Shemale Mistress Stories

27,874 results
Orientation
Length
Source
Infinite Scroll

Punished in Paris

by maia24 on Sep 16, 2017
Transsexuals & Crossdressers

Maria the very pretty Irish transvestite had arranged to meet the men in Paris. She had agreed to be taken to a house in the suburbs to be punished, abused and sexually defiled by a number of men. She was dressed in a purple mini dress and wore very expensive lingerie. She was totally smooth and as she walked to the avenue to meet one of the men she was full...

In Service to my Mistress Ch. 01

by Aprils_slave_marie on Sep 25, 2017
BDSM

This is an absolutely true story taken from my life's journey as a Transsexual slave woman. I've lived full time for over twenty years now. -------------------------------------- As I write this my Mistress is in the bedroom with one of her many Black Bulls. Her screams of lust and orgasm reverberating through the house as he grunts and thrusts himself int...

Melissa's Ordinary Day Ch. 09

by Floydman1 on Jul 30, 2019
Transgender & Crossdressers

"Giséle" awoke, feeling weird just like she had the morning before. But it wasn't just that she didn't have headphones that was off. Her bladder was full and as she rolled over to get out of bed, her dick was pulled down almost painfully by some hard casing on it. The previous day's events began to return to her, and as she padded quietly to the bathroom,...

Dick World

by darkness_drearing on Dec 25, 2019
Bisexual

For contributors As was stated at the top: while there were will be two general threads to go off of (for a guy and girl), feel free to create your own characters or scenarios. The only shared premise among them needs to be that they find themselves, however you decide that happens, in this universe and, as The Eagles would say, "You can check out any t...

Open in Reader

Shemale Fun

by orangemaestro on Sep 26, 2017
Transsexual

You are a good-looking man in your mid-twenties. You are 5'10, 170 lbs., and in good shape, with some muscle definition. You have always considered yourself a man's man, but lately you have developed a curiosity about women with...something more. When you fantasize, you sometimes find yourself imagining a cock between the girl's legs. Pretty soon, that's the...

Open in Reader

Judi's Fantasy

by Bi_Siamese on Sep 12, 2017
BDSM

When I got home I could hardly stop thinking about the wild night with Judi. I didn't even care if my wallet was empty. I was going to work plenty of overtime that next month to make up for it. Judi gave me specific orders not to call her but she would call me whenever she was not busy. About two days later on Tuesday after work I got a call from Judi who wa...

Blossoming Shemale Ch. 02

by TheTitLover on Sep 25, 2017
Transsexuals & Crossdressers

This is inspired by:http://www.literotica.com/s/reluctant-shemale tawnysuede's Reluctant Shemale if you enjoyed it, I hope you'll enjoy this series. * * * My name was James. It was, before everything that happened, anyway. I'd come from pretty good stock, as the snooty, upper class would likely say. I guess I still did, although it would take a DNA test to...

The Society

by Barno on Sep 19, 2017
Transsexuals & Crossdressers

I met her during the summer. I was only nineteen and working to save some money for college. I had been raised by my grandparents who had both passed away over the past year. After the burial costs I was far from wealthy. My parents weren't around so I was on my own at a young age. I had moved a couple of towns over from where I had grown up and was living i...

Matrimony

by Writer345 on Jul 15, 2020
Transgender & Crossdressers

Do not try this at home! And don't read it if you are under eighteen years old as it is a story written for adults and not kiddies and contains words of a sexual nature that you will misunderstand. Although this story is set in the same Universe as my 'Making Dreams Come True' stories and features some of the same characters and locations, you do not need to...

When Sara Met Bob Ch. 05

by yellowfrog on Sep 14, 2017
Fetish

Bob remains the love of my life, the fountain of my admiration! Handsome beyond words, virile and composed, sexually insatiable in many ways, Bob has become what every woman wants - in addition to her own husband, of course. In the intimacy of our extra-marital affairs I enjoy massaging his prostate, deeply and slowly, my fingers moving very deliberately to...