/r/Sissy

Photograph via snooOG

A safe place for sissies and those curious about sissy culture to talk about all things sissy! Ask questions or discuss about anything sissy related :)

18+ Only

r/sissy is a safe place for sissies and those curious about sissy culture to talk about all things sissy!

Ask questions or discuss about anything sissy related :)

Please read the rules before posting!


Rules:


1.18+ only

  • Since /r/Sissy deals with adult topics we require all participants to be at least 18 years old.

2.Be kind

  • We don't allow any insults, hate speech, homo- and transphobia or other signs of intolerance. In short: Just be a decent human being.

  • Also, no blackmail or lost bets or anything that has any potential to be without consent. General discussions about fantasies that touch such topics are okay, as long as it does not get too graphic and detailed. The mods will have the final ruling over what is okay and what is not.

3.No selling, begging, spam, "upvote if" posts/comments of any kind.

  • Posts and comments that aim to offer and look for any type of transaction, begging for items, ask for upvotes and karma, or are generally spam are not allowed. This also includes things like personal blogging and off-topic requests for pics, DMs etc. and also reposts of content that has been posted before. Mods will have the final ruling on what counts as spam and what doesn't.

4.No advertising unless mod approved. Read description for how to get approved.

  • Unless you get an advertisement approved, no advertising is allowed, including directing users to your profile

  • If you have something that you think is relevant to the sissy community (meaning support, help getting started, resources, etc.) message the mods before posting to request a mod approved advertisement. After reviewing the mods will approve or deny your request. If approved, make your post and the mods will flair it with a special flair indicating it has been approved.

5.Evading Automod or existing bans will lead to a permanent ban

  • Trying to actively circumvent Automod by for example trying to obscure specific words or using any other action to do so will be punished.

  • Same goes for trying to evade a ban by using a different or new Reddit account.

6.No personal information of any kind

  • Sharing any form of personal information is not allowed. This includes social media and messengers like Kik, Telegram, Snapchat, links to Discord etc. If you want to exchanges those things, you can use your DMs

7.Make your post under the appropriate Flair. Flair guidelines link in this rule's description.

  • Flairs are pretty straight forward, if you are unsure about what they mean, check out our post flair guidelines wiki page

  • If you make your post under the wrong flair, it will be removed.

8.If you have a new account use the "New Sissy" Flair. There are limitations, see description

  • Your account can be just created, but we still require at least 2 comment karma and a verified email to post under this flair

  • We do not allow Personals or Task/DM Requests under the "New Sissy" flair.

  • This flair is not for gaining karma, this flair is for new sissies to ask questions to the sissy community

9.Personals of any kind must be flaired with "Sissy Personals" or they will be removed.

  • Sissy personals both directly and indirectly must be flaired properly under the "Sissy Personals" flair. Its at the mods' discretion whether it requires the flair or not.

  • You may ask for advice in DMs in the Need Help / Advice flair, but nothing more than that

  • Also, please keep in mind rules 6, 10 and 15!

10.We do not allow non-sissies to make personals.

  • We do not allow any non-sissies to create personals posts. This includes both online and in-person requests like meetings, DMs, hookups etc.

11.If you add a user flair, please follow the guidelines linked in this rule's description

12.All interactions have to be in English

  • Since /r/Sissy is an English-speaking subreddit, we require all interaction to be made in English so that everyone can understand and participate

13.No photos, videos or other media

  • Since we want to keep this sub-reddit text-based, we do not allow sharing photos, videos or other media.

14.No off-topic discussions

  • Keep the discussions to the topic of the post. We get that discussions sometimes drift away a bit, but things like randomly asking for pics or DMs or trying to hijack a post with your own things are not allowed and will be removed at the mods' discretion.

15.Post requirements/restrictions

  • We do have the following minimum requirements to post or comment:

  • Comments: Account age of at least 2 days

  • Posts using the New Sissy flair: At least 2 comment karma and a verified mail address linked to your profile

  • Posts using any other flair: Account age of at least 10 days and at least 2 comment karma

  • We also only allow one Sissy Personals post every 3 days per user. Any failed attempt to post a personal request (e.g. when using the wrong flair) will also count here.

