Gay Pantyhose Crossdressing 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...

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...

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...

Five in One Night

by jordan80 on Aug 18, 2017
Gay Male

When I walk into the bar there are only a handful of people inside. The bartender gives me a grin and a nod; guess that happens when you're a regular. The waitress comes over to take my order and I admire her uniform. This place is attached to a very nice hotel, so the waitress's uniform is a cross between professional and slutty. For some reason, that turns...

Sharing Secrets Pt. 05

by Showoff888 on Sep 14, 2017
Gay Male

I'm a shy, smallish, slightly pudgy from my waist down, a bit wider in the hips, butt and rounder legs, small delicate hands and feet. I think I'm a very passable nubile little Japanese girl, with shoulder length black hair, small nose, full lips, long lashes, and a tiny penis, and obviously flat chested. This summer, my Mom divorced my kinky Dad, for someon...

An Old Friend Ch. 02

by jjdtx on Sep 14, 2017
Gay Male

Chapter 2 – The Next Day The next morning, Joe left early for work and I didn't have an appointment until late in the day. So, I lounged around, looking at his DVD collection. In a small box, I found his porn stash. It was a nice selection of compilation DVD's. About twenty in all, most were straight cum shot movies, but there were four bi movies. All were...

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...

A Natural 'Gurl'

by sexyR2 on Aug 18, 2017
Gay Male

Yes, I know that it has been a few years since I last posted. I was busy. I hope, however, that this new story makes up for the delay. It is in a new category for me, gay male instead of gay female like two of my previous submissions. Enjoy! Debbie, er, sexyR2... ***** Today... When the somewhat urgent knocking came to the door, Debbie knew in an inst...

From Straight To Slightly Bent h. 02

by Akito01 on Aug 18, 2017
Gay Male

My decision to continue the affair is not a clear cut one. In the past, I never would have considered myself the sort of person who would cheat on their mate. On the other hand, I continued to play out the events of our first night together in my head, and all the things that I could still yet do to you... In the end, I knew I had to have you again. The f...