Crossdressing Bet Stories

66,523 results
Orientation
Length
Source
Infinite Scroll

Becoming Dannii Full Time?

by seams_straight2me on Sep 5, 2018
Transsexuals & Crossdressers

Mia and Linda had kept their word. Two large framed pictures of my Dannii photo shoot were delivered, and had I not been there when the pictures were taken, I would not have believed that was me in those pictures. Linda had done a fantastic job with those pictures. One was a solo portrait of me, my tits squeezed together, lips looking inviting in a moist red...

Gender Change: Magic Closet

by Zekar on Jan 26, 2017
Fantasy

There is magic in the world. Narnia was just the tip of the iceberg when it comes to the magic that a wardrobe or closet can do. You find yourself directly in the crosshairs of such a magical encounter. Whether malicious or benevolent, that is up to you... This is merely the introduction to a much more interesting tale. (Dear reader, if you like this story a...

Open in Reader

Anime ENT

by akikuka on May 16, 2019
Exhibitionist & Voyeur

They always confused people around them of their true genders as their appearance and figure contrast their true physical self regardless of their claim. It doesn't help that most of them wear female clothing to further add our confusion(and our sexuality). They are called Traps, or Tomgirls if you will. Having the beauty that brings girls to shame, these tr...

Open in Reader

Halloween Party Aftermath

by Sabnock on Oct 19, 2020
Transgender & Crossdressers

Oh my GOD I'm so hungover. I creak my eyes creak open, and immediately regret doing so. Everything hurts. My head is pounding. My mouth tastes like something died in it. I try to sit up, pause, flop back onto the couch. At least I've got blanket. Wait... I'm not in my bed. Where the fuck am I? I rub the back of my hand over my eyes, feeling a weird, heavy...

The Slut Couple

by kin1041 on Sep 30, 2019
Swinging

The Slut Couple is inspired by the cover art (made by Chromosomefarm from Hentai Foundry). The idea of a slut couple was interesting and I liked the idea of couples getting into sexy situations but coming out of it still together if not a little twisted at the end. Something like borderline netorare and such. So before we begin; who's the couple?What's next?...

Open in Reader

Be My Bitch

by purekink on Aug 20, 2019
Transgender & Crossdressers

I'm so glad you agreed to be my slut – I've been searching for a crossdressing hussy I can train to be my personal tart for some time now, and I'm certain I can teach you to fit the bill. I understand your fantasy is to be dressed as a sexy sissy and have your manhood and your cherry fucked right out of you. This pleases me, as I enjoy nothing better than u...

My Neighbor's Submissive Ch. 01

by marissacd on Nov 27, 2018
Transgender & Crossdressers

Chapter 1 - Exposure They moved in next door shortly after we bought our house about five years ago, a nice couple who were a few years older than my wife and me. My name is Michael. I'm twenty-eight years old, white, five-seven, brown hair, blue eyes and a lean build, suitable for cycling, which I do a lot. My wife, is five-four, slim, athletic and blonde....

Lipgloss Dreams Ch. 01

by lipglossdreams on Sep 12, 2017
Transsexuals & Crossdressers

I suppose that my story starts in the same way as a lot of other crossdressing boys with busy real lives: year after year of bottling things up, slowly buying clothes, dressing furtively, shamefully, until things would get too serious with a girl, then - a fearful, hurried purge, a headlong plunge into the cold waters or normalcy. What a deceitful plunge it...

Home in the Hills Pt. 01

by ValoryG on Dec 10, 2019
Transgender & Crossdressers

All names and characters in this story are fictional and have no connection with any actual person living or dead. ***** Jonathon Worley is in his sophomore year at Onanoma State University, majoring - at least for the time being - in art history. He's the third child in his family, and after his parents paid for the first two to go to college, there was...

Jolene's Momma Pt. 01

by ValoryG on Jul 27, 2020
Transgender & Crossdressers

(The names and locations in this story are completely fictional and have no connection with any person living or dead.) My name's Chris. Wife Jolene and I have been married six years now. Live in the small city of Centertown, Ohio. It probably got that name because it's about half way between Columbus and Cincinnati. Being from a midwestern small town, the...