Transsexuals & Crossdressers Stories

15,868 results
Orientation
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Infinite Scroll

How to Love a Strong Black Woman

by Samuelx on Sep 5, 2017
Erotic Couplings

The first time I ran into my cousin Sammy Charles, I didn't recognize her. I was visiting my family members in Orleans, Ontario, but I lived in the town of Nepean at the time. The slim, dark-skinned young Black woman with the braids came to the door and gazed at me curiously. I stood there, big and tall and Black. The name is Thomas Jean. My friends and fami...

Walt Pt. 02: A New Beginning

by AngelaK on Sep 14, 2017
Romance

2005 24-25 yrs. Old Ch. 1 - The first Date I enjoyed being fucked hard, and occasionally, roughly. I even enjoyed mild 'discipline'. I could handle someone using a riding crop or belt on my ass for short periods. I was pretty freewheeling when it came to sex. I wanted it frequently. I experimented my new found gender freedom with as varied a group of sex p...

Inescapable Pt. 02 of 02

by optimizer888 on Jan 29, 2018
Transsexuals & Crossdressers

It took close to an hour to get the hair ready. Every morning. I always had to take a shower - most girls didn't wake up each and every day with cum in their hair. Shampoo and oceans of conditioner. I only went to the salon once or twice a week. Most days I'd have one of my 'sisters' help me blow dry it, usually Anong. If they were too busy, though, it took...

Attorney Client Privilege Bk. 05

by Bazzz on Sep 14, 2017
Interracial Love

24 Lis hung out across the street from Nikki's apartment building for over an hour. She knew that the short haired brunette would be finishing a "matinee" as the girls called it and should be home by 4 or 5pm. A "matinee" was the term the girls used for a late lunch rendezvous with a client. Sometimes there was actually a lunch involved but most times it wa...

Family Issues Ch. 05

by allthatisfuta on Mar 6, 2018
Transsexuals & Crossdressers

Sorry that it takes so long but finding time to write is not always easy. I would like to thank Madison (ThanatopicFolds) for all the time invested. Your red pen is the string that holds the story together and prevents it from falling on its ass. I also want to thank all the nice people who wrote me and encouraged me to keep going. On with the story. $$$...

Pink Panties

by DrLuverotica on Mar 27, 2019
Transgender & Crossdressers

It all started with a pair of pink panties. It was sometime after midnight when Jo arrived home from being on-call at the local hospital. She'd received a phone call several hours earlier about a bleeder and had to rush in. Recently her workload had become almost unbearable, but we needed the money so she was working her sexy curvaceous ass off. By the ti...

Stepdaughter's Transexual Surprise Ch. 1

by juge1 on Sep 19, 2017
Fetish

I've been through two marriages in the past. My first wife died at an early age of 29 from a massive heart attack and my second marriage was a nightmare from hell, that I'm now free of. When I met Jeanie, I knew I had to take it slow and easy. Jeanie was a very nice lady in her early 40's. I myself was a few years older. Jeanie had two lovely girls. I had...

Crossdressing, Piss and Sex

by Lovinhose on Apr 14, 2020
Transgender & Crossdressers

This is a work of fiction, a fantasy that I would love to come true. It also contains 'pissing' (aka 'watersports'), crossdressing, and a crossdressers sex with men, so if you are not into these subjects, this story might not be for you, you have been warned. Also, comments are welcome, but please note, I'm NOT a professional writer, if I was, I wouldn't be...

A South African Lesbian Orgy

by Samuelx on Sep 12, 2017
Interracial Love

I simply love Black women. I think Black women are amazing. There, I said it. My name is Anne-Marie O'Neill. A young white woman of Irish descent with short dark brown hair and pale green eyes originally from the City of Boston, Massachusetts. Way down in the United States of America. At five-foot-ten, with short hair, tattoos and a cigarette always at hand,...

High and Low Ch. 03

by bisexualsmoker on Sep 12, 2017
Fetish

Brenda really wasn't happy. Here she was aimlessly wandering around West Hollywood on a wild weekend that had lasted two months. She was going to go back to her apartment in Long beach and get her head together. Many men and women couldn't help notice Brenda as she strolled along though. With her sexy spike heeled strut, with her incredible ass cheeks almos...