This story is fictional and does not portray real events or real persons. All characters are 18 years or older.
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.
“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.
“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.
“There, much better. Don’t you agree? Let me check the fitting.”
I glanced up at my image in the mirror and fuck, they did look good! My gym workouts were definitely paying off and the fitting room lights highlighted my muscles still pumped from my earlier workout. Also, the silk felt amazing on my skin as it hugged my bubble butt caressed my thick shaft. Grace was going to go apeshit when she saw me in these. The shorts did very little to hide my swollen package with the cut head of my cock clearly visible pressed firmly against the delicate fabric.
Nigel was walking around me studiously checking the fit as he tugged at the hem below my ass cheeks, and tested the snugness of the waistband. “Hmm, they do seem a bit tight in the front but I’m assuming that this may not be your, ahem, normal state?” as he looked up at me over his glasses.
Busted. Shit. “Oh god, no! I’m so sorry Nigel. I don’t know what’s wrong with me. I feel like an idiot. Sorry.”
“Don’t be embarrassed Henry. It happens more frequently than you might think, often with wedding fittings strangely enough. It’s completely natural. Would I be amiss to ask if your beautiful fiancée has suggested you minimize intimate contact ahead of your big day?”
“Yes! That’s exactly it. How did you know? I don’t know why she’s doing this. It’s so frustrating, and obviously embarrassing as you can see.”
Nigel nodded his head in sympathy, “Believe it or not, I’ve run across the same scenario with a few grooms. I’ve never understood why young brides seem to feel the need to inflict abstinence on their fiancés ahead of the big day. It must be very stressful and frustrating for you but not to worry, we can work around it. Don’t give it another thought.”
Relieved by Nigel’s relaxed response, I replied, “Thank you Nigel. I’m hoping things calm down.” Happy that Nigel hadn’t freaked out, I realized I was feeling amazing with my muscles pumped and my head pleasantly baked from the combination of weed and brandy. Also, if I did say so myself, I looked hot as fuck in these purple silk shorts. While Nigel prepared to take more measurements, I looked over my muscular 6’3” frame in the mirror, along with the 9” slab of hard cock pressed against my shorts. I looked like I could be a stripper in the Magic Mike movie. Grace was damn lucky to be marrying a stud like me and she had a lot of nerve denying me sex. My body felt stoked and I couldn’t wait for Nigel to start measuring me again. I had to admit, it felt kind of good having this fastidious man fuss over me and praise my physique. At least someone was paying attention to me if Grace wasn’t going to.
Glancing at Nigel’s reflection in the mirror, I watched him kneel down in front of me and stretch his tape around my hips. I was glad he was cool about my hard-on given his face was inches from my crotch. Oh fuck, he was pulling the tape taunt and trapping my hard cock behind it while he overlapped the ends on my hip. That’s not helping Nigel! Wondering why it was taking him so long, I noticed in the mirror that his eyes were on my bulge instead of looking at the tape. Was Nigel checking me out? Finally, he made a note of my waist measurement in his pad and stood up to take a sip of brandy. Turning his back to me, I caught him in one of the mirrors reaching down to adjust himself. When he turned back to continue, I discretely checked out his crotch and noticed a sizeable bulge pressed down one pant leg. Nigel apparently preferred boxer shorts as well, and more interestingly, was rocking a decent sized semi. Nigel, you little devil.
I had assumed all along that Nigel was straight even if he was a bit of an English dandy. While I was relieved that he wasn’t upset about my erection, it now looked like he might be enjoying the show more than he was letting on despite his outward professionalism. Come to think of it, he had actually grabbed my cock earlier. I felt my tool pulse in excitement strangely thrilled by the possibility that I was arousing the sturdy little tailor. There was something hot about having someone lust after you. We all liked to have our egos stroked and while I had no interest in doing anything with another guy, it was kind of turning me on in my horny buzzed state.
