Gay Sissy Bet Stories

4,726 results
Orientation
Length
Source
Infinite Scroll

How it Happened

by loverofintersex1 on Sep 14, 2017
Gay Male

This is a fictive tale, and any resemblance to anyone outside of it is purely accidental. Do not read any further if you are not of legal age in your jurisdiction. ***** I was supposed to suck his cock and then butt-fuck him, so we'd arranged, or I thought we had, but in between making out he rolled me over and got on top, his weight pressing me down, legs...

An English Boy Gets Turned Out Ch. 02

by RustyRover on Sep 14, 2017
Gay Male

Sam woke up the next morning with his usual morning hard on. As he put his hand on his erection yesterday's events suddenly leapt to the forefront of his mind. He felt himself blushing as he was submerged with a wave of humiliation. He remembered he was going to be working in a gay porn shop for the foreseeable future, he remembered picking up an enormous di...

Cream Puff Ch. 02

by RubixStu on Mar 12, 2019
Gay Male

When I woke Sunday morning, I was completely nude. I'd showered and removed my makeup before bed. The image in the mirror as I pissed standing up was totally male. I was clearly a man, in appearance at least. Sure, I was totally hairless, but that didn't make me less male. Inside I didn't feel manly. I didn't feel independent, willful, or strong. I felt vu...

Analyzed From The Bottom Up

by Cumfusion on Sep 14, 2017
Gay Male

We were losing power yet again and Jock was getting angry. His eyes were fiery and with his big arms stained with oil and diesel fuel he might have looked really threatening to anyone else. I hadn't had much time to get to know him. He was like you could say 'a good solid looking trucker'. I suppose, if I am to be perfectly honest, I had noticed his physique...

Drunk Friend to Sissy Slut

by olybiguy27 on Sep 14, 2017
Gay Male

What follows is the completely true story of the weekend that changed my life. This really happened to me and took place in the summer of 2008 just after graduating from high school. My name is Andrew and I was a major stoner in school. I had a lot of friends, mostly due to the fact I always had really great weed that I would get from my rich old neighbor...

You are a Sissy Pt. 03: Body

by Roland15Rollin on Dec 24, 2019
Gay Male

Hello. Hello, sissy. You have come back. You have come back again for another session. Welcome back, faggot. My sexy sissy faggot bitch. I am so glad you have come back. But you have no choice, do you, sissy? You have to come back. You need to come back. You need to hear my voice. It is the voice of truth. The voice that tells you what you are. What you tr...

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....

It Could Be Worse Ch. 07

by eviltwin52 on Sep 14, 2017
Gay Male

We've been in service to blacks for 6 months now. Mom, my wife Cindy, and I have completely devoted ourselves to the pleasures of the Superior African race and Leon. The club where Leon has us working is a nice dinner club on the waterfront in S.W. Washington, DC. We work as greeters and servers with a few other white couples and single white women. All of...

You are a Sissy Pt. 04: Women

by Roland15Rollin on Dec 24, 2019
Gay Male

Hello again, sissy. Hello, my sissy bitch. I am so happy that you are back yet again. You love coming back to continue our sessions, sissy. You love coming back because I am helping you. You need my help. You know you need my help, sissy. You need to come out of the closet and let the world know what a gay cocksucker you are. You need to let the world know...

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...