Gay Pantyhose Crossdressing Stories

156 results
Orientation
Length
Source
Infinite Scroll

A Dandy Professor and a Dapper Boy

by ThomasStevenson on Jul 17, 2019
Gay Male

Something about the sheer dress socks made Charles nervous. He was at his bed, fully dressed in his best three-piece suit, lush paisley tie knotted around his crisp cutaway collar, grosgrain braces to match, silk handkerchief spilling out of his breast pocket, glittering cufflinks--the whole nine yards. But he saved the sheer socks for last. It was the way...

Silk House Pt. 01

by jaiunus on Mar 12, 2019
Gay Male

Author's Note: This story is all about spandex and focuses a lot on the "dressing up" portion of play, as it is the author's favorite. Just a heads up. Happy reading! ***** There were two things I was absolute certain about myself when it came to my personal sexual pleasure. One was that I had an incurable desire to wear, see, and feel spandex. That much...

Changing Teams

by shptchr on Mar 12, 2019
Gay Male

Editor's note: this story contains scenes of incest or incest content. ***** Dear Reader: This story is a response to a request. It's a stretch for me to try an unfamiliar genre. Since I am not gay and have very little experience interacting with the gay lifestyle, please excuse my naive view and know I wrote from the heart. Regards, shptchr. As always, th...

Turning Myself Gay Pt. 02

by bart_allen on May 29, 2018
Gay Male

It had been an exciting experience. I jerked off two more times once I got home that night, focusing more on the thought that I had taken such a large step in turning myself gay. I certainly didn't feel any different, I just did what gay guys do, suck cock. Of a random guy they solicited off Craigslist, chiding myself for the thought. But it was one of many...

Charlie

by Dennis_St_John on Aug 30, 2017
Gay Male

I froze in shock, not wanting to believe what I was seeing. This had to be some sort of sick stupid joke my best friend was playing on me. I pulled my eyes away from his chest and looked him in the eyes, seeing tears and shame on his face. Anger surged through me like a bolt of lightning, feeling betrayed and a little stupid. I couldn't help myself, I sa...

Exploring my Sexuality Ch. 03

by alexis19901 on Jul 6, 2020
Gay Male

I could have put this story in a number of categories but it consists a lot of gay sex so that's why I've picked it. It does contain some elements of taboo, group sex, crossdressing and gay sex. The other chapters do provide some of the back story. After my last meeting with Mark, I went back to my normal life. Going to work, college and seeing my girlfrie...

Frat Party Costume Sex

by SluttyBisexualGuy on Mar 2, 2020
Gay Male

This is the story of how 19 year old Caleb Jensen found himself in the sexual predicament of a lifetime. It was the fall rush season and Caleb had been accepted as a pledge at the USC frat of his choice: Tau Kappa Epsilon. Their off-campus reputation was legendary and they threw incredible parties that people talked about for weeks. The girls that attend...

The Lure of Cock from the Closet

by jakladd on Oct 15, 2017
Gay Male

It's true. We desire cock. Our wives have no idea what goes on inside of us with this desire to submit...to cock. We hide it from everyone but in our minds it's a runaway train. To touch, feel, pull on, sniff, rub our faces in it, lick it, taste it, suck cock. We've done it before, maybe a short time or a long time ago. The specter of guilt and shame dampens...

Mind of Straight Married Cocksucker

by silkstockingslover on Sep 14, 2017
Gay Male

Summary: The 10-part philosophy of a straight cocksucker. DISCLAIMER: This story is based on a couple years of research and conversations with straight men who are curious or are cocksuckers. Although I am female, I find a man sucking cock hot, I suppose like most men find two women hot. Thus, I thought I would, based on my many conversations with straight...

You are a Sissy Pt. 03: Body

by Roland15Rollin on Dec 24, 2019
Gay Male

Hello. Hello, sissy. You have come back. You have come back again for another session. Welcome back, faggot. My sexy sissy faggot bitch. I am so glad you have come back. But you have no choice, do you, sissy? You have to come back. You need to come back. You need to hear my voice. It is the voice of truth. The voice that tells you what you are. What you tr...