Meet Ricky...?

By PreppifiedGuy
published March 18, 2019

When Skater Ricky sets foot in a certain diner, his life changes for the preppy.

Ricky crammed his feet into his Vans skate shoes. How he loved the way they hugged his feet. He slapped on his SnapBack over his long and shaggy brown hair. The plastic strip nestled just over his frosted bleach blonde bangs. He felt complete. Ricky was a skater to the core. He wore the outfits, knew a myriad of tricks on his board and spoke the lingo as second nature. He’d been a skate rat as long as he could remember. He got his first Vans as a little tyke (classic Skate Hi) and performed an Ollie at the tender age of five. When you grow up just blocks from the skatepark, you’re bound to be absorbed into the culture. And Ricky prided himself on his identity. He loved being a skater. It was in his blood.

He popped up his board to his hand and went on his way. Soon his skateboard clacked over the sidewalk. But even though it’s just a short trip to the park, he suddenly felt overwhelmed by the need to relieve his bladder. So he ground to a halt and went into the “malt shop” type place. It’s supposed to be one of those nostalgic places or something, Ricky didn’t really give a shit. He didn’t go for that kind of crap. And since it has always looked like a sit down diner, he never had cause to go in otherwise. Why waste time on that when he could get a yummy and pleasingly greasy taco that he could shove in his mouth on the way to the skatepark? But today, he really needed to go to the bathroom, like NOW.

Bells jingled on his way in. “Yo, I needsta drain the lizard.”

“Pardon?” The guy who spoke had a plaster smile and hair perfectly trimmed and parted.

“Gosta whiz, bro.”

“Would you possibly mean that you have to use our facilities?”

“Look, dude, I’mma pee all over the floor if ya don’t tell me where dat shit be.”

“Restrooms are for patrons of the establishment only,” the neatly groomed guy said.

“Youz fuckin’ kiddin’ me bro?” He squeezed his crotch in an attempt to quell the piss fighting to get out.

“I am not jesting. But since you’re in a pickle as it were, you can get something on the way out.”

“Yah sure man whatevs.” He started toward the back.

“First door on the left down the hall,” the guy informed him, cheery as cheery can be.

Ricky made it just in time and shook his big dick off at the urinal. He didn’t bother to wash his hands and headed back out to the diner.
Now that he didn’t have to focus on not pissing himself, he noticed the people in the place. For one, only guys were in the seats and booths. For another, they were all dressed to impress. To impress someone, certainly, but not Ricky, that’s for sure. He couldn’t stand the sight of them. For each and every one was prepped out to the max. Some of them in button down oxford shirts, others in polos. Sweater vests and bow ties. Various shades of khakis on everyone. A few even had on blazers. And on their feet were loafers of one sort or another and the others had on (oh how Ricky winced) boat shoes.

‘Get me da fuck away from these preppies!’ he thought, and raced toward the exit.

“Young man!” The voice of the greeter. Ricky now noticed he had on a bow tie too. “You cannot leave until you patronize our little eatery.”


“I wouldn’t say so if I were not.”

“Aw fuckin’ hell.”

“Watch your language, please. I’ve listened to enough profanity from you.”

Ricky rolled his eyes, partly at the pinstriped shirt the guy wore. “Whatever man. I don’ ‘spose you have like burgers ta go?”

“We do not. But if you like, you can purchase this bottle of water. It’s only twenty-five cents.” He held it out for him.

“And then youz’ll lemme bounce?”

“If by ‘bounce’ you mean leave, then indeed. No tax for it either. Just a quarter.”

“Deal.” He grabbed the bottle and threw a quarter at him. He couldn’t get away from the pride of preps fast enough.

The wheels of his skateboard clacked over the sidewalk to the skatepark. His friends Jim and Grizz gave him a salute and he skidded over to them. “Yo boyz!”

“Sup, Ricky!” said Jim.

Grizz nodded and then looked down. Ricky followed with his head and took a gander at Grizz’s sneakers.

“Whoa! Nice kicks, bro!” Ricky truly admired the red and black Osiris D3s. They looked fresh as could be. “Fuckin’ dope, yo!”

Grizz grinned. “Yah, thanks man. Copped ‘em last night.”

“How dey feel?”

“Sweet as shit, dude.”

“Awesomesauce. All right, let’s tear up the park!” Ricky said.

Their baggy shirts flapped behind them as they eased into the mix of skaters sailing around the curved walls and bowls of the park.

After a little while, following a bunch of killer tricks and plenty of wheeling around in general, the three friends took a breather on a bench. Grizz rested his foot on his knee and jostled the infamous skate shoe a bit, as if to say ‘yeah, that’s right, you wish you had my kicks, bro’. Ricky couldn’t take his eyes off of it. “They ARE totally bitchin’ dude. Love that color way!” Grizz grinned again.

Jim grabbed his bottle of Coke and started swigging it down. ‘Good idea’, thought Ricky and he took out the water bottle. As he downed a little, he couldn’t help but think of that damned diner and the preps in it. It made him physically shudder and he stared at the D3s to get rid of the image. But he still downed the water.

Two things struck him about it. First, it sure had been a huge bottle for just twenty-five cents! Second he felt, like, super refreshed. He’d never known a drink to be so satisfying. He felt cleansed as well as the parched feeling going away. It felt like his whole brain had been renewed.
Grizz asked him for a sip. “Fuck off, it’s mine. Backwash, dude.”

Jim egged them back into the park, and they skated for a little while longer. But Ricky kept flubbing. He couldn’t even seem to do a simple Kick Flip.

“Lost my mojo all the suddenz,” he laughed. He tried, but he just sucked for the rest of the day.

The trio of friends parted ways with fist bumps and an utterance of “Later”. Naturally, Ricky passed by the diner on the way home. That water itched in his mind. ‘Fuck,’ he thought, ‘only a quarter. Can’t buyz it cheaper. And it did refresh the fuck outta me.’

