Gay Sissy School Stories

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His Sweet Boy Ch. 02

by Her11 on Jul 20, 2020
Gay Male

Ben paced outside the Harris Teeter he worked at part-time. This was crazy, no, insane. Why had he said yes? Stupid so stupid. It was a bad idea from the very beginning. Going to the BDSM club, then even talking to Eric in the grocery line instead of pretending not to remember him but no, Ben was a horrible liar. He always got twitchy when he tried, so afte...

Sissy Sundays

by BlinkOneSomething on Apr 13, 2020
Gay Male

It was the summer of nineteen-ninety, I had just graduated high school and was partying like a rock star. Occasionally when my friends would drop me home late at night, I would walk the block or so to a nearby two lane highway that led out of Boston and stick my thumb out, not ready to end the night just yet. I had a massive libido but knew the chances of a...

The Birth of a Sissy Pt. 02

by sissymedic1426 on Sep 14, 2017
Gay Male

Upon my return from Orlando I was tasked with making a decision of where I would go to school in the fall. At first I was intrigued by the possibility that I could go the University of Central Florida, but quickly remembered that I had never stepped foot on the campus while in Florida. So it was a decision between the schools in little old North Carolina, at...

Drunk Friend to Sissy Slut

by olybiguy27 on Sep 14, 2017
Gay Male

What follows is the completely true story of the weekend that changed my life. This really happened to me and took place in the summer of 2008 just after graduating from high school. My name is Andrew and I was a major stoner in school. I had a lot of friends, mostly due to the fact I always had really great weed that I would get from my rich old neighbor...

Sissy for Older Men Ch. 01

by sissyforold on Aug 18, 2017
Gay Male

These experiences I'm writing about, are made from my former relations with older men ( being only with older men until now:) , only names and places are not the real ones. * I should start with the beginning into the world of older gay men, which was 10 years ago, when I was 19 years old. Until then, I've been only curious and had only fantasies about be...

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...

A Very Dirty Little Sissy 'Girl'

by keptsissy on Aug 31, 2017
Gay Male

I love to please my boyfriend. I masturbate thinking about that. A lot. To hear him when he's in me, on top of me, lost to my tight little hole or my mouth, I love the sound of him, the 'man' noises he makes! But as much as I like to please him, I just like to please men. Do I ever. I've been at it since just after high school. And there is nothing hotter th...

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...

My White Boy Sissy Pt. 01

by wolf_hunt on Feb 25, 2019
Gay Male

This is part 1 of an ongoing series. It's just an intro with only a blow job scene. In future chapters there will be more including forced feminization, anal, humiliation and much much more. Hope you enjoy my story. All characters involved in sex are 18 or older. This is from the perspective of a black teenager as he turns a sissy nerd into his bitch. ****...

How Adam Became a Sissy Fuck Toy

by SlutFucker510 on Dec 2, 2019
Gay Male

For most of his life, Adam was your run of the mill straight guy. He was only attracted to women and when with a woman, he was always in the dominant role. He loved rough sex and being aggressive, even borderline abusive, to the girl he was fucking. He was proud to be a hard fucking, dominant, straight male. That is, of course, until he moved to San Francis...