Jockstrap Stories

352 results
Orientation
Length
Source
Infinite Scroll

Jim Goes to Boot Camp

by JimmyJohnson on Sep 12, 2017
Exhibitionist & Voyeur

This story is a work of fiction. It's about an 18 year old boy named Jim (my alter ego) who gets himself in a bit of trouble and ends up in a juvenile boot camp. The story describes Jim's entrance physical exam as it is given by a female doctor and nurse. Please let me know what you think. ------------------------------------------ Jim was silent as he w...

Silver Fox & Barely Legal Twink

by puzziboi on Mar 30, 2020
Transgender & Crossdressers

Jim O'Connor was straight as a board. The 60 year-old with the crew cut white hair and stubbly face voted Republican, owned several guns, drove a Dodge Ram pickup, and was a retired high school teacher & baseball coach. In fact, the married father of two adult daughters with four grandkids had amassed 19 consecutive winning seasons as head coach. His record...

Coach Turns Bi

by Coxswain on Sep 12, 2017
Loving Wives

New PE teacher and his wife seduced by well-hung student I made it! I made it across that stage wearing the Cap & Gown! Plowed through the long years of college and graduated! Yes! High-five! Thanks to Uncle Sam and the GI Bill, I had a diploma! Eleanor and I were in the Army in tough times, and when I hit 20 years in 1965, we decided to retire. As a drill...

Neighbours Fun Pt. 02

by konradj on Nov 22, 2017
First Time

I'm sitting in the car. Ray is driving. He's talking to me but it's not sinking in. He's saying words but I don't know what he is saying. My brain is focusing on what I have just seen. I simply can't stop thinking about seeing Jemma's bum and her hairy mound which had just been sprayed with Ray's thick cream. I'm wondering what Jemma is doing right now. I kn...

Work Place Crush

by heney1282 on Apr 7, 2021
Cheating Spouses

You go to visit Lauren at work, and when you get there you notice her flirting with a male coworker. As you walk up, she sees you and quickly changes her tone with him. The silly smile drops from her face and she asks him if he can check back with her after lunch. You two leave and go to a nearby diner. While you are eating you ask her "So who was that...

Open in Reader

Our Sexy Adventure Ch. 05

by hornycarol on Sep 24, 2019
Loving Wives

The three of us woke up as the sun set over the ocean. We were all groggy, sweaty and slippery with suntan lotion. Carol looked over at the sliding glass doors and said, "Anyone could have watched us." John and I smiled. I was pretty sure I had seen some of the staff watching us. The bathroom had a large glass enclosed shower. It easily fit the three of us....

Bonnie Blows – Lesson 1

by almostincognito on Jul 14, 2020
Loving Wives

A Wickett Adventure *** Having two women suck your cock is a pretty common fantasy for men. Ryan Wickett could be counted among those who share that dream. He could also be counted among the smaller number of those who are lucky enough to experience it, AND among the MUCH smaller number of those whose cocks are used for a very special purpose: blowjob prac...

Switching Slut Ch. 09

by P_E_C on Sep 25, 2017
BDSM

Chapter 9: Tanya in Control Sunday afternoon, Kari had gone to her job, and Lynn was relaxing around the house. She tended to some chores, and then sat down to check her email. There was a message from Tanya. She opened it and read: "Auntie said I could mail you and tell you about our adventures yesterday. It started when we paid a visit to a friend of Aun...

Naïve Couple Meet Woodsman Ch. 01

by weddinghelper on Sep 14, 2017
Loving Wives

My spouse and I have been together for over 10 years and had our first child at a very young age. We are well-established professionals who like to enjoy activities such as trying new restaurants, going to shows etc. In spite of her past pregnancy she was still able to maintain her beautiful face, but has gained in breast size; 34 DD firm and big. She also g...

Dad or Mom? Ch. 03

by missassam on Sep 25, 2017
Exhibitionist & Voyeur

Here before you is the latest episode, the story of Tommy finding his way in 1950s Minnesota. I pay tribute to my mentor and inspiration, the contributor to these pages known as Aaron Burr. Fans of his work will find references to his story Veronica Peeps. Our characters, waiting in the wings, are 18 or over, dirty minded and sex obsessed and very eager to...