Gay Pantyhose Crossdress Stories

103 results
Orientation
Length
Source
Infinite Scroll

What Do You Want Me to Do?

by Cyanlot on Oct 15, 2017
Gay Male

Dear Ted, I hope you're having a nice weekend with Wendy. No ... I don't, really. I just said that to sound nice. But I'm not feeling nice. So why should I try. Honestly, I don't know what more you want from me. If you wanted to end the whole thing because you thought it was wrong or because it threatened your sense of masculinity, at least I'd understan...

My First Sexual Encounter

by thebikinilover on Jan 13, 2018
Gay Male

My first time giving and receiving head goes way back to the 80's when I was nineteen, my best friend Mark whom I'd known since four years of age was my first sexual encounter. Although I had been stroking my cock for years I'd never been jerked off by anyone else, I was shy around girls and spent most of my spare time playing football. I'd just turned 19...

Glory Hole Revisited

by JRob on Sep 14, 2017
Gay Male

At the time I couldn't help thinking that everyone who saw me after my impromptu visit to the adult bookstore KNEW. They knew what naughty things I had done on my business trip to Philadelphia. They could tell, simply from my demeanor, that I had visited the dark, dingy booths in the rear and their x-rated peep shows. That I had played with myself while wa...

Catching Up with an Old Friend Ch. 01

by jjdtx on Sep 19, 2017
Gay Male

This story pics up some 20 years later from my college and camping series. Scott and I lost contact after our college days, both moving in different directions and taking different jobs that led us to various parts of the country. Both married, both had kids, and just went on with life. Thanks to social media, we actually stumbled across each other online....

The Shower

by James_444 on Aug 18, 2017
Gay Male

"You're sopping wet!" Harry exclaimed when he opened the door. "No kidding," James retorted dryly. "I was a halfway to my car when the sky opened up and dumped buckets on me. I figured that I could dry out here while I visited." "Sure, no problem," Harry said. He watched as James slipped his shoes off. A plan began to take shape in his mind and he smil...

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...

Ben Loves a Challenge Ch. 08

by PDreadful on Dec 9, 2019
Gay Male

**I promise this isn't the end, there's more Dean and Ben to come. I hope you enjoy. -Penny** What he'd felt after Laura left him felt shallow in comparison to the pain-coated emptiness inside him now. Nothing mattered anymore, Dean's cold dismissal broke something in him. Worst part was that he couldn't figure out where he'd gone wrong. Dean didn't call,...

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...