”. Nick says to Joe. “Well I do appreciate your apology but some things have to be resolved with actions and not just words. So I think it is important that you learn a valuable lesson on self control. I think we should keep you locked in the cage for 2 weeks and see how we feel then.”

TWO WEEKS. Nick is infuriated but cannot let his dad know that. And he is wondering why his dad keeps using “we” when it is his penis they are talking about. But to keep the peace Nick agrees and says that will be good for him. Joe tells Nick that to support him he will also wear his cage for two weeks. This tells Nick that his dad 100% has worn a cage before. Because Nick cannot imagine anyone putting one on an voluntarily wearing it for 2 weeks straight.

Nick goes back to his room and lays down on his bed. All that keeps replaying in his mind is his father saying “2 weeks”. Nick thought that he would only be locked up for a day and now it is 2 weeks. How is any of this happening. It is just unbelievable from this and to some extent Nick still doesn’t believe all of this is happening. But then Nick looks down his pants and sees the biggest reminder that this is all happening. His cock locked up looking so helpless in the little cage.

He sits for about an hour not doing anything, Just thinking about the new reality he will have to go through for the next two weeks. No erections, No masturbation, No ejaculation, No release, Just complete frustration for two weeks straight. To Nick is sounds like it will never come to an end. He tries his best to forget about the cage by watching TV and playing video games.

Nick and his dad eat dinner together like usual and the mention of the chastity cages doesn’t even come up. Nick is almost glad because he hopes that when his dad has some time to think about it that two weeks is way to long to keep his son locked up. After dinner they watch a few episodes of a TV show and both head upstairs to go to sleep.

Nick is not looking forward to another night of waking up with raging hard ons that will torture him in his sleep. He showers and puts on boxer briefs and lays in bed. He strokes his cage up and down like he used to do when he had access to his penis. His cock gets hard in the cage and he actually likes it this time. He keeps stroking for a while but he doesn’t feel a release coming anytime soon. After another 10 minutes of stroking he stops as there is no point he’s only making himself harder. He thinks that maybe his dad is right. He knows he jerks off a lot but maybe he is truly addicted to jerking off. Its only been a little over 24 hours and he can’t control himself enough to take his hands off his dick even when its in the cage. He thinks maybe the cage will help but he wants to jerk off so bad.

He ends up falling asleep shortly after.

Day 20:

Saturday had rolled around again, and Brian had turned into a submissive, horny, desperate husk of a boyfriend. Everything revolved around a potential for pleasure, which meant it revolved around Jenna's pleasure, which was an absolute. She'd gotten busy at work which meant that she required more chores and more of Brian's tongue. As a further humiliation tactic, she said that she just wants Brian to find a way for her to sit on his face while she finished up some side work at home at her desk or when she was remotely working.

By Saturday, Brian had finished the little handy project and Jenna was able to wrap up some work while Brian's face poked through her seat as he lay down so he could lick her asshole. She laughed at how his time was best spent just under her ass all day. That was all of Saturday as she had gotten into the zone.

Afterwards, Jenna had Brian lay on the bed so he could eat her pussy to some orgasms. Brian realized he was so far into that submissive space, he'd not even considered his own orgasm. Thinking about this made him strain again in his cage.

Day 21:

Sunday was more errands, but a light day of it. When they returned during the afternoon, Jenna just wanted to chill and watch a movie with Brian. Brian, without asking, sat on the bed so she could mount his face like usual. But she shook her head.

"Today I want you to watch with me," she said with a smile.

Brian was shocked, but what further surprised him was he was almost disappointed to not be servicing Jenna in some demeaning way. He felt worth something under her ass. Pride was a distant shadow to him at this point. He could feel safe and purposeful without any fear of what he was doing with his life.

They watched some episodes of their show together before Jenna decided she wanted to shower with Brian.

Brian set up the shower to how she liked it. She removed her clothes revealing her beautiful body. What was also breathtaking was the lace with the key on it dangling between her breasts. Brian's jaw hung open when she entered in the shower with him and took off the key from her neck.

She shot him a knowing smile as she got to her knees and inserted the key into the lock. He froze, not wanting to get his hopes high. It was smart because Jenna did not turn the lock. She only stood up with he key still inside it and began to lather herself in soap, acting as if nothing had happened.

Brian just stood there, pretending his freedom wasn't so close.

After ten minutes of showering, Jenna took out the key, without unlocking him, and looped the chain around her neck again. When she was done with her rinsing off, she ordered Brian to turn off the shower so she could begin drying. Brian's heart sank and he returned to the bedroom.

After Jenna was done with her routine, she mounted his face so he could lick her asshole again while she surfed on her social medias.

Day 27:

It had been 14 days since his last "release." He didn't know when his next release would be or whether it'd be ruined or not. However, Jenna seemed to be in a bad mood that Saturday as work had been tougher than ever. Brian hadn't complained one bit, but he had to deal with her angst and was always inches away from having points deducted. Brian figured the points had been forgotten and now he really was at her mercy.

It did not seem like a merciful Jenna day today. She had him eat her out in the morning right away.

"God, I have to deal with the bullshit at work and you can just sit here dealing with only one issue," she said, rubbing her pussy on his face. "I am being attacked by all aspects and you get "attacked" by one. That stupid thing down there in the cage." She came hard and fast on his face, having ridden him so aggressively. She started up again. "I think it's unfair so I'll make it fair."

Brian did not like the sound of that.

Eventually, Jenna got off Brian and stormed off. Brian sat up and wiped his face, confused.

After a while, she came back with a strap on and Brian's jaw dropped. When had she gotten that?

"You're going to wear this," she snapped at him. "I need a real dick. Not yours. That thing will suffice. If you do a good job, I might reward you."

Brian immediately got to putting on the strap on. It was a sizeable 6.5 inches and Brian's cage felt all that much tighter as he realized after a month he was going to finally fuck his girlfriend. Just not the way he imagined. She got on all fours and presented her rear to him. When he was ready, he fingered Jenna's pussy to get it ready. He gasped as he realized it was oh-so ready.

He pushed the fake cock in and she moaned in pleasure. he didn't know her to love sex this much. Then again, he realized that might have just been him and his inadequacies. He began thrusting slowly at first before rising in speed. His own cock begged for release as its fake counterpart got all the warm, wet attention.

Jenna moaned and huffed with every thrust. Soft little gasps. "Uh Uh Uh Uh..."

This went on for about ten minutes before Jenna pushed him away. "You aren't good enough," she snapped. "Too gentle, too weak, too..." She made an irritated noise and gestured to the strap on. "Take it off and give it to me."

Brian gulped and obeyed. She began putting it on and Brian's heart skipped a beat. He was afraid, but also curious. Excited maybe? She snatched his wrist, yanked him onto the bed, and placed him onto his stomach. She mounted him and hit his ass hard.

"I need to vent my frustration out on you," she snarled in his ear. He heard a snapping of a bottle opening. Cold, wet lube dribbled into his ass and he let out a shiver and a moan. She snapped it shut, and began guiding the head of her cock toward his asshole. He whimpered again. "I'm not sorry," she said before sliding in her cock and taking away Brian's anal virginity.

It filled him up whole and his moan came out long and high pitched. It cracked off into a silent, gaping maw of pleasure and pain as Jenna began thrusting in and out at a faster pace than Brian could even manage. He couldn't speak or cry, he could just feel full as waves of intensity washed over him. He felt her hands push him down and her boobs graze his back as she rode him.

He realized he was just a play thing for her to vent her frustrations out onto. A new purpose. A new thing to deal with in life. Not just his horniness. Speaking of which, his cock wanted to burst out of its cage and a new fear got unlocked. What if he came like this? Would she EVER unlock him?

She continued to thrust and thrust and thrust until finally, even she grew tired after what seemed twenty minutes. Brian had been moaning dramatically the whole time and his throat had gotten dry. Eventually, Jenna slowly slid her cock out of his asshole and stretched.

"You can't satisfy me like that, Brian," she said, slapping her cock on his sore ass. She snickered. "Clean this up now."

Brian obeyed, and waddled as he walked to get the towels. She just gave him a smirk. he knew what it meant. "I just butt fucked you, bitch." His eyes flitted down and his cheeks flushed. he was so horny.

Not for the last time, he wondered when his next release would be. His cock strained in his cage until sleep took him.

My table of contents for not just the chapters of this story, but all the stories I have available and where to get them, updated daily.

This is a gender swap rewrite of the original femdom story, Lifelong Friends Become More

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Chapter 44

Kelsey trembled, knowing that Josh had not given her a full warmup on purpose so that Megan could enjoy her ‘delicious whimpering’ as she had put it. As rough as Josh had been with her the last time, she feared that Megan was going to greatly enjoy being just as rough, if not more so. She was so excited to get off the bed to fuck her. It served her fear, but it also served her submissive desires to see Megan so happy about it, the absurd large purple phallus leading the way.

“It’s so weird to walk with this thing!” Megan giggled as she came behind Kelsey. Kelsey stayed bent over even though there was no command to and no bondage holding her in a bent over position. She figured it was expected and it wasn’t like she could go anywhere if she straightened up. Even Megan at her size would be easily able to force her to bend over again. Her face rested on the mattress and she was ultra-aware of the cool air running over her ass. She felt very exposed and knew this was going to hurt. But she also knew she wanted it to, and wanted to make both of her dominants happy.

She could hear them talking softly behind her, but couldn’t make out what they were saying.

When Megan arrived behind Kelsey, still giggling over the weirdness of walking with the Feeldoe, she took Josh’s arm and pulled him back into the doorway and spoke softly. “How hard should I be? I mean, I want the sounds you talked about and I want to take her pretty hard I think, but I don’t want to be unnecessarily cruel to her. She is so wonderful, Josh and I can only dream of having such a perfect submissive of my own one day,” Megan said a little dreamily.

Josh smiled at the question and he knew how excited Megan was to do this, but he really also appreciated her caution and empathy for Kelsey. There was a fine line between a little enjoyable pain and being cruel, he knew just what Megan was asking. He was beginning to think about possibilities for this not just being a one night thing. There was nothing he hadn’t liked about this.

“You are being so wonderful with her too,” Josh replied just as softly, “I couldn’t have asked for better, and I really appreciate the care that you are showing. It really is tempting to just shove it right in and enjoy the power, believe me I know. But I think if you hold back just a bit to start it works out better. Even being gentle at first, you will still get those delicious sounds as you fill her, and you’ll also be getting used to the feel yourself. It lets her body start adjusting to it. I suggest penetrating slowly. Enjoy the sounds she makes as you slowly slide it in. I would slowly push in all the way, but then pause, just holding it there and enjoying it. Only after a few minutes, start to slowly thrust. She will make those sounds, I promise. Slowly thrusting will increase your arousal to the point you feel like you can not hold back any longer. When that happens, don’t hold back!” he said with a big smile and a laugh. It was how he had taken her last week, albeit from a different position, but he thought it best Megan started in a similar slow way. He was very curious how much physical pleasure Megan would get from it. This bent over position would add to her feelings of power too.

Megan laughed with him and put a hand on Josh’s shoulder, “Thank you, that sounds perfect. It is funny, I am so eager to do this and yet I am nervous. I don’t want to screw this up,” she admitted bashfully, for she too was thinking maybe they would invite her over again if things went well.

“You won’t,” Josh said, “I have watched you and I think you are just as natural at this as I am. You have the needed empathy, but not afraid to enjoy your dominance. Once you start, the nerves will vanish. When I did it last week, it was the best orgasm of my life,” Josh admitted, coloring a little.

“Thank you,” Megan whispered and then closed the distance to kiss Josh again. They lingered on the kiss for a few moments before pulling apart when Megan teased with a smirk, “my offer to take your ass is still on the table…”

She quickly turned then and came up behind Kelsey, running a hand over her still quite red ass. Her flesh quivered under her touch and her breathing hitched. “Are you ready to be filled by my big purple cock, kitten?” Megan asked in a pleasant tone as she took the tip of it and started to rub it against her well lubed hole. She was at the perfect height.

