Gay Sissies Stories

124 results
Orientation
Length
Source
Infinite Scroll

Bringing Out the Sissy in Fred

by 0ra1Master on Aug 18, 2017
Gay Male

"Yessss.., ooh yesss, aahhh! yesss! That's it! Thaat's iit! God it feels good, so good! Ohh Sammy! Fuuck mmee! Yessss, yessss, fuuck, fuuck, yesss!" Mary Pats nails were digging into my shoulders; her ankles were hooked on my ass cheeks. I wasn't sure who was riding who but it was what it always was, a great fuck. "Give it to me Sammy! Harder...., h.a.r.d.e...

Finding Friends In The Booth Ch. 03

by dodgeboy2 on Sep 15, 2017
Gay Male

After James pulled his cock out of my ass, Jack with his arm still around me started rubbing his cock against my ass still full of James cum. I pushed back with my ass until Jack pushed his cock into my ass some of James cum pushed out as he drove his cock inside me, I could feel my own cock getting so hard it felt like it would just burst. Jack was fucking...

Nephew's Readjustment Pt. 07

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, mind fucking and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. Comments, ideas and feedback are welcomed and sought after! ***** Cynthia did indeed end up masturbating herself silly later that evening, rewatchin...

How I Became a Sissy Pt. 01

by Yngwhiteboi on Jan 14, 2019
Gay Male

As a young man growing up I knew that I liked both men and women, but never had much success with either due to lack of confidence. Being only 5 foot tall and very small I had never been a hit sexually. To top it all off my shoe size was 5 in the UK. I was a rocker as well, which put off most people, shoulder length brown hair always in a pony tail, ripped j...

Black Cock Worship: A Man's Fall

by silkstockingslover on May 1, 2018
Gay Male

Summary: Straight guard learns of black inmate's power over all. Note 1: This is dedicated to the real Ken who retold this surprisingly largely true story. Note 2: Thanks to Tex Beethoven, thor_ph, Robert, and Wayne for editing. Prologue: I'm the prison guard and Kareem Mwangi is the prisoner, so you would have thought I had the upper hand, and until...

PIXIE Sissy Stripper Ch. 01

by EROTICbearscribe on Dec 24, 2019
Gay Male

The imposing shadow loomed over Benji blocking out the lights from the stage. "I asked you a question," a deep voice said. There were no other sounds in the club. The loud dance music had been turned off a while ago. There was only the clinking of dishes coming from the kitchen. 20 year old college student Benji knew someone was speaking to him, but the...

The Talent Scout

by eviltwin52 on Jun 5, 2019
Gay Male

The day I first met him was like any other day. Riding the Metro to work I was suddenly jostled out of my reverie by some one bumping into me from the back. Turning I found myself looking up at a ruggedly handsome man. His steely grey/blues seemed to pierce into my very being. I wanted to look away but was unable to do so. After a few seconds that seemed to...

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...

Finding a Perfect First Daddy Cock

by btmboi335 on Apr 3, 2019
Gay Male

This is the true story of the time I lost my virginity to Mike, an older man I met on the internet. I will always remember my times with Mike. His cock was one of those rare, perfect cocks that you can always recall in your mind in a second, so every time we fucked was memorable. I hope you enjoy our first time as much as I did. ***** For as long as I can...

My Wife's Hot Cousin Ch. 06

by funandbold on Apr 9, 2018
Gay Male

"Yes Aaron, I want you to fuck me!" Those were words I never expected to slip past my lips, but as soon as I said them I was glad I had. I don't know how we could become any closer than we had already become except for this. Aaron was changing me as a man and I couldn't think of another man I'd rather have it be. I had always considered gay activities and...