Gay Sissy Bet Stories

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Stick Shift: C.S.P.

by zackjack on Sep 14, 2017
Gay Male

I watched, rigid dick in hand, as the smaller man squatted in front of the handsome stud who hit the vape cig between his fingers in obvious expectancy of some good head. Both men's ebony skin aided their blending into the shadows which added to the mystique of my visual. The diminutive dicksucker knew his way around dicks in general and this 'cocksucker pa...

"You Go First" (Ch. 10)

by donaldelliott11 on Mar 2, 2020
Gay Male

This is the 10th in a series. "Samantha" was the 3rd chapter and "Donnie" was the 4th. I regret that my inconsistent use of titles prevents Lit from properly displaying the series. [Writers love feedback. Please comment on and rate this story. About 99 readers out of 100 do *NOT* bother to do either. Comments help authors improve their writing; star rating...

Crossdresser's Unexpected First Time

by kprice1984 on Nov 27, 2017
Gay Male

Just want to say firstly, that this story is 100% true. Secondly, it was much better in person. I'm just getting around to writing it after several years. ***** I'm a 20 year old guy, very good looking, easy to get girls. Brown hair, green eyes and a sexual appetite that's hardly ever satisfied. I had always had a craving or tendencies towards being a lit...

Bitch Dick Twitch

by cockmachine on Aug 18, 2017
Gay Male

First duty of the day. I slide my shaved-smooth body nimbly from the sheets and tip toe into the bathroom. I quickly take care of any errant stubble and look myself up and down in the mirror. I am 19, skinny, about 5'10" with short brown hair and blue eyes. Aside from the slightly-too small lace thong I am wearing, I am nude. That is, if you don't include a...

The Backpacking Trip Ch. 01

by lockedinsteel on Nov 21, 2017
Gay Male

"It's what I want for you baby," said Jamie. Her husband, Daniel, was still a little uneasy with the idea. "I know you've wanted to explore that for years and I think that if you get the opportunity you should. In fact, I'm giving you an order. Do it if you get the chance. Promise me!" she told him. "Okay, Okay I get it. I promise, my love," he replied....

I Turned Myself Out Ch. 03

by drmweaver705 on Aug 24, 2020
Gay Male

"Warning: this video is designed to turn straight men into gay bottoms. Don't say you haven't been warned..." The female narrator had a breathy, clear, commanding voice. It was a voice to be obeyed. "You've stripped yourself naked and stretched your ass in preparation for the arrival of your first ever top..." In fact, I was naked, lying in the marital b...

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...

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...

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...

Off the Grid

by puzziboi on Jan 22, 2020
Gay Male

There sat a cabin. Small. Sturdy. Well-built. A short hike off the Appalachian Trail. Just two-and-a-half miles from the nearest town. The owner was a man in his mid-fifties with gray-green eyes, a dusting of frosty hair on his head, and a full, untamed white beard that covered much of face and came down to his upper chest. The man had two dogs - both mutts....