“Y-yes Megan,” Kelsey said softly, fear evident in her voice, as Josh came around and climbed onto the bed near her head. She started to stroke her hair, but his cock was still very hard she saw nervously, remembering what he had said about gagging her. With the way he had encouraged Megan to make her choke on it, she knew he would not hesitate in doing the same himself again. But what had most of her attention was the feel of Megan’s feeldoe rubbing against her asshole. Her imagination ran wild with what they talked about so softly leading up to this. She was sure that at any moment Megan was just going to slam it into her as hard as she could and she was terrified.

She felt the pressure from the head against her hole and tensed up even though she knew it was the exact opposite of what she should do. Megan didn’t slam it in though and to Kelsey’s surprise, she felt Megan’s hand caressing her back gently as she said, “Relax kitten, I am going to start slow, you are so very tight, you are all tensed up and I don’t want it to hurt more than it should. I promise I will go slowly to start, just relax. You look so amazing like this, you know. I have never seen such an amazing sight as you bent over for me as you are. I am so grateful to both of you and it would make me so happy to have you be the first woman I take like this…there we go. It is starting to slide in, you are such a good girl, just relax for me, you are going to love this. I can’t wait to cum just from fucking you…ahhh….” and the head suddenly went in and Kelsey whimpered with it.

Megan’s compassion and empathy had been so surprising, but they really shouldn’t have been. Megan hadn’t been cruel the whole night, even when she spanked her pussy while Josh licked her to orgasm. She had shown that she wanted to have as much fun as she could while still showing some care. Between her caressing hand, Josh’s continued stroking of her hair, and Megan’s amazing words, she relaxed more and more, wanting nothing more than to make Megan happy. She was turning out to be an amazing woman and Kelsey felt extremely fortunate that things were working so well, though she wasn't sure how much more after this she would be able to take without passing out.

Josh was also impressed with Megan’s actions just now, recognizing the problem as she tried to push into Kelsey, and taking the best course of action for all. The words she had used were absolutely perfect and would hit on all of the right buttons for Kelsey. Megan really was such a nice girl and the possibilities for the future were incredibly exciting. He continued to stroke Kelsey’s hair as Megan softly spoke to her, encouraging her to relax.

The whimper that Kelsey had let out as the head of Megan’s ‘cock’ slipped fully inside her made Megan shudder with pleasure. She started to push, ever so slowly, her eyes glued to Kelsey’s ass watching as her purple Feeldoe slowly started to disappear. She let out a moan at the way it pressed into her clit. She was so eager to start thrusting and feeling that over and over with the opposite sensation from the bulb inside of her on the outstrokes. But she needed to be patient. The payoff would be worth it.

And that was already starting. As it slid deeper, Kelsey’s whimpers got more frequent and higher pitched. “You are doing so good kitten,” Megan said, “Almost halfway there. God this is amazing,” she cooed as she kept the pressure on watching it slide in.

Kelsey started to make noises that indicated she was feeling pain, but they were mixed with moans too. Josh was not alarmed. Again, Megan was saying the right things and he could feel Kelsey relaxing more and more and sliding deeper into submission.

Finally, Megan’s small hips came to rest against Kelsey’s ass and she held there, completely filling Kelsey with her ‘cock.’ She continued to caress her back and call her a good girl for a few minutes. Kelsey continued to alternate between whimpers and moans.

Megan didn’t know how much longer she was going to be able to wait to start thrusting.

And hard…

​

This full story is already available to download from my website.

Sarah got ready for work as Justin sipped his coffee. She finished getting ready by dropping the silver chain with the key to Justin’s cage into her dress shirt. The chain was long enough to hide most of the key below her shirt but short enough to rest right between her perfect cleavage. Justin loved to see the keys nestled between his girlfriend’s perky breasts but was always worried about someone seeing them and questioning what the keys were for. Sarah hurried out the door on her way to work, shortly followed by Justin.

He couldn’t help but wonder about Sarah’s decision to wear his keys around her neck while she was at work and going to meet her new friend Abbie. But he brushed it off as he kept himself busy with the mundane tasks of work on a Friday eager for the weekend.

Sarah on the other hand was excited about the work day ahead of her. She couldn’t wait to see her brunette coworker Abbie and tell her all the details about how nervous her boyfriend was about meeting the “new friend” at the bar. Abbie was new to the office, and as Sarah’s desk mate they had become close friends during the short time they worked together. They had shared many details of their social lives with each other but hadn’t had the opportunity to hangout together outside of work. It was just a random chance to cross paths in the club the one night that Justin had made a risky bet.

Sarah had told Abbie of some of the kinky adventures she had with her boyfriend and was sort of a mentor to awaken Abbie’s sexual interests, obviously not knowing the pair would cross paths by chance. Now that Abbie had met Justin and seen first hand how the relationship dynamic worked in real time she was very intrigued. Abbie was full of questions for Sarah and couldn’t wait for the work day to be finished so she could ask all the burning questions over a bottle of wine. As the work day ended, the two girls made their way to the wine bar to talk about all the details of Sarah’s femdom relationship over Justin.

Justin had a normal Friday workday and hurried home to enjoy some alone time with a beer and grilling a steak dinner. He was nervous about his girlfriend’s meeting with their “new” friend but decided to not worry about it and focus on relaxing with the short amount of free time he had.

Sarah and Abbie, while enjoying a bottle (or two) of wine, talked about everything in Sarah’s relationship; how sex became boring, the tricks she used to spice things up, what worked and didn’t work, and eventually femdom. Sarah explained the power dynamic of the relationship and how she holds the keys to Justin’s manhood and how he willing gave up his own orgasm control. They talked about the games and bets they played together. Abbie was new to the kink scene but she quickly took interest and wanted to learn everything she could. Under the influence of the wine, Sarah invited Abbie to her house to show her the finer details of her relationship with Justin.

Justin received a text from Sarah, “Can you come pick us up from the wine bar? We had a bit too much to drink and I don’t feel like driving.”

Justin sighed before getting up off his recliner and grabbing his car keys and heading towards the wine bar.

Sarah and Abbie both climbed into the back seat of car before sharing a knowing look and giggling.

ALL CHARACTERS ARE OVER 18

Nick pulls his pants back up and sits down on the couch both in shock at what just happened and realizing what he agreed to. And then Joe says “Ok now I’ll put mine on” “No I don’t need to see that, Dad” Nick says. Joe tells him that he wanted to make sure Nick was really wearing his cage so it was only fair Nick got proof his dad was doing the same.

Joe pulls down his jeans, then his black boxer briefs. He takes the base ring and puts his balls through and then he lifts his shirt and Nick is shocked to see that his dad has a huge 4.5 inch uncircumcised penis. Nick assumed that since he was circumcised that his dad would be as well. Nick is looking confused how his dad will squeeze his penis into the small cage. But his dad starts pushing and he squeezes his penis into the cage. He locks the cage and collects both keys. Nick begins to wonder if his dad has had experience in this before because he did that so quickly.

Joe tells Nick that they should wear through to the morning and check back in with each other when they wake up. Nick had no idea that he would have to wear this while he slept. What about getting erect while he slept. Nick’s mind continues to wander as he wonders what he got himself into. It was at this moment that he realized this was going to be a march harder challenge than he had anticipated.

Joe puts the keys into a safe in his bedroom and the two of them go back to sitting on the couch watching TV. About an hour goes by and Joe asks Nick how he’s feeling. “It’s weird, I can forget about it for a few minutes but then I move and it feels heavy.” Joe asks Nick if he likes the feeling. “It’s not bad but I’ll miss being able to get hard.” Says Nick. “It’s okay, you will get used to the feeling of not being hard.” Joe tells Nick.

Nick is confused and wonders again if his dad has worn a cage before. Why else would his dad be telling him that he will get used to the feeling.

Now all Nick can think about while watching the show is what experience his dad has with chastity. Nick wonders if his mom had put his dad in a cage while they were still married. So many thoughts are spinning through his head that he can’t even focus on watching the show.

After a few episodes Nick decides to go get ready for bed and Joe stays downstairs watching more shows. Nick goes in his room as he hasn’t really even gotten a good look at the contraption on his penis. He goes in his room and immediately takes his pants off. He lifts up his cock and again feels like he has made a terrible mistake. He sees there is no way out and he already is gonna be looked up longer than he thought through the night. He is thinking about just telling his dad in the morning that he wants to be done wearing the cage. But he feels like he has disappointed his dad too many times that he does not wanna do that. He has to at least try for a few days to wear this so he doesn’t hear shit from his dad.

Nick gets in the shower and washes his whole body and he even forgot that he was wearing the cage till he went to wash his dick and remembered. After his shower he goes back to his room wearing just a pair of Under Armour boxer briefs and he lays on his bed and pulls up some porn on his phone. This is very typical for Nick and he even jerked off twice earlier that day but he is just so horny he cannot control himself. As he watches the video his cock begins to grow in the cage spilling out the sides of the metal cage. It pulls on his balls and he starts to feel pain. But he is so horny he just wants to keep watching the video but he knows it will only make him hornier since he can’t cum.

Since theres nothing he can do to release he decides to just go to sleep.

Day 1

Justin and Sarah had been dating for an awhile and their sex life had become a little boring over the years. Of course they loved each other but they were looking for something to spice things up in the bedroom. They experimented with all sorts of toys from handcuffs and new lingerie to exciting dildos, but the itch of something new always pulled in the back of their head. That’s when Sarah came up with the idea of changing the power dynamic, she wanted to try out being in complete control, and what better way to take charge than orgasm control. This started the couple down the path of femdom, which led to teasing and denial and in turn chastity cages.

Justin was hesitant at first but grew to like the teasing and psychological games Sarah played. The lock ups became more frequent for Justin and time between orgasm also became longer, until he was locked more than he was free. Sometimes Sarah would roll dice to see if he was allowed a release or if his time in chastity would be extended. Other times they would bet what color car would drive down the street next, to determine if Justin would be unlocked or if he would have to wait for another opportunity. Although Justin was always anticipating his next orgasm Sarah never went without, she would spend days or weeks teasing Justin’s poor locked cock, while he would give her countless orgasms either with his tongue or her many toys.

During a night out at the club Justin bet Sarah that she couldn’t get the next person to walk in to buy her a drink. If she failed she would unlock him for a blowjob if she succeeded he would stay locked for an extra 3 weeks. This was a risky bet for Justin because he had been locked for a week already, but he gambled on the fact that a couple or a woman would come in next. After a few minutes both their heads turned to the door as it slowly opened. Justin was elated to see a man hold the door open as a beautiful brunette walked through the door and take seat at the end of the bar, he knew it would be hard for Sarah to get a couple, with a jealous woman, to buy her a drink.

The brunette took a spot at the end of the bar and unfortunately for Justin the man went a different direction and found his own seat. Sarah gave Justin a devilish grin before she took the last sip of her drink and headed over to the new patron. Sarah took the stool next to the brunette and from across the room Justin knew Sarah was going to win the bet. The two gorgeous ladies now sat together, attracting the attention of the young male bartender and before long Justin could tell Sarah had just made a new friend. He didn’t know what Sarah had said but he watched as the two girls chatted and ordered a drink. As the bartender sat the drinks in front of the ladies they clinked glasses and looked over their shoulders and raised their glasses toward Justin. He knew that he had lost the bet and raised his glass to complete the across the room cheers in defeat.

Sarah sat next to the brunette until the drinks were finished before ordering another round and making her way over to Justin with the brunette following closely behind. As the new couple took their seats across from Justin, Sarah introduced her new friend as Abbie. The three sat and chatted over a few more drinks as the time passed. Abbie was as friendly as she was hot, her low cut top displayed plenty of cleavage as Justin struggled with the realization that he lost the bet and was currently being teased by his beautiful girlfriend and her new sexy friend.

As the time passed, Justin felt more like the third wheel as Abbie and Sarah’s friendship grew. As the drinks disappeared and the empty glasses stacked up the conversation became more flirty, closing time came and the girls hugged as the three left the bar.

