Gay Rubber Sissy Stories

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Sissy Bottom Has a Nite Out

by lostsoul1974 on Sep 14, 2017
Gay Male

My wife had gone out of town on a weekend business trip, so I invited my Fuck-buddy Eric over for some fun. I met Eric a couple years ago when he passed me his business card through a Glory Hole after he had fucked my asshole raw. After I eventually called him, we hit it off and have been friends ever since. Of course, hot raunchy sex can really help cement...

Sissy Bottom Has a Nite Out Ch. 02

by lostsoul1974 on Sep 14, 2017
Gay Male

Last night, my friend Eric and I had some really hot sex down at the Adult Theatre. Eric had me wear a pair of my wife's panties and I was a sissy fuck-boy for a whole theatre full of horny men. My wife is out of town for the weekend, so we are gonna be as lecherous as two bisexual fuck-buddies can be. This morning, I awoke to the sensation of Eric's hand s...

PIXIE Sissy Stripper Ch. 03

by EROTICbearscribe on Jan 6, 2020
Gay Male

Darryl Powers was on his way to one of the two popular nightclubs he owned. His new sissyboi, Benji, was beside him. The boi looked pensive and vulnerable, especially sitting next to Darryl. At 6'5 and a muscled but well-sculpted 230 pounds Darryl dwarfed the, for lack of a better word, 'petite' college boy sitting next to him. Anyone seeing the two pass b...

Sissy's BBC Submission

by tawnysuede on Sep 19, 2017
Gay Male

Chapter 1 - First Contact "Tyler! Snap out of it - you're staring again, and he's noticed!" Jack's voice whispered hoarsely in Tyler's ear as the hot water from the shower drummed across his back. There were just the three of them left in the shower now. Basketball practise had been over for more than half an hour and the most of the players were showered...

Sissy Bottom Has a Nite Out Ch. 04

by lostsoul1974 on Sep 14, 2017
Gay Male

Well, following some completely depraved sexual exploits last weekend, I entered the workweek thoroughly satisfied! For those of you not following the series, (see my cocktales) my fuck buddy Eric and I had some really hot gay action at a local Theater, as well as a raunchy, fem-dom 3-some with my wife Toni at home where she showed me all over again why I...

The Birth of a Sissy Pt. 03

by sissymedic1426 on Sep 14, 2017
Gay Male

By my sophomore year of college I had performed well enough in the class room that I had earned a few scholarships. This meant that my folks were saving money while I was getting my learn on. It also meant that my dad had promised me that if I rode it out for one more year in the dorms that by my junior year I could move off campus. The thought of finally ha...

Sissy Slave Toy

by slavegurl_veronica on Sep 16, 2017
Gay Male

Where it all began was at gym class in my freshman year of college. Gym was a course requirement for freshmen and I couldn't wait for it be over. I was skinny and weighed only about 130 pounds. I was not at all athletic and one of the smaller guys in the class. Fortunately though there was another guy named Alex, who like me, was also decidedly not jock mate...

My New Daddy Ch. 03

by sissytoy20 on Mar 6, 2018
Gay Male

The buttplug that Sam had unceremoniously forced inside my tight asscunt had hurt like hell, but I'd enjoyed the feeling of being forced open with no warning. The little, pink butt plug wasn't very large, but it had felt like a giant donkey dick in my ass. It had flashed by in Sam's hand so quickly, maybe it was larger than I thought. It felt huge in my butt...

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...

Sissy Dream Come True

by Sjen451 on Oct 6, 2020
Gay Male

It was Friday and I had one job left before I could start my weekend. I didn't have much planned other than watching some of my favorite sissy porn and playing with a few of my larger dildos. Not too exciting, but it's how I spend most of my weekends when I don't have other plans. Today I wore my red lace panties under a pair of black break-away running pa...