Jack gets curious about some things… and then all preppy breaks loose.
Jack sat on the side and watched everyone else skate. He’d been shredding damn hard himself and needed to catch his breath. He moved his feet back and forth away from each other and back again over and over. He looked down at them, and had to face it. His black and grey Airwalk Ones were shot to hell. ‘I really could use some new kicks.’
He watched the other guys skate for a while longer and then bounded up and rolled away. Each time his sneaker pounded pavement he was reminded that he needed new ones. But the best place to get some was all the way on the other side of town. He was tired and didn’t feel like skating all the way there. He had a thought. There was a Ross just a block or so from his home. ‘They’re bound to have something I can get for now. And cheaper, too. Like maybe they’ll have Puma suedes at least.’ So he altered course to come toward his place from the other way.
Along the way he saw some boys he’d never think of associating with: preppy boys. ‘Fuckers,’ he said to himself. They made him sick. ‘Just look at them in their polos and khakis. Ugh.’ He skated right by them and gave them the finger. Their faces soured and he grinned. He couldn’t help but notice one of the trio had penny loafers on. ‘How da fuck can he WEAR those things? Like, they CAN’T be comfortable!’ Not like the other guy in his casual Sperrys or even the espadrilles the third wore. Not that Jack knew either shoe by their name, he just knew them as preppy shit. But seriously, those loafers looked claustrophobic. He thought about it too much as he continued along.
Then there it was just up ahead - Ross. The discount clothing and home store. He popped up his board and went inside.
He made a direct path to the men’s section and wandered around for the footwear. He checked for his size and then had a look around the selection. All stuff he would never be caught dead in. ‘Da fuck? Wherez the KICKS?’ He then caught sight of some around the bend. Obviously the store separated out the sneakers into their own section. But before he rounded the bend, Jack’s eyes fell upon a pair of chocolate brown penny loafers. He shuddered, yet he couldn’t stop staring at them.
He didn’t know how long he looked at them. But he knew he’d been wondering a long time. ‘Are they comfortable at ALL? CAN they be? They look so stiff and constricting.’ And so he wondered and wondered until he came to his senses and shook his head. ‘Pffft. Like I fuckin care!’ He resumed moving his beat up Airwalk Ones toward their replacement.
Most of the sneakers on the rack sucked. Like weird styles of Nikes no one would buy. Or no name brand. Or baffling unappealing color ways. But then…he saw them. Just as he had hoped for he’d find. Pumas. Suedes. In a flashy red. ‘Fuck yeah.’ And they were only 26 bucks. ‘Fuck yeah again. Mine.’
He didn’t bother to try them on, and headed out. He passed those penny loafers again. His eyes were on them like a magnet. But he drew away, the magnetism of the fiery red Pumas in his hand won out.
He paid for them, giving a snarky attitude to the cashier on purpose. All by his expressions. Like impatience and disgust and annoyance. He didn’t even bother to speak to him when spoken to.
He skated the block home. He flung open his door. “DAD?!???”
No response. His dad usually wasn’t home. Jack never really got along well with him. Not really bad either. Just kind of two strangers living together. Jack did know that his father didn’t approve of his being a skater. Not because he feared for his son’s safety. He just didn’t like it. He thought Jack looked like a “ruffian” as he called it. But Jack didn’t care. He loved being a skate rat. He had been ever since middle school when his mom left.
Jack happily took advantage of his dad not being there to play some video games. There was only one TV and he didn’t have a Switch so if Dad was home it meant he controlled what was on the screen. And if he wasn’t watching anything he often objected to his playing. “Too much damn explosions and noise!” he’d say.
But no dad to complain right now. “But first,” Jack said aloud. He slipped out of his Airwalks and shoved them aside. “You served me well, fellas!” He sat down and put on his new red Pumas. “Yeah. Nice!” He walked around a bit. “Nice.” Then he stood on his board. “Fuck yeah. These’ll do real good.”
He began playing and kept his left foot on his right knee. He loved seeing the formstrip and the little puma on his heel.
