Gay Pantyhose Crossdress Stories

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Discovered by a Black Guy

by chastity_sissy on Sep 14, 2017
Gay Male

I should preface this story by saying I've never identified myself as homosexual, but sometimes after being locked up in chastity for a long time combined with crossdressing, I must admit to some fantasies involving other men. I never expected anything to ever actually happen, and it's my own fault really. I had been paying a beautiful, very sexually fetis...

My CD Slut

by eljayb on Jan 23, 2019
Gay Male

Sweet encounters As a sexually active 77 year old I have recently been attracted to the lovely world of Crossdressers. Not that I wish to dress myself but I enjoy the company of those who do. In my travels I found this interesting personality called Chrissie. Age 64, CD/TV/TS. After we exchanged messages and emails for a while, I felt we might get on well...

Daddy's New "Wife"

by Shadow Shark on Dec 4, 2019
Gay

Hello! My name is Tristan Wood, or Triss as my friends and family like to call me. I'm 22 years year old, recent college graduate, and unemployed. Right now I'm living with my old man Harry Wood, he's a thickset man in his late 40s. Though, pops has been living in constant sadness since mom passed away seven years ago. At first, he barely bothered to do anyt...

Cocksucker: Cum Slut

by silkstockingslover on Sep 14, 2017
Gay Male

You do not need to read the first four chapters of this story to enjoy this story of a straight man that gets submerged into the drag queen world of San Francisco (but obviously it helps). In case you are curious how this straight married man got into this predicament here is a brief summary of the first four chapters of "Cocksucker": Chapter 1: Cocksucker...

Catching Up with an Old Friend Ch. 01

by jjdtx on Sep 19, 2017
Gay Male

This story pics up some 20 years later from my college and camping series. Scott and I lost contact after our college days, both moving in different directions and taking different jobs that led us to various parts of the country. Both married, both had kids, and just went on with life. Thanks to social media, we actually stumbled across each other online....

My Dream Solution Ch. 01

by Cyanlot on Sep 15, 2017
Gay Male

[Note: This is a long introductory setup to a multi-part story. There is *no* explicit sex in this first chapter. If you are looking for quick, hot read, move on. This is not it. Things will heat up in later chapters, I promise. --Cyanlot] Chapter 1: When I Hit the "Change of Life" When Massachusetts became the first state to legalize gay marriage, Todd a...

Bob Handles Mark's Huge Tool Ch. 01

by scrotus on Aug 18, 2017
Gay Male

I had long fantasized about being involved in a sex situation with more than one guy. I had done several three ways with a woman (two guys and one girl) but they never involved the other guy and I performing on each other. In recent years, I've developed an insane desire to move beyond my several male-male encounters and add a third guy in. This is because o...

An Old Friend Ch. 03

by jjdtx on Sep 19, 2017
Gay Male

Chapter 03: The last time together Once back from dinner, I had Joe strip and bend over the back of his couch. I carefully removed the large butt plug from his ass, his hole remained gaping open. I quickly dropped my shorts, coated my cock in baby oil and slide it into his wide open ass. His anal walls adjusted to my cock and he groaned as I slide deeply in...

The Bartender Ch. 02

by Pan2 on Jun 8, 2020
Gay Male

As soon as Roger walked through the saloon-style doors, Kent reached for a glass. He'd never before seen a man in such need of a drink. If the dark rings under his brown eyes weren't enough, his incorrectly buttoned-up shirt and mop of dishevelled brown hair clearly used to more attention than it was currently getting were a clear indication that Roger was...

Pantyhose Seduction

by nylondad on Sep 17, 2017
Gay Male

I was single and aged 26. I had been engaged for two years to a beautiful woman but the relationship had gone stale for each of us. We had lived together in a garden apartment for two years and she chose to move out and was staying with her parents until she could find a new place. I was sad as I missed her but felt relieved with the knowledge that the word...