Jockstrap Stories

352 results
Orientation
Length
Source
Infinite Scroll

Joining a Fraternity Ch. 03

by realpussyboy on Sep 19, 2017
Transsexuals & Crossdressers

This story probably won't make much sense unless you've read the first two in this series. Enjoy! ***** After Dave told me that he also wanted me to ask "the girl" to have anonymous sex with him, I spent some time thinking about how to pull this off and did a little research. As a result, I had come up with what I thought was the perfect plan. Basically, I...

Now I Know I Am Gay

by bigdog500 on Sep 1, 2017
Group Sex

It was a warm and sunny Saturday in July so I followed my usual routine. I showered and shaved and after surfing the porn sites, I had some lunch then put on my swimming trunks and sunglasses and headed to the apartment complex pool. Every time I walk through the pool area I am conscious of the looks the girls give me. Or to be more precise: the non-looks....

Joyce's Sexual Reawakening Ch. 02

by Quietoldie on May 29, 2018
Exhibitionist & Voyeur

This story is not all my own work. Joyce (not her real name) who I met online has contributed ideas and words and made this entire story different from others I've written. I owe her a lot. ***** The next morning Joyce can't wait to discuss what happened in the pub and what was said. They're having breakfast in the conservatory. "There were other blokes a...

A Day in the Life: Penis Penisovich

by yowser on Sep 16, 2017
Humor & Satire

With apologies to Alexander Solzhenitsyn... I woke up hard again that morning, as usual. It was the early aughts, maybe 2001, so I was a bit younger and more vigorous then. I belong, or at least am attached to, Richard, or 'the Yutz' as I half-affectionately call him. We're Russian Jews originally, now living on the outskirts of London, and his given name...

Touch Class Ch. 12

by Uzi_Johnson on Sep 16, 2017
Group Sex

That evening I rang Jennifer's doorbell right at 8. She opened the door, all smiles, and what a vision she was. She was barefoot, had a thong "covering" her below the waist, and her tank top showed generous cleavage. She had her long dirty blonde hair in a ponytail and had put on makeup, including eyeshadow and tan glossy lipstick, and was wearing hoop earri...

Chewing the Fat

by EgmontGrigor2018 on Jun 5, 2018
Humor & Satire

Gregory Black, ditched by the second female in 27-days, arrived at the bus stop to catch the 7:50 into the city. For the third day running a female in the same soft fleece hat and thick military-style coat and scarf was already in the skinny shelter. Noting that this time they were alone, he said cheerfully, "Morning." She eyed him and looked away without...

Canadian Doubles

by Gaius8666 on Sep 14, 2017
Exhibitionist & Voyeur

Bill was a star. All through high school he had constantly won every tennis match he had ever played, and when he received a full scholarship to UCLA to play on the tennis team he couldn't have been more pleased. His talent however somewhat warped his personality and he was thoughtless, arrogant and rude. Despite these qualities his rugged athletic good look...

The Pledge Mistress Ch. 24

by caligula97236 on Sep 14, 2017
Novels and Novellas

Chapter 24 -- Pledge Ken's illusion Once he was cleaned up, Ken knelt in the pledge room to await further orders. Bernadette went upstairs to fetch Lisa, figuring that probably she would want to go next. However, given that it already was close to 10:00 p.m. Lisa decided that it was time to put Ken to bed and enjoy a good night's sleep in the guest room. As...

Park Stud

by Maximilianorubin on Sep 19, 2017
Loving Wives

My wife and I were walking in the neighborhood park when we heard a woman moan. The sound seemed to come from an enormous juniper hedge just off the path. We had both heard the rumors of muggings and even rapes that had supposedly taken place in the park, so we were concerned. My wife went off the path towards the hedge. I followed. It took us some time to f...

Dirty Weekend with Photos

by Rassendyll on Sep 2, 2017
Erotic Couplings

This story is founded on fact and I can strongly recommend the Swan at Southwold. Comments gratefully received as usual and if anyone wants further news of me and Pushpam and an invitation to the wedding just feedback as usual. Pushpam was a fairly new recruit at work and really gorgeous. Indian with soft brown skin. A lovely face, and long legs that would...