He swallowed hard to be able to stand going inside. He opened the door. The same bow tied, perfectly parted hair guy grinned at him with a plaster smile.

“Welcome back, young man!”

“Uh, yeah. Just gimme a few of those waters.” He plopped three quarters on the counter.

The well groomed guy gladly gave him the bottles, and Ricky turned tail to get out as soon as he could. It’s like he could feel the khaki colors everywhere pressing into him. But even though he tried to make a break for it, one of the guys caught his eye.

‘‘Is that..?!’ He stared harder. Over in one of the booths sat a preppy who looked sorta like Jumpin’ Joey. Joey had been a hard core skater they hadn’t seen at the park in forever. Grizz, Jim & Ricky had just assumed he moved away. But this guy sure resembled him. Oh sure, Jumpin’ Joey had spiky purple tinted hair and wore studded leather on his wrists with rock T-shirts and baggy jeans with a wallet chain dangling and bad ass Etnies. But this guy’s hair had been a bright blond with each strand perfectly in place with pomade and wore a pink oxford under a chocolate sweater vest, khakis and cordovan penny loafers with no socks. But… that was definitely Jumpin’ Joey’s face. ‘Nah… couldn’t be.’ Ricky shuddered again and left.

He downed another water on the way home. So damn good. His mojo still failed him, as he could barely even Ollie up the curbs. ‘What the fuck??’ Then he chastised himself for using foul language. ‘Wait. What? Why would I think that? Fuckin’ talk like I fuckin’ shit as hell wanna,’ he said to himself, but the idea that it was bad came to him again.

Soon he’d been laying on his bed, trying to figure out what went wrong with his skating ability today. But it’s like the water had cleansed his mind, he couldn’t come up with any ideas. So instead he just stared at his Vans. Yeah, he fricking loved ‘em. Then he thought of Grizz’s awesome red & black D3s. Ricky wouldn’t mind having a pair himself. He’d want the Smurf blue ones, though. He went on daydreaming about sneakers. But after a while his thoughts turned to the loafers on that doppelgänger of Jumpin’ Joey.

‘Really snazzy shoes, those,’ he heard himself think. Then he realized what he’d been doing. Admiring that guy’s penny loafers! ‘What the FUCK?! I mean heck…Ugh…what’s da matterz wif me?’ He darted up and stared at his Vans. He moved his foot to his knee and patted the sneaker lovingly a few times. Then he played video games the rest of the day and scarfed down a pizza.

He had fallen asleep on the couch and awoke late the next morning. He finished off the pizza, cold, and drank down one of the waters from the diner.

Once again he felt utterly refreshed, like all the stress in him had been washed away.

He changed his clothes to another T-shirt and put on a crumpled flannel, unbuttoned, of course. He still wore his Vans and jeans and underwear from yesterday. Like it mattered. He looked like the skater boi he knew himself to be (despite that he forgot his cap) and mentally hugged his sneakers as he kicked up his board to his hand. They hugged him back around his feet, but he also dropped the board back down to them. ‘Fuck,’ he thought, and another feeling that it was wrong to swear came to him. He reached for the board and headed out.

The dreaded diner loomed ahead, and he debated going inside for more of that cheap refreshing water. It got decided for him when realized he’d drank most of the last bottle on the way there and he had to pee real bad. So his sneaker crossed the threshold of the eatery. Yup, still filled with preppy guys. And yes, the same plastered smile bow tied fellow greeted him.

Ricky heard himself say, “Good morning, sir. Might I use your restroom? I will gladly buy bottles of your water.” ‘What da hell? Why am I bein’ all polite n’ shit?’ he thought.

“Certainly, young man.” His smile barely moved.

Ricky focused straight ahead and tried not to think of the pastels and khakis abounding. But it didn’t stop him from catching a glimpse of some shiny black penny loafers. ‘Nice,’ he thought. “DA FUCK?’ came next along with an immediate chastising of himself. He drained his piss from his big cock (even when flaccid) and meant to get out as soon as possible.

Ricky booked down the aisle of the diner as if he were on his board and slapped a dollar on the counter. The prep gave him four bottles of water. Ricky left as soon as possible and bumped directly into a preppy on his way into the diner. “My apologies,” said the prep in a saccharine manner. Ricky looked him over. A mint green polo shirt with the little crocodile emblazoned on his pec, khaki shorts held up with a striped ribbon belt and brown boat shoes with no socks. Ricky nearly threw up all over them. But what really got him is this was the guy who looked like Joey. He had to ask. “J-J-Jumpin’ Joey??”

“Golly,” said the prep. “I haven’t heard that in a quite some time. If you don’t mind, I prefer Joseph.”

“What the HELL? You always pummeled da shit outta dudes when dey called you dat!”

“Did I? Oh dear, what a ruffian I must have been. I’m so glad that’s behind me now.”

“Joey, da fuck happened to you?” Ricky had been too riled up to notice his cursing. “You were like the best skater at the park! Now you’re all…preppy!”

“Isn’t it wonderful? I finally am who I ought to be. A good boy.”

“Joey! No! You’d always spit at preps.”

“I did?? Gee willikers, I must have been awful. Glad I’m myself now.”

“But you’re NOT! You’re a skate rat! Not a goody-goody…ugh… prep!”

“I’m sorry you feel that way. And I can only pray that you become enlightened to shed that loathsome lifestyle. It’s so much better being preppy, Frederick.”

“DON’T call me that, fucker!” Ricky leaned into him like he’d hit him.

“Tsk tsk, such language! I’ll take my leave of you. Have a pleasant day.” With that Joseph entered the diner and Ricky watched through the window as ‘Joey’ greeted his preppy pals.

