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On my second try in many months I finally completed a poor makeup job. But once I got eyeliner and eyeshadow on and threw on a blonde wig, there was this attractive woman staring back at me in the mirror. I am not like a 9-10 attractive man, and also middle aged and starting to show some wear. But I can't believe how good I look as a woman. I could not stop posing and taking pictures of myself. I'm frightened at how hot I'd look with a proper makeup job.

So I ordered a new cage online, but im not sure if it's going to be too small for me. When I looked at the sizes, it said my size, but I looked at the page again and it seems like it's like 40mm smaller or something. Can my clit get that small? Or is it going to be a pain?

While he touched my clit I came into his hand 🤣 He started with touching my ass and biting my nipples. Then I came when he touched my clit and afterwards I gave him a blowjob.

I guess thats a moment when I realized that I might be a sissy..

Ok babes, time for some lingerie shopping, looking for recommendations and links to purchase!

I just tried everything I could think of, can anyone help me on how to cum my own face

[Continued from a morning as a sissy with two men and a woman in their apartment...]

After I left the apartment I sat in my car awhile and browsed Grindr and Sniffies. I chatted to some guys but nothing was going to happen right then. I was still plugged and caged and had been all morning while I got a seeing to, so I was horny and wanted using. So I went to a cruisey toilet block I knew nearby.

There were three stalls and the one in the corner had someone in it with the latch showing it was occupied, but the door still ajar. I've done a little bit of cruising, but I'm not experienced, and not bold, but that was signal enough for me to press the door open. A guy in there had his cock in his hand, but he immediately shut the door again. I think he was working up the courage. I sat the in middle stall next to him and waited and tapped a little in his direction, but he didn't react.

Quite soon another guy came into the stall on the other side. We tapped to each other and he stuck his face under the divider and I motioned for him to come around into my stall. He was maybe 50 something and had a lovely mushroom head cock. He was turned on by my cage and started roughly finger fucking my pussy. He was hitting my prostate and lots of juice flowed from my clitty and I moaned loudly. He pulled his pants down and I got on my knees and greedily sucked his cock. He came very quickly and I drank it up. He smiled and mouthed 'thank you' and left.

I waited in the stall and chatted on Grindr some more. That first guy in the corner stall was still there and I motioned under the divider to him, but he didn't react and eventually he went out.

I was about to do the same when another guy came in. At first I thought he was not cruising, but then there was a shoe tap. I tapped back. I was looking under the stall divider when I noticed he was looking over the top. He was very tall and handsome and young and hot. I went around to his stall. His cock was long and hot. Honestly, he was just about an ideal of male beauty. I got on my knees and reached for his cock, but he moved away. Instead he walked out of the stall and stood out in the bathroom while I stayed in the stall. He was standing there jerking his cock. We were the only ones there, but people were coming and going pretty regularly. He was obviously enjoying the risk.

I decided to get into it. I was in the stall. I showed him my caged clitty and he hardened up and got stroking. After lewdly flicking my nub around I turned around and showed him my pussy hiding behind my thong. I pulled that aside and slapped it with my fingers. Quite nervous and listening for the door while he watched my fingers start spreading my cunt for him. He whispered hoarsely 'More!' so I stuck two then three fingers in and fucked myself with them, then four (I can easily take a fist).

I started to put fingers from both my hands in and pulled them apart so that I was making my hole gape wide for him. I thought he surely must want me to jerk him off or to fuck my mouth by now and I made to do that, but he pulled away again. Okay, so he just wanted to jerk off to me. Fine. He told me he wanted me to take my shorts all the way off, probably to enjoy the extra risk, so I did.

I had my bag with me and it was half open so I quickly put on my little velcro mini skirt - I was instantly more girly and slutty. Here I was sissied up giving this hot man a show he wasn't going to forget in a dicey situation. It was very excited. I kept pulling my pussy around. He whispered 'Push it out.' So I pushed out and my slick red rosebud went out towards him. A bunch of air loudly came out, I guess from the tunnel plug I'd been wearing earlier in the day. He loved it and groaned loudly and jerked faster.

He asked 'Got a dildo in that bag?'. I pulled out a butt plug, the smaller of the two I had there and put some lube on it and my pussy, rubbing it around saucily for him. I said I took out the smaller one, but it wasn't small - this was about 3 inches in diameter. His eyes grew wide. I pushed it into my pussy and spread my cheeks wide for him. I fucked myself with it for about a minute.

He moaned and he started loooking at me a little confused, like, how could this be happening? How did he walk into a cruisey public toilet and get this sordid slut show? Well, he hadn't seen nuthn yet. I got out my Monster Egg Plug (Square Peg Toys, can recommend) again blowing this guy's mind with what my pussy could do as I put it in and then fucked myself with it. I did this and kept showing him my gaping ruined pussy between plunges.

