Transvestite Stories

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Rewards: A BDSM Transvestite Story

by Sateema Lunasi on Sep 17, 2017
BDSM

Liam would wait hours if she commanded it. He belonged to her. Her wish was his command. The straps were beginning to hurt, but not unbearably so. He hated these lackies she ordered to whip him. It was all for amusement, a test to her. She wanted to see how far he would go, what he could take. He was a strong man and could take quite a lot. There was no wa...

The Moulding of a Transvestite

by HugoTrevelian on Oct 15, 2017
BDSM

The Moulding of a Transvestite Preface. We have a mature bisexual cross-dresser with a very submissive side, by day he is David, post office worker. By night and weekends, he turns into 'Jak' a classy T-Gurl, she has arranged to meet a mature bisexual assertive male. This is a full account by Jak, a mature bisexual male transvestite of the first meeting w...

Doing Three Ch. 3

by Royal_Prince on Sep 12, 2017
Fetish

Chapter 3: Transvestite And no I wasn't hard. The minute I stepped out of Angels car dressed like a woman I lost all sexual feelings whatsoever. All I could do was think "what if someone saw me." The only good positive thing about the whole incident was that she was kind enough to take me out of town to do our "shopping." Now for the hard part. She was a...

Carla & Jerry: A Girl Story Ch. 01

by Marlene on Sep 14, 2017
Group Sex

Lots of you read my stories in the Transexual/Transvestite sections of the site. So I thought I'd expand my horizons and do a few girl stories. I have a friend of mine named Carla. She's told me a lot about when she was in her late "teens and early twenties" (you need to know that the folks from Literotica are very paranoid about under age stories—they've ne...

My First Threesome

by Biguy007 on Sep 1, 2017
Group Sex

The first threesome I had started as a fling with a local transvestite. Dave and I were having a drink, just socially, and he bought me a couple drinks, which I tried to politely refuse, just because I felt bad that I was broke and didn't want to take advantage of him. He jokingly told me not to worry about it, so long as I promised him my first gay encounte...

Jasmine Takes Charge Ch. 03

by DesireeFox on Sep 15, 2017
BDSM

James/Mistress Jasmine: Husband of Desiree, some time Transvestite Jasmine Desiree: Wife of James, Submissive to Mistress Jasmine ~~~~~~ Saturday, we arrived at the Gorean Compound just after two pm. Mistress was complemented on her slut by everyone that we met. Even dinner went well, Mistress seemed to be coming around as she asked "Des, when did you g...

Jasmine Takes Charge Ch. 02

by DesireeFox on Sep 15, 2017
BDSM

James/Mistress Jasmine: Husband of Desiree, some time Transvestite Jasmine Desiree: Wife of James, Submissive to Mistress Jasmine ~~~~~~ Sunday morning after our time at the Dungeon Mistress was going through my clothing. "Slut you do not have much to wear, we will have to go shopping" I was a bit perplexed, I had two full walk-in closets of clothing and...

She-Male Cream Ch. 1

by Anal Slave on Sep 12, 2017
Fetish

Well it all started when I was about 18 I lived in an area that a lot of transvestites lived and hung around. Some of them you couldn't tell if they were male or female unless they had their clothes off. My first encounter with a she-male went like this I was driving down the road and I looked ahead and they were the prettiest woman I ever saw hitchhiking....

Self Service Ch. 05

by prickasso on Sep 12, 2017
Illustrated

It was 3 weeks since the party where I performed in front of 2 dozen transvestites, sucking my own cock until I came. After that, Sonja, one of the she-males had propositioned me to film this as an instructional video for a porno company she worked for. I had just received an e-mail message from her company saying they would pay me a pretty good figure for a...

How I Became A Filthy Tranny Slave Ch. 02

by beyondkink on Sep 13, 2017
Fetish

This is the continuation of the story "How I became a Filthy Tranny Slave" where a young man who lives out his fantasy of dressings as a transvestite and being defiled is abducted Ch. 02: Tranny Slave Is Imprisoned When I woke up from my drug induced coma it took a few minutes to adjust and analyze my new setting. It feels like I had been out for days, pos...