Gay Boot Stories

775 results
Orientation
Length
Source
Infinite Scroll

a Home Away from Home

by Whydoyoucare? on Aug 15, 2016
Gay

I stare listlessly through the glass window pane, watching as the trees woosh past in a blur; every now and then i see a stag or doe proudly standing, munching on grass and barely looking at us when we drive past; cars are so common here that the wildlife doesn't have the sense to be afriad. We take a sudden turn onto a dirt path, the car's suspension groans...

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Bitch and Bear: The Beginning

by KendallJames on Aug 18, 2017
Gay Male

Bear was rolling down Rt 2 toward Lincoln when he saw him-- carrying a small backpack, walking tanned and shirtless, in tight jeans and boots. Not hitching, but looking over his shoulder as Bear approached. He pulled to a stop beside him-- tall, long-legged, with a tight ass. "Nice bike." "Wanna ride Bitch?" "I'll ride-- and I love it when you call me Bi...

Twink Troy uses me for fun! Pt. 01

by usemetoday1962 on Mar 18, 2020
Gay Male

So I had not seen Troy for a few months and was being fucked once a week or so by Chris and his girlfriend. She was a real tough girl who got off watching Chris roughly fuck me but she was jealous because my legs were better than hers. Then Troy called me and asked if I wanted to come over and play. He told me he has brought some toys and his friends were no...

Two Masters, Two Slaves

by boyganymede on Aug 18, 2017
Gay Male

Over the past year, my relationship with Steve had evolved into a Master/slave relationship. He had trained me to submit sexually whenever he wanted, wherever he wanted, however he wanted. During a typical evening at home together, I would be nude except for a collar, would open my mouth only when spoken to or to receive his cock, and would fetch his beers w...

The Field Pt. 01

by Tsugaru3000 on Nov 26, 2019
Gay Male

"Be there in 10 minutes." The text said. Damn him. He knows it's a 35 minute walk. And he likes me to be ready and waiting. I took off my pants to remove my underwear and put my pants back on. I made the mistake of wearing them once. He tore them off and made me wear them around my neck all the way home. Thankfully no one saw. Shit, I better go. I fast wal...

Sleeping Arrangements

by Turbidus on Jun 19, 2018
Gay Male

I no longer recall what triggered the idea of this little story. First, it's not erotic. As usual, I was torn about which category it would best fit in. At the heart of it are the feelings of two men for each other, so I went with "Gay Male". If you're looking for a quick sexy read - this is not it. Although there's no sex, all the characters are over 18....

Solstices Obscurity "Dusk" Ch. 04

by Unrequited_Evil on Sep 16, 2017
Gay Male

"I know you." Looking up from my contemplation of a lizard crawling over my boot, I see a young man, naked like all such here except for me, standing a half dozen feet from me. "You're that scoundrel that betrayed the king!" He was pointing his finger at me like he needed to some how single me out in that massive crowd of one I was standing in. "Which kin...

Lady Trucker Needs Help

by BumpyVT on Aug 18, 2017
Gay Male

True Story... Another Friday night on the road, only 400 miles to go to deliver my load Monday morning. Nothing to do but cruise the radio. Plenty of time to look for some good, hot man sex. Sitting in my Volvo/White at the 76 In Texarkana. Freshly showered, powdered, and perfumed. 5'9"-185 lbs of Daddy Bear Trucker. I had jerked myself off in the shower bu...

On the Boulevard

by endthedream on Aug 18, 2017
Gay Male

He was on the Boulevard again. It was a beautiful summer night. The air was sweet. The columns of smoke that had been here for days had lifted. There was none of the fever that he had had the night before. His head was remarkably clear. He saw things the way they were. He was newly, last week, nineteen. And he was happy. He was immensely happy. He had giv...

First Time With Joe

by alexcarr on Aug 18, 2017
Gay Male

I was so pleased and happy when I started to realize my true leaning. For years I lived under the misconception that, because I wasn't particularly attracted tin a physical sense o girls, there was something fundamentally wrong with me. It didn't occur to me that I was gay or anything like that. There were guys who turned my head for a second look but that...