Prostate Exam Gay Stories

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Infinite Scroll

Ms. Jones's Revenge! Ch. 03

by DoesIsCanCant on Aug 21, 2019
Anal

"So, who's this guy coming over today?" Ms. Evans asked. "His name is Joel. He and my son used to go to school together. He's in need of some extra money, so I asked him to come by and help with your garden today," Ms. Jones asked. "That's not all, from what my son said, he's supposed to be a massive pervert who's never gotten laid." "I see now. So you wan...

Role Playing with Michelle Ch. 04

by gunhilltrain on Oct 15, 2018
Erotic Couplings

The stories in this series were written at least a year ago before I knew about Literotica. The previous one (chapter 3) is posted here. If the object of the New York authorities were to increase prostitution and depravity, they could not better accomplish it than by their present policy towards the unfortunate class that everybody endeavors to ignore, but...

Three Holes in One

by rwcforfun on Jul 10, 2019
Mature

(All persons depicted in this story are over 18 years of age. Any similarities to real life are purely coincidental) *** Having just missed qualifying for the 2019, California Men's Amateur Golf Championship, I knew that this summer, the summer before my senior year at San Diego State, would be critical in my development as a golfer. It would be ideal if I...

San Angelo

by GuessImJamie on Jun 25, 2019
Group Sex

All characters depicted in this fanciful tale are over twenty-five years of age. *** I am well aware that I am no Tom Cruise. I don't have his looks, although I am taller. I don't have anywhere near his money, although I have suddenly come into a huge fortune by my own standards. In my nearly forty years as an attorney I have not earned the thirty or so mi...

Tara and the Presidents Ch. 02

by rikimaru4 on May 27, 2019
Transgender & Crossdressers

Tara awoke in her own bed with no recollection of how she'd gotten there, sitting up blearily and trying to recall what had happened. She automatically reached over to the nightstand for her glasses, not finding them before suddenly realizing she didn't even need them -- her vision was crystal clear. In fact, it was sharper than she could ever recall. This t...

My First Time with Alexa

by Notsosleeper on Jan 29, 2019
First Time

To start off, this is not something that happened recently. To be honest it was around 5 years ago, so the details of two different encounters might be mixed up a bit. Her name was Alexa, her long slender body rounded off with perfect light brown skin and dark brown eyes that will get you from 0-100 in milliseconds. We had met through a mutual friend at wor...

My Neighbor Ch. 02

by jeffss45 on Dec 2, 2019
Fetish

I wake up hard and excited about meeting Peggy. I resist the urge to masturbate, I want to be horny when I meet her later. I still can't believe how lucky I am to find a woman so into teasing. I make it through the day and head to the hospital a bit early. I get there 30 minutes early so I sit impatiently in the cafeteria sipping on some coffee. Finally, i...

The Path Not Taken

by Chastebob on Jan 20, 2020
Erotic Couplings

Like some of the other stories, this is part true and part fiction, though this one is mostly fiction as the title might imply. If you want to psychoanalyze my work, call this one an attempt to imagine the alternate world I would have been in had it happened this way. The summer between my Sophomore and Junior years in college I met a fascinating woman, Sha...

Notty High - For Naughty Teens Ch. 04

by sthsth on Jun 1, 2020
Exhibitionist & Voyeur

(Thanks to Drewau for editing. Comments and feedback are always welcome and appreciated. All characters are 18+) After the amazing day that I had yesterday, I couldn't help but dream about everything that happened. I especially savored losing my virginity to Harley. My dreams were pretty much a playback of the day's events. First there was the blowjob by Hi...

Hired Gun Pt. 05

by HughMansardum on Mar 9, 2020
NonHuman

Just as Suzy promised, Troy was back on his feet the next day. The human spent the craziest night of his life strapped to the medical exam table, making love to his tigress captain, female skunk archaeologist, his doctor-vixen, and his domineering engineer, a rambunctious rabbit. The events of the prior night stuck with the human as he tried to fulfil his du...