Jailbait Stories

288 results
Orientation
Length
Source
Infinite Scroll

Wanted: Dog Walker

by Dr Kink on Sep 13, 2017
Mature

Rick Potter turned into his driveway, shit it was eleven o’clock. He had told Sheila he would be home no later than eight. She was going to be mad, but he was getting use to it. Ever since this new project was given to him, he had not been home before nine O’clock. He had been working on it for two months and it would probably take another two months to fini...

Legally Bound

by Northsider on Sep 17, 2017
BDSM

"Oh, that's OK, don't worry about it, thanks for calling and letting me know. Sure, Tuesday at one fifteen works, I'll see you then. Bye now." "Alright, sweetie, my last appointment just cancelled, time to crack that merlot!" Lena was already one step ahead, as usual. Out behind the salon on the makeshift patio, she already had two glasses poured as she wa...

The Group Ch. 01: The Loft

by DarkDeliciousDebauchery on Nov 4, 2019
Group Sex

This is a long story, foundation for a series titled "The Group." *** I opened my eyes and the sunlight through the window caused me to squint with the sting of a familiar hangover filling my head. As I looked around, I realized I was in a familiar bed. I was in the loft, downtown. I had no idea how I'd gotten there, but I was used to that. As I sat up,...

Subservient One Ch. 04

by spider007 on Sep 19, 2017
Loving Wives

On a later day Ken went with me to grocery shop. He had me wear my "come hither" outfit as he called it: a braless sheer tight blouse with four undone buttons, a tight red leather miniskirt cut to just below my ass cheeks with a black thong, 4-inch heels, and heavy dark red lipstick. He was always having me check prices of bottom shelf items, and, even thoug...

Little Debbie the Girl Scout Leader

by MrJack on Sep 14, 2017
Mature

Readers: I'd like to offer a few words of introductory information. I had intended to write a short tale of 'slam-bam' forbidden 'barely legal' sex. My trouble was; I fell in love with the female character and I couldn't allow her to be 'fucked and forgotten'. So, what I ended up with here is a slow-told sex story which has an element of romantic love mixed...

Sins of Joy Ch. 07

by bena4u on Sep 12, 2017
First Time

My dearest editor "JackGates74". I think it's much better and he deserves the credit. Thank you "JackGates74" for all the hard work on the story. ***** Farida and Farzana were on the pills on a permanent basis to avoid any problem of pregnancy as our sexual relationship never stopped. We took extra care to conceal our secret, but hiding our relationship w...

Keeping It Legal Ch. 01

by AnAmericanDarling on Sep 14, 2017
Mature

*Note to readers: While the main character of Katie is 17 in the first portion of this story, she does not engage in any sexual activity until she is 18. So, with that said, happy reading, God Bless, give my regards to Thelma Lou, and Hakuna matata!* * My mother considered the age to for a girl to become a woman was 13. Well, I was 17, not far from my 18th...

What's in the Big Chocolate Box Ch. 02

by sirhugs on Sep 17, 2017
Loving Wives

This story follows "What's in the Big Chocolate Box? ch 1" but can be read on its own. The couple was introduced in "What's in the Big Box?", but that is a freestanding adventure. Rachlou helped with characterization and plot holes, wicked woman edited. All errors or perversions are mine alone. * Luci had worried her confession might upset me, but of cours...

My Prettiest Whore

by moonfire on Sep 13, 2017
Exhibitionist & Voyeur

Some people hate that word: whore. I think it is beautiful. Look at them, now. They cannot see you. The window is mirrored. I watch it all from here. My girls and their clients. The ancient dance, the men and the women. Always the same, yet always different. Look over there, now, by the bar. See that girl in the silver mini-skirt. Tamsyn. The o...

The DeVilles Ch. 04

by MonikerSmith on Sep 14, 2017
NonHuman

Note: All characters in the following story are 18 years of age or older. Any resemblance to real persons, places, or events is purely coincidental. * Jessi DeVille jiggled onto the floor of the Kit Kat Klub, her large, unfettered tits swaying proudly with every step of her 6inch white stilettos. The flowing silk skirt she wore was little more than a drama...