The Tailor's New Shop Boy

"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" across his mostly-bare pectorals. A Chinese dragon was tattooed in a spiral down his bicep, along with a brightly inked koi swimming across his chest. Most summer days, he didn't wear anything more than a slinky singlet a few sizes too large. Baggy, slouchy tank tops, intended to show off as much of his musculature as possible, leaving his tattoos and furry nipples on full display.

And he tried his usual swagger, too, down the London sidewalk, swaying his broad shoulders in rhythm with his steps, but he knew that something seemed off. He hated dressing up, and he hated the fact that his father threatened to cut off his tuition if he didn't "straighten up" and get a job. So now the rough, beefy rugger found himself in front of the least likely place: a posh looking tailor's shop.

This was Phillip's second time here. For his first visit, the tailor had measured him carefully, and now, a week later, he was supposed to be fitted for his interview suit.

"I'd rather be drinking," muttered Philip as he pushed open the door.

The shop was small, but luxuriously outfitted. A crystal chandelier threw a warm and soft light to all corners of the space, dark floorboards accented rows of bespoke suits that hung from expensive-looking, realistic mannequins. In the centre of the room was an enormous circular glass table that was covered in hundreds of silk and satin ties, artfully arranged into a swirling pattern. In the back of the shop sat an enormous mahogany counter with a magnificent antique till sitting square in the middle. The counter was littered with various tape measures and other assorted tools that Phillip assumed the tailor used to craft his garments.

Once again, Phillip was struck by how ridiculous he must look in this pompous and snooty place. He was 6'3, broad shouldered and extremely physically imposing, but he visibly squirmed and cringed as he looked for the owner.

On his last visit, Mr Cummins, the tailor, had made Phillip as awkward and insecure as he'd ever felt in his life. He'd been chastised for his sloppy dress, his unkempt hair and his dismissive comments about having to wear a suit. "I'll make a gentleman out of you one way or another, boy" Mr Cummins had said ominously as Phillip left, sneering at the dandy older man.

From behind a thick velvet curtain that led into an unseen back room, Phillip heard Mr Cummins. "Is that you, young Phillip? Please lock the front door for me, you'll be the last customer of the day and I don't want anyone interrupting us..."

"Ah, yeah ok." Phillip replied.

"I'll be out in just a moment, just putting some last minute finishing touches on your suit. In the meantime, take off whatever horrible things you're wearing."

Phillip looked around but didn't see any obvious changing room.

"Ahhh... right here in the shop?"

"Yes, boy. Where else?!" Mr Cummins barked sternly.

"Whatever 'horrible things' you're wearing," Philip sneered to himself, mocking Mr Cummins. He didn't even want to be here and he had to just take these insults, Phillip grumbled to himself. Hell, only reason he was here was his father's threats.

In the back of the store next to the mahogany counter was a three-way mirror. Philip could see his nearly-shirtless body, muscles half-bared through his slinky tank top hanging off one shoulder. He stood next to a rack of neatly folded custom shirts, each one a crisp pastel shade, whilst he was wearing as little of a shirt as he could get away with. Same with the shelf of glossy dress shoes he lumbered past: polished leather, gleaming in the chandelier light, contrasting with his minimal flip flops hanging off the soles of his wide, practically bare feet.

Why was he suddenly in front of the three-way mirror? And why was he suddenly whisking his tiny little shirt off?

So docile all a sudden. So willing to go along. "Snap out of it," Philip muttered to himself, trying to huff out his beefy, tattooed pecs proudly as the back door opened.

Mr Cummins stepped into the room with a flourish and Phillips felt his heart rate quicken.

Mr Cummins stood nearly a full foot shorter than Phillip, with a slight frame and narrow shoulders. His hair was silver, short and disciplined, and dramatically parted at the side. He was handsome, in a debonair and suave kind of way... like a British aristocrat.

But it was what he was wearing that had set Phillip off. Mr Cummins was wearing an incredible dark navy suit, with a bold chalk stripe. Underneath he sported a crisp white French cuff shirt with a dramatic cut away collar - from which sprung a wonderfully thick lavender tie. Phillip looked down to see that Mr Cummins was wearing black patent leather whole cut oxfords, and he thought he could see sheer silk hosiery between the trouser cuff and the tongue of the gleaming shoes. Just like the last time he'd seen Mr Cummins dressed this way, Phillip was equal parts intimidated and curiously aroused. The sensation frightened him.

