r/Sissy_Stories

I was messaging this guy for weeks before our schedules matched up so anticipation was high. We talked about all kinds of things we want to do with each other he opened my mind for some things I have yet to try. He was married, but his family left for a few days what gave us ample time. I took some days off from work for this so we can maximize what we can do.

The day arrived. I prep myself in the morning shave, clean, smooth, put on a black French-style pantie matching bra, and my boy clothes. I packed my bag with outfits we talked about and some of my toys.

I get the message that they left. I head over there. I’m already leaking from excitement. I arrive. Max opens the door in a bathrobe he is even more handsome in person, in his early 40s, tall, muscular but not too much the type that stays in shape but doesn’t go overboard. He offers me some drink… but I cannot think of anything other than I need this man in me.

So I drop to my knees and take his semi-hard cock in my mouth. He gets hard fast enjoys the moment and tells me he just fucked his wife this morning, so I can taste her as well. I suck him for a long time… and he tells me to stop for now he has something he wants.

He wants to do watersports. We talked about it. We move into the bathroom and he drenches me. He puts his dick back in my mouth, still letting it go… I struggle, choke he lets up. I’m a mess now. But he is energized and jerks off onto me. He orders me to lick it up and take a shower and dress for him.

What a start of the day what have I got myself into…

I shower. Put on a pink set, and a flowery minidress. By the time I’m done he is dressed for work in a nice suit. I’m surprised… but he says it’s fine he will be back in a few hours. Until then I should clean and something else.

He tells me to bend over. I do it. He licks my bussy for a bit and puts a plug in. “I want you to keep that in until I’m back.”

I’m alone in his place. I look around there is really nothing to clean except the bathroom we just used. I do that and take a look… maybe I can cook something? There was nothing in the fridge but the kitchen looked like it’s not used at all.

So what else is there to do than look around in his wife’s closet? Her taste is very expensive all my stuff is cheap and these clothes were way out of budget for me and the shoes… So I just sat down and watched some TV.

About two hours later I get a text that he is coming. I hear the car pull in and go to the door. He was not alone…

We talked about this but I did not expect it on the first day. His friend James slightly younger, in his 30s tall, blue eyes that can cut diamonds, wide shoulders… he smirks.

“So you are the new toy,” I’m like ohh so he knows all things. I greet him accordingly with a playful smile and I ask Max: “What is the plan for the rest of the day, Daddy?” He likes that and says: “First let me see if you kept it in.” I show it and he is smiling.

“Then we are going to take turns on you until we feel like… go kneel in the middle of the living room.”

I do as I told. They both take out their dicks. I first try to take Daddy’s but he slaps me: “You stupid whore, guests first.” So I take James’s decent 15–17cm girthy cock in my mouth and Daddy’s in my other hand and service them.

But Max pulls away in a short time I don’t see where. Then he tells me: “Inhale a big one.” I smell the poppers and go numb. He pulls out a plug and tells me to bend over the sofa.

He puts his great cock in me and I have James in my mouth. This is great. When I get another whiff of poppers this goes on for a bit then they switch around. James is more gentle but again I’m a mush. And Daddy is rough on my face another sniff of poppers and I’m told to climb on James and ride him.

It feels nice. He is kissing me what is unexpected. Then Daddy tells me to stop and I feel him pushing his dick in next to James’s.

I don’t remember if at this point or just slightly after I cum so hard from the stretching I go full bimbo. I’m the toy.

They both enjoy their time with me and both want to cum in my mouth and I’m happy to enjoy the reward. I’m spent.

James says his goodbyes and tells Daddy that this was great hope to do it again. I don’t hear what is the answer.

After this Max makes me a nice bath, I put on his wife's bathrobe while he orders some food and we enjoy a quiet dinner.

That’s my story. My first day with him… and I didn’t even know yet how much more I’d give him.

I was a completely straight guy in my teen years, but around 16 I started watching porn more often then not and for some reason I always watched the guy and the cock instead of the girl, and I always timed my ejaculations to when the guy on screen would cum.

Skip ahead about a year later and I downloaded grindr (I know I was young but who hasn't downloaded a dating site at around that age) anywho I found a guy and talked to him for abit, he sent me some dick pics and he was abit small but hey this was the first guy to give me attention, I wanted to meet up with him but got scared (to young, might be trouble, could be dangerous) so I backed out.

About a year later when I was 18 I decided to try again, this time I wanted to be a top, I was very back and forth on what I liked and at that time I wanted a top, me and the same guy still talked so I told him to go down to the park and I'll meet him.

About 20 mins later I walk down there and he says "you can jump in if you want then you can fuck me" I said "um actually if it's okay I won't jump In your car, for safety" he didn't mind so I pulled my cock out and he sucked my cock through the car window...in pure daylight...midday haha, and there were a bunch of houses who could have seen me.

Edit: it's wrong but I was 18 he was 64

After that first time I liked it, but then the thought of having cock turned me on more, I got more and more adventurous, looking for cocks to suck and take till eventually I found someone who was nearby, I couldn't host and neither could he, we thought we were at a block, then he told me to meet him down the end of my road, I did and he picked me up.