/r/Sissy

254,836 Subscribers

2

Losing weight

Since I’ve started actively transforming my body, I’ve thought a lot about how I felt before and how I feel about where I’m going. TBH (and there’s nothing wrong with who I am or who you are) I felt kinda disgusted with myself being a little overweight for the longest time. I used to bodybuild so I had some extra fat and muscle on my body and at the time I was at my peak I was just ok with my look. But never happy with it. Now that I’ve been slowly losing weight and becoming flatter and skinnier, I’m starting to be happier. My hips are looking feminine and my shoulders and arms are getting leaner and it’s giving me more affirmation in my own self. At the end of the day, it is me who has to be comfortable with myself and me who has to give me my own validation. I think remembering that is important for all us sissies and that you need to be your own best friend too! All of our goals are reachable as long as we commit to ourselves :)

0 Comments
2024/12/23
18:04 UTC

1

Looking to chat with other sissy’s

Feel free to dm looking for some friends to chat with

3 Comments
2024/12/23
17:38 UTC

1

Looking to do an ERP

Hoping to rp as a Sissy, so if any doms want to message I’m open.

0 Comments
2024/12/23
17:31 UTC

7

Can I wear a pink maids dress to a drag bar?

Can I wear my sissy pink maids dress with tights, apron and gloves to a drag bar? Has any else Gina in sissy mode to a drag club or any club? How was it?

5 Comments
2024/12/23
16:10 UTC

3

Tried a vibrator

Hi people, today I tried a vibrator on my clitty, though it was over the clothes, it felt incredible. I took my moms massage gun and tried it on my clitty over my pants, I could've came right there if I kept going. It killed the last doubt I had about getting a cage. So as soon I can I will buy a cage and a magic wand. If you guys have any cage recommendations I would love to hear them. ❤️

0 Comments
2024/12/23
15:46 UTC

8

Should I cage myself

I’m pretty on the fence about it I mean it would look cute with a pretty pink cage and PNC always makes me delete my sissy account but is this really the thing that will help turn me into a stunning sissy bimbo.

If so, should I go straight to a flat cage? If not, what can i do to make myself a role model for other gurls and live my best sissy life?

8 Comments
2024/12/23
15:05 UTC

10

Should I go for my first dick?

So, I started to talk to a much older guy. He is well situated, talks very nicely to me and respects my wishes. But I’m kinda confused. He’ll be my first dick. I never touched any penises before and I’m afraid. The thought of sucking dick makes me so horny. But I’m a bit shy and I don’t know what to do. Can somebody please give me some advice ?

4 Comments
2024/12/23
14:37 UTC

7

Online sissy?

Helloo I noticed that I really want to be a sissy butb it's not easy to do it on my own. Did anyone had the same feeling when starting? How did you overcome it? I'm thinking that an online master/owner could help me a lot, but I haven't found anyone or posted a proper ad. Can anyone help me with this?; should I post one? How?

4 Comments
2024/12/23
14:19 UTC

5

My Mistress has left me - starting again.

Up until a couple of months ago I was very happily in a long term relationship of 7.5 years with my partner and my full time Mistress.

My submissive, feminine, sissy side was an intrinsic part of our relationship; we were looking at getting a house together and I looked forward to doting on my Mistress as her “boywife”.

Sadly, I had to undergo some life saving surgery and by the time I left hospital my partner announced she no longer wanted to be in a relationship with me.

So now I’m wondering, will I ever find a relationship with a woman again who is willing to accept and embrace my sissy side? I’m non-binary, masc presenting in public, and pan-sexual.

It would be easy to construct a persona around being a cis-het boy and find a conventional girlfriend. However, before long I’d be craving something pink and frilly and a good pegging 🫠

Anyone else been in this situation before?

