Gay Sissy Pet Stories

1,599 results
Orientation
Length
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Infinite Scroll

Transforming Tim

by oskarwild on Sep 25, 2017
Gay Male

The Elevator Rafe could hardly wait for his lunch hour to come. But he wasn't hungry for food. He was hungry for the new elevator boy. The new boy was just the type Rafe lusted after. He was short and slim; probably five-six and maybe a hundred twenty pounds at the most. And he was young. All of the elevator boys the building employed were high school seni...

Discovered by a Black Guy

by chastity_sissy on Sep 14, 2017
Gay Male

I should preface this story by saying I've never identified myself as homosexual, but sometimes after being locked up in chastity for a long time combined with crossdressing, I must admit to some fantasies involving other men. I never expected anything to ever actually happen, and it's my own fault really. I had been paying a beautiful, very sexually fetis...

A Very Big Man!

by keptsissy on Aug 30, 2017
Gay Male

Of the men I see regularly he's the biggest. Not just height and weight, his cock is huge, close to 11". And his cock is thicker than any other man I've ever seen. My ex-boyfriend introduced me to him at a party. He told me to go to the bedroom with him and 'be a good girl'. It was one of 'those' parties, all of us girly girl sissies on full display and on t...

From Alex to Lexi Ch. 03

by oskarwild on Sep 14, 2017
Gay Male

Awakening Lexi lay in bed with the morning sunlight streaming across his naked body. He was in the fetal position and he could see Max, his new Daddy, lying on his back next to him, sound asleep. Daddy's arm was over his head and Lexi could smell the pungent odor of Max's underarm. They had worked up quite a sweat last night before finally falling asleep....

Beauty and the Beast Pt. 02

by Suzzique on Dec 30, 2017
Gay Male

He switched the mobile to speaker phone and I heard a grating northern voice. "So you're enjoying yourself, you dirty little girl. Can't wait for your Daddy's cock. Well, your Uncle Ted is on his way to see you and is bringing another hard cock to service that tight little cunt you keep between those sexy bum cheeks. You're a hot little bitch. I may only ra...

Freddie Pt. 02

by exaucer on Aug 18, 2017
Gay Male

I could not believe it. Freddie must have dissolved the Viagra in the coffee and that was why my cock had become erect on its own, why it would not go down and why I was unable to resist his advances. Freddie had duped me. At least that is what I told myself. I decided to go back down to the basement and confront him. When I went down to the basement I went...

Little Sex Toy Ch. 05

by keptsissy on Sep 26, 2017
Gay Male

I'm squatting in the middle of his cold cement basement floor, just over the drain in his laundry room, sitting back on my high heels. The 4" spike heels he insists I wear now around the house, wobble in them and get whipped for it, walking or squatting. He says a 'lady-like' little bitch should know how to wear high heel shoes. Leather, padded restraints...

Daddy's Girl

by oskarwild on Sep 25, 2017
Gay Male

The Hitchhiker It had been snowing all day. A wet, heavy incessant snow that was covering everything including the highway. Combined with a wind-chill factor in the teens, Christopher was almost frozen stiff. He was elated when the huge semi pulled over to pick him up. He climbed up into the cab and smiled thankfully at the driver. "Thanks a lot mister. 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...

The Poker Master

by MixMasterFlex on May 1, 2018
Gay Male

So I had a friend named Reshawn in college who also had a serious obsession with poker. We played obsessively, convincing our friends to join us for a game in our dorm whenever we could. When we couldn't get a game in person, we would play online, share stories over IM, and sometimes trade money on the various sites. One day Reshawn had asked to play on my...