Crossdressing Stories

1,097 results
Orientation
Length
Source
Infinite Scroll

Return Of The Horny Femboy

by chlomo on Oct 6, 2020
Erotic Horror

This is the sequel to Night Of The Horny Femboy, it follows characters and events from that story, so feel free to read that first if you haven't :) This is an erotic horror story with mind control, reluctant sex and crossdressing. It's not meant to represent or anything seriously, it's just for fun. I'm Markie, well, I'm Markie now. 3 weeks ago I was targe...

This to Keep Me Quiet Ch. 02

by MicheleNylons on Oct 5, 2020
Transgender & Crossdressers

Chapter Two - I Am Yours With The Following Caveats When Michael finally escaped the investment meeting he scurried back to his workstation. Stills and Shipley had installed the latest technological advances in their offices and each of the staff had their own computer which was linked to the office network and some were linked to other financial institutio...

Brotherly Love, Sisterly Love Ch. 02

by sexy_jessie on Sep 25, 2017
Transsexuals & Crossdressers

CHAPTER TWO - THE COSTUME PARTY "RACHEL" My twin sister, and sometime brother, and I had been experimenting sexually with each other and crossdressing together for around a month, growing to love and to perfect our new feminine personas until they became the ones we thought of as our true selves. Whenever our parents were away from the house, we would snea...

Team Spirit

by ThighhighMellie on Sep 19, 2017
Transsexuals & Crossdressers

Team Spirit All characters in this story are 18 or older. Act I: Rain Delay High school was a hard place for a closet transsexual from a traditional family. Day in and day out, having to pretend to be someone you're not. But at the very least, after I met my friend Jessie, a few things turned around for the better. I had a very small figure that I tried...

Cocksucker: Cum Bucket

by silkstockingslover on Sep 25, 2017
Transsexuals & Crossdressers

Summary: Shemale and others gangbang straight crossdressing anal virgin. You do not need to read the first parts to enjoy this story of a straight man's hotel orgy of gay submission. In case you are curious how this straight married man got into this predicament, here is a brief summary of the first three chapters of "Cocksucker": Chris, a married straig...

Let the Spirit Lead Ch. 01

by purplepantiesgirl on Jun 10, 2019
Transgender & Crossdressers

Andrew had sunk somewhere below rock bottom he felt. Life had become miserable. Nothing in his existence was going well. Keeping with the adage of Americans hitting the open road in times of tumult, he followed suit and packed some of the belongings he still owned. During his recent divorce, he'd acquiesced and signed over much of his net worth to his now fo...

Casey's Submissive Journey Pt. 06

by corduroysissy on Feb 7, 2018
Transsexuals & Crossdressers

Homo Hubby Night – Part Two Note: In this continuing saga, Casey (Debbie) & Jamie (Angie) are closet crossdressers who are submissive to their wives Karen & Audrey (respectively), however in this section of the story there is no cross-dressing. Their wives are humiliating them by making the boys put on a homosexual sex show for their amusement. *...

Transgender in the Old West

by JonThomas_ on Mar 25, 2019
Transgender & Crossdressers

Greetings all; in my stories my characters exist in my head, but there might be real life inspirations for some of them. Who knows? Anyways as my regular readers are aware, I enjoy writing about characters with fluid sexuality. This is a story with transgender and crossdressing characters set in the old American west. ~~ John Calvin Kelly was JC's gover...

Rosie Finally Meets Jessica

by DoesAnyNameWorkOnHere on Aug 6, 2019
Transgender & Crossdressers

It was cold. Bitter cold. January always brought negative temperatures and more snow than I care to see. It's the kind of cold that gets into your bones and you can feel it for hours after being in a warm place. Not even a hot shower can soothe the chill you have inside. Short days and long nights made the month long and depressing. My only respite from the...

Rebound

by toniukcd on Sep 13, 2017
Transsexuals & Crossdressers

My story is nothing new, like most girls who used to be boys I knew from an early age that I was different to all my school friends. My dad was a thug of a man, who enjoyed the physical battle of the rugby pitch as much as the post match booze up, but I took after the mother who died giving birth to me. Oh tried to be the sort of little boy my dad wanted, bu...