Gay Boots Stories

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Police Patrol Boots

by Puppy602859 on Oct 15, 2017
Gay Male

Every Sunday evening I played football with my friends from work, just a friendly kick about to keep fit. Afterwards I would walk back along the canal about two miles to get back home. I never saw anyone on this stretch of the canal, so was a great place to clear your mind. This Sunday after play, I followed my usual routine and started down the tow path. It...

Submitting to Master Ch. 03

by CDinpanties on Sep 14, 2017
Gay Male

Another night rubbing my cock and dreaming of my master. It had been a week since he had taken me and I couldn't get him out of my mind. I was jerking off almost constantly thinking about his black cock in my mouth and ass. All I wanted was his cock, it consumed me. I was shaving all over every other day just hoping against hope he would come over. Afer anot...

My First Visit to a Gay Club

by girlboybootsie on Sep 14, 2017
Gay Male

One Friday night, feeling courageous I decide to do what I have long fantasized about, and go to a male sex club in San Francisco to lose my virginity. I slip on a pair of shiny pink silk bikini panties, which hug my tight buns and wrap a matching pink satin garter belt with lace trim around my waist. I then roll sheer white stockings with French backseams...

Bootblack

by JasonClearwater on Jul 31, 2018
Gay Male

Author's note: This is a very short period tale of an older gentleman discovering the previously unsampled delights of sex with a handsome young man. * Valter Landgrave stumbled over his own feet as he left the tavern, to the tittering and edification of two ladies of the night. He'd fucked them both not long since but had wearied of them and would not b...

First Experience With A Man Ch. 2

by girlboybootsie on Aug 18, 2017
Gay Male

Leading me into his bedroom, I find the sexy pink corset, panties and stockings that he bought the other day at Frederick's all laid out, on his bed. There is also a pair of silicone "boobs." "I didn't even have time to give it to Jessica, so you can have it. I'll leave you alone while you change. You will need to slip the boobs into the cups of the corset....

Getting Lost In a Store

by CowboyBootedNJ on Aug 18, 2017
Gay Male

Jerry was a normal acting male, he worked hard for a living, went home to his wife every night, they made love on occasion, etc. They had two grown children, now out and on their own, Jerry can now go back to the way he was before kids, more sexual freedom, and who he really is. When he goes to work he cannot be so liberal, he must wear his suit properly, we...

Derek Pt. 03

by TAHammer on Apr 27, 2020
Gay Male

Everybody was decked out in cowboy boots, jeans, and bandannas at the afternoon barbecue. Of course, Derek with his sleeveless button-up shirt, tight jeans (with a big buckle belt), and cowboy boots looked like the Playgirl cover model for the cowboys issue. Everyone watched him swagger around the patio. Karen gave him a cowboy hat, and every gay guy and str...

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...

The Ride Master Ch. 01

by oralguy82 on Sep 14, 2017
Gay Male

As a extra credit activity for the junior college I was attending, I was engaged by the Ride and Board Stables as a helper for the summer, doing stable work and other jobs about the riding-school. At least that was what I thought I had been employed for. But it soon turned out that the Ride Master, Jason, had other plans for me. The first day or two I helpe...

Leather Sir Pt. 10

by LthrBndBy on Jun 9, 2020
Gay Male

It's been two years since we moved to Madison and started what I call a new life together. We've since gotten married in Wisconsin. It was a nice ceremony. We have a decent sized group of friends into Leather and Bondage. They all attended and Sir and I were both dressed in full leather for our nuptials. Monday through Thursday are typical work days. I fou...