Gay Rubber Boots Stories

3,284 results
Orientation
Length
Source
Infinite Scroll

A Surprise For You

by Wildestthang on Aug 18, 2017
Gay Male

I waited as I heard his car pull into the driveway I held my breath, slowly letting it out. He said when he called that he had something new for me to try. I wondered what it could be. I knelt in the bedroom on the floor naked, my chain collar around my neck, the chain lead hanging down cold between my legs. My hands hooked together behind my back in the sym...

How I Became a Sissy Slut

by DixeenormousToo on Sep 15, 2017
Gay Male

I wish I knew I had these sissy urges when I was younger. Who knows, instead of getting married, having kids, and living the "American Dream," I might have discovered hormones, worked my body into shape, and become a tranny porn star. After all, how often does the American Dream really work out anyway? I'm unhappily divorced, my oldest is on his 6th year of...

First Time With A Man

by Willing2Do on Apr 3, 2019
Gay Male

His knob pressed into my anal spinchter. It felt somewhat like a raquetball being shoved up my ass but different; round, hard, yet yielding as my anus gave way to its invasion, but warm, wet and pointed on the end. The rod pushing it into me was a bit thinner, but also hard and at the same time soft, fleshy, thickly veined and slimed with the lubricant he ha...

Blink: Five

by KenjiDeSade on Aug 18, 2017
Gay Male

The following story is a fictional account. The characters are entirely unreal and so are their situations. Thus no direct attention was paid to probability or safety for the characters. Such practices should not transfer over to real life situations. Practice safe, sane and consensual sex. For your own damn good. If you have problems or issues with queer po...

Michael Found His Discipline

by stud28 on Aug 21, 2019
Gay Male

Michael was a 40 yo man who stumbled across an app designed especially for those with kinky interests. He located a profile that peaked his interests. Mr. S was 71, 6'5, stocky, hairy chest, hairy back which was silver/white. In his profile pic, he wore a leather harness, leather jock strap, and leather hood and held a paddle in one hand and flogger in the o...

Blink: Four

by KenjiDeSade on Aug 18, 2017
Gay Male

The following story is a fictional account. The characters are entirely unreal and so are their situations. Thus no direct attention was paid to probability or safety for the characters. Such practices should not transfer over to real life situations. Practice safe, sane and consensual sex. For your own damn good. If you have problems or issues with queer po...

My New Daddy Ch. 03

by sissytoy20 on Mar 6, 2018
Gay Male

The buttplug that Sam had unceremoniously forced inside my tight asscunt had hurt like hell, but I'd enjoyed the feeling of being forced open with no warning. The little, pink butt plug wasn't very large, but it had felt like a giant donkey dick in my ass. It had flashed by in Sam's hand so quickly, maybe it was larger than I thought. It felt huge in my butt...

Trucker

by Ken Nitsua on Aug 18, 2017
Gay Male

Revised version copyright 2014 by the author. * The cab of the big rig is huge and cool. I smell leather, diesel fuel, and cigarette smoke. The place hums with the vibration of the idling engine. I turn to the trucker sitting in the driver's seat, his eyes frank with lust. One rough hand rests on his denim-clad thigh, the thumb moving back and forth over...

Blink: One

by KenjiDeSade on Aug 18, 2017
Gay Male

The following story is a fictional account. The characters are entirely unreal and so are their situations. Thus no direct attention was paid to probability or safety for the characters. Such practices should not transfer over to real life situations. Practice safe, sane and consensual sex. For your own damn good. If you have problems or issues with queer po...

Sacrificed by Curiosity Ch. 11

by sr71plt on Sep 14, 2017
Gay Male

The fresh, clean air of the mountain country was good for Doug. Within a few weeks, I was able to harden his cock through, first sucking him off, and later, taking the lead in sitting in his lap with his dick up my ass canal. Merely days later, he was back to humping me in his favorite sidesplitting position. But the fire was not in our fuck sessions yet. We...