Cottagecore: Road Trip - Dan

By Jon McGee

Published on Sep 20, 2024

Gay

Cottagecore: Road Trip Chapter 15 – Charlie B

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I woke up early, curled around Charlie. We'd crawled under the bedspread during the night, but it was pushed down to our waists. The room was stuffy even with the windows cracked and light rain falling outside.

Charlie stirred when I climbed out of bed and woke more fully when I crawled back in some time later.

"You're freezing," Charlie murmured when I spooned up against him. I nuzzled his neck. Slowly at first, he began to kiss me back. Before long, I had Charlie onto his back. I took his cock in my hand and added some lube.

Charlie's eyes widened when I straddled him, and he gasped when I slid his cock balls-deep inside me.

I started slowly, just grinding a little, thumbing Charlie's nipples, leaning down to kiss him. I have to admit, I wondered if I hadn't tried to take too much too soon. Charlie's cock was so thick at the base that I probably should have used my largest dildo to get ready. It was longer than Charlie, but almost as wide at its base. I tried to keep my face from showing any pain.

Charlie started thrust a little, or at least he tried, grinding into me while I was bottomed out. Mostly he let me control the motion. I adjusted to meet his girth pretty quickly, thank god.

As Charlie woke up, I began to arch my back to grind his shaft against my prostate. I hoped the surf drowned out some of the noise I was making, but it felt so good that I didn't really care.

I don't think my cock has ever looked larger. I swear, if I've ever measured eight inches it was riding Charlie that cool, damp morning. Every nerve in my body felt like fire.

After a few quick strokes when I started to ride Charlie, I didn't trust myself to touch my cock. It stood straight away from my belly, 90-degrees, with my dickhead swelling out of the foreskin, precum flowing down my balls and onto Charlie's chest.

Charlie reached out go stroke me, but I intercepted him. I took his hand and kissed his palm and pulled his first two fingers into my mouth. When he reached for my cock with his other hand, I pinned his wrist to the bed.

"Don't touch my cock or I'll cum right now, " I warned. "I'll shoot hands-free as soon as you cum. I'll riding you after I finish, but I want us to cum together."

"So fucking hot," Charlie groaned, grinding the base of his cock against me. I bent down and kissed him again.

I kept riding, one hand pinching Charlie's hard nipple, the other against his chest, keeping him pinned down. Whenever his breath got ragged, I sat up and stopped moving. My cock jutted between us, my dickhead fully free from its foreskin now, precum pooling on Charlie. He groaned in frustration and ground into me. I didn't start riding him again until I was sure he wouldn't cum.

I rode Charlie's fat cock for more than half an hour. My thighs burned, my back ached, and I could have cum ten times. Maybe half the time I slowed down, it was to keep me from cummings right along with Charlie. He whimpered and moaned and thrust into me, but I slowed down every time he got close. I kissed him, pinched his nipples, and ground down on his cock to keep him from trying to finish before I was ready.

Eventually, it was time. "Now," gasped Charlie.

"Now?" I kept riding.

"Now!" Charlie was trying to slam into me, as much as I allowed it.

"You sure?" I gasped, teased. I ground down hard to keep Charlie from thrusting. Oh god, I was about to cum from grinding down!

"Sure!" gasped Charlie.

"Really sure?"

"Jon!" shouted Charlie. I felt his cock swell. He slammed into me hard, screaming my name again. I felt his first shot splash inside me.

Charlie grabbed my arms and flipped me onto my back. He threw my legs over his shoulders, grabbed me by the biceps, and pinned me to the bed. He shot with every hard thrust. I felt each hot jet deep inside me.

Charlie's fist thrust set me off. Hands-free, I sprayed cum against my forehead, Charlie's chin, my chest. Even after I was done shooting, I kept cumming. Dribbles and oozes spattered my chest and pooled on my belly. As my orgasm slowly subsided, I gripped Charlie tight with my knees, trying to hold him inside me, but he pulled out slowly, gasping and moaning and shaking.

"Too sensitive," he groaned, swatting away my hand when I reached for his ramrod cock. He lay on his back, panting. Instead, I massaged his loosening balls wanting to suck him clean but knowing he was too sensitive. I used the corner of the bedsheet to wipe some of my cum from Charlie's face. We both laughed.

I collapsed against Charlie's side, trying to control my breathing. Before I knew it, I was fast asleep.

"You're about to launch your brand at A. Ham," Charlie asked a few hours later, while I waited on Second Lunch. "What'll it be?"

I shrugged. "I'm just . . . me."

"Well, that's one kind of brand," said Charlie, "but is it the right brand for you?" He was in full marketing mode. He'd told me how seriously he took his education and career plans, but it was easy to forget when we were just hanging out at the beach.

I didn't know what he meant and said as much.

"When somebody start college, especially where most students are from far away, they're a blank slate. You could show up as `Just Jon,' like you said, or you could totally reinvent yourself into the Jon you've always wanted people to see, or you could do something in between. Most kids at NYU did some reinventing. Whatever you chose, how you present yourself-- your A. Ham. persona--that's what I'm calling your brand."

I was trying to get my head around what Charlie was saying. "Reinvent myself? That sounds . . . fake."

"Only if your aren't honest," he said. "If you decided you're suddenly a rave kid or hardcore jock, it would be phony as hell. I mean, unless one of those `Jons' is waiting to burst out of your closet."

"It is almost sportsballs season," I fake-scowled. "Maybe I'll go out for the football team."Charlie humored me but said, "that'll be tough since A. Ham. closed down its football program during the Great Depression. But if you think it's the right brand for you, maybe try out for wresting. You're a natural one-on-one, jock-o."

I threw a fry at him. "Why shouldn't I just be me?"

"Which version of `you' you want people to see first."

That still didn't make much more to me. "How many versions of me do you think there are?"

Charlie rubbed his hands together like he was finally getting somewhere. "So many choices! How about scientist extraordinaire, like Sheldon Cooper Jon, but not an asshole? Or Mr. Natural Jon, hippie dippy yoga hottie? Maybe California Jones Jon, scientist-explorer-backpacker-rock climber? Or that National Treasure guy, unlocking America's historical mysteries with good-looking daring-do."

I started to get annoyed, but I knew Charlie was joking to make his point.

"Those are all roles," I said. "Even if they're based on stuff I care about, none of them are my genuine identity. Fake as hell, like you said."

"I'm just saying, there are lots of versions of Just Jon.' You can take the easy way and just . . . show up' next week. Or you could put some effort in."

Charlie knew he sounded judgy, but I finally started to see his point. "You think I'm not putting enough effort into A. Ham.?"

"Like you told the guys at the beach," he said after thinking for a second, "you've been focused on other stuff this summer. But yeah, it seