Sissy Caught Stories

167,051 results
Orientation
Length
Source
Infinite Scroll

Thrift Store Sissy

by sissywendi on Sep 16, 2017
Transsexuals & Crossdressers

A story by wendi marie st.clair She was looking at girl's blouses the first time He saw her. Of course, most of the world wouldn't have seen her as a "she" at the moment, but wearing her flare-leg, hip-hugging jeans that were obviously from the junior miss department and the androgynous purple t-shirt that showed that she shaved her body, she looked like a...

Jasmine - Sissy Slut Transformation Pt. 02

by BillyBaroo4you on Aug 31, 2020
Transgender & Crossdressers

A Sissy Boy Transformation (Continuation of Part I) Part II - A "Real Sissy Girl" Now Jazzy looked down at the table than in the mirror, then slowly began to apply her makeup, heavy amounts of it to get that bimbo presentation that Mistress wanted so bad. Sparkling hot pink lip gloss, she was wet by the thought of it. Pressing it to her lips, the butterfli...

The Dominatrix Order Pt. 02 Ch. 02 - Cuckold

by Jwwsmith on Jan 29, 2019
Transgender & Crossdressers

And so the days and nights passed at Johanna's home. With Sissy Slut gone, there were no slaves remaining who possessed any culinary skills. So Pomona took it upon herself to cook a fine breakfast every morning for Johanna, as a way to repay her for her hospitality. Pomona would wake early each day, fire up the wood stove, and cook a delectable meal of bacon...

A Weekend Away Ch. 02

by SluttyChrissy on Sep 14, 2020
Transgender & Crossdressers

Author's Note: Thanks for all the kind feedback & comments on chapter 01. This chapter does a lot to set up the rest of the story, so there isn't a ton of sex. Please hang in there with me and there will be much more sex in the chapters 3-?? I hope this one is sexy enough to keep you interested! ---------------------------------------- I'm not sure how lon...

The Cock Clock Ch. 04

by HarveyMarcus on Sep 26, 2017
Erotic Couplings

WARNING: The following story is for the entertainment of ADULTS ONLY, and contains descriptions of explicit sex. If you are not an adult, or reading sex stories upset you, or you are offended by subjects of a sexual nature - do not read any further! This story is for entertainment only. It contains adult oriented material. This is a work of fiction. The a...

Discovered at the Bar

by CrossdresserCaitlyn on Mar 25, 2019
Transgender & Crossdressers

It was 9 pm on a Friday night and I was just getting off work. It was a long day of running meetings and I really needed a drink. I was out of town and didn't know anyone so I decided to go to the bar by myself. As I sit down at the bar I take off my suit coat, untuck my shirt and loosen my tie and ask the bartender for a Jack and Coke. The first drink did...

The Dragon Ring Ch. 03

by Beatnic_jazzman on Sep 25, 2017
Sci-Fi & Fantasy

Three Fool me once shame on me, fool you twice...? I awoke in the early dawn. The sun yet to broach the horizon, but casting its rosy glow high into the cloud speckled sky. Sissy was lying across me; her head nestled into my shoulder, her arm curled around my neck, her hips across mine and her foot wedged twixt my knees. I reached over and smoothed her...

Young Master Ch. 03

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

"That's a good little, sissy. I told you that you could take the whole thing." I feel a sense of ashamed accomplishment as her smooth balls rest on my chin and I smell her intoxicating mix of pomegranate and a hint of musk as my nose crushes into her flawless, taut torso. This was the last time. It had to be. We couldn't keep sneaking around waiting for a ch...

The 70's Weren't All Care Free

by Stillherer on Sep 16, 2017
Transsexuals & Crossdressers

It was the 70's. Young, carefree, long-haired hippie, away from home, traveling around the country - having a ball. A couple guys I met and I decided to go for some beers. The local Y was in a sleazy part of town. So we ended up a pretty seedy bar which was hosting a rather bizarre strip show. At another table was an older guy that had been at the Y that aft...

Property of the Master Ch. 02

by BrightTightandWhite on Sep 26, 2017
Transsexuals & Crossdressers

"Wakey wakey sleepy head." The sound of curtains being drawn open was accompanied by a blinding light as my bleary eyes blinked open. "Wha... What? Huh? Hello?" I struggled to come up with coherent words as my brain wasn't fully awake yet. "Good morning Rosie, I hope you slept well," said the same voice as before. "Umm... Yes. Who are you?" I asked. "My...