Gay Boots Stories

1,920 results
Orientation
Length
Source
Infinite Scroll

Road Romeo

by sr71plt on Aug 18, 2017
Gay Male

He was half on, half off the short bunk, with one foot leveraged high to one side on a grab handle in the top center of the back wall of the cab, his back arched on two hard pillows, his hands open wide over the driver's naked buttocks, fingers digging into flesh, moaning in long, building moans matching the long slides of the hard ramrod inside him. The dri...

Abs and I

by abadmirer on Sep 16, 2017
Gay Male

When I left school at the age of 18 I was very skinny ; 5 foot nine inches and weighed about 8 stone (not quite the 98 lb weakling of the advertisements but not far off!) When I went to university I decided to go to a gym to put on some weight. There weren't too many around in the late 1960s, but I found a funny old place in Upper Queen Street. We'll call it...

The Leather Tailor

by LthrBndBy on Jun 9, 2020
Gay Male

This story is purely fictional. All characters are consenting adults over the age of 18. I had decided I needed to have someone tailor my chaps and long sleeve shirt so they fit me better. I found a local place to have it done, so away I went. He had me put them on of course and went about adjusting the legs and pulling them tighter, asking me question...

A Very Dirty Little Sissy 'Girl'

by keptsissy on Aug 31, 2017
Gay Male

I love to please my boyfriend. I masturbate thinking about that. A lot. To hear him when he's in me, on top of me, lost to my tight little hole or my mouth, I love the sound of him, the 'man' noises he makes! But as much as I like to please him, I just like to please men. Do I ever. I've been at it since just after high school. And there is nothing hotter th...

"Hey man, whatcha doin"

by TallyMans on Aug 30, 2017
Gay Male

"Hey man, whatcha doin?" My co-worker sits, with his back towards me, at the table and chairs in our hotel room, as I look from the bathroom to the front of the room. My co-worker is shirtless. He had stripped off his dirty grungy button-down short-sleeve shirt the moment we walked into the shared hotel room, the fleabag hotel, after he cranked up the A/...

Love & Latrines Pt. 01

by 100331 on Aug 18, 2017
Gay Male

I woke up in late in the afternoon, still dressed in the clothes I wore during the party. I had a huge hangover and my morning wood was just throbbing. My stomach began growling and my bladder was about to burst. I rushed to the toilets, and there I saw him. I live in a big house with nine other guys, my best friends. We knew each other because our girlfrie...

Leather Sir Pt. 03

by LthrBndBy on Jun 1, 2020
Gay Male

I woke up on Sunday, refreshed, well rested, and hornier than I felt in a long time. I got out of bed and walked to the kitchen for some much needed coffee. I very quickly remembered the plug still in my ass. I smile and walk into the bathroom instead. Figured I would take it out, clean it, do my morning bathroom activities, and then put it back in. Whil...

Getting . . . Educated Ch. 09

by sr71plt on Sep 14, 2017
Gay Male

The exhaustion of and loss of strength from the previous day's unexpected sex encounters may have accounted for my tennis match the next day, but it's just as likely that Ben was just a much better tennis player than I was. He agreed to let me try to recoup the loss and set up another match for two days hence. As I had hoped, we were the only ones in the gr...

We Can Call it Paradise

by TuckerMcCallahan on Aug 18, 2017
Gay Male

Author's Notes: This is a copyrighted work of fiction written by Tucker McCallahan. All rights reserved by Tucker McCallahan. If you are reading this story anywhere but at Literotica then it has been posted without permission. Please report plagiarism to the contact on my profile. ***** "I need a beer." "No kidding. A beer and a shot." "Did the guitarist...

Sex and the Magic Lamp Ch. 04

by maxpotter on Sep 5, 2018
Gay Male

Work was a bit like foreplay for me. I saw Matt around a bit, granted I kept an eye out for him, and made my way to go by his desk a few times. Matt was a bit on the short side. Nothing major, just a little below average. He had some significant pecs. Very prominent in the shirts he wore. He had a great ass, and that ass was accented by his boots. Like all r...