A Dandy Boy’s Awakening

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Authored by Thomas Stevenson and Southern Suitor.


“Are those new shoes?” It was the man Tommy always noticed at the bus stop. The one who always had his tie in an immaculate double windsor, a gleaming fist of silk around his neck, sharp lapels and waistcoat, crisp French cuffs and cufflinks with gleaming patent leather shoes like angular black mirrors on his feet. Always immaculate in 3-piece suits. And today he was wearing a beautiful long camel hair coat over it all, along with his derby and umbrella.

“Yes, sir.” Tommy gulped, blushing a bit. The rain spattered all over Tommy’s glossy black wingtips. “I just got them yesterday.”

“Well done, lad,” remarked the well-dressed man.

That was always the extent of their conversations. Tommy would wait at the bus stop. He could time his watch by it, the arrival of this well-dressed passenger every morning. An inspiration. Tommy always had a thing for suits, and now that he was just out in the world–out of high school, taking a gap year before college–he was just beginning to take his wardrobe seriously. Granted, he had to keep alternating between his only two suits and multiple shirts and ties, but at least he had a second pair of shoes now.

Even though he was similarly dressed in a suit and tie, Tommy felt woefully inadequate standing next to this man. He was clearly a superior dresser and Tommy was convinced he’d never seen him wearing the same suit twice.

“You’re becoming quite the dapper dresser…”

Tommy looked up from his shoes and saw the man admiring him. It was far beyond just a casual bit of admiration, the man was eyeing him up and down, pausing suggestively when his eyes landed on Tommy’s crotch. Tommy was unnerved by this, but subconsciously he loved the attention from this older sartorial master. “I’d love to see you in a three-piece like me some day… I think you’d look quite dandy. Now I think it’s time we properly introduced ourselves,” he said as he stretched out his hand for Tommy to shake. “I’m Gerald Simmons, but since I’m much, much older than you, you can call me Mr Simmons.”

Tommy took his hand. “Tommy.” Mr Simmons held the shake for much longer than was customary while almost smirking… Tommy was confused. Was Mr Simmons interested in him? What was going on?

“I suppose I should call you Mr Tommy, then?”

“Uh, no sir. Tom Smith. Call me Mr Smith, uh, please.”

“Mr Smith, then.” Mr Simmons was still holding the handshake.

Tommy’s hand quivered. He tried to squeeze his fingers to make the handshake firmer, the way his high school teachers told him that businessmen were supposed to do. He could feel the buttery soft leather of Mr Simmons’ calfskin gloves, and his eyes were glued nervously to the perfect mirror shine of the older man’s patent shoes, beaded with water.

Even Mr Simmons’ smile felt dapper, somehow. He finally let go. “Well, Mr Smith, it’s grand to see a young man like you taking his appearance seriously. Good day.”

“Th–thank you, uh, sir.”

And that was the first conversation Tommy ever had with the elegantly dressed Mr Simmons.

A few months passed. Every morning, Mr Simmons would show up at the bus stop in his finery. Sometimes a camel hair overcoat, or a black topcoat. Sometimes gloves and an umbrella. Always a hat, always a three-piece suit underneath, always a mighty double windsor knot at his neck, always patent lace ups shined like mirrors. Mr Simmons would nod at Tommy and smile, giving a polite greeting each day as Tommy switched back and forth between his same two suits, saving up for his next purchase.

But it was nerve racking, the way Mr Simmons seemed to suggestively leer at Tommy’s groin. Always with a knowing smile on his face.

Tommy had to admit that Mr Simmons was beginning to enter his fantasies. Tommy was definitely interested in men, but this was the first time he found himself strangely attracted to a much older man. His impeccable sartorial choices definitely played a big part in it, indeed Tommy had always been drawn to powerful men in suit and tie.

Late at night, Tommy had begun imagining being seduced by Mr Simmons… he wished the older gent would just grab him by the tie and pull him into a kiss. Tommy wondered what it would feel like to be pressed against Mr Simmons, to feel his hardness pressed against his own. Even just thinking about that was enough to get Tommy rock hard, jerking and gushing ropes of warm and guilty boy cum.

It was fresh from one of these nocturnal activities that Tommy found himself once again at the bus stop with Mr Simmons. This particular morning it was pouring rain and both men huddled close under the protective awning. The bus was absurdly late for some reason and Tommy was getting increasingly anxious that he’d miss his connecting train. Mr Simmons was agitated as well, and muttered something under his breath.

Tommy checked his watch periodically… at 30 minutes past the scheduled pick up time güvenilir bahis he’d officially missed his train.

