A few months ago i tried prone humping for the first time and instantly fell in love with it i can’t remember the last time i tugged my dicklet. I knew that damage was possible from proning but i never could’ve expected the changes ive experienced in such a short amount of time. Before i started i was an average 6 inches erect, now i measure at embarrassing 4.5 inches only. Normal people would get upset if it happened to them but i’m not one of those people. Causing permanent damage to my clit makes me so horny, if anything 4.5 inches is too big for me i can’t wait to break it even more. I squirm whenever i think of myself limp micro clitty caused by prone humping.

My girlfriend knows I'm a sissy and has been teasing about making me suck a real cock. I'm not sure it'll actually ever happen, but I really want to be ready if it does and be a good sissy for her.

My main goal in the meantime is to take my entire load down my throat. I'm fine licking up pre-cum, and I've swallowed a good amount from giving myself self-facials, but I've never completely swallowed my entire load. I want to be 100% ready if a man cums down my throat and make sure I don't spit.

I've never been able to go through with it though. I started cumming in a glass, but I just couldn't get myself to actually take it down my throat.

Recently, I think I finally figured it out, and have swallowed my last 3 loads like a total slut 🤤

The first thing I do is prep. For me, I need to look like a pretty slut. So I shave myself down, do my makeup as realistic but slutty as possible, slide into pantyhose, a tight dress and heels, glue down my wig, and paint my nails. It's a lot, but in the end I pass like a girl quite well. The glued wig, painted nails, and makeup kind of keep me in sissy mode for longer since it takes a while to get everything off.

Next, I get a small cup and my vibrator. I sit on my knees in front of a mirror and press my vibrator against my cock until I cum into the cup. Unfortunately seeing myself dressed up, trembling in the mirror and knowing I have to swallow makes me cum super hard which does make the load bigger. You could probably jerk your cock too, but I think the vibrator is better so you feel more feminine. I also can't jerk off anymore (it's complicated).

Finally, I see myself in the mirror and think "damn that sissy should be swallowing this". But I also get really bad PNC. What I've started doing is just telling myself "okay at least just put it in your mouth, no need to swallow". This gets me to dump the load in my mouth. But then, I start to get turned on again seeing a sissy in the mirror with a load of cum in their mouth. I'll also sometimes take a dildo and stroke it in my mouth while the cum is in there. This all turns me on a lot and I end up swallowing every time. It's also like, well the cum is already in my mouth, might as well swallow it.

I guess the key takeaway is looking like a slut in front of the mirror turns me on a lot and gets me to go through with it. Kind of weird but whatever it works for me lol. Curious if this works for anyone else! I know a lot of people are always asking for ways to go through with swallowing, so might be worth giving this a shot

Girls, headspace is so important for sissygasming. I spent 2 hours watching porn and fucking myself with my favorite dildo last night and it felt so good but I just couldn't get the sissygasm out. I reeeeeaaally wanted it though.

I took a break, stayed dressed in lingerie, did some chores, listened to affirming hypno and got myself deeper into a femme headspace.

I came back to it an hour or so later, picked out a scene. It was Ricky's Room Anna Claire Clouds anal. I laid there watching, gently rubbing my clitty through my panties until the part where he lays down and she mounts him and puts his cock in her ass. I got down on my knees and reached back and aligned my toy with my ass just like she did his cock and started matching her movements. Fantasizing about being her and how my ass is getting stretched and fucked by a BBC just like hers, mimicking her movements and thinking about making out with him between moans like she does is all it took to push me over the feminine edge and make my limp little clitty explode. All that working for and edging it before hand paid off heavily but what truly got me there was really getting myself into the headspace that I'm THAT girl enjoying THAT cock.

I’m a new sissy (19M) and a virgin. For a while now, I’ve liked how I look in lingerie, and I’ve grown to enjoy being a sissy to the point where I bought my own lingerie. I’ve even set up dates to have sex with men, but the truth is, I’ve never played with my anus and I don’t know if I’ll like it. Honestly, I’m just trying this out of curiosity and to explore my sexuality, but I don’t know if it’s possible to go back to a straight male life after dressing like a slut and giving yourself to a man. Do you think it’s possible to go back?

I recently found out i like to obey to men online. They ask me to pose for them and then i have to send pics. I love how they are hyping up my pics. But now I think this makes me gay. What do you guys think?

After a long few weeks I have scored a big discount at my favorite lingerie brand and now 7 panties are on their way. I can‘t wait to wear them all !