Justin was silent on the way home knowing what the bet meant for him and his poor caged cock. Sarah teased Justin about the time that was added to his chastity sentence based on the bet that he had suggested.

“Abbie and I made plans to meet at the wine bar tomorrow after work.” Sarah said as Justin unlocked the front door to their home. “So you’ll be on your own tomorrow for dinner.”

ALL CHARACTERS ARE OVER 18

Nick is a 18 year old boy who just graduated high school a few days ago. Him and his dad live alone as his parents divorced and he has no siblings. Because of this Nick and his dad are very close but don’t talk much about sex or dating.

However Joe noticed when his son turned 14 everything changed and he seemed to spend a lot more time in his room. Joe would go up to knock on his door and hear him jerking off and walk away. Joe knew he was jerking off multiple times a day but he did not say anything. But now that his son was going off to college in 3 short months he didn’t want his son to be addicted to masturbating anymore.

Joe called Nick down just a few nights after his high school graduation and sat him down for a serious conversation. Nick and Joe sat at the kitchen table and Joe explained that while masturbation is healthy for young men that Nick does it too often and he is worried that he is becoming addicted.

Nick says that he thinks he jerks off a healthy amount. Joe responds saying that yes jerking off is completely normal and healthy but you still shouldn’t be jerking off more than 3 times a day.

Joe tells Nick that he has been doing research on this and has found a chastity cage. Nick’s eyes grow wide and he is confused and can only think of a chastity cage like a mid-evil times torture device. “No they are not made like that anymore Nick” Joe says. Joe shows Nick a picture of one online and explains that they are used to make men not be able to get erect or ejaculate. Nick does not like the sound of that

Joe explains to Nick that he could get 2 chastity cages and they could both wear one to try and help them with their self control. Nick is reluctant asking questions like, “Will it hurt”, “How long do I have to wear it for” “Will I be able to release every few days”. Joe answers these questions saying they will work together and try and push each other to wear the cages longer. But he says that if Nick needs to take the cage off for any reason that he will get the key out of the safe.

After hearing this Nick says yes mainly just to shut his dad up. The next day Joe orders two metal chastity cages in the medium size. Joe tells Nick that the cages will be here in 5 days and Nick knows exactly how he will spend the next 5 days. Nick continues to jerk off just as much as he normally does without hesitation. But he knows this will soon come to an end. He knows he has a problem but he lacks in self control to fix it.

He continues to jerk off multiple times a day until the day the cages arrive. Then exactly on time Joe knocks on Nicks door telling him the cages are here and they can put them on after dinner. Dinner goes by normally but Nick knows what is coming and he is so nervous.

After dinner they sit and watch TV for a bit and then Joe says “How bout we try on our cages?” Nick says ok and Joe opens the boxes. He pulls out the first one and sets it down. Nick picks it up and starts walking toward the bathroom and Joe says “woah what are you doing? You don’t even know how to put it on” “I’ll figure it out dad” Nick says. No come here and I’ll put it on for you.

Nick is in shock, His dad has not seen him naked in years. Joe takes the cage back from Nick and tells him to pull down his shorts. Nick pulls down his athletic shorts leaving him in his blue under armour boxer briefs. Joe is opening the package and then says “Well how am I gonna put it on with your boxers, Take em off”. Nick obeys and reluctantly pulls down his boxers revealing his 3.5 inch flaccid circumcised penis.

Nick looks at the cage and then his penis and says “I don’t think this will fit dad”. Joe tells Nick that you want the cage to be snug and it will be uncomfortable if it is too big. Nick takes his dads word for it.

Joe then says okay I’ll put it on now. He walks over to Nick and kneels in front of him. He grabs the base ring and delicately takes Nick’s smoothly shaved balls in his hands and places them one by one through the base ring. As he does this Nick is panicking thinking what have I done this is a huge mistake.

Joe pushes Nick’s balls all the way through and pushes the ring up against his trimmed pubes. Then he takes the 2.75 inch chastity cage and starts to put it over the head of Nick’s penis. “This will be a tight fit” He says to Nick. He starts to handle Nick’s penis rougher pushing the cage closer to his body. He finally crams Nick’s penis in the cage and connects it to the ring. He locks it in places and takes the key out of the lock. Nick is now bright red after just having his own father manhandle his package into a chastity cage. He feels so humiliated and doesn’t think it could get any worse. And then it does….

“Yes daddy, please fuck my tight ass.”

Those words bounced around in my mind. For a moment. I could believe I said them. But they left my mind as quickly as they entered once I felt his tip start sliding in. Because of the plug there was little to no resistance and quickly his whole cock was in my ass. Almost at the same time him and I both moaned with pleasure.

I felt both his hands grab my hips and I knew what was coming next. He started slowly thrusting about half of his length at first then steadily picked up speed until I felt his balls slapping against me. This was like no feeling I had felt before, it felt so much better than a dildo. Almost as if by instinct I started bouncing my ass on against him back and forth and I eventually felt him stop moving as I was doing the thrusting my self.

As I was bouncing back and he smacked my ass really hard and said, “yes bounce on my cock little slut. You were made for this, what a good little cock slut you are. Whose hole is this? Tell me whose hole this is.”

My mind was in a fog from the pleasure, I couldn’t even think about getting caught or anything other than his cock in my ass. I responded moaning, “this is your hole daddy only yours to use as you please. I’m your dirty little cock slut, I’m just a hole for you to fuck.”

He gripped my hips hard to get me to stop. He then started slamming his cock into my ass as hard as he could. I couldn’t control myself anymore, I was moaning like a cheap whore on his cock. Every thrust sent a feeling into my caged cock I had never felt before. I could feel an orgasm building but I wasn’t sure as I had never came in my cage before.

After a minute of him thrusting it happened. I started spewing cum from my caged cock. All over the sauna floor. This man saw it and said while groaning, “That’s a good little slut. You have no reason to ever leave that cage now. Not with daddy’s dick to make you cum. You came like a good little girl.”

The next few moments were a blur. I know he was still going to town on me but I don’t remember much other then the feeling of pure submission. This man could do whatever he wanted to me whenever he wanted. I was forever his little slut now.

What snapped me out of this trance was him grunting and saying, “Here you go little slut, here’s your reward.” I he let out a large grunt and felt his cock start throbbing and cum shooting deep into me. At least 6-7 thick ropes of cum filled my ass while he was grunting and slowly thrusting. He slowed down to a complete stop and slapped my ass.

Sounding winded he said, “You are the best fuck I’ve had in a while little whore. I’m here around this time daily, if I ever see you here I want that ass.” He pulled his cock out and I felt just empty I collapsed onto the sauna bench and he smacked my ass 1 more time and left. I laid there my face planted into the sauna bench ass still slightly raised just sore, used, exhausted. But also I never felt better.

Laying there catching my breath I remember what my wife said that she wanted proof otherwise I’d get locked permanently. I could feel his cum starting to leak out of me so I quickly grabbed the plug and put it in my ass. It went in with out any resistance but I knew it would keep the cum there.

I stood up and felt his cum move around in me. I almost fell due to how weak my knees were. I grabbed my towel and left the sauna. The locker room was empty but he was nowhere to be found. I didn’t even get to learn his name. I walked/limped over to my locker and got dressed. As I left the office I saw him out front talking to some other men. He looked at me, winked and went on his way. I went back to my car texted my wife saying I’m on my way home and drove home.

When I got home my wife was waiting at the door for me. She seemed almost like a school girl she wanted all the details. We sat down on the bed and I told her everything. I told her how he looked at me and invited me to the sauna.

When I explained how he had me suck his cock she smiled and said, “See all the practice paid off.”

I told her how he bent me over the sauna and made me ask him to fuck my tight little ass. I could see her getting worked up. She asked for more info. I told her how he fucked me, how he grabbed my hips and went to town. How every thrust I felt my manhood leaving and being more and more submissive.

I then told her how I came on the sauna floor from him fucking me. She gasped, “wait! Were you rubbing yourself or something, or did you cum solely from his cock.”

“Solely from his cock”, I said slightly embarrassed.

She laughed and looked at me. She opened her mouth and said, “well that’s almost proof enough you are in fact a little cock slut. But tell me more. Where’s the video or picture?.”

I explained how he kept fucking me and that there wasn’t a video or picture because he came in my ass. I got up and showed the plug still in me.

She screamed in delight and said, “You let a random stranger, a grown man, cum in your ass? Damn you are a bigger slut than most of my friends.”

“I didn’t really understand what was going on,” I explained. “Everything was kind of a blur after I came. Next thing I knew he was shooting inside me. Smacked my ass and called me the best fuck and he wants to do it again. Then left.”

She got up from the bed and said, “ bend over, show me the proof.” I got up bent over the bed and pulled the plug out. Cum immediately started leaking from my ass onto the bed.

She grabbed some of his cum that was leaking from my ass and rubbed it on me. “well he’s gonna get his wish and there will be plenty more of your sweet ass. Now come over here and lick my pussy.” She laid down in front of me and I licked her pussy, cum still dripping from my ass.

After she finally came she looked at me and said, “Just so you know you are never getting that cage off to cum again. Only for cleaning now that you can cum like a sissy.”

———

This happened a little over a week ago and he’s fucked me 3 times more. To this day I still don’t know his name. I’ve begun just calling him John.

When I arrived at the gym I got out nervous. Thought running through my head of getting laughed at for the cage, getting kicked out of the gym, what it would mean if I actually did this, and what would happen if I came home not having completed it.

I walked in and everything seemed just as normal. I went straight to the locker room and put some of my things in my locker and locked it. Now naked people in the locker room was not strange at all. I’ve seen many men walk around naked or even stand and talk naked. Even myself before the cage had walked around naked.

However, this time every naked person I saw felt just weird. I brushed it off as just being nervous. I figured while I was here I should still get a workout in. As I turned to leave I saw a man staring at me. He was about my height, white, with brown hair that looked like it was starting to grey. Bright blue eyes and he was maybe late 40’s to early 50’s while I’m 29. As I looked a little more closely I saw he was actually staring at my crotch.

I started to feel a little self conscious. “Did he know I was wearing a cage?” I thought to myself. “Nah I must’ve been imaging it.” I smiled at him and left the locked room and went to the treadmill.

I didn’t realize running with a plug in would be so uncomfortable but it in fact was. I resorted to some fast walking after 5-10 min of the discomfort. As I was fast walking and watching the Tv that same man came up to the treadmill next to me and started walking as well. I looked over and smiled and he smiled at me. I decided to look back at the screen and didn’t think anything of it.

After walking for about 30 min I left to go lift some weights. As I got to the dumbbells and started lifting I again noticed him nearby consistently looking at me. I again smiled and he smiled back while stretching. This continued on for most of my workout, everywhere I went he was also nearby making glances and smiling at me.

About an hour later I was done with my workout. I went back to my locker and checked my phone and saw a text from my wife. It read, “hey I hope it’s going well 🍆💦. If you haven’t had any luck yet try a shower with the curtain slightly open so if somebody looked they could see your cage. I doubt any man can resist a little caged fuck toy.”

After standing there rereading her text I thought to myself. “Fuck it, it’s gonna be done anyways who cares.” I took off my clothes going completely naked except for the cage and my plug and started to walk to the shower.

As I got near the shower not being seen by anybody yet the first person saw me. It was the man who was following me around earlier. He was naked as well and was quite hung. He looked at me looked down at my caged cock and smiled. I looked at him and realized that if I was gonna do this it would be with him. I smiled back and saw his dick starting to get hard.

I went into the shower right next to him and left the curtain slightly open. I turned on the water and started rinsing my body and cleaning off the sweat from my workout. Before to long I heard the sound of somebody clearing their throat and it was him looking at me from the crack in the curtain.

“Hey, I’m actually going to hit the sauna if you wanna join me.” He winked at me and I knew what he actually meant. I nodded and turned off the water and grabbed my towel following him over.

When we got into the sauna it was just the 2 of us. As soon as the door closed he looked at me and said, “I thought I saw that caged little dick through your shorts earlier. I’m so glad I was right. How long you been wearing that?”