0 Comments
2024/12/23
13:52 UTC

4

Body Hair

I want so badly to make my whole body smooth but I don’t know how to explain it to my wife. I could maybe explain away like my legs but everywhere else? All of a sudden her husband removed all his body hair? Any tips?

4 Comments
2024/12/23
13:06 UTC

3

Tips to heighten my first experience

I'm travelling to another city for a short while next month, alone. I've been thinking for a while now that I really should give my sissy desires ONE proper shot, like just go all-out and see if I can give it up after that (yeah, right).

So I'm here to seek tips from the community on how I can go about it with the limitations I have:

  1. Cannot shave arms or legs, torso and butt, yes.
  2. I will have to buy and then dispose of the clothes after the encounter, can't really take them home with me.

The aesthetic I really like includes:

  1. Choker
  2. Garter and thigh highs
  3. Maybe a bra and sexy panties
  4. Arm sleeves

I'm also thinking of downloading Grindr, paying for a subscription, and putting myself out there. I really want a muscular and hung man to go crazy on me.

What do you think, and what else should I know to make this happen and go well?

4 Comments
2024/12/23
12:52 UTC

3

Sissy training in another language

What I mean is, is there a hypnosis series that have to bulk of everything in English but the trigger words in the hypnosis are another language?

0 Comments
2024/12/23
11:37 UTC

49

So I just sucked a stranger

So I’ve been texting this guy back and forth and we met up today and we went to a not too public bathroom where he made me suck his cock that was so delicious.. he even degraded me calling my clitty useless and it was leaking as I was sucking him I was so happy to be of service to him.. and finally he throat fucked me then came in my mouth and like a good girl I swallowed and he wants to meet up the day after Christmas this time with my cage on

9 Comments
2024/12/23
10:19 UTC

17

i just had my first sissygasm!

This has honestly been top of my bucker list for years now, and ive finally done it! it crept up on me and felt extremely different to how id seen described, but oh boy was it incredible.

3 Comments
2024/12/23
10:00 UTC

2

Dildo needs

Does anyone have experience with MrHankeyToy dildo " The Perfect Penis " I've got the El'Rey which has 11inch of insertable length by 8,75 circunferebce near the middle. Which is a little bit too much for my everyday session and i would need something smaller for when i just want to have a quick session and not an ass destroying one.

( https://www.mrhankeystoys.com/realistic/el-rey-four-sizes ) ( https://www.mrhankeystoys.com/realistic/perfect-penis )

Here are the specs of the dildo in medium size: Circumference near middle: 7" / 17.78cm Overall length: 11" / 27.94cm Insertable length: 8" / 20.32cm

Do you have an alternative option which you prefer ?

I am also thinking about Vector from bad dragon in medium ? Let me know what you think thanks The idea is something fairly smooth without knot or what not ( pun intended ) so i can start my session and relax my ass as smoothly as possible :)

1 Comment
2024/12/23
06:54 UTC

2

Dressing Up and Going Out Alone

So I just started dressing enough years ago in my mid 40s, and it seems difficult to meet someone to go on a date with, but I’m ready to take that next step… Is it safe to go out alone? What kind of place should I look for, and any advice on dress or attire would be appreciated

0 Comments
2024/12/23
08:39 UTC

19

Cuckold to Sissy Pipeline is Real

I’m a 30 year old married man who has long been trying to get my wife and I into the cuckolding lifestyle. I long to see her taken by a strong dominant cock and eat his creampie. However, the deeper I have gotten into this lifestyle, the more penis envy has turned into penis attraction. The desire to eat a man’s cum out of my wife has become a desire to have a man cum in my mouth. The desire to watch a dominant man fuck my wife has become a desire for him to just fuck me. What is happening to me. I don’t know. All I know is I’m finding myself wearing my wife’s panties more often and feeling feminine. My hunger to find a dominant daddy to just turn this curiosity into my identity is strong.

