Gay Pantyhose Crossdress Stories

103 results
Orientation
Length
Source
Infinite Scroll

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...

Stoner with a Boner

by Tahoestud on Aug 18, 2017
Gay Male

Three days ago, my wife passed away after being hit by a car while jogging. She always enjoyed running to keep in shape. I was in a daze all during the funeral not quite coming to grips with fact that she was actually gone. In the hours following the funeral, I returned home with my two young daughters, who along with their friends, stayed in the living room...

My First Time Ch. 01

by doctrtic on Aug 18, 2017
Gay Male

He was my first, he was in his 40's I was 20. I worked for him and he invited me over for dinner and drinks. I really was not aware of his interest in me. Michael was just a nice guy. I was kind of a pussy hound at the office,if the ladies were in business attire(pantyhose and heels). I would make a bee line to talk to them. Michael finally approached me...

The Book and Video

by TerriC on Sep 14, 2017
Gay Male

By the time I was 18 I had been dressing in my mom's lingerie for a few years. I had always liked to sneak into her room when she was out and try on her panties, bras, and other assorted lingerie. Her pantyhose were always my favorite though, they felt amazing on my slight, nearly hairless legs. As my passion for wearing pantyhose grew, I took to keeping a...

Third Shift

by TerriC on Aug 18, 2017
Gay Male

"I slapped her tits with my cock, rubbed my balls on her nose, and sprayed all over her face." That's the reason no one liked working with Leo. Not that he was a bad guy, he just had no filter when it came to speaking. Lines like that, to Leo, were as normal as "Good morning," or "Extra sugar with my coffee please." The early fall was the busiest time of...