I got a little shy and told him, “About 2.5 months currently. I’ve had it off for cleaning around it but other than that it goes back on.”

He reached out and grabbed my caged cock and balls and I felt a chill go up my spine. I’ve never had a man touch me before. He smiled with a look of hunger and said. “So how submissive of a toy are you? Gonna let me enjoy myself?” His words almost hung in the air I didn’t quite know what to say so I just nodded yes. This was the moment.

He almost growled and put both hands on my shoulders and lowered me down to being eye level with his cock. It was fully hard now easily 7 inches long. I just stared at it and knew what had to be done. I leaned forward and slowly licked the tip and the shaft. It tasted different than a dildo, a little saltier but also softer texture wise. I kept slowly licking but then I heard my wife’s voice in my head saying, “Suck it, suck it like it’s a man’s cock.”

With that thought in my head I took his shaft in my mouth. Swirling my tongue around and taking as much of it as I could. I heard him moan with pleasure and say, “What a good little bottom bitch. Oh I’m gonna enjoy this.” Hearing him say that triggered something primal in me. I started bobbing my head up and down almost like a pro. Taking all of his cock in my throat and just worshiping it. He was moaning in ecstasy and I felt my cock straining against my cage throbbing. I was leaking pre cum everywhere and grabbed some of it and threw it on his cock to taste.

After what must’ve been 5-10 min he pulled his cock away and said in a very commanding tone. “Bend over little slut. Time for daddy to have what he wants.” I got up without saying anything and moved to the bench in the sauna where I slowly started to bend over. It was at this moment he saw the plug in me.

“Mmm you knew what u wanted today didn’t you little bitch. Prepping that asshole for daddy’s cock didn’t you.” He said staring at my ass. He slowly pulled the plug out of me and started rubbing his cock along my ass crack touching my hole. Every time he did it sent shocks up my spine.

“Are you ready for my cock?” He asked. I nodded yes. He then asked again more commanding, “are you ready for daddy’s cock? Yes or no slut. Use your words my cock isn’t in your mouth anymore.”

I looked back at him as and said almost with a moan as he was rubbing his cock along my ass still. “Yes daddy please fuck my tight ass”

Part 4 soon

I awoke the next morning and got ready for work like normal. As my wife slept in bed I kissed her face and left for the office. It was a very busy day at work. When 5pm hit I was ready to go burn off some steam and that usually meant the gym. I drove home to get changed into my gym clothes. When I walked through the door my wife saw me and gave me a kiss on the cheek.

“How was your day my love?” She asked as sweet as ever.

“It was alright”, I said. “Pretty busy to be honest. I can’t wait to go get my workout done to relax and blow off some steam.”

She looked at me smiled and kissed my lips. “I already have your workout clothes set up on the bed for you. Go change so you can get over there and have some fun.” She said with a devious smile on her face. At this time just due to the craziness of work I had completely forgotten about what she said last night about me having sex with a man today.

I walked into the room and saw my workout stuff on the bed like she said. My shoes, a T-Shirt, shorts which looked tighter than normal, and… a butt plug. As soon as I saw the butt plug it i instantly remembered. I turned around and saw her standing behind me smiling.

“What’s wrong baby?” She said acting like she doesn’t know what I saw.

“Are you expecting me to wear that at the gym??” I said shocked.

“Yes I do.” She said in a firm tone yet still smiling some. “You told me you were going to prove how much you are a cock slut for me today. So you are going to wear those tighter shorts and that butt plug and search for someone at gym to fuck you. There’s gonna be plenty of men at that gym who want a taste of you.”

I looked at her a little shocked and said, “I’m supposed to just go look for some random guy at the gym to fuck? You never mentioned that!”

My wife looked at me and had a look of anger. She reached her hand down my pants and grabbed my balls quite hard. Squeezing them she looked me dead in the eyes and said, “You will do this or else I will throw the key to your cage away and you’ll never cum or feel my pussy again. Got it?”

For context my wife is 5’4 meanwhile I’m 6’3.

With her squeezing my balls I almost fell down to her eye level and gulped. I looked at her and said in a pained voice. “Yes Mistress.”

She released my balls and smiled. “Good now get ready and get that plug in. I’m gonna check before you leave.” She said as she turned and left the room.

I stripped down and went and grabbed the lube. I lubed up the plug and inserted it into my ass that was still a little sore from the previous night. I then threw on my shirt and realized my workout underwear weren’t there or anywhere to be found. Assuming she doesn’t want me to wear them I put on the new pair of workout shorts which were smaller and tighter than I normally work. I looked in the mirror and realized you could see the outline of my cage. Not a lot but if you were looking you’d know it was there.

I threw my shoes on and left the room and ran into her in the living room and she just smiled. “You look good babe,” she said looking at my crotch.

“I feel very exposed and people will know I’m wearing a cage.” I said feeling self conscious.

“That’s the point baby. But don’t worry only somebody staring at where your pathetic dick would be would know.” She then got up and looked at me closer. “Good no underwear like I planned for you, now show me you are wearing the plug.”

I pulled down my pants showing the butt plug and she smiled while smacking my ass.

“Now”, she said in a firm voice again. “I am going to want proof you actually did this since I won’t be there. You have 3 options and I will let you decide. Option 1, you can have the man fucking you take a picture from his point of view with you either sucking his cock or being balls deep in your ass. Option 2, I will accept a video showing the same things happening. Option 3, the man must finish inside you ass then you must immediately put the plug back in. I want that cum to be sitting inside you until you get home then I want to see it leak out of you.” She smiled at me as I stood there processing.

“So you want me to either let a man record me having sex with him or let him cum inside of me? I said puzzled. “I don’t really like either of those options.”

“Well too bad”, she said looking directly at me. “It’s either one of those or I never let you out of that cage again.

I nodded and left the house to head to the gym. My head spinning about what I was about to do, but also how was I gonna do it.

Part 3 coming soon

Some back story. My wife and I have always been open to trying new things sexually even before we were married. The only thing we’ve never done is opened up our relationship. We’ve recently been diving deeper into chastity and femdom which has now led to me being locked in chastity for 2.5 months roughly. During this time I have only been released for cleanings and have had 1 released orgasm about a month in. My wife pegs me almost daily. I usually go to the gym almost daily and with chastity it’s been hard but not impossible. I stopped showering at the gym however due to the fear of someone seeing my cage.

Now onto the story.

It’s about 9pm at night. My beautiful wife is laying on the bed completely naked legs spread open moaning. She opens her eyes and looks down on me as my face is buried in her pussy with her hand on my head pressing down keeping me there. The pleasure is too much and she moans loudly to an orgasm as her legs shake. Once she recovers she grabs me by my hair and pulls my head up away from her pussy.

“What a good boy” she says in a very sweet voice.

“Thank you Mistress”, I say. “Did I do a good job?”

“You did”, she replied. “Because of that I want to reward you. Come up here.” I crawl up and lay next to her as my dick strains against my cage thinking that I am finally going to be released for an orgasm.

When I get up to her face she says, “Go grab the lube so I can reward you properly.” As I get up to get the lube I hear her shuffling around and hear the familiar clicks of her Strap-on Harness. As I return with the lube I see her standing there sexy as ever with an 8 inch cock attached to her and holding a butt plug.

“Lube up the plug and insert it now.” She says as her tone has now changed from loving to commanding. I run over and squirt the lube on the butt plug ensuring a good layer then grab it and slowly insert it into my ass. I start to feel pleasure and my wife can tell because she just laughs.

Once the plus is completely entered and not going to come out she grabs me by my head and forces me onto my knees holding her cock 2 inches from my face. “Suck it.” She says in a voice that makes my caged dick strain against the cage even harder.

I open my mouth and start slowly licking the tip and the shaft of the strap on. Getting a feel for it again as this wasn’t the first time she’s had me do this. She looks at me with disgust and says, “I didn’t say lick it shrimp dick, I said suck it! Suck it like it’s a real man’s cock you are trying to pleasure.”

I took the cock in my mouth and started bobbing on it. Making sure to get as much of it in as I could but only could get about halfway. My wife then grabbed my head and forced it deep into my mouth where I felt it start to fill my throat. She held it there until I started to gag and then pulled it out so I could catch my breath as spit and drool feel from my mouth and the cock.

This continued for about 5 minutes then she pulled her cock out and told me to get up and bend over. I got up onto the bed and bent over on all fours doggy style. She smacked my ass and grabbed the plug slowly pulling it out of me. I couldn’t help but release a little moan as she did.

My wife smacked my ass when she heard me and I felt the cold lube get squirted onto my ass and rubbed into my hole. I then felt the familiar pressure of her cock pressing against my asshole. Thanks to the butt plug my ass was already loosened up and with a small push her whole cock slipped right into my ass and I moaned in ecstasy.

“Yea you like that little bitch”, she said as she slapped my ass and thrusted into me. “You know your worthless shrimp dick can never compare to this which is why I do the fucking now.”

She picked up the pace going balls deep with all 8 inches of the realistic dildo. As she continued to fuck me she commanded, “tell me you are just a worthless hole to get filled with cock.” I didn’t quite hear her over my moans so she gave one huge thrust and commanded again louder and angrier. “Say you are just a worthless hole just to get filled with cock.”

“I’m… I’m just a hole for cock mistress. I don’t deserve to ever feel pleasure from my cock again.” I said softly trying to compose my self instead of moaning.

“Good little cock slut.” She said as she continued pounding my ass. As she was fucking me she said, “Tomorrow we are going to test how much you really worship cock by getting you the real thing.”

My wife slowed down her pace a few minutes later and grabbed my caged cock that was dripping with precum. She took all that precum and rubbed it all over my ass then slipped her cock out of me.

As I laid there exhausted and with my asshole throbbing I thought back to what she said now that my mind was a little more clear and asked. “What do you mean tomorrow I’m getting the real thing?”

She looked at me with her big brown eyes and said in a sweet loving voice again. “Oh my sweet boy, you worship my cock so well I want to make sure it’s a genuine love for it. So tomorrow at the gym you are gonna find a man to fuck you.”

“But… but… I’m not gay?” I said still tired from my the pounding I just received.

“My sweet boy, you’ve already had a type of cock in your ass. I’m not asking you to date the man. I’m just asking you to get fucked by him.” She said as she kissed my head.

“I… I don’t know… I’d still be letting a man fuck me. I’m not sure how I feel about that.” I said starting to get up.

“Then I’ll make you a deal. If you let a man fuck you and prove to me you are a true cock slut. I’ll make sure you finally get an orgasm when you get home.” She raised an eyebrow as she said it knowing how much I wanted to cum.

It had been a month and a half since I’ve came and there was never any talk about when it would happen again. This was my chance to finally get a release. It would only cost me doing something she has already done to me many times. I looked at her took a deep breath and said, “fine… I’ll do it.”

Part 2 coming soon.

My table of contents for not just the chapters of this story, but all the stories I have available and where to get them, updated daily.

This is a gender swap rewrite of the original femdom story, Lifelong Friends Become More

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Chapter 43

“Aww, she is SO needy Josh. So desperate to be filled by cock like I just was. I wonder if maybe we could help with that?” Megan teased, getting up off the bed. She was glad that Josh hadn’t cum inside her because it would make what they did next a little more messy. She was on birth control, so she wasn’t worried about that. There was the fear of having the unprotected sex she was having with virtual strangers, and she really should have insisted on a condom for Josh, but she was too hot and bothered in the moment to even think of it. They were a very sweet couple and didn’t strike her as often engaging in risky behavior. Kelsey would be going to medical school next year and looking at her amazing athletic body, she obviously took care of herself.

Megan picked up the Feeldoe and squatted a little and worked the bulb between her labia. She finally started to work it in and it didn’t take much effort between how wet she still was and having just been thoroughly fucked by Josh.

“Oh fuck,” Megan said in a low humor filled voice as she started to stroke the new cock jutting out from her waxed pussy. It looked amazing and with how small her body was, it looked damn huge too.

Josh watched on in utter amusement as Megan picked up the purple Feeldoe, handled it with almost reverence and inserted it into herself. She was so damn cute.