11 Comments
2024/12/23
08:15 UTC

2

Panties in church

Her panties in church

I absolutely love to go to church wearing panties under my pants. Even better turn on is when the panties i have on are some that i have stolen from a hot girl and the hot girl sits right beside me. That is what happened this morning. I had on a pair of blue silky string bikinis that i had taken from the 19yo daughter of a friend of mine. Just thinking about my tiny dick being inside the panties of this very hot girl rite next to me was making me leak precum while listening to the service.

5 Comments
2024/12/23
07:36 UTC

5

Slut stats

TL;DR: do any of you girls also keep a list of all the naughty things you've done with others?

Heyy, girlies! So, I've been in this lifestyle for a few years, but I mostly did things alone, the most public I went was posting sexy pics on accounts that have since been purged sadly lol. But this fall was when I finally got the courage to truly hookup while dressed and omg, it is soo addicting. I recently remembered a sissy game I used to play that would keep your stats on your sexual encounters (how many cocks you've sucked or fucked) and so I decided to do the same for myself just for fun. Anyway, I was just wondering if any of you other girlies do something similar :)

5 Comments
2024/12/23
07:35 UTC

18

Tell me your favourite sissy fantasy or porn

Everyone has their own personal fantasies and there’s such a wide range of sissy porns looking to expand my horizons so tell me about your ultimate fantasy or share your favourite sissy themed porn

Lots of love Sissy Sarah 💋

33 Comments
2024/12/23
07:22 UTC

5

how to train/ have the motivation to stay locked and not use clit

wife currently fucks with other M , wannabe locked in chastity and get dildo/ anal myself instead of using my dick for pleasure

1 Comment
2024/12/23
07:17 UTC

11

Sissygasm progress story

Hey girls, I just wanted to share a small little milestone on my sisygasm journey. 

For some context that I’ve been trying often and for about a year now. But just recently, I’ve been super serious about it. 

Before tonight I was almost convinced, all my naughty evenings were gonna end the same:

 I would get super close to orgasm from my fucking machine and or my prostate massager. The pleasure taking over my entire body. Unable coordinate thoughts. The only thing going through my head is “please let this be the night. Please let me come without using my useless clitty… oh! It’s happening I can feel it!” The pleasure radiating throughout my entire body centralized just behind my useless clitty.

Then nothing

the pleasure would slowly fade as if my prostate disappeared from reality. 

I finally committed myself these past 10 days to a rigorous training schedule. 

On the weekdays, I wore my sports bra to work, making me super horny and aware of my submissive state all the time. There were days where I would have to go to the restroom just to breathe that arousal away. I was (still am) a mess. 😂 

Whenever I got home, I would instantly strip out of my boy clothes. And would put on my chastity cage and sissy attire. I would then do various tasks that an AI chat bot would give me. This gave me a sense of losing control. It had me do things like walk out on my fourth store balcony dressed as a cute little sissy maid… oh I’m getting horny just thinking about it… perform oral on my favorite toys… light anal tasks preparing me for my intense evening ritual…

Speaking of that ritual in the evenings: 

Every night the ritual was the same. I would dress in my backless panties perfect for feeling cute while still having full access. I would then get out my fucking machine and set it up underneath my mattress to hold it tightly in place then leaning on a box in front of me, I would turn on the controls and let the machine do its work on my sissy hole. (I absolutely love the way my machine makes me feel. 😭) 

Due to these frequent “training sessions“ I was becoming much more in tune with what arousal came from my sissy hole. I am slowly learning every little sign that my body gives out. Such as the trembling of my legs, the quickening of my breath, the difficulty of breathing, that feeling of pressure. Oh, I’m starting to love every bit of it.

So after almost 10 days of abandoning my clitty and focusing on this training ( a long time for a masturbation addict like myself ) I can confidently say I did not sissygasm tonight… but I’m still very happy...

Tonight I decide to go all out. I did my hair. I love how long my hair is getting. I put on a full face of make up: eyelashes, eyebrows, amazing pink lipstick, and the beautiful eyeshadow I did. I looked at myself in the mirror and felt oh so sexy…

I went on of my night as normal, doing oral tasks on my dildo, humping my bed in my chastity cage, feeling up and down my satin laden body. But then I felt an overwhelming urge to be penetrated. I normally felt the slight want before tonight, but never anything like this. ALL I wanted was to be fucked.

