Transvestite Stories

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Lady In The House Ch. 11

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

A few minutes later I was still in a daze, trying to rationalise to myself what had just happened. I was operating on automatic pilot, rifling through the drawers of my closet looking for a pair of nylons to replace the semen stained pair I was wearing when I heard the door to my cell rattle open and looked up to see the privacy curtain snatched open. Carmel...

Dick Sucked by a Tranny Hooker

by newamba on Sep 16, 2017
Humor & Satire

I read in the newspaper that Craigslist closed their "erotic services" section, which made me sad, because I've used it a lot to find prostitutes. For some reason reading about this reminded me of a particular experience I had with a hooker from that site. There was one night, just before Thanksgiving, when I couldn't find any prostitutes in my price range...

The Hitman Wore Heels

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

The well dressed man looked with disgust and loathing at the bum rummaging in the dumpster in the dark alley. Tony 'Tough Tony' Provalono had just left Scalini's, one of the best restaurants in New Jersey, where he had tipped the waiter more money than the hobo was likely to see in his lifetime. Tony was dressed in Armani; the gorgeous woman beside him in Pr...

How I Became Sissy Willow Ch. 02

by willow619 on Sep 12, 2017
Transsexuals & Crossdressers

"Now the preliminaries are over, and it's time for the entertainment part of our evening!" That was what Fern, my wife, said to me as I lay on the bed after I had been fucked by our newly mutual lover, Jason. I was dressed in pink panties, bra and slip, and a floral sundress. A blonde wig with long curls was on my head, completing the transformation. Fer...

Hot Summer Night at Jacques

by Mickytv200 on Sep 16, 2017
Transsexuals & Crossdressers

I sat on a red leather bar stool. To the world I looked like an attractive heterosexual male, wearing thin cotton summer slacks and a black tee shirt. I have sandy brown hair with bright blue eyes. My body is slender from running and swimming. I am about 5'11" and weigh about 160lbs. On the night at Jacques, I was about 30 though I look younger. My hair is l...

The Process

by desireethtttv on Sep 16, 2017
Transsexuals & Crossdressers

A few of my loyal follower's of Desiree's Hot To Trot Transvestite Adventures have asked me how I summon the nerve to be a cock sucking slut with a complete stranger. You see one of my earliest tricks in the annuals of Desiree was to dome light truckers heading down lonely highways. A glimpse of long shapely leg in a five or six inch heel generally was all...

A Special Night, Laci's First...

by Sissy_Chantel on Nov 27, 2018
Transgender & Crossdressers

Prologue: My name is Lawrence, I'm a young 40 something widowed white male, living a heterosexual life. However I have my feminine side, her name is Laci and as such I am a transvestite. I have preferred the long classical term of transvestite for a genetic male who dresses in women's clothes. But crossdresser also works as well. As a transvestite in my fu...

Arabian Nights Pt. 03

by MicheleNylons on Sep 26, 2017
Transsexuals & Crossdressers

"Only one word of advice I can give you; don't resist them," Sarina whispers into Michele's ear. "Thank you Mistress," Michele responds. "You won't thank me when they deflower your tight little arsehole," Sarina responds. Although obviously American she uses the English word arse, rather than ass. "I can't and won't help you once we are inside. You need...

Changes Ch. 01

by sublocked on Sep 25, 2017
Transsexuals & Crossdressers

I used to be a part-time cross dresser, male in every physical way, but dressing up occasionally for the fetish fun of it. But now I wear panties all the time and I don't even own male underwear any longer. Actually it's way more than that now, and I feel like I am not in control of my own life at all any more. The evolution toward this started abruptly, but...

Mandy Gets Her Man!

by easytvgirlmandy on Sep 16, 2017
Transsexuals & Crossdressers

One long hot summer a transvestite girl named Mandy was working away in a remote location on a project. There were positives and negatives to working so far away from home. The major negative was that she had no wardrobe at hand, except a well concealed bra and a pair of panties. Mandy used these to slip into in the bathroom and enjoy brief moments of the fe...