Gay Pantyhose Crossdress Stories

103 results
Orientation
Length
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Infinite Scroll

Married and Gay Ch. 02

by paulsenc on Aug 18, 2017
Gay Male

As the days followed after my initial encounter with Larry, my desire to be with him again grew stronger and stronger. I felt this inner need to express a kinky side of myself that I hoped he would like. I often enjoyed wearing pantyhose as a way of getting off during my many jack-off sessions. I called him several times after our first time to see if we co...

Sharing Secrets Pt. 04

by Showoff888 on Sep 14, 2017
Gay Male

NOTE: This story entails piss play. ***** Hoshi slowly returns to consciousness and awareness as the wisps of sexual bliss begin to fade. He can feel the warmth of his naked body lying under the warmth of his friend's naked body. He can feel the mass of cooling river of cum that was deposit between his ass cheeks and is making its way down his ass onto t...

Lonely Cock Sucker

by silkstockingslover on Dec 9, 2019
Gay Male

Summary: Lonely married cock sucker discovers young cock close to home. Note: Thanks to Tex Beethoven for editing this story. Note 2: This is a holiday 2019 Contest Story. Lonely Cock Sucker I love cock. I love everything about it. The variety of shapes. The upward curve that often makes me gag even on a smaller cock. The downward curve that slides int...

Nylon Suck Again Ch. 02

by nylondad on Sep 16, 2017
Gay Male

I slept in one of the single beds that night. After Jimmy and Nils had flooded me with their come I had a beer and went to sleep. It was apparent that both guys wanted a second round but for some reason I was not up for it. My stomach was a little upset after it was flooded with the two massive loads I had swallowed. Before dozing off I could hear them speak...

The Misadventures of Nylogirl

by NylogirlCD on Aug 22, 2019
Gay

Megalopolis is a crime riddled city in dire need of a hero, or in my case, heroine. My name is Julie Hosaree, but my alter ego is Nylogirl. From what I can recall from my broken memories, I'm the result of genetic experimentation, an attempt at a super solider. While I have the super strength and speed there are some... Side effects. My powers only work when...

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Exploring my Sexuality Ch. 02

by alexis19901 on Jun 2, 2020
Gay Male

Just a quick recap from the first chapter. I'd made my first trip to a sauna, lost my virginity, got spit-roasted and then another guy came in my ass all before I left. The last guy left me his number and I just couldn't resist. This story will contain some crossdressing. I'd gone back to my normal life for a number of weeks since my trip to the sauna. Havi...

Discovered by a Black Guy

by chastity_sissy on Sep 14, 2017
Gay Male

I should preface this story by saying I've never identified myself as homosexual, but sometimes after being locked up in chastity for a long time combined with crossdressing, I must admit to some fantasies involving other men. I never expected anything to ever actually happen, and it's my own fault really. I had been paying a beautiful, very sexually fetis...

His Sweet Boy Ch. 06

by Her11 on Sep 21, 2020
Gay Male

AU: I'm Back! I know i was a little slow to write but im working on it. P.S. to Crven_ban: do not read my mind it freaks me out. To everyone else, 40th comment on His Sweet Boy Ch.04 ********* Ben slammed the office door, then spotted the bathroom and shuffled awkwardly into it slamming that door for good measure. Fucking hell. Eric was going to be the...

BBC: Like Son, Like Father

by silkstockingslover on Jul 9, 2019
Gay Male

Editor's note: this story contains scenes of incest or incest content. Summary: Father catches son sucking BBC & gets very curious. Note 1: This is a NUDE DAY 2019 story so please vote. Note 2: All participants are at least 18-years-old. Note 3: Thanks to Tex Beethoven and Robert for editing this story I'd just gotten home from work and was in the k...

Cocksucker: Cum Slut

by silkstockingslover on Sep 14, 2017
Gay Male

You do not need to read the first four chapters of this story to enjoy this story of a straight man that gets submerged into the drag queen world of San Francisco (but obviously it helps). In case you are curious how this straight married man got into this predicament here is a brief summary of the first four chapters of "Cocksucker": Chapter 1: Cocksucker...