Gay Prostate Milking Stories

5,088 results
Orientation
Length
Source
Infinite Scroll

Thirsty Old Men Ch. 02

by TheReluctantKnight on Sep 14, 2017
Gay Male

A word to the wise: This is a work of complete fiction. Never happened in real life. I don't condone rape. This is a fantasy about a young (straight) man who is pleasured against his will. If you have a problem with this (in fantasy as well as in real life) then I suggest you stop reading here and now. Please know that emails sent about the content of t...

Getting . . . Educated Ch. 10

by sr71plt on Sep 14, 2017
Gay Male

I had hoped after my conference with Coach Seeman where he had commiserated with me about how badly one of his wrestlers had used me outside the gym that I would get some relief from the liberties he was permitting his guys to take with me, but no such luck. At least, though, my next team punch event day at wrestling practice was more memorable for being the...

This Thing Called Life Ch. 08

by noodneighbor on Sep 14, 2017
Gay Male

I was cleaning myself up in the sex store bathroom, happy that I had gotten 'Eager' hooked up with his roommate and was also pleased that Tree would see I could earn my keep at the hotel. My ten inch cock throbbed as I washed it off, still somewhat hard, likely due to the Viagra, even though I had just fucked and then shot my load onto 'Eager's, well, eager...

The Ride of a Lifetime

by jasedean on Aug 18, 2017
Gay Male

It was the day after my 21st birthday, I was finally old enough to drink! It was early in the evening, so I decided to walk down a few blocks to a neighborhood bar. It was pretty quiet inside as I sat and ordered a beer. An older man was sitting just down from me, and I noticed he was eyeing me. He wasn't in bad shape, probably in his late 40's with a goatee...

Cum Over

by sickoboy on Oct 22, 2019
Gay Male

Damian walked out into the sunlight and immediately felt the humidity in the air. The contrast from air conditioning to summer afternoon was like a rolling oven blast. Damian had thrown on a cotton Hawaiian shirt, and a pair of jean shorts, frayed at the cut offs. On his plump feet, he wore a pair of sandals. Today Damian was going commando. As the heat boun...

MTMF League Ch. 01: Connor vs. Johnny

by the1deros on Jan 16, 2019
Gay Male

Connor has been fucking the newcomer back and forth for almost one hour now. He has turned the poor boy in his whining bitch. Connor would have some mercy on the younger man if the freshman wasn't a cocky bastard that thought he had a chance against him. Connor not only is a bigger and stronger specimen of pure toned muscles, he also has 2 years of experienc...

Married Straight Guy Risks It

by Dracthyus on Aug 30, 2017
Gay Male

I knew this was the only way I could go through with it. As I stepped into the unlocked hotel room, I could still feel the shudders of fear, and excitement, race through my body. The hotel room was empty, just the way He said it would be. I closed the door, and fought the urge to lock it. That was harder than I thought… one flick of that little knob, and no...

Shunga Silence

by sr71plt on Aug 18, 2017
Gay Male

"We will have the silence of Shunga." It was the first thing I'd heard the film director we were trying to land speak during the first production meeting on the movie Winter in Niseko. Knut Johansen was the reason we were freezing our tails off here in Oslo, Norway, in the winter. Atmospherics. Johansen was all about atmospherics. We could just as well have...

It's Perfectly Normal

by NickyNoxville on Apr 21, 2020
Gay Male

All my stories take place in a parallel world, very similar to our own, where STI's do not exist, so my stories are filled with practices that are highly unsafe in this world. I'm not going to say don't try this at home, but take care of yourself. All my characters are of legal age, and you should be, too—do not read my stories if you are under the legal ag...

Trail "Doctor"

by sr71plt on Sep 1, 2017
Gay Male

I had never tried to seduce another guy before, but Dale was just there at the right time and place. We were both runners—he because he was on the college football team and running up and down the Pine Mountain trail helped keep him in shape and I because I wasn't that long out of college myself and I was doing the best I could to keep my fine form in shape....