Finally I put it in and pushed the butt plug out hard, shooting it out towards him and it went bounding along the floor. He said 'Oh you are such a dirty little slut!' and that sent him right over the edge. He came. Great big gobs of cum flying across the room towards me and splashing on the floor as he kept jerking his cock and sending more into the air. I turned around and caught a splash on my fingers and ate it.

He gave me a long look, but said nothing, cleaned his hands and went out. I cleaned myself up and got into my normal clothes, then I left.

Later I came back and sucked off another guy while I wore a dress. He wanted to fuck me raw and I was tempted but refused. He came in my mouth and ran out of there. Then I finally went home.

I've been playing with my pussy since forever, but came to dressing up and sissy stuff much later. I like to do sissy tests and have done plenty of kinky stuff, but one regular question I would lose marks on was 'had sex while dressed as a sissy'. Yesterday I had a free day and, with butterflies in my stomach, put some gear in a bag and looked around on Grindr.

I found a m/f couple online a few hundred metres away. They'd never been with a sissy and said they weren't very kinky but they were fascinated with my pictures. They were hanging with another guy at his place and wanted me to come around. I still wasn't sure so I warned them I might flake. They were nice about it and tried to put me at ease. I got myself clean, kept my cage on, put in a butt plug, and fished out a frilly red thong with a girly little jewel at the front, then got in the car and started in their direction. I told them I was coming to see them. My little sissy heart was pounding.

I was not femmed up out on the street so I think he had to adjust for a moment when I met one of them outside their apartment block. He was wearing a red t-shirt. We went up. The scene was a bit sordid. A small apartment, darkened with a blanket over the window, smell of pot. Gay porn playing on a big tv screen. The woman, wife of red shirt guy, was in a negligee. The other guy was wearing a jock strap and white t shirt.

No one made any moves. I said I'd go and get dressed. I put on my slinky red dress, my red high pull up socks, and my wig. I wasn't even close to passable, but I thought I did look hot. They thought so too. They were still a bit shy too so I went and lay on the bed, spread my legs a little and showed them my panties and my cage. Took them awhile to notice my plug. They asked a lot of questions. I was reticent. I regret that - I think next time I would talk openly about my interests to better connect and so I'd more easily get into a subby space. They put on some music and I danced for a couple minutes, being slutty about it. I tried to commit but it felt awkward.

I think the jock strap guy was usually bottom with them, but seeing as a bigger slut had shown up he sat on the bed and waited for me. I took his cock out of his jocks. It was uncut and had a nice curve, maybe 6 inches. I went slow, licking around the head. He immediately had precum and I greedily licked it up. I felt his cock hitting the back of my throat and had recently read about a sissy making a guy wild by making his cock head fuck the narrow back of her throat, so I did that. He liked it alot. He wasn't naturally dominant, but he started to press my head onto his cock and I moaned happily.

The red shirt guy took awhile, but he came and sat on the bed too. At first he didn't want me to touch his cock. He got me to lick his balls. He was trying to talk in a dominant way but he wasn't great it. But then he slapped me in the face a bunch of times with his hard cock. It was probably about the same size as the other guy and a bit less shapely, but it when I took it in my mouth it felt good.

They were both sitting at the head of the bed and I went from one cock to the other. When I took their cocks right to the hilt and gagged a little it would make my clitty gush a little leak into my panties. I fucking loved it. The woman stood at the side of the bed. Red shirt guy told me to fondle and lick her breasts, which I did gladly. I was attracted to her too and wanted to eat her pussy but she said no.

It was a small room and a warm day with four of us in there and I was working up a sweat. My hair was all over my face and stuck to the sweat there and I was starting to get messy and feeling sluttier. I told them I wanted them to fuck me. I wanted to take it raw but had run out of PrEP and couldn't risk it, so I put a condom on the jock strap guy. He tended to mumble, but he ordered me onto all fours and told me to spread my pussy, which I did. It felt vulnerable and hot. He spit on my pussy. The woman was close and watching us. Then he pressed his dick into me and sunk it all the way in. I moaned and arched my back for him. He took my hips and he started getting a rhythm up. The red shirt guy came to the foot of the bed and I took his cock in my mouth so that they made a spit roast out of me.

The jock strap guy kept on boning me and I started to talk dirty about how much of a slut I was and how much I wanted cock. I asked them to put both their cocks into my asspussy (I can take a bit back there), but they wouldn't do it. I worked the man's cock with my pussy, sometimes pushing out at him and spreading apart, sometimes trying to gape for him, and sometimes clamping down on his shaft.

The red shirt guy and his wife went over to the couch, she lay on her back with her pussy towards me and he mounted her and I watched them fuck while I got fucked. The two of us girls taking dick like pros. But he lasted about 15 seconds and came in her. I asked to clean her up but she said no.