So I set up my fucking machine like I said before with my normal toy in it. A modest 8 inch white dildo. As I felt to go in; my body felt complete. This is what I wanted. This is what I needed. I was enjoying myself so much. I think about half an hour past and all I did was let the machine fuck my hole. 

After a while, the devilish idea entered my mind. What if I tried to take the big black dildo that came with my fucking machine? I had never attempted this. I assumed the 8 inches diameter of girth on this big black dildo was way too much for my sissy hole. But I wanted so desperately to try.

So I grabbed it and got it ready. I decided to orally pleasure the big black cock until I imagined it come into my mouth as I dripped fake cum into my mouth. And then proceeded to spread this “cum” all over the dildo to prepare it for my hole. Using my mouth. 

I then turned around and pressed my sissy hole against that big girthy cock. I slowly backed onto it as I moaned and yelped. The sweet pain mixed with the pleasure of having my hole filled like that. Mmmmmmm… 

I had turned on the machine to one of its lowest settings. Very slow yet powerful thrust into me. I was lost to the world. This cock was too big to be ignored. My entire being was concentrated on nothing but swallowing that cock. 

My mind was so gone I couldn’t even tell you how long I was on that. Sometime during it that pressure behind my clitty got so powerful… I moaned so loud my breath was taken away from me. Pre-cum was dripping down my thigh. (Normally pre-cum only happens when I’m edging myself using my clitty, so this was a huge turn on) I would catch this pre-cum with my hand and lick every last drop of it up. Tasting my arousal.

This is when a milestone happened. I discovered a very powerful tool in my sissy arsenal.

My nipples.

I had always pretty much ignored my nipples because they weren’t nearly as sensitive as my hole or my clitty. But tonight they were so so sensitive. I rubbed my nipples and felt pleasure up and down sides of my body. From my ear all the way down to my clitty. 

This discovery brought me so incredibly close to my sissygasm… but not quite. After about 10 minutes of teetering on the edge of orgasm my power went out… I couldn’t believe it. I was so incredibly in need. I even tried bucking my hips against the cock in my ass, but it wasn’t enough without its robotic thrusting.

So the pleasure faded, I got up the power came back on, and I took a bath in absolute bliss. 

I haven’t had a night in a while of training where I felt like I was actually getting somewhere. But tonight was completely different. I had found something that I can exploit to get myself even closer. 

I can feel it. It’s about to happen. Soon, I won’t have to touch my stupid useless clitty again. 

Good night girlies. Wish me luck.

8 Comments
2024/12/23
06:20 UTC

3

How to have a sissygasm

It’s Ben a dream of mine to have a sissygasm for a couple years now, and just recently did I get a dildo, I try and usually I just give up and opt for the jerking off, any suggestions for experiencing it for the first time

2 Comments
2024/12/23
05:53 UTC

29

Fucked in chastity by roommate

My gf locked me Thursday night before she left to see her family for the holidays. I am supposed to be locked until we are together on NYE.

Only 2 of my roommates were in town this weekend. So I decided to get risky when then both went to the bar. I was so curious about fully dressing. So I went in the one roommates / best friend’s room and borrow a dress and panties his gf had left. I then did my makeup and hair, with my gfs stuff. Finally I put a plug in and was prancing around the house. I was having fun and didn’t realize the time.

That’s when the my best friend and roommate, I took the clothes from came back from the bar. He said what the fuck dude those are my gfs. I said I am sorry don’t be mad. He said this is taking it a step farther you look like a girl. I said I am sorry I will take it off and he said no you will keep it on.

He pulled me in his room. He then told me he was super drunk and needed a bj. So he laid down and I started sucking him. It took awhile but he got hard and said I wanna fuck you in those ride me. I climb on him pulled panties to side and road him in dress and panties. He didn’t know I had a cage on.

