▲ 12 r/Sissy

All my first (meet/meet as sissy/dildo/sissygasm) <3😘

First meet- I was 16 and was horny and had no luck getting any women, I was bi but not out, so I downloaded grindr, found someone who could travel but I couldn't host, so I told him to meet me down at the park near my place (park was very open, anyone who stood on their back verandah could see me) he was a 75 year old man and when I went down to meet him he asked if I wanted to get in the car, I was scared too, so I told him no ill just stand here and he sucked me off till I came then drove away

First meet as a sissy- again was on grindr didn't have a car but someone was 189m from me so we chatted for abif and after awhile I went to his, he welcomed me in, showed me his room and then took his cock out it was decently sized (about 7.5 inches, very thick) I wasn't sure if I could take it but like a good sissy I told him to force me and that's exactly what he did, for an hour straight he held my head as he fucked my throat, I gagged and coughed but he didn't stop, when he was about to cum I begged for a facial and that's what he did, he held my face as I put my tounge out and he covered my face in his cum, I loved every minute of it hehe.

First time a took a dildo- I had bought a 10 inch dildo and hid it for about 6 months, never used it or anything, till one night I had the house to myself and went for a shower, lubed my bussy up after put the didlo on a chair and slowly inserted it into my bussy, it hurt at first but the more I lowered myself and bounced on it the more I loved it, I fucked myself all night, slept with the dildo in my ass and came on my hands and ate half my cum, the other half I used as lube for my bussy.

First sissy gasm- I was at my nan's and she was asleep, again opened up grindr to just get some cock pics and jerk off but I found someone 5 Meyers from me, it was my nan's neighbour, after I was sure she was asleep I went to his and we sucked eachother and fucked eachother, he was black so he had about 8 inches to him and fuck he stretched me open, after about 45 mins of being pounded he was about to cum, I looked back with hungry eyes and begged for him to breed me, as soon as I felt that first rope of cum fill up my insides I had my first sissygasm on his bed, legs shaking body shivering, my cock leaking all over the bed, my eyes rolling to the back of my head, I moaned and whimpered for about 4 minutes while he finished cumming inside me.

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u/sissyslave_07 — 10 hours ago
▲ 3 r/Sissy_Stories+1 crossposts

Hey girls <3

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)

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u/sissyslave_07 — 15 hours ago
▲ 29 r/SissyConfessionBooth+1 crossposts

My most recent master

So I was home alone one day and felt a tiny bit horny, decided to shave myself grab my 10inch dildo and bounce on it for abit, unfortunately it wasn't doing much for me, so I downloaded grindr again to see what's out there.

After about 10 minutes I got a message, "heyy baby, I love the way your body curves, think you could curve it on this" and then sends 5 pics of his bbc. I promise you girls I was drooling, but at the same time was abit sceptical, so I gave him my addy and said "see for yourself 😏"

7 mins later I hear a knock on my door and check grindr, it's him he told me he was here and I texted him, "walk in and find me" I was on the couch bent over face down into the couch, he grabbed my ass and I could feel his huge hands on it, (idk if anyone else can tell but I notice the difference between black men and white men when they grab my ass) but I could tell he was black and fuck it made me twitch.

I felt his breath close to my bussy and he said "fuck it looks tight, ever been stretched by a bbc before?" I went to reply but just as I said "ye-" his tounge was in my ass and I let out the most feminine moan I ever have. I felt his tounge deep in my ass and I loved it. After about 10 mins of him eating my bussy he grabbed my throat and said "mmm now your ready".

I was scared, I've had bbc before but if his pics where real then this would have been the biggest, and thank God they were real cause he put the tip in and I was ready to tap out, he hushed me and said "you told me you could now take it" and slowly pushed deeper, I was crying and moaning but I loved every minute, I thought he was balls deep cause he stopped pushing and I heard a groan, but he just said "this bussy is tight as fuck baby, I'm only halfway" my eyes shot open and I looked back and sure enough he was only halfway in my bussy

I was scared, about 5 mins later he was balls deep and I was pushing back on it loving every inch, I put my hand on my stomach and felt his bulge, that alone made me leak onto the couch, he treated me like a slut and told me to clean up my mess, while i was literally getting dig out by this monster I was also licking up the precum I had dripped all over the couch.

After about 30 mins of him pounding my bussy, pulling my hair, choking me, slapping me, calling me all sorts of names, he told me he was about to cum. And like a good slut I begged him to cum inside me, breed me, get me FUCKEN pregnant, and he was about to pull out but I pushed back and that pushed him over the edge, he grabbed my waist and shivered and jolted as I felt the biggest load ever explode inside me, I started cumming through my cage and i was sure I was having a sissygasm.

After he was done cumming he pulled out, grabbed my chin to look at him, as I did I got a glimpse of his limp cock, (still 7 inches soft🤤) glistening in my juice and his cum then I look at his face and he kissed me, told me to be ready tomorrow for round 2, this has been happening for about a month now, atleast once a day I get creampied and he says I'm the only slut he fucks, I wanna believe him but fuck idc if he shares his monster cock with others as long as I get that juicy load at the end of the day.....this sissy is happy

Love you babe's 😘😘🥰🥰❤️❤️

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u/sissyslave_07 — 1 day ago
▲ 106 r/SissyConfessionBooth+2 crossposts

My first time and how I became a sissy❤️

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

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u/sissyslave_07 — 21 hours ago

Public fun with stranger

So I'm not sure if anyone who reads this knows of the place but I live in ipswich and I was doing my shopping at a local market called booval and just before I started I decided to go to the toilet, while I was sitting there having a piss someone knocked on the stall wall next to me, I didn't know what was going on so I just replied with a simple "yeah" no question of "yes who is it?" Nothing like that, next thing I know the hanging toilet paper flys up and there's a meaty thick I'd say about 7 inch cock come from underneath, fuck I didn't think this is what was going to happen but fuck it hehe.

I grabbed his shaft and stroked it a little licked the tip, I Don't know how long he had been waiting but must've been awhile cause he had precum all over his cock head and fuck it tasted so good, I took him in my mouth and sucked his cock for about 5 mins, I thought he hasn't said a word so he might not be enjoying it, just as I was about to stop and walk out i felt a small drop of cum hit my mouth and was like "hmm okay" then BOOM 5 ropes of cum flooding my mouth, little groans from him, I stayed there and sucked his cock dry till he pulled out and waked away, never seen him don't know who he was but he tasted so good.

I wish I got a glimpse of him or what he was wearing cause I went shopping after and wish I knew who it was so I could give him my number and ask for a round 2.

Anyway that's my morning fun today hehe

Love yous xx

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u/sissyslave_07 — 1 month ago

Giving head while sleeping

I don't know If this is a fantasy or something else but I've always wanted to just go to sleep, have someone break Into my room and make me suck them off while I'm asleep.

I've had the role-play of it, I was looking after a friend's place and was on grindr, found someone with a thick 7 inch cock and before they parked I told them "doors unlocked, I'll pretend to be asleep just use me" and that's exactly what they did, I left my mouth open and they fucked my throat till they came.

it was hot but I can't get over the fact that I actually want to be asleep and get used, wake up the next morning with cum on my face and chest but idk if it ever will, anyway that's my fantasy

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u/sissyslave_07 — 1 month ago