Gay Sissygasm Stories

9 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 SmutMD.com

Guys' Retreat Pt. 06

by Cyanlot on Sep 14, 2020
Gay Male

Part 6: Brianna, Used and Abused The humiliating show I'd been forced to put on for Kent and Vince with the two dildos had had an effect. I suspected that it had aroused Kent but I was vividly aware of its effect on Vince. His cock was hard even before I'd gotten it in my mouth. When I'd freed it from his pants, it sprang up, eager to fill my mouth. Now, as...

Guys' Retreat Pt. 05

by Cyanlot on Apr 21, 2020
Gay Male

Part 5: Brianna's Training "Vince had a terrific idea, Brianna," Kent said. "It's really going to make this easier for you." "Yeah," I said, noncommittally, knowing full well that whatever Vince had come up with wasn't going to be to my benefit, though I was sure it would benefit them. "Yeah. We've been downloading some videos for you to watch. You're goi...

First Time Fucked

by tinywhiteboi on Aug 18, 2017
Gay Male

It's a long story but I had by now been the chastised slave to my former Mistress for over 6 months. Over that time I'd been conditioned to be more and more subservient. She seemed to take particular pleasure in humiliating me in front of others, especially her friends. Most Friday nights she'd have a gathering at her house with 2 or 3 friends. I would serv...

Caught by the Neighbor

by justaguy84 on Oct 21, 2019
Gay Male

It's been a while since I had my first glory hole experience on a business trip. I found one that was close to where I live, but it was just... unpleasant. It is mostly inhabited by crack heads and homeless people. Since that hasn't worked out, I make due with porn and trying to play out my gay/bi fantasies on my own. When I get the house to myself, I take a...

You are a Sissy Pt. 01: Awakening

by Roland15Rollin on Dec 24, 2019
Gay Male

Are you ready? Are you ready, princess? It's finally time. It's finally time, princess. It's time to begin. Are you ready? I think you are, princess. I think you're ready. I think you've been ready for so long. You've been ready for your whole life princess. It's time to drop the mask and be who you are. Who you really are. What you really are. No more l...

You are a Sissy Pt. 07: Cuckold

by Roland15Rollin on Dec 24, 2019
Gay Male

Hello, princess. Hello again. I see you are back. That pleases me, sissy. It pleases me that you have come back for more of what only I can give you. The truth only I can give you. And we have come so far together, princess. We have come so far exploring the depths of your sissy feminine mind. And your mind is feminine. Make no mistake about it, princess....

Glazed and Filled at ABS

by Cumpup39 on May 12, 2020
Gay Male

When i finished preparing for the evening, douching out my sissy cunt, shaving and lubing, i went out to the living room where Master was waiting and presented myself. Kneeling on the floor and putting my hands behind my back, i cast my eyes to the floor and waited. After a moment, Master got up and i heard him approach. He looked me over and ran his big, r...

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...

First Time Seeing the Doctor Alone

by dudefromthebayarea on Sep 23, 2019
Gay Male

*Note: all actors in this story are 18 years old or older. ***** Patrick was at the table in his parent's kitchen, studying his calculus homework, when he winced and tugged at his crotch. The pain was there, burning. The head of his cock was red and itchy when he went into the bathroom to pee; the fact made his heart drop. He had no idea what it could be...