But later, after many many kills and levels in his game, he found himself thinking about those penny loafers. He’d catch himself doing it and mentally slapped himself. But over and over he would have it in mind. Finally with both his feet on the ground so that he couldn’t see his blaring red sneakers anymore, he stopped pushing the buttons on his controller and stopped pushing away the thought of the loafers. He couldn’t help but wonder. ‘Are they really all that uncomfortable? I mean, guys WEAR em n shit. Would they really be forcing themselves into pain for the sake of keeping up their preppy style?’ He then shook his head in disgust. ‘Pffft. Probably, yeah.’ But still… he wondered.
The door rattled and his dad came in. Jack was glad to see he’d just had a delay at work. He hated when his dad came in drunk. “Hey Dad.”
“Hello, son.” He stopped in mid step. “New shoes, Jack?”
“Yup!” he said and proudly lifted his left foot to show it off.
Dad sighed. “Did you HAVE to get another pair of sneakers?”
With an attitude attached, Jack replied, “Uh, yeah, I DID. My other kicks are totally trashed.”
“I just wish you’d gotten something else.”
“What da fuck’s wrong with Pumas???”
“No I mean other than stupid skate shoes.”
“Uh, if I’m gonna skate I need skate shoes. Ain’t rocket science.”
“You watch your mouth. Don’t talk to me like I’m some sort of dumbass. And lose the attitude.”
“But seriously, Jack, do you even OWN any other shoes?”
“No that’s why I needed these. I’d LIKE more if you’re offerin’!”
“I am NOT.” He continued walking, then stopped. A moment of thinking. “Maybe I am. Tell you what. You get yourself shoes you can actually WEAR places besides the grocery and that damned skatepark by the end of tomorrow. I’ll reimburse you. If you do not get any, I’m going to take you shopping and pick out some sensible NORMAL nice shoes FOR you. And you may not like the pick.”
“Uh… okay,” he said dejectedly.
“Here’s hoping you can take a damn minute away from your game to buy adult shoes.”
“I will! I will!”
“Pizza should be coming shortly. I’d appreciate it if you didn’t just scarf it at the screen.”
“Sure, Dad.” He said it nicely and sincerely. “Thanks for the pizza.”
“You’re welcome. Thanks for thanking me. Maybe you’ll turn out to be a good boy yet!”
Jack could hear the joking around in his dad’s voice but he also knew that deep down his dad did wish he was a better kid. He went back to his game figuring he’d play until the pizza arrived.
When it did he and dad sat at the kitchen table. They didn’t chat much, but it was nice to be together.
“So… late day at work again, huh?”
“Yeah,” Dad replied, the weight of his disgust quite palpable.
Dad looked under the table at Jack’s feet. “Red, huh? Are you TRYING to draw attention to yourself?”
“Dunno. Maybe. Red’s just cool. I went to Ross on the way home after seeing how beat up my last pair was.”
“How thrifty of you.”
This of course brought the penny loafers to mind again. He stared off into space, wondering that same thing as before. How do they feel? And now that he was being forced to get “nice shoes” he just might have to try them out. He actually thought this and then shuddered mentally. ‘Pffft. Right. I’ll just go to Ross and look for something else dad’ll be okay with and that I am too. I hope.’
“Yah, I was beat n’ didn’t wanna go all the way to the real sneaker store ‘cross town. So I got these.”
“Did they have another color you could have picked?”
“Nah. It’s Ross. They have what they have when you go. It’s a crapshoot.” ‘Which means those penny loafers may not even be there anymore,’ he thought and got comforted by it. “But I love these. They’re bitchin’.”
Dad rolled his eyes.
The rest of pizza consumption went quietly and quickly. Or so it seemed.
As he gathered and threw away the paper plates, Jack debated going to Ross again now or playing more games. But he got his answer when dad put on the TV.
He watched his red Pumas as he walked to the door. “Say dad - imma go out.”
That’s what dad always said. He put his new kicks to work and rolled along the short distance to the discount department store. He could have just walked. But Jack was a skater. It was his identity, he loved being one and the skateboard was an extension of himself.
