Transsexuals & Crossdressers Stories

15,868 results
Orientation
Length
Source
Infinite Scroll

If Your Heart Surrenders Ch. 02

by PompousBuffoon on Sep 15, 2017
Transsexuals & Crossdressers

(Musical credit to: Ace of Base, "Don't Turn Around," written by Albert Hammond and Diane Warren.) Henry got out of Al's truck, taking care not to damage his 'Tin-Man' costume. He put his tin funnel back on his head and turned to see Charlie standing by his side dressed as the Scarecrow. After a moment, Al sullenly came stumping around the front of the t...

I Is for Irene

by BethanyJ on Sep 16, 2017
Transsexuals & Crossdressers

*** A series of stories with transgender themes which I hope will be of interest to those who like women, or would like to be a woman. Which includes me! *** It was all down to 'Jennie', really. If she hadn't reacted so clearly and positively when I'd suggested we should meet, things could have - indeed would have - turned out oh-do differently. I'd actua...

Jane and the Garage

by kenny69va on Sep 16, 2017
Transsexuals & Crossdressers

The day started like any other day Jane woke up, showered, dressed and went to work. During the morning she noticed there was a handful of new employees walking around the office. She had noticed that it seemed like the women all wore tight pencil skirts which showed off there asses and they were so short that if they bend over anyone near by would surely ha...

DC Transitions Ch. 01

by bittyrey on Sep 16, 2017
Transsexuals & Crossdressers

This is the first part of a story about David's transition. It includes descriptions of oral and gay sex, shopping, and political intrigue. If you like it, there's more to come. ***** July 2015 Sara and Alexis left their dates at the dinner table while they went outside to have a cigarette. Neither of them fit the Vogue or Cosmo ideal of beauty, but neith...

Andy to Amy

by JustPeekin on Sep 16, 2017
Transsexuals & Crossdressers

"Why are you staring at my knickers?" I jerked upright. God, I really had been staring at her knickers - not the ones she was wearing, sadly, but a pair on the floor, presumably yesterday's pair. They were perfectly normal white knickers with little pink flowers on them and a tiny satin bow on the front - unremarkable in every way other than they were right...

An Unforgettable Halloween

by JNBPUB on Sep 16, 2017
Transsexuals & Crossdressers

Tessa gets tricked at a Halloween ball but it turns out to be an unforgettable treat. * This past Halloween I took advantage of a chance to attend a charity Halloween ball. I had to travel for business to a city in upstate New York for a few days, and my first day there I saw an advertisement for an annual Halloween costume ball taking place in the mansion...

Amsterdam

by Many Feathers on Sep 16, 2017
Transsexuals & Crossdressers

zNote: This story evolves around a "shemale" so there is some bi-sexuality in the telling of this tale. If that's not your cup of tea, then please, don't bother reading it. Thank you. Amsterdam My wife and I had flown over from the states to visit with her parents who lived there. I had been there once before, for a quick brief visit so I knew a little of...

Scorned Bitch

by lyzunchik on Sep 16, 2017
Transsexuals & Crossdressers

"I'm assuming this is not entirely business," I asked Rod when I meet him for drinks after work. He's a fellow businessperson and we collaborate on some projects. I provide technical and consulting services that augment his contracts with various businesses and government agencies. "No, not really, but I thought it an appropriate segue to get you here fo...

Twin

by writedoctor on Sep 16, 2017
Transsexuals & Crossdressers

Paul stepped out from the refreshing shower and onto the plush dark blue mat, cool air meeting damp skin, his balls and pubic area tingling from the razor's close shave. Over the years he had periodically shaved down there, loving the nude, more sensitive feel and since the vacation in Bermuda, Paul maintained the smooth look. Gwen certainly had something to...

Three Times A Lady

by BethanyJ on Sep 16, 2017
Transsexuals & Crossdressers

"Er - is this for a man?" She surprised me. Elaine that is, the woman at 'Transform'. How the hell had she known? I mean it was really for me but I had to admit there was a man involved. About 35, slightly plump but well built. I didn't know his name but - yes, this was for him. But how had she known? I'd come into the store an several hours earlier and ask...