I thought fuck he is hot and started sliding my hand up and down his cock while he drove, we didn't drive far, we found this open but in night private spot at a tree next to the highway, we kissed and made out for abit then he said "drop to your knees slut" fuck I was weak and did as he said, he pulled his cock out and holy FUUUCK, about 7.5 inches and girthy as fuck, I could barely take it but I told him to force it in me, he grabbed the back of my head and rammed his cock down mu throat, eyes went into the back of my head and I was slobbering, I loved the taste I love the sound I loved every inch of it in my mouth.

After about 10 mins (felt like an hour) of throat fucking he told me to stand up and take my pants off, again I did as he said, now I had played with my toy but I had never taken actual cock in my ass so I was tight, he spit on his cock and then rimmed my ass, I came a little on the tree, then he stood back up and I felt the head go in and I screamed, he grabbed my mouth and told me to be quite, as he said that though he pushed his cock in deeper and omg I just melted.

I pushed back on his cock like I automatically knew what I was doing, he grabbed my waist and pounded my asshole till I couldn't take it anymore, which was about 45 mins of straight doggystyle, I whimpered and groaned, but I loved every minute of it, he grabbed my throat and said he was about to cum, with a raspy voice I said "cum in me daddy, cum in your little slut" and boom I felt every rope of cum full my insides, he pulled out and ahoved 2 fingers in me pulled them out and showed me his cum covered finger "oh wow daddy that was a big load" I said as I licked it off

He dropped me back home and said "see you in a few weeks baby" now whenever I can I try to take his cock and be his slut, but nothing will ever beat that first time at the tree with him and that's when I decided to become a sissy

Hey girlies, if any of you have any question you wanna ask me to be afraid to message me okie, or even just chat about your stories if you don't wanna post them on here and just wanna tell me about them that's fine <3

*And moderator if this violates anything I'm sorry I didn't mean to I read the rules and I don't think I saw anything about getting others asking for advice, if I did miss it I'm sorry)

Hi everyone. I've shared a couple of my first time stories here before about my sexual awakenings when I was younger. You can read them on my profile. Here is one about my first time going through with actually taking a cock in my mouth. Hope you enjoy it!

This was a few weeks after I first experienced a porn theater at my local porn shop. My head was still wrapping around the memories of that day. The thrill of being lingerie clad, and exposed in the theater while two guys jerked and came on me like their personal cumrag, was amazing. It was so much masturbatory material that I hadn't even looked at porn for a couple of weeks.

I was home alone again on a Saturday night, still living with my parents in my early 20s. They had left for the night for a party and I had the house to myself, so naturally I threw on my lingerie as I always did and hit the interwebs. Exhausting the available porn sites as usual, without anything getting me off, I started fantasizing about the theater again, and how I wished I had gone further. I decided to hop on the yahoo chat room again and see if there was anyone local, or even if Bill was there.

After lurking a bit, a conversation was started by a man, I'll call Luke. He was looking for someone into wearing panties and looking to be his little cum slut. He was 47, over twice my age, and hosting.

I dwelled on it for a second and grabbed a bottle of vodka, and downed a couple of shots quickly, before replying. I said, "I know I could sure use a nice load on my face!"

He private messaged me not even 10seconds later.

"Hi there, my little cumslut. Where are you located," he asked.

I responded by telling him my rough location in South Bend, Indiana. Telling him I'm not able to host, but willing to come to him if he was willing to cum on me.

"Sounds perfect," he said. "How soon can you get here? I live about 5 minutes there."

"I just need to throw some clothes on over my naughties and I can be there in about 10 mins." I typed furiously.

He sent me the address and told me to come in the side door. I threw a zip up hoodie on and some sweatpants, grabbed my keys and bolted to the car. The vodka was just hitting my mind when I pulled onto his street. I parked a few houses down from his place, so that he couldn't see the car I was driving. Although it was late November and dark out already. I walked through the cold night air to his driveway and found the side door he asked me to go to.

As I approached the door he was already waiting inside. He open the screen door and invited me in.

As I walked into the kitchen, I saw a 47 year old daddy type. Dad bod, nothing spectacular, standing there in boxer briefs and nothing else. There was an outline of a huge cock in the underwear. I mean FUCKING HUGE! It was point up and almost around his left hip.

"Are you ready for this, my little cumslut," he asked, as he pulled his boxers down and let his hard massive member fold and flop out.

I didn't say a word or nod as I saw his, what had to have been 8" or bigger cock, fall out of his underwear. I immediately took my hoodie off exposing my black satin bra. I then turned around and bent over as I pulled my sweatpants down, exposing my black satin panty clad ass and fishnet stockings to his monster rod. I hadn't noticed that my own cock was falling out of my panties until I turned to face him. I noticed he saw it, and I looked down to tuck it back into my panties.

"Sorry about that, I said."

"No big deal. I didn't expect a real woman, when I asked you over, he said, as he walked toward me. He placed his hands on my shoulders and guided me down to my knees, where the head of his cock rested hanging down towards my chest.

I grabbed the long meaty shaft and pulled it upright towards me face so I could gaze and look upon it with marvel. I placed my right hand under he swollen cumsac and started stroking the shaft slowly with my left hand. He moaned with delight as I stroked and stroked.

"Spit on it, make it nice and wet babe," he demanded.