He sighed before entering the store. Once more he made his way to guys’ shoes. He did it in reverse this time, passing by the sneaker section first. It was a relief that there wasn’t anything cooler that he missed before. He got exactly what he wanted, although he hadn’t planned on the red. But he loved them, such a nice change from the black and grey Airwalks.
And he turned the bend. Still there, looking up at him seeming like they had waited for him to return. He stared at the penny loafers. The brown looked so chocolatey. They looked delicious. And it pained him that he knew he also meant the figurative sense of that word. He zoned out, in turmoil over his desire to know how they would feel on his feet.
‘Well, it can’t hurt to try them on,’ he thought. But he would soon discover it depended on how and what one defined as “hurt”. He sighed again, said to himself ‘Am I really gonna do this?’ But before he could stop himself he had already picked up the shoes. They were lighter than the thought they’d be. And the leather felt sturdy and nice. He sat down on one of the benches and slipped out of his Pumas. He placed the shoes in front of him. ‘Here goes…’ And in went his foot to the right loafer. To his surprise, it slid in easily. And also to his surprise it wasn’t stiff and cold and constricted. It felt…good, damn it. Taken by the charm of it, he eased in his left. He stood up. ‘I have penny loafers on,’ he said to himself. ‘I have PENNY LOAFERS on…!!’ he screamed in horror.
It was weird. He knew they were more formal than he was used to. He knew they were “dress shoes”. He knew they were the farthest thing from skater. He knew they were preppy. But he also knew that he said to himself, ‘I like them.’
He walked around a bit. They didn’t feel like clamps on his feet. They didn’t feel like weights, literally or figuratively. They were just… nice. He reeled for a moment. Did he actually LIKE them? Worse, he found himself thinking he WANTED them. He stood grappling with it and then finally said, ‘Well, it’ll make dad happy I suspect. And lookit. They’re by Florsheim. That’s like a serious brand, I think. For only 40 bucks. I think that might be a steal.’
So he whipped out his phone and started looking for pricing on loafers. He scarcely believed he thumbed through pictures of loafers. There. It was definitely those exact ones. ‘Berkley, style huh? WHOA. One hundred and ten! Yeah I’m picking these bad boys up for this price for sure!’
He started to the checkout and got to the end of the aisle before he realized he still wore them and had left his skate shoes and skateboard behind. ‘DUH!’ He slipped out of the loafers and popped his feet back in his red Pumas. ‘Well, guyz, sorry about that.’
He made the purchase, making the small talk and being very courteous to the clerk. Then he hurried home. When he got in the door, he could hear that dad was still watching TV. Jack decided to see how long it would take dad to notice. He took off his sneakers and put on the new shoes. It unnerved him that he had been so eager to put on penny loafers again. ‘Heh, maybe I’m turning preppy.’ He laughed it off and then sat down. The only light was from the TV glow. It wouldn’t necessarily be easy for dad to spot. So Jack put up his right foot on his left knee. ‘That should be right in dad’s sight line.’
It took a while, for the show to be over in fact. But dad eventually saw. Jack had certainly looked a bunch himself. And wriggled his foot to try and get dad’s attention. All it served to do is make Jack appreciate them more. Did he actually LIKE them? He dare not think that.
“SaaaaaaaY! Look at you, son!” Dad had a big smile. “For one thing I did NOT expect you to do as I asked right away. For another I thought I’d have to tell you what you got isn’t acceptable. But no, here’s my good boy in penny loafers! Not what I would have expected you to pick because I figure those aren’t your style at ALL. But I’m glad you got those. Damn glad!”
“Cool. I thought you’d like them.”
“More importantly, do YOU?”
“Not really. I got them to please you. But then, we’ll, I guess they are kinda nice. As dress shoes go. Too preppy though.”
“Well it sounds like you can live with them. Good job, boy. And you know… you could stand to be a little preppier.”
“In fact, let me see those snazzy new loafers of yours with some khakis.”
“I mean it, son. Go change into your khakis. I bet you look great.”
