Transsexuelle & Crossdresser Stories

809 results
Orientation
Length
Source
Infinite Scroll

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. *...

Dolled Up To Rock 'n' Roll

by shawnavinyltv on Oct 12, 2017
Transsexuals & Crossdressers

I've always been a rocker, not that I don't love other types of music, too, but there was always something about going to a rock concert that had a special air. A kind of vibe that was hard to describe. Almost like an energy in the crowd connecting them to the band. Of course, I'd been to a number of shows over the years, saw some big bands, some unknowns an...

Meara and Oakley Ch. 05

by Erisjade16 on Feb 11, 2019
Interracial Love

It's 10 o'clock in the morning and I'm up making breakfast. Two years into our marriage, I stopped cooking for Xavier. Which was a pretty big deal, considering I come from the type of family where food equals love. Or, at the very least, affection. Xavier never even noticed. But, this morning, in spite of the previous long day and night, I'm up and at '...

The Robertson's Sissy Ch. 03

by Clite69 on Jul 31, 2019
Transgender & Crossdressers

**A quick note. The chapters of this story can fall into mutiple categories, group sex, reluctance/nonconsent and transgender/crossdresser. If any of these are not your taste than this story may not be for you.** ***** Beep...Beep...Beep... Is all I heard as I woke the next morning. I smashed my alarm clock off and laid there completely hung over from all...

The Robertson's Sissy Ch. 08

by Clite69 on Sep 9, 2019
Transgender & Crossdressers

**A quick note. The chapters of this story can fall into mutiple categories, group sex, reluctance/nonconsent and transgender/crossdresser. If any of these are not your taste than this story may not be for you.** * I woke the next morning without a care in the world. This was the first morning since all this started that I didn’t wake up in a panic. I laid...

Matt Becomes Mattie Ch. 10

by clarepanties on Sep 19, 2017
Transsexuals & Crossdressers

Morning came and Louise and I again made love before showering, dressing, breakfasting, and then going our separate ways for the day. I did a number of jobs before sitting down and writing an e-mail of the summary of the evening for Jo's reading and pleasure. Life returned to 'normal' with the return of the children and they were full of what they got up to...

In from the Rain

by dreadknots on Apr 17, 2018
Transsexuals & Crossdressers

Elevator Pitch: Opening the door to a cute looking girl, Mike discovers that she's not exactly what she appears. Lewdness and maybe good feelings ensues. *** Mike didn't even need to open his door to know that something was wrong. First of all, someone was knocking just before Midnight. Whoever it was on the other side was on his property, a lonely little...

Life and Time of Lady Vargos Ch. 02

by rik581 on Oct 9, 2018
Transgender & Crossdressers Stories

To the new reader. The Life and Times of Lady Vargos is the second book in the Martin Hastings Saga. The first book, The Marriage of Martin Hastings is posted here on Literotica. ***** Chapter 2 "Family Portraits" Martin had now been married for just over two weeks. He and his husband, the Baron, had consummated their marriage together with the tradition...

Karlie's College Adventures

by enobeson on Dec 10, 2017
Transsexuals & Crossdressers

I don't suppose my story is really any different when it comes to cross-dressing. It began when I was young and continued to flourish as I grew older. I lived alone with my mother growing up. My father had been killed in car wreck when I was 8. He had been a successful stockbroker and had left my mother and I financially stable, if not wealthy. My mother was...

Casey's Submissive Journey Pt. 02

by corduroysissy on Dec 14, 2017
BDSM

Debbie's eyes bulged when he looked up at Angelina, and his best friend smiled back at him. "This is my Angie, Debbie, he wanted to watch you cream his jeans." Looking through the make-up and wig he could barely make out the face of his young buddy. Casey was blown away by how good Jamie looked as a girl, he was pretty as all hell. The make-up looked perf...