Feeling reckless and uninhibited, I decided to loosen up and enjoy being half naked and admired in the privacy of the fitting room. If Nigel secretly got off on it, I’d mentally edge myself teasing the proper little tailor while he finished the fitting. Afterwards, I’d head home to watch some good porn and shoot a long overdue load. Shit, Nigel would probably do the same. I didn’t see the harm, especially given Grace’s forced abstinence.
With my hips measured, Nigel said he needed to capture my crotch rise and placed one end of the tape at the waist of my shorts in the back running the tape down my ass crack, across my taint, and back up my silk-covered bulge. Was this really a measurement? It seemed like the most personal measurement ever but as I felt him positioning the tape, it also felt kind of good pressing against my hard-on and sliding up my ass crack. Grace often ran her fingers up my taint and ass crack when she was blowing me and I wasn’t ashamed to admit that I liked it. She’d even occasionally tease my hole which almost always made me shoot a big load. Legit measurement or not, this felt great.
Nigel seemed to be struggling as he knelt in front of me, “You have a very muscular posterior so I want to be sure to get this measurement right otherwise the trousers may be too snug. In your current state, I’m worried that your equipment is pulling the tape too far away from your body. My measurement might be out several inches at this rate. Let me think… ” as he paused to consider.
Wanting to be helpful, and hoping to get the little guy all hot and bothered, I said, “Sorry about that Nigel, I guess I’m making this a lot more difficult for you. Um, what if I pulled my shorts down for a minute and pulled my equipment to the side? Then you could run the tape beside it and hopefully get a more accurate reading.”
Nigel looked up at me in surprise, “Really? Are you sure you wouldn’t mind? That might actually work but I don’t want to do anything to make you uncomfortable.”
“I’m fine with it. After all, it’s my fault you’re having this problem so I’m happy to help. Also, I think this brandy is starting to go to my head so I’m feeling super relaxed,” I grinned.
Nigel laughed at the brandy comment, “Thank you Henry, I really appreciate it. Let’s try that,” as he pulled his tape back and waited for me. Poor Nigel was about to get a face full of big ole dick. Slipping my hands under the waist of the shorts, I slid them down past my knees letting them drop to my feet. My previously restrained cock swung forward with the swollen head shiny with pre-cum. Nigel’s eyes widened in shock as he watched my cock lumber back and forth. Both my cock and low hanging balls were shaved as Grace preferred it that way. I loved the feeling as well and thought it made my sizeable cock look even bigger. Henry seemed to be trying to maintain his composure and not gawk at my dick as he knelt in front of me.
Taking pity on him, I wrapped my hand around my shaft and pulled it to the side, “Sorry about that Nigel, it almost got away from me for a second.” Nigel seemed to wake up from his trance and smiled at my lame joke before sitting up to reattempt the measurement. Placing one end of the tape at the top of my exposed ass, he held it in place with his palm resting on my smooth cheek, and reached under my crotch with his other hand to guide the tape down my crack, across my taint, passing beside my smooth cum-filled balls and up my groin to my waist. He was careful to make sure the tape wasn’t twisted and lay flat to my skin so he smoothed it with his hand as he pulled it through my crotch. I held my breath as his fingers slid along my crack, taint and past by balls loving the teasing sensation. Meanwhile, I was loosely holding my shaft out of his way but purposely leaving most of it visible if Nigel wanted to check me out on the sly. I could see a slight tremor in his hands as he tried to focus on the job at hand but I could still see his eyes wandering. I was dying to stroke my cock rather than just hold it but unfortunately, that would have to wait until I got home.
With a hint of regret in his voice, Nigel said, “All done. Thanks Henry, that worked.”
“No problem. I’m glad I could help,” as I bent down to pull the purple shorts back up leaving my cock trapped downwards on an angle with the head peeking out just beyond the hem of the shorts.
“I am sorry this is taking so long Henry, I appreciate your patience. How is your brandy?” Surprised that my glass was once again empty, I held it out while Nigel topped it up. His eyes seemed distracted by the partially exposed flared head of my cock as it strained downward. It looked like Nigel’s sizeable bulge had grown as well. He finished pouring and placed the bottle back on the shelf, turning back to me with his trusty tape.
Kneeling in front of me again, Nigel wrapped the measuring tape around one of my thighs, just below my ass and straining shaft. I could see a thread of pre-cum hanging from the tip mere inches from his face as he worked. Noticing this, Nigel commented, “I hope I’m not making this worse for you with the familiarity of my measurements.”
“No, it’s fine. I blame my fiancée.”
As the strand of pre-cum hung lower, Nigel said, “Let me get that for you,” as he grabbed a silk handkerchief from his vest pocket in one hand and the shaft of my cock through the silk shorts in the other and gently wiped the pre-cum soaked head dry. It felt good to have a firm hand holding my cock even if it wasn't Grace’s. “There,” he announced pleased with himself and placed the handkerchief back in his pocket while again reaching for his tape. I couldn’t imagine this was a service he provided most of his customers but I wasn’t complaining.
Placing the tape on my side of my hip, Nigel began to measure my out-seam muttering to himself as he made a note. He then placed the tape up near my taint with the back of his hand resting against my heavy balls through the silk fabric. I felt another pulse of pre-cum ooze from the tip of my hyperactive cock as he pulled the tape downward to my feet. Spotting a new strand of pre-cum dripping towards his hand, Nigel commented, “Oh dear,” as he reached once again for his handkerchief, this time pulling more of my dick below the bottom of my shorts and using one hand to coax forward any pre-cum from my dick hole. I closed my eyes and softly groaned unable to control myself.
“Just a couple more measurements Henry,” as he released my cock and stood, walking behind me to reach up and place the tape across the breadth of my shoulders. Given his height, he had to stand close to me to be able to reach my shoulders and still see the tape. I could feel his hard bulge wedged firmly between my thighs as he strained upwards. There was something about this polite little stud of a man pressing his big cock against me that was making me a little crazy. I couldn’t believe he wasn't aware of what he was doing and pushed my ass back slightly as he struggled to get the measurement. Poor Nigel seemed to be ruffled.
Taking a deep breath, Nigel said, “Last measurement,” as he placed the tape at the back of my neck. “Could I get you to help me with this one and hold this end in place?” I reached behind my neck and placed my finger over the tape end. “That’s it, thank you.” With the tape secured, Nigel was free to drape the tape down my spine and measure my back as he knelt behind me with one hand resting on my ass cheek. Clenching my ass, I heard a soft gasp as my hard glutes flexed. Standing up, Nigel looked flushed as he announced, “That’s all the measuring. Thank you again for your patience.” I noticed a hard ridge of cock trapped down Nigel’s pant leg as he held his notepad in front of him to hide the fact.
“Lastly, I just need to try on the partially made trousers and jacket to test the fit and put in a few pins. There’s more work to do on both garments but this along with your measurements will give me everything I need to finish up. Let me grab the suit.”
While Nigel walked back out to the showroom to get my suit, I took a sip of brandy and admired myself in the mirror. No wonder Nigel was at odds. My cock was still rigid as steel and I took the opportunity to jerk it a couple times in the mirror. Fuck, I was so horny. I couldn’t wait to get home and lube up my cock. Wanting to tease Nigel, I angled my cock downwards on more of an angle so that it was straining against the shiny fabric with 3-4 inches of hard shaft extending below my shorts. Oops, how did that happen? Smiling at my wickedness, I heard Nigel come back into the room with my suit.
I had to admit the suit was beautiful. It was still unfinished but I could tell it was going to be perfect for the wedding. As Nigel walked up to me, he noticed the shiny head of my cock extending below my shorts and struggled to form a sentence, “Ah… Henry, you may want to adjust that before you put on the trousers. We don’t want any accidents.”