Ricky shuddered, and skated away. He fell off his board a block away. ‘Well shucks,’ he thought. ‘Gah! Shucks?! I gotta get a grip.’ He decided not to hit the skatepark right away. ‘Maybe coppin’ some fresh kicks will fix me.’

So he headed over to the strip mall nearby. He skated part of the way but fumbled too many times to not walk. He downed one of the bottles of water on his way there.

Once inside the sneaker shop he felt better. He stood in front of the skate shoes. He looked right at the Osiris D3s. But they didn’t have the Smurf blue. ‘I’d better stick with Vans anywayz. They’re the bomb.’ So he looked around, sort of in a daze from the water. He finally made a selection and bought them. He stuffed the Vans he was wearing into the box and stuffed that into his bag. Naturally he wore his new sneakers to the skatepark. He didn’t even fumble on the way.

When he got there Grizz and Jim were already shredding. They gave him a wave during a glide and then headed over. Grizz looked down and saw Ricky’s new kicks. But Ricky didn’t notice him notice them.

“Da fuck, bro?! Youz preppy now?” Grizz grimaced.

‘Huh?’ Did they see me talking to Joey?’ thought Ricky. Then he said aloud, “Fuck you mean, brah?”

Grizz pointed to the shoes. Ricky looked down. Horror overcame over him. THESE are what he selected?? He saw sneakers, yes, but these were made to look like penny loafers. But he KNEW he bought Vans. Vans makes penny loafer sneakers, apparently. He had to respond so he just said, “Fuck off, they’re VANS.”

“Vans for PREPS maybe,” laughed Jim.

Ricky panicked inside. How did this happen? Why would he pick penny loafer sneakers?

“FINE!” he said, and slipped out of them. In a huff he opened his bag and put on his other pair. “HAPPY now, guyz?”

Grizz and Jim snickered and Ricky growled.

“Seriously, why was you wearin’ those?” laughed Jim.

“Ida know. For kicks… get it?” he ventured as a joke.

But it flopped. The guys just shook their heads.

“C’mon, let’s shred now that you’re dressed properly,” said Grizz.

Fortunately for Ricky’s sanity they didn’t mention the incident again for the rest of the skate time, and he didn’t do too badly in his shredding either. Pretty much the only time he spilled is each time he saw a skater bro in khakis. Just a couple of them wore them, yes. But they were also really baggy and frayed and scuffed.

On the way home he had another bottle of water. He purposely went another way to avoid the diner. But he stopped at a park bench. He couldn’t stop thinking about the sneakers in his bag. One minute he beat himself up for getting them without even realizing it, and the next he desperately wanted to put them on again. He didn’t want to look weird changing his shoes on a bench, though. So he hurried home, and by the time he got there the desire to wear his new sneakers was too strong. He put them on as soon as he could and threw his other shoes in a corner forcefully, as if he didn’t want them anymore.

He played more video games and took a glance at his shoes - his penny loafer sneakers - more times than he carried to admit. They were still VANS, damn it! He grabbed another bottle of the water and felt in a zone. A refreshed zone.

And then he got to thinking. ‘Heck, those guyz in khakis looked pretty dope. And they was STILL skaters. Don’t I have a pair of khakis for formal events n’ shit?’ He thought so. He kept looking at his shoes and thinking they might look better with something other than his dirty denim. Another swig of water. “I’mma gonna look,” he said aloud.

So he went to his closet. He moved lots of crap around and way in the back, yep, there they were. He never would have found them before he moved stuff, so buried had they been. His uncle gave him them for Christmas or a birthday or some holiday or other, he couldn’t remember. His uncle saw Ricky wrinkle his nose in disgust when he opened the present, but he told him they would come in handy for a formal event or a job interview one day. Well, it wasn’t either of those right now, but damn, how Ricky wanted to wear them!

He hated taking his new shoes off, but he had to if he was to wear the khakis. He dropped his ragged dirty baggy jeans and wondered why he was getting a hard on. He ignored it and slid the chinos over his legs and gently slid his feet back into his penny loafer sneakers. His lower half now clad in khaki and the sneaker shoes on his feet, he felt great. He went back to playing video games.

But he didn’t play for very long and he dropped the controller to the side. Instead of the pixel paradise on the screen, he gazed at his khaki-colored legs and his black rubber soled loafers. ‘I look so good in this.’ His expression changed, and if he could see himself he’d know he had a glazed look with a plastered smile.

After a while he came to, of sorts, and suddenly couldn’t believe what he saw. “What the hell am I doin’ in KHAKIS?” he said aloud. “What the FUCK am I wearin’??!!” But just as suddenly the refreshed and relaxed section of his head said to him, ‘Be cool. It’s cool. Skaters DO wear khakis now n’ then. And they ARE Vans, after all.’ He moved his pseudo-penny loafered foot to his knee to double check. Yes. These shoes had the famous waffle sole he loved so much. These would grip his skateboard just as well as the next pair. They WERE Vans, and he felt much better about himself. ‘And they sure are snazzy.’ He resumed his video games. He also played with his hard cock a bit through the soft fabric of his chinos.

When he went to bed, he discovered he had absentmindedly buttoned up his flannel. He shrugged and left it, crashing in his clothes. He drifted to sleep, happy that his “gym loafers” and khakis still clung to him.

The next morning he decided to take a shower. Usually Ricky only washed when he felt especially gross. But today he did it anyway. And what did he put on when he dressed? Clean underwear and his chinos. Naturally the new shoes as well. He slipped on a too big for him T-shirt with the Vans logo. He almost capped himself with the SnapBack as usual, but didn’t put it on at the last second. Instead he went back to the bathroom and combed his hair! Ricky never did that, and thought nothing of doing it now.

Then he grabbed his backpack and skateboard and headed out But he didn’t bother to ride the board. He just walked, all the while smiling about his lower half. As he approached the diner his skater self wondered at the khakis and sneaker shoes. ‘I…I just dunno.’

