Transvestite Stories

1,024 results
Orientation
Length
Source
Infinite Scroll

Life's What You Make It

by HYjaCK on Jun 7, 2020
Amateur

The first thing I see as I wake up is the blinding light coming through my curtains. Sadly, I couldn't afford blackout curtains due to my poorly-paying job that barely covered the bills, but I've slowly gotten used to it. I sit up and get off the sofa, stretching my back and neck. I also couldn't afford a large flat, so I had to make do with a single-room wi...

Open in Reader

Jake's Tales Episode 01

by JakeMorgan on Sep 14, 2017
Group Sex

The following is a true story, only the girl's names have been changed. I got to the Bel just after 4, having read Charlene's internet post and seen her IM message. I had IM'd her a couple of times and was looking forward to seeing her. When I got in I immediately noticed the complete absence of foot traffic - guys that walk repeatedly one theatre to the ot...

Mystery of the Friendly Prostitute

by Alluring_Crimson_Shifter on Aug 30, 2017
Exhibitionist & Voyeur

The Case of the Late Night Constable: Trafficker It is late at night. The male constable pulled up next to a sidewalk a woman was walking down. She looked fascinating. She wore a tight short dress, and a skimpy top. He could see the outline of her panties. The constable talks to woman innocuously, and she reasons he is not revealing why he is patrolling...

Caught Red Handed

by desireethtttv on Sep 15, 2017
Transsexuals & Crossdressers

With Halloween falling on a Monday, my wife Suzie was busy the weekend before trying to find her costume to wear to work. As a dutiful sissy husband that loves shopping as much as any woman, I tagged along, although our choice of stores to peruse is completely opposite. Suzie is a Goodwill addict, with anything at a bargain giving her much pleasure. Me, I'd...

Finishing School For Ladies Ch. 01

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

Chapter One -- The Beginning Valerie Swindon sat at her desk in her small study grading exam papers. A shadow fell over the opaque glass panel of the door and she looked up at the ornate mantle clock and realised it was time. She arose from her chair and came around to the front of her cluttered desk and unzipped her skirt. She caught it before it pooled...

Brazilian Discovery Ch. 05

by dan57 on Sep 15, 2017
Transsexuals & Crossdressers

By Dan57 and Riya with characters initially proposed by Jill York News from Brazil I recently received a demand for more adventures for Joan. At the same time, I also received a suggestion from Riya, an Indian expatriate with an unusual background. I decided to offer both of them to meet in Brazil. I haven't really planned a plot and will leave free rein t...

The Collector Ch. 04

by MicheleNylons on Oct 15, 2018
Transgender & Crossdressers

Chapter Four - Initiation Mary Pilson had been working at the Chez Ami for six months when Millicent Varity asked her to come in early one day. Mary finished at the shop and went straight home, washed, fixed her makeup, put on her cigarette girl uniform and got the first bus she could to the Chez Ami. "Come in Mary; close the door behind you," Millicent ca...

A Slut's Triangle Pt. 15

by Kantarii on Sep 19, 2017
Transsexuals & Crossdressers

My whole body is trembling as adrenaline courses through my veins. My ribs are hurting and I'm scared. Face down on the pavement, it's everything that I can do to shield myself from Kryss kicking me again. Just hearing Brenda's voice echo through the night air gives me a glimmer of hope. There are plenty of things in my life I take for granted, but my frien...

Caught In the Tranny Master's Web

by CarrieQ on Sep 16, 2017
Transsexuals & Crossdressers

One of the nicest things about living in London's West End is how you can look out of your window at all the glitz and glamour, and feel like you're right in the middle of something big. And if something as big as Kurt's 14-inch cock happens to be pounding in and out of you while you look, then doesn't that just take the biscuit? An over-endowed black Germa...

Kristen's Cum Party

by Marlene on Sep 12, 2017
Transsexuals & Crossdressers

I have this girl that I just adore named Kristen. I think that most man and most woman (even girls like me) look for that sexual soul mate that they just click with. Someone who loves sex in any and every fashion. Someone to whom the word “kink” means simply anything that they can think up that might be fun where sex is concerned. Kristen’s my girl. She love...