Gay Sissy Stories

744 results
Orientation
Length
Source
Infinite Scroll

The Hanky Code Pt. 14

by His_fag_wife on Sep 14, 2017
Gay Male

The warmth of the sun hit me after such a long time in the dark and dirty recesses of Master S's world. The fact I was wearing heavy duty rubber panties and bra became all too apparent as I started to perspire, not that I could take my hoodie off in the area I was about to walk through and with what I was wearing under my shirt. I started to walk on my sti...

Peter Three Hundred

by exaucer on Sep 14, 2017
Gay Male

John was a distinguished looking man and ever so friendly. Young Peter was not exactly sure what he did in the hotel but he always seemed to be on his floor when Peter came out of his room or in the foyer when he returned to the hotel after work. John was such a big man, very handsome in a rugged sort of way and always took the opportunity to put his arm aro...

Aquata Cove Ch. 37

by Feare909 on Sep 14, 2017
Gay Male

Chapter 37: Boundaries Merrick sighs as his gills wavered on the sides of his head. It's been 25 suns since his captivity. It's almost been a whole moon since he's seen Adam's wonderful face... After the first while Merrick was here, he felt as if he can't trust a single human in this place – Nigel especially. It's not like that man is entirely bad. Mer...

The Mudroom Ch. 02

by Kent100 on Sep 14, 2017
Gay Male

Recap of The Mudroom Part I... To catch you up... In my mind, my worst fears had just been confirmed by my cousin John. It was actually his big cock that I had sucked off at what I thought was my anonymous gloryhole setup at my house. We had hooked up off a Craig's List ad that I had posted and I was mortified with what he just said to me at the family par...

The Duplex Ch. 01

by TheCandyManCan13 on Sep 1, 2017
Gay Male

Chapter 1 - An Unexpected First My wife Eleanor and I (Peter) had been married for four years when the events I am about to describe to you took place. We were 25 years old and still madly in love, but we had started talking about expanding our sexual lifestyle outside of our own bedroom. I am of largely European descent, brown hair, 6'2 (1.89 meters) and 1...

A Matter Of Size Ch. 03

by quipogo on Sep 14, 2017
Gay Male

Hi, This is the third part of my story A matter of Size. I included a Prologue in which I summarize what happened in the other two chapters, so if you do not remember or simply you do not want to read those parts, you still will be able to follow the story. I hope you like it, thank you very much for reading it. ***** Prologue I kept telling myself, "how...

Exploring my Sexuality Ch. 03

by alexis19901 on Jul 6, 2020
Gay Male

I could have put this story in a number of categories but it consists a lot of gay sex so that's why I've picked it. It does contain some elements of taboo, group sex, crossdressing and gay sex. The other chapters do provide some of the back story. After my last meeting with Mark, I went back to my normal life. Going to work, college and seeing my girlfrie...

To Have a Sweetheart - David Ch. 02

by kaitslou on Sep 14, 2020
Gay Male

I woke up alone once again, but I guessed that it'd probably start being like that, an early bird and a night owl as we were, trying to accommodate the others habits. Rolling around in the bed I noticed Luke had folded up my clothes nicely from the pile I left them in, I was going to wear them anyway, what's the point? Oh well, what ever rocked his boat......

A Tale of Two Cousins

by fantasyhunter2 on Aug 18, 2017
Gay Male

Authors Note: This story includes descriptions of both homosexual and heterosexual liaisons between first cousins. If you find either gay male sex or incest objectionable you should try another story. * It was March and I was on top of the world. I was in my second year of college and had finally adjusted to life outside the cocoon of growing up protected...

Salvation

by EroticMonster on Aug 18, 2017
Gay Male

I swallowed the warm sticky spunk and held onto Hassan's cock until it was flaccid. He sighed several times and remained motionless with his eyes closed. With gentle motions I rolled the softening meat around my mouth. Every so often his thigh twitched. "That was amazing." He whispered at last. I hummed into his groin. "I can't believe I let you do it again...