Gay Sissy Schoolgirl Stories

895 results
Orientation
Length
Source
Infinite Scroll

What Happens in Saratoga

by timmywells on Sep 1, 2017
Gay Male

Roy Sharpe felt like his life was turning around, after having gone through a rough patch. Roy had gotten married a couple of years ago, and right after he made Mindy his bride, he lost his job as the economy tanked. Now newly employed, Roy felt like a man once more. As a representative for a winery in the Finger Lakes region, Roy was hired to work all of t...

College Fund Ch. 04

by bjmichaels on Sep 14, 2017
Gay Male

The two guys who Ally had told me to watch, slid out of their booth and I saw them walk out the back door of the bar. One was short, maybe my size, about forty-years old; the other was older, bald and quite fat. Earlier, I had witnessed the fat guy push a twenty-dollar bill to the younger man. "The younger guy is Eddie," said Ally. "He used to work at the f...

Pony Boy Ch. 06

by ChestersBoi on Sep 14, 2017
Gay Male

New readers – don't start here! This is chapter six of Pony Boy. My apologies for the long wait. It won't make too much sense unless you've read the rest so, if you're new to this story then I strongly recommend you find chapter one and start there. Usual stuff – we're all fictional and over eighteen. ******* I didn't move, I couldn't move, nor could I...

A Boy Who Came In from the Cold Ch. 12

by SadieRose on Apr 3, 2019
Gay Male

A BOY WHO CAME IN FROM THE COLD – CHAPTER 12 "BOYS ON FILM" © Sadie Rose Bermingham 2006 Apologies for the delay to Chapter 12. I've been swanning around Europe and London enjoying myself so things have gotten a little behind. Which, by happy coincedence, is exactly what Aldo and Barclay hope to get themselves at the end of this chapter! As usual, the a...

James and the Gloryhole

by jamesale2003 on Jun 9, 2020
Gay Male

This story is a part of a short series of stories following James a forty-something straight married man who has developed a love of cock sucking. Other stories are based on true events. This is what he would like to do; visit a gloryhole. It's a story about the protagonist setting up multiple scenarios to fulfil his urge while on a week-long business trip...

Hotel Room Nights Ch. 03

by WhitMan35 on Jun 9, 2020
Gay Male

"Hey," he calls out, looking at me seductively. The jets of water are hitting his body, pronouncing his muscles that much more, making him look that much more delicious. He turns his attention from me to the water, and joins his hands to make a cup. He takes some water and raises his hands to above his head, pouring the water into his hair. He turns his eye...

Two of a Kind Ch. 02

by Cia81 on Sep 14, 2017
Gay Male

Bashta didn't understand the looks that Piscel kept shooting at him. His smile seemed a bit less than friendly and a bit mocking, as if he was laughing at him. Maybe he was actually looking at Cavel, since Bashta was walking beside him. Bashta wasn't able to fight his fascination any longer; his dream the night before made that clear. That morning he had sta...

The Hookup: Beginnings

by SemiStraight on Nov 18, 2019
Gay Male

Some of my stories are true, some have elements of truth, and some are pure fiction. This one falls into the true category and I haven't decided how much to admit yet. I keep a couple of the hookup sites on my hidden web browser. The thoughts of hooking up ebb and flow and occasionally I use the mail feature to communicate to all the guys who send smiles, w...

Sporting Chance

by perihelion on Aug 30, 2017
Gay Male

Two hours after the school board hired me, I sat with my new principal in his office. "Jeremy, I'm glad you decided to call me. I just wish you'd done it sooner so we could talk." "It's like I said, no point in bothering you until I completed the courses I needed to teach in Georgia. I still don't understand why I had to take those extra classes if I didn'...

Rest Stop Management Pt. 03

by rimaday on Dec 24, 2018
Gay Male

I awoke around 4:45 on my belly, my red panties a little twisted and crusted with dried cum. I could feel Big Daddy's deposit oozing down my taint and hardening in the panties. I could not believe, this was not some kind of twisted dream but my stretched leaking asshole took away all doubt. Twelve hours ago, I was kissing my beautiful wife and leaving for an...