“Greetings, Frederick!”

He recognized the voice as Jumpin’ Joey, er, Joseph. “Don’t call me that, please.” He noted that he said it politely as he grabbed one of those waters and started chugging.

“Looking good there!” said Joseph. Today he wore a yellow button down oxford shirt with a red Polo player and pony. He also had khakis, but in a slightly darker shade, argyle socks to match his shirt and brown penny loafers. “Chino slacks look splendid on you. And those are some pretty neat shoes.”

It disturbed Ricky that the preppy thought he looked good, and especially that he liked the shoes. But his mind quieted with another sip of water. “Uh… thanks?”

“Looks like you might’ve taken my advice?”


“You’ve prepped up a bit,” Joseph said with one of those plastered grins.

“Uh…” Ricky churned inside.

“But to be honest, you should really have true loafers. And your shirt’s too big. At least tuck it in.”

“Uh…okay.” Ricky couldn’t stop himself from doing so.

“Much better! You hungry? I’ll buy you breakfast.”

“Oh, uh…” Ricky’s stomach growled. “Um, yeah sure. Thanks.” Why turn down a free meal?

Joseph held the door open for him. There were already a pride of preppies having their morning meal. Ricky tried to ignore the pastels and side parts.

“I recommend the waffles, Frederick.”

“Uh, call me Rick, can you?” He said it a bit curtly but wondered why he dropped the Y.

“Sure, Rick. Say, you even combed your hair!”

“I..I did??”

“Hee hee, you’re silly.”

A waiter (bow tied of course) came to take their orders. Joseph ordered for Ricky before he could even speak up. Apparently he was getting those waffles, a poached egg and bacon with an orange juice.

Joseph started talking, babbling really, about what Ricky couldn’t even say. Partly because Joseph seemed to speak a mile a minute and partly because Ricky started panicking inside.

‘Holy crap, I’m sitting across from a preppy. I’m about to have breakfast with a preppy. AND I’m dressed in khakis with shoes that are essentially penny loafers with my hair combed. Holy fuck, am I turning into one of them?? I CAN’T BE. I’m a skater, gosh darn it! Ugh! What’s WRONG with me?? Why am I even still sitting here?’ In the back of his mind he heard himself saying to high tail it out of there. To slam his feet on his skateboard and zip away.

‘Go! Don’t let them get you!’

But he didn’t budge. Instead he drank some water to calm his nerves and tuned into Joseph for a moment.

“…and then I told Chad ‘Sure, I’ll suck your cock today.’ I mean, why wouldn’t I? Us good boys have to help each other out, right?”

Ricky nodded but thought ‘Da fuck?!’ The refreshing calm came to him and he pretended he didn’t hear it.

Joseph still babbled on, and Ricky spaced out again. But he couldn’t ignore it. ‘Jumpin’ Joey is not only a goody-goody prepster but he’s GAY now, too? For a guy named CHAD. How preppy. Why am I not leaving?’ More water.

Joseph kept on talking about this Chad, or something, and Ricky caught himself feeling his dick and loving the feel of the khakis on his legs. ‘GAH! NO!’ screamed his internal skater self, and he began to look around to distract himself. He started to think the decor the diner might not be a nostalgia place like he first thought, but would be more suited to a country club. Not that Ricky had ever set his skater boi foot in a country club, but it just seemed Iike how he’d expect one to be. Like he knew it should be way deep down or something. He gulped the last of his water. He looked around. Preppy guys there, over there. ‘Say, those polo shirts are pretty nice….WHAT?!…no, please no, I can’t. I won’t!’

Just then the bow tied server came and put their food in front of them. He filled Ricky’s water glass. “Enjoy, fellas!” said the server with the same blank smile that Ricky abhorred.

“Well, dig in, Freder - my apologies, Rick!” beamed Joseph.

‘Yes, food. Anything to keep my mind off what’s happening!’ Besides, he was suddenly famished. So Ricky did just that and took a big bite of the waffles.

“WOW!” he had to say aloud. “I’ve…I’ve never had waffles this good!”

“Told you,” winked Joseph.

Ricky shoveled it in and then leaned back a bit. He needed a moment, overwhelmed by the sheer tastiness of the food. And he felt unbelievably calm.

“So why did you do that to your hair?”

“You mean comb it?” asked Ricky.

“Hee hee. You’re silly,” he said again. Then in a concerned tone he said, “The coloring. It’s so unbecoming.”

“Oh, uh, I guess I thought it looked cool.”

“If I am not being too bold, Rick, it looks trashy. You’d do well to cut it off.”

“Er, maybe.” He was getting a little sick of it, if he was being honest to himself. Or did he just have that thought for the first time? He wasn’t sure. It just seemed like he was sure he should cut his bangs off. “Uh, yeah, sure, okay.” A voice in the back of his head said ‘No, bro, s’bitchin’ keep the frosted bangs!’ But he didn’t want to listen and just munched on more waffles.

“Loving the khaki look on you, but you should have a belt.”

“Yeah, that makes sense.” Munch. Well, it did… right??

“You’d look better in a collared shirt,” suggested Joseph.

“Oh I would?” Ricky had meant it to be dripping with sarcasm, but instead it came out as sincere interest and ponderance.

“Yes, indeed.”

“Okay,” Ricky heard himself say. That part in the back yelled out, ‘Hey! Da fuck?! Like that’s gonna happen. Why’d ya say YES, jackoff?’ “It does look good,” he thought, looking around seeing all the collars on the swell fellas. “Sure!” The skater inside cried out ‘No!’

Ricky had finished the waffles and moved on to the bacon. The bacon. The best. No contest. And as can be expected, it didn’t last long. Heck, regular old bacon is hard not to scarf down. When it tasted this good, you have to recuperate. And Ricky did just that, feeling that clean, satiated feeling.