Oh shit, right. It’s probably better not to have cum spots all over your wedding suit, at least until after the wedding. Playing innocent, I acted surprised at what my cock was doing and reached down my shorts to haul it back up, running the ridge of my tool upwards. “Sorry about that.”
“No worries. Let’s try on the trousers first.” I carefully stepped into the pants pulling them up to my waist. They seemed to fit well as Nigel knelt down and checked the fit, placing pins at various locations to help him with the remaining sewing. He was leaning towards me with a couple pins in his mouth while he worked. My cock was close to his arm as he pinned so I shifted slightly brushing my hard-on against him but trying to act like I was unaware. It seemed to momentarily startle Nigel before he gathered his wits and continued. This happened a few more times as he moved around me and I took the opportunity press my ass or cock against him when I could without being too obvious. I felt like Nigel was almost making it easy for me in the positions he put himself him. All of this teasing and light thrusting was keeping me rock hard.
Looking less groomed and polished from when I arrived, Nigel stood up and said, “Okay, let’s just do the same with the jacket and we’re almost done.” We repeated the same process with Nigel checking the fit and pinning where he needed to. He was reaching up higher and invariably had to stand close to me to do this. I continued to connect with him whenever I had the chance, pushing my cock against his torso and at one point nudging my thigh against his hard-on. Nigel looked like he was close to creaming his pants.
“Okay, we’re done with that. You can take off the jacket and trousers now.” Happy to remove the suit without getting any pre-cum on it, I handed both garments to Nigel while he hung them up. Turning back to me, Nigel said, “There’s one more thing I’d like to check with your shorts. We already talked about them being a bit snug, um, because of your troublesome arousal but I’m worried they might be too small regardless. You’re bound to be dancing and moving around at your wedding more than you normally would so it wouldn’t do if they’re too small. I know you’re probably eager to get out of here but would you mind humoring me and doing a few stretches just to make sure they’re not too small?”
I wasn’t totally sure what Nigel was asking me but I was happy to stay a bit longer to see what he had in store for me. “Sure Nigel, what would you like me to do?”
“Perfect. Thank you Henry. Let’s start easy and just have you bend at the waist and touch your toes, or reach as far forward as you’re comfortable with.” Despite my muscles, I was pretty flexible so happy to bend forward and easily touched my toes. “That’s impressive Henry, you’re very flexible. Hold on, I just want to check the seams to see if they’re stressed at all in this position.” With my silk-covered ass in the air, I could sense Nigel moving around behind me as he checked the seams of the shorts. It felt like Nigel was using the opportunity to feel up my ass as his hand ran across the fabric on the back of my shorts and ran his hand under the edge of the hem testing the snugness of the fit. I knew he was enjoying this so I thrust my ass higher and back into his palms. You want to play Nigel? I can play… to a point.
After far too much time, Nigel told me I could stand up again. “I wouldn’t mind trying one more stretch and then we’re done. I know you go to the gym regularly, can you do a squat for me? You likely won’t be doing any squats at your wedding but I feel it’s a good overall test.
“Sure, I never skip leg day Nigel. A squat it is…” Placing my arms straight ahead, I gently lowered myself into a squatting position with my muscular legs wide and my ass pointed backward until my ass was hovering just above my heels. “Is that good…?” Suddenly I heard a loud ripping noise as I felt my shorts tear open in the rear. I could no longer feel cloth covering my crack and wondered how much of my ass was actually exposed.
“Oh dear. That doesn’t sound good. Let me take a look.” I looked in the mirror to see Nigel attempting to crouch down and look under my ass to see what had happened. I could feel his hands sliding along under my silk-covered cheeks trying to find the tear until suddenly his fingertips were in direct contact with the bare skin of my crack and resting on my hole. Whoa, the direct intimate contact sent a jolt through me as I felt my tool ooze pre-cum from the head. Could Nigel not tell that he was touching my asshole? As Grace well knew, both my nipples and ass were hardwired to my cock. From the feel of Nigel’s hand on my ass, I had apparently torn open the back of the shorts. Nigel still seemed confused as to what had happened as he continued to feel along the edges of the tear and brushed against my hole yet again. I let out soft groan before I could control myself.
