Gay Crossdressing Bondage Stories

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My Name is Dave Ch. 01

by davas on Sep 16, 2017
Gay Male

Hi. I'm Dave and this is my story. Let me tell you a little about myself. I am six foot even, 155 pounds with shortish blonde hair, and blue eyes. I am thin, but with strong legs and ass. I have light body hair, a fair complexion, but I can hold a tan. I think I've got a nice body; I'd fuck me if I had the chance. I am twenty-four years old, two years out o...

Remember Yahoo Chat? I Sure Do

by FinallyOpeningUp on May 22, 2019
Gay Male

The news was unexpected. I can't say it was devastating. In fact, it elicited no truly emotional response from me whatsoever. But just a few months ago I was scrolling through my Twitter feed and a headline jumped out: "Yahoo Chat to shut down permanently." I paused for a moment when I read that headline. Yahoo Chat. It had been probably ten years since I,...

Waking up gay

by Honeybunni on Sep 16, 2019
Gay

You stretch and open your eyes. Sun is shining, birds are singing. What a wonderful sleep! Ever since your girlfriend left you, the bed has always felt empty, but that was phenomenal! Finally moving on from that bitch and ready to move on. You brush off your covers, letting the air hit your naked body. Sleeping naked is healthier for you; or so that one Face...

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BBC Cheerleader

by Alysonthecorruptedslut on Feb 10, 2020
Gay

// Hello, I'm glad you've taken an interest in my musings, I'll be updating this story as much as I can, but please be patient as I do have a busy personal life on the side. If there's any particular fetishes you'd like to see in her, send me a message and I'll see what sort of magic I can make. ~Alyson \\ You thought long and hard about how you were going t...

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Transported to Homo-World

by jmce on Sep 26, 2017
Gay

My name is Dick and this is the story of when I ended up in Homo-World, the adventures I had there and how it ended. It started a normal enough day, I woke up, took a shower, brush teeth etc. It was Sunday and I had nothing planned when Love called and asked "Hey, you have anything planned?" "Honey, it's Sunday. The only thing anyone ever plan...

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My Gay Crossdressing Vacation Ch. 06

by Flame666 on Jun 9, 2020
Gay Male

I woke up looked at the clock, it was 10 am the sun was out and hot, it was a beautiful day. I rolled out of bed realizing that I had cum all over me, in my hair, in my mouth and leaking out of my boi pussy. I peeled off my 40 D breast forms and headed to the shower. While in the shower, I thought about my plans for the day and the coming night. I remember...

A Real Bathhouse Slut is Made

by Danmo1 on Sep 16, 2017
Gay Male

This true account of the activities of a mature 50'ish guy continues from my first time at a bathhouse entitled The Making of a Real Bathhouse Slut. As I drove home from the bathhouse the first week I had a hundred different things going through my head, one of which was guilt. I quickly realized that after years of no sex with my wife there was really noth...

Pussyboy Nephew Ch. 01

by bufmuck1 on Sep 16, 2017
Gay Male

So I went to stay at my aunt and uncles. I had finished another year at university, and my mom said I should spend a few weeks with them, if I had nothing better to do. At first I wasn't that interested, what with my aunt living in a quite area and they were both in their forties, I liked the city where we lived, and enjoyed being around my mates. However I...

Sissies love big black cock

by Yelawolf on Nov 16, 2017
Gay

Welcome to the story you crazy sissies and you strong aphla black males. This is from edithis and I want to bring here so you guys can write or read or for the real reason you're here to masturbate. Get your hand, dildos, lube, and whatever else you need to jerk it off. Time to begin the story up. (Thanks for all of the likes and support on this story. I jus...

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The Boifriend Ch. 01

by AdmiralSquish on Aug 8, 2018
Gay Male

[pre-story]Content Warning: SUPER gay. Crossdressing. Sissy self-deprecation. There's going to be some unrealistic anatomy later on, huge cock, huge balls, and huge loads. Disclaimer: All characters are 18+[/pre-story] ***** The Boifriend, Chapter 1 "Whelp!" Leo exclaimed as he stood up and gave an exaggerated stretch, feigning a yawn. "Looks like it's t...