Joseph pulled him back with another comment. “You know what? It’s not just your bangs that look sloppy. Your hair’s so shaggy and unruly. I mean…Rick…it’s down to your shoulders, for goodness sake! You’d actually be better off with a different haircut altogether.”

“Yes, I’d do well to get a haircut.” The inner skater boi said, ‘Youz crazy, bro! Don’t touch your locks! If anything bleach it all! But don’ fuck wif-’ “What do you recommend, Joseph?”

“Well, your nice natural chestnut color would look great with a slick Ivy League cut with a side part.”


“Sure. From the pomade.”

‘Pomade? POMADE? Can’t even imag-’ “Yes. Yes, I would look great all neat and trim. And styled just so. I’ll do it. I don’t want to look like a slob.”

‘Yes! You DO! Yer all rebel n’shit. Yer a SKATE-’ But the thoughts of the guy sitting in the booth at the country club atmosphered diner drowned out the protests of the guy who walked in. And the thoughts that flooded his head were of himself in a snazzy new Ivy League haircut, pomaded into side part perfection.

Rick’s dick pushed against his khakis, harder than ever. With one hand he squeezed it and with his other he went to the cup with the poached egg. Ricky had never had one before. They always looked gross to him. But he figured try it, right? As he spooned in mouthful after mouthful of his new found favorite way to have eggs, all the while feeling totally scrambled inside, he heard his -friend?- across from him.

“So, Rick… what do you say we get you into a nice oxford shirt right now?”

“How would this be accomplished?” ‘ARGH! Who even TALKS like this??’ wondered the weakened skater boi still lurking about.

“Well, it just so happens that under this diner is a warehouse. It’s chock-full of stuff. We’ll give you something that suits you.”

“Neat! But you don’t mean for keeps?”

“Oh, certainly. But not necessarily for free. The rule here is the new togs are yours if you help out a friend.”

Rick downed the orange juice. “Is that all? Sure, let’s go put me in an oxford!”

The skater boi trapped inside squirmed and squirmed. ‘This can’t be happening! How is this happening? Why am I agreeing to all this???!!! ARRRRRRRR!’

But Rick followed Joseph to the back room and down some stairs. The preppy did not lie, but of course. A cornucopia of conservative clothing. Everything a guy could ever need to be preppy. His mind’s eye were covered by hands, but his own hands touched the soft fabric of the button down long sleeve shirts in the aisle which Joseph led him down.

“I think we should start with something classic. An introduction, if you will,” smiled Joseph in that way. He unhooked the hanger of a light blue shirt.

“Yes, classic,” repeated Ricky. He found himself practically ripping off his stained oversized T-shirt with the logo he barely recognized, didn’t matter what it had been, just so long as he had that little pony on his chest instead, and eagerly put on his new shirt. He carefully buttoned each button, save one at the top.

He then felt hands around his waist. It was Joseph, slipping a black belt through the loops of his pants. Ricky couldn’t recall the last time he wore a belt. In fact, he didn’t even think he HAD one; Then Joseph led him to a full length mirror.

There stood a young man. His neatly combed hair definitely needed a haircut, but overall he looked quite snazzy in his Ralph Lauren blue oxford, black belted khakis and spiffy sneaker shoes. This young man was positively preppy looking. And he was looking at himself!

‘No! Nooooooo! I shouldn’t be dressed like this! I’m not a preppy!

But Rick’s reflection showed one of those plastered smiles.

“Golly, you look SWELL, Frederick!” Then with a little too much enthusiasm, Joseph said, “Ready to help me out?”

Rick turned around and watched as Joseph unbuckled his own belt, unzipped his khakis and pulled down his tighty-whities. His big cock sprang out, angled up and hard as a rock. Rick recoiled. But Joseph just stood there waiting. Grinning. Rick couldn’t help but stare. And slowly his body moved without him telling it to.

“That’s right. Us good boys have to help each other out. You want to be a good boy, don’t you Frederick?” Joseph stoked himself sensuously a little, enticing his new friend.

“Yes,” Rick heard himself saying, and it seemed he could do naught but ease his lips onto the preppy’s cock.

“That’s right, suck me. Be a really good boy, and you get to keep the belt and shirt. Thhhaaaaaa-AAAHH—at’s a gooo-OOO-D boy!”

His head moved back and forth, slurping over the shaft of his preppy pal. If he did this, he’d get to keep this great feeling and good looking collared shirt! His lips passed over Joseph’s rod again and agai, back and forth and Joseph’s load readied itself for expulsion.

Faster and faster until it seemed to knock some sense into him. Too bad he could do nothing to stop it, though, as if the syrup from the waffles had gummed up his ability to do so. But the die-hard skater that seemed to be dying did panic.

‘NO! NooOOOoooo! This CANNOT be happening! DA FUCK! I… am… sucking… some… guy’s… DICK!! I am NOT gay! WHY am I—DA FUCK, BRO??’ Was that a tear in his eye? Or was it from joy? ‘nO!!’ The inner skater was hyperventilating. If he was unable to stop himself from slurping up the cock and tasting the precum, he had to make sense of it. ‘Uh… uh… it’s not gay if I didn’t start it, right? It’s not like I asked HIM to suck MY dick. So I’m not gay, this doesn’t make me gay…right??’ The skater desperately tried to convince himself of this, but he never fully did before he guzzled down Joseph’s hot white syrup.

Ricky awoke, breathing heavy. It was dark in the room, but just enough light from the cityscape outside coupled with the familiar feeling under his reclining body let him know he was in bed. He didn’t remember ever coming to bed. His breathing normalized as he calmed down. It was just a dream. Just a dream. He clutched his chest. ‘WAIT,’ he panicked. His fingers pressed into a cloth different than what he was used to. He didn’t want to admit what it felt like. He darted up and turned on the light.