I conjured up a nice dollop of spit and drooled it out onto his shaft as I jerked. I then began jerking it with both hands as there was so much real estate to work with. As I jerked him with both hands I began pulling him closer to me, the head of his cock inching closer to my face with everyone pull and tug. It was within inches of my mouth and at this point I couldn't take it anymore. I opened my mouth and guided the swollen, pulsating head in between my drooling wet lips, and closed them around it. I moved it further into my mouth, feeling the head glide along my moistened saliva covered tongue, until it reached my uvula. I rested it in my mouth for a few seconds as my hands jerked every inch of the exposed shaft. I then felt and tasted my first taste of precum. I knew he was enjoying himself and getting closer.

As I continued to suck his head while jerking the shaft,Luke began thrusting in and out of my mouth. Pulling out just enough to pull strands of saliva out with the shaft, before sliding back into my gaping mouth. He had pushed a bit too far a couple of times, testing my gag reflex, which was not accustomed to a cock knocking on its door. I pulled back gasping for air, and spitting out a blob of saliva in the process, before grabbing his cock and engulfing it once more. I became ravenous for his cock. Furiously jerking and sucking it, now.

He moaned again, "Here it cums baby! Take it all slut!"

I pulled it out just as he let out a loud groan, and his cock let loose a huge shot into my face, impacting on the left lens of my glasses. Another shot had grazed my cheek and went past my head hitting the refrigerator door behind me.Then next few shots landed firmly on my lips, and the power left the load. The final drop drizzled down onto my chest as the cum on my lips began to drip off my chin onto my knees.

After Luke caught his breath, he thanked me, and grabbed me a towel to clean up. "No thanks," I said. " I want to savor the his moment." I let the cumsicles fall onto my bra from my face and stood up. I put my sweatpants on and my hoodie. "Thank you so much, daddy." I turned to the door without saying another word as he slapped me on my ass. I opened the door and giggled as I walked back out into the crisp air and headed back to my car. This was not the last time I'd run into Luke, luckily. 😜

Hope you enjoyed this memory as much as I do. I'll hopefully have more to tell again soon. Thanks for reading.

Recent fuck,first one bare!

I have always enjoyed older Daddies snd now that im getting g a bit older, its even more of an attraction. Ive been bi since taking my first cock as an older teen but have really been more into girls, but every now and then I get the urge to be a sissy for a guy. I met him on a swinger site and even though it is widespread in North America and Europe, he lived near by! We exchanged emails and texts then I met a him a few weeks ago at a wooded lot he owns and blew him. Yesterday he invited me over to.his place to fuck. His house is very private and we started on his porch. I wore a string bikini bathing suit under my clothes. He had me undress and model the suit for him then he turned me so my back was to him. He is Dominant in that he likes to control all the action. He started caressing my ass and nipples then my clitty. And then my breasts. He definitely is a tit man and spent a lot of time squeezing and pinching as he pressed his body against mine. He undid the strings and dropped my top. After playing a bit more he undid the strings to my bottom and let the bottoms fall to the porch deck and played with my ass again. I was nervous until he unzipped his jeans. Its been a LONG time since I was fucked. Daddy gets tested regularly and had shared the results with me, plus he hasn't played with anyone in a long time, so this was going to be the first guy I take bare and let cum in me. He didnt have any underwear on and for some reason the minute he unzipped I knew it was going to happen and all the nervousness disappeared. I was ready! Hes not overly long but atleast is bigger and thicker than me. I watched as he stepped out of his pants and pulled off his shirt. He then bent me over so that my hands were on his porch rail. He closed up behind me and played with my breasts again. I reached between my legs and played with his cock. I was ready and pressed back against him. He picked up on it and told me to lube him up. I took a tube of lube and smeared it on his shift and a bit on my hole then bent back over. My preparation and training with plugs and toys paid off as he was able to enter me easily. So here we were, naked and fucking on his front porch. He was good too. He knew how to fuck a sissy.

After awhile he pulled out and led me inside to his bed. He had me on my back and he was standing on the floor. He pulled me to him so that my ass was off the bed and my legs were in front of him and on his chest as he re-entered me. I knew from our conversations that this was his favorite position. He grabbed my wrist and forearms to pull me into him as he thrust. As he went, he pushed my legs forward, bending me further, to get maximum penetration. Too be honest. I was so focused on the fact he was going to cum in me that I really wasn't paying much attention to how I was feeling. I was moaning and he was grunting. I figured he was close so I reminded him no man had cum in my ass and I wanted him to take me, claim me, own me. I begged him to fill me. Thats what it took and he slowed his pace and forcibly thrust hard and deep as he came, pulling me further into him. I was his! His cum dump sissy whore and I loved it. After he came he stayed in me for a bit then pulled out. He helped me ease a bit back on the bed but had me hold my legs up. He got some wipes and cleaned up the lube. I wasn't expecting that but he was tender and caring as he wiped. He cleaned up some of my pre-cum i had dripped then cleaned his cock. He then helped me off the bed and back to the porch on my wobbly legs. We sat naked on the porch chairs and talked a bit..he said he very much needed this as its been awhile since he fucked anyone. He said he placed a good load deep in me and id leak a good bit durring the day. After a bit I got dressed and he walked me to my car. There are not a lot of guys who play in our area (like none) and I think we are going to be exclusive fuck buddies and I am looking forward to the next time!