Wearing the loafers was one thing. But to have on khakis with them, too??! “Dad, not right now, okay?”
“Yes now. What the hell else you got to do?”
“But I don’t wanna!”
“Jezuz, Jack, you sound like a two year old. It’s not going to kill you. March.”
Jack signed heavily and marched to his room. He made a literal march, each step a reminder of what he wore. He grumbled the whole time getting them off (though he did appreciate how easy it was to get the loafers on and off) and taking off his jeans and rummaging through the closet for his khakis. He didn’t wear khakis much. Oh from time to time a skater will have khakis but usually not tailored and nice fitting. But that happened to be what he grabbed and soon his legs were beige instead of blue. He then slipped back into the penny loafers.
When he looked in his full length mirror he had to admit it looked nice. He stared at the khaki and chocolate combination and the moments melted away like chocolate in the sun. He didn’t notice the placid look on his face.
The loose as hell T-shirt just didn’t look right. Not at all. He heard himself say inside, ‘I wonder what I’d look like with a nice shirt too.’
It was like he was on autopilot. Before he knew what he was doing, he yanked off the T-shirt and threw it on the floor. Then he went deep into the bowels of his closet. The part where the sun never shone due to lack of use. He flipped past clothes he totally forgot about and then found the one he was looking for - a powder blue Oxford button down shirt. He slid his arms through and started buttoning up. About halfway through he stopped.
“What the fuck am I DOING?!?” he said aloud. But when he looked at himself in the eyes, the placid grin came back and he resumed. Soon he was all done except for the top button. ‘Oh. Better tuck in my shirt to my khakis. Don’t want to look like a schlub.’
And so stood Jack. But not Jack. Not Skater Jack at least. This was almost another boy. It was Preppy Jack. ‘Heh,’ he giggled. ‘Reminds me of Pepper Jack.’ The grinning happened again. And he could do naught but stare. He was frozen in two ways. First, he just plain didn’t move looking at his preppified self. Second, he was frozen in fear. Fear that he was actually liking this. After all that damn smile he was now noticing indicated as such. It was like being inside and outside of himself at the same time.
He zoned out, dead calm eyes fixed forward and a happy self-satisfied grin.
“J A C K!!!”
He jolted and saw dad. “I’ve been calling you!”
“Oh. Sorry. I guess I - uh…”
“Nice to see you looking nice, boy!”
“I’m not sure how -“
“I think you look terrific, son. You make a great preppy!”
“I make a great preppy,” he agreed, or part of him did. It was interesting how he could sound absolutely certain and overly doubtful at the same time.
“You’ll want to dress like this all the time now, I reckon?”
Jack came back to his senses. “Nah, this wuzza fluke. I ain’t a preppy.”
“But you could be, if you wanted to,” dad said, putting his hand on the boy’s shoulder.
That glazed look came back. “I could be,” he said droningly.
“You’re already dressed, Jackson. Why not just keep it on for today and see how you like it?”
And so Jack thought, ‘‘Why not? Like he said I’m already dressed. He’s right. I’m curious to see how I like it.’ “Okay, sure,” said aloud.
And so Jack went about the rest of the night in preppy garb. Other than a few moments of “WTF??!!” when he’d see a bit of the clothing when he moved, he pretty much resigned himself to being content in the outfit. ‘And these penny loafers are da shit!’
When he went to bed he would have thought he’d not be able to shed the preppy stuff fast enough. Rather it was more like he regretted taking it off.
That night he had a dream about Preppy Jack, resplendently attired in a pink polo and madras and boat shoes. He had preppy pals and ever so loved being polite and helpful and friendly and preppy.
When he awoke he had a little freak out moment. For there piled on his chair were those very clothing items. Now, it had been entirely possible that the polo shirt had been in there and he didn’t realize it like some stashed away present from Aunt Maggie or something. But he knew he never had short weirdly patterned pants like that. And he for FUCK’s sure didn’t have… boat shoes!
Skater Jack wanted to vomit. ‘Da fUHck!!??’ Preppy Jack wanted to cheer. ‘How am I so lucky?’