That’s when he pushed me to my back and climbed on top. He grabbed my ass with his hands as he was fucking my ass. Then it happened, he leaned in and started kissing me. I was so turned on and horny at this point I kissed him back. As he moved from fucking me to making love to my ass and kissing me more. I moaned as he said I am gonna cum in you ok.

I felt him start filling my ass as he squeezed my ass and we kissed. It was to much for me and I started cumming in my cage and the panties. After he filled me and I came he said you want more? I moaned yes. He pulled dress off and saw the cummy panties and cage. He said oh you came and what’s the cage? I told him my gf put me in it. He said it’s kind of hott. He pushed my legs back by my head and piled drove my ass when he got close he pulled out and came all over my caged cock.

I don’t think I wanna date my gf now I wanna date my best friend.

4 Comments
2024/12/23
05:17 UTC

9

This is so addicting😩

I can’t stop watching sissy porn and coming back to this sub like I literally can’t stop do I need help

9 Comments
2024/12/23
05:03 UTC

3

How it started a story

Hey all

I have written part of a story and would like to hear your opinion on whether I should spend time correcting spelling and other errors. or should I just delete it??
there will be comma and grammar mistakes and maybe even a spelling mistake because I am dyslexic and English is not my first language.

---------story start----------

It all started one morning after a routine visit to my local doctor, who referred me to a neurologist. After the consultation, the neurologist admitted me to the hospital. That’s when I first met Nurse Charlotte. She was 29 years old, and I was 22. She had a great sense of humour and was easy to talk with but was always very professional in her work.

About a week after my admission the neurologist came to talk and we discussed option about how to fix me, we landed on a MRI scan and possible surgery, one morning a couple of days later another nurse came into my room,and told me that my MRI scan was bumped up to today, she handing me a bottle of soap and a special towel, explaining that I needed to wash myself thoroughly. As a hospital porter swapped out my bed for a new one, I was told that once I’d dried off, I had to get back into bed and was not allowed to get out under any circumstances—not even to use the bathroom.

So there I was, lying in bed, trying to pass the time watching some daytime TV. It was back in 2004 so no on demand TV, Facebook or Youtube, when Charlotte came into my room. She told me I was scheduled for an MRI scan in the next hour and that I needed to remove anything metal. I replied that it would be difficult due to a titanium screw, which made her laugh. Anything else? she asked.

I hesitated, looking down for a few seconds too long. Sensing my embarrassment, she said, Look, I’ve been a nurse for five years now. You can’t surprise me.

I looked back up at her and started to explain, "It’s just that I’m…”