"I thought I said to remove all your clothing, young man."

Mr Cummins watched on in stoic silence as Phillip anxiously stepped out of his shorts and stood uncomfortably with his hands over his groin. Even though he was almost half again as big as Mr Cummins, Phillip had to admit to himself that he was intimidated. Worse than any rugby coach barking at him in the locker room, or from the side lines. Something about Mr Cummins—something about this slight, dapper man—Phillip's cock tented half-hard in his gym shorts and jock strap, just from the way the man's deep voice sounded—and all the weird moments he'd had in the past week thinking about this man's suits and ties.

Clearing his throat, Philip huffed out his bare pecs again, trying to look intimidating. "I thought you meant down to my underw—"

Unimpressed, Mr Cummins frowned. "I said ALL your clothing."

"B-b-but?"

"These pants I have made you are silk lined, boy." Said Mr Cummins lightly shaking a suit bag he held in his hands. "You won't need underwear."

Nervously, Phillip reached out and took the garment bag. Mr Cummins strode past Phillip to the front door and checked that it was locked.

"We won't be bothered, young man... now where were we?"

Phillip gulped. No excuses now: the store was locked, so he would have no choice but to finish undressing. All traces of his cockiness and bravado gone now. The half-erect shaft of his cock bobbed as he shyly shimmied out of his underwear and stepped out of his flip flops, his hands once again darting to his manhood to cover himself.

"Much better." There was a crooked grin on Mr Cummins' features, his eyes scanning Philip's figure up and down.

Maybe it was the fact that this man was dressed to the nines, and Philip was completely naked? Sure, seeing a guy's junk in the locker room was one thing, but this felt... vulnerable. Watching Mr Cummin's eyes in the three-way mirror, Philip could see that the tailor was eye fucking his ass. Wasn't the first guy to do that, of course, but something about Mr Cummins felt... different.

But the moment passed, and Mr Cummins turned his attention to the garment bag. Unzipping it, he pulled out a beautiful custom shirt. Fine white cotton with subtle pink stripes, contrasting white cuffs and a crisp cutaway collar. Without saying a word, the tailor held the shirt up to Philip's shoulders.

"Alright," thought Philip. "I guess it's the full monty now." His bare pecs deflating with a sigh, he lifted his hands from covering his crotch, leaving his slowly stiffening cock hanging on full display. As Philip put his arms in the sleeves, Mr Cummins pulled the shirt the rest of the way up to Philip's shoulders. The crisp cotton felt cool and stiff against Philip's naked nipples. The hem of the shirt tingled against Philip's erect shaft as he buttoned the shirt from the bottom up. Reluctant to commit all the way, he left the top two buttons undone. But he had to admit that he'd never worn something so comfortable or luxurious in his life. The shirt fit his beefy chest perfectly and artfully hugged his broad shoulders. Philip had to admit he liked the way the pink stripes accentuated the peaks of his biceps.

As Mr Cummins fixed some rose pearl cufflinks to Philip's cuffs, Philip's cock continued to slowly stiffen, the shaft starting to tent against his crisp new shirt. Just the tingle of that stiff fabric against his stiffening cock—he had to steady himself, trying not to drop the hint that he was quivering with pleasure. He'd never worn anything this fine in his life.

Mr Cummins pulled up a chair. "Sit down, please."

Philip kept his shirt tail tucked under his bum. Was he the first guy who had sat naked in this seat? Mr Cummins produced a pair of fine dress socks. Kneeling before Philip, the tailor stretched the socks over Philip's wide, hairy feet, lining up the toe and heel perfectly. As Mr Cummins stretched the hosiery further up, Philip noticed that these weren't like other socks he'd worn. They were... like pantyhose. Sheer, see-through. Fuckin weird girly-ass hosiery. Was this really supposed to be an interview outfit? The further Mr Philips stretched them, the more translucent they became with their fishnet pattern. Was this really something his dad would've wanted him wearing?

Then again, he kind of liked the way his rock hard calves looked through that see-through hosiery. By the time Mr Cummins finished stretching them on all the way, they were so sheer and shiny that it looked almost like Philip wasn't wearing any socks at all.

Mr Cummins produced another item, but this was one that Philip didn't recognize. They came in a small box, and they looked like elastic straps with buckles and clips. Before Philip could ask, Mr Cummins was already fastening the purple paisley elastic to the tops of Philip's socks, then buckling the straps to the tails of Philip's shirt, adjusting the buckles carefully.

