The Tailor's New Shop Boy

"I can understand your reluctance, my boy." Folding the sharp cutaway collar up, Mr Cummins was looping the silk around Philip's thick neck. "Have you ever tied a tie before?"

"My—" Licking his stubbled lips, Philip was finding it difficult to concentrate, what with his throbbing cock, and every inch of his body cushioned against the silken, velvety luxury of his clothing. "My dad taught me how to tie—once—it was—something called a double-in-hand, or—"

"A four-in-hand," corrected Mr Cummins. "Not surprising. It's the standard knot of university fellows. But not to worry. Both your tie and your tie knot will set you apart from the crowd. You're a large, mighty fellow, so you need a large, mighty knot to suit."

Philip watched as Mr Cummins looped and knotted the tie around his neck. Each pass of the silk made the loop more and more snug around his muscular neck, and he enjoyed the sound of the silk, the hiss of it as Mr Cummins passed each loop of the knot through itself, the lustre of the flowers stitched in baby blue and purple against the soft pink background that seemed to glow like velvet. Such an intricate design, so many layers of silk folded in on themselves, making the knot feel thicker, heftier, more substantial. A fist of silk growing against his throat.

"A double windsor knot," explained Mr Cummins, "is a mark of distinction. And these ties are designed with that style of knot in mind. Extra thickness allows for a wide, conical knot, whilst extra length allows the tie to rest in proportion to a tall fellow like you. The width of the blade will also look proportional with your broad chest. Don't you see?"

"Yes, sir," said Philip, obediently folding down his cutaway collar, admiring the knot at his neck. A thick, wide triangle up top, cinched to an hourglass dimple underneath, the drape of the silk catching the subdued light and looking alluring, lush. Like a thick, weighty leash that his master had just put around his neck.

Why did Philip think of this as a leash? Why did Philip want to think of this as a leash?

Resting his hands on Philip's broad shoulders, Mr Cummins smiled. "Now, cinch the knot snug against your neck. Make sure the dimple is centred."

"Yes sir," said Philip, noticing how his cock throbbed even harder with pleasure as his fingers pinched the thick, lustrous silk. He wanted to stroke the dimple, to feel the knot growing tighter against his neck, the cool velvety silk against his fingertips.

Walking around to the front of him, Mr Cummins produced a tie bar, which he fixed just under the point where the lapels of the luxurious waistcoat met. Tugging the tie slightly, Mr Cummins made the silk arch forward, puffing out of the waistcoat, putting the pink floral tie on full display. "There you go. That's much more like it."

Philip puffed his chest out proudly, admiring the way the silk emphasized his physique, as though all those years of chest days at the gym were meant to display this exquisite tie. His whole body felt like a pedestal for this work of sartorial art. He was so transfixed with the tie—trying so hard to resist the urge to reach into his trousers and stroke his desperate cock—that he hardly noticed when Mr Cummins slid the suit jacket up his arms, onto his shoulders, tugging it here and there to ensure the optimal drape, tucking a purple paisley pocket square into the breast pocket, draping and tufting it to perfection, then finally doing the second button of the fine suit jacket to produce that ideal V silhouette.

Stepping back, Mr Cummins scanned Philip up and down, nodding. "Yes, I think this will do, young man. Now, let's look at you in the mirror."

Turning to face a full length mirror, Phillip gasped as he caught sight of himself. He was a vision of pure, dandified splendour. The suit contoured to his body exquisitely, enhancing his musculature while giving him an unearned air of dignity and sophistication. Phillip straightened his tie—it felt like the right thing to do, after all—and tightened it against his neck, tighter—no, even tighter—enjoying the way the thick silk knot felt against his neck, nearly to the point of constricting his breath. Yeah, good and snug, just like that. What was it about that sensation of silk tightening around his neck, the sharpness of that crisp collar constricting him? Seeing himself dressed like this awoke something deep and repressed in the boy he knew then and there that his life was forever changed. This is how a man is supposed to dress.

Mr Cummins stood behind him, resting his dainty hands on Phillip's shoulders. "Do you like what you see, boy?" He whispered huskily in Phillip's ear.

"Yes, sir." Phillip's voice was low, his eyes fixed on the mirror as he studied the way this garment flattered and enhanced his body. "It looks amazing. This feels so good."

"Indeed... this is the way I like my boys to dress."

"Thank you for this, sir... I ah..." The silk knot bit into Phil's neck as he swallowed. "I don't know how to thank you."

"I have some ideas..."

Phillip turned slowly to face him, gazing down at the smaller, older man. Tented in silk, Philip's cock tingled with pleasure, and his brain piqued with intrigue.