“Seems like we’ve been abandoned by the bus driver today, Mr Smith.”

Mr Simmons saying his name was like electricity to Tommy. “Yes sir, it does.”

“Well I’m officially too late for my morning meetings, so I guess I’ll work from home. What about you, Mr Smith? Do you have anywhere to be?”

“I think I’ll be too late for my shift, so I’ll probably call in sick” said Tommy.

“Interesting… two men with no obligations. All suited up and no place to be.” Mr Simmons had that familiar sly smile on his face now.

That was a sly smile, right? Tommy shifted his weight nervously. Looking down, he could see that, despite his best efforts, his shoes weren’t nearly as shiny as Mr Simmons. Or as well crafted. Something about the angle of the toes was off, whereas Mr Simmons’ shoes looked perfectly sharp, like a pair of pointed black chisels shining under the perfect break of his pinstripe trousers.

“You fancy a pint?” Again, Mr Simmons gave Tommy a sly gleam. And was he staring at Tommy’s crotch? “A bit early for a drink, but we might as well make the most of it.”

“I–uh–I think that would be, uh, nice?” Tommy ran a finger along the inside of his collar.

“Come along then. It’ll be my treat for a handsome lad like you.”

“I, uh–” but before Tommy could form another word, Mr Simmons was already strolling away, glancing over his shoulder at the younger man, crisp leather soles of his dress shoes clicking on the pavement. Finally, Tommy bounded down the street to catch up. “Didn’t you say you had to work from home?”

“I do,” said Mr Simmons without breaking step. “But it can wait. Besides, there’s no use standing out in this weather.”

“True,” said Tommy. He licked his lips, trying to keep up with Mr Simmons. He wanted to say something else, but he couldn’t make himself say it. How the very sight of this man’s elegant outfits made his cock twitch. How he stayed up at night fantasizing about him. But none of that. Tommy couldn’t say any of that. Yet he could at least have a drink with the older fellow, right?

They went into the pub, and Tommy’s nerves only grew more agitated. He saw Mr Simmons shuck off his beautiful overcoat, and the glossy navy satin lining inside of each sleeve, revealing an immaculate navy pinstripe three-piece suit. Sharp lapels both on the suit jacket and the waistcoat, with a delicate pink floral tie blossoming out of the waistcoat like the plumage of some exotic bird. A decadent pink silk pocket square spilled out of his breast pocket, and, as he shook off his umbrella, he sent more droplets of rain splattering all over his dark, mirror polished shoes.

Tommy sat down in a quiet booth while Mr Simmons went to the bar to order drinks. He looked over and admired the man he’d grown secretly enamoured with. He couldn’t believe they were about to have a drink together! Quickly Tommy sent a text to his boss complaining of a migraine and then put his phone away, effectively letting himself off the hook for any professional responsibilities.

In no time, Mr Simmons returned with two pints of beer. He sat down and pushed a glass to Tommy. Tommy reached out and took it, their fingers touching for the briefest of moments.

“I’m glad we’re finally getting the chance to get to know each other, young Mr Smith. It’s not every day I get the pleasure of a drink with a handsome young lad who so clearly aspires to dress like a dandy!”

“Thank you, Mr Simmons.” Said Tommy. “And thank you for the drink.”

Over the course of the next two hours the drinks were free-flowing and so was the conversation. Tommy was slowly letting his guard down and getting comfortable in the presence of this man who has previously made him feel so nervous. What hadn’t diminished though was his powerful attraction to Mr Simmons. Tommy wanted so desperately to touch the gentleman sitting across from him. To run his hands all over that pink satin tie and feel Mr Simmons hands on his tie in return while he leaned in and kissed him.

And so it came as a very welcome surprise that when Mr Simmons returned from the bar with another drink, he sat down on the same side of the booth as Tommy and rested his hand on Tommy’s suit pants just above his knee.

“I’ve been thinking, and what you need is a mentor,” said Mr Simmons, squeezing Tommy’s knee, then patting it, then resting his hand again on it. Tommy could see the crisp white French cuff that contrasted with the delicate blue stripes of the rest of Mr Simmons’ shirt, the functioning button cuffs of his pinstripe jacket–custom-made, Tommy thought–and Mr Simmons’ glittering cufflink. “Someone to . . .” Mr Simmons gestured vaguely for a moment, searching for a word, “to guide you, on your formal journey.”

