Gay Prostate Milking Stories

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Extra Credit

by agpatch2 on Aug 18, 2017
Gay Male

So one day I'm just sitting in my apartment, bored and horny, reading some online personals. Most of them are totally pathetic and I'm having a hard time even maintaining an erection. I never really answer personals but sometimes they get me pretty excited and I end up with a damn good orgasm. On this particular day, however, they weren't even getting me har...

Hungover and Horny

by Patrick2380 on Aug 18, 2017
Gay Male

Damn, we drank so much last night! I figured we would. We always did when we got together to play games. We had a "reunion night." My old roommate and his brother, our friends Bess and Heidi, and our friend Rick. When we first were out of college, we drank like this a couple times a week. Watching TV, playing drinking Jenga and various card games while pound...

High School Confession

by Roulequin on Aug 18, 2017
Gay Male

In the year that I had just turned 18, I had come to high school a religious zealot, heavy with the residual dogma of my former private Christian school's teachings. The world outside those modest (but not so humble) walls was a heathen, blasphemous devil's playground full of sinners who lived in unholy ignorance. I was disposed of the school a warrior in th...

Seduced by a Friend

by yorie on Sep 14, 2017
Gay Male

This is my account of my first sexual encounter. I was very fully developed with a pedigree at all types of sports and games. I was generally regarded as the local sports hero and I just lived for my next sporting event. I had been through the wet dreams and other nightly emission sequences which were unexpected but had been exciting, and I was dealing with...

Can I Borrow Your Boyfriend?

by knowsbetter on Mar 2, 2020
Gay Male

"Ok, Ok, I got one," Josh said. I was out with my friend Melissa and her new-ish boyfriend Josh, and we were three glasses of prosecco into a late brunch. The waitress was clearly hungover and didn't give a shit, service was winding down, and we were off in a corner gossiping and talking trash. The current topic: terrible first-date icebreaker questions. "B...

On My Knees

by rodneysteele41 on May 22, 2019
Gay Male

There I was, on my knees in the center of a dimly lit living room, naked as a jay bird. Between my thighs, my cock and balls were bound up tight from a latex cock ring. My dick jutted out from my crotch a good five or six inches, excited by the vibrating bullet that the ring had pressed against my scrotum. A long drool of my clear pre-cum steadily leaked fro...

The Island Ch. 05

by JJ122964 on Sep 14, 2017
Gay Male

There was hermit on the island that lived in his cabin on a hill. He to wore the traditional loincloth and enjoyed the island's ministrations. His name is Matt and this morning he was eating his breakfast of cereal and juice, his usual breakfast, outside of his cabin. He did this to enjoy the sunshine and sea breeze that would come up his mountain. He did no...

Getting Caught Cruising Pt. 02

by mrfallenangelxx on Sep 1, 2017
Gay Male

We all just stand there staring at each other, wondering who was going to speak first. This hot stud just stood there eyeing us up and down and then gave a cheeky half smile; I stand there frozen with fear until I look up and see him smiling. I stand there pondering, "Does he want to join?" I turn to Callum to see if he is thinking the same as me. He lo...

Letting Go

by fantac64 on Aug 18, 2017
Gay Male

At 31 I was at the top of my game when all of this took place. I wasn't making a mint but it was steadily getting closer to it so when I won five hundred bucks as "account manager of the year, it was just found money. With not a little bit of influence from my fellow managers, I decided to take three hundred of it to celebrate at Venus, a local gentlemen's...

Michael Wood

by Pissdrinker on Oct 6, 2020
Gay Male

This event took place just before the AIDS crisis and therefore condoms weren't used. ***** I had secured my first supervisory position at a haulage and distribution company and Michael was one of the 11 drivers I had responsibility for. I was 25, he was about 10 years older than myself and about 15 years younger than the rest. He was, I understood, single...