Gay Sissy Cuckold Stories

804 results
Orientation
Length
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Infinite Scroll

It Could Be Worse Ch. 06

by eviltwin52 on Sep 14, 2017
Gay Male

In chapter 5 Leon took control of what he called his new sissy and fucked Cin into submission. We both became addicted to his superior black cock. Besides falling for his cock, Leon's predatory nature was evident. He wants Cin and I to prostitute ourselves for him. In the throes of black cock lust, we agreed. It could be worse Part 6 "Did you remember t...

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...

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...

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...

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...