Sissy Caught Stories

167,051 results
Orientation
Length
Source
Infinite Scroll

Another Submissive Slut Ch. 04

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

She was leading me unerringly to my place. How did She know where I lived, I wondered briefly before the effort of walking with such a large plug in sissy hole forced my attention else where. Panting more from nerves than the walk I quickly opened the door to the building to get us in and off the street. Almost immediately my landlady was upon us. I nearly s...

Story of Sissy Blackmail Ch. 01

by richysissy34 on Sep 13, 2017
Transsexuals & Crossdressers

I have been debating writing this up for a while, but it truly is a really hot story, that I figured you would all enjoy... so enjoy! (And yes, the title does speak for itself; it's a true story...) ***** I began cross dressing when I was 16 years old, and I am now 21. When I was 18 I moved away to college, and began living in a dorm on campus. I chose to...

I Admit I Was Speeding

by Cute Little Thing on Sep 16, 2017
Transsexuals & Crossdressers

I admit that I was speeding, when the cop pulled me over. What can I say, I was rushing to get home. I get that way when I have panties and a bra on. But let me start at the beginning, because this is a long story. It was a Friday night and I had been saving up all my courage for a month, since my girlfriend had told me she would be going out of town for the...

A Shell of A Man

by uppishcarrot on Sep 13, 2017
Transsexuals & Crossdressers

Six years ago, I was doing well enough to finally afford my dream apartment. It was a studio apartment on the upper side of town. So, I had the job, the apartment, the money... but I was lonely. Very lonely and very horny. Not only would I get all hot and bothered from looking at all of the pretty women at work, but there were also plenty of hot women who li...

Sissy's Special Night

by mdw_dark_angel on Sep 17, 2017
BDSM

This girl was so excited as Master had agreed to a special surprise for sissy from angel. Master took sissy to work and came right away to fetch angel to return Home and ready things for angel's surprise..."Sissy's Special Night". Y/you see, this slave has belonged to Master... though one has not always retained one's physical collar... since Master first c...

Sissy Cuckolded by Girlfriend Ch. 01

by SaraRurik on Sep 16, 2017
Transsexuals & Crossdressers

My name is Josh and I'm a 19 year old white guy with a beautiful girlfriend. Her name is Angel and she is the best thing that has ever happened to me. I love her with a passion and intensity that is hard to describe, she is everything a man could ever ask for and more. She is caring, sexy, understanding, kind, intelligent, and totally a bad bitch. We have...

The Vacation from Hell Pt. 01

by JamesMiehoff on Nov 27, 2018
Erotic Couplings

Copyright (c) 2018 James Miehoff, All Rights Reserved. This work may not be published whether for fee or free without this copyright. --------- This is one of a series of stories set in what I call Universe-J. Universe-J is very much like this universe with a few exceptions. First the people tend to be a little more sexual and less hung up on sex that...

Neighbourhood Terror to Sissy Pt. 11

by Fibaro on Jul 2, 2019
Transgender & Crossdressers

Chapter 13 To Mark's huge relief he witnessed Lisa opening her shorts. Without the tight fly holding the dildo in place it would fall out, at least if Lisa hadn't taken a hold of it to put it neatly back on Mark's night stand. Lisa took off her shorts completely and her panties along with it. It was instantly clear that her neatly trimmed pussy was soppin...

A Night For Romance

by maggie2002 on Sep 14, 2017
Romance

The night was beautiful as only spring nights can be when winter loosens its harsh hold and the soft winds blown and flowers grow. "Damn, I'm a poet and I didn't know it," laughed Sissy Littleton the Editor of the Littlestown News, as she sat at her computer trying to come up with a short story as filler for the Sunday Magazine. She had to be done by tomor...

Caught In Lingerie

by hicutlover on Sep 26, 2017
Transsexuals & Crossdressers

I was driving home from work and all day I had been extremely horny. I had unbuttoned my pants and was stroking my cock in my purple nylon thong. I loved this thong. I could see the outline of my cock and the shape of my cock head in these panties. It was making me harder. All day I had been fantasizing about taking a cock in my boypussy and couldn't wait to...