Chastity Tranny Stories

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A Tranny Virgin No More

by Creamyirish on Sep 12, 2017
Transsexuals & Crossdressers

Fantasy became reality for my gal, Tranny G. She has finally started to come into her feminine persona. She has more confidence, is buying more outfits, and when she leaves HIM at work, she comes home and dresses. She starts with wearing short skirts and cami's, then sexy lingerie at night. She began playing with make-up and based on tips I gave her by e-mai...

Letter from Frost Haven

by justincbenedict on Dec 11, 2018
BDSM

Dear Shoeblossom, Enclosed is a journal I kept after hiring a dominant couple to supervise me for a period of time. I actually first read about Sergei and Kyrsten from "Letter from Maui" and was determined to meet them and hopefully hire them. And it was financially quite steep! And, Sergei and Kyrsten were fun and lively, but they were a tough pair. (I ca...

Recruiting of a Sissy Maid Ch. 14.5

by Sissy_Chantel on Dec 16, 2017
Transsexuals & Crossdressers

Readers, I am adding another quick short story of tranny girl Bailey hungry for men and cock. Inserting this story between Chapters 14 and 15 of "Recruiting of a Sissy Maid". I hope you all enjoy it. ***** Title: Another T-girl Bailey out and on the Prowl for Men and Cock Story Friday night, I've been feeling a desire to dress up as Bailey all fucking day...

TS Madison Simply Rocks!

by Samuelx on Sep 16, 2017
Celebrities & Fan Fiction

African-American porn legend, amateur Rapper, YouTube sensation and all-around brilliant entrepreneur Brian Pumper smiled smugly as he slid his long and thick ebony dick into Lethal Lipps tight butt hole. The big-bottomed, caramel-hued porn starlet with the infamously thick, luscious lips and ever-hungry pussy purred contentedly as Brian Pumper's big dick fi...

Wife catches husband doing what!?

by Storymaster252580 on Jul 14, 2020
Fetish

Jeff and Lauren have been married for 3 years now. They met in college and dated for 2 years before eventually getting engaged and married. They are a fit and active couple always going to the gym. Jeff is 6-1 200 lbs and has a six pack and is packing a nice 8 inch cock. Lauren is 5-5 130 lbs with nice perky C cup tits and a firm round ass that gets all the...

The Virgin Tranny & the Bride Ch. 02

by yano on Sep 25, 2017
Transsexuals & Crossdressers

This is part two of a confession related to me by my transvestite friend Roberta, and like the first part, is so sexy without any further elaboration by me. Having seen some of the photographs, I can only say that she strays very little from the truth. Meantime I am trying to convince her to let me publish a few on the Internet. Watch this space. Exactly tw...

Sissy Gets His Wish

by Tinydickthongboy88 on Sep 18, 2017
Transsexuals & Crossdressers

I should've guessed something was up when my boss Victoria winked at me on our way into the office. She's about 5'9", 130lbs, she just got a boob job last winter, and as she walks by her ass bounces in the sexiest way I've ever seen. Work started normal enough. Our company was in the testing phase of software for a military application. I wasn't clear on i...

Mistress Chantel, Tranny Dominatrix Ch. 02

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Two: A Day in the Life of Tranny Dominatrix Chantel Waking up into another morning where this transvestite dominatrix gets to dress up and enjoy her life of toying with sub men and sissies/crossdressers. Working hard to get my femme look down over the last couple of years prior to operating this Dominatrix business, I enter my very lady-like powder...

My Babysitter Ch. 03

by GreenGale on Sep 11, 2017
Transsexuals & Crossdressers

Getting forced down, a big, fat cock shoved down my throat. I was choking on it, I couldn't breathe. Oh, and another one, ramming my ass. It felt so powerful, and I felt powerless. These things never last though, and before I knew it, I was awake. I opened my eyes and there was the most beautiful woman to me, Annabelle. Well, that is if you consider her a wo...

An Expensive Addiction

by NeverGuessWhatsNext on Sep 12, 2017
Transsexuals & Crossdressers

I don't consider myself gay. I am a bisexual who happens to love tranny cock, and only tranny cock. Other than that, I have a girlfriend and am more than happy fucking girls. The whole tranny thing started in college, and to be honest I don't really remember how or why...I just started watching tranny porn and thinking it was hot. I was a pothead and drank a...