Megan looked over to Josh and they shared smiles with Megan’s new cock jutting out from her, and Josh’s still hard cock. “Would you like me to return the favor Josh?” Megan teased. “Your ass I bet looks pretty amazing bent over!”

Josh laughed at the offer and how ridiculous it seemed as they had just been talking about fucking Kelsey. He had never once considered his ass as something to be penetrated by anything. He thought it might be time to make Kelsey a bigger part of the action.

“I am tempted Megan, and maybe we can later,” Josh said with a smirk that conveyed he meant no such thing. “But look at Kelsey’s eyes and remember how nicely she begged to be fucked? Although, I want you to try something. On the surface, it doesn’t seem like it would do much, but the power and the visual might be outstanding. Come kneel on the bed where I am if you would?” Josh asked, getting up.

Megan was still randomly laughing as she walked with the purple phallus jutting out, but got on the bed kneeling and facing the desperate Kelsey.

Josh came up behind Kelsey, wrapped his arms around her, and let his cock poke between the lips of her pussy. He said in a growl, “I want you to bend over and suck Megan’s cock and get it ready to fuck your ass. While you are doing that, I am going to make sure you are well lubed and if you ask very nicely, I will push my cock inside your pussy while I do so. I have a feeling Megan is going to fuck your ass pretty hard…” and he took his arms back, put a hand on her back, and applied pressure to bend her over the bed. He had planned this position from the start and it was why he had left her hands tied behind her back and her ankles tied wide. It lowered her ass enough that Megan would be able to fuck it from a standing position behind her. Josh had to bend his knees to line up his cock with her pussy.

Kelsey started trembling when Josh spoke in that voice. She recognized that voice. Full of domination and lust. It was the voice that meant she was going to be used hard. And based on what he said, it was going to be Megan let loose, but first, she had to suck her ‘cock’, and was scared enough of that. It looked so large sticking out of Megan’s tiny body and if she forced the whole thing in, Kelsey would definitely choke.

She did not resist when Josh pushed her torso to bend over, knowing what was expected of her. Megan was in the perfect position kneeling on the bed for her mouth to meet her ‘cock’. But the feel of just the tip of Josh’s cock bare inside of her drove her need through the roof. “Please Josh, I will be good. Please, I need your cock inside me so badly. Please…”

“I never would have thought of this!” Megan said excited, as Kelsey was bent over. “That’s right kitten. You got a pretty mouth. I want to see it wrapped around my cock…Open wide…” she said with a little giggle.

She watched in amazement as Kelsey did just that, closed the distance, and opened her mouth, taking in the head of the Feeldoe. “Oh shit, you are right Josh. Take it deeper kitten, I know you can,” she commanded, and Kelsey took in another inch and started bobbing on it.

Josh got the bottle of lube and thought Kelsey’s ass looked absolutely perfect like this. With how wide her legs were spread and bending over enough to get Megan’s Feeldoe in her mouth, her puckered hole was completely exposed and vulnerable. He squirted a generous amount of lube on his first two fingers and started to gently apply it to Kelsey’s hole. She was pretty sure Megan would be rather exuberant, so better to treat her gently right now, at least for the lube. At the same time, he slowly pushed his cock all of the way inside her pussy, causing her to make a muffled moan of pleasure around the Feeldoe.

On the other hand, Josh heard Megan ordering her to take more into her mouth. “Feel free to grab her hair and make her take more. The gagging and choking sounds she makes are adorable,” he said in invitation as he worked his second finger in her ass with more lube. He let his cock just fill her without any thrusting, though it was hard to resist the temptation.

Megan made a noise that could be interpreted as nothing but absolute excitement, took a fistful of Kelsey’s hair, and moved her hips forward until Kelsey started to gag. That only excited her more and she forced it deeper, though it still wasn’t the entire length. Josh looked up and saw and added, “That was about as far as I went with my cock too. I told her eventually she would learn to swallow the whole thing, but I think we need to work up to that.” He took another generous helping of lube and started applying it.

Kelsey was feeling so submissive and helpless and was in a constant heightened state of arousal. Even being forced to gag was arousing her. Megan’s easy control of her was very hot too. She tried to adjust, to not gag, but had little real experience with this kind of thing and struggled. On top of that, Josh filling both her holes was very distracting to help her concentrate on anything other than his cock and his fingers.

Megan let her come back off and catch her breath. She greatly enjoyed making her gag, but didn’t want to make her puke. “That makes sense, it will take time, still, you were right. Those sounds ARE adorable! Try to open your throat wider kitten. Yes, open your mouth wide, but also try to make your throat wider. There. Ready to try again?” she asked but didn’t wait for an answer as she pushed it in again. She managed to get another inch in before Kelsey started to gag again, and this time struggled to pull back.

“You panicked, kitten. You need to stay relaxed and just accept it in the future,” she admonished, and held her there a few moments longer.

“Well, her ass is as lubed as can be,” Josh announced, “would you like to switch spots?” he asked and slowly pulled his cock out of her pussy. Kelsey made little mewling sounds of desperation when Josh took his cock away.

Megan laughed with her desire but asked, “Are you sure? I thought you were going to take her…”

“I am sure. I want you to while she is tight and you can be the cause of her delicious whimpering. If she gets too loud with it, I’ll gag her with my cock,” Josh said with a smile.

Megan let go of Kelsey’s head, and almost jumped from the bed in her excitement…

​

This full story is already available to download from my website.

I couldn't help but tremble as we stood there, at attention in a line, holding our frilly little maid skirts up, revealing the tight, cruel, steel chastity cages we'd been kept in ever since Master brought us under his control.

He hadn't told us what he had planned for us, but it was clearly a special occasion.

"So, sissy cucks, I know that by now you'll all be feeling the frustration from those little cages of yours."

Masters voice washed over me, as I felt that overwhelming urge to submit like the pathetic little sissy Master had helped me realize I was.

"I believe I've made my opinions on chastity for sissy cucks very clear. A sissy cucks chastity should be permanent, without any form of release or pleasure to your little sissy clits."

A tremor ran down the line of sissies at his words. It didn't go unnoticed, as our wives and girlfriends shared looks and barely suppressed smirks as they lounged on the sofas together behind Master. How quickly he had brought them to his way of thinking. Whatever this was going to be, he wanted to make a ceremony of it.

"Unfortunately, it can never be truly permanent because of hygiene, medical appointments and other boring reasons. This means the sissy can keep some hope of being released from chastity, keeping them from truly accepting their position. Fortunately for you, I have a solution and I can tell you that after today you won't need those cages anymore."

Confusion now swept down the line as Master gestured to a tray to his side and lifted a cloth to reveal a series of small hypodermic needles, filled with a clear liquid.

"This treatment is to be injected into the base of your sissy clits, where it will render them even more useless than they already are. Your clits will shrivel and never get hard again for the rest of your lives. It will also remove almost all sensitivity, so you won't get any pleasure from rubbing them either. This is truly permanent chastity, with no hope of release."

Master picked up the first needle, barely giving us any time to absorb the enormity of what he'd just said, and approached the first sissy in line. Oh God, I was second in line.

"Tell me why you deserve this, sissy."

The sissy spluttered and trembled, still processing Masters words, but eventually managed to spit something out,

"Because I'm a failure of a man ... I'm a sissy and a cuck ... I don't deserve any pleasure ... I deserve to live my life in desperate submission to my betters”.

God, he was sobbing by the end. Master nodded, seemingly getting the answer he was expecting.

"Not bad sissy, but there's just one problem. You're talking as if this were a bad thing. See that's what I mean about sissies struggling to completely let go of their old delusions of manhood. For a man this would be a horrible punishment, but you are not a man. You are a sissy and a cuck. What I am offering you is to be permanently limp, denied and frustrated. The perfect state of being for a sissy. The ideal you should all aspire to. Understand that I don't expect you to submit to this treatment, I expect you to beg for it. So sissy, why do you deserve this?"

With Masters dominant gaze bearing down on him, something in the sissy cracked, as their old delusions of masculinity began their final death throes.

"Please sir... please give me the treatment so I can be kept limp and denied forever like a good sissy should. Please help me be a good sissy. I need it. I need to be good and obedient... I don't want to ever cum again... I don't want to ever get hard again. I need to be kept in my place as a sissy cuck forever”.

The poor sissy almost looked relieved by the time they finished and fortunately for them, Master seemed satisfied. He took the needle and gently injected it into the base of the sissy's clit just above the base ring of the chastity cage.

"There, all sorted. In an hours’ time we can take that cage off and you'll never need it again."

He turned to take another needle, and all too soon he turned his attention to me.

"Tell me why you deserve this, sissy."

Jonathan is a 20 year old on the college football team in January of his freshman year. Jonathan is a 6 foot 2 inch muscular man with size 12 shoes and a 4 inch flaccid and almost 8 inch hard penis.

Jonathan is a marketing major and applied for a few summer internships and he got accepted to the one he wanted. He told the company yes and they said he needed to do some paperwork for them, get drug tested, and get a physical and have a doctor sign off as it got closer to the starting date of the internship. Jonathan agreed and thought it was normal.

A few months go by with all normal communication from the Company to Jonathan. The internship starts on June 1st and on May 15th the Company gives Jonathan the doctor that must perform the physical and they also give him paperwork and where to go for his drug test. Jonathan agrees to this as it doesn’t seem like anything out of the ordinary.

Jonathan schedules the physical for May 29th at 5:30pm. Jonathan goes about his day normally, goes to his job being a waiter and a restaurant and then goes to the doctors office. Jonathan walks into the doctors office and it is a small office with only the doctor present. The doctor greets Jonathan saying “Hi Jonathan nice to meet you, I’m Doctor Schaeffer”. “Nice to meet you too” Jonathan says. “Follow me to the exam room”.

Jonathan follows Dr. Schaeffer to the exam room and he sits up on the exam table. “You can go ahead and get undressed and leave all your clothes on the chair over there” Said Dr. Schaeffer. Jonathan complied and took off all of his clothes except his white Calvin Klein boxer briefs. Jonathan goes back and sits on the exam table again while the doctor is on the computer. Dr. Schaeffer turns around as says somewhat stern “Underwear too”. Jonathan stands up takes his underwear off too and sits it with the rest of his clothes. After removing his underwear Jonathan exposes his 4 inch flaccid penis and his neatly tripped pubes and testicles.

The doctor rolls over to Jonathan and says “Alright Jonathan your here for a work physical right?”. Jonathan says yes. “Okay and your 20 years old?”. Jonathan says yes again. “Alright go over to scale i need your height and weight.” The doctor takes Jonathan’s height and weight and directs him to sit back down on the table. Dr. Schaeffer rolls on his stool over the table to ask Jonathan some health questions. The doctor asks Jonathan if he smokes, drinks alcohol, does drugs, masturbates, and is sexually active. Jonathan says no to smoking, drugs, and alcohol (even though he drinks often).

But Jonathan does say yes to masturbating and that he is sexually active. “How often do you masturbate? How often are you sexually active? How many partners have you had? and do you wear condoms?” Dr. Schaeffer asks. “I masturbate about once or twice a day. I have sex about once a day. I have had 16 different partners. And I use condoms sometimes.” Jonathan tells the doctor.

“Oh no that is way to much for someone as young as you. By the time your 30 you will feel no sensation left in your penis.” The doctor states. “Well how do I fix that?” Jonathan says. “I have a solution.” The doctor says excitedly. The Doctor starts puts a blindfold around Jonathan eyes and he freaks out. “What are you doing doctor?” Jonathan shouts. “Listen Jonathan, Do you want me to sign those papers for you? Or do you want me to tell them that you came to the appointment high and hungover so they will not give you the internship?” Jonathan thinks for a moment and remembers that this was the only approved doctor to perform the physical.