So I made this post to find sissies as a Dom
And got a DM pretty fast, that this sissy bitch was looking for a blackmailer.
I was pretty new to BM but thought I’ll give it a try since I always love to tease and humiliate my sissy bitches.

We talked about limits and she sent me photos. Damn. She was sooo hot but still a closet bitch.

She told me she always wished to suck cock (especially BBC) but she told me she’s always been way to scared.

I told her we will get there soon enough if she stays a good girl and listens to everything i tell her.

Well she got locked, we had some sessions and since she only got sissygasms, ruineds and locked up orgasms there was no PNC.

She got further down the rabbit hole since she dropped more and more personal info and sent more and more pictures 😂😂

Well in the end I made her dress up and go to the local porn shop which has a glory hole.

She sucked her first dick there and loved it, ofcourse she did since she’s a sissy.

I made her go there a second time. She had her second BJ there and I made her walk home with the rest of a facial on her face in public lol.

Guess what? She wanted more and still was talking only about bbc here and there.

So she had to create a Grindr account, post her pictures and sort all out except the black dicks. She sent me pictures of the guys who are willing to meet and I told her who to meet and what to dress.

She got fucked by a strangers BBC outdoor and the guy even filmed it for her 🤭🤭

Now that shes a well trained slut she’ll have me over this weekend. I might dump this stupid bitch and look for someone else lol but I wanted to share with you guys how far and how fast you can go if you give away control!

Looking for fellow sissies but anyone is welcome :)

This is my second story. Writing about how it started from the very beginning. I'm keeping it short and brief. Every story coming from me is absolutely Real.

I was a teenager. No facial hair or body hair.  Under matured for my age. Tiny dick and had just learnt to masturbate. The person who opened me up to this new journey a Swim coach was in his late 30s or early 40s. Good physique. 7 when hard and dark complexion.

It was summer holidays. I went swimming every day after noon in a nearby swimming camp. They had several batches of 1 hour every day until evening. I usually went to noon batches. It was a huge pool with enough shower and changing rooms.. but then since it were holidays the pool would be crowded and few wud need to change near tall walls or trees.. which I kinda liked. I had found a place behind 2 water pump rooms where no one could see me change. I wanted a very secluded place because I didn't want anyone to see my tiny dick. So after my swim i'd take a quick shower and rush to that place. I would get fully nude. Then towel dry my hair and body. Wear clothes and leave.. this went on for many days until one day when I was drying my body standing naked i heard sounds from above the room and noticed one of the coaches or guards was on the top of that room plucking jamun fruits from the nearby tree branches. And he was looking at me.. out of panic i immediately wrapped my towel around and acted normal. When I looked back to him he was still looking at me and showed signs with his hands to remove my towel and show him my naked body.. at tat moment my heart rate doubled and don't know why but I did what he asked me to. I stood there naked for few seconds.. he signalled me to turn.. so I did and gave him a proper view of my back as well. Then I wore my clothes and left.. this continued for couple more days until he came to me and said - "come morning this Sunday. The pool will be closed for public and I'll teach you few techniques to swim easier". I knew wat this meant and I was very excited and couldn't wait.. During this waiting period i thought how all this happened and where it can lead to. He must have watched me don't know how many times and I'm sure he liked my slim hairless fair body with a tiny dick. I could not stop thinking what might occur this weekend. Finally wait was over and it was weekend. I showered and left. Reached the pool but the gate was locked. I asked the security guard there if the coach had come as he had called for weekend practice. To my luck he said the coach was inside and opened the gate for me. Don't know why but the guard gave me a weird look. Anyway.. I walked in.. the whole campus was empty. I couldn't spot him soon. Then saw him inside the pool swimming. He waved at me and asked me to get in.. I wore my trunks.. with a buldge as I was rock hard. And jumped in. He came near me and whispered in my ear, No one will disturb us now remove ur trunks and feel free. It was happening quickly.. he was rubbing against my thighs and I noticed he's fully naked.. woww.. I got naked too.. he humped me for a while caressing pressing my chest and ass.. he grabbed my dick and said.. it's so cute.. though it was tiny.  He guided my hand towards his dick.. he was hard and a real big one.. I loved it to hold and press his dick in my hands.. After sometime we got off of pool and he took me to his coaches room.. I immediately held his dick again and told him it's so big and nice. He said yes and that it was clean now to kiss it . I hesitated a bit but gave it a kiss.. He said- that's enough for you? Did u not like it? I replied yes and started to lick it.  Then as he said I sucked him.. then his balls too.. he then slowly throated me along side pressing my dick and balls.. he was about to cum.. he pulled it out and came on the floor. We got dressed and left.. no further talk. . Wow.. I wondered if I did something wrong.. anyway the stalking of me continued and we met again the very next weekend.. Everything was similar except we did few extra things.. He fingered me and inserted just the tip of his dick.  He sucked me like for 10 seconds.. it was heaven .. this time he fucked my mouth and came inside my mouth.. How this progressed into a Daddy sub relation is a story for another time.

It started with the day before my hotel reservation. I decided to fast for the whole day to make cleaning out my pussy easier for a full night of fucking.

