Gay Sissy Interracial Stories

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Full Sissy

by Nils Huim on Dec 24, 2017
Gay Male

Darren couldn't believe his luck. Couldn't believe this was his wife Joy's birthday present to him. It was by far the best—the most exotic and erotic anyway—he'd ever received, in 35 disappointing years. He thought about this as his self-announced "date" rolled a condom down his beautiful cock, and again, moments later, when he was penetrated by it. Darren...

Fat Bottomed Girl Pt. 05

by eviltwin52 on Jun 4, 2019
Gay Male

It's gotten to the point that I'm chained to my obsession to a fat bottomed girl. I've allowed myself to be molded into that mate Sheila wanted. I mean before Sheila I was a woman chaser. A woman with a big ass fascinated me, aroused me, and now I'm a slave to my fetish. Sheila dominates every aspect of my life. Me queering off for her is just another way fo...

Little Sex Toy Ch. 01

by keptsissy on Sep 26, 2017
Gay Male

Rough sex with a big strong man is something I'd always fantasized about. Ever since I can remember masturbating I'd think about being made to do things, dirty things for a man. I thought about being spanked, made to perform for a man, one that wasn't mean but very dominant, somewhat cruel and unusual but not terrifying. I had the fantasy in my head often....

Roommate Turned Me Out

by ralphcollant on Nov 2, 2020
Gay Male

It was a typical Tuesday afternoon after my last class for the day. I walked into my dorm room and found my roommate, Mike, watching porn on his laptop. This was not unusual for either one of us. Some of this junk could be quite entertaining. He nodded and said "Hey Tim" as I walked in and then waved me over so I could see what he was viewing. It was some pr...

Sissy

by MVP6 on Jul 15, 2020
Gay Male

This is my fifth letter describing my expanding awareness from a naive man with a desire to suck a cock to a man willing to explore his seedier side. (M+/M, oral, anal) In my first letter "Costume in a Costume" I describe how I dressed as a girl in a Halloween costume to trick an unsuspecting man into letting me give him my first blow job. In my second...

Gay Cave Escape

by Hypnodip on Mar 11, 2021
Gay

Drip! Drop! Drip! A staccato of water droplets add to a quiet and dark ambience. A nearby rock is dislodged, crashing with a large boom. You awake with a jump, chilled from the rock floor you were sprawled on. The room you're in is almost too dark to be traversed. You can see three ragged walls surrounding you, sprawling upward out of your limited night visi...

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Jail Time Ch. 02

by oralguy82 on Aug 18, 2017
Gay Male

Before, I had spent 2 weeks in the county jail and, I thought that was all done and gone, and would be forgotten. But about 4 months later, I was almost thinking how can I sign up for another 2 weeks. I felt humiliated about the experience, but so turned on too. More than once I had jerked off to the memory of that humiliation. A 25-year-old man thinking ab...

Simple Submission

by LoveIsUniversal on Apr 10, 2018
Gay Male

Heidi had a good life here in Southern California. At the age of forty-three, she had a good job and a lovely house. Living in the city of Arcadia was almost the equivalent of an island paradise. She had friendly neighbors who reminded her why she stayed in such a quiet and clean suburban community. They were good people, the kind that never overstayed their...

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,...

My First Time with Ryan

by elliotsconfessed on Dec 19, 2018
Gay Male

It was 2013 on a hot summers night. Me and Ryan decided to go camping and make the most of the beautiful weather! We were both 18 and fresh out of school both deciding what we were going to do with ourselves now we're "grown up". Ryan and I would often talk about what girls we would love to hook up with or see naked! These chats got us through our high scho...