Gay Boots Stories

1,920 results
Orientation
Length
Source
Infinite Scroll

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...

Highway Patrol's Lucky Night

by ibjtjones on Nov 27, 2017
Gay Male

Its 2 am and I am sitting in my patrol car on the side of the interstate running radar thinking about my life. It's kinda quiet tonight. I currently am employed as a highway patrol. I have been working with the highway patrol 10 years. I am 6'5", 260 lbs., size 14 shoe, a 34" waist shaved head and dark skinned as night with a 9.5" cock. I see my radar flash,...

Daniel's New Boss Ch. 06

by Torcojack on Sep 23, 2019
Gay Male

Daniel began to regain consciousness at around 11 AM, he had woken but not yet opened his eyes. It seemed dark based on the light beyond his eyelids. When he did open his eyes, he saw that it was not dark outside at all but full bright sunlight in the back yard. His mouth tasted strange, salty, mild chlorine, like he had swallowed water from a salty swimmin...

FtM Gay Gangbang

by Waterdwarf on Apr 15, 2020
Gay Male

*All characters in this story are over 18 years old.* "Tonight?" popped up a text on my phone. "Yes Daddy," I quickly texted back. I had met this man at a transgender support group, we had both been born female, but had been on testosterone for over a decade, as well as having had our breasts surgically removed. To anyone at the local gay leather bar,...

Best Friends Become Lovers Ch. 04

by UnderMyKilt on Nov 29, 2017
Gay Male

For those who haven't read them or have forgotten, you may have to read the previous stories to know how we got to this point. I hadn't intended for this to be series, but it turned out that way and this will be the last story under this series title. As we left off at the end of Chapter 3, Wayne and I had just fallen asleep after making love at a remote ca...

Connor's Pretty Horny Pt. 09

by connorwitmer on Jan 30, 2018
Gay Male

So, to say the least, I had suddenly become hot shit. Just kidding. If anything, I now felt like a complete imposter. Alex seemed to have accepted me as somewhat cool, and now Robbie added a level of intrigue, and Henry was ever present. Despite being hot shit, I rarely saw a text from Alex. I had already placed him in the category of "people who don't text"...

David, Daryl and I (Clayton)

by ibjtjones on Feb 6, 2018
Gay Male

We were on duty almost to the end of our shirt, David was running radar in one place and me in another spot on the interstate. We were texting and just waiting for the shift to end. It had been a slow night because the weather had been nasty. David said he was fixing to move so I took the opportunity to move also. When I next heard from David he told me he h...

Truck Stop Fuck Ch. 02

by hungbottom on Aug 30, 2017
Gay Male

After the hot fuck I just received from the trucker I thought I would just rest a bit and go back to my apartment. Sitting on the guard rail of the access road I watched as the squad car pulled up by me and stopped and both of the officers got out of the squad car and came over to me. Both of the officers were dressed in short sleeved uniforms that looked...

Eight Seconds

by KeithD on Feb 6, 2018
Gay Male

"Stop that," Cal said with a groan, "You're gonna make me come." "That's the idea," Vince said, lifting his mouth off Cal's cock, his fingers still wrapped around the root of the shaft. They were an hour north of Denver on I-25, outside of Fort Collins, making about as good time as Cal's old rattling F150 pickup could do. Vince had been playing with Cal's e...

A New Job Pt. 02

by LthrBndBy on Jul 6, 2020
Gay Male

It's been three days since I started as Jim and Frank's houseboy. They compliment my work as I move throughout the house dusting and cleaning. Their compliments usually consist of smacking an open ass cheek and saying, "very nice boy." Almost every night has been some sort of sex with one or both of them, always ending up as me eating a load or two. I'm th...