Gay Sissy Interactive Stories

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The Making of a Master

by Littlepoppyhole on Oct 6, 2020
Gay Male

David lay on the dishevelled bed exhausted and still sweating after his recent sexual encounter with a man called Raymond. His hole was leaking semen onto the bed sheets. The sheets also gave off the aroma of anal mucus. This did not perturb David as he was deep in thought about the man he had served. He thought there was room for improvement in his sexual i...

Just a Number?

by NRMathis on May 9, 2018
Gay Male

Couples with large age gaps have some sort of assumptions that are automatic whenever people look at them or think about them. If it's a young man and an older woman, she's a cougar. If its an older man with a younger woman, she's a gold digger and he's her sugar daddy. If it's two gay men people assume a sissy-boy/daddy relationship. With lesbians, I have n...

Speech and Debate Pt. 08

by DAMackey on Sep 25, 2017
Gay Male

I hope you enjoy this chapter. Sorry it took me longer than usual to post this chapter. I had originally planned this to be ONE long chapter, but it proved too bulky. So now you get TWO chapters at once! Hope you enjoy it. This also means that now there will be a total of at least 14 chapters when the series is completed. Maybe more! DISCLAIMER: The follow...

When Love Takes Over Ch. 02

by fuzzyNOLA on Sep 25, 2017
Gay Male

I planned on going straight to the office after leaving the job site, but after thinking about my first meeting with Reed (and, if I was willing to admit it, a bit horned up by the luscious Rico), I decided to go home first. I knew Reed planned to work from home this morning before heading out of town on a business trip, so I hoped I could catch before he...

Nephew's Readjustment

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. ***** Cynthia's life had improved drastically in the past two years. Most people would consider getting a divorce at thirty years old pretty bad. A divorce due t...

Becoming the Bear

by papawerebear on Sep 14, 2017
Gay Male

By PapaWereBear and UrsusMajr (What follows is a work of fiction. Enjoy the fantasy, but please do not confuse it with reality. None of the incidents portrayed happened, and none of the characters are meant to depict actual persons, living or dead. This story contains descriptions of sex between consenting adult males. If such offends you or is illegal fo...

Field Maneuvers

by ikvdrakka on Sep 1, 2017
Gay Male

In the summer of 1993 I was a 1st lieutenant in the army engineers. My unit was on a training exercise in a god-forsaken piece of the high desert. We were going to be out there for two weeks, working by ourselves and in conjunction with other units. Pure field exercise, there wasn't anything around this place for miles. Any entertainment we were going to get...

Was I Raped? Ch. 02

by eviltwin52 on Sep 14, 2017
Gay Male

Note: See "Was I Raped" * 15 minutes after my new Daddy fucked me, I met him back in the bar. The sexual haze having worn off, I planned on setting him straight. "Look you brute," I said, mustering all the indignity I could. "I don't appreciate you bullying me like you did. I have half a mind to call the cops on you." Slap. Daddy had grabbed me by my up...

Curiosity Fucked the Straight Guy

by silkstockingslover on Sep 25, 2017
Gay Male

Editor's Note: this story contains incest content. NOTE 1: A special thank you to Estragon and Goamz86 for editing this lengthy multi-chaptered journey. Curiosity: Fucked the Straight Guy I can't explain for the life of me when I suddenly became curious. I mean I am 44 and have never found any man remotely attractive. Oh sure, I can tell when a man is goo...

Improper Advances Ch. 04

by bjmichaels on Sep 19, 2017
Gay Male

I became lost in the sucking. Every time I went faster, he would slow down the pace. I gently stroked his shaft and caressed his balls. My own balls were so painful I knew I wouldn't last much longer. This time when I furiously bobbed my head faster-and-faster he didn't slow me down. I was so consumed with the rigid pole of flesh inside my mouth I though...