Jonathan sits down in defeat showing he will be obedient to the doctor. “Good boy, do as I say and you have yourself a internship boy.” Jonathan then gets blindfolded by the doctor and lets it happen but wonders why he called him good boy. Jonathan hears Dr. Schaeffer going through a drawer and he is confused. But before he knows it the doctor is putting something on his genitals. Jonathan jumps up but before he can say anything the doctor shouts at him “STOP, Do as I say if you want this internship.” Jonathan again sighs in defeat and lets whatever is happening happen. He feels something go behind his balls and over his penis and is very confused, then he feels something restricting go around his penis and then he feels a lock. Jonathan does not know what is on his penis but he doesn’t like it.

The doctor then takes off his blindfold and Jonathan looks at his pathetic manhood locked up in a chastity cage. “What is that Dr?” Jonathan says politely so not to anger the doctor. “That is a chastity cage, It is made so that horny men like you cannot get erect and most importantly can not have sex and masturbate.” The doctor says. “But why is it on my dick?” Says Jonathan “Because you use your penis way too much so for as long as I feel you need this on your penis it will stay on. And your company requires monthly check ups so I will be checking on your pathetic locked dick throughout the next month and probably much longer.” Now I will sign these papers and you will be on your way.” Says Dr. Schaeffer. Jonathan is just sitting naked on the table in shock but he just goes along with this so he get this good internship.

Jonathan puts his clothes back on and walks out with his signed papers that he needed. On his drive back to his dorm he can feel his dick straining against the metal cage to get hard and he starts to realize he will not being to do this for much longer. When he gets to his dorm he is happy his roommate is out for a while so he can try to get his cock free. After a half hour of trying the only thing he did was make his penis hurt even more. So he just gave up and tried to not think about it. This worked for a while but when his roommate got back to sleep he felt so horny and couldn’t do anything about it. He finally went to sleep and survived his first few hours of chastity.

Jonathan wakes by the pain of his dick trying to get hard in its cage. He wishes it was a dream but knows by the pain it is not. He gets up goes to the bathroom and his penis begins to try and not get hard as he goes on with his routine.

 Jonathan starts his new internship in two days which he is excited about but also wishes it was not happening at the expense of his sexual pleasure. 

 Because he is starting a new internship he is preparing today so he goes to get some suits. He goes to the store and tries some on and buys a few that he likes. He was so aroused in the store knowing his penis is locked up and nobody else knew. He then went to get some lunch and then he went home. 

 After playing video games for a few hours Jonathan decides he just needs to do things to distract him from his throbbing penis. He goes to the gym to work out and it does take his mind of it pretty well. After that Jonathan goes over to a friend of his house and hangs out with him for a while, Jonathan was scared his friend would notice but luckily they didn’t. Then Jonathan goes home and gets some sleep. 

 Jonathan wakes up again bright and early before his alarm from his throbbing penis that is not able to get hard. Jonathan now starts his internship tomorrow so he is started to get more nervous but is also excited and is doing some final reading up on the company and then at 1 PM he has to go into the internship just to sign his final contract now that he has had his physical signed off on. 

 Jonathan gets in his car and drives to the internship in a nice suit. He is nervous about anyone from the office seeing his chastity cage and thinking he was a creep. But he cannot help but wonder if the company knows that the doctor he had to go to is doing this to their patients. Jonathan signs his contract and then leaves so happy that he thinks he made it through with nobody seeing his caged penis.

 He then drives home and is so horny. He takes off his suit and starts watching porn, his dick is getting as hard as it possibly can but it just causes him discomfort. He rubs his balls and he starts to leak Precum. He really wants to cum and starts looking up ways to cum in chastity. He sees that you cum in chastity by anal stimulation. This scares him though because he is straight and has never done anything with his ass before. He realizes this will be his only option if he wants to cum, So he hesitantly Lubes up his pointer finger and inserts it. The feeling is new and very weird to him, He cannot tell if he does or does not like it but is making his penis harder. But he does not think this is going to make him cum. So he reluctantly orders a dildo that will arrive in a few days. He is so worried on how he will even make it a few more days with no release. But he has no other choice. 

Part 2 Coming Soon… Leave suggestions in the comments

My table of contents for not just the chapters of this story, but all the stories I have available and where to get them, updated daily.

This is a gender swap rewrite of the original femdom story, Lifelong Friends Become More

​

Chapter 42

Every time Kelsey thought they could not possibly tease her any worse, they came up with something new to tantalize her. She let out a whimper already at what was going to happen. Megan looked so damn hot on all fours in front of her, and Josh…crawling up behind her with large hard cock. He looked like such a God. She wanted to start begging now.

Megan didn’t waste any time, nor wait for Josh to start entering her, she flicked out her tongue and started to lick up between the folds of Kelsey’s labia. Her clit throbbed at finally getting some stimulation and she simultaneously moaned and whimpered. “Please…” she whispered in a desperate voice and Megan let out a giggle and continued to tease her pussy with her tongue only.

Josh was smiling broadly at what lay before him. Megan’s cute turned up ass and waiting wet pussy, and watching her tongue expertly tease his beloved. Kelsey was in such a desperate state that she was already begging and they hadn’t even really started yet. This was so much fun. Megan’s request had startled him at first, as he had been completely in the fucking Kelsey mind set, but this was not an opportunity to pass up. Megan looked incredible on all fours in front of him.

He rubbed the head between her labia and then started to slowly start working it in. Megan was plenty wet, but Josh didn’t want to hurt her, so he took his time in coating his cock with Megan’s wetness and working it in slowly, letting her get used to the feel of it. She was incredibly tight and Josh was going to have to concentrate not to cum deep inside her.

Megan let out a little squeak of pleasure feeling Josh’s cock start working into her. It was a respectable size, and she was glad he was taking his time. Knowing that Kelsey would be watching Josh fuck her made her quiver with desire.

Kelsey was in such a desperate state and Megan loved it. She would need to be very careful about stimulating her too much. She really wanted to clamp onto her clit hard with her lips and tongue, but she sensed that if she did, Kelsey would be cumming right away. That thought was arousing in itself, she wasn’t going to lie, but they might be doing so much more tonight, and Kelsey’s desperation was so delicious. Her arousal was like sweet nectar and she loved how much she strained against the bonds seeking more stimulation.

She flicked Kelsey’s clit with her tongue and Kelsey sounded like she was about to start crying. She was careful though to just lightly tease her. She didn’t leave her tongue there long, laughing at how Kelsey quivered. As Josh got more and more of his cock inside, Megan moaned and kissed down the sides of Kelsey’s pussy.

Looking up at Kelsey with a twinkle of mischief in her eyes, she very lightly placed her teeth onto Kelsey’s clit..

Kelsey did cry out at that. With how much fun Megan had at spanking her, both her ass and pussy, and with Josh getting closer to filling Megan’s pussy, Kelsey felt a huge spike of fear at Megan’s control and her teeth. Spanking was one thing, but she felt a real sense of danger now.

Josh was fascinated watching his cock slowly bury itself inside of Megan and hearing her make those lovely little moans of pleasure. He took his time, but eventually got it sunk all the way in while he saw Megan at Kelsey’s clit. Kelsey looked so scared and he understood why, but was also very much aroused by it. He started to grind his hips against Megan’s ass making his cock move inside of her and moaning. It felt amazing and he slowly started to thrust.

Megan knew Kelsey was afraid, and her fear added some delicious tension to the situation, but she was sure to be very gentle and careful. Even as Josh filled her pussy with his cock, and then started to slowly thrust, Megan was very conscious of what she was doing with her mouth. Once Josh really got going, she would stop with her teeth, but for now she was enjoying Kelsey’s fear and finally being filled by cock. It had been quite some time. Occasionally she would let her teeth very lightly graze her clit just to hear Kelsey whimper louder, but Megan had no desire to injure her. She was such a good girl.

Kelsey was sure that at any moment, one of those high pitched moans that Megan kept sending through her clit was going to end with her biting down, especially as she saw Josh start to slowly thrust inside Megan. She was so scared, her mouth had gone dry. This was the closest she had ever felt to using her safe word, but despite her fear, Megan had not hurt her with her teeth yet. The occasional graze of them would cause her a moment of panic, but it appeared she was doing it just to cause such a reaction. Ultimately Kelsey knew this was intentional and that both of them were turned on by her very real fear, and once again, their pleasure was what motivated her most.

Finally Megan took her mouth away, and Josh started to develop a more normal rhythm in his thrusts. Kelsey whimpered a sigh of such relief as her mouth came off her clit that both Megan and Josh laughed. She felt like she was constantly at the edge of cumming and Megan seemed to know that and never gave her enough stimulation to go over.

The sounds they made as Josh started to thrust in earnest were once again, so rewarding for Kelsey. They sounded so sexy and looked so beautiful. She was mesmerized watching Josh’s hips thrust in and out, knowing those same hips did the same to her and would again, probably tonight. She could see his abdominal muscles flexing and suspecting that he had fantastic control and stamina based on how he had fucked her so far and what was happening tonight. She could see the love for her in his eyes mixed with his dominance and pleasure as he fucked Megan.

Megan came forward with her mouth again and started to kiss Kelsey’s groin right in the spot between her pussy and her thigh, and then started to bite there, sucking the flesh into her mouth and doing her best to give her a hickey there. Kelsey whimpered louder at the pain and desire she felt and Josh moaned, increasing his pace. Megan’s body started to be moved by the thrusts, causing her bite to sometimes become more painful as she held on with her teeth.

The sounds both of them were making were becoming increasingly louder and they mixed in with Kelsey’s whimpers. Megan pulled her mouth off of Kelsey, leaving a nice bruise behind and yelled, “Harder!” and Josh immediately started to pound her hard. All Kelsey could do was watch as he fucked Megan to another shaking orgasm, Megan crying out in absolute pleasure and ecstasy as Josh thrust in one final time and both of their body’s shuddered.

It took them a few moments to recover and Kelsey started to beg, without knowing what she was begging for. “Please…oh fuck, please…I need….Please…” she was whispering over and over.

Megan finally looked up at her and laughed and said, “I do believe she is begging to be fucked too. Is that right kitten? Beg us to fuck you..” she commanded.

Kelsey didn’t hesitate, “Please fuck me. Please…”

​

This full story is already available to download from my website.

Just putting the final thoughts down to close out the boys trip weekend. Please read previous stories to get caught up, or don't.

Well, for those that have been in similar shoes, they can tell you how much your brain goes wild after extended periods of teasing. You, or at least I, tend to overlook at every single small detail. Sweating the small things. That's a story for tomorrow... and then W just went to sleep. How someone can fall asleep right away under these circumstances baffles me. But, that's one thing about W. Her head hits the pillow, and she's out for the night.

So, there I lay. Locked, aroused, teased, and most importantly, confused. What the heck had happened while I was away? While I normally hate the sleepless nights due to chastity, it wasn't the physical that was keeping me up. As soon as I'd find myself slipping into a slumber, a single thought would cross my mind. Did W actually fuck someone while I was away?

Now, as some background for those that haven't followed our journey, we play with others from time to time. However, with the exception of one event, we have never played with others and chastity at the same time. However, did that time open the floodgates? W and I have never really had the talk about playing alone, but I think there was a mutual understanding that things were naturally heading in that direction.

Before I knew it, I felt a warm, welcoming feeling as I slowly awoke. Wondering what time it was, I heard W softly whispering in my ear as she was caressing my body. Her hand rubbing my chest, down to my stomach, and eventually ending on my cage. 'Good morning, honey. I hope you slept good last night. Although, I'm sure your brain was spinning quite a bit.'

Uh, what gave you that impression... But, now isn't the time for any indirect responses. Thinking of how I wanted to broach the subject, I leaned over and gave W a passionate kiss. As we were kissing, I heard a metal-on-metal sound. 'Oh, thank god' I quietly whispered not thinking W could hear me. But, a muffled laugh let me know she had heard my emotions turn into speech.

Cage is off, and W starts stroking me. First physical pleasure in four days at this point. Sadly, I could already feel an orgasm brewing. But then, W started again whispering to me in my ear.

'So, about those condoms...'

'Yes, tell me about him. Tell me what you did while I was gone.'

'Are you sure that you want to know? Or do you want to just keep this memory as whatever you've mustered up in your thoughts?'

