tinker-tailor
GAY SEX STORIES

Tiner Tailor

Tiner Tailor

by Ja0b
20 min read
4.85 (22500 views)
cmnmfirsttimefucedgingbulge
Loading audio...

I felt like I was stepping back in time as I entered the tailor's shop located off a side lane in the Garment District. The old-fashioned overhead bell jingled announcing my entrance as the door closed gently behind me blocking out the sounds of the snow-covered street on a late Friday afternoon. The shop had an old school feel to it as a wave of warm leather-scented air welcomed me. Without the racks of suits and accessories filling the showroom, you might have thought you had walked into a gentlemen's club from the last century with the store's tasteful lighting, wood paneling, and comfy leather wingback chairs placed around the space. No wonder my Dad liked this place.

At the back of the showroom, I could see a shorter man with a shaved head standing behind a counter serving an older gentleman as he rang up a sale. The man behind the counter glanced up at me through wire rim glasses and smiled under his thick, dark moustache, "Good afternoon sir. I'll be right with you."

Nodding back at the man, I felt out of my element in the posh shop with my faded jeans and tired bomber jacket as I brushed snow off my shoulders. I was also feeling buzzed as fuck having just shared a joint with a gym buddy after our workout before taking the subway to this appointment. I was regretting that decision already. Weed made my big head foggy and my little head horny which was the last thing I needed right now. I was at the tailor's for a suit fitting for my upcoming wedding. My Dad had offered to pay for a custom suit provided I used his tailor. He had one of those jobs where he usually wore a suit to work and he was a longtime customer of Hitchcock & Sons. I remembered my Dad bringing up the topic in our kitchen a few weeks ago, "Nobody fits a suit like Nigel. Trust me, Grace will fall in love with you all over again when she sees you at the altar in a custom suit. This is your big day too and we want you to look your best."

My Mom had nodded beside him and added, "It's true, your Dad always looked so dashing in a suit that it sealed the deal for me. He was and is a good looking man but doubly so in a three piece," as she leaned over and kissed my grinning father on the cheek. Was he blushing?

While my father

was

a sharp dresser, I was hesitant to visit some old time tailor worried that I'd end up

dressed like an old man

for my wedding but I took a leap of faith and accepted my Dad's offer. My father was overjoyed and immediately called Nigel, the tailor at the shop, and booked a fitting appointment at the end of the month. Given I would be away at school until then, my fiancée Grace had previously visited the shop on her own to select a dark plum fabric that would work well with the rest of the wedding party colors, and provided my basic measurements. While I had seen a sample of the fabric she had selected, I was visiting the shop for the first time today to be properly measured and fitted with our wedding scheduled in two weeks. I was a bit nervous about my father and my fiancée making so many decisions on my behalf which I guess was part of the reason I had accepted my friend's offer to toke up. I had hoped it would calm my nerves but so far it wasn't working, I just felt stoned, oh and horny, or hornier to be accurate.

I looked around the store admiring the rich fabrics and colorful selection of silk ties. I imagined there weren't many shops like this left in the city since jeans became acceptable work attire in most offices and

work from home

became a common acronym. The older customer finished paying for his items and walked back towards the entrance, smiling and nodding at me before stepping out of the shop with another ring of the bell over the door. The shorter man finished up behind the counter and walked towards me with a warm smile, "I'm sorry for the wait. How can I help you?"

Feeling foolish, high, and underdressed in my jeans and t-shirt, I responded, "Uh, I'm here for a suit fitting. My name is Henry Taylor."

The man's face lit up immediately, "Ah, Robert Taylor's son. I should have recognized you from your handsome face. A pleasure to meet you Henry," as he reached forward and shook my hand in his surprisingly firm grip clasping our joined hands with his other hand, "My name is Nigel and I'll be fitting you today." While Nigel was barely 5 feet tall and probably in his mid forties, he looked compact and muscular under his suit trousers and vest. He was also wearing a rich silk tie and a crisp white dress shirt with the sleeves rolled back on his hirsute forearms, and a requisite measuring tape draped around his neck. I could see his biceps bulging through the white fabric of his shirt as he gripped my hand. While his head was shaved, he had a 5 o'clock shadow on his chiseled jaw, and a thick luxurious dark moustache below his bespectacled twinkling eyes. Not surprising for a tailor named Nigel, I detected an English accent. "I've known your father since he was your age, such a wonderful man. Come in, come in," as he finally released my hand and guided me deeper into the store.