Dad walked by the door. He peered in and saw his son agape at the clothes.
“Like them, son?”
‘Uh no. The preppy me up experiment is over. I’m going back to being ME!” He turned away and grabbed his hoodie and torn jeans and headed to the bathroom. He didn’t bring underwear so he just went commando. But all it really led to was stroking himself. He thumped quite hard so that he got harder and harder. It felt great. Pumping and pumping. Yeah. Yeah. Mmmm polo. Yeah. Stroke. Yank. Mmmmm boat shoes. YEAAAAHHH!!!!! He shot his load. “YeahhhhwhAAATtheFUCK?!?!” He stopped and looked at his cum glazed hand. ‘Did I … did I just…t wank off to PREPPY clothes?’
He didn’t know what to think. He was beside himself. And it appeared that the one of himself next to himself, so to speak, was a proud preppy waiting to bust out.
‘Well,’ thought Jackson as he cleaned up like a good boy, ‘I guess I am curious how the polo shirt feels. And boat shoes are like classic. I should try them on…I guess.’ He was just curious.
Skater Jack had to watch as Preppy Jack took over and got into some tighty whiteys he didn’t normally use, the pink polo, madras and classic brown Sperrys. He fondled the little alligator on his shirt. He looked in the mirror. Jack saw yet another preppy image of himself.
Could he pass for a prep? He certainly looked like one, but could he be taken for one? He was curious. So he went to the bathroom mirror and combed his hair. He used to just run his fingers and leave the shag as it may. But now it all lay smooth, and he even made a nice side part. Boy, he sure looked preppy. ‘Now to see if people think I AM.”
So prepped up Jack went outside. It felt so strange to not have his skateboard. Hell, it felt so strange to be wearing Top-Siders. But also kind of good. He kept walking, toward the skatepark by force of habit. But he didn’t get all the way there. He stopped for a moment, realizing that he might see people he knew. So he turned a corner and kept walking in his spiffy outfit.
“Hello, friend!” came a voice.
Jack looked over and saw a purely preppy fellow. He had on a peach Oxford button down shirt with a cherry red bow tie atop a chocolate sweater vest decorated with maroon and light blue argyle. His chinos were a nice slate color and he sported shiny brown penny loafers with no socks. Jack admired the loafers. “Hi.”
“Haven’t had the pleasure of making your acquaintance before I don’t think,” said the preppy with a big happy smile. “I’m Blake.” He thrust his hand out.
The preppy clad skater boy grabbed his hand and said, “J-Jackson.” It surprised him that he fumbled with his name and even more so that he chose to say Jackson. Blake had a nice firm grip. Jack wondered why his dick throbbed a bit while they shook.
“Are you new to town? I know all the preps but as I said, I’m not familiar with you.”
‘O. M. G.,’ thought Jack, ‘he doesn’t know I’m just posing!’
“Uh, no. I’m from the neighborhood. I just, well, the thing is -“
“Wanting to be preppy is what’s new?”
“Uh, I don’t know that I WANT to be preppy.”
“Sure you do! You’ve dressed in a totally preppy outfit. Your hair’s styled preppy. And you have the right countenance.”
“I was just curious.”
“We’ll be curious no more. Just be the preppy you always wanted to be.”
“Uh, ok, Blake.”
“Don’t say ‘uh’. It’s unbecoming.”
“No worries, Jackson.”
There was an awkward silence. Blake was looking him up and down. “You’re a handsome guy.”
He sort of gulped. “Thanks, I guess.” If he was honest with himself, he enjoyed hearing that. He was always curious if gay boys found him attractive.
“Weird question,” said Blake. “Totally okay if you say no.”
“Would you pleasure yourself while I watch? I have a fetish for hot preppy guys and between your strong jaw and your boat shoes, you’re really doing it for me.”
Jackson was always curious what it would be like to whack off in front of someone. He had to admit that the uneasy feeling it gave him was exciting. He also never figured the voyeur would be a guy since he just assumed girls would just be sucking his dick instead. Which of course always made him curious what it would be like if a guy sucked him. He certainly never wanted to do any such thing or other with any of the guys down at the skatepark.. But now here was this hot preppy who WANTED to watch AND found him hot, apparently. “Okay, Blake.”
