Gay Thigh Boots Stories

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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...

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...

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,...

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...

Chains Pt. 03

by TAHammer on Mar 17, 2020
Gay Male

Jacopo needed allies. People on his side. Nothing was going to work if he didn't have some help. His contact with people was very limited. Besides Horst, John and Andreas were two of the very few people with which he had contact. Andreas was with him almost of the time unless there were other prisoners working around him. Andreas liked to run around and bar...

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....

First Time With A Guy

by girlboybootsie on Sep 16, 2017
Gay Male

One Saturday morning I awake to find the sun shining through my bedroom window. It looks as if it will be a beautiful day and I feel wonderful as I remember the dream I was having just before I woke up. In it, I was being fucked deeply up my ass on all fours by a beautiful blond hunk with a lovely long and hard cock while sucking on the cock of his twin! I w...

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...

Luke and the Two Bears Pt. 01

by stud28 on Aug 7, 2019
Gay Male

Luke had just turned 19 and had only had one hand job and one blowjob experience. He had been communicating with a guy from an app for about six weeks. They finally agreed to meet and Leo drive to his city for an overnight stay. He arrived at the Motel 6 and went to room 325. Randy opened the door. He was just like his profile 42, 5'9 230 lbs. bald head and...

Move In Day Ch. 02

by bboy13 on Aug 18, 2017
Gay Male

Pt. 2 (Hunting Trip) It has been a few weeks here at college. Josh turned out to be a hunter, which I think is so much hotter. I mean, country boy in camo, who could resist? "Do you want to scout out a few places for deer?" Josh offered. I had a few things come to mind when he asked me, and it was far from anything that had to do with deer. "Yeah, sounds...