Gay Sissy Roommate Stories

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Orientation
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Infinite Scroll

Fun and Games Ch. 06

by jm02201960 on Sep 15, 2017
Gay Male

The next morning my ass, understandably, felt like it was on fire and I knew I had to give it at least a few days to calm down, which I did. The nearly nonstop sex I had recently enjoyed provided me with excellent visual images and the masturbation sessions were amazing. But taking on a cock anally at this point was unthinkable; my body was not used to it an...

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....

Wife and I Get a Roommate Ch. 01

by tonyl65 on Sep 25, 2017
Gay Male

It was the early 80s; I was taking a full load in college and working full time. At nineteen I was making good money, going to school, and just married my high school sweetheart. I know it was too young, but it was 80's and I thought the only way out of my parent's house was to get married. We were married for a year now and, at twenty, we had a nice two bed...

This Thing Called Life

by noodneighbor on Sep 14, 2017
Gay Male

I had it all figured out this thing called life, or so I thought. Turns out life can kick you in the balls when you're not looking and turn your whole world around. I'm a jock, sorry, was a jock; I guess once you graduate high school unless you go pro or get a scholarship you're not technically a jock anymore. I still run and lead an active life though and t...

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...