Crossdressing Stories

1,097 results
Orientation
Length
Source
Infinite Scroll

Sissy Meets Daddy

by lapitup_ on Jul 2, 2018
Transsexuals & Crossdressers

I never noticed in the moment, but I had been a sissy my whole life. Growing up I was always the shortest boy, always the weakest, I never had a girlfriend, and I wasn't good at any sports. My mom always told me I would grow into a man eventually, but that never happened, even during puberty my growth was minimal. By the time I finished high school I was a...

Lessons with Kelli Ch. 01

by Lifeatlarge on Sep 19, 2017
Transsexuals & Crossdressers

Writer note: This is the first of three chapters to this story and it really happened. Sometimes you are the teacher and sometimes you are the student, but that is what makes life worth living. Running a small junk and antiques store in a small town isn't the best way to get rich but I get by. I'm in my fifties, been living on my own for a while, and a...

Kasey's Confession Ch. 14

by KaseyLegs on Sep 14, 2017
Transsexuals & Crossdressers

Lying in the hospital bed, hooked up to monitors and who knows what else, I just stared out in shock. It was to be expected, they said, as they explained I had been in a coma for a very long time. What they did not know was that the source of my confusion ran much deeper than just waking up disoriented after a long time "away." I had absolutely no idea who...

A Cuckold Earns His Horns Pt. 01

by lapraline70 on Sep 16, 2017
Loving Wives

Dozens of replies. Dozens. I did it on a whim without Her permission; I was horny and thought it would be fun, never expecting anything to come of it, really. I've never been good at fortune telling, though, as the results attested. Hotwife/Cuckold-to-be seeks Bull to seal deal - mw4m my Wife is a pro Domme and has instructed me to place this ad for U/us....

Becoming Jessica Pt. 04

by Lovely_Jessica on Sep 25, 2017
Transsexuals & Crossdressers

Quick synopsis: My understanding wife, Emma, is helping me start to live part time as Jessica. After going to the gym we venture out to the mall for shopping and fun times. We got home and marched upstairs to clean up and change. Emma suggested I start putting my 'Jessica' things in one of the guest bedrooms and use the guest bathroom to shower. "I need...

Josie Loves Todd

by switchboi33 on Jul 3, 2019
Transgender & Crossdressers

As I lie here writing this story I am first and foremost aware of my great fortune. I am secure financially and personally. I have the career I always wanted, I have wonderful friends and an ironclad support system. The joy that I feel on a daily basis is made manifest each day as I wake next to my husband, the man who helped me to become the person that I a...

Cora Ch. 02

by Cora93 on Aug 26, 2019
Transgender & Crossdressers

Hey guys, enjoy the next instalment! I got some great feed back for the first story, if you haven't read it I'd recommend going back and doing so to better understand this chapter. I'd absolutely love to hear from you so please, submit a comment or hit me up for a chat x ***** I wake up to my alarm and sit up bolt right immediately. Getting out of bed is...

Maid to Order

by dreadknots on Jul 30, 2019
Transgender & Crossdressers

Hi! Another story! Yay! This one is a little softer, in the same vein as The Girl Inside. If you're looking for hard fuckin', this might not be for you. Definitely for folks who focus more on the crossdressing aspect and bois kissing bois. This is told in the 2nd Person too, and assumes you are a boy at the start. Just a heads up! Anyways, please enjoy a bri...

Julia, Ben and Lisa Ch. 08

by chloejacobs83 on Mar 2, 2020
Transgender & Crossdressers

Ch 08: Tuesday A few quick notes: 1. this is the eighth chapter of a longish story, a novel in many chapters 2. everyone is 18+ 3. there is no safe sex here - cause it's a fantasy, not an instruction manual 4. crossdressing and gender bending, not everyone's cuppa tea - be forewarned I'm sorry for sounding so stupid back there. For sounding like I'd never...

Life and Time of Lady Vargos Ch. 17

by rik581 on May 21, 2019
Transgender & Crossdressers

"Martin's Marital Indiscretion" Martin walked down the street with Darren toward the motel where he and Darren would have sex together in order to start rumors and hopefully a scandal that would being to an end his days of living as a woman and wife to the Baron. Martin felt very uncomfortable as they walked holding hands. People stared at them as they pas...