Sports Bra Stories

151,048 results
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Serena vs. The Shrink

by DickThePimp on Jun 26, 2018
Celebrities & Fan Fiction

THIS IS A FANTASY...IT IS NOT REAL...IT IS A SEX PARODY This is a story about tennis mega star Serena Williams and Dr Dick (Me) the sports psychologist. I hope you enjoy it. *** I was in my office awaiting my next appointment. I was looking through a questionnaire I had her fill out prior to the appointment. I am a sports psychologist, and I have treated,...

Wild Ride in Elevator

by neonkitty on Jun 5, 2018
Erotic Couplings

Sean was a fan of sports, he loved, baseball, gold, and tennis, mainly because he excelled in all three. He was tall, brunette, with dark eyes, he loved sports sure, but he also loved playing other games, erotic ones. He usually played against Carla, not the erotic games, but the regular sports games, she was a perky blonde, her breasts were huge, he dreamed...

Gym Bunny

by Maverick3254 on Sep 1, 2017
Erotic Couplings

This was absolutely ridiculous. What the hell was I even doing here? For the life of me, I couldn't figure out how I had gotten talked into this shift. I was all set to have my weekend start early, but instead I had agreed, like the nice guy I am, to swap shifts with my friend so he could go out on a date. So while he was having a great time downtown, I was...

Amazing Amy

by lifesabeach84 on Sep 16, 2017
First Time

A few years ago, while I was still in college, I also worked part time to help my parents with bills like my rent and tuition. Most of my jobs revolved around sports at the school, as I was a volunteer for the school's basketball team in which I would help handicap individuals during home games. I also worked in the intramural sports department, being a refe...

Finding the Perfect Fit Pt. 02

by Joshana on Sep 24, 2019
Transgender & Crossdressers

This story is a slow burn serial that is updated weekly. Jamie is a withdrawn college boy with a secret under his shirt while Gen gives no fucks except about Jamie, who she met at a terrible college party with shitty music and bad beer. You know the kind. ***** God, I hate being the stereotype of 'girl who's bad at math' but geometry just breaks my brain....

The Hard Body's Continuing Education Ch. 06b

by dlsloan on Sep 18, 2017
Exhibitionist & Voyeur

The next morning, Cori woke up with the taste of semen still fresh on her tongue. She rolled over and felt Harris next to her. They were both naked under the sheets. She looked at the clock -- it was only 6 a.m., but she was too excited about her new job to sleep any longer. She wondered if Harris would want a blowjob to start his day or if he would be mad i...

Sexually Free Sarah Spain

by DickThePimp on Mar 11, 2019
Celebrities & Fan Fiction

Sex Slut Sex Parody I've been married to former ESPN hottie Sarah Spain for a year. As a matter of fact, today is our anniversary. We are gonna celebrate big time tonight. I hired her away from ESPN to work for me at my website. It's a very successful... and profitable... sports website with a catch. You see we specialize in sex and sports. We combine hot c...

Portal Bra Ch. 01

by qexiqex on Sep 28, 2020
Fetish

Helen browsed the lines of lingerie displayed in the shop. She had been so upbeat about fixing her silly problem that the thought she could fail so spectacularly at such an early stage didn't even occur to her. As if her training schedule wasn't already challenging enough! Her first tries at running had been a hilarious if not humiliating event. Her 'stuff'...

The Sleaze King Ch. 01

by DickThePimp on Dec 2, 2019
Celebrities & Fan Fiction

Having a nice time on my flight home from Georgia. Making out with an old friend and fuck buddy Paula Deen while everybody watches. I love being watched. First class is about half full, so a bunch of prying eyes watching Paula jerk my seven inches while we tongue fuck, and while I molest her old titties through her white blouse. I unbutton it most of the way...

Discovered At the Gym Ch. 01

by richysissy34 on Sep 13, 2017
Transsexuals & Crossdressers

A quick backstory, I am an 21 year old college kid, about 5 foot 6, who just recently joined a gym to try and overcome my smaller frame and slim feminine body. I have a secret love for wearing women's clothes, especially lingerie under my male clothes as much as possible. I have no issues with getting women, the occasional hook up and girlfriend from time to...