Mr Cummins' eyes returned the gaze. "I dare say you've got some ideas too, judging by how hard your cock is in those pants."

Oh, fuck. He'd noticed. Phillip stammered. "S-s-sorry sir, I don't know why it's ah - reacting like that."

There was a sound of a zipper opening slowly. "It's not the only one..."

Phillip looked down and with a start realised that the old man had his naked cock out and was rubbing it slowly.

Phillip's mouth dropped open—was it surprise? Shock? Lust? Why did his knees buckle? Why did he have this sudden urge to sink to his knees?

"It's alright," cooed the older man, stroking as he gazed up into Phillip's eyes. "Our admiration of fine clothing is mutual, it seems, so why not explore that?"

"I've hardly ever worn anything like this—nothing besides shorts and flip flops." Shifting his feet in the velvet-lined opera pumps, Phillip became aware of how dainty, soft, and elegant the velvet cushioning of these shoes felt against his toes, how erotic that silky sheer sock felt around his arches and heels. Every inch of his body cushioned in luxurious fabrics, his skin caressed with cool silk, smooth wool, and crisp cotton.

Philip felt his thumb brushing against his cock, which continued to throb against the silk lining of his trousers. "It makes me feel... cocky."

Mr Cummins watched him greedily from below. "Cocky as in confident, or cocky as in hungry?"

"Yes... both" Phillip stared at the older man's bare shaft. He felt his tongue licking his stubbled lips. His knees grew soft, sheer socked heels slipping out of his opera pumps as he sank to the floor, his eyes now level with the older man's phallus. Phillip ached to give worship to it. It felt like the new most important thing in his life. This is what he wanted, this is where he belonged... dressed to the nines like a dandy boy, with a cock in his face.

"Yes, sir," said the big, powerful rugger, now kneeling before the tailor. "Please may I?"

"Good boy, you may." Mr Cummins purred as Phillip opened his mouth wider and for the first time in his life, let a cock slip between his lips.

As his lips closed around the old man's cock, Phillip's mind raced with one single clear thought, 'I am a cocksucker'. His old life was just a lie in the face of this new truth. No longer was he the rugby jock in flip flops. Now he was a dandy cock sucking slut for older men.

Closing his eyes, Phillip began slowly moving his lips up and down Mr Cummins beautiful rod as the older man moaned audibly. He savoured the musky taste of the man as his hands came up to rest on Mr Cummins waist coat. His hands explored the folds of the older man's immaculate formal wear even as his tongue explored the surface ridges of the cock in his mouth. Sighing in ecstasy, Phillip couldn't believe that not only was he sucking his first cock, but he loved it. Mr Cummins' slim and effeminate fingers buried themselves in Phillips' hair, guiding the boy to take his cock further and further down, encouraging him softly to increase his pace or slow down.

"That's it boy, take sir's cock." Mr Cummins moaned. "I knew you were a secret little gay boy under that rough facade. A cock hungry little slut ready to suck daddy cock. You love sucking cock all dressed up, don't you boy? Say it." Mr Cummins' dirty talk thrilled Phillip and made his cock strain against his pants.

"I love it" Phillip moaned, barely able to enunciate with a mouthful of cock.

"Mmmm, yes." The older man closed his eyes, tossing his head back and letting his body sway. Burying one of his hands on the back of Phillip's head, Mr Cummins guided the younger man back and forth, never letting his cock slip from Phillip's mouth. "That's what I wanted to hear, boy."

Phillip tasted it, exploring it with his tongue, his muscular body rocking back and forth, heels popping further and further out of the velvet confines of his opera pumps. Maybe it was all those times in sweaty locker rooms with other musclebound guys? He thought he was checking out their gains, but this was different. Or maybe it was the same? Was he really looking at their biceps, or their chests, or was it their dicks? It wasn't that it made him feel like more of a man, having one in his mouth, but it made him feel more like... him, somehow. Like this was what he'd been looking for. Something about this—these smells, these textures—he'd never felt this buzz of pleasure before—

"Mmm, enjoying yourself, boy?"

"Mmmphf," Phillip nodded, his lips gliding up and down the shaft, his knuckles resting on the carpeted floor, like a rutting dog. The vents of his suit jacket were draped all over his beefy thighs. He relented for a moment, letting the moist cock head dribble down his lips. "Yes, yes sir."

"I can tell. You were born to be a cock sucker, my boy."