The morning of my reservation, I shaved my whole body and lotioned. Once checked into the hotel I stripped and locked away my male clothes. The keys to the lock box was left in my car and it was parked as far as I could park it from my room and being within the hotel parking lot. I cleaned out my pussy to male sure any Daddy have a clean pussy to slide into. Then I got dressed. First the lingerie. Maroon thong, black thigh highs, black bra and fake tits. Then the makeup. I went with bright red lipstick, masquera, eye liner, green and blue eye shadow. Then I put on a see through, leopard print, minidress, black corset, heels and wig. I used a bondage belt to lock over my corset, and a set of heel locks to make sureI cant take off the heels and dress without getting the keys in my car.

Then I put out my add on Grindr. A sissy looking for fuck and go is what I was. No talking, no foreplay, just walk in to find me on the bed on all fours awaiting a good fucking.

My pussy was used by 7 Daddies that night. Most of it was a blur as o had some vodka and wanted more cock after each one finished. But the last one is the most memorable. A black Daddy big black 8 inch thick cock. He asked if he could breed me and in my horny haze I agreed. I met him on my knees at the door. He pulled his cock out and I sucked hard, slapping the back of my throat with its circumsized head. Daddy stopped me and directed me to the bed, where I got on all fours, face down ass up.

Daddy took his cock and pressed the head against my pussy. He was too big and my pussy was not ready for his massive cock. Slowly he rubbed his cock against my hole until my pussy started to give. And then it happened, the head of his cock pushed into my pussy. It hurt and my feet tapped the bed as my pussy was stretched beyond its limit. Slowly in and out he pushed deeper and deeper until his cock was burried balls deep and I could feel the base of his cock pushing my pussy as wide as it could go. Picking up the pace, Daddy fucked me harder and harder as I bucked and rocked with him. Every time he slide all the way into me, my pussy would ache at the big cock violating my hole. I lost track of time as his cock made me his bitch. He used the bondage belt to pull me onto his cock as he railed me. His pace quickened and before I knew it he was balls deep, filling my pussy and my legs bent up pushing his ass with my heels, encouraging him to keep his cock deep inside me. Daddy pulled out and left. My pussy started leaking his cum. I took a vibrator and used it to cum in my panty covered clit. Exhausted I passed out.

The next morning I realized I would be walking to my car with dried cum on my inner thighs, makeup all fucked up looking like a worn out whore. The walk was humiliating in the bright sun.

I finally got the nerve up to get some dick. I got a hotel and got dressed. Black bra and panties, thigh highs, heels, minidress, full makeup and wig. My heels were locked on and a corset was over my minidress with a locking belt over that. A Daddy messaged me and after chatting a bit, he was invited over. The door was left open and I cuffed my wrist and ankles together after blind folding myself and securing an open mouth gag. And there I was, on all fours awaiting my first Daddy to use my holes for his pleasure. The door opened and a chill ran down my back. Without saying anything Daddy stepped on the bed and slide his soft cock in my locked open mouth. I did my best to suck and bob my head on his cock. But he never got hard. For 10 minutes I did my best and I could not get him hard. He left unsatisfied and with the taste of cock in my mouth. The rest of the night I spent alone, unable to bring myself to invite another Daddy over.

Hello there cuties!

Let's start with that I don't know if I'm considered sissy. I'm your average guy, not even looking anything girly, even with my long hair, wearing average male clothes. On a street you wouldn't guess I might be sissy or anything.

So couple moths ago I bought two toys, one small around 10cm, really thin, easy to take and second one around 16cm, pretty girthy. From time to time I was using smaller one, because bigger was hard to take. And yesterday I somehow decided to use the bigger one. Started with just finger, then small one and for final the big one. It took some time but finally it entered, I slowly took it all and I came right away when it went as far as it could.

I felt really good tbh, like never before. It was first time feeling like that, but today I'm pretty confused how that happened. I read a little online and it say it's pretty hard to cum hands free especially for the first time. And tbf I don't even know why I wrote this, but wanted just to share it somewhere.

Have a great day sweeties ❤️

Last night, my mom came to talk to me to tell me that she had found my girl clothes. It has always been my absolute biggest fear that my family would discover my feminine clothes, but surprisingly, it went really well. My mom asked me questions in a super lighthearted, casual way, along the lines of: "Do you like dressing up as a girl?"...

She told me that if that was the case, it wouldn't change anything and that she would love me just as much. It really surprised me that she was so open-minded about it; it’s truly not the kind of reaction I would have expected from her. Granted, in the moment I panicked a bit. I said it was just something I had tried but didn't like—which is a lie—because I was just too stressed out right then.

So, my mom knows about my feminine side now, and it went pretty well. But now, I don't really know how to bring the subject up again with her. I would absolutely love to explore my femininity with her—have her teach me how to do makeup, have her buy me girl clothes, and be able to wear them when it's just the two of us at home...

I did it!

