Gay Sissy School Stories

8,015 results
Orientation
Length
Source
Infinite Scroll

Fantasy Out Of Control

by gbr2004 on Aug 18, 2017
Gay Male

I'm a divorced man living in Las Vegas. Recently retired, live alone and live a relatively normal life. I'm in decent shape for my age, 5'8", 180, and stocky build. I have been straight for the majority of my life. For the last few years, I have started to think more about getting together with another man. It goes beyond just this, as I want to be submissiv...

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...

A Model for the Life Class Ch. 01

by andy190 on Sep 14, 2017
Gay Male

I had travelled down to King's Cross station alone to start my new course at the Slade school of Art. I was delighted to have been accepted and was keen to start the fine art work. My favourite aspect was figure or life drawing and sculpture and my teachers had praised my mastery of paint as I depicted both male and female forms with no clothes on. I was goo...

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...

The Man Cherry Fetish Ch. 01

by blondeallover_00 on Sep 2, 2017
Gay Male

This is the story of how I came to be an Asian cock and ass freak. I had no idea how much I craved dick until I became a student in the eastern U.S. I was attending a party that was being thrown for the better students in my department by professorial graduate school assistants. The event was located at a professor's home who was known to "swing both ways",...

My Husband in My Panties Pt. 02

by eviltwin52 on Dec 9, 2019
Gay Male

Please read Part 1, My wife's perspective first. Johnnie's perspective If you read my wife's version about how much I enjoyed wearing her panties please let me explain myself. Not only did Cin help me realize and accept my fetish but she freed my inner submissive and bisexuality. I'm not here to refute nor challenge Cin's interpretation of anything. It's...

Party with Wife and Her Lover

by colleenslittletoy on Sep 14, 2017
Gay Male

My girlfriend of six months came home all excited. This was a good sign I thought because I was afraid things had been getting a little dull lately. It seemed like she wasn't really into our lovemaking sessions and they were getting fewer and fewer. "I need your help!" she exclaimed when I asked her why she was so excited. "There is an important business di...

Nephew's Readjustment Pt. 07

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, mind fucking and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. Comments, ideas and feedback are welcomed and sought after! ***** Cynthia did indeed end up masturbating herself silly later that evening, rewatchin...

Fucking Matron!

by HannahSavannah on Aug 17, 2017
Gay Male

Fucking matron was the national sport at our public school (that’s “private school” for Yanks). It was a rite of passage without which no future Australian captain of industry could hope to attain a Dick Grasso-esque remuneration package. But final year frolics came first. We'd reached 18 and were ready to rock and roll. We were wizards of wanking . . . mas...