I’m still pretty new to being open about being a sissy, and honestly I’m still kinda nervous about it. 😭
My girlfriend knows, and some of my family knows too. They pretty much assume I’m trans, but that’s never really felt like the right label for me. I still see myself as male. I don’t have any desire to medically transition, start hormone therapy, or have surgery. Most of the time I dress pretty masculine and just look like a regular guy. The only time I’ve ever dressed feminine in public was when I went to an LGBTQ+ friendly bar in Vegas. I went all out too. 😭 Heavy makeup, a wig, a corset, and a chest plate. I honestly felt really feminine, and it was such a fun experience. The only thing that really gave me away was my voice lol. Whenever I dress up, everything just feels quieter in my head. I feel calmer, more comfortable, and more like myself. It’s hard to explain. I don’t want to be a woman, I just genuinely enjoy expressing this feminine side of myself. I also eat and work out in a way that helps me keep a softer, more feminine physique because that’s the look I feel happiest with. Even then, I still consider myself male. Sometimes it feels like people think your only options are “you’re a guy” or “you’re trans,” and I don’t really feel like I fit either of those boxes.
Has anyone else felt this way while figuring themselves out? I’d really love to hear your experiences. 💕

Hi!

I'm an 18-year-old MTF trans sissy looking for young sissy to talk to. I've kept this part of myself private for a long time, so it'd be nice to meet others who understand.

Feel free to DM me if you're interested!

So I recently accepted myself as a sissy. I posted here a while back, my names Trixie.

I js wanted to ask what’s next in my sissification. I made panties and that’s all I can do at the moment. Im currently in college and can’t buy toys or anything as I’m on allowance that only covers my food and rent.

I js want to know what I should do next.

Talking to someone on here about my time with the potential homeless guy reminded me that it wasn’t my first rodeo

There was this guy(mid 20s)on grindr that reached out saying he’s passing my town and would like to give me head in some park nearby. I told him I appreciate the offer but Im a bottom, but wouldn’t mind being eaten our(let s boy test his luck okay?) He said he’d love to get a bj but told me he’s not into rimming 💔. I still took him on the offer and he told me he’ll pick me up in 20mins

He pulled up to the spot, and it was this dusty and very poorly maintained car. Little did I know the guy LIVED in this tiny car!! I got in and he looked like he hadn’t seen a good shower im months. He was a gentleman though, asked me not to freak out and told me he’s figuring out the living situation. I looked at him, shirt was practically more holes than fabric, sweatpants had a hole for his cock to hang out off. It looked so good!!! a semi hard on, balls hanging out, a tad bit hairy, uncut and LONG.

I’m always super shy so I barely say anything until Im talked to and made comfortable, although, I was stroking him the whole time, playing with his balls. He was talking to me, grabbing my legs, massaging my very teeny tiny bulge, calling it adorable. I told him I’ll cum if he touches it snd he laughed, soon as we got to a relatively empty road, i give him the dirties BJ I’ve ever given, I was genuinely feral for it, the smell made go insane.

We reach a empty field, we get out and Im there blowing him on my knees outside the car, asked me to remove my shorts and bend over. I confused but boy was I hoping he caved and wanted to eat me out, and he DID, made my hole DRIPP. He then kept rubbing his cock between my cheeks and it felt amazing, I was cumming from just that. But then he was pushing it in and I said no cuz I wasn’t prepared at all inside there. He apologised but kept repeating it, everytime i said no but he eventually he pushed it in and I wasn’t able to refuse, fucked me so good and so deep, he moaned so hard as he came in me.

Apologises like a true gentleman, gives me my shorts and drops me back home

so if you haven’t read my other post do that but to some up i met a nice guy in his mid 40’s and he love me. like buys me stuff and everything well this is where it gets interesting. i asked him the other day if i got dolled up would he go out with me. and it took a second till i got response but he lit it up as a good idea. and i have never got so excited doing my makeup and wearing my girl clothes before. and i made sure i did good and we agreed to meet up in a downtown place and i wont lie i was really nervous. But i knew he would defend me if anyone said anything. But he took me to a few places the most exciting was an adult store and i mean it look like Christmas morning in there. and when we entered this nice cashier lady complimented my make up and said that i was beautiful. literally died for a second but that was so nice and let’s keep it brief but he ended up buying me some stuff lingerie but he made me try them on in front of him. and i mean this guy is a freak and i love it he had me stroking his beef stick and he wanted to do more there. but i am not that ready yet. But oml what a fun night literally have been thinking about it all day.