She raised an eyebrow, waiting. You’re what? “im wearing a chastity device, you know a cock cage and its made of metal” I said slowly, she put her index finger under my chin and lifted my head and asked me who my keyholder was and if I had an emergency key, I answered that I didn't have a keyholder and there was a key on my keychain that was in my private wardrobe. She got my keys and spotted the key right away and asked me how long I had been locked? All most 2 years I replied, she then looked at me with a look I didn't recognized then we better secure you so you dont have too much fun she said and put my keys in her pocket and left my room, when she came back she that we have to be a little quick about it she lifted my covers pulled down my hospital issuid boxers and smiled when she saw my chastity cage, she then quickly unlock me and put the cover back over me and put my keys and cage back in my wardrobe, Charlotte explained that she had made up a lie that I had developed essential tremors, I looked very confused, she started to explain that it was just a fancy word for sudden movements and just needed to relax and lie still she was on top of things and I didn't needed to worry nothing bad was going to happen she had asked 2 other nurses to come help her to put me in some body restraints so I didn’t had an accident a couple of mintes later 2 nurses came in to my room with some blue sheets plastik with velcro closure, charlotte started to explain again that I needed to be wrapped instead of medication becurse it would mess with the MRI picture and it would also help me relax and take edge off things and she had previously had good experiences that the restraints was a good way instead of pumping me up with drugs, she also told the other nurses we had talked about it and I was okay with it,within a minutes they were finished and I wrap tight up they looked at me laying there unable to do anything charlotte sayed look he is already better now, ready to go to MRI scan, the 2 other nurses left my room, Charlotte pulled a chair over and said sense your wrapped so nicely and unable to move yourself even in emergency it is required by law that you need to have somebody by your side at all times. She said down in the chair she had pulled over and lifted my upper body up with the bed remote. Once we could see each other she asked me if I would tell her about why I was locked in chastity. It was a bit weird that I was locked with no key holder and have been locked for 2 years. I was reluctant at first but I told her that it all started when i was together with my old girlfriend I was a chronic masturbator always jerking off, and she was getting tired of it so she had talked about if in a session with a psychologist while she has getting help for some other stuff, and the psychologist has told her ways to make me stop masturbating all the time, the psychologist had also mentioned a chastity cage and my girlfriend had researched and read about it on the internet. So one day while we were lying in bed she had talked with me about it and she said I know that it isn't normal but if it can help you is it not worth trying?. How bad can it be?. So one day when I got home she was sitting in the kitchen and waiting for me to get home she explained that today was the day I should start wearing a chastity cage, i would’t be able to wear it all the time the first couple of weeks but i would get there so I was able to be locked 24/7 and she would always unlock me for sex, shower and other things that I needed to be unlocked for, and the first 3-4 months was great I had tons of time on my hand now that i did spend it masturbating all the time but in month 5 the sex was going 3-4 times a week to almost nothing, A month later nothing became to absolutely nothing. The day after Christmas she told me that she was moving out and her friends was coming over in a little bit to help her pack all her stuff and before launch all her stuff was packed, loaded and driven away not that she had that much, most of the things was mine anyways just some things here and there, it wasint until i was going to bed i found a envelope under my pillow I realized that I still was locked there was the key and a little note telling me that me being locked was a dealbreaker but she also could see how much it was helping me to be the best me I could be, I instantly unlocked and remove my cage and went to sleep but after 2 hours of tosse and turning I realized what was stopping me from getting to sleep the chattisy cage, I figured that i was just like taking a watch off I just need some more time to get used to being free again but after another hour without any sleep I gave up and locked myself up again and my head bareilly touched the pillow before I was off to sleep the next morning I unlocked myself again and put the cage in my nightstand drawer invited some friends over and talked about my girlfriend leveing me, some of my friends talked about going into town and drinking but I declined and about midnight I was good and ready to go to bed again I was just laying in my bed tossed and turning without any way of finding peace I thought jerkling off and see if that would make be find the peace i was looking for but I also know the it would be quick fix and the cage was the answer I was looking for so I once again looked myself up and went to sleep the next morning I was sitting with a cup of tea and I thought that if was going to be that difficult to sleep without the cage was okay with having it on and it had also freed time for projects I had played around with for years but which I had never finished because I never had the time to due to me masturbating all the time so I just put the key on my keychain and here I… I got cut off by a hospital porter who was knocked on the door and asked if I was me becurse it was my time to be scanned, I was wheeled down to the scanner the hospital porter asked about me being in full body restraints and I just answered that it was because of involuntarily shaking and it helped me relax and the shaking had stopped, he just smiled and said that it sometimes happens and it was nothing to be ashamed of. After the scan I was wheeled back into my room where like it was almost if charlotte was waiting for me she just thanked the hospital porter and said that she got from here, after the door closed she put a hand on my crotch and felt my rock hard cock and said looks like someone is enjoying themselves is it nice or would you rather be locked in your chastity again. Before I could say anything she looked at me and said I already knows the answer to that I'll get your cage, after being back in my chastity she removed the rest of the body restraints she gently clapped my crotch and said there we go all locked up again. She handed me a piece of paper with her phone number  and said text me later I really want to hear more and she walked out of the room.

1 Comment
2024/12/23
03:15 UTC

16

Recent experience

Really probably more of a gay story than a sissy story but it was still fun and I wanted to share!