Turning his head back to me as we walked, Nigel continued, "Congratulations on your upcoming wedding. I met your fiancée last week when she was in selecting material for your suit. She's a lovely young lady and the two of you will make a handsome couple." I blushed at the praise the sturdy little tailor was throwing my way as he guided me towards the fitting room with his hand on my shoulder. "Oh wait, let me put up the closed sign before we head back. I'm on my own tonight but it's a quiet night with the snow so no one should mind if we close a few minutes early. There's usually another person working but they're off sick."

I nodded stupidly as Nigel walked back to the door, flipped the sign to 'Closed' and locked the door. "Excellent, now we won't be disturbed. Let's head back to the fitting room and get started. I need to confirm your measurements and try on the partially made suit for fit." Turning to me, he whispered in a conspiratorial tone,"I think it's going to be a beautiful garment." Nigel's impish face glowed as he talked passionately about my suit. Obviously, he enjoyed what he did. For a man with a diminutive stature, there was something uber masculine and commanding about Nigel. I'd noticed he had legs more suitable to a wrestler than a tailor when he had walked to the door and back.

Trying to not to appear stoned, I responded, "I'm looking forward to seeing the suit. I grew up listening to stories about Hitchcock & Sons and what useful advice or funny stories you shared with my Dad. He swore by your suits and loved the compliments he always received when wearing one. When I needed a suit for my wedding, my Dad gave me no other option than Hitchcock & Sons."

"That is so kind and humbling to hear and thank you for trusting us with your big day. Please say hello to your father. I've always enjoyed his visits and it's been far too long. Come, come... let's get started," as Nigel rested his big hand on the back of my neck and guided me towards the large fitting room behind the counter, while flipping off a bank of switches on the wall lowering the lights in the front showroom. I was getting the feeling that Nigel was a pretty handsy fellow but then such is the nature of a tailor I was guessing.

The fitting room was hidden from the street and similar to the front of the store with it's old English warmth and charm. It also had wood paneling with thick carpeting, and several mirrors spread around the perimeter of the space with a raised platform on one end in front of three larger mirrors. There were two leather club chairs placed on the floor and two small curtained change rooms at the back of the space.

"Before we begin Henry, can I get you anything? Coffee, water... brandy?" Impressed with the full service treatment, I politely asked for water.

"Water?" he looked at me questioningly, "Are you sure? Being fitted for your wedding suit is a special occasion and worthy of a decent brandy. Besides, it's the end of a snowy day and I might just join you if you do," as he grinned and winked. There was something very impish about Nigel.

📖 Related Gay Sex Stories Magazines

Explore premium magazines in this category

View All →

"In that case, sure, I'd love a brandy," I smiled back at Nigel liking him already and starting to relax. Part of me was envious of my Dad and this part of his life that was so foreign to me. It felt so civilized and welcoming but I'd have to watch the alcohol on top of my healthy buzz.

"Excellent, I think we're going to get along well. Let me pour the brandies while you undress so I can take your measurements. I normally do this

before

I begin a suit but I had to use your fiancée's estimates in this case given your limited availability. You can hang your clothes in one of the change rooms," pointing to rear of the room.

"Uh, okay." What the hell, I needed to strip? I stupidly asked, "Do you mean jeans and everything?"

"Yes, please. Everything but your underpants, and socks if you prefer to leave them on. It's difficult to take accurate measurements on top of clothing," explained Nigel while he poured two generous snifters of brandy from a small bar beside the entrance to the room. "Let me turn the heat up a couple degrees so that you're comfortable."

I felt completely flustered by the request and unsure if I should go into one of the small change rooms and undress behind a curtain or strip down in the middle of the room as Nigel was going to see me in my underwear regardless. Realizing I was probably overanalyzing what is likely a common request from a tailor, I walked to the rear of the room and took off my shoes as well as my jacket, t-shirt, and jeans, hanging them on hooks inside one of the change rooms. I was left standing in my gym socks and a pair of boxer shorts with a big yellow smiley face on the front. Oh god, why did I have to wear these shorts today? I hadn't even considered that I'd have to strip down.

