Gay Crossdresser Stories

23,018 results
Orientation
Length
Source
Infinite Scroll

Lucian Ch. 05

by angiquesophie on Sep 11, 2017
Transsexuals & Crossdressers

Spring arrived at Norton's Academy of Excellence. It painted the drab lawns with blazing green, causing desolate bushes to burst into a zillion flowers. Chaotic birdsong filled the sky, and Lucian Gaines ran, seeing it all happen - the yellow of daffodils, the purple of crocuses and the pure white of snowbells. Not that he had the faintest idea what th...

Magic Dress - Polly

by SlightlyRude on Dec 3, 2019
Transgender & Crossdressers

CHAPTER 1 I was mad to have bought it. It almost certainly wouldn't fit. I had just been passing the shop on my way home from work when I saw it. A green dress. Half price as the shop was closing down. They can't compete with the big stores selling cheap stuff, I guess. I had never bought a dress before, though I had often wanted to. I had been dressing up...

Sissification 101: Ch. 01

by silkstockingslover on May 4, 2020
Fetish

Summary: Straight guy is caught watching sissy porn and...Note 1: Thanks to Eric who requested and helped plot this lengthy story. Note 2: Thanks to Tex Beethoven and Robert for editing. Note 3: All characters are at least 18 years old. Sissification 101: Ch. 01 1. MY SISSY CURIOSITY I've always liked nylons. I grew up when they were still popular and...

Life as a Bull Pt. 05

by Kalimaxos on Nov 4, 2019
Loving Wives

***** Copyright © 2020 - This is an original work by Kalimaxos and is protected under copyright by U.S. copyright law. It is only submitted at Literotica.Com and any submission to any other site has not been authorized by the Author. This is revised Part 05 of this story. In the original version, I came up with a happy ending to end the series. It has neve...

If you truly love me Ch. 03: Holly

by CreativityTakesCourage on May 11, 2020
Loving Wives

This is the third and final chapter in David, Holly, and Sophie's story. I hope their respective journeys has proved interesting, or at the very least, a distraction during the shutdown brought about by the Wuhan Virus pandemic. I sincerely hope you all stay safe and well. Look after each other. Sorry to repeat myself, but I give my usual warning about h...

Compromised Pt. 03

by HorribleHenry on Oct 5, 2020
Transgender & Crossdressers

COMPROMISED PART THREE CHAPTER EIGHT Park Green Private Hospital specialised, and probably still does, in mending wealthy people, particularly those with kinks. There was nothing that people did to themselves, or each other, that fazed the dedicated staff of the hospital. A patient with a torn arsehole caused by anal sex was very low down on their list of...

Rock and Roll Angel Pt. 05

by lostindavoid on Sep 16, 2017
Sci-Fi & Fantasy

Katrina House rock and roll pop star. One and a half years ago. Katrina House... Kat to everyone who knew and loved her, drove the fellowship van to the top of Devil's Wing Hill, renamed Joshua Hill by Ballinger University founders twenty years ago. Ballinger University was the number one Evangelical university in the country so it was understandable why it...

Dirty Business Trip

by Travel_by_day on Sep 25, 2017
Transsexuals & Crossdressers

Chapter 1: The Transsexual Hotel Encounter "Yes, I am checking in," I said, putting my credit card on the desk. The woman behind the desk took the card and looked at the name. She was about 5 feet 10 inches tall with dark black hair and brown eyes. Her skin was beautifully tanned and her lips were painted a reddish-brown colour. As she looked at the card I...

Quarter Ton

by JimBob44 on Jul 4, 2018
Group Sex

*Author's Note: Any and all persons engaged in any sexual activity are at least eighteen years of age. *Disclaimers: This story has been edited by myself, using Microsoft Spell-check. You have been forewarned. *.*.* Benito's Italian Dining had a head chef that truly knew the dishes, knew the secrets to making the perfect sauce, the marriage of olive oil a...

Caught in Her Panties Ch. 02

by Knightofround on Sep 16, 2017
Transsexuals & Crossdressers

This is a fictional story as was part one. The content of this story may not appeal to everyone. It includes female domination, crossdressing, strapon, lesbian, gay, and such. Just keep in mind that it is fictional and should not be taken seriously. Otherwise just enjoy the read. ***** It has been almost a month since my wife Mary discovered my secret. She...