Gay Tailor Stories

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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 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...

The Leather Tailor

by LthrBndBy on Jun 9, 2020
Gay Male

This story is purely fictional. All characters are consenting adults over the age of 18. I had decided I needed to have someone tailor my chaps and long sleeve shirt so they fit me better. I found a local place to have it done, so away I went. He had me put them on of course and went about adjusting the legs and pulling them tighter, asking me question...

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 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...

We Meet Eventually Ch. 03

by 1suitedbi on Sep 23, 2019
Gay Male

Chapter 3- Morning at the Spa-Lunch-Visit to the Tailors Wakening at my usual 6.30am it was strange but very satisfying to find Will beside me in bed. Slipping out from under the sheets I made my way through to the bathroom slipping off my silk pyjamas and began my normal ritual of the three s's, slipping into a silk robe I returned to find him still asl...

Old Wounds, New Love Ch. 04

by CrimsonWeb on Sep 14, 2017
Gay Male

Ethan stood scratching his head staring down at the sleek suit laid out on the bed before him. It was a navy blue with thin pin stripes and exquisitely tailored. "Stop staring at it at it and just put it on," Afton teased. He came to hover near the bed wearing a smirk. "How do you know it will fit me?" Ethan asked. "Because I know men's bodies, and I kn...

Turning the Table

by LeathermanCraig on Aug 18, 2017
Gay Male

Mark walked into the room and threw his tie and jacket onto the bed. He unbuttoned the tailored shirt and dropped the slacks to the floor. Getting home on Friday afternoon was always one of his favorite times. He could drop all of his office drag – the Brooks Brothers suits and shoes – and get ready for another weekend of fun. He enjoyed his job as the head...

On The Pill

by kicky1000 on Aug 18, 2017
Gay Male

Brock Barry Peterson was the handsomest man I had ever seen. He was over six feet tall and had smooth clear skin, blue blue eyes and white white wavy hair. He was always impeccably dressed in expensive well-tailored suits, crisp ironed shirts, and tastefully colored ties. He wore a special cologne. I don't know what it was, but it was heady. Sitting across f...

A Day at the Swimming Hole Pt. 02

by ibjtjones on Jan 16, 2019
Gay Male

Chad texted me saying he had seen DeShawn, he really liked him but was sort of intimidated, and he was tailoring a new suit for him in addition to a couple pair of pants to start with. DeShawn also said he wanted to be my personal dresser, he'd make the order, and I'd go online and pay. Chad asked how I had been and asked me if I wanted to meet for lunch, s...