"Stand back up," the tailor instructed. As Philip did so, he felt the elastic straps tug his shirt straight down, connecting his shirt to his socks. Mr Cummins made a few more adjustments, ensuring that the shirt stays were snug. "These shirt stays will keep your shirt tucked in and your socks pulled up."

Philip nodded, tucking his cock head back under his shirt tail.

Mr Cummins pulled the suit trousers off the hanger. Kneeling again, he held them down to Philip's ankles, allowing him to step into the cuffs. As the tailor stepped behind Philip to pull them up, Philip's cock went from aroused to rock hard. The charcoal grey pinstripe wool felt cool, velvety—fuck—fuckin erotic—every luxurious inch of it hugging his beefy calves and thick thighs, cushioning his ass and his balls in soft, tailored luxury—

Philip drew in a sharp breath. "Aw fuck."

"What was that, young man?"

Philip cleared his throat. "Uh, nothing, sir."

Mr Cummins smirked as he tugged the waistband into place. Because of the shirt stays, Philip's shirt looked perfectly crisp and tucked in, the cotton pulled taut against his thick pecs.

Next came the braces. These were also baby pink—Philip was beginning to like that colour all of a sudden—complimented his complexion, he thought—and he liked the way they looked over his chest, emphasizing the thickness of his pecs, the breadth of his shoulders, giving a flattering V silhouette to his torso. Philip didn't have to lift a finger. Reaching into the waistband of the luxurious suit trousers, Mr Cummins fastened each of the braces buttons before finally tucking Philip's cock back in—

Like electricity, the sensation of Mr Cummin's finger tucking his cock in. Another sharp intake of breath.

"Fuck!"

Nothing but a smirk from the tailor.

As Mr Cummins zipped Philip back up, Philip's cock engorged to full mast, pitching a mighty tent against the cool silk lining of these beautiful trousers. Closing his eyes, Philip steadied his breath, trying to control his arousal—fuck—fuckking—aw fuck—he felt his cock just throbbing with pleasure against the silky texture, with no underwear there to hold it back—

But Mr Cummins wasn't done yet. Producing a shoe box, Mr Cummins knelt in front of Philip again, removing cedar shoe trees from the shoes inside.

Philip had never seen footwear like this before. They looked like soft purple velvet—slippers, maybe? No, these were different. Slippers didn't have little satin bows on them. And slippers didn't look so... dainty. "What kind of shoes are those, sir?"

"Opera pumps, boy." Placing them in front of Philip's sheer socked feet, Mr Cummins smirked again. "They're all the rage in high fashion. They'll set you apart from the crowd."

"They look—" Philip swallowed back the word. He wanted to say 'girly', but the glare from Mr Cummins silenced him. With reluctance, the rugger lifted his big feet, his sheer socked toes sliding into the cushioned velvet lining of the purple pumps—his cock aching, aching—fuck, so fuckin luxurious. The cool, soft velvet against his toes, against the ball and finally the heel of his foot, cushioning his feet all around in pampered luxury. The low cut shoe barely cupped his arch, barely covered half of the top of his foot. Even with his trouser cuffs resting with a slight break, Philip could see an inch and a half of hosiery, so sheer against the dark wool that it looked nude. The purple velvet bows were a dandyish adornment.

"Stand up, boy." Returning to his feet, Mr Cummins retrieved another item from the garment bag.

Why did Philip find himself wanting to do more than just "stand up?" Why did Philip feel a twinge of anticipation with this man's every command? Phillip obeyed and once again his hands self-consciously fell over his groin, trying to hide the now obvious hard cock tenting those luxurious suit trousers—the cool silk lining tingling against his throbbing shaft.

"Why the f—" Philip cleared his throat, and finished the thought in his mind: why the fuck am I so turned on by this? Phillip gasped t what Mr Cummins produced next from the garment bag. It was a waist coat in the same material of his luxurious pants, but it was the satin lining that shocked him. It was pastel pink, matching his suspenders, and it was cool and slick to the touch.

"Put it on."

Philip heard himself saying "Yes sir."

A crooked smirk from the tailor: "Good boy."

Phillip shrugged his massive shoulders into the sleeve of the waistcoat and felt the satin lining fall against his shirt back. He awkwardly fumbled with the buttons as he did them all up.

Mr Cummins stepped back, nodding and admiring the fit of his sartorial creation. Then, suddenly, the tailor darted in, placing his hands on Philip's waist. He tutted disapprovingly. "A gentleman never does up the last button."