“Henry, it’s too awkward to see what’s going on in this position. Can I get you to lean against the chair so I can have a proper look? They’ve obviously torn but I want to see exactly how badly and where so we can make sure we get you a pair that will hold up.” Still recovering from Nigel’s intimate ass play, I nodded and walked over to a leather club chair, leaning over the back and bracing my palms against the top of the wide tufted leather arms. “That’s perfect, thanks. Let me see what’s going on,” as he crouched down behind me. I heard a soft, “Oh my…” as Nigel looked up at the back of my shorts.
“How bad is it?” I asked.
“Hold on, let me check.” I felt Nigel’s hands sliding along my silk encased cheeks as he explored my firm butt, moving closer to my crack. As he neared the tear, I could feel his fingertips once again connect with bare skin as he ran his hands up both sides of the tear. In this position, there could be no doubt that he knew what he was doing as he teasingly glided his fingers directly up and down my crack, delicately brushing my hole on each pass. I caught myself arching my ass backwards as I hunkered down on the top of the padded leather chair. Fuck.
“Hmm, it‘s not looking good but I just want to check a couple more things.” It felt like Nigel may have wet his thumb as he continued to softly tease my ass crack. I couldn’t see what this could possibly have to do with the tear but it felt kind of great. I could feel his other hand exploring my taint and the base of my balls at the same time.
While loving the sensations, I was worried where this was going and thought I should do something about it. “Uh Nigel, are you done? Can I get up?”
“Hold on Henry. I’m pretty sure I know what caused the rip. It might be a combination of fit and faulty fabric but I just need to do one more thing to confirm. Brace yourself.”
Brace yourself? Why?! What was he going to do? I felt Nigel’s hands sliding under the edges of the tear on both sides and grip the fabric of the shorts in his hands when suddenly he pulled hard, tearing the rip wide open and exposing my entire ass and freeing my shaft and heavy balls. I was crouched low against the chair gripping the arms in shock still trying to process what the fuck had just happened after Nigel’s sudden and surprising maneuver.
Calmly, I heard Nigel say, “Ah, that’s better. Now I can see what I’m working with,” as I felt his hand reach past my balls and firmly grip my hard cock in his powerful grip pulling it back until it was pointing backwards towards him. I needed to stop this, what the hell did Nigel think he was doing? Just as I was about to turn and protest, I felt something warm and wet wrap around my aching cock head. Ungh… Turning my head, I looked in the mirror’s reflection to see Nigel crouched down behind my raised ass with my rigid dick in his hand pointed back at his face while he slurped and sucked on my knob sliding my cock deeper down his throat. The normally reserved tailor was attacking my tool with a fervor, apparently tired of my teasing and deciding to assert himself. Stunned by his sudden personality shift but appreciating the level of his cock-sucking expertise, I put my protests on hold momentarily while leaning forward and settling my torso against the leather seat of the club chair angling my ass upwards and giving Nigel easier access to my dick. It felt so good to have someone finally give my swollen cock the attention it deserved. Nigel appeared to be making up for lost time as he slurped and lapped at the pre-cum oozing from my dick hole while slathering ever inch of my shaft with his talented tongue. His technique was completely different from Grace’s tentative approach which always felt like she was doing me a favor. With Nigel, there was no doubt that he was enjoying this as much as I was given his enthusiastic grunts.
That said, this was much more than some harmless teasing but damn it felt good to have someone else’s hand stroking my cock and Nigel was a master at it. “Fuck Nigel, what are you doing to me?”