“Keen!” Blake smiled, in a curl of lip both excited and vapid. “Let’s go somewhere private.”
Jackson followed Blake to a little stone building. He was always curious what this little room just at the edge of the park was doing there. Now it became quite clear.
Blake unlocked it and held the door open for Jackson. As Jackson stepped through, Blake put his hand on his shoulder. The touch felt nice. The door shut and Blake relocked it.
“All right, Preppy,” said Blake, “stroke your hot cock for me.”
Jack hesitated at first, but the thought of fulfilling a curiosity proved too great. He also thought it would take a while to get hard. But no. Fulfilling the fantasy was a great jolt and Blake looked so well dressed, Jack was practically in full stiffy when he whipped it out.
He began to caress his cock, getting harder and harder as it sank in that he was actually whacking off in front of a boy. A preppy boy. Who had just called HIM preppy. He stared down at Blake’s loafers. Who was in turn staring at his boat shoes. ‘My fucking gawd, I have BOAT SHOES on,’ thought Jack, and it only made him harder to know it. He moved his gaze up to Blake’s grinning face. He looked so smug and cute. And he had a great jawline, too, Jack realized, prompted by Blake’s comment about his own. Mmmmm. Argyle. Mmmm, hot preppy guy…. Oooooo….oooooo….. And then…. Jackson shot his load, warm jizz flowing out of his engorged dick, puddling just between his Sperrys.
He looked over at Blake who was biting his lower lip and feeling the crotch of his slate chinos. A feeling came over Jack. He didn’t feel like himself. It wasn’t anything like embarrassment for what he had just done or misgivings about doing something gay. It was a different feeling. One he never felt before. “I feel…empty,” he said aloud.
“I should say so, Jackson!” Blake grinned, pointing at the amount of white cum next to the white of the Sperry soles.
“No… I mean… I don’ ,,, don’t feel like… myself. Like I’ve lost all of who I am.”
“AH,” said Blake. His loafers clacked over and he put an arm around his new friend. “I suspected from the start that your delicious preppy togs are new to you.”
“Why yes, Blake. I only started wearing them yesterday and today, sort of at the behest of my dad.”
“How did you identify yourself before?”
“I’m a skater.” But as he said it, it didn’t sound right. He corrected himself. “I WAS a skater. I don’t feel like one right now. I don’t even know how that’s supposed to feel, or how I ever did feel when I thought that’s who I was.”
“I would never have guessed you to be one of those baggy clothed morons, Jackson. I would have figured you were always a preppy. You fit the bill so well.”
This both pleased and bothered Jack. After all, his curiosity had been satiated in that regard - he COULD pass for preppy. But did he really WANT to? Also… “I don’t FEEL preppy,” he said aloud. “As I mentioned, I don’t feel like…anything.”
“That’s because you just drained your essence. It’s right there at your Sperrys.”
Jackson looked down. Blake continued. “THAT, my dear Jackson, is your skater self.”
“But… but… I’ve whacked off PLENTY of times! Even spilled my jizz all over the floor like this, too! I never felt like THIS before!”
“Ah, but had you ever done so preppily dressed with your hair parted before?” asked Blake, his eyebrow raising and the cute smug grin returning. He watched Jackson gulp. “Yep, I’m afraid changing one’s perception of oneself such as you have while one pleasures oneself will do that.”
“What do I do now? I don’t want to feel like this! I have no sense of self! I’m … EMPTY!!”
“You don’t have to feel empty, my friend.”
Blake undid the zipper on his slate chinos and pulled down his tighty whiteys. His dick was still fat and at attention. Jackson couldn’t help himself. He stared at Blake’s dick, then at the nice dress slacks pooled around those gorgeous penny loafers against his bare ankles and back to his dick.
“Suck my preppy penis, Jackson. I’ll fill you up. Swallow some Essence of Preppy and you can be preppy too.”
