Gay Tailor Stories

112 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2024 SmutMD.com

Bobby's First Suit

by timmywells on Aug 18, 2017
Gay Male

"I thought it would be a good idea to buy Bobby a suit," Gladys Bradley told the little Italian tailor whose shop was down the road from their apartment. "Not only for the dance, but with Bobby going to college in a couple of months he'll probably need a suit for other things." "A college boy now huh?" Tony Caruso asked as he rubbed the dense 5 o'clock shad...

My Erotic Education - A Journal 03

by rae121452 on Oct 14, 2017
Gay Male

The next morning, I awoke disoriented not only to place but also situation. I was in my uncle's bed and as I came to consciousness lying on my side I became aware first of my uncle's body pressed against my back and his arm draped over me, his hand firmly wrapped even in his sleep around my throbbing morning erection. Also the feeling of his big erect cock s...

The Tailor

by TitusMoorhead on Sep 28, 2020
Gay Male

Despite his impressive body, the fit young man still looked awkward as he stood in his boxer briefs in front of the mirrors that reflected him from all sides. Will didn't mind the view of his chiseled frame, especially the way the light grey fabric of his underwear accentuated his tight bottom and thick bulge, but he wasn't used to being prodded at while so...

My Erotic Education - A Journal 07

by rae121452 on Dec 30, 2017
Gay Male

Mr. Steinberg, the tailor, had sent word that he was ready to perform my first fittings of my new clothing. I was also ready to sample the oral services he had performed upon Will and my uncle at various times in the past, so it was with an excited and half erect member that I arrived at his establishment. Disembarking from the carriage I noticed that Will...

The Tailor's New Shop Boy

by ThomasStevenson on Nov 18, 2019
Gay Male

"Gotta go, this is my stop." Philip fired off a farewell text to his friend as he got up, shoving his thick, hairy, tan feet into his flip flops. He didn't bother adjusting his singlet, which continued its slide down one of his muscular shoulders, slouching halfway down one side of his beefy rugger's physique. A dusting of reddish chest hair made a thin "t"...

The Customer (Dexter's Saga) Ch. 11

by JoyStick56 on Sep 14, 2017
Gay Male

Disclaimer: This story may contain scenes of a graphical nature that may not be legal in your area. If you are under 18, or if material of this nature is illegal in your present location, please leave now. By reading on, you are confirming that it is legal for you to view the material in this story. This story is a work of pure fiction. Names, characters, p...

Millstone - Novel 01 Ch. 13

by RickHeathen on Oct 19, 2020
Gay Male

Millstone - ONE - (Hanging the Chimney Hook) All Rights Reserved © 2020, Rick Heathen This is a work of fiction. Names, characters, businesses, places, events, locales, and incidents are either the products of the author's imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental...

The Three Day Pass Ch. 18

by JoyStick56 on Sep 14, 2017
Gay Male

This is a work of fiction, and as such the characters are not bound by the usual dictates of modern society. Unsafe sexual practices can be undertaken with impunity only in the world of fantasy. In reality, it is your obligation and your right to play safely, sanely and healthily. I hope you enjoy my work, and if you have any comments, or ideas that may in...

Millstone - Novel 01 Ch. 05

by RickHeathen on Sep 14, 2020
Gay Male

Millstone - ONE - (Hanging the Chimney Hook) All Rights Reserved © 2020, Rick Heathen This is a work of fiction. Names, characters, businesses, places, events, locales, and incidents are either the products of the author's imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental...

The Customer (Dexter's Saga) Ch. 13

by JoyStick56 on Sep 14, 2017
Gay Male

Disclaimer: This story is a work of pure fiction. Names, characters, places, and incidents are either the product of the author's imagination or are used fictitiously, and any resemblance to actual persons, living or dead, events, or locales is entirely coincidental, and no harm or slanderous intent is implied or intentional. Other than that the usual discla...