Gay Sissy Chastity Stories

970 results
Orientation
Length
Source
Infinite Scroll

Beauty and the Beast Pt. 01

by Suzzique on Dec 17, 2017
Gay Male

I hesitated a long time before I advertised on Craig's list. I was 18 and had left school two months before. I had a place at university for the following October, almost a year ahead. I was living at home and had a mindless temporary job in a solicitor's office that made no demands on anything but my time. I'm a very shy person and no one knew I was gay exc...

Forced Slutty Transformation Ch. 01

by beachboi_3 on Sep 14, 2017
Gay Male

Small towns are all the same. Racists, cows, and that one weird racist guy who sleeps with the cows. Personally, I just wanted to leave my town. My name is Carter, and this is how I went from promising high school student with a bright future, to a strung out slut, desperate for sex. I'm white, about 6 feet tall, and I'm built like a swimmer. That is, fairly...

Fraternity Slut

by oskarwild on Sep 14, 2017
Gay Male

College was great! High school sucked. And Sam was glad to leave it behind. He had been an awkward boy in high school. Short and skinny - only five-six and a hundred ten pounds - and pimply-faced, he had never been able to attract the hot girls that the jocks were able to get. But things began to change when he hit his eighteenth birthday shortly after gradu...

Research

by eviltwin52 on Aug 18, 2017
Gay Male

This story is dedicated to Kept Sissy who was so instrumental in helping me understand my urges. I was in the final phase of getting my Doctorate in psychology. My dissertation was to be on the difference between transgender boys, homosexuals, and sissies. You see, the transgender feels as though they were born with the wrong physical sex organs whereas i...

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....

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...

Progression Ch. 04: A Real Fitting

by klapperz on Mar 6, 2018
Gay Male

Nathan hung out with Jeff and his other flatmates for the day. He had been so focused on Ryan and Jack that it was nice to have a break and be normal for the day. They went to the pub for lunch and then watched some films. Before he knew it, the day was over and everyone was heading for bed. The next morning Nathan woke up for work. He panicked, remembering...