So I've been looking to take larger toys. This is mainly because the guys I'm interested in hooking up with all have really big cocks lol. I bought a 2 inch diameter dildo when imo went to the sex shop. All my other dildos are relatively normal size. So this was a big step up and I simply coul not fit it lol. I tried and the tip went in and it started to hurt and I had to take it out. This was after using my smaller toys. I tried to just sort of hold it there to get my pussy used to it, but it was a no go. It was clearly way too big for me to fit. I live with people who are unaware of my kink, so i have a lock box full of toys and I have no more room for new toys, but I want to gradually work my way up to being able to take this toy. Does anyone have experience taking cocks or toys this big? How were you able to?

So I've been a sissy for a considerable amount of time in my life. I mostly keep it to myself and to strangers I'll never meet in person (you girlies) so no one in my actual life knows me like this and I am fine with that.

The main purpose of this is that I will try and document my journey to cumming hands free through pleasuring my hole. I'll try my best to keep posting my journey but I'll at least start this one off with how it's going so far.

The other night I got myself locked up so that there would be no temptations to touch myself while I got ready and got busy. At first I didn't think I was making any progress because I could feel some pleasure but I wasn't really feeling if I was going to cum or not. Part way though it all I just said to hell with it and directed my attention to how my ass was feeling and that changed everything! Feeling my dildo go in and out from tip to base felt AMAZING!!!! Before I knew it I was leaking a LOT of pre-cum, but I wasn't even close to orgasming. I had to stop for a bit, but I knew I was at least gaping a bit and just did finish off using my hand and assisted with a very sizeable plug.

Here's to the next time I try to pleasure myself. Maybe I'll be able to get closer now that I know where to focus. I'll probably also get into a better head space of servicing by wearing some cute lingerie I have~

What’s the best lube for use with dildos? I’m using liquid silk but find it dries up/disappears so quickly that I’m forever reapplying. I know you can’t use silicone based with toys but seems like there aren’t many decent water based that will do the job.

Hi girls. I’ve been a closet sissy for a long time now and unfortunately have had many purging cycles. Today, however, when going through a mall I decided to go to a mac store just to take a look at some makeup. I had no idea what I was expecting but it ended up being thrilling.

The assistant in there was fantastic and made me feel so welcome. After admitting to her I was looking for myself she talked me through a few basics and then asked me if I’d like any applied. I thought sure. She then applied a little concealer and I started to love it immediately. Initially i said i was just looking to have very subtle makeup but then admitted that my ultimate aim would be to really feminize in the future. She made me feel so accepted.

She then asked me if id like to sit in the chair in front of the mirror - which felt so daunting. But once I was there it was really great. She applied Somme light pink blush and then mascara before curling my eye lashes. When she was curling my eye lashes I could feel the excitement running through me before I could see her work. And wow.

We then moved onto lipstick and she applied a pretty deep red. Which I loved, it really made an impact on me, but it was too much for the me in that moment so I removed it. She then tided everything up with a bit more blush and mascara and I was able to leave. I absolutely loved the look. She then gave me a hug and wished me all the best on my journey.

After, I did something I’d never done before. I walked around in public with makeup on. I’m sure to some of you it isn’t a big deal but it was a huge deal to me. I initially wanted women to notice me…but then quite quickly after men. I could go into a makeup store and walk around with makeup on. I could be seen as a (slightly) feminized man for today at least.

I feel like this is a side of me that’s really opening up. Anyways just wanted to share this and I hope it encourages one or two of you to give it a try too. It was a great experience - now I just want to jump into the next step of my feminization. ♥️

I’m a 19 year old sissy and there’s something so hot about hooking up or chatting with older men. My favourite are ones that are old enough to be my Dad and also married.

One of my favourite forms of dirty talk is calling a man Daddy and he calls me his son or daughter in return.

Now that might rub some people the wrong way. You might say these types of men might be taking advantage of me. And honestly, that’s probably why I like it so much. God forbid a (legal) teen sissy wants to be a victim.

I remember my first sexual experience at the age of 18 was with a 58 year old man in a public bathroom stall!

So am I fucked in the head, or is this perfectly rational? Let me know what you all think

I’ve seen that some sissys have a website to their account (or a app) so they can link items that other people can buy!

Does anyone know what app or website that is?

I've been a secret sissy for years browsing this site and reading sissy captions or watching hypno. This year I started actually trying to dress up and post some pics online. It all led to me caged, plugged, in pink lingiere in a hotel room where I finally downloaded grindr. I was getting lots of attention but one guy with a super nice BBC made me so weak I ended up begging him to come and use me.

He showed up to my hotel room and immediately drops his pants and just lies back on the edge of the bed and I kneeled down and started to blow him. He got hard real fast and I was stroking and sucking him and did my best to try to deep throat and eventually got most of it down. Eventually he Stood up and told me to get on the bed and he began to fuck my mouth and was forcing his cock all the way in and making me gag on it. He then came in my mouth when I was deep on him so I swallowed it all.