Removing my cock from his mouth to speak, “Come on Henry, you’ve been asking for this all evening teasing me with your big swollen cock and thinking it would be fun to get the little Englishman aroused. You’ve been a naughty boy but don’t worry, Nigel is going to take good care of you and help you with your, ahem, problem,” as he popped my hard cock back into his mouth sliding it all the way down his throat until my balls brushed against his moustache. Moaning, I blamed the weed and brandy for letting this go as far as it had but I knew it had to stop. I wasn’t gay and had no interest in guys but I just needed to enjoy one more minute of Nigel’s sweet blowjob before I put an end to it… a mouth is a mouth, right? I pressed forward onto the wide arm of the chair supporting my upper body with my arms resting on the flat edge of the chair while Nigel unabashedly worked my angled tool, no longer concerned about anything related to actually tailoring. I was riding his talented mouth when I felt his thumb sliding up and down my puckered hole. Oh fuck.
Removing my cock from his mouth, Nigel aimed it downwards against the back of the leather club chair using spit and pre-cum as lube to stroke and tease it. He seemed determined to keep me on the edge while his other hand began to explore my ass by running circles around my pink hole with his thumb.
Settling low onto the chair with the smell of leather in my face, I felt something warm and wet poke at my ass. Nigel must have replaced his thumb with his tongue as I felt him lapping at my hole while his moustache brushed the sides of my cheeks. Nigel was eating my ass! While Grace had teased my ass with her hand and even fingered me once as I was shooting a load in her mouth, she had never rimmed me although I had always wondered what it would feel like. Now I knew and it felt fucking amazing as Nigel slurped at my crack and burrowed his thick tongue in my hole. I was moaning and riding the delicious sensation of having my ass rimmed while my cock was expertly stroked. I leaned further over the chair, dropping my torso onto the seat and pushing my ass back into his face trying to get more of his tongue in me as Nigel torpedoed my hole with his tongue over and over.
Loving what Nigel was doing to me, I no longer had any aspirations that I would be trying to stop this. I needed to get off and if it meant this was my first guy on guy experience, so be it. Taking a break from my ass, Nigel ran his tongue down along my taint and sucked at my shaved balls, pulling them into his mouth and sliding his tongue over the smooth skin. Lifting my cock up, he continued down to the tip suckling the end and swallowing any stray pre-cum before working his way back up to my ass.
I glanced over to the reflection in the mirror and was shocked to see my athletic frame looking so exposed and submissive draped over the club chair with my muscular pale ass pointed upwards and the fastidious tailor’s face buried deep between my cheeks. I realized I was completely naked other than the tattered remains of the silk shorts hanging from my waist while Nigel remained impeccably dressed although I noticed he had unzipped the fly in his trousers and hauled out what looked like a sizeable uncut cock and a large set of hairy balls. His dick looked to be about 8-9 inches in length, thick and dark. Watching Nigel’s shaft swing freely while he ate my ass made me suddenly realize how gay this situation was. I could no longer fool myself that I was having some harmless fun with the tailor, this was about as gay as it gets. As Nigel drove his tongue deeper lubricating and stretching my hole while edging my slippery cock in his hand, I pushed my ass into his face wanting more.
Nigel paused from his assault to stand up and move closer between my splayed legs. I was missing his tongue already but he reached down and continued to stroke my cock against the back of the chair, while massaging and stretching my wet hole with his thumb. He was prodding and pushing the tip in, teasing and stretching the rim while I held on. With the amount of spit from his previous assault, his thumb easily slipped in as I groaned and writhed below him. Glancing in the mirror, I could see Nigel gripping his rigid cock while dropping a strand of spit onto it and slathering up his shaft. While I loved what Nigel was doing to my ass, I was uncomfortable with where this was heading as he gripped my hips and started to slide his slippery tool along my spit-drenched crack. Spreading my muscular ass cheeks wider with his hands, the ridged head of his uncut cock was now gliding directly over my puckered hole teasing me with each pass. There was so much spit and pre-cum covering my ass and Nigel’s cock, it felt amazing as his slick cock humped me. In the mirror, I could see his foreskin sliding back on each thrust exposing the thick red head of his cock as he rode my crack. While I was loving this, I didn’t want the tailor to fuck me and started to lift myself up.
