Gay Rubber Boots Stories

3,284 results
Orientation
Length
Source
Infinite Scroll

The Good Old Boy Ch. 02

by carsonshepherd on Sep 25, 2017
Gay Male

O’Brien & Son Auto Body was out behind my brother’s house. Andrew and I grew up in there, learning to fix cars with our dad, who was the best mechanic in a two hundred miles radius. People waited weeks to get their cars back from our dad; cars lined up in our yard like it was a parking lot. I’d been away for a long time, writing instead of working on cars; I...

Liam's Submission Tested Pt. 05

by PupTracer on Oct 5, 2020
Gay Male

Marcus brought entirely too much food to be defined as a "snack". He had piled on peanut butter and jelly sandwiches, strawberries, cookies, almonds, even slices of cake. When he attempted to precariously juggle it all on one flimsy paper plate, it didn't end well for him. As he lowered the plate to me his rather large boot tapped the edge of the bedframe an...

Dressage Training

by sr71plt on Sep 19, 2017
Gay Male

(Written for specific fetish request by SA) "The Hamiltons have asked whether you can go to Lexington with Mr. Hamilton for the Dressage at Lexington competitions in July, Santo. You'd be his groom for the three days there, and if you worked out well, you could stay on helping them here at Ash Creek Farms for the rest of the summer before you go back to s...

Macks R Us

by Troubadour on Aug 18, 2017
Gay Male

Mike and I have been messing about for almost a year now He lives next door and at eighteen is a few months younger than me. He is more delicately built than me and with longish fair hair has a slightly feminine look about him. What we do started off as normal boyish behaviour. We began as many boys do by groping each other which quickly developed into exte...

Give the Student What He Wants Ch. 03

by dr_bitch on Sep 16, 2017
Gay Male

Let's see. As I tell this story, relaxing with my head in my young Master's lap, kissing his stiffening cock now and then, I'm trying to catch you up to how I got here. Today is Friday, January 27. I believe I left you last time on Sunday night, happily licking and chewing my own cum off of a damp washcloth. You see, my Master, a college student I call Jas...

Lash's New Lover Ch. 01

by adoration on Aug 18, 2017
Gay Male

Author's note: those readers of the Peeing on the Peeper series will recognise the Leather Man character from one of its chapters. In that story the Leather Man was not allowed his wicked ways with the Peeper, so I've created a story especially for him. * The phone rang in my office and since my useless assistant was on one of his two-hour fuckin' lunch br...

Finding Myself

by Pussrider on Aug 30, 2017
Gay Male

My name's Richard McIntosh, and until a couple of months ago I was a perfectly ordinary middle-aged businessman, husband and father. I'm 45 and work as an area manager for an international finance company in a large city a couple of hours from London. My wife is Alison, my eldest daughter Pippa has just started university and my youngest, Katie, is in her la...

First Time Training Session Ch. 02

by playtime2728 on Aug 30, 2017
Gay Male

My throat was sore for a week. It got so bad that I lost my voice-my friends were all telling me to go to a doctor to see if I had strep, while I was secretly turned on every time I tried (and failed) to say something. No one suspected in the least that I was whispering because a strange guy with a big dick had given me an hour long lesson on what deepthroat...

The Hanky Code Pt. 08

by His_fag_wife on Sep 14, 2017
Gay Male

A round of applause went through the room accompanied by some cheering. It seemed I had done well as Masters' pig. As I squatted, completely spent, with my ass pussy completely filled by the huge barrel, filled with nearly 2lbs of rubber, not just stretching my actual pussy but also my insides. My lips still covered in cum and piss, I was still involuntaril...

Ryan Jackson's Great Stretch Pt. 05

by Bi_Panda on Sep 14, 2020
Gay Male

Written by: Bi.A.Piggy Reposted from other sites Standard Rules and licensing applies. This story comes from the depths of my mind. I am not a professional writer just someone who like to put the dirty ideas in his head online for others to enjoy. I don't care if you don't like my style. If you don't like what you're reading, close the window and read so...