Sissy Boy Stories

107,893 results
Orientation
Length
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Infinite Scroll

The Ventriloquist

by justincbenedict on Sep 16, 2017
Humor & Satire

THE VENTRILOQUIST (Or, "Which one's the Dummy?") Okay, like, I don't know why it happened, but it was fuckin' weird, man. I was sitting in the lounge of Texas Tommy's Boi-Toi Ranch, when they got an outcall for a "Big strong, hustler". As Mickie at the desk said, they wanted the biggest boy there, ALL OVER. Next to "Detroit Half-Smoke" Willard, who's...

The Trip Ch. 02

by luv2eat on Sep 17, 2017
Loving Wives

Steve got up and moved toward the back of the boat. I yelled to Steve, "Hey" to get his attention and started to use his expended cum as a body lotion on my boobs and hard nipples. I stared at his crotch to see that he was still semi-hard and watching me, I thought I notice a little twitch. In my mind I said, "Yep, I am gonna keep teasing Big Boy for awhile....

Almost Caught

by sexxobject on Sep 14, 2017
Anal

A boy named Bubba took my anal cherry. I had met him at a church youth group. My parents made me go. I was also going out with another boy at the time. Bubba and I had been flirting, but the other guy beat him to the punch and asked me out first. Since Bubba had only been interested in going out with me as a means to get in my pants, the other guy loved me...

Opportunities

by Talon65 on Feb 7, 2019
MILF

Sebastian was a 20-year-old boy who commonly spent most of his days alone. He didn't have many friends, if any, and he preferred to spend his days alone and quietly. It was usually part of his live routine to go check he's aunt's house, which gave him some bills to see that the property was intact since she did not live there but with her partner at the othe...

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The Driver

by Jaquxz on Feb 11, 2019
Erotic Couplings

I had been downtown with old friends, not that we still get sloppy drunk, but it's just smart to get someone else to drive. Me and my two friends ready to get home. The car pulled up. We had taken a couple of rides, around town. It had been a fun day. I figured it was my turn to sit up front. It seems the universe had saved the best for last. She was beaut...

Lily's Lock

by Herslave on Apr 6, 2017
Fetish

You’ve been attending university for a month, and have gotten well into the swing of things. You study hard and do decently well.What's next? Boy Girl What's next? Boy Girl...

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Diary of a BBW Ch. 02

by bellacbritt on Sep 16, 2017
Interracial Love

Sept 23rd – Wed 8pm: Hello diary I am still messed up from last night. I need some weed. Guess what "Mr. Sex Addict" called. I didn't expect him to call this soon. It seems like I got him real good. I told him he was a porn star. He told me he liked my emerald green eyes and short blonde hair. He knows how to say things that make a woman feel good. Oh so s...

Katie - The Trainee Pt. 03

by Lee0712 on Sep 18, 2017
Exhibitionist & Voyeur

At 07:45 Katie stepped out of her apartment and on to the sidewalk. No more than 2 minutes after Katie had left the apartment her two friends returned laughing and giggling and clutching some clothes for her to wear on her first day to work. They hadn't realised what a state of panic she would have worked herself in to over the blouse and skirt and they cer...

An Orgy From My Girlfriend Ch. 02

by extasybliss on Sep 19, 2017
Group Sex

Recap: My girlfriend and I had always been open to experimenting sexually, and we were very open with one another about our fantasies. Over the past few years, I had developed a cum eating fetish that my girlfriend was all too happy to share with me. When the day of my 24th birthday began approaching, my girlfriend Krista began to tease me with what she was...

Wild Waterpark Fieldtrip

by BetweenDuskandDawn on Sep 12, 2017
First Time

*All characters are fictional and over the age of 18. The young brunette teacher stepped up and boarded the bus. "One, two three..." she said, counting the students' heads poking above the seats. "...eight and nine. Okay, it looks like everyone is here. Are you guys ready for the waterpark?!" Ms. Centino excitedly called out. "Hell yeah!" Danny, one of...