I felt Nigel immediately place his strong hands on my shoulders easing me gently back down as his cock pressed between my thick glutes. “Easy Henry, you’re doing fine. You know you want this and I can assure you, you’re going to love it,” as he ground his thick cock against me.
“But I’m not gay…” I weekly protested while at the same time meeting Nigel’s thrusts with my ass. I could feel pre-cum dripping from my own cock as it pressed against the leather back of the chair sliding against the slick surface.
“Ssh. Don’t worry about labels, just enjoy the rest of the fitting,” as he gripped my hips and hauled me back slightly so my asshole now rested at the perfect height to connect with the greasy head of his cock. I could feel the tip probing more insistently at my pink hole as he continued to slide up along my crack. It was so erotic to have my face buried in the leather seat of the chair not seeing or knowing what was coming next as Nigel teased me with his dick. As he pushed against my hole with his cock head, I tried to relax and suddenly the tip slipped in. Fuck, this was really happening! I glanced up in the mirror to see Nigel drop another strand of spit onto his poised and rigid cock head increasing the amount of lube as he withdrew slightly and eased back in. “Good job Henry. I know you’ve waited so long for this but we’re almost there.”
I couldn’t understood how my larger athletic frame had ended up under this shorter man’s control as the tip of his cock pushed deeper into my tight virgin hole but I did know that I wanted this. I needed Nigel’s big cock buried balls-deep in my ass. My prick throbbed with the mental image as I pushed my ass backwards popping his ridged cock head past my tight ring. Oomph. “Good boy...” While Nigel held still to give me time to adjust to his girth, I realized I was at the perfect height for him to control his thrusts as he slowly slid deeper, stretching my ass with his thick tool. My Dad’s proper English tailor was fucking me with his big uncut cock.
“Fuck, fuck, fuck…” I groaned as Nigel eased deeper.
“Oh I will Henry, I will indeed,” as Nigel eased back before sliding his rigid tool forward. I could feel his cock head pressing against a spot inside me that was sending jolts to my cock. Fuck, that felt amazing. Henry was being gentle but persistent as he’d ease back and slide deeper each time. I glanced to my side to see that the tailor seemed to be pressed almost all the way against my ass as he pulled back exposing his slippery shaft before sliding all the way in again. Nigel was balls-deep in my ass! I groaned as he pulled almost all the way out before sliding back in again. I could feel my cock throb with each thrust as I pumped a steady flow of pre-cum from the tip. The speed of his strokes was increasing as he established a steady rhythm riding me hard. I was impressed by his strength and stamina as the stocky tailor gripped my hips and drilled my hole like a piston while I groaned and held onto the chair. I never wanted this to end.
Nigel was slamming into me with my rigid cock trapped downwards against the edge of the leather-tufted chair. With each thrust, my cock would swing away from the chair back just to slap back against the wet leather as Nigel buried his cock in my hole. The constant pounding of his prick against what I assumed was my prostate and the slapping of my cock against the leather chair was bringing me close to orgasm. Was I actually going to cum from Nigel fucking me without even touching my cock? I was loving the feeling of having someone else in charge for a change and Nigel appeared to know what he was doing as he thrust powerfully into my hungry hole. He wasn’t even breathing heavy as the pounding continued and he held my ass in his muscular grip. As the speed of his assault increased, I sensed Nigel might be about to cum as I met him on each thrust loving the feel of his cock pounding my prostate and his heavy balls slapping against mine.
“How does that feel Henry? I want to make sure it’s a comfortable fit.”
“Fuck. Fuck me… Nigel. Fuck me hard.”
