Jockstrap Stories

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CFNM Randy Summers Jockstrap Maid

by VHarrington on Apr 15, 2020
Exhibitionist & Voyeur

In my never-ending search to make ends meet in this economy, in addition to my party planning, nude bar-tending/waitering gigs, I occasionally grab a housecleaning job. However, total CFNM aficionado and exhibitionist that I am, I never do just normal, run-of-the-mill cleaning! I got a call from a lady in Westwood, who wanted someone to come over and tidy...

Thong Fantasies Ch. 03

by Smooth_Bi_Guy on Sep 19, 2017
Group Sex

I got up off my knees and grabbed a towel to wrap around my waist, as I watched the activity in my hotel room. Eric was cleaning himself up and trying to squeeze his still swollen cock back into his discarded jockstrap and shorts. Gloria had recovered from her recent self-induced orgasm and was rearranging her clothing to cover her modesty. I invited Eric to...

Disciplined by Coach Pt. 01

by Guy521 on Mar 12, 2019
BDSM

Grayson's shiny cock head pulsed as he pumped his slick hand up and down the swollen, veiny shaft. In his other hand he held his best friend's sweaty jockstrap. The jockstrap which had cradled his friend's balls and cock, had gone unwashed all season, the pouch emitting a masculine stench that drove Grayson wild. He was fast approaching climax, pumping more...

The Locker Room

by hydrangealawrence on Sep 23, 2019
Group Sex

I sneak into the locker room to surprise Cooper after the rest of the team leaves. I peek around the corner and spot him changing out of his uniform. He’s naked except for his jockstrap. I take a running leap onto his back. “Congratulations, Mr. Coastal Series Champion!” I wrap my legs around him and pepper the side of his face with kisses. He lowers me to...

Matt Becomes Mattie Ch. 06

by clarepanties on Sep 19, 2017
Transsexuals & Crossdressers

So Joanna's birthday came around. She took the day off, it was a Friday and the second day after Louise and my jaunt in Oxford. I needed my sleep as the hormones were evidently kicking in hard and I had let Jo know about this. Jo was, therefore, the first to wake. I knew that a little submissive pre-session was a good way to start the birthday and so I let...

Becoming a Cum Dump Ch. 08

by plyasian on Sep 14, 2017
BDSM

BEEP! BEEP! I rolled over and pulled out my phone. 6:45am. Tuesday, October 6th. I quickly hopped into the shower where I did a once over of my body. My hair had grown back a little so I quickly shaved it off. When I finished, I headed back to my room to figure what I was going to wear. Shit what do I wear. It was easy when I had Thomas making the decisio...

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...

Donna's Ultra-High Heels Bk. 02 Ch. 15

by SHAFERLINE on Sep 15, 2017
BDSM

Author's Note Chapters 12 through 17 are the final chapters to "Donna's Ultra High Heels - Book 2" and will be sequentially submitted in both the Fetish and BDSM categories in the following order: Chapters 12, 14 and 17 in the Fetish category and chapters 13, 15, and 16 in the BDSM category. ***** Chapter 15 Donna and Ken went directly back to their ro...

Cindy Masters, Dyke Detective Ch. 03

by Trapper_Jock_Mcintyre on Sep 16, 2017
Humor & Satire

This Episode: A Chance Encounter - Part Three Masters is the name. Cindy Masters. I'm a detective. I get $50 a day and expenses, $75 if I can get it. I lay back on the weight bench and placed my feet behind the leg brace for a few chest flies. My eyes darted about the room like a fly looking for a warm beer. Glancing down between my legs, the mound made...

Fun at the Movies

by Queerftmboi on Sep 12, 2017
Transsexuals & Crossdressers

Generally I get off almost every day. I don't like waiting too long because I get grumpy and tense. But, occasionally life gets in the way, or I'll intentionally hold off for a few days so that when I get to have sex I'm extra tight and horny. This was one of those days and he knew it. He had spent all evening teasing me, kissing my neck, letting the little...