“I can be preppy, too,” repeated Jackson, mindlessly, as he bent his knees, making him re-aware of his madras. ‘Am I really going to suck dick?’ he asked himself. Why not? He was always curious. So he opened wide and slid his mouth around the great big cock in front of him. It smelled great. It tasted better. And he went to town, head bobbing and sucking. Blake loved it. Jackson could tell. Not just from the moaning, but from looking up into the sheer pleasure in his gorgeous eyes. Nice Ivy League haircut, thought Jackson. Mmmf. Mmmf. Mmmf. He put his hands to Blake’s butt and squeezed it as he pumped the preppy even harder.
“That’s it my boy…almost there…yes yes yeS yES YES YESSS!!” Blake’s hot cum filled Jackson’s mouth. “Swallow it, Jackson. Swallow my preppy seed and you won’t feel empty anymore. You’ll feel what you were always meant to feel. You’ll feel PREPPY!”
Jackson didn’t want to hesitate. He didn’t want to be empty. He wanted to be preppy. He needed to be a prepster. He eagerly sent the jizz down his gullet. He stood up, zipped up his madras and looked at his boat shoes. “By golly, I DO feel preppy.”
Blake had righted his clothes as well, and Jackson watched with a twinge in his pants as the preppy tucked in his peach Oxford and smoothed out his argyle sweater.
“Yes?” eyebrowed Blake, seeming like he knew what Jackson would say next.
“I do feel as if I could be preppier.”
“Oh of COURSE, my friend! One can ALWAYS be preppier,” he said with that glazed grin. “But don’t worry. You ARE preppy. And you and I are pals now. I’m here to mentor you in the ways of prepdom.”
“Keen!” said Jackson. He was curious what else being preppy had in store for him. He spent the rest of the afternoon with Blake, who told him all manner of things preppy…and he only scratched the surface.
When Jackson arrived home, he was delighted to find his dad. “Hello, father. You were right,” he beamed, “I am much better off as a preppy good boy, and I shall strive to be an even better one.”
Dad’s eyes got wide. “Glad to hear it, Jack!”
“Please call me Jackson.”
“Sure thing, JackSON,” he said, obviously going for the pun of meaning his own boy. “So you really are okay with going prep?”
“Oh yes, father! It’s my only identity now.”
Dad noticed that his good boy said this with those damned red skate shoes on the floor next to the boat shoes on his feet, and the boy didn’t even so much glance at them, as if he didn’t know they were there. Nope, he kept eye contact with his father, his elder.
“Well, son, if you’re sure you’re a preppy now, you’ll need a lot more than these clothes. To think I bought them thinking you’d hate them. The Sperrys were my pick for the shoes I told you I wanted you to get.”
“Oh but father, I love my Top-Siders. True preppies have at least one pair!”
“Would you like another?”
“Boy would I! Maybe the navy blue ones!” he grinned vapidly. “OR… the oatmeal! My friend Blake told me about the oatmeal boat shoes!”
“Well then, Jackson, let’s go get you a bunch of new togs and both those colors of Sperrys.”
“GOLLY! Thank you ever so much, father!” The white soles of the ones he had on could be seen in full view as he ran off toward the car.
And get both navy blue and oatmeal boat shoes he did - and a whole plethora of preppy.
To dad’s surprise and delight, this wasn’t some cruel hoax to make him spend money. It wasn’t a phase either. And his son never once showed up again without a perfectly preppy outfit. He even wore blazers and ties. And that friend of his, Blake - such a good boy! He was proper, well mannered, respectful and so preppy. It made Dad proud his son had such a good influence on him. And yes, he knew he was his son’s boyfriend. He didn’t mind at all. At least his son wasn’t a ruffian skater anymore.
And just to make sure, Dad threw away the skateboard and the red Pumas and all of his son’s skate culture crap. Jackson never brought it up. In fact, he never even had a vague curiosity as to what became of them. That’s because Jackson wasn’t a skater anymore. He didn’t want to be. He only wanted to be a good preppy boy - no, a BETTER preppy boy. As all boys should be.