"Perfect," Nigel acknowledged as I walked back to him, "By the way, I like your shorts," Nigel winked at me as he held up the two glasses of brandy. "Can I get you to stand up here? The lighting is better." indicating the raised platform by the mirrors as he handed me my brandy. Raising his glass, Nigel said, "First of all Henry, congratulations on your upcoming nuptials and thank you for making Hitchcock & Sons a small part of your day. I'm hoping this will be the first of many visits and I wish you years of happiness with your beautiful bride," as he tapped his glass against mine. Despite standing there in my ridiculous shorts, I was touched by his short speech as I lifted the glass to my lips and took a healthy swig of the rich amber liquid. I felt the liquor warm my throat as I swallowed. Damn, this was some good shit. I could get used to this treatment as I took another sip enjoying the smell and rich flavor. Noticing my appreciation of the brandy, Nigel asked, "Do you approve?"

"I do, very much so, thank you," smiling back.

"Very good. We always keep a supply of quality brandy on hand at Hitchcock & Sons so don't be shy. There's a table to your right if you want to set down your glass otherwise enjoy." Placing his own glass on the table and looking down at my ugly smiley face shorts, Nigel scrunched up his face and asked, "Do you always wear boxer shorts?"

"Uh, yes. Pretty much."

Nodding, Nigel said, "Excellent. Boxers are much more comfortable than those awful briefs so many men wear these days. You're much less constrained in a boxer and with the looser fit of a suit, I think it shows your attributes to their advantage," as he looked at my crotch. Was this guy really talking about my junk? I did prefer the feel of my cock swinging freely in boxers but I was somewhat uncomfortable discussing it with my Dad's tailor. While staring at my shorts, Nigel suddenly asked, "What side do you dress on?"

Befuddled by his question and Nigel's continued laser focus on my crotch, I stuttered a response, "Um, what do you mean?"

Smiling at me, Nigel patiently explained, "Most gentlemen prefer to position their...

todger

on the left or right side of their shorts. It's just a matter of preference for some. With a custom suit, we ask so that we can cut the suit appropriately, especially when the customer is...

generously endowed

." Nigel looked meaningfully at the bulge behind my smiley face shorts. I guess I was giving off big dick energy.

The room spun slightly as I tried to process how I had ended up standing in the back of a closed clothing store on a winter evening perched on a dais in my underwear stoned, horny, and slugging brandy, while a short, muscular, English tailor commented on the heft of my

todger

. I could already feel the effects of the alcohol on my empty stomach and nervously took another gulp of brandy before replying, "Oh, okay. I guess I normally dress on the left," while noticing ironically that my cock was currently resting on the right.

🔓

Unlock Premium Content

Join thousands of readers enjoying unlimited access to our complete collection.

Get Premium Access

🛍️ Featured Products

Premium apparel and accessories

Shop All →

"Excellent," Nigel responded nodding as if I had said something clever. Showing no signs of embarrassment, he efficiently pulled the elastic waist of my smiley face shorts forward and reached in to grasp my plump cock in his warm hand and move it from the right side to the left as casually as a waiter might straighten your napkin. With my dick now in its

proper

position, he withdrew his hand and released my waistband. What had just happened? Was it normal for a tailor to handle your cock?! I couldn't imagine that it was but then again I had never visited a tailor before. I decided to ignore whatever had just happened as I gripped my glass of brandy and took another sip. Unfortunately, I could feel my cock responding to being handled as I mentally cursed my fiancée... again.

Last week, Grace had suggested we should stop sleeping together leading up to our wedding to make our first night as a married couple extra special. While my first impulse was to ask her if she was fucking crazy, I knew she was putting a lot of effort into our wedding and the stress was wearing on her. Wanting to avoid a

Bridezilla

moment and with a performance worthy of an Oscar, I calmly responded, "That's a great idea babe. I'll miss our sexy times together but I can't wait to unwrap my beautiful bride the night of our wedding." Based on her happy response, that was the correct answer but since then I'd been horny as fuck and kicking myself daily for ever agreeing to such a stupid idea.

Trying to think of anything other than sliding my hard cock into Grace's tight pussy, I willed my dick to behave but I was definitely semi-hard at the very least. In my experience, horny plus weed always equals super horny, so once again I wondered why I had ever agreed to smoke a joint before my appointment. For his part, Nigel didn't appear to take notice of my thickening rod as he grabbed a small pad of paper, pencil, and the measuring tape from his neck and asked me to turn facing the mirrors. "Before we fit the suit, I'd like to take some accurate measurements. It will help with the final assembly, plus I'm hoping you'll be a repeat customer so we'll have your measurements on file. This shouldn't take long."