“I believe I can do that. Hold on.” I took Nigel at his word and gripped the arms of the club chair as he slammed his cock as deep as he could into my previously virgin hole. I could feel my aching cock slapping against the side of the chair as Nigel’s merciless pounding continued and the chair edged across the floor. Suddenly, Nigel roared as his thick cock began to blast his thick load deep within my hole. At the same moment, I felt my orgasm slam into me and my cock began to splatter cum down the side of the chair while my ass spasmed around Nigel’s meaty shaft. I could feel Nigel’s tool still shooting inside me as he continued to pound my ass. I couldn’t believe I had come without touching my cock but it was probably the best orgasm of my life as my dick continued to twitch and pump cum from the tip. Nigel was slowing down his thrusts but continued to bury his cock with each pump. As I tried to catch my breath, Nigel commented, “There you go. I told you I would take good care of you didn’t I Henry? You must feel a great relief.”
All I could do mumble incoherently in response still overcome by my orgasm as Nigel gently fucked my hole making sure every drop of his load filled my ass. Eventually pulling his cock free from my ass, I whimpered missing the feel of his thick girth. After a minute, Nigel appeared beside my head offering me a small towel to clean up with. For his part, he looked the same as when I had arrived with his thick tool stowed back in his pants and everything about him looking groomed and polished. As I grabbed the towel, he let me know there was a washroom behind the change rooms if I wanted to clean up.
Groaning and lifting myself from the chair, I gathered my clothing and stumbled to the washroom. Looking at my face in the bathroom mirror, I asked myself what had just happened. I was buzzed and a bit drunk but I also felt like I had been thoroughly fucked and my body ached although it was a pleasant ache. I could even feel my abused cock thickening up slightly as I recalled what had just happened. Giving myself a quick wipe, I put my street clothes back on and attempted to straighten my hair so it didn’t look like I had just had sex.
Walking back into the fitting room, I noticed the club chair had been cleaned up and there was no apparent sign of what had just taken place. Nigel was standing near the bar with his usual pleasant expression. “There you are Henry. I must thank you for your patience this evening. It was one of the longer fittings I’ve had in a while and I appreciate your cooperation. The good news is I have all I need and will have your suit ready for a final fitting next Friday. Would you be able to come in for another appointment near closing time? There are less distractions at that time of the day.”
Surprised by Nigel’s lack of acknowledgment of what had just taken place, I briefly wondered if I had imagined it but my asshole assured me otherwise. It felt pleasantly stretched and I could still feel Nigel’s thick load in me. “Uh, sure. Next Friday would be great. Same time?” as I put on my jacket and starting walking with Nigel through the showroom to the door.
Unlocking the front door, Nigel replied, “Same time would be perfect.” Reaching for my hand to shake, Nigel added, “It was an absolute pleasure to meet you Henry. I don’t think I’ve enjoyed a fitting as much since… hmm… you know it was probably the last time your father was in. Do say hello to him for me,” winking as he opened the door into the snowy night. As I stepped through the doorway, I belated absorbed what he had just said. My father? What was he saying?
Turning back to Nigel in the doorway to ask, he interrupted me before I could open my mouth. “I almost forgot. Here are the other pair of silk shorts I promised. Please try to take better care of these ones if you would. You know how I feel about naughty boys. Have a pleasant evening Henry and I look forward to seeing you next week.”
Taking the shorts from Nigel, he stepped back into the store and closed the door pulling down the blind before I could respond. I was left alone under the store light on the quiet dark snowy lane wondering what the fuck had just happened. Nigel and my father? Confused but feeling thoroughly sated, I trudged off into the night slipping the dark purple pair of shorts into my jacket pocket already thinking about whether I would wear them next week or something else. I wondered if Nigel would approve of a jockstrap or would he consider that naughty? Either way it seemed like a win-win. I smiled to myself and walked down the dark lane with the snow swirling around my feet looking forward to next week’s fitting. My Dad was right about one thing, “Nobody fits a suit like Nigel.”
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