'No, W. I want you to tell me all about him. Spare no details. I've been thinking of this all night. I didn't even sleep last night I was so horny'

And, this might be the part where some of you are upset. Again, the theme with W is the mental aspects of chastity. She likes to play games, build things up. And with that, I couldn't believe what came out of W's mouth next.

'See, the thing is I did want to fuck someone while you were gone and locked up. But, I didn't really know how you'd like it. Would you love it? Drive you over the edge and melt away into your chastity brain? Or, would you want to keep the play with you there?

Holy... shit... she's done it again. I started to reply, but she cut me off right away.

'Now, the way I see it is that you liked what you thought had happened. Now, next time you go out of town I won't need permission. You've told me all I need to know. I figured as much, that's why I bought the big box of condoms'.

And with that, I started to spray cum all over the place. Wiping the cum from herself from my collateral damage, she whispered:

'I guess more confirmation of how much you want me to do it, H'

My table of contents for not just the chapters of this story, but all the stories I have available and where to get them, updated daily.

This is a gender swap rewrite of the original femdom story, Lifelong Friends Become More

​

Chapter 41

Kelsey had moved her hips forward so that Megan could reach her, and now, with her small pushing into her, she didn’t dare move back again. If she even tried, she got the feeling she would be made to regret it. The discomfort was building in time with Megan’s pleasure and the noises she made. It wasn’t long before Megan rotated her hand and brought her thumb over Kelsey’s clit and started to rub it hard. Kelsey started to whimper and that seemed to cause Megan to moan louder and go harder. As her pleasure rose, she increased the pressure on Kelsey, causing her to whimper more loudly, giving Megan more pleasure…

It was one of those spirals that just kept making things deeper and deeper. Kelsey was being over stimulated, but she loved it, even though she wasn’t sure she could orgasm from it. She loved that she was helpless to do anything about it. She loved watching these two incredibly sexy and beautiful people enjoying each other and at the height of pleasure. And finally she loved that her discomfort turned Megan on more and showed her dominance over Kelsey. She felt so submissive, and was glad that she could have this small part to play in Megan’s pleasure.

Josh heard Kelsey start to whimper and then more loudly, but couldn’t see why. He didn’t know if it was just from being helpless and watching the display before her, or if Megan was doing something to cause it. It didn’t matter to him too much though, and he wasn’t all that concerned. If it was something she couldn’t handle, she would use a safe word. He recognized those whimpers and the delicious sound of them and they turned him on now just as much as if he was the cause of them.

Megan hadn’t let up on his cock, no matter what else she might be doing, and Josh didn’t let up on her clit either. He knew she was getting close and by the cute noises Megan made, and he felt his own building, but was going to hold it off for as long as he could. As their pleasure increased, so did the efforts of their mouths and tongues.

Megan was getting close now, and in part due to what she was doing to Kelsey with her hand and the noises it caused. Doing 69 with Josh in front of Kelsey was hot enough, but she also found it kind of ironic that while she and Josh were reaching the heights of pleasure with one another, Kelsey was helpless to do anything but watch her pleasure her man. She felt so powerful and so happy. Kelsey was absolutely perfect with how willing she was. She had been surprised but pleased that Kelsey had moved her hips forward in order to help her. What a good girl. Those sounds she made were so wonderful and as Megan’s pleasure crested, she got rougher and started to spank Kelsey’s pussy hard.

Megan cried out in orgasm and Kelsey to her noises by crying out in pain and ecstasy as the pain from Megan’s spanking hand radiated out on her pussy. She was happy to experience it though.

Megan’s orgasm was incredible to see, and so was the endorphin-fueled pain that Kelsey felt, but as Megan started coming down from it, she finally let up on Kelsey’s pussy. She didn’t take her hand away, instead she gently caressed it, almost in thanks or apology over what it had just endured. It actually felt incredibly nice and Kelsey moaned softly as Megan continued while rolling to the side and freeing up Josh.

Josh sat up and then flopped on his belly next to Megan so that both of their heads were near Kelsey now. Josh put an arm around Megan as they both caught their breath and said, “that was incredible Megan.”

“I know, right!?” Megan replied with a giggle. “It was fucking amazing. Thank you so much…fuck…I was expecting to swallow your load at any second.”

Josh laughed with her and replied, “I don’t want my part in tonight’s activities to end too soon!” Then he looked up at the moaning Kelsey and Megan continued to casually and gently caress her pussy. “How was it for you baby?” he asked.

“It…it was incredible. Beyond words really. To see how much pleasure both of you were having was really quite amazing. I feel so fortunate to have witnessed it, thank you,” she said sincerely and Josh had to remind himself about these dynamics again. Sure she was sexually frustrated by watching and not participating, but her top priority was always, without fail, HIS pleasure. And in this case, Megan's pleasure too. So by that perspective, she had received a lot of pleasure too.

"I hope you don't mind Josh," Megan said, "but I gave her pussy some attention during that, and as we orgasmed it might have been a little too hard, based on the noise she made."

That explained the whimpers and Megan's gentle attention now. "Oh not at all. She is fine and her whimpers added to it for me. Did you mind Kelsey?"

"Not at all. I was happy to suffer for your pleasure," Kelsey replied simply.

"I loved doing it," Megan said. "Made me feel so powerful and you are right, her whimpers were amazing." Megan then looked up at Kelsey and said, "you did a great job kitten. Thank you. Does what I am doing now hurt?"

"No Megan, it feels really nice. There is a little lingering soreness, but the gentle touch helps," Kelsey replied.

"Good. I want it to feel good," she said and continued to do it as she turned back to Josh and asked, "when it is okay with you, can I see the strapon?"

Josh’s eyes sparkled at the question. “Of course!” and he jumped out of bed and opened the closet to pull out the box. He didn’t know why Kelsey had a strapon, but it wasn’t really important. It was too good of an opportunity to pass up. He found something called a ‘Feeldoe’ and looked up at Kelsey questioningly. She nodded and shivered. He pulled it out and then walked casually back over to Megan to hand it to her. Megan took it, almost greedily, very excited about it.

“Fuck, this thing is amazing! I mean, it is silicone obviously, but I love the way the skin is still soft to the touch and then how hard it is underneath. So this is double ended? I have never seen a shape like this…” Megan said, turning it over in her hands and occasionally stroking up its length. Kelsey looked on quite nervously, but knowing there was a very high probability that Megan was going to take her ass tonight, and probably not gently.

Kelsey spoke up, “Yeah, I guess it is kind of like a double ended. The bulb part goes up inside you and …there is nothing quite like when you are thrusting and can feel that bulb rubbing against your g-spot. The little ridges there?” she said, as Megan turned it and looked near the curved bottom of it, “they rub and press against your clit as you thrust in, and then as you pull out the bulb presses against your g-spot. I have never felt anything like it…” Kelsey said a bit embarrassed and red faced.

Both Josh and Megan looked at her in surprise and knew this was a story for another time. Megan bit her lower lip and said, “As much as I can’t wait to use this, I have a question to ask. I know we are kind of winging it, but…after all that oral…I could really use a dick inside of me. People sometimes hold PIV sacred, so I wanted to ask both of you if it would be alright for Josh to fuck me?”

Josh’s cock surged at the idea of fucking this cute little redhead, but she was right, people sometimes viewed that differently and he had no desire to upset Kelsey.

“It is up to you Kel,” he said. “I fully understand if you wouldn’t be comfortable seeing that or don’t want things to go that far, and I won’t be upset if you say so.”

Kelsey looked at both of them and knew she belonged entirely to Josh, but as he had said, her goal tonight was to serve them both equally. And the thought of watching Josh fuck her was an arousing one. She wouldn’t lose him to her just from a fucking. Their bond was way too strong for that.

“It…it would make me happy to see Josh fill you up and give you pleasure,” Kelsey responded, her chest heaving a little. Both Megan and Josh smiled broadly.

“I’ve got an idea,” Megan said, and climbed back on the bed on her hands and knees until her face was inches away from Kelsey’s pussy. Her ass was facing the headboard. “Josh, I would like to try edging Kelsey, but I would love it if you’d consider fucking me with your amazing cock?” she asked.

Josh broke into a big smile and climbed on the bed behind Megan and would be able to look Kelsey in the eyes as he fucked Megan and Megan edged her…

​

This full story is already available to download from my website.

This is my time writing, please leave some feedback, I do have a couple more story ideas

Freezing water poured over me as I stepped into the shower with a gasp, thankful for the reprieve from the torture I had endured.

“Goddess’s edging regiment is becoming too much to bear” ran through my mind as my raging erection subsided.

She required me to record and send 7 edges a day; and of course whenever she wanted to amuse herself. And she wanted me as close to the edge as possible. If my cock wasn’t throbbing and leaking when I let go, she wouldn’t count it. I had learned my lessons quickly.

My musing was interrupted by an incessant buzzing from my phone on the counter. I was going to leave it but my curiosity got the better of me, I leaned out of the shower to grab my phone and my jaw dropped. Goddess was video calling me! I answered as soon as I realized what was happening.

The simple black hoodie she wore did nothing to diminish her beauty. A flicker of disapproval flashed through her eyes as she had spoken.

“Is this any way to greet your Goddess pup?”

I dropped to my knees in the freezing water and began to apologize when she silenced me with a single finger.

“let’s not ruin the moment my sweet puppy” she murmured in her exotic voice. “I have something for you. You’ve been so good recently I thought you deserved a treat.”

As I knelt there, shocked, she lifted the camera up revealing that she was wearing only panties. My raging erection returned with a passion despite the freezing water. She began to rub over the fabric lightly as she stared at me intently.

“Would you like to see more pup?” She asked teasingly while slipping a finger inside.

“Yes please Goddess! I’ll do anything” I pleaded “please please please Goddess."

She smiled lustfully, opening her mouth to respond when there was a knock at the bathroom door.

“Are you okay in there?” Came my mother’s voice. “It’s not normally so loud in there.”

“Yeah everything is fine” I started to say when my Goddess interrupted me.

“Let me talk to her.”

My heart stopped and I gazed at her with a silent plea. To please have mercy. Her response was a simple; “now slave.”

I stood up trembling and approached the bathroom door.

“Hey mom, someone wants to say hi.”

I was going through every interaction with Goddess, trying to think of anything that might have displeased her.

“Your son really is quite funny. I really enjoy talking to him. He is very entertaining!”

I sagged against the wall as my knees went weak. Goddess talked with my mom for several minutes before saying her farewell and ordering me back to the shower.

“Kneel” she purred, one finger pointing down.

I obeyed instantly as she stood up and stepped out of her panties. Sitting back down she held the camera close to her glistening lips.

“See how wet you made me pup?” She moaned as she slipped a finger inside.

“Such a good boy. So obedient.”

My hands drifted to my cock as I watched Goddess please herself. I should have known better.

“Not a chance” she laughed “hands behind your back until I finish."

Flushing red with embarrassment I did as ordered, and remained on my knees with my hands behind my back as she had a powerful orgasm.

“Well that was fun.” She said cheerfully as she blew a kiss goodbye.

“Send me a photo of you in your chastity cage within five minutes. You’ll be in it for a while pup. After all, you’ve been so good for me.”

[M37] [F34] An honest and detailed look into our relationship dynamic, and description of what she does to/with me. Hopefully some find this a refreshing change from fiction. All of this is 100% true and no embellishment needed. We have been together for 2 1/2 years, “practicing” a chastity lifestyle on/off for the last 2 years, after I shared my desire to be denied and controlled by her. The first few months were clumsy, finding the right cage, finding how it worked for us, things like this take time and are what make a great sex life. Anyway, on to the fun stuff!

I typically wear my cage 2 weeks on, 1 off, this past October was my first straight month of having no choice in the matter and only off when she said. It was amazing, and June will likely be another “locktober”.

When I am locked, it is understood I do not and will not cum for 1 week, longer if she decides. While in the cage I am not allowed access to keys unless there is an emergency, we go on bike rides together, swimming pool etc, everything day to day the cage is on, including work and even showering, 24/7. The only time the cage is allowed off is when she says, we have an “hourglass” that is a 2 1/2 minute interval, if I am good and she is feeling I deserve it, she will let me jerk off for one flip of the hourglass, two flips if she is feeling generous, and sometimes she will give a handjob for this time, if I’m lucky. These times with the hourglass turn me into a dripping mess all week.

