Gay Sissy Training Stories

2,817 results
Orientation
Length
Source
Infinite Scroll

The Pirate King Ch. 15

by nakamook on Sep 14, 2017
Gay Male

First things first; if you are here without reading the previous chapters, I *highly recommend* that you go back and read those first. This is a plot heavy journey, and we'd love to have you along for it's entirety. Don't worry. We'll still be here while you catch up :) Second, and most important: Wow. I have been feeling. Humbled. Awed. Like my stomach is...

I Know What I'm Doing Ch. 03

by AzanianHeat on Sep 25, 2017
Gay Male

~Aiden~ "Bloody hell!" "Yes, I agree." Seven out of nine Montgomerys were in my study. I was seated on my leather chair, my head on my desk. The last time I'd spoken was about ten minutes ago. As far as I could tell without actually lifting my head, the other six were having a hard time sitting still. They moved about as much as they talked. "What just h...

Why: Another Night, and Bad Timing

by hasnoalias on Sep 16, 2017
Gay Male

All characters in this story are above the age of 18. ***** It had been a long day and an ever longer swim practice. I had just walked back to my apartment. I was actually beginning to think that I could relax tonight and not have to service Ben or Dan. I had not seen either one of them in over a week now, as I rode the elevator up to my floor and walked t...

Firecracker Ch. 02

by Cruel2BKind on Sep 25, 2017
Gay Male

*I'm back, Baby* The boy woke up, as he always did, opening his eyes to see the protective circle, etched in deep blue lines on the ceiling above his bed. His mother's hand was on his shoulder. The woman was tall, fierce in a way that many had a hard time describing. Her hair was fire-red. Her eyes had a ring of silver around the pupil, very close, very th...

Now or Never: Escape to Freedom Ch. 02

by CE300 on Sep 26, 2017
Gay Male

As always, this story is completely fiction and any likeness to real events or people are completely coincidental. My stories contain a lot of detail and dialogue so if you're looking for a short to the point story this is not for you. If you looking for a story that contains suspense, drama and adventure than this is it! This chapter contains an extreme sit...

The Bottle and the Bi-Curious

by Vaginalpuppetry on Jul 24, 2018
Gay Male

This story is a work of fantasy, though based largely on missed opportunities. It is categorized as Gay Male, but is mainly about exploring bisexuality in a MMF threesome, and includes heterosexual sex. This is my first time writing this kind of story, so I do apologize if it's not up to par. Still, I hope you enjoy my fantasy as much as I've enjoyed writing...

Curious No More Ch. 10

by bicurve on Sep 25, 2017
Gay Male

Thank you for your patience! I really appreciate all your emails and support. But enough about me; let's get to the stuff you men want. * "Are you looking forward to getting your ass used and filled?" I pushed my crotch into him, my hard cock apparent. "Does that answer your question?" "Let's get dressed and get some food. Alex and Cory are going to call...

Sex Agogo for Gregory

by JASONSHOMOEROTICA on Aug 18, 2017
Gay Male

An Imaginary Homoerotic Tale By Jason Land * FOREWORD This is a sequel to my earlier story: "Gay Sex for Gregory", which was posted on the Literotica website on 09/19/2015 (September 19 2015). Whilst the present story and can be read as stand-alone tale, I would recommend my readers, first to read the earlier story, "Gay Sex for Gregory" as it will make...

Letting Go Ch. 04

by tantepicante on Aug 30, 2017
Gay Male

*Simon "I'll see you soon?" Reggie asked me before I got out of his truck. "Yeah," I said barely smiling. "I hope everything gets better," Reggie said sincerely. "I'm sorry this had to happen to you. Call me if you need anything." I barely nodded in response as I waved him goodbye. I went inside my apartment and flopped onto the couch. I let out a frus...

Horseshoes and Hand Grenades

by STLwriter on Aug 20, 2019
Gay Male

Hey y'all! This story is particularly kinky and has dirty talk, pup references, and other kinky things that you may not like! It is based on a bar in Saint Louis called JJ's but with quite a bit more kink and sex. Please enjoy! _________________________________________________________________ "Dude, I don't know about this..." "Relax, bro. You were the o...