Sissy/trap story thread since last one got 404'd
Sissy/trap story thread since last one got 404'd
Adrian Morgan
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Owen Garcia
Anyone wanna hear my first time with a guy?
Nathan Cooper
Please!
Leo Bailey
>I was 16 and at the time and had been dressing up two years prior to that
>I was watching sissy porn and hypnos for awhile now when and the urge to please a guy became stronger
>I didn’t know what to do until I found out about the Craigslist personal ads
>I looked on the m4t and was super turned on. There were so many guys wanting to fuck sissies!
>I responded to one of the ads from a guy in his late 20s who wanted a blowjob from a cd
>we ended up chatting and exchanging kiks
>We then started to really get dirty with me sending pics and videos and him sending pics of his cock and is shit you not to this day it was the biggest cock I ever had
>He was 7inches uncut but super thick. I almost came from the sight of it
>I told him I really wanted his dick in my mouth and he replied by asking when and where would work best
>I was so nervous but my horniness washed away my anixety and I told him Saturday at a motel nearby
>Until then I kept sucking a a really thick cucumber and fucked my ass several times to his pics but I made sure not to cum
> If I came at all before meeting him I think I wouldn’t have had one of the best experiences of my life
Ryder Ortiz
i know it's not a story but i posted myself as a whore online gagging and choking on a dildo... do you like it?
xhamster.com
Evan Harris
iron666maiden69 skype slave
Adrian Gutierrez
sauce
Isaac Campbell
Lifelong (closet) sissy. Very first time I dressed up for a guy was this hot & very fit black guy I met on Craigslist. Both of us bi with women in our lives, but wanting this. Went over to his place (nice place!) in guy mode with a backpack full of girly things. Talked a bit & got down to business. Was nervous, so it started out as more of a strip show. I laid out a black lace bra & matching thong on his sofa, garter belt, stockings, heels, a babydoll top, pearl necklace, silver clip earrings, and a blonde wig. Proceeded to strip out of my guy clothes in front of him & start dressing & turning myself into a sissy. His pants came off, revealing a huge, shaved, cut cock with Prince Albert piercing. He stroked himself as I (now fully fem) posed & danced in front of him. Eventually, I end up on all fours, almost subconsciously presenting my ass for him. Felt his big dick slide up against my hole as he came up behind me & started fondling my body. I’m in absolute heaven now. End up on my side & feel his finger slide into my ass. He starts finger-tucking me, while stroking my cock through my panties. All the while, thoughts going through my head: “omg - I can’t believe I’m actually doing this”, “I’m having gay sex as a sissy & loving it - omg”. I came almost instantly. He still wanted to go. Switched positions, him sitting on sofa and me kneeling in front of him. Sucked my first cock that day & loved it! He pulled me up so that I was straddling his lap, his cock against me ass, rubbing up and down outside. My arms around his shoulders, his around my waist, we start to kiss & make out. I’m lost in sex at this point & loving it. He ends up lifting me up, gently laying me on my back on the floor, spreads me legs & positions his cock at the entrance to my hole. Condom - yes. Lube - yes. I take his cock in my hand and guide him in. Tell him it’s my first time. Felt amazing as he slid into me, filling me & rubbing up against my prostate
Jason Murphy
...continued...
He’s ducking me (gently) now & I’m thinking to myself: “omg, This is the best sex I’ve ever had...I’m totally gay”. That thought put me over the edge & I came again. Moments later he did, too. Pulled out of me, took off the condom & shot his load all over my stomach, chest & sissy clit. It was hands down the most intense & exciting sexual experience I’d ever had. We got together regularly for about the next year or so & still chat on occasion. He helped bring out the sissy in me & it was amazing!
Mason Watson
When I was a kid my friends forced me to dress up like a girl and be their girlfriend. Theyd make me wear my sister's old clothes and theyd take me out on dates and do kissing to me and put their penises in my mouth and butthole.
It was so embarrassing. My sister would laugh at me while I wearied her panties and frilly ankle socks and skirt. And people would thinked I was a girl when theyd take me out
Jace Ramirez
...
Daniel Reyes
sauceeee
Brody Scott
Bump
Henry Green
bump
Julian Morgan
Can you greentext what you actually did with him
Ploxx
Jaxson Butler
Not too much of a story except I'm about to be locked for a long time
Feel free to make it longer, in fact I'm begging you
Pic is me
mobile.twitter.com
Leo Cruz
1/?
>be me
>get into hypnosis porn, and by virtue sissy hypno
>be in relationship with girl but openly bi, never explored it
>relationship ends, decide its time to try guys
>kinda scared to start so get into chastity in order to get super horny and willing
>spend 2 weeks locked, I'm dying
>chat with some super big dick hot dudes online who like sissies
>most are closeted dudes who only like CDs or want to try
>no interest in my dick, want to treat me like a girl
>this really turns me on oh fuck
>one dude organizes a hotel room and gives me a time to arrive
>i pack up and head out
Brody Sullivan
2/?