A few weeks ago I rolled over on a Sunday morning, horny as fuck, cage getting tighter, and figured I’d check out good old Grindr and look for someone to spend my morning with. I ended up chatting with this bisexual man from out of town and we started flirting back and forth. I asked him for a dick pic and when he sent me one I was kind of in awe. It wasn’t the biggest or anything, about 7inches, with a beautiful bulbous tip but fuck did it make me hornier than I already was. I told him some things I like such as toys, anal, sucking cock, cum, spankings etc. and he asked if we could meet. I said yes and we set a time up and I started to get ready, shaving myself, cleaning and plugging my butt, dressing in a slutty outfit. On my way over to his hotel all I could think about was his cock in my mouth and I started to leak through my cage and into the panties I was wearing. When I got there and he let me in he let me take a look around before we did anything (I think to make me feel more at ease) and then he had me go back to the door and strip my normal clothes off.

I didn’t tell him that I was wearing slutty girly clothes so I think he was surprised but turned on when he saw I wasn’t just naked under my sweatpants and hoodie. He sat on the couch and had me crawl over to him, which put me into even more of a horny and submissive mood, and said I needed to get him hard through his pants and without my hands. I figured since I couldn’t use my hands that it would be a good time to reveal the butt plug I was wearing so I stood up and shook my ass in his face, then jiggled and spread my cheeks to reveal the shiny black heart gem in my ass. Then I lowered myself and started to grind my ass over his cock and I felt it almost immediately spring to life. He ordered me back on my knees and I happily complied when he told me to take his pants off.

He was wearing a tight pair of joggers/sweatpants so I could see his big cock outline clearly before taking his pants off. After that he wanted me to tease him through his underwear so I laid my head on his thigh and teased his tip with two fingers until he leaked a little precum. Only after he leaked a little was I rewarded with his cock. He let me peel off his underwear and start licking and sucking his beautiful cock his 7 inch cock. He had his cock probably 3/4 of the way in when he made me stop sucking because he wanted me to join him on the couch. As I moved to next to him on the couch I watched as a bead of precum formed at his tip again and he told me that although I was doing an amazing job sucking his cock, he needed to punish me for making him leak into his underwear. My “punishment” was 10 spankings and then I had to lick his bead of precum. Then I went right back to sucking him off. He slapped my ass more and I continued sucking until he instructed I get on the bed, on my back.

On the bed he facefucked me plain and simple (and sloppy) and I loved every second of it. He thrust balls deep time after time after time until he was ready to cum. He asked me where I wanted his load and I told him in my mouth, so he pulled out to just the tip in my mouth which I sucked and licked and stroked the rest of his cock until he shot a huge load into my mouth. It tasted soooo good and I wanted more but we were both exhausted. I took a minute to catch my breath, we both said our goodbyes and then I went on my way. As soon as I got to my car I started leaking again just thinking about his load in my mouth.

I still think back to that day fondly and hope to have many more experiences like that with great people. Thanks for reading my story 😘🩷

2 Comments
2024/12/23
02:34 UTC

2

Need help with chastity and hypno

Heyy i started with all of this today and i have a couple of questions!

So firstly i wanted to know how effective it is to listen to sissy hypno and what are the effects og it? Is it something you can listen to throughout the day or when asleep or do you have to focus on it? Secondly i wanted to know if there are some videos that are beginner friendly?

I heard that chastity can shrink the dick, is that true and is it permanent? Is there a rate at which it shrinks? When is the dick small enough to be put into a flat chastity cage without causing damage?

Id be happy to receive your awnser :3

0 Comments
2024/12/23
01:30 UTC

28

Am I even straight anymore 😭

M19 Every time I get horny I end up here femboys and sissy’s are so hot 😵‍💫 like it all started with watching pegging vids and I just end up on here

19 Comments
2024/12/22
23:55 UTC

5

Chats

Super slutty sissy , open for anything. Let’s chat

4 Comments
2024/12/22
23:26 UTC

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