Sissy Life Stories

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Infinite Scroll

Tales of Sub Asian Sissy Ch. 04

by subASIANsissyJADE on May 6, 2019
Transgender & Crossdressers

(Thanxxx so much for taking the time to read me stories! This is just my fourth post and I'd absolutely love any feedback... also, please feel free to reach out if you just wanna chat with a very depraved and submissive Asian sissy) ***** Dave threw my dress at me. "Hurry the fuck up, you stupid slut. My wife gets home in a couple of hours and I need to cl...

Sissy College Ch. 03

by MasterJW on Sep 11, 2017
Transsexuals & Crossdressers

Standard disclaimers apply. I'm indebted to Puzziboi for writing the first half of this chapter: Thank you! I really do enjoy your feedback, so please keep it cumming! Lastly, I encourage you to read the previous chapters before you delve into this one. Mr. Blackwood slapped his large veiny cock against Lenni's smooth lily white face with an audible smac...

Subliminal Obsessions Ch. 02

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

*Before... She settles into a rhythm hard, steady, deep, hitting my spot inside as I moan and watch the flasher as it shows high speed pictures and all those words and phrases. Sissy. slut, bimbo, be a girl, be calm, be happy, suck cock, be happy, get fucked ne happy, sissy, slut, bimbo, live for men, live for cock, be happy, be a girl, be calm, be happy,...

Sissy Pills Pt. 02

by Sissyhalo1 on Jul 6, 2020
Transgender & Crossdressers

There's nothing like waking up like this. This being after being fucked. Not fucked but riding a dildo until you have a sissygasm. And yet that's not the first thing in my brain waking up. It's the cum. It's that eating my own cum. And really feeling this need sort of burned in my brain from the semen and the pills. I really, really want to suck a co...

A Picture Perfect Sissy

by meeah sue on Sep 16, 2017
Transsexuals & Crossdressers

"Holly, hold your breasts up. That's it honey. Squeeze the nipples between your fingers. Make them hard for me, sweetie." Jason lifted and pushed his soft breasts together, squeezed the small dark nipples, and hurriedly looked up to see if what he was doing was okay. He really wanted what he was doing to be okay. It was dreadfully important to be okay. Kare...

Young Master Ch. 01

by smittysimon on Sep 11, 2017
Transsexuals & Crossdressers

It was supposed to be the best day of my life...and maybe it was, but definitely not in the way I planned. My 21st birthday...my first day as a man, as a true lord of the Manor...my first day as a Master. I was so nervous I threw up my lunch. Not very manly, I know, but just the thought of having my very own sissy to play with had me teetering between the...

Sissy's First Day

by whispy_sub on Sep 13, 2017
Transsexuals & Crossdressers

Sissy let out a disheartened groan as he closed the classroom door. He looked down despondently at the discipline demerit clutched in his gloved hand, "It's my first day and already I screw something up; I can't believe this." It was only his fourth hour here at the Academy, and already he recieved a demerit. He wasn't quite regretting his decision to enrol...

Breaking with Traditions

by Canadagander on Sep 17, 2017
Loving Wives

Copyright © 2005. All characters, events, and text in this story are purely fictional, and are created by and the sole property of the author. All rights reserved. - - - - - - - - - - - - - - - - - - - - - - - Writer's Note: It's time for Canadagander to make a public disclosure, to come out of the writer's den, so to speak. 'Gander is not a real person....

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

A Perverse Plan

by Candyboi on Sep 25, 2017
Transsexuals & Crossdressers

It started off with little things, small suggestions, that quickly snowballed into perversion. My wife Carla, who for the first decade of our marriage displayed little interest in kinky sex games became a hot wife virtually overnight with total control over me... Carla is 44, has a very curvaceous ass, 34DD tits, and works as a doctor at the local hospital....