“Oh?” Feeling the buzz of beer, Tommy dragged the pint glass closer, relaxing his knee ever so slightly in Mr Simmons’ direction. “I mean, türkçe bahis I’ve been trying very hard to save up, sir, and buy my next–“

“A tie, perhaps?” Again, the sly smile as Mr Simmons squeezed Tommy’s knee, sliding his fingers ever so slightly up the younger man’s thigh, rubbing the smooth suit fabric. “I noticed that you take a particular pride in those. You’ve mentioned them a few times just today. And not just anybody ties a double windsor like that.”

“I, uh, yes sir, I’ve been trying to expand my tie collection.” Head swimming from the beer–and from animal lust–Tommy’s cock twitched at the sensation of the older man’s fingers caressing the suit fabric inside his thigh. He let his knee rest against Mr Simmons’ knee, thighs full spread to reveal his hard-on. After all, Tommy noticed that Mr Simmons’ eyes were resting there anyway. “I mean, my collection is nothing like yours, I’m sure, but I think I’m getting there.”

“Well young man, as we’ve established, we are two well-dressed gents with nowhere to go.” Mr Simmons’ hand was fully above Tommy’s knee now, squeezing his thigh. “If you fancy a visit, I’d be glad to show you my full collection. You could pick one to try out tomorrow.”

“Oh, you ah… want me to come to your place?” Tommy said, almost whispering. “It’s just around the corner, I think you’ll find it to your liking, and we will be able to discuss and do whatever we like without prying eyes. Maybe you’ll find some suited inspiration in my wardrobe.”

Without another word they left the establishment. Sheltering from the miserable weather under their umbrellas, the walk was only a few hundred meters but it seemed to last forever. Tommy couldn’t believe this was happening! Here he was half drunk and about to visit the house of the man who he had jerked off over countless times. And if the hand on the leg was any indication to go by, Mr Simmons was absolutely coming onto him.

“We’re here.” Said Mr Simmons. Tommy looked up and took in the sight of his companion’s home. An enormous Victorian estate home completely surrounded by large pine trees. It was an old heritage property and clearly the nicest and largest on the street. As they walked in through the front garden and onto the front porch, Tommy realised his suspicions about Mr Simmons were true. He had to be fabulously wealthy to be able to afford a house like this.

This opinion only solidified as they entered the home. It was magnificent, with polished wooden floor boards and everywhere he looked there was expensive art hung tastefully on the walls. Mr Simmons led Tommy into his living room and went to the fireplace to light a fire. Tommy turned his back on him and continued soaking in the opulence of the home he was in. He couldn’t remember ever having been somewhere nicer.

Suddenly, Mr Simmons was behind him. His hands on Tommy’s shoulders and his breath on the nape of his neck.

Mr Simmons bent over to whisper into Tommy’s ear. “I’ve been noticing it for months, young man. The way you look at me.”

“Oh fuck,” Tommy said, melting in lust.

Mr Simmons chuckled. “But, if that’s where we’re heading, we need to see to it that you’re properly outfitted.”

“Oh yes” said Tommy, relaxing as Mr Simmons rubbed his shoulders.

But then suddenly Mr Simmons’ grip tightened, almost painfully. “You mean ‘yes sir,’ young man.”

Tommy gulped. “Yes. Yes, sir.”

Mr Simmons relaxed his grip and patted Tommy on the shoulder. “That’s better. Now, you said you were interested in ties?”

Tommy glanced over his shoulder at Mr Simmons. Licking his own lips, despite himself, just the thought of this beautifully dressed man taking him under his wing intoxicating him with lust–“Yes sir.”

“Very good. Follow me.” Mr Simmons led Tommy up the stairs, shoes polished like dark mirrors, clicking across the marble steps. “If it is your intention to expand your wardrobe, you ought to act the part as well. I believe you ought to refer to yourself as Thomas from now on, preferably Mr Smith. Clothing does not make the gentleman, after all. It’s all… behavior. A matter of behavior, you see. And knowing your place.”

The newly crowned ‘Thomas’ followed obediently behind Mr Simmons as he led him into an enormous bedroom. Thomas noticed with interest that the four poster bed was decked in black satin sheets.

Mr Simmons moved to his closet and threw open the double doors dramatically. Thomas was positively shocked at what he saw. Row upon row of perfectly hanging suits and shirts, all clearly bespoke and beautifully made. Mr Simmons gestured grandly at an entire wall of hanging silk ties all ordered by colour. There had to be hundreds of them! “Surely there’s something here that captures your particular fancy, my boy.”

“Sir, your collection is amazing! Thank you for showing it to me. I wish I had something even a fraction this good!” Thomas walked to the wall of ties and looked up in awe. He’d never seen anything so beautiful – and güvenilir bahis siteleri arousing – in his life.