Eventually the jock strap guy slowed down and I was exhausted anyway, so he stopped. I went and put in a bigger butt plug with a tunnel. I put my ass up in the air while I sucked his cock again to show them how slutty and vulnerable I was. The woman was cooing appreciatively. She kept complimenting me on my legs. I sucked his cock for a while and stopped for a rest just lying there flicking my caged nub around, then I sucked him again. I gave it my all but it seemed like he wasn't going to cum so I let it be.

We sat around for awhile. I had a yearning to be more dominated than I had been, just handled and used a bit. But the vibes were winding down and I had the sense that, fun as it had been, these three weren't ready to really put me in my place. I went into the bathroom and got out of sissy outfit, though I left on my panties, cage, and plug. We said some nice goodbyes and I left.

Every upvote this post gets I'll ride my new dildo for 5 minutes. Every comment means I'll sit balls deep on the dildo for 10 minutes. Help me be a submissive sissy.

I was born biologically male, now 30 years old. I've been changing into women's clothes since childhood. I stole a lot of clothes from my mother and sister, then I started buying my own. After high school I decided to go to work as a firefighter because I'm a man, I didn't want to admit that it could be any other way. But the older I got, the more feminine I tried to become. I got my belly button pierced, then my nipples, then I got a feminine tattoo around my thigh. I've been on vacation several times, spending it all as a woman. Now I'm wondering if I should start living life as a man, try to start a family, stay with my job as a firefighter and live a normal life despite the fact that my girly self might come after me. Then there is the second option and that is to start living as a woman, start my transition, start taking care of myself and live my dream life as a woman, but that would mean leaving my job, leaving my hometown (I don't want my family to know about my change, because they don't support it and I don't want to hurt them). But I'm afraid that it would be a step into the unknown, that I won't be happy and I'll be alone, but on the other hand, I think that it might be the best decision of my life. And I need to decide, I can't put my two pages together. Anyone have any advice please?

P.S. I'm already 30 years old, I don't have time to wait.

What kind of lubricant or cream do you use after playing with your dildo to relief some pain if you had it?

I've been crossdressing for a while and would like explore this side of me more and since I haven't done anything other than wear girl clothes and then jerk off, I'd like to experiment. I suffer from post nut clarity as well but since no nut november is coming up, I should have 30 days to test things as long as I don't fail. I stopped purging clothes a while back but the shame still remains. So what can I do to get started and what are some goals I should set to achieve?

I’m a sissy (or still in the process), but I’m still heavily attracted to women. Can I still be considered stat straight as a sissy, despite all the ‘gay’ ideologies behind it? Just wondering

Thanks :)

Genuinely curious, no judgement. How was your experience? These aren’t cheap … did you find it worth it? What would you do differently?

I’m expecting most may not share, but perhaps there’s a few lurking on this subreddit that can share what the session was like, and things like logistics and picking which dominatrix, etc.

When your horny all the time and your wife has low libido/ is very vanilla. And you can go out to find a guy but it can't be all the time due to you not wanting your wife think that you don't love her

Yup. I am incredibly sexually frustrated at the moment. where I just want my holes to be used and abused and be humiliated and be that adventure couple in public where she makes me go out in fem at night and shit. But sadly she doesn't role that way.

I love her to death and I would never do anything to harm this relationship. I just wish she stops being so vanilla. And there's no talking her into anything because as soon as you bring stuff up she's the type of person that thinks i just want sex and blah blah blah. And yes but damit I want to do fun shit

Just wanted to rant and share.

I saw a tweet today by user @TSPrincess_Jane that was bashing the use of the word sissy and referred to it as “gross”. I know we have some trans girls in here. Are sissies disliked in the trans community?

So I have felt and embraced femininity for years. I have cross dressed (infrequently and always secretly) since a teen and have always loved it. Over the past 20 years I have indulged in my feminine nature more, at least when alone, and have accepted to myself that I am more feminine than I am masculine. I would love a romantic relationship with a man, but I see so many posts about wanting to be degraded and humiliated. I want to be romanced, cherished, kissed and held. I want a man who wants me for who I am and will make love to me, not just fuck me. So my question is, are there any others in here who feel the same? And…am I a sissy? A pre-trans trans woman? I know label are not the end all and be all, but I am trying to come to some clarity within myself just who I am.

So I impulse sized up to a lovense hush 2. Being silly as I am I don't quite realise how large the 1.75 inch one really was in comparison to what I used. Anyway 4 failed attempts over a week or so to get it all the way in and I managed it yesterday (yayyyy).