>have had lots of experience anal toys, deepthroating, gaping etc but nervous
>already shaved super well, get super dressed up, pic related
>guy sends me ETA updates by the minute, I'm so horny
>laying all dressed up on a bed with hypnosis playing on the TV
>I've been in this trance before, it's exactly like it should be, I'm totally limp in a cage and dressed up like a sissy
>theres a knock on the hotel room door
>i'm ready
Daniel Allen
Go on
David Ward
Looks painful.
Angel Gray
>my date is a mid-40's white guy, very handsome
>i lay down on the bed and he sits next to me, we both take a couple sips of liquor i brought to loosen up
>ask him to feel how soft my shaved tummy is
>his hands find their way over my ass and panties
>I let out a soft moan and he smiles and chuckles
>take some pics and videos of this
>he takes off his pants and I can see a cock thats substantially bigger than mine precumming a spot into his underwear
>he pulls down my panties and my limp clitty pops out and I pull my legs up a bit
>he softly opens my legs back up and grabs my locked dicklet and lightly squeezes my balls
>i let out the most sissy moan I"ve ever made and he rips his underwear and shirt off, lays down on the bed
Evan Scott
Go on and show some more pics
Julian Thompson
Here's the videos i took so you can watch and listen...
>his dick is super clean and well shaved, 7.5" with balls maybe 50% bigger than mine
>i take it in my hand and roll a finger up the shaft and a huge drip of precum rolls out of the head and down my hand
>instinctively shoot my tongue out and lick ALL of it up off my hand and put the head of his cock straight into my mouth
>he starts moaning as I milk the building precum into my mouth and swallow it as quickly as it comes out
>slowly start pushing it farther and farther down my throat
>his balls start to bob up and down, so I grab them in my hands and gently massage them
>quickly find myself pushing my nose into his stomach, with his cock hilted in my throat as he lightly bucks
>I lightly gag as he's balls deep in my throat, bouncing up off and and gasp
>a string of precum is hanging off my chin
>I'm panting and tell him to get inside me
>I lay on my back and he spreads my legs back to completely expose me
>he squeezes my ass and runs a finger over my hole
>he drips some lube over his fingers and enters me
>even his fingers are bigger than mine
>just like a girl, he curls his finger straight into my prostate
>a drip of precum forms on my locked cock head as it twitches, limp
>I'm moaning and panting and tell him to get a condom on and fuck me
>"fuck me daddy"
>I've never said that before...fuck
>he rubs the head of his cock briefly over my lubed asshole
>I tell him it's so big
>I beg him to give it to me
Zachary Johnson
sorry forgot the video
xtube.com
Justin Barnes
>be me 24, gf 23
>get into sharing
>find an older guy much bigger than me
>lasts longer too
>he dominates my gf
>makes her his sub
>starts telling gf my cock is worthless
>convinces her to cage me
>tells her he wants to go further, make me his sub too
gf and i seem unsure but when he's got his dick in her he knows how to get her to agree to pretty much anything
Henry Smith
Would like to find a sissy to fuck one day
Austin Nelson
thats super hot, you should do it. I'm trying to get into couples play rn for that some reason. Very fun.
Forgot counting but...
xtube.com
>he pushes his dick into me
>I moan and it fills me up super deep
>he starts out with slow long strokes and quickly picks up the pace
>grunting, he sends his cock into me hard enough for his balls to audibly slap against me
>he slides out, grabs my hips and turns me over
>pulls my arms backwards and rails the fuck out of me from the back and I whine and moan
>after a while he starts to get a little tired so I tear the condom off and aggressively start throating his cock again
>his balls start to tense up and his cock head starts to flare so I know he wants to cum
>tell him he can cum in my throat if he wants but please keep fucking me
>tease him for a few minutes until he rolls on another condom and lays me down one more time
>his pace picks up almost to the point where I can't take it
>limp clitty flopping around and he grabs my balls and squeezes them
>calling him daddy, can't even think straight, beg him to cum on my face
>he loudly moans, throws off the condom, and sends a huge stream of hot cum all over my locked dick and stomach
>immediately start spooning it up with my fingers and swallow almost all of it before he even finishes cumming
>splay out and we both laugh because it was really fuckin fun
>"call me"
VERY fucking fun time, would definitely recommend if you're into this and on the fence. Just be safe and find decent guys to do it with. I've been fucking a lot of girls recently and it's been very nice to explore my sexuality, definitely made me way better in bed too. I want to fuck more older guys but have gotten away from the sissy thing a bit more, just like the feminization thing and panties/stockings. I'm sure I'll find another guy again sometime soon.
Charles Davis
What does a prostate orgasm feel like? i wanna try it