“I’ll be right back with something for you, boy. Choose a tie while I’m gone.” Said Mr Simmons as he left the room.

Thomas ran his fingers lovingly over countless ties, growing increasingly aroused at the luxurious silk and satin feel of them as he made his choice. He’d always been particularly fond of pink and purple ties, so he paid extra close attention to that section. When Thomas had been younger, he had mistakenly believed that pink ties were a secret signal used by gay men to subtly announce their sexuality. While he was older and wiser now, he still loved the idea of wearing a pink tie and letting other men around him know he was that way inclined.

A particularly luxurious pink pastel tie caught Thomas’ eye and he knew instantly that he would choose it. It was particularly dandy and effete and he thought that it would lend and air of submissiveness that Mr Simmons would appreciate – and hopefully take advantage of. The material was incredibly thick and he knew it would tie a large and decadent knot.

As Thomas was pulling the tie from the wall, Mr Simmons returned with something in his arms. “This is for you, my boy. I’m almost certain it’s your size. Now be a good boy and put this on.”

Thomas was being handed a 3 piece charcoal pinstripe suit, complete with soft pink satin lining on the suit and waistcoat that perfectly matched the tie in his hands. There was a crisp, new white french cuff shirt in the armful as well, with a sharp cutaway collar.

Thomas’ jaw went slack as Mr Simmons handed him the hanger, lustrous wool brushing up against his tenting trousers. “That looks amazing, sir. But I already have a suit–“

“No, no, I insist. No outfit is complete without proper shoes.” Mr Simmons rushed across the room to another wardrobe and opened it to reveal a massive shoe collection. He picked a pair of black patent loafers and brought them back to Thomas. “These too… and I suppose you’ll need some socks.”

Just the sight of those long, pointed, phallic shoes–Thomas could see his incredulous reflection in the polished leather–his cock was tingling with anticipation. “Sir, this is too much.”

But Mr Simmons was already pulling open a dresser draw, from which he produced a pair of sheer silk over-the-calf socks for Thomas to wear. Handing them to him he wondered aloud. “Perhaps some new cufflinks too?”

Thomas felt like a valet, holding all of these pieces of finery in his arms. In fact, he wondered whether he felt like a “valet” as in, a liveried servant in a fine ancestral estate, or a “valet” as in a piece of furniture for holding a gentleman’s dressing things. He bit his lip. His cock was playing a tug of war with his brain. This was all too much. But wasn’t this what he signed up for? Wasn’t this what he wanted? What would he owe Mr Simmons for all this attention?

From yet another drawer, Mr Simmons presented Thomas with a small box containing some shiny silver cufflinks. Shifting the garments from one arm to the other, Thomas cracked the box open and looked at a pair of perfect and glimmering sterling silver cuffs.

“Now it’s time for you to get dressed and admire yourself in the mirror. I’ll return in ten minutes and I expect you to be ready.”

Before he left the room, Mr Simmons put his hands behind Thomas’ neck and pulled him close so that his mouth was next to Thomas’ ear. Thomas was too stunned to do anything about it. “Once you’re properly dressed, I’m going to make you mine and introduce you to pleasure beyond anything you’ve ever experienced.” He lightly bit Thomas’ ear lobe and then he swiftly turned around and left the room, leaving Thomas standing there with his new clothes in arm, shaking and rock hard.

Still stunned, Thomas stood there for a moment, arms full of these fine garments from Mr Simmons collection. In a full-length mirror nearby, he could see his cock protruding out like a peg in front of him. The aroma of the fine wool. The glossy patent loafers near his feet. It was all too much.

“What have I got myself into?” Thomas whispered aloud. Heart thumping with anticipation, he hung the clothing on an elegant brass hook, took off his rain-soaked suit jacket, and began undressing.

Thomas began dressing himself and every layer aroused him more and more. The pique texture of the crisp french cuff shirt. The stiff, starched collar closing around his neck. The rosy silk of the grosgrain braces. The smoothness of the sheer hosiery stretching over his hairy calves, each hair pushing through. After a moment’s hesitation, staring at the beautiful suit Mr Simmons had handed him, he shimmied out of his damp boxers, swollen cock head bobbing between his shirt tails.

Thomas always tried on a new suit without underwear and today was no exception. Could he handle himself? The thought of his bare balls rubbing against the same luxurious wool that had caressed Mr Simmons–his cock head had a bead of precum on it by the time he stepped into the trousers, pulling them up his legs. The tingle of the soft fabric hugging his glutes and thighs. He could barely tuck himself in.

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