Gay Turned Sissy Stories

18,675 results
Orientation
Length
Source
Infinite Scroll

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...

Beauty and the Beast Pt. 03

by Suzzique on Jun 3, 2019
Gay Male

"Well, well!" said Daddy in a tone of mock surprise, "Your Uncle Ted has made it here after all. And for once he's timed it just right." "You promised," I cried out, on the edge of tears again. "I lied, you dumb sissy. I lied." He laughed. "Cut the jokes, Jack. Give me the bitch. I've come a long way to get my cock up the little slut. I want her now." "...

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...

Zebulon

by MVP6 on Jul 6, 2020
Gay Male

This is my fourth 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. In my first letter "Costume in a Costume" I describe how I dressed as a girl in a Halloween costume to trick unsuspecting men into letting me give them my first blow job. In my second letter "Gloryhole Illust...

How Did This Happen to Me?

by bjmichaels on Dec 12, 2018
Gay Male

I live in a very expensive condo in one of the most exclusive and prestigious buildings in town. Most of my neighbors are very wealthy retirees. They generally purchase their condo's with cash. I have a five-year plan where my condo will not only be paid off in full, but I will also have a net worth in seven-figures -- yes, you heard me right -- I am thirty...

Off the Grid

by puzziboi on Jan 22, 2020
Gay Male

There sat a cabin. Small. Sturdy. Well-built. A short hike off the Appalachian Trail. Just two-and-a-half miles from the nearest town. The owner was a man in his mid-fifties with gray-green eyes, a dusting of frosty hair on his head, and a full, untamed white beard that covered much of face and came down to his upper chest. The man had two dogs - both mutts....

Daddy's Girl

by oskarwild on Sep 25, 2017
Gay Male

The Hitchhiker It had been snowing all day. A wet, heavy incessant snow that was covering everything including the highway. Combined with a wind-chill factor in the teens, Christopher was almost frozen stiff. He was elated when the huge semi pulled over to pick him up. He climbed up into the cab and smiled thankfully at the driver. "Thanks a lot mister. I...

Gay Cave Escape

by Hypnodip on Mar 11, 2021
Gay

Drip! Drop! Drip! A staccato of water droplets add to a quiet and dark ambience. A nearby rock is dislodged, crashing with a large boom. You awake with a jump, chilled from the rock floor you were sprawled on. The room you're in is almost too dark to be traversed. You can see three ragged walls surrounding you, sprawling upward out of your limited night visi...

Open in Reader

First BBC

by smoothbtm76 on Jul 6, 2020
Gay Male

I always thought of myself as bisexual. I had gotten my cock sucked by older men who liked twinks and I had sucked cock in turn. I had topped older men and had my ass played with and toyed and even fucked a couple times but hadn't really gotten into that too much. I had been to bookstores and theaters and played there but nothing really changed. That is, unt...

New Neighbor Ch. 01: Steve Pt. 01

by rimaday on Nov 18, 2019
Gay Male

My name is Steven Vincent wife and I had been married for eight years and lived in a newer middle-class housing development outside of Dallas when this story began. We were one of the original units in the development that now had over 150 houses with plans to double that in the next eight to ten years. We had lived next door to an older couple that retired...