As he sucked and slurped on the older man's cock, Phillip's tie—phallic silk tie knot jutting out of his stiff collar—flopped forward out of his waistcoat and tumbled down his chest. Mr Cummins saw it, but instead of fixing it he wrapped the luxurious silk around the shaft of his own cock, effectively attaching Phillip to himself.

"Jerk my cock with your tie while you worship that dick, boy."

Never taking his mouth off his prize, sliding back and tonguing the head—amazing how often Phillip had caught glimpses of guys sucking each other off in the locker rooms, not a difficult technique to learn—Phillip moved his hand to the tie wrapped around the base of Mr Cummin's cock. In a slow and sensual rhythm, Phillip began stroking and sucking, the decadent silk of his tie contrasting with the warm and wet confines of his mouth and tongue.

So this must be what it was like, thought Phillip as he rubbed and sucked. All the gay pornos he'd sneaked and jacked off to—still "straight," of course—sucking another guy's cock in real life, finally, now that he'd been fantasizing about it for years.

Mr Cummins moaned loud and long in a stage of pure ecstasy as Phillip worked his cock. "You do that so well for a first timer, you're a natural cock sucker. I might just have to keep you around, boy."

Finally letting the cock slip from his mouth with a wet plop, Phillip looked up nervously into Mr Cummin's eyes. "I'd love that sir. But please sir, it needs to be a secret."

"No one needs to know, boy. But if you're going to be mine, you'll need a lot of instruction on the proper way to pleasure me..."

To demonstrate his willingness, Phillip leaned forward and took the cock back onto his tongue, giving it a long lick. Never breaking eye contact he murmured, "Please, sir."

Mr Cummins took Phillip's head in his hands and absentmindedly began fucking the big boy's mouth. He continued "We'll need to think of a good excuse to have you around here so often, won't we boy."

"Mmmmmf" Phillip mumbled in agreement.

"I could use a new shop boy I suppose." Mr Cummins pushed his cock down the boy's throat and held it deep. Phillip spluttered but forced himself to relax. "Would you like to work for me, boy? Be my dandy assistant? I'd dress you up like this every day."

Backing off the cock firmly lodged down his throat, Phillip gagged but nodded, relishing every last sensation of that beautiful silk lining against his throbbing cock, his balls cushioned by pure luxury in his trousers, the crispness of the shirt against his nipples, the stiffness of his collar cinched by that velvety phallic jutting tie that brushed against his chin. "Yes sir!"

"There's one more thing you need to do to prove you'll be a good addition to my business boy. You'll need to let me fuck you."

Phillip was shocked, just a short while ago he'd come in here a scruffy cocky jock. Now here he was, on his knees dressed to the nines like a dandy executive, having just sucked his first cock, and now he was entertaining the idea of being fucked in the ass.

"I - ah... will it hurt?" Phillip stammered nervously.

"Not one bit, my boy." Mr Cummins produced a condom, crinkling the shiny wrapper. "For this first time, we'll go easy. Maybe later, after you've been working for me a month or two, we'll try it without the rubber. But, for now—" a crooked smile, "I'll use so much lube you'll be begging for it."

Phillip hesitated. Sure, he'd seen this sort of thing before, heard a few fellow ruggers brag about ploughing someone up the ass. But this felt... different. He'd never imagined himself on the receiving end of it before. But at the same time he found himself... intrigued. After all, wouldn't he know more, if he felt both the giving and the receiving of it? What kinky, twisted new sexual horizons lay in store?

So Phillip, growing hard as his fingers absently stroked the dimple of his tie, finally nodded. "Then yes, please sir, fuck my ass!"

Again, the crooked smile, as Mr Cummins worked the rubber around his stiff cock. "Good boy. Turn over."

All traces of dignity gone now, Phillip rolled over onto his knees. There was some difficulty in unbuttoning the braces around his waistband, but he finally shimmied down his pants, exposing his beefy, hairy thighs, his beautifully sculpted ass. The velvet-lined opera pumps nearly fell off his sheer socked feet as Mr Cummins pulled his trousers off the rest of the way, revealing his powerful calves barely concealed by the sheer hosiery, accentuated by the elastic "Y" of his shirt stays keeping his shirt tails stretched in place. There was something erotic about all these layers, something that tantalized and stimulated Phillip even more, knowing that he was so fully strapped into a garment that only Mr Cummins knew how to undo.

Mr Cummins kept the lube in a small side table where all of his measuring tapes and custom ordering forms lay neatly stacked, as though the tube was just another tool of his trade. Squeezing out a gob, he greased his cock. "Are you ready, boy?"

Phillip lifted his knees, his opera pumps slipping off his heels without even the slightest bit of pressure, just barely hanging off his sheer socked toes. "Yes. Yes, sir."

