Transvestite Stories

1,024 results
Orientation
Length
Source
Infinite Scroll

Mistress Melody's Wanton Evening

by RobinTVDaniels on Aug 18, 2017
Fetish

Mistress Melody had become my mistress recently and I was very deeply in love with her. Melody is not that tall but is a very sexy black woman with long braided hair. Her dominant personality was over six foot tall though. I was a transvestite submissive sissy and I was her total slave. We both knew my little 4 inch dick would never satisfy her so she had...

Forced Entry

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Danny sat at the bar of the Holiday Inn nursing his fourth double scotch, espousing to the man beside him the reasons why his company was the best designer and distributor of accounting software in the world. Danny was a large man in his forties and was running to fat. He was dressed in a travel-weary navy-blue business suit, a crumpled white shirt now open...

The Business Trip

by Scotsdude on Aug 18, 2017
Fetish

The plane journey to London was uneventful, a bit choppy, but otherwise fine. I decided to make my trip a working holiday and convince my boss to give me the following week off. Two days for the World Travel Market then twelve holiday days. It would be the last year at the Earl's Court venue, which was a shame; I always enjoyed it there. But anyway, to work...

Transvixen Tranny Rock Band Ch. 07

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Seven: Panti Love - Michelle Lust 'So how did Panti and Phil Benson get together?' Michele pondered as she sat in the back of the limo being driven to the Bocca di Lupo restaurant for her date with Tony Carlotta. Well it came about as follows... After the second concert Panti lay on the park bench gratified and sated having had sex with two strang...

The Virgin Tranny & the Bride Ch. 06

by yano on Sep 25, 2017
Transsexuals & Crossdressers

WOW!!! As I rewrote this episode the sheer sexiness of the occasion was so powerful. Another episode from Roberta before he went off to California on vacation. The following week was fraught with difficulties, none more so than my inability to contact Jodie. Calling her mobile on my way to and from college was always met by the message that it was switched...

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...

Barrack Room Betty Ch. 04

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Four - A Night at the Flicks Michele was confused; she didn't like Leading Recruit Jason Jones one bit, he was a bully but he was also handsome, strong and actually quite intelligent. She knew he had a thing for her as soon as the Leading Recruits made the grommets crossdress, and of course last night he had ejaculated in his pants when he was span...

An Exploit as a Paid Whore

by Marlene on Sep 12, 2017
Transsexuals & Crossdressers

I’m submissive by nature. Big surprise huh? I think most girls like me (I’m a transvestite) are. It’s funny but before I really got into the whole dressing scene and I lived most of my life as a guy I wasn’t all that submissive. In fact I remember being a little above average in the dominant thing. I think that most of us (transvestites, crossdressers...

Undercover Angel Ch. 04

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

Michele blinked as the flash went off in her eyes. "Ok; one more photo, and this time keep your eyes open for me luv ok?" the man behind the camera said. Mike had done some research before he had ripped off Tony Leonardo and he had located a man named Harold Brown who could produce good quality counterfeit identity documents. Harold had agreed to provide M...

From Heels Fetish to Cock-Sucking

by heelsfan1980 on Sep 16, 2017
Transsexuals & Crossdressers

It is with a sense of disbelief that I take my clothes off. It's like I'm watching someone else do it through my own eyes. I don't want to, not any more, but I'm here and he's left me alone in the room and I don't see what else I can do. I'm taking it a step at a time. Yes, I can put on the clothes I've brought with me in the rucksack. I've come a long...