If she wants sex, she gets sex, she gets as many orgasms as she wants, I am not allowed any, and the cage goes back on, absolutely no cumming for me until Saturday. If I lose control, I lick up the cum, which I desire before cumming but not after, like most. During lockup period, I give her oral many times, I love eating pussy, and I love going to sleep knowing I’ve given her multiple orgasms and my cock remains locked.

I love receiving anal play, and during lockup I am allowed at any time to play with my ass, it provides me a lot of relief when I get very “full”. She will often tell me it’s time for me to put my butt plug in, usually if she says this I know my cage is coming off for sex, she loves feeling my vibrating plug through my cock inside her.

She is very open minded, and the idea of pegging was well received. The first time we tried it I had been locked for 9 days beforehand, I was a horny leaking mess. She was surprised how it made her feel and I had my first caged anal orgasm ever on this night, I will never forget this for the rest of my life, it was truly amazing. Luckily I am a fairly attractive and fit man, she finds my ass sexy and this isn’t just something she “does just for me”

Some things she likes to do during lockup. Sometimes she will promise I can cum on Saturday, and during sex, right before I bust, she tells me Sunday instead. The first time she did this it was unbelieveable. The scenario was wild, I struggled to put my cage back on and was a leaking horny mess. I decided to go out for a ride on my motorcycle to clear my head, this was the first and only time I have ever actually cum in my pants. I was on a side road about 5 miles from home and the vibrations of the bike took me over, I tried to pull over in time to let it subside but I ended up blowing a giant load inside my riding pants. It was truly humbling and a humiliating ride home, we had a huge laugh about it and it’s a story for the books for sure.

Sometimes, she promises I can cum, and she keeps her promise, but the cage has to stay on, and she will give me her vibrator and watch, she loves watching this and says my struggle is wildly intoxicating and satisfying for her.

On another occasion we used wrist cuffs tied to my butt plug, she took my cage off and gave me a 30 second long blowjob, allowing me to cum in that timeframe, the pressure was too much and I wasn’t able to. After She said I was still allowed to cum, but not allowed to touch my cock. After mercilessly humping the bed and rubbing my cock on the dresser I failed. My cage went back on and I had to wait until the next day.

I can add a part 2 of our ongoing shenanigans if anyone would be interested.

Also, AMA.

Who knows how long me and Beth have been locked in our separate cells I made the best of it and got some rest. As Beth spent most of her night In frustration attempting to get some relief in her aching vagina. I am sure Angela and Silver are somewhere watching the show on camera.

It is the next day when a long table is brought into the room by Angela and Beth’s servants. I am brought out of my cell first and brought to the table. The table has a whole in the middle of it and hinges open I am sat kneeling as the servant closes the table around my neck trapping me in place. I hear Beth being brought out of the cell and hear the open and close of the table as I assume she is in the same situation as I am.

Another fun item is it feels like I am straddling a Sybian as well and I am seeing a dial built into the table on my end. The servant starts bringing out food and sitting in front of me as I hear Silver and Angela talking as they enter the room and sit down. Silver at my end of the table and Angela on Beth’s end. I hear Beth start to moan and I hear a slight hum as it sounds like Angela has turned on Beth’s Sybian.

Silver starts to eat and feeds me as well breakfast is fresh eggs, bacon, sausage , pancakes, and orange juice. I am enjoying my food when Silver turns on my sub Ian as well now as we are eating you can hear the low hum and moans coming from both me and Beth. As we are finishing up breakfast the intensity increases as it sounds like Beth is getting close to orgasm after her long night of frustration.

The table is moving slightly as I assume she is bucking her hips trying to help herself over the edge. It comes as a screaming orgasm I hear Beth finally getting her release as Silver turns my Sybian up higher and now I am pushed over the edge as well filling the cum running through the tube in my chastity belt and filling my as hole with warm goo.

Angela and Silver wet not through with us thought the Sybians stayed turned up as I could hear Beth’s moans of pleasure while we both built up to our next orgasms. Silver gets up and leaves my Sybian running. She comes back to me with a pair of vr goggles and puts them on my head.

It’s a camera that is setup in the room and I can now see mine and Beth’s predicament like I’m watching a porno. Angela is setting up Beth with a pair of goggles as Silver makes her way to the middle of the table and pulls up a strap on. Silver bends Angela over the table doggie style and starts pounding away on her pussy with the strap on.

Silver pounds her for a few minutes I am able to watch the whole show and fell the table moving with every thrust. I can see Silver is pulling Angela’s hair using like a handle to get maximum depth with the dildo in her pussy. Angela moans as her head snaps back with every thrust. Silver rolls Angela over onto her back and start pounding away as she wraps her hands around Angela’s throat.

Angela is gasping for air as Silver is still pounding away. Mine and Beth’s orgasms have finally built as well when we both start screaming with pleasure. Angela starts her orgasm with me and Beth as she is still struggling to breathe she starts convulsing from her orgasm and passes out. Silver releases her at the moment she passes out and holds Angela for a moment as she starts breathing again and regains consciousness.

At this point me and Beth are in trouble as it fells like a continuous wave of pleasure coming from the Sybians that are left running as Angela and Silver swap places. Silver starts on her knees sucking Angela’s juices off of the dildo before making her way over to Beth. Silver is now face to face with Beth licking Beth’s lips so that Beth can taste Angela’s pussy on her lips.

Angela had moved behind Silver and is now pounding away in Silvers pussy as Silver is stuffing her tongue down Beth’s throat intensifying the orgasm Beth is now having watching Angela pounding Silver from behind. It’s not long before Silver is having her own orgasm. Right as Silver is going over the edge Angela pulls back on Silvers hair and starts slapping her ass pounding away at Silvers pussy til she falls limp from the intense orgasm she has just experienced.

They shut off our Sybians as silver grabs a piece of bacon from the table with her arm draped over Angela’s neck she takes a bit and feeds Angela a bite as the leave the room advising us they will be back after they have a shower.

My table of contents for not just the chapters of this story, but all the stories I have available and where to get them, updated daily.

This is a gender swap rewrite of the original femdom story, Lifelong Friends Become More

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Chapter 40

Megan turned to him with a huge and warm smile and they kissed again in agreement before getting up. Kelsey also got up, but there was no move to uncuff her hands and she was left to follow them into the bedroom. Once there, Josh took control and said, “Kelsey, for now, I would like you to stand at the foot of the bed, facing it, wil your legs spread please.”

This was new, but she quickly did it. Josh took the box of toys out of the closet, which he still hadn’t fully looked through, and grabbed rope. Since they had bought a four post bed, not only because it looked nice but also for its practicality for bondage, there were two feet at the bottom of the posts as well. He attached the rope to her ankle cuffs and secured him to those corner posts. Her legs were spread very wide and she wouldn’t be able to go anywhere. With her hands still tied behind her back, she was quite helpless and vulnerable. He reached between her legs and grabbed her pussy firmly. She moaned with her desire. He laughed and patted her red ass before going over to Megan.

Megan, despite knowing why they had all come in here, had felt a little awkward in their private bedroom space. But she was fascinated watching Josh direct where Kelsey was to stand and then tying her there. She couldn’t help but wonder why he had chosen her to be like that, but giggled when he reached between her legs from behind and grabbed her pussy.

Josh came over to her then and she forgot all about her nerves as Josh gently cupped her face and kissed her. As before, the kiss was soft but becoming more urgent and passionate. Their arms wrapped around each other and they started to lose themselves in the kiss once again, until Megan escalated it a bit further by letting her hand trail down and run over Josh’s ass.

That broke the floodgates and they both started trying to remove their own clothing and that of the other simultaneously, while still kissing as much as they could. There were several laughs and some clumsy moments, but eventually they both ended up fully nude with their hands all over each other.

Megan was surprised by Josh’s body and how sexy he was. He had just the right amount of body hair, his thigh muscles were developed and thick, leading up to a firm ass. And his cock, mostly hard, was great looking and a bit on the larger side.

Similarly, Josh enjoyed exploring Megan’s tiny body. She wasn’t out of shape either and her body was just perfect with its freckles and proportions. He was fascinated by her breasts though, as both nipples were pierced and had a bar through them. It looked so fricken hot and he kept running her thumbs over them. He would need to talk to her about them later as they would look amazing on Kelsey too.

Josh gently guided Megan to the bed, and they lay on it wrapped in each other's arms, kissing with their hands roaming.

Right in front of where Kelsey stood.

She whimpered. She couldn’t move much, and they were mere feet away, their perfect bodies entwined. His cock was so hard and beautiful and it made her so aroused to watch. Their heads were at the head of the bed on the pillows, but it gave Kelsey a perfect, unobstructed view of them. She could only watch as they made out with and explored each other. Sometimes they were side by side facing each other, and other times one or the other would be more on top as they rolled around. Their desire for each other was clear though, even as they sometimes softly laughed. Their fingers found each other’s genitals and gently ramped up both of their arousal.

They paused for a moment and Megan, actually looking like she was blushing a bit, said a little shyly, “I…I want to taste your cock. Do you mind?” as she was looking into Josh’s eyes.

“Mind? Fuck no. I would love to taste you as well,” Josh said, knowing it was true. Several times now he had come very close to just doing so, but he was not dominant over Megan and he wasn’t sure he wanted to be. He loved being dominant, especially with Kelsey, but this felt so much different. He had no desire to be submissive either.

Megan giggled at the answer, and then asked Josh to lay on his back. Desire plain, she got to her knees and then swung one leg over Josh’s head while she faced his feet. And Kelsey. Josh spread his legs wide, giving Kelsey an amazing view of his cock and full balls before Megan’s head came down on it and started to lick at the tip. They had neatly moved into a ‘69’ position with Megan on top.

Josh almost couldn’t think with how hot this was as Megan swung her leg over. Josh was greeted by the cutest little pussy with yet another piercing through her clitoral hood. He felt Megan’s tongue on him just before Megan lowered her pelvis and Josh tasted her pussy for the first time. And he loved it as Megan sucked in the head of his cock and started to play with his balls with a hand. He moaned and inserted a finger into Megan as he sucked her clit into his mouth.

Megan again started to make those high pitched noises with her pleasure as Josh’s tongue went to work. This was so different from how Kelsey had done it. Not that Kelsey had been bad at it, she had in fact been excellent and she wasn’t sure she would have had her change anything. Just the fact that it was the boyfriend of the girl tied in front of her added something to it.

Josh had much the same feelings. Kelsey was absolutely wonderful at giving head, and he would never stop enjoying her mouth, but there was something added with this while also doing it himself that made it almost otherworldly. Poor Kelsey, he thought, she probably wasn’t aware of just how much trouble she was in later with how this foreplay was affecting him and Megan. She did have a wonderful view though. As did he. He greedily sucked Megan’s clit into his mouth wanting more of those amazingly cute noises she made.

Kelsey felt like she was going out of her mind with arousal and the fact that Josh had obviously planned, by tying her up like this, to put on a show while she could only watch, aroused her even more. She actually couldn’t see all that much from where he was. Josh’s face was hidden by the curve of Megan’s wonderful ass, but she could see Josh’s cock disappearing into Megan’s mouth. It was an amazing site to behold. And to hear. Just the sounds they were making alone made her feel like she was about to cum.

The biggest thing though was how much pleasure they were both in. These two wonderful, dominant people that she wanted nothing more than to please, enjoying each other in pure pleasure. That alone turned her on more than anything.

Their sounds of pleasure were starting to get louder, and just when Kelsey thought she was going to remain completely excluded, Megan stretched an arm toward her. And it was a stretch. Kelsey assumed though that she wanted to touch her, so she pushed her hips forward as far as she could so that Megan could reach. She moaned and whimpered as Megan’s small hand touched her pussy.

But it didn’t take long for Megan to push two fingers into Kelsey roughly.

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This full story is already available to download from my website.