Gay Pantyhose Sissy Stories

820 results
Orientation
Length
Source
Infinite Scroll

I Turned Myself Out Ch. 04

by drmweaver705 on Sep 14, 2020
Gay Male

All characters are over 18. This story contains bisexual and cuckolding activity as well as fetishistic name-calling. If you don't enjoy these things, this might not be the story for you. *** Porn seduced me early in life and, even as a married man, it commands part of my loyalty to this day. It happened that I became bored, or maybe just desensitized, to...

Rape Fantasy

by MrJimJim on Oct 3, 2018
Gay Male

Editor's note: this story contains scenes of non-consensual or reluctant sex. * Rape fantasy First off, let me just say this is a 100% true story. It has taken me almost 2 hours to write down because I keep stopping to jerk off when I remember the sexy parts of what happened to me. So I've had a rape fantasy for many years, but never found anyone willing...

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...

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...

Nylon Suck Again

by nylondad on Sep 16, 2017
Gay Male

My cousin Jimmy and I burned up the telephone lines after our first meeting. In that meeting I had "borrowed" a pair of my sister's stockings and gave them to my cousin as a gift. He and I had a thing about women in stockings and he would focus on my sister. I tried the stockings on at his home one weekend and I ended up sucking him off twice that weekend. T...

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....