Gay Sissy Training Stories

2,817 results
Orientation
Length
Source
Infinite Scroll

Andre Finds Love Pt. 03

by eviltwin52 on Aug 18, 2017
Gay Male

See chapter 2 where my father-in-law fucks me while my wife is away on our honeymoon with her black lover. For those of you who wanted to know what happened to joanie in the final chapter of "It Could Be Worse", the mystery is solved. ***** Part 3: Tomorrow, I thought to myself happily. Lee Anne will be back tomorrow. And her black lover, Leshaun. I...

Cherry's Graduation Party

by CherryWood on Aug 30, 2017
Gay Male

I finish applying my lipstick and take one last look at myself in the mirror. I'm almost stunned at the reflection that stares back at me. After months of training and feminization I look like the perfect slutty fuck toy. I feel my little cock begin to get hard and strain against my chastity device as I look over my changed body. The strict exercise regimen...

An English Boy Gets Turned Out

by RustyRover on Sep 14, 2017
Gay Male

I was born in the USA but had never knowingly lived there. I was the only son of a British diplomat and I was born during his posting to Washington. By the time I was two we were off to another posting in another country. At the age of 8, I was sent off to an all boy, boarding school in England, but every holiday I would go to my parents in whatever country...

A Perfect Confluence

by eviltwin52 on Sep 21, 2020
Gay Male

Sometimes shit just happens. Maybe it happens for a reason, maybe it's just the perfect confluence of events. In my case I honestly believe it was just that, the latter. An unseen force guiding me through life, steering me to and through events which shaped my future and ultimately my life. This is the story of how I went from a normal, pussy chasing asshol...

Exploring my Sexuality

by alexis19901 on May 12, 2020
Gay Male

I'll just start by saying that I've never attended any sauna that may get mentioned in the story. No names that are mentioned are real people either. It's something I've purely put together based on fantasy alone. Thanks for reading! Today was finally the day. I'd been waiting months to go and push myself to try the closest sauna to me which was a short tr...

New Neighbor Ch. 01: Steve Pt. 01

by rimaday on Nov 18, 2019
Gay Male

My name is Steven Vincent wife and I had been married for eight years and lived in a newer middle-class housing development outside of Dallas when this story began. We were one of the original units in the development that now had over 150 houses with plans to double that in the next eight to ten years. We had lived next door to an older couple that retired...

Polishing the Melanated Phallus

by TuxedoPirate on Sep 23, 2019
Gay Male

His huge, black cock was bigger than my face. It was about 11 inches long and 7 inches thick. It was going to be difficult just to get in my mouth but Daddy (as he liked to be called) was expecting me to take it all the way. My lips were going to have to go to the base before he'd pay me that extra $5,000. No help. No woman had ever managed to deepthroat his...

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...

Feminized by My Father

by YANKEE DAN on Aug 30, 2017
Gay Male

I opened my eyes, blinked, yawned, closed them again. I felt confused, disoriented in a way that was... strange. It wasn't like waking up was supposed to be, I wasn't half asleep. I can't remember getting in the bed, in fact I can't remember the last thing I remember. Where did consciousness end last? I was clueless. I tired to move my body and I found it...

My Online Dom Daddy

by DixeenormousToo on Jun 5, 2018
Gay Male

I'm a curious cocksucker and I dream about sucking dick way more than I ever actually do it. I'm divorced (from a women) in my mid forties with a good job and two kids in college. That's why I'm deeply hidden in the closet and very skittish about letting the cocksucker in me out. But the longer I go between sessions and the more big dicks I goon over on the...