“GAH!” There he was, oxforded, belted, khakied and loafered.

If he really had these on, then it had not been a dream! None of it. He really DID –he gulped. ‘Fuck. Fuck.’ He didn’t know how he got here, but it didn’t matter one whit. This time the skater boi had control. Though he’d been all thumbs trying to get the shirt’s buttons undone, he did manage and he tossed it across the room. He literally kicked off his “kicks” and frantically struggled with the belt. Finally it unhooked and he stripped himself of the chinos.

He stepped a few feet away and pressed up against the wall. He started breathing heavy again, but this time from relief. He was free of that preppy shit. His gasps slowed down and he tousled his hair into the shaggy mess it usually was. He ran to the face-high mirror on the wall and checked. Yup, frosted bleached hair, down to his shoulders going any which way.

He staggered into the next room and shot his eyes to the corner. There they were. His kicks. His REAL kicks, the ones he loved. The ones his skater friends approved of. “Koz dat’s whatta’am. SKATER RICKY.” He leapt at the skate shoes and scooped them up. Sure, it was weird to hug and squeeze them close to his chest, but that’s exactly what he did. He loved these sneaks. “My KICKS, yo!” He didn’t know how long he sat there rocking back and forth clutching his beloved kate shoes to his heart, and he didn’t care. No one saw him, so he did it until he felt normal. Like Skater Ricky.

‘And Skater Ricky needzta gear up, yo.’ And that’s precisely what he did, He breathed a huge sigh of relief when he found his skateboard by the door. Once again the young man stood in front of a full length mirror. He saw a SnapBack the wrong (that is rightfully wrong) way around with blonde poking out over the plastic, a loose fitting pit-stained regular ol’ T-shirt sporting the Thrasher logo, slightly sagging denim frayed at the edges by his cool Vans skate shoes. Their sure-grip waffle soles stepped sure-footedly on the grip tape of his magnificent skateboard. “Yeah, THAT’s me.”

The video games came on, with him rolling his board to and fro as he sat and he somehow managed to forget the whole thing. That is until his killed off yet another life in the game and jolted his head forward in disgust of his performance and noticed that those damned penny loafer sneakers were on his feet. “WHA DA HELL?” He had no knowledge of ever putting them on. Or even getting up. Not even to use the bathroom. He took quick short breaths, staring at the shoes. But he didn’t bother to remove them, seeing full well that his other sneaks lay strewn in that same corner. After a while he just continued to play his game and killing off his character.

Hours later he awoke with a jolt. Where did his cap go? He looked around, thinking it must have flopped off when he woke up just now. But it wasn’t anywhere around him. Puzzledly he scanned the rest of the room. There. With his sneakers in the corner. He found that he could only shrug, and rocked the board back and forth, rocking his ‘penny loafers’. And was he okay with it? Pretty much. Certainly a little less freaked out than when he discovered his legs were khaki again. Especially since he had absolutely no idea how or when this happened. And yes, the Thrasher shirt was tucked in neatly under the black belt. He sat motionless for a while, now truly afraid.

And then suddenly he awoke, of sorts, catching himself in front of the full length mirror, finishing up the last button of the classic light blue oxford, the collar of which rested against well-combed hair. Combed slick back and as best as he could into a side part, with water in place of pomade to hold the shape.

‘Da fuck, bro???!!!’ called out the skater inside, but Frederick didn’t listen. He could only think how he might look good with a tie. One of those ties with the big stripes. He wondered if they had a name other than big striped tie. “They must,” he said aloud as his mouth curled into one of those plastered smiles. He sighed deeply and happily. “Look at me. All prepped up.” The he frowned a bit. ‘Well, almost. Joseph is correct. I should have proper loafers,’ he sighed in despair as he looked at the sneaker shoes on his feet. ‘ I mean… after all… they’re…VANS. They’re gym shoes. I should have shiny leather loafers.’ He couldn’t stop wondering what they would feel like on his feet. He always imagined them as stiff, unforgiving and pinchy. But were they? What if they felt really good, like…like they hugged his feet? He had to know. He thought, ‘Gosh, I can always get myself a pair if I suck Joseph’s hot cock.’

These words shocked him, and suddenly Skater Ricky looked horrified at the preppy guy staring at his in the mirror. “ARGHH!!” He stripped again, and curled up in the fetal position.

“I’m a skater… I’m a skater…,” he cried weakly. He didn’t know what was wrong with him. Why couldn’t he shake the feeling that he looked good all prepped up? Why did he lick his lips craving cock? What was happening to him? And then he started to actually cry. He hadn’t actually cried since he was four and his mother told him he couldn’t have a skateboard. That Little Ricky in his wee little Vans Skate Hi sneaks had never even heard the word preppy. And now grown Rick couldn’t seem to quell this desire to be one.

He shook, crying himself to sleep.

The next morning he discovered himself on the floor. His mouth was devastatingly parched. Like, he needed a drink NOW, yo. As he fumbled for something to drink, he saw one of the bottles of water in reach. Gulp, gulp, gulp.

Skater Ricky found himself walking along headed toward the diner. Only he wasn’t really walking himself. That is it was like he was watching his body walk from afar. Somewhere distant. And also not himself due to those preppy togs and that plastered grin. ‘Nooo! NOooO! Gimme back control!’ But the preppy that he’d been trapped inside would not let him.

And before long he’d been just a few faux-loafered feet away from the door. As luck would have it, a good looking preppy guy came gliding out. He had a lavender Lacoste polo shirt, khaki shorts and Sperry Top-Siders. Rick thought he looked great, and not just the outfit. Gorgeous guy, he thought.

‘JEEZZUZ! NO! YA WANT PUSSY, DUDE!’ But it would seem the guy staring at the perfectly parted hair of this devilishly handsome preppy fellow didn’t even hear him.