So I finally sucked a cock, swallowed his cum, and got fucked until creampie on the hood of my car and girlies let me tell you I didn't want him to stop. So I was horny as hell in chastity right? Well I got the idea to download Sniffles and stare at cocks as I edge maybe flirt and upload some pics to tease. Well I started to get flooded by messages and pictures of some absolutely mouth wateringly gorgeous cocks and one of them got my attention the most. We kept chatting and made the plan for in an hour. I shaved up, put my plug in, said "what am I doing" and ran out the door. I arrived at the meeting spot and saw him just relaxing. I parked, introduced myself and he immediately spun me around and started to rub his cock into me. He whispered "I want you to be my good girl" spun me back forward, pulled his dick out and asked me to warm it up for him. Girls when I say I dropped to the bottom of my high heels height, kissed the head, and took him into my mouth. I kept getting turned on more and more squeezing the plug in my ass as I made him moan and twitch. "Pop' just like that I felt the first pulse of him cumming onto my tongue while I kept sucking him until the pulsing stopped. He grabbed the sides of my head and hair and started to fuck my throat and I just relaxed into his thrusts and let this man use me until again he was shooting down my throat. I was so fucking horny at this point just moaning and bouncing on my heels and he asked me if I was okay with getting fucked. I nodded to him with his dick still in my throat. He picked me up and set me down on the car on my stomach. He felt my plug and cage and told me that's exactly how he likes his girls and I wanted to melt into the paint of my car. He pulled up my skirt, pulled down my pantyhose, spread my legs, pulled my thong to the side, pulled out the plug, and slow fucked his way into my lubed up pussy. My God he went from slow to hard in a slow burn that had my legs shaking and me trying to throw my ass as far back as I could on his dick. He suddenly got very focused, grabbed my hips and hit my girl spot like he wanted to get me pregnant and boom I can feel him twitching inside me and all I could do was giggle and grind my ass back and forth while he twitched. Ladies I thought this man was done but no he flips me over on my back missionary, grabs my hips and ass in a cradle, lifted me like I was a flower(which had me giggling and euphoric) and set me down on the hood. He told me to put my arms back to grab the hood and lifted my legs on his shoulders. He slid right back in like he owned the place( and he very much did) and had me moaning out daddy while arching my back up. Legs absolutely trembling and my ass cheeks making the sound of my total surrender as he fucked me to the point I thought I was going to have a sissygasm but alas he thrusted one last deep dive and exploded inside me again and I started begging and pleading for him to keep going just a little bit more I was so close and this man grabbed my face and told me I don't get to cum this time and I immediately felt my hips gyrating towards him with my legs ready to grab him but he told me to be good and that next time when he has more time he will make me cum like I need and I was already nodding that I want to see him again. He helped me up, told me to be a good girl and drive safe, then he walked off towards the field where his house sat. I pulled myself together, fixed my outfit, tried to fix my hair and said"fuck it messy bun it is" and then I felt some of his cum leak out of me and I felt whole. I got in my car, drove off and parked in my driveway while I type this encounter out still reeling from my first time being so fun. Be safe girls, find some yummy men to keep you full and the best thing I learned was even though I was nervous and excited I didn't let it scare me out of one the turning points in my journey and hope others find the courage to surrender yourself to what you want to try and experience.

Raeven 😘

Hey girlies! Just wanted to share my experience with you all. Been into this for a while now but just started to embrace it recently. Note: i am fairly attractive I would say, played sports growing up, but i barely ever received likes from attractive women when I had tinder. Today I downloaded grindr with some pics of me in some panties and got around 30 people messaging me already. I know some are probably bots, but the self validation is sweet. Anyway enough of me, stay girly and maybe put yourself out there🫣🫣

