Jailbait Stories

288 results
Orientation
Length
Source
Infinite Scroll

Great Service at Buy Low

by movie_store_girl on Sep 1, 2017
Group Sex

Alyssa may be in graduate school but she sure doesn't look like it. She is 5'4 150 lbs (curvy in all the right places) with a 38DD chest. She could easily pass for a young 18 even though her ID says 22. She constantly gets questioned about her life and her career aspirations, but she isn't really ready to grow up yet. A lot of the time Alyssa has people as...

Marcy

by SierraSprite on Aug 24, 2020
First Time

Marcy was in my lap and her lips were pressed to mine. My heart was pounding. A girl was kissing me. A wonderful kiss that I didn't ask for. "Marc, you need more practice kissing girls." "Whenever you wish, mistress." Her hand collided with my cheek. "Do not be a wiseass." I knew I was in trouble. The smartest girl in class had decided I was taking her t...

Appeasing the Boss

by JennaMonroe on Jan 22, 2019
Erotic Couplings

Sarah pulled into the makeshift parking lot next to the job site she was working at and sucked in a deep breath. Working Sunday sucked. She was working overtime she definitely needed, but it meant she was working alone with the boss and that she was not looking forward to. She worked in a male dominated field, she was used to crude, she was used to rude, she...

Dunes

by Middleagepoet on Aug 18, 2017
First Time

It almost happened when Michael was seventeen, almost. Of course the four year gap in ages between him and Ellen was huge for them at that age. As a twenty one year old, she, of course, supplied the beer and pretty much ran the show. Michael had been careful with how much he drank, wanting to be sure he remembered everything. Ellen appeared drunk to him, s...

Gabe

by illusory_transitory on Sep 17, 2017
Non-Erotic

Here I was again. Same situation, same problem. Exacerbated by the fact that this time, the difference was around twelve years instead of three. It wasn't that I couldn't be trusted. The problem, at least for me, is that I can. Let me explain. I hadn't had a boyfriend for a while. The last boyfriend I had was actually quite a bit older than me. He'd said...

Stress Relief

by Entrammeleur on Sep 16, 2017
Transsexuals & Crossdressers

This was one of a number of stories I published on anon.penet.fi in the 1990s. I found a trove of them while browsing through some old CD-ROMs, and decided to give them new life on Literotica. *** People deal with stress in many different ways. Some flirt with danger; some find better living through chemicals; some find yet other outlets. My most effective...

Charlie Wilson's Whore

by MawrGorshin on Sep 14, 2017
Celebrities & Fan Fiction

Ever since I watched the movie, 'Charlie Wilson's War', which came out in theaters a few years ago (I now have the DVD, and watch it constantly), I've been fantasizing about Tom Hanks in the title role. He's already my favourite actor, with his good looks and charm, but seeing him portray my former employer from twenty years ago (he died recently, actually)...

One Night in Chloe

by JamesMiehoff on May 7, 2019
Erotic Couplings

Copyright (c) 2019 James Miehoff, All Rights Reserved. This work may not be published whether for fee or free without this copyright. ------------------ This is one of a series of stories set in what I call Universe-J. Universe-J is very much like this universe with a few exceptions. First the people tend to be a little more sexual and less hung up on...

Tempus Fugit Ch. 02

by ReggieWanker on Jan 22, 2018
Sci-Fi & Fantasy

*** I was having a wonderful dream. It was the last trip Aurilaine and I had taken together, camping at the base of the Crystal Cliffs on Ellison's World. The rising temperature of the morning made the cliffs sing. Aurilaine was giving me the blowjob of my life, the rising suns creating a crown of white gold around her pale blonde hair, shimmering as her he...

Friends & More

by justme007 on Sep 2, 2017
Erotic Couplings

Dee was a supervisor in a call center. She hated the long days and the long hours that her job entailed. She just wanted something or someone to come along, and make life a little more worth her while. She would look at the all the young guys that she worked with and would think to herself, "jailbait." Dee was 32, single and hating it. Most of her friends...