Transsexuelle & Crossdresser Stories

809 results
Orientation
Length
Source
Infinite Scroll

Girl's Night Out

by tgirl_Mary on Sep 14, 2017
Transsexuals & Crossdressers

It was shortly after I had returned from a trip to Las Vegas. I had not seen my good friend Matt in over a month so I called him up to talk to him about the trip and show him some pictures. Although we still trained together weekly for karate we hadn't been out for a while and wasn't sure if the "thing" we had was bothering him or not. The "thing" was a ni...

Dream Date

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Who would have thought it; I was reduced to finding a partner on the Internet? I had read about these dating web sites and though dubious I found one, completed my details and waited. A few days went by and I heard nothing. I waited a few weeks and still I heard nothing. I turned to an old girlfriend for advice. I'd known Julia since school and though close...

Caught by Kyle Ch. 01

by MzDeviancy on Sep 16, 2017
Transsexuals & Crossdressers

My stories tend toward the nonconsent/taboo side, but I want to be clear that I'm in no way suggesting that the acts in my stories are okay. Forced sex is a fantasy I enjoy and I write for other similarly minded people. Real rape is ugly and sad, and if it's something you're considering acting out you should seek help. * Alright, longest disclaimer ever, b...

A College Sissy Ch. 02

by nat_rose on Sep 26, 2017
Transsexuals & Crossdressers

When I woke up the next day I was hit with guilt and shame. Bo was gone and I laid on my back, staring at the ceiling. I was dressed in the white silk nightie, and the pink bra and panties from the night before. My ass was sore from the pounding and my face was caked with leftover makeup. I felt bad physically and emotionally and so I started to cry. This i...

The Robertson's Sissy Ch. 06

by Clite69 on Aug 20, 2019
Transgender & Crossdressers

**A quick note. The chapters of this story can fall into multiple categories, group sex, reluctance/nonconsent and transgender/crossdresser. If any of these are not your taste than this story may not be for you.** ***** I woke a few hours later, my eyes swollen from crying, irritated by a mix of tears and last night's make up. I was alone, Lela must have s...

The Doll Maker

by Fibaro on Jan 22, 2020
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** (This story was one I wrote and posted on Halloween. It's a bit more gruesome than my other works as a result.) *** Intro Carl had always been different, he was a quiet somewhat effeminate looking boy, taking mainly after his mother. From an early age he had loved playi...

My Mother's Boyfriend Shawn

by JHouston on Jun 18, 2019
Transgender & Crossdressers

There was a knock on the door to my room, "Come downstairs. You are drinking and playing poker with me." Shawn commanded. Shawn is my mom's boyfriend. He is a white 48-year-old 6'2" tall and athletic former-jock that grew up as a spoiled rich kid. He has never worked for a living and lives off of his grandpa's trust fund. My mother, Gina, and I moved in...

Afternoon Delight Turns into More

by TammyPanty on Jun 5, 2019
Transgender & Crossdressers

How an Afternoon Delight Became Much More I was born into a large trust fund and had the good fortune of never having to work a day in my life. I would always have as much money as I needed and could do whatever I wanted. As it always is in life, when something good happens there is always something on the other side of things that happens to level things o...

The Whole Nine (West) Yards

by PhRedSonya on May 20, 2019
Transgender & Crossdressers

Chapter 1 - Caught by Renee My name is Brandi and this is my story of getting a whole lot more than I bargained for. Eight months ago I was a happily married computer software consultant who worked out of his house, while my beautiful wife of 3 years worked downtown as a manager in one of the many corporate offices. Since both of us worked we enjoyed a very...

One for the Team Ch. 06

by MicheleNylons on Jun 1, 2020
Transgender & Crossdressers

Chapter Six -- Smells Like Poison May 1986 Mrs Frobisher turned out to be a rather attractive forty-something matron who exuded suppressed sexuality with her tight skirt and jacketed business suit, long legs, stiletto heels, red hair and milky-white skin. Detective Sergeant Archie Sanders fell in behind her breathing in her scent, his eyes locked on her Ru...