So I was hoping to update on the last guy from my story but he fell through and had to cancel. I was already dolled up though, full face of make up, chastity cage and belt on, plug in my pussy, garter belt, thong over the straps, my favorite oil slick black thigh highs(ended up re buying them 8 times🙈), my six inch platform stilettos, leather high heel locking straps, black pencil skirt, cute bra that matched my thong, my new white office blouse, black librarian frame lensless glasses, my hair up in a secretary bun, and my purse with goodies. I'd be damned if I wasn't going to do something hot tonight after all that effort. First thing was to jump on sniffies and start looking at the stocked house(perks of living in a city) and started to shoot some texts at some nice looking candidates and receiving quite a few promising looking requests. Narrowed it down to this younger guy that seemed so sweet and excited and tender towards me, now you see I started hrt over a month ago and the way this man is sweet talking me has me blushing, swooning, craving, and so safe. All while the hormones are shooting fireworks and static in my brain and pussy as I was getting hornier than I've felt before. Who knew a smooth guy could make a girl melt right girls lol? Well he was only 11 mins away from me and wanted to host me for the night and morning. I was so excited because I got some super sexy pjs delivered I had ordered online earlier that week and was down to cuddle him in them after he filled me to his hearts extent. He says let's do 1 am and I get the rest of my go bag and a change of guy clothes for the morning as quickly as I can because it's only 25 mins away from 1am. I shoot out the door in disguise with some super baggy clothes and a one piece doctor mask, hop in my car, drive over to the dark corner of my strip, hop out, pull off all the boy covers and straighten my outfit and hit the pedal. I make it there with 3 mins to spare and park out front of the address he sent and I can see the light is on. I text him I'm here with my butterflies trying to eat their way out of my stomach, hop out, grab my stuff and strut up to the house. I'm standing there expecting the door to open immediately and he would lead me in but no first 5mins go by with no reply. I look around a bit more now as it's dark and I'm in a strange neighborhood with no reply from my contact. I walk around the side a bit more and see it has a loop around back driveway and there are 5 cars parked there. I open the app back up and verify the address and it's 💯 the spot so I shoot a few more texts and wait about 20 mins as I ask what's with all the cars, is he trying to sneak me in, or what have you. I feel defeated at this point and get in my car and get a text. Well I too got excited and rushed to open the app and lo and behold it wasn't him but some guy that wanted me to let him free use me for a few nuts💦 at the rest stop 2 mi away from my current location and I was so dashed against the rocks I decided to say fuck it and let this guy use me like his whore. I arrived, got a text from him saying when I arrive find a blue truck with a bunch of stickers on it. Drove down the lot until I saw the truck, parked, walked up and opened the door. He was pantsless cock in hand and I immediately climbed in and started to suck him. I'm no pro at deepthroating or face fucking but I try to practice with my toys to help ease the learning process and felt confident when he grabbed the sides of my head and told me to relax my throat and let him fuck it. I gave it my best girls but my throat was getting bodied by this man and right as I was really tapping on him to let me up he locked me in place, plunged deep and fast for a few more strokes and finished in my throat. I was throbbing in my crotch for how hot I felt feeling all that cum in my throat as he slid out of my mouth and I flopped backwards against the car door trying to catch a break. I had almost no rest before he told me to get in doggy position against the door for him. So I flipped over, he pulled my thong to the side, pulled my plug out and tossed it on my purse. As I was just starting to tell him that I brought lube in my purse and anal lube applicator it was to no avail because he was already half way into my ass cutting my speech off like a switch. He did not go soft or gentle or slow but at his pace for his one purpose. As he rough fucked me against the door I was just trying to keep from losing my holding as he pulled out and shot a load on my ass and legs and got right back to fucking me for one more nut that I thought was going to join the last one but instead he held my hips and pushed as deep as he could before I felt him pulsating inside me. He pulled out, grabbed his phone and told me to get going. Slid out the truck with my purse, fixed my clothes and did my best to walk back to my car. I felt so hot walking back to the car because I could feel the cum on my ass and legs sliding down me and my creampie dripping out with each step. After I'm back in the car I get headed home because that was nowhere what I needed to get me off but fun none the less. I get back home around 220ish, crept back inside covered up, got to my stepmother's apt(essentially a entire floor to myself with 2 doors blocking the stairs), dropped my cover on the ground, grabbed my lube and applicator. Loaded myself up and grabbed my favorite suction cup toy. Stuck him to the wall, rubbed it between my ass to lube it and started to get the frustration out. I got the slow build up to pounding at the pace I love and got my sissygasm and kept going until I couldn't pump any more. Slid off my dildo, dropped to the floor, kicked off my heels and just sat there happy as I could be. After just soaking it in for a bit I finally got enough brain power back to get up, clean up myself and my toys, jump in my cute pj's, start my laundry, hit my bed, and let the girls know about my new like of being used on top of the ever growing mountain. Have fun out there girls, try to experience new things, and don't get too down if a boy ghosts you.

Raeven💋

I love making my sissy lock up in chastity only after she’s all dolled up. I try to make the scene as feminine as possible.  I'll have lavender and chamomile candles lit and hang pink tapestries across the windows. There’s currently a sexy picture of Jonathan Bailey hanging in our play room (he’s so freaking hot!!!!!). I’ll put on some girly music and open a bottle of wine. You get the idea.

This last time, I put on some Sabrina Carpenter because I had just helped Kimberly do her makeup like Sabrina. She was instructed to follow along with Jackie Wyers’ Barbie effect makeup tutorial (Absolutely love Jackie’s makeup knowledge so much). She did a really good job and just needed some help with her contouring. Then, I decided she needed some glittery rhinestones around her eyes to complete the look.

By this point, my sissy Kimberly had already taken a bath, shaved, applied my favorite Butterfly lotion (I love the smell and transformation metaphor xoxo), did her curly hair routine, put on her stockings, heels and dress, and glued on some French tips. She was almost my perfect girl. She was just missing that last key component for becoming my sissy bitch for the week. 

Her willing submission to me. 

I hand her the little pink Kink 3D chastity cage I got her for X-mas this year and tell her to lock herself up tight. I love watching her struggle a bit to do it with her new nails and overcome how turned on she is at this moment. I’m turned on by the idea of her looking down as she locks her clitty up for me, how she tries her sissy best to stay soft for me, how she has to lift her skirt up and pull her panties down, how she sees the cute white bows on her stockings sway with her smooth legs as she adjusts and imprisons herself, and how she is smelling the perfume and lotion I make her wear the entire time she is struggling.

She’ll sometimes flutter her long lashes at me with the worst frustrations, but I’ll just toss her a bag of ice and tap my riding crop. She always gets the job done for me in the end.;)

Once it's on, I take my necklace off and insert the lock, ensuring she is locked up tight for me. Then I grab her chin and pull her painted lips and doe eyes up to mine. “Who’s bitch are you?” I calmly ask her?

“Yours Mistress,” she always replies now as my perfect sissy as the key to her chastity dangles between my breasts.

“Good girl,” I tell her as I bring her in for a kiss and relish the vanilla flavor of her lips before releasing my grip on her chin and attaching the leash to her pink collar with “Good girl” written in sparkly, silver letters.  