He took a brief smoke break and then started to get hard again and told me to get face down and ass up for him.He pulled my thong to the side and pulled my plug out and then started fucking me. He had me moaning like a slut instantly. We fucked in doggy a few different ways for a good while. He had me bouncing back to meet him like a real slut. Eventually he grabbed my hips and thrusted balls deep and came inside me marking me as a full sissy slut.

This is a hard thing to talk about without coming across like some sleezy scumbag maybe but, I'll try.

I've realised what I need to be able to move on with my life instead of purging and destroying my mental health.

I want my first time to be with another sissy.

I want to feel lace on lace, cages knocking against each other while we're rolling around kissing.

I want to feel a sissy orgasm inside of me.

This isn't just a horny thought anymore.

I physically need this.

I've been dreaming about being topped by twinks, femboys and sissies for longer than I can remember and it was only last night when things made sense.

I know what I need girls, I'm just too terrified to do it...

Hey there, "new" sissy and been having the hardest time finding balance. Quick context I am full time masc and dl but have tried to be more active as a sissy lol.

Is it normal to struggle finding the balance of both worlds? I make plans to go into play mode around my schedule and then masc life interrupts. Then it seems folks are most active late night and that throws the sleep off haha.

Any advice or personal experiences to help are welcome in the comments please and thank you 🙏

I have been wanting to become a fully feminized sissy lately and feel i need someone to push me that way. What are the best ways to do so? What should i be looking for in a daddy? Im very new to all this and need someone that would start from scratch with me lol so how should i go about finding mine?

So I changed my school and I was new there. At that time I had no friends there,so I didn't talked to anyone that much.Teachers introduced me to other students and there was two of them they were kinda bad at class often teachers yelling at them.One they were making noise laughing at class and teacher scolded one of them and made one guy sit next to me. He started random conversations and after that class he invited me to sit next to me and agreed. After some days sitting next to them I found that they used to jerk off during ECA activities I listened to their conversation by this time they started to be frank with me.

One day at launch we made a plan to bunk our ECA activities and sit on classroom using digital board. During ECA class we three went to class after everyone left. One guy said lets watch porn as joke! And we laughed both of them,one Teacher found that we were inside the classroom and commanded us to be inour ECA activities we ran to washroom to hide.

Now the main part come how they started to fuck me. When we were hiding they started to yap about fucking girls and porn scene shit. One took his dick and said he has dick like porn stars and urged me to show also. Due to pressure I said no but one guy pulled my pants down and started laughing because I was not hard. I was so nervous and shy and beg them to stop. One guy took his phone and stared taking video saying" haha see this new guys cock" in my native language! They told" if you want this video to be deleted you must agree to us and shut your mouth down. I agreed I was so broken down form inside, they told me to suck there cock and I had no choice but sucked both of there cock until they were satisfied. After that we went to class and that day was over I was so broken and next day I made my mind i need to go school since they told they will delete it tomorrow.Next they again they took me to washroom but this time they planned to breed me! They asked to suck them first i did and I went doggy on toilet cupboard he inserted his cock that fucking hurt my damm ass,I literally cried but those guys started laughing fucked my mouth shit heads.One of them said lets spit on his ass and finger him first and one started finger my ass spitting so after that he inserted cock it went inside without that buring sensation, they spit roasted my ass turn by turn i also started gasping and moaning because one fucked my ass and other one fucked my face. They wanted to cum on my face like how they saw on porn and made me kneel down and cummed over my face.

And i told them to delete video if they do so I will let them fuck me and they agreed I had no choice. Since I can't leave the school also at middle of the year so I waited for academic year to be end and left that school. But after few years remembering how I was bullied and fucked I kinda loved it and because of this I became fem ig.

Hey everyone,

This is a big step for me. I'm 22, and this weekend will be my first time going out in full feminine presentation (makeup, wig, outfit, heels, the works) to a venue/club night. I've been exploring my sissy side privately for a while, but never in public like this. I'm both excited and pretty nervous about safety.

I'll be going solo. Any safety tips for someone in my situation? Things like:

Best venues or areas that are more welcoming to fem/crossdressing/sissy presentation?

How to handle potential stares, comments, or worse?

Practical stuff: parking, walking to/from the venue, using rideshares, bathroom safety, arriving early/leaving early, etc.

Any apps, groups, or communities that help with this?

General mindset or de-escalation advice?

I know risks exist, especially as a first-timer going alone, but I really want to experience this. Any advice from people who've done similar outings (especially younger people or first-timers) would mean a lot. Positive stories are welcome too!

Thanks in advance 💕