Gay Sir Stories

4,065 results
Orientation
Length
Source
Infinite Scroll

Serving His CO

by panamacock on Dec 25, 2019
Gay Male

This story is a work of fiction, although some the ideas were inspired by real conversations. Fiction does not require the use of condoms for safe sex, but real life does. Please always use safe sex and protect yourself accordingly. As always, comments about the story are appreciated and can be directed to my profile. 2017 panamacock ***** Brett walked i...

Princess

by skinnysailor on Mar 2, 2020
Gay Male

I'm Dan. My lover, Rex, calls me 'Princess' as in his little fairy princess. He told me how tonight's date wanted me to dress. Very specific. Three inch strap on spike heels. An ankle length skirt. I chose my dusty blue wool one. A see through blouse. I'm wearing my pink one with the frill collar and cuffs. Panties, no bra. I put a little rouge on my nips....

My Visit to the Dealer Shop Pt. 02

by ibjtjones on Aug 20, 2018
Gay Male

Exactly on the hour Thomas texted me, the ball stretcher and magnetic balls were still in place. He texted me hourly as ordered. I talked to a friend of mine and after the next to the last text I had Reggie deliver a package to Thomas. The package contained 2 more pair of magnetic balls and another stainless-steel ring. Reggie told Thomas he would help. I k...

A Boy, a Daddy and two Tuxedos

by ThomasStevenson on May 21, 2019
Gay Male

"That suit makes u a horny little lad, doesn't it?" It was another text from Mr Matthews. Thomas was out at a bar with his co-workers, and he'd just sent Mr Matthews a picture of what he was wearing: a fine navy pinstripe three piece suit with a bright pink and blue striped tie and a lavish pocket square spilling out of his breast pocket. So Thomas texted...

Down The Path Ch. 02

by gbr2004 on Sep 14, 2017
Gay Male

Next chapter in my story of my domination by a stranger I met online. * I waited to hear from him again. At first, I didn't know if I really wanted to get together again. The first time we met, at times it was a little more intense than I was looking for. After a few days I couldn't get him out of my mind. I couldn't believe how badly I wanted him to call...

Chore Bitch Pt. 02

by travelsforfunxxx on May 12, 2020
Gay Male

Quick note: This story includes CMNM, humiliation, domination, submission, and objectification. But it doesn't have any oral or anal sex - - - If you're looking for oral/anal, then this may not be the story for you. Late in the afternoon, I got dressed as instructed -- in a jock strap, tight jeans, plain white t-shirt and boots. The jeans were super tight...

The New Slave Ch. 02

by martin_x59 on Sep 14, 2017
Gay Male

I would like to start by saying I am new to writing so I hope you don't judge me too hard on my literary naivety. Nor am I experienced in Bondage or Master Slave relationships. This story is pure fantasy from my part and is about what I find erotic and stimulating. Please bear this in mind when reading the story. I hope you find it as stimulating reading as...

One Sub Stud Ch. 02

by tazemebro on Sep 14, 2017
Gay Male

AUTHOR'S NOTE: The series One Sub Stud is a continuation of the stories about Chris and Justin, which began in Chris Donaldson and continued in Mr. One Fifty-Eight. While each chapter is a short story in its own right, you will probably enjoy this episode much more if you have already read both of the above series, as well as Chapter 1 of One Sub Stud. The b...

Highway Patrol's Lucky Night Pt. 03

by ibjtjones on Jan 6, 2018
Gay Male

When the boys got home Les texted me as instructed. I ordered him to video call myself and David. Les did as instructed, after David joined in I told both boys to strip one at the time and remove the eggs from their asses displaying their selves to us. Will removed his first and turned it off. Next Les removed his and turned it off. I ordered the boys to kn...

Fair Game

by trevorm on Aug 18, 2017
Gay Male

I'd passed the cop about a mile back. He'd been standing there, arms folded, next to his police regulation Harley in a pull-in at the side of Route 10. Now he'd reappeared in my rear view mirror, getting closer by the second. Every now and then, the sunlight caught on his dark glasses and dazzled me. He followed for a couple of miles while I kept an eye on t...