Gay Pillow Humping Stories

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A Helping Hand

by Starsmore on Sep 14, 2017
Gay Male

I woke up by Jay shaking me awake. He always did that, the jerk… It wasn’t because I made weird noises or because he needed something. He just wanted me to wake up at a certain hour every freakin’ morning and I could never understand why. “Get up man! It’s almost 8.30! Shower time!” I growled and heaved myself out of bed. Ever since the fire in Jay’s apart...

Caught with a Wedgie

by marriedhubbi on Oct 8, 2019
Gay Male

I never knew that my straight-laced life could take such a turn. Until that day I thought my hidden life of masturbation would remain undiscovered forever. You see, I have an unusual way of masturbating. When my wife and kids are out of the house, I often head to the bedroom and strip to my underwear. I prop up a couple of pillows in the middle of the bed,...

Darien Ch. 3

by SonOfAGun on Sep 14, 2017
Gay Male

Kitzbühel, Austria. I don't remember a winter as cold as this one since I went to kindergarten. Anyway, Matt and I saved up a bit of money (actually quite a bit) and went to winter holiday here in Austria. Should I introduce myself? Well, if you haven't read about my last adventures, let me update you. I'm Darien, just turned 22 last month, 6'5'', 205 lbs,...

I Hate My Master Ch. 19

by maxpotter on Sep 23, 2019
Gay Male

The guy Chris took to bed after the party was named Tyler. I had to serve them breakfast in bed, and they stayed fucking around, fortunately without me. They headed out to lunch leaving me to my chores. My shock collar was back on, and I got a Dial-A-Fag call from Travis who wanted a fuck then sent me to clean his apartment. I got a text from Josh as I was a...

Bitch Dick Twitch

by cockmachine on Aug 18, 2017
Gay Male

First duty of the day. I slide my shaved-smooth body nimbly from the sheets and tip toe into the bathroom. I quickly take care of any errant stubble and look myself up and down in the mirror. I am 19, skinny, about 5'10" with short brown hair and blue eyes. Aside from the slightly-too small lace thong I am wearing, I am nude. That is, if you don't include a...

Zara's Closet

by Jamie_in_dresses on Jul 4, 2018
Gay Male

Editor's note: this story contains scenes of incest or incest content. ***** Our family took a vacation in Paris a few years ago, well my Dad had to work, but My mom, older brother and I went along for the ride. I was 18, just out of school, My big brother, Gavin, had graduated a couple of years ahead of me. We stayed in an apartment owned by Zara, a femal...

My Secret Dreams Come True Ch. 10

by southernboy81581 on Sep 19, 2017
Gay Male

I woke up about 9 o’clock the next morning. My brother was sleeping peacefully on the floor. I crawled over to the window and looked out. Will’s car was in the driveway. My stomach began to churn and my heart pounded. I crawled out of bed and went to the bathroom. My face still hurt and I had a black eye. I washed up a little and made my way down to the ki...

A Poker Night

by LetsHaveFun on Sep 14, 2017
Gay Male

It was our Friday poker night and we’d been playing for about 3 hours. Tonight we all seemed to be getting bored with the same old thing. When everybody got up from the table for a stretch, Mark jokingly suggested that we should play strip poker. "Sure," said Tom, even though there were only guys in the house. "You’re kidding," I said. "What, you got somet...

Home From College

by BaraKing on Sep 25, 2017
Gay Male

For as long as I can remember, I've always had a crush on my dad. My parents divorced when I was young, and I grew up with my dad so it was just the two of us living together. I often found myself fantasizing about him when masturbating. It never really bothered me that I clearly desired my dad's body, though I kept my desires secret for obvious reasons. He...

Another Beach, Another Stranger

by bybiguy on Aug 18, 2017
Gay Male

I was staying in a condo, sharing it with a co-worker during the summer of 1996. He had gone golfing and I wanted to work on my tan. I had brought various bathing suits with me, including several thongs. Thongs, especially on males, were not worn on the main beach, so I put on a gray thong and pulled on a pair of shorts over them. Taking my beach towel and a...