So once it was fully in I occasionally got waves of like a cramping sensation. It was like heavy pressure not pain exactly. Anyways had and fun and then came the moment that I felt like I couldn't get it out 👀. That would have been a fun explanation.

My question, has anyone experienced this sensation before?

I’m scared but I really want to have my first dick ☺️ how do I push myself to actually do it

For me, he would be:

• around 40-50 years old
• little to no body hair
• average cock (I normally would want an average or smaller cock for oral and a huge one for anal, but he can't have 2 cocks)
• has a belly
• is not conventionally attractive
• cums buckets
• he's kind, fun to talk to, and is protective of me
• he is confident in bed and gets what he wants, without being pushy or aggressive
• a bit kinky, but not too much; he is mostly a guy with sexual urges and wants me to satisfy them

If here is any cis-woman, I want to know what do you think about clitties? Even during sissy sex with alpha, our clitties are just hanging there ignored, useful and feminized. Are they cute to you or gross? I am just courious from your point of view on all of this. Thanks 🙂‍↔️💞

But I need to eat more pineapple. Anyone have any favorite sissy snacks for changing the flavor of your cum?

Hey lovelies! 💖

Femboy Blackmail Cult https://www.youtube.com/watch?v=mME0NXRQHuc

🌸 Curious About Online Communities? 🌸

I just watched a YouTube video about a 4chan community helping force boys to transition, and it got me thinking! How do online groups influence our big life decisions? Have any of you been inspired or guided by these digital spaces? 🤔

Would love to hear your stories or thoughts! Let’s keep it light and supportive. 🌟

xoxo 🌷

I just bought my first butt plug snd oh my gosh is it amazing. I love to use it as a dildo too which feels amazing when my ass is open and lubed up. I would definetly recommend for everyone to get one!

I want to be fucked by a man and I want to give a blowjob. I'm 20 and have had these fantasies for two years. I would actually like to do it so much and let men dominate me. But my problem is that I don't find men attractive. That's weird and sounds stupid, I know. But I don't know why it is like that and what I should do🤷‍♂️ Maybe one of you has an answer to this and knows what I should do?! I would be grateful for answers and help in the post or via DM🙏 Thanks❤

My first Locktober is a success!

This month has been an incredible journey. The euphoric experience of staying locked for over 30 days has been intoxicating.

I’ve decided to continue into No Nut November. Maybe I’ll just end up perma-locked…. 🥰

So yesterday I posted about my wife making me her sissy and screaming to her I’m your bitch and I just want to be your bitch so bad after being locked up for 6 days while being her sissy. Well…. She had to go to work shortly after so I was left home with a few sissy task like picking up the house and laundry while dressed up. I had to go to the grocery with my sissy clothes under and then the last was to use my big pink dildo to practice hands free cumming since I hadn’t accomplished it yet. So I get everything situated standing so I could sit down on it and record me being a good sissy and completing my tasks. It felt so fucking amazing after I finally got it in. I began to slowly take it deeper each time and I could feel it hitting my spot. So I relaxed even more and I stopped the video cause I could feel it coming and when I sat down a little further right after ending the first video to try and get it on camera, it happened! My very first sissygasm. Cum started leaking out my locked away clit and my legs began to shake as I tried to catch what I could on camera and showed her the mess I had made on myself and in the floor. I had never been happier accomplishing my first ever sissygasm. It just confirmed to me even more that I am indeed her sissy and forever want to be her little bitch.

Hi. I really love wearing buttplugs, wanted to hear if someone has expirance wearing them 24/7 for extended periodes whats to pros and cons.

Ever since exposedrealfun discord has shut down I am unable to find a group where you can chat with doms/sissies who are into exposure. Do you girls know any such groups?

I know there is r/exposedsissies and r/blackmailers however it's not quiet the same as those groups, where you can find so much content and contacts with other doms/sissies.

Hi all, I have crossdressed with girly dresses at home since my teenage and I'm addicted to the feeling these dresses provide. But since I'm moving out for town for work, I'm in a situation to buy my own girly dresses. This is my first time to buy a new bra and panty. I'm confused with size saying cup 32D, 30C something like that. How can I choose the correct size for me. My chest size expanded would be 43inch and hip size is 33inch, currently using inner size 75cm.

1.What size bra and panty should I choose? 2. How can I approach the shop/Shopkeeper to buy this girly dress items since I'm a boy?

Any experienced person here, kindly advice me.

I wish lovness or one of those remote control companies would make a dildo machine that can wirelessly pair with a Fleshlight, then. Have a service where you can go on their app and look for guys who wanna have sex with you remotely. Or you know, just turn on "slut mode" where aslong as it's on anyone can freely pair up with you and use you.

Maybe even have it be able to tell if you're actually their, ooo maybe also some feedback so if you say squeeze the dildo, the Fleshlight also squeezes the guys penis