“Greetings, my fine fellow!” came Rick’s voice.

“And good day to you!” But the enthusiasm seemed to wane as the little sentence came to an end.

“I do apologize for the unseemly coloration of my hair. And also for the mockery on my feet. But you see, I am just discovering myself as a good boy.

I’d really like a real pair of shiny penny loafers. Would you allow me to help you out so that I may obtain them from the warehouse below?”

“Well well! I’d love to help out a fledgling prep! My name is Chad.”

The young man in the sneaker shoes held out his hand. “Frederick.” ‘NoooOOoooOo!!’

Gorgeous blue-eyed Chad shook his hand vigorously and said, “Pleased to make your acquaintance, Frederick! Shall we adjourn to the warehouse?”

“Oh yes!”

A tear fell on the face of the internal skater.

They made their way past the smiling bow tied guy at the counter who gave Chad a wink as if he knew what was about to happen, and strolled past the pride of preppies enjoying their meals.

For the spiffy young man who followed Chad, it seemed like forever to get to the door of the warehouse. On one level the anticipation swelled and never seemed to arrive. On the other it had been like the long march to the electric chair.

When they came to the door to the warehouse, Chad opened it saying, “I’ll let you help me out on one condition.”

“Oh?” Rick said nervously. What could it be? How he longed to suck the dick of this hot preppy guy. “Please tell me of this condition, Chad.”

Chad didn’t speak, but went down the stairs. Rick padded behind him like an obedient puppy, all the way to the footwear section of the warehouse. But he didn’t come to a stop by the penny loafers. In fact, he passed them, and Rick moved right along with him. Chad’s grin came out when they got to the type of shoes that had hitherto always made Ricky want to hurl.

“Condition is I’d rather see you in boat shoes, Frederick.”

‘GAH!!!! FUCK no. Fuck NO!’

“Why golly, Chad. I think you’re right. I’ll gladly help you out for a pair of…Sperrys.” He only knew the name Sperry by reading it there in front of him. Ricky never knew. Ricky never cared to. He’d always tasted bile when he saw the goddamn things on guys’ feet. But now? Now he longed to wear them. And he imagined how delicious Chad’s cum must be. He’d be wearing BOAT SHOES! And all he had to do was suck off this gorgeous preppy! And he could be preppier himself! ‘AAaaaaaUGH!’ But Frederick ignored the scream inside of him.

Chad’s chino shorts hit the floor and Frederick zipped over with his O shaped mouth and gave the big awaiting big cock a tongue bath.

“That’s it, you preppy WANNA BE,” said Chad.

Still sliding his mouth greedily over this hot prepster’s dick, Frederick looked up with wondering puppy dog eyes.

In answer Chad said (as best he could through all the OOOs and AAHs of the intense pleasuring), “That’s right, boy. You’re NOT a preppy!”

Still sucking, Frederick looked even more desperate and pleading with his eyes. Chad properly read them as “What do you mean, sir?? I am preppy! How am I not preppy?! Please say I’m preppy like you!”

Skater Ricky perked up. ‘Ya mean… dere’s a way out!? I havenn gone too far?? I can stillz change back??’

“I’m as preppy as they come, boy,” Chad said, breathing heavily. He OOOOOO’d. “You’re doing a great job, boy.”

Frederick said, “Thank you, sir!”

“You wanna be preppy, boy?”

The sucking continued as the head nodded vigorously, which made Chad bite his lip.

“You think you’re prep, huh? Just look at you. We gonna get rid of that mis-colored mop, boy?”

More sucking and nodding. “ UH UHOOOOOO…”

“Give you a nice hair cropping to something respectable? Huh?! HUH!HUHOOOOOO!”

“You gonna wear Sperrys like a good boy?”

Slurp, nod. Ooooh.

“It feels SOOOO good, boy! Yeah…. Yeah…. And your new shoes will feel great, too! YeahhhhHOOOOOOOYEAH….”

Frederick wanted those boat shoes. So he sucked and sucked. He started getting tired, but Chad still had to squirt his prep juice. Chad noticed that the soon to be officially preppy Frederick got tired, and that’s when he grabbed the horrendos shag of hair and almost violently forced Frederick’s head back and forth over his fully erect shaft.

He spoke a word at each thrust forward, “Don’t… worry….we’ll… make… a … prep… out…of … you…that’s…OOHHHH…. Yeah… that’s….right… you’ll…be… a…prep…STEerrrrrrrrrr”

And with that gorgeous Chad thrust cock all the way to the back of Frederick’s throat and coated it in a burst of glory. As it happened, Frederick couldn’t help but think how the creamy substance flowing down into his belly must be as white as the soles on Chad’s Sperry Top-Siders which drew his eye like a magnet.

“Ooooohyeah,” said Chad, briskly pulling up his dick pants. “You’re a good boy.”

“Thank you, sir.”

“You want those Top-Siders now, boy?”

“Yessir. Please?”

“Why do you want them, boy?”

‘I don’t! I DON’T’ Even Frederick could barely here the weak voice.

“Because I want to be a good and better preppy than I already am, sir.”

“Good boy. I’ll tell you what…”

Frederick hinged on what would be said next. Skater Ricky trying to survive hoped that it would be a rejection.

“You did such a great job helping me out, we’ll give you a polo shirt, too.”

Frederick’s eyes widened. “Oh! That would be keen!”

‘No! Snap out of it! Don’t give in!’

“I get to select the color. Is that agreeable to you?”

“Yes, Chad, sir. I will agree to whichever color you pick out for me. Because I am just a fledgling prep and you are a proper preppy. I trust that you will give me the best prepster polo for me to wear to make me preppier. I hope to one day be as preppy as you!”

“Good lad! Don’t worry, Frederick. You’ll be a true prep QUITE soon.”