Nodding my agreement, I noticed in the mirror that my shorts were definitely bulging which Nigel was bound to notice. Reaching for my glass, I took another sip of brandy. "Good, good. You have an appreciation for fine brandy just like your father. I need to limit myself to small sips while I work but please go ahead and enjoy. It's perfect on a cold evening like this," topping up my glass. I was definitely feeling lightheaded from the alcohol and dope combination but it was helping me to relax.

"All set?" Nigel looked up at me with his measuring tape in hand? Nodding in response, he got to work first reaching up in front of me to wrap his measuring tape around my neck. Given his diminutive height, he had to get close to reach my neck and I could feel his solid body pressing against mine. I could also smell a hint of spicy cologne as his furry arms brushed against my shoulders and his torso bounced against my dick. I was starting to realize that being fitted by a tailor was a somewhat intimate activity. After each measurement, Nigel would write neatly in a small notebook that he carried in his pocket. Instructing me to lift up my arms, Nigel passed the end of the tape behind me with one hand while grabbing it with the other, while his face was pressed close to my chest. Looking down, all I could see was his shaved head and swarthy face inches from my nipples as he successfully maneuvered the tape around my back and connected the ends in the middle of my chest. The tape and his fingers brushed against my nipples sending a shock through me.

"You are very solidly built Henry. Do you play a lot of sports?"

"Uh, thanks. Yeah, I try to go to the gym and do some running."

"Whatever you're doing, it's obviously keeping you strong and fit. You'll cut a fine figure in a suit." Nigel was now measuring the length of my arms. The problem was he kept bumping into to me as he moved, specifically my cock, and I was feeling a warm flush as my shaft thickened. Even the light brushes against my skin with his hands were sending jolts through me in my aroused condition. I wished that I had jerked off this morning but sadly I was running late and never had the chance. I took another sip of brandy to distract myself. This stuff was good, too good.

Nigel was now measuring my biceps which felt rather intimate as he nodded appreciatively and wrote the number in his notepad. After measuring my wrists, he stepped forward to wrap the measuring tape around my waist, bringing his face near my chest again as he passed the tape behind me. Despite having zero interest in guys, the intimacy of the fitting in my hypersensitive state was sending my mind in all kinds of erotic directions including how Grace likes to play with my chest and suck on my nipples. I needed to think of something else.

Meeting the tape back at my belly button, Nigel whistled, "So lean and trim on top of your muscles, Grace is a lucky woman." I lamely nodded thanks for the compliment as Nigel paused glancing down at the growing lump in my shorts. Oh shit, here we go. He's going to ask me why I have a hard-on and call me a pervert. Instead, he said, "I just remembered that I have a small gift for you now that I have your waist measurement," and walked back out to the main shop, returning with a package. "While I do like your shorts, these are much more suitable for wearing under a suit." Nigel was holding up what looked like a pair of silk boxers in a rich burgundy color. Grace was always after me to up my underwear game so I immediately liked the idea and pictured myself surprising her on our wedding night with these when it

finally

came time to undress.

"They'll look great, thanks Nigel!" as I reached for the shorts.

"My pleasure Henry. We should try them on while we're at it to make sure they fit. I have some other sizes if needed."

Try them on... now? The last thing I needed to do was take off my shorts with my dick semi-hard but the brandy was clouding my thinking and I couldn't think of any way out of it. "Uh, sure. Let me go change," preparing to walk to the rear of the space and use one of the change rooms.

"You can change here if you'd like. It's just you and me with the shop closed and you can leave them on for your fitting. I'll throw in a second pair as well so you'll have a new pair for your wedding."

"Yeah, okay. Thanks, that's great." Oh shit. It was one thing to be bulging your shorts but another thing to strip down and let your misbehaving dick loose. Turning partially away from Nigel, I took a deep breath and slipped off my ridiculous smiley shorts realizing belatedly with the mirrors that there really was no privacy in the fitting room. My thickening cock swung free as I quickly put both legs into the silk boxers and pulled them up covering up my meaty tool once again.

Enjoyed this story?

Rate it and discover more like it

You Might Also Like