Gay Pantyhose Crossdresser Stories

136 results
Orientation
Length
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Infinite Scroll

Solitude Leads to Curiosity

by Creativekink on Aug 18, 2017
Gay Male

Iowa is just about the middle of nowhere. And I was just about stuck there. A few years ago, I was working for an issues group right outside of Omaha in Council Bluffs. To a lot of people, it would seem a great gig. I barely had any accountability, didn't have to report to someone except by phone or email, worked from my office, and set my own hours. There...

Tethered and Feathered Saga Ch. 01

by doctrtic on Oct 15, 2017
Gay Male

I was thirty-one years old and was addicted to pantyhose and nylons. Various girlfriends over the years have indulged my fetish, with pantyhose sex, nylon foot jobs, and some would let me smell and kiss their pantyhose covered feet. Something happened during this time that was mind blowing. I was over at my friend Nick's house. Nick is am openly bisexual ma...

Bathhouse Observations

by glory_first on May 12, 2020
Gay Male

The baths are undoubtedly the easiest place in a city to have male group sex, after allowing for individual circumstances during any single trip. After more than a hundred visits over the last few years, basically all of them involving satisfying sex with other men, often writing about the experiences afterwards, leads to a few general observations. Visitin...

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...

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...

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...