Gay Pantyhose Crossdresser Stories

136 results
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Infinite Scroll

Fucked

by TerriC on Aug 18, 2017
Gay Male

It hurt. It hurt a LOT!! Every thrust was painful, even with plenty of lube. There was no numbing, no getting used to the feel. It was just painful. Yet, I let him keep going, it had to feel good at some point. An hour ago I was buzzed chatting online, horny as always when I drank. I loved drinking and chatting online, it was harmless fun, playing a role wh...

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...

First Time Bound

by juliegomez on Aug 18, 2017
Gay Male

This was my first time. Yes I had given a few blow jobs. Yes, I had been taken from behind just once or twice. Or once or twice more. But I had never found anybody before that wanted to tie me up and use me for bondage sex. I stood quietly without moving. My feet were about a shoulders width apart. I was taking short shallow little gasps of air as I waited...

Uncle Jon's Cock Ch. 03

by nylondad on Sep 16, 2017
Gay Male

When I arrived home I took a hot shower. Being with Uncle Jon all day was so much enjoyable for a variety of reasons. One was that I had a much needed and much deserved day off from work. Another and most important was that perhaps I was going to have a suck buddy to play with on occasion. Uncle Jon had been so insistent about getting together "soon" that my...

An Old Friend Ch. 03

by jjdtx on Sep 19, 2017
Gay Male

Chapter 03: The last time together Once back from dinner, I had Joe strip and bend over the back of his couch. I carefully removed the large butt plug from his ass, his hole remained gaping open. I quickly dropped my shorts, coated my cock in baby oil and slide it into his wide open ass. His anal walls adjusted to my cock and he groaned as I slide deeply in...

Silk House Pt. 02

by jaiunus on Mar 12, 2019
Gay Male

Even though Toby and I were fully confident Mr. Doherty was deviously playing matchmaker with us, it didn't stop our play from turning to actual panic when, across the house, we heard the familiar sound of keys rattling. Conveniently, after a few hours of rollicking about I was still somehow free of wearing spandex gear—Toby liked to hold it against me after...

New Neighbors Ch. 02

by idsweaterguy on Sep 16, 2017
Gay Male

After Jeffrey's breathing returned to normal and his cock began to soften, he laughed and told me to continue to keep his cock in my mouth. "After all," he continued, "you are still tied up and rather at my mercy wouldn't you say?" I managed a "mmmppphh!" and nodded. I, too, was enjoying the moment. We remained like that for a few minutes—me tied hand an...

Outrageous Cum Sucker

by Alluring_Crimson_Shifter on Aug 31, 2017
Gay Male

Ricky was on the way back from the Adult store. His cock was already heavy from the conversation with the clerk, and he was anticipating watching the adult movie DVD. For a moment he hesitated, then called his best friend Greg. "Hey Greg, what are you doing right now, I just got another movie. It is supposed to be good. Why don't you stop by so we can watch...

The Bartender Ch. 02

by Pan2 on Jun 8, 2020
Gay Male

As soon as Roger walked through the saloon-style doors, Kent reached for a glass. He'd never before seen a man in such need of a drink. If the dark rings under his brown eyes weren't enough, his incorrectly buttoned-up shirt and mop of dishevelled brown hair clearly used to more attention than it was currently getting were a clear indication that Roger was...

He Knew It Was Wrong Pt. 02

by LoveIsUniversal on Sep 14, 2020
Gay Male

The text message was short and to the point. Bridget wanted him to be with her tonight. It sounded like a fun time, but Zack already had other plans. His text message was also short and concise. He wrote that he had other plans for tonight. He issued an apology in the same text message, though he reassured Bridget that the two of them would get together agai...