Jockstrap Stories

352 results
Orientation
Length
Source
Infinite Scroll

Joining a Fraternity Ch. 02

by realpussyboy on Sep 19, 2017
Transsexuals & Crossdressers

Thank you to the anonymous reader whose idea I used toward the end of this chapter :) Also, this story won't make much sense if you haven't read Chapter 1 first. ____________________________________ The morning after our encounter, Josh—as usual—got up at the crack of dawn for rowing practice. When he put on his jockstrap, his cock was even closer to my...

How Far Would He Go

by stories55 on Dec 29, 2017
BDSM

This story was inspired by a Domme that wanted me to write a story about being with a man. It was at first just a few paragraphs. She then wanted more and suggested I add various elements. She knew it embarrassed the hell out of me to write it. But then she knew how much I was a victim of my own sensuality and more would follow. She knew she just need to giv...

"Santa's Elves Will Do WHAT?" Ch. 02

by ClodiaP on Sep 19, 2017
Novels and Novellas

You realize that soon I'll be telling you only what I HEARD happened to the "elves" on their gigs? Only my own experience is first-hand; actually, I considered telling only my story, and, you know, maybe I will. It has GOT to be the most extreme. It may be a warning to bright, idiotically naïve high-school girls about playing elves from Camel Toe Village and...

Adventures of Carl Ch. 01

by iamcontent on Sep 16, 2017
Interracial Love

Carl is a 52 year old black male. He is 5'8 and 155 lbs. He is physically fit runs every day and goes to the gym for at least hour and a half a day. He is also a widow. He married his grade school sweetheart Dawn, and she passed away from cancer. They never had any children, but each had brothers and sisters and viewed their nephews and nieces as their own,...

Our Sexy Adventure Ch. 04

by hornycarol on Sep 23, 2019
Loving Wives

Carol, John and I had been together for almost a year. You would have thought that the fierce tempo of our sex lives would have cooled down, but it hadn't. We continued to fuck, suck and grope several times a day. We felt lucky to be in the loving situation we found ourselves in. Work kept us busy and we evolved into an accepted family unit. We discussed ta...

Problem Student Ch. 02

by spamwich on Sep 19, 2017
First Time

The following day, James came to Mrs. Myers' office a few minutes early, like she had instructed. He looked a little nervous, but there was no sign of the near-panic from the day before. The teacher gave him a warm smile, which he returned. She really was quite beautiful. "Hello James." she said "I think I've got you covered." wincing at the unintended pun....

Doin' Bruins Ch. 01

by brolston12 on Sep 17, 2017
Celebrities & Fan Fiction

It was my first ever Boston Bruins practice. I’d won a contest to attend a closed skate, so it was just me and the boys. I watched longingly as they skated one by one onto the ice. I especially kept my eye on Bryan Berard (#34) and Brian Rolston (#12). The two hotties. I thought slutty thoughts as I watched each take a turn shooting the puck at goaltender S...

Word Choice

by evelyn_carroll on Sep 17, 2017
How To

Wyo_girl has written a fine and very useful article on the choice of words in erotic description. It was so good that I felt moved to reply and add a few thoughts. Also, she misses a couple of important points and I wanted to suggest a few more "thesaurus" entries from my own repertoire – for the use and convenience of the young, as Oscar Wilde might have pu...

Taking Turns

by simplyme on Sep 16, 2017
Anal

This is just a work of fiction, hope you enjoy. My girlfriend and I have an agreement: we trade off or rather, take turns. What that means is that each Monday I roll a die to see how many days she gets to use a strap-on on me. Sometimes it's an entire week sometimes it's 1 day, whichever it is we go by it. This morning I rolled a 3. So for the next 3 days s...

Sissy BBC Cleaner Pt. 01

by SmegmaSissy on Sep 16, 2017
Transsexuals & Crossdressers

I got all dressed up. Put on my tight black one piece with a snap up crotch, a tiny transparent black skirt, a black g-string, thigh-high fishnets, six inch black open-toed heels, my black leather choker, big hoop earrings, blue eye-shadow with dark red lipstick to match my finger and toenail polish, and a large black plug. I'm five-eight, one hundred and fo...