Gay Leather Boots Stories

4,616 results
Orientation
Length
Source
Infinite Scroll

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...

Airport Sex

by swingerrn73 on Nov 27, 2017
Gay Male

I was transiting in a Middle East airport on the way to Thailand from Europe. Another of my college buddy was already in Bangkok. He had told me about all the happy ending massages and I could not wait to get there. At 18, I was horny like hell just thinking about the amazing sex – I had even tried to masturbate on the plane thinking about the women! Little...

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...

Garage Submission Pt. 01

by LthrBndBy on Jul 15, 2020
Gay Male

This story is pure fiction, pure sex too, not much else. Enjoy. -------------------------------------------- He lives just over two hours from me, and we had been chatting online for a while when I finally got up the courage to submit to him. He told me that the first few times I submit would be in his garage, and I would be blindfolded the entire time an...

First Experience With A Man Ch. 1

by girlboybootsie on Aug 18, 2017
Gay Male

I wasn't always attracted to men. In fact, until I was 18, I never felt confused about my sexual orientation. In terms of sex, I was only attracted to girls, especially sexy ones who dressed in provocative and sexy clothes. I was popular with girls, and had lost my virginity when I was 14. Without meaning to be immodest, I was, and am, a very good looking gu...

Don't Look Back Ch. 11

by ShelleyRunyon on Sep 14, 2017
Gay Male

Despite Lee's warnings—or perhaps because of them—Marshall spent the entire day breaking in his new boots in preparation for the trip to Partners. As added protection, he placed a band-aid on each heel. Better safe than sorry. They surely were beautiful boots. He admired them in his and Lee's full-length bedroom mirror, twisting and turning to catch the whol...

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...

Shattered Boundaries Ch. 03

by Humilifuck on Sep 14, 2017
Gay Male

A black leather gloved hand crawls like a spider up my leg, leaving in it's wake a trail of tingling flesh. It lingers to caress the muscles of my inside thigh before a single leather finger slips between my ass cheeks, stealing softly towards my asshole. A dark figure leans in close, his hot breath scorches my skin as he whispers, "Who owns your ass?" My...

Big Boy Curious

by sr71plt on Aug 17, 2017
Gay Male

We'd met in passing on a porn Web site and had given each other a couple of satisfying private chat cyber fucks. Without openly asking for it, he increasingly pushed our cyber play to the kinky and S&M. His site moniker was Bigboy and mine was Viper, and it didn't take me long to figure out that he turned on to bottom and domination, which was just fine with...

The Black Rose Ecstasy Ch. 03

by twohot4words on Sep 15, 2017
Gay Male

Preparations have to be made first. The sling is up, the bondage table cleared and cleaned, the various toys and equipment assembled and checked out. The gear is the first and, for me, one of the most important considerations -- leather is BY FAR the preferred choice. Maybe it's the act of putting on clothing that is so overtly sexual, or the fact that I am...