Transvestite Stories

1,024 results
Orientation
Length
Source
Infinite Scroll

The Billy becomes Billie Story

by Grey Eagle 286 on Sep 13, 2017
Transsexuals & Crossdressers

William Johnston read the notice again very carefully. It was posted on a Cross-Dressing Internet site he visited regularly. When he noticed the message on several more sites, he read it. Bill was not an active cross dresser or a transvestite but the idea fascinated him and had for several years. The ad read: Attention Young Men: We are offering a wonderfu...

David to Dee Ch. 02

by kinkymaid on Sep 25, 2017
Transsexuals & Crossdressers

Author's note: This is the second installment of Dave's transformation. At this point, he's been found out by his girlfriend Gina, who, after looking through his apartment, discovered his stash of fem apparel, and has decided to fulfill his fantasies, as a way to become closer to him. At the same time, she's discovering that she likes to play his games, and...

New Mother, New Life Pt. 02

by Cara_Elaine on Sep 13, 2017
Transsexuals & Crossdressers

I stayed at Helen's that night, both of us in her bed wearing nighties, occasionally stroking and comforting each other. I fell asleep in her arms with my face buried in her bosom. The connection I felt with this person was sublime. When I woke the next morning, I went to the bathroom to find her in the shower. She was truly a remarkable sight. Her blonde h...

My Wicked Ways Ch. 06-08

by SEVERUSMAX on Sep 18, 2017
Group Sex

As we sat down for breakfast (which was leftover pizza), I found myself playing footsie with Josie, who seemed to be rather thrilled with my attitude about her estranged husband in Montreal. Then again, my perspective wasn't really surprising, given that I was Jewish and didn't particularly care for Nazis, Aryan types, or skinheads in general. I think that s...

Train Wreck

by daedfish on Sep 14, 2017
Loving Wives

I'm sitting here somewhat confused, with a gnawing sensation inside that something just isn't right. I can't articulate it really, but it's there still eating at me. Sometimes you just know when something is off. Right? I'm not making sense, let me explain. I just went to my wife's office to drop off her phone that she left at the house. No I didn't see som...

Jack and Mary Nobbled Pt. 03

by Clare_Ca_2 on Sep 15, 2017
Exhibitionist & Voyeur

Chapter 48. It was around 2 O'clock in the AM: Shift work coupled with snow made Jack later than usual getting home - not to mention the blisters on his ass-hole that caused walking to pose a real bind to his getting around lately. Mary was sleeping: Zonked-out on pills and booze. They hadn't talked that much since the incident, and there was a large, cold,...

A Strange Romance

by toniukcd on Sep 16, 2017
Transsexuals & Crossdressers

Although I was over qualified after I graduated and accepted a one as an Internet operations officer for one of the high street retailers. I was offered better jobs but I took the one with the retailers because it paid reasonably well and more importantly meant that I would have to relocate down to the East Midlands. Ever since my parents decided when I was...

The Only Difference is the 'S'.

by Otazel on Sep 16, 2017
Transsexuals & Crossdressers

I agreed to do the late shift because it suited me. My wife had run off with a neighbour, leaving me with a pile of bills to pay, and as a result all I was doing in the evenings was mooching about watching the television and seeing off cans of lager. So the chance to start work at four and finish at midnight for a twenty percent pay rise was welcome. And tha...

Tranny Chasers: Shirley and Chrissy

by 1946EW on Sep 12, 2017
Transsexuals & Crossdressers

Shirley looked around as she entered Cavalier d'Eon, hoping to spot Ron and Bernie. She had promised that she would be there, and fully expected them to be waiting for her. Her survey caught the eye of many a hopeful tranny chaser. She had not known of the breed a week earlier, now she could spot them with ease. And there easily were over a dozen or two at t...

Christian College Sex Comedy Ch. 33

by FinalStand on Sep 25, 2017
Group Sex

*Children must face the scrutiny of their parents* *I have many people to thank for this chapter; readers who kept in touch, Steve and Shawhollow for editing and about a half-dozen feedback artists who told me what I was doing wrong and what more I had to add to a make the story work. Thank you all.* (Yes, this tale is supposed to be somewhat humorous and...