"Then let's begin." Mr Cummins approached the muscular young man, throwing his knees over his slim shoulders.

Phillip stroked his cock, nervous, trying to steady his breath and relax as he felt the cool, moist tip of Mr Cummins' cock head between his cheeks. The lube allowed the old tailor to push right in, Phillip's body opening up around the cock head, gliding slowly in millimetre by millimetre. Phillip kept stroking, kept working his cock, his breaths becoming faster as he felt pleasure throughout his body, slowly letting Mr Cummins cock further, further in. With a plop, the whole head entered, Phillip's body closing in around it. And then further still, as Phillip's hands rubbed and worked his cock, his stiff French cuffs and gleaming cufflinks brushing against his balls, toes relaxing as his opera pumps started sliding further and further off his heels.

Phillip let out a long and primal groan as he felt his inner most sanctum being filled with cock. There was a mild pain, but it was not unbearable and as Mr Cummins held still inside him, Phillip found it faded away and was replaced by an indescribable pleasure. It spread through his entire body, as if every nerve was aware and excited by the cock deep inside his ass.

Phillips' eyes rolled and he moaned as Mr Cummins pulled almost all the way out before slowly, ever so slowly thrusting back in to the hilt again.

"How does that feel, boy?"

Phillip forced his eyes through an overwhelming feeling of pure bliss. Pushed by the force of the older man's thrusting, Phillip felt his velvet-lined opera pumps beginning to slide further down his heels, the silky hosiery exacerbating every last tingle of pleasure, yet another layer of luxury in this whole experience. Why on earth would he wear any other shoes again? These opera pumps felt ecstatic, soft and luxurious. He never thought shoes could make him horny this way. Barely able to speak, his voice filled with husky lust— "In... incredible, sir . . ."

Mr Cummins smiled wickedly. "Good boy."

Taking Phillip's muscular thighs in hand, Mr Cummins began a slow rhythm of thrusting into the younger man's tight fuck hole. In and out his cock slid as he made love to his newest acquisition while all the while Phillip moaned and squealed in delighted ecstasy.

At some point, Mr Cummins paused his thrusting and leaned down to kiss Phillip. Phillip opened his mouth eagerly and felt the older man's tongue slide against his own. Lost in the embrace, Phillip's arms wrapped around his new lover, biceps bulging in his crisp shirt sleeves, pulling the older man closer and willing his cock to new depths inside him. In response, Mr Cummins began thrusting again, harder now while still hungrily kissing Phillip.

"You're mine now, boy." Mr Cummins whispered into Phillip's ear between wet kisses and hard thrusts. "I'm going to make love to your tight little ass every day now."

"Fuck yes, Sir," grunted the jock. "Oh fuck—fuck me—oh fuck—I want it so badly—fuck—fuccccck" Phillip moaned in reply into Mr Cummin's mouth before sucking his tongue again.

The room was filled with wild sounds. Grunting and groaning, the rustling of expensive formal wear against Phillip's muscular body, silken seams straining as the pressure intensified. Phillip felt pleasure tingling throughout his body as his cock rubbed between his waistcoat and that of Mr Cummins, silk and satin and wool brushing against his sensitive cock head simulating being jerked off. Better than being jerked off. Luxurious and decadent, more sensual than anything Phillip could have imagined.

Phillip pawed at his tie knot, his thick chest swelling beneath his layers of finery. "Fuck, fuck, fuck! Sir you're going to make me cum!"

Phillip let his muscular body splay open. His sheer socked feet relaxed, the silky hosiery offering no resistance as his velvet lined opera pumps slid off the arches of his feet, dangling and flopping precariously off. Gone now was the cocky alpha male jock, replaced with a subservient sex toy and slut for Mr Cummins.

"Me too, BOY." In a wild crescendo of fucking and kissing, a roar bellowed out of the tiny older man. Mr Cummins howled with pleasure and thrust forward powerfully, his head flipping back and his eyes looking to the ceiling. "I'M CUMMING!!"

Phillip felt the cock inside his ass swell and pulse as Mr Cummins filled the condom with what Phillip was sure was an enormous load of hot man cum. Thinking about the fact this beautifully dressed older man has just fucked and cum inside him—every last tingle of pleasure from those beautiful, soft, luxurious textures of clothing—the strange journey from cocky jock to cocksucker—oh fuck—it was too much—Phillip kept pawing at that massive tie knot around his neck, and felt his knuckle brush against the dimple beneath that powerful fist of silk—fuck—felt so fucking good—he felt it—it was coming—he was cumming—his cock erupted.