Gay Pantyhose Crossdressing Stories

156 results
Orientation
Length
Source
Infinite Scroll

My First Time Giving Oral

by MrJimJim on Sep 15, 2017
Gay Male

Through my tears I watched the neon of the bar get brighter. She had left me, for good this time... All my attention had been focused on other things, including porn, and everything but her. I'm not angry with her, but with myself. That's why a few tequila shots will make me forget... This was the alcoholic amnesia, the whole place filled with men who want...

Back to the Book and Video

by TerriC on Aug 17, 2017
Gay Male

The sound of the quarters hitting the floor shattered any sense of pride I'd had. The joy I felt with his dick in my mouth minutes earlier, gone, replaced with a deepening feeling of shame. There I was, on the floor, naked, except for the pantyhose. The drying spit and cum on my chin and chest, the wet spot on my hose, serving as sticky reminders of what had...

MMF First Time

by Erotic Celt on Aug 18, 2017
Gay Male

From the moment I arrived I knew I was in for a treat. A sexual experience that would last with me forever. Janet had always been a sexual dynamo, and she could never get enough sex and was always trying out new things. I had only been going out with Janet for six months, and I already felt incredibly relaxed with her. Sometimes, I found, it could take years...

It Was So Exciting

by sindyxdresser on Aug 18, 2017
Gay Male

It was about 230 am Friday night when I walked into the Crypt adult book store on 30th Street in San Diego Calif. The Crypt's usual clientele was mostly gay men, and tonight was no exception. I felt my face burning as I walked back into the peek booth part of the store. These booths had no doors or curtains so offered no privacy of any sort. There were sever...

The Reluctant Bear Hunter

by newpaulman on Jul 3, 2019
Gay Male

First I must apologise to any gay men reading this who like their stories with a romantic element. That is not what I am looking for with a man. I am a part-time bisexual. I can go months without thinking about gay sex, but then the urge comes back. The urge to be fucked, that is. The urge to suck a cock and see spunk fly from it. The urge to get naked with...

Rape Fantasy

by MrJimJim on Oct 3, 2018
Gay Male

Editor's note: this story contains scenes of non-consensual or reluctant sex. * Rape fantasy First off, let me just say this is a 100% true story. It has taken me almost 2 hours to write down because I keep stopping to jerk off when I remember the sexy parts of what happened to me. So I've had a rape fantasy for many years, but never found anyone willing...

Nylon Suck Again

by nylondad on Sep 16, 2017
Gay Male

My cousin Jimmy and I burned up the telephone lines after our first meeting. In that meeting I had "borrowed" a pair of my sister's stockings and gave them to my cousin as a gift. He and I had a thing about women in stockings and he would focus on my sister. I tried the stockings on at his home one weekend and I ended up sucking him off twice that weekend. T...

The Shoe Store

by PhRedSonya on Apr 17, 2019
Gay Male

I have always enjoyed the feel of pantyhose on my legs, ever since I was a little boy. My name is John and I love to wear women's clothes underneath my work clothes. I am 5'8", have a slender build and keep my legs shaved all the time. When my friends ask why, I explain that it helps when I swim. Today, after work I had decided to go and check out the new sh...

Crossdresser's Unexpected First Time

by kprice1984 on Nov 27, 2017
Gay Male

Just want to say firstly, that this story is 100% true. Secondly, it was much better in person. I'm just getting around to writing it after several years. ***** I'm a 20 year old guy, very good looking, easy to get girls. Brown hair, green eyes and a sexual appetite that's hardly ever satisfied. I had always had a craving or tendencies towards being a lit...

At the ABS Again

by TerriC on Sep 21, 2020
Gay Male

I was 18 when I sucked my first cock. A trip to the local adult bookstore had ended with me blowing the owner. This was already told in a previous story, The Book and Video, if you're interested. After a rather shameful departure on my first visit I did manage to make it back for another round, with much better results. After those first few visits, I real...