For those that aren’t locked all the time, what are your fun rituals for getting locked into your chastity cages?

So I started edging to sissy porn early around 9 in the morning and the porn wasn’t enough I started looking at cock then gay porn then I ended up on Sniffies. I was practically begging to meet with any guy when one person finnaly agreed. His pictures had a huge cock and I was so excited but I was shaking and scared. When he got here he parked at the end of my alley and I got into his car and starting sucking him. It went from sucking to deep throating to riding. He ended up nutting in me and I cleaned up his cock. I even recorded when I sucked him off but only for two minutes. I’m excited that I’m finally pushing this boundary but also scared I might fully degrade into a sissy. Advice what to do now?

My first bj

Sharing my first sissy experience. I travel for work and live out my sissy side back in the hotel room. I usually just dress in the room but today I wanted more. I downloaded Grindr and started to chat with guys. The usual flakes and weirdos, it was around 11:00 at night and was about to give up. The Hilton I stayed at stopped public access at this time as well.

Then a new profile popped up that was 1 foot away then pinged me with the usual "Hey". We started chatting to find out we're in the same hotel just 3 floors above me. My heart is racing now. Talked more and ask for pictures. I packed a few outfits, panties, etc. Then he sent a pic of his cock, 7" clean, cut, trimmed, white.

Since I was planning this and wanted to be discreet I went to Walmart earlier in the week to get supplies for a DIY gloryhole. A shower rod and a dark curtain. My room had the perfect entrance where I was able to set it up. Then I cut a slit waist height and height for me to be on my knees. The lighting was perfect to where I could leave the bathroom vanity light on and everything else dark. I could see him but couldn't see me. I sent him a pic of my setup and outlined what I wanted and rules. He immediately asked what room number.

Told him I had to get dressed and setup my room. I slipped on some lingerie and a teddy. Put the gloryhole up and setup the room. Just the vanity light on, I went to the other side of the curtain and placed a towel down to kneel on. I was so freaking nervous and excited. I sent him my room number and within minutes I hear a light knock on my door. I unlocked the door with my app and he opened the door. I see him walk in and head towards the curtain. Undid his shorts and there it was a semi hard cock I make out through the curtain and hole. He slipped through the hole and as I good sissy I began to kiss and lick. He got harder and it was bigger than I thought.

It was now or never as I wrapped my lips and mouth around his head. He let out a moan of satisfaction making me feel better. I didn't know what to expect since it was my first time. It was softer than I expected at first. I twirled my tongue around his head. The taste was neutral, slight salt taste from his tip. I took in more in my more mouth as he continued to moan. I felt his cock getting harder and longer. To a point where I had to watch my teeth, I started to bob and he began to thrust hitting the back of my throat I gagged which he liked. Then felt the curtain brush open as he reached around to grab the back of my head which I didn't plan for but didn't fight. He thrusted harder and faster. Me trying my best not to gag or close my teeth.

I felt him start to tense then it happened, I felt his veins get hard against my lips and the hit cum start to pump. It hit the back my throat forcing me to swallow as he head the back of my head. After he finally finished cumming he let go of my head and pulled out of my mouth and though the hole. Pulled up his shorts and left. I'm still on my knees in the dark covered in spit. I eventually got up and cleaned up and proceeded to finish myself off. It was amazing

With my sister in college I use her room as my feminine space when I am dressing up. On one occasion about two years ago my parents were away visiting my sister at her college so I had the house to myself all weekend. I took the opportunity to be fully femme all weekend and play with my pussy as much as possible. Eventually my dildo just wasn't enough and I hopped on Grindr and invited a guy over who I had been flirting with for a while. When he arrived he was tall, well built and cute. I answered the door fully enfemme and was immediately on my knees and sucking him. Eventually we took things to my sister's bedroom and he fucked me. It was a lot of fun and I didn't think anything much about it after he left. A few days later he sent me a message and asked if I knew a girl named the same name as my sister. Eventually I confessed she was my sister and I was horrified that this guy knew my sister in real life. Turns out one of his friends had dated my sister and the guy I had over always thought she was hot.

I should probably describe my sister, she is very pretty, has strawberry blonde hair and has very large breasts. She also has a history of primarily only dating black men, which partly explains my own taste in men. We talked about her over Grindr and it got very hot and sexual about how he has always wanted to fuck my sister. This led me to order a strawberry blonde wig and tease him with photos of me dressed in her clothes and her old cheerleading uniform. A couple of weeks later I had the house to myself again and invited him over. He insisted on calling me by my sister's name and made me put together a slideshow of photos of my sister that he could look at as I blew him and he fucked me. At first I was a little weirded out by it but eventually I got fully immersed in the fantasy and got so turned on imagining myself as my sister and taking BBC like I know she has so many times.

This continued with him for a few months and eventually photos of my sister became a regular part of my sissy gooning routine along with sissy hypno and BBC porn. I've also done this with a few other guys since and it always makes it so much hotter for me. I've also done the same with my mom from time to time, as she is also very attractive and has huge tits like my sister. It is now at the point where I have hundreds of photos of my sister and my mom that I regularly use to pleasure myself and for black men to view as I please them.