Philip felt a spike of nervousness. He couldn't stand the thought of displeasing this talented artist. With a gulp, the big rugger undid the button swiftly.

Mr Cummins never broke eye contact and Phillip wilted under the older man's stare. Once the button popped undone, Mr Cummins stood holding the waistcoat with the tips of his fingers. He rubbed the material together slowly. "This just might be my masterpiece, boy. But we're not done yet."

Mr Cummins fingers trailed lower, as he smoothed out the wrinkles in Phillip's pants. His delicate fingers brushed over the big lad's steel hard cock, and there could be no misunderstanding or hiding that Phillip was turned on now.

Mr Cummins however didn't acknowledge it, and it caused Phillip to second guess him. Was this dainty old dandy just doing what tailors do or was he a perve? Whatever the case, Phillip couldn't deny that he was wildly aroused.

"Two more pieces to go, so far everything seems to fit perfectly my boy."

"Yes, ah, thanks sir..." Phillip stammered.

Walking around behind Phillip, Mr Cummins fussed over the waistcoat and pulled out any creases he found. "Now we need a tie... I think something pink to match, and I do enjoy seeing a big butch boy like you wearing pink. Let's see . . ."

On the one hand, Philip wanted to ask whether pink was an appropriate colour to wear to an interview. He'd remembered all those talks his dad gave him about needing to make a good first impression as a powerful, strong, stoic type who could rise to the occasion and deliver a firm performance, but after the whole bit with the waistcoat button Philip wasn't so sure he should speak up. So he relaxed his beefy shoulders, cock twitching against the satin lining of his trousers. He could feel a bead of precum starting to ooze out of his rock hard head.

Walking over to a walk adorned with hundreds of expensive looking silk ties, Mr Cummins paused for a moment before reaching for a thick baby pink one. "This will do nicely."

Great, thought Philip. Baby pink with flowers on it. This was way more than he bargained for, so the big lad finally spoke up. "Mr Cummins I... ah... I think I only ordered a regular suit. I don't think the money my father gave me will cover a tie, or this vest..."

"Nonsense. I won't have you leaving this store looking anything other than your best. We'll find some way for you to earn this, don't worry."

"But sir my father said that this was for an interview and I don't think I've ever seen anyone wear something like—" As Philip was about to take a step towards Mr Cummins, he felt the soft velvet of the opera pump sliding halfway off his heel, the cool air brushing against his half exposed arch. Startled by how quickly the elegant purple shoe slid off his heel, he paused, shifting his weight from one foot to another, noticing how loose and soft these new shoes were, how comfortable. Better than flip flops. And something about them seemed so elegant, so effete, that they felt... cocky. Like he didn't care about pink or purple or silk or satin or bows, or what anyone else thought.

"Enjoying those shoes, boy?" Mr Cummins approached him with the tie.

"They're so... soft, sir."

"Why yes, my lad, they are. I thought you would appreciate luxurious footwear on those beautifully shaped feet of yours. Feet like a Roman statue, deserving of footwear that cushions and pampers the soles."

Philip had never heard someone say something out loud like that before. But that was exactly what Philip found himself thinking, in the locker room, or at the pool, or in his frat house where half the guys didn't even wear shoes or shirts when the weather got warm. Philip shifted his weight from one foot to the other, enjoying the way the soft velvet pumps slid off his heels with hardly the slightest effort, as though these were shoes invented to put his feet on display, invented to conceal them in a luxurious and erotic little peep show under his elegant suit. He noticed the veins and sinews of the top of his feet, made powerful through years of running, the tops of his feet displayed by these low cut shoes. Roman feet. He had no idea someone else thought of a guy's feet like that.

"Or for that matter the rest of your sculpted body," continued Mr Cummins, stepping behind the big rugger. "Such broad shoulders, and such a full, powerful chest. Herculean arms. A body like yours deserves clothing that flatters such a chiselled silhouette, don't you think?"

"Yes, sir," said Philip, feeling even more aroused when Mr Cummins reached his arms around his neck and started fastening up the last two buttons of his shirt. Both of these were on the collar band, and, when Mr Cummins did the very topmost one, Philip felt the stiff cotton closing around his neck, forcing his chin upright. The rest of his posture stiffened automatically, his back growing tall and proud while his shoulders relaxed, opening his chest. Like a soldier at ease. "I do think this suit looks good. I didn't men to come across as... ungrateful."