Frederick cooed. Ricky moaned. And moaned. Both boys inside watched Chad as he carefully paraded around, deciding what to give his preppy protégé. Chad finally grinned, and reached to unhook a Lacoste polo.


“Oh YES! Thank you, Chad, for selecting such a preppy color for me.”

“You will wear this PINK polo, boy?”

“Yessir!” A plastered smile, but the dying embers of Ricky flared out another moan.

“Why, Freddy?”

“OH! I like being called Freddy, Chad!” ‘No! DAMN you! FUCK you! RICKY!’

“Answer the question, Freddy!”

“Because I want to be a preppy, sir! And pink is a preppy color. And I will look good in pink, right, Chad?”

“That’s correct Freddy.”

‘RiiiiCKyy’ eked out what was left of the Skater Boi.

“Okay, Freddy, kindly remove those silly skater sneakers from your feet. The time has come for your new shoes.”

Freddy hurriedly worked his way out of them. ‘Don’t…they’re VANS!…noooooo.’

“And take off those smelly skater socks. True preps do not wear socks with their Top-Siders. You want to be a TRUE PREPPY, don’t you?”

“Yes Chad! With all my heart!” ‘No! Heart of a skater,’ said the crying boy inside. But the socks still got peeled off.

Chad lifted the lid of the box of Sperrys just under Freddy’s nose. The smell of the leather was intoxicating. Chad took the boat shoes ceremoniously out of their box and moved them to the floor but not before moving them slowly in front of Freddy’s face.

Freddy couldn’t wait. He’d be wearing boat shoes just like Chad. He would be preppy!

Chad said, “Standard mahogany brown, of course.” He paused. A little time passed. “You may slide into your Sperrys, Freddy.”

The preppy protégée wasted nary a moment and gently tucked his feet into his new boat shoes. They felt like second skin. They were right. They were preppy. Like him. He look down to admire them and saw the white stitching on the toes smiling up at him. And he smiled back with the vacant grin. Inside Ricky frowned. Freddy moved his feet around to get a better look from various angles. He loved the rawhide stitches. He loved the white sole. He loved them!

“You look great in them, Freddy!”

“Gee, thanks for saying so, Chad. I really hoped I would!”


But Freddy didn’t. He just beamed and beamed.

‘Hooray! I’m wearing boat shoes!’ thought Freddy.

‘FUCK! I’m wearing boat shoes!’ thought Ricky.

They looked terrific just under his chino slacks. But perhaps a little casual for his blue oxford. But here came his preppy pal Chad to fix it.

“Okay… Ready Freddy?”

Freddy nodded. Ricky tried to shake the head vehemently in protest. But it did no good. Instead that smile mixed with a little eagerness crept onto his face.

“Okay, you prep, take off that oxford. We’re going to outfit you in a polo. Ever wear a polo before Freddy?”

‘No! Never! Ain’t gunna! You can’t DO this to me!’

“I surely have not, Chad. But I can’t wait!” He deftly unbuttoned the oxford shirt. He stood bare chested and he watched Chad check out his body. It felt good to be admired by his preppy pal. Good like deck shoes on his feet.

“Put your sexy arms up. You’re about to be covered in pink!”

‘AAUUgggGgghHhhH!’ “Mmmmmmm!’

And with that, Chad pulled the polo over his preppy brother’s frame.

Ricky always imagined polo shirts to be stiff, scratchy and heavy. But Freddy now basked in its soft, breathable comfort. The pique fabric caressed him, and something stirred in him. And it wasn’t his old skater self pounding to be set free of this nightmare.

‘PINK! Imma fuckin’ pink preppy prick!’ And the tears streamed down his cheeks.

But Freddy’s cheeks were raised high and glowing. And his other cheeks looked great in his khakis. He didn’t even have to be told to tuck his polo into them.

“Love it, my brother!” said Chad, unclasping Freddy’s belt and pulling it out. The chinos were fitted enough that they didn’t drop, at least long enough for Chad to reverse the belt to a deep brown and reloop it and hook it, giving Freddy’s crotch a quick pat. “Do you know why I did that, Freddy boy?”

“Because my belt should match my shoes!” he answered, pleased with himself.


“I’m about to do something, Freddy. But I must warn you. Once I do this, it cannot be undone. Not the little event itself, but both the affect and effect of it.”

“Okay, Chad!”

The scraps of Ricky began hyperventilating again.

“Are you sure you want me to do it? You’re positive you want to be preppy?”

“Oh yes, Chad! It is my fondest wish to be a prep. I need to be one. I can feel it my bones and boner. I’ve always been a preppy deep down.”

‘NOoo! Don’t do whatever da fuck it iz! I don’ wanna. Imma skater! I wanna wear sneaks! I wanna skate!’

Chad put his hands on either side his friend’s neck and slipped his fingers under the curl of the soft triangle-like cut of the shirt.

‘NOOOO! NOOOO! Pl-please!! StOP!’

Chad lifted the fabric gently for a moment and looked into the Freddy’s eyes. He could almost see the screams of Ricky inside. But he just grinned that blank grin.


The collar of the pink polo now stood straight up, and Ricky had popped along with it. He was gone for good.

Freddy smiled the plastered smile, a blank slate ready to absorb more preppiness.

Chad asked, “How do you feel, Freddy?”

“PREPPY!” And he DID.

“You know, your popped collar will look much better with the short hair you promised. Come with me, Freddy,” Chad ordered. “I’ll take you to the barber we all use. He’s an expert in the Ivy League cut.”

“Wonderful,” said Freddy with his vacant smile. “I must say I am truly embarrassed by my hair. What a bad kid I had been.”

“No worries. That’s all over with now. We’ll get you looking like the rest of your preppy brethren soon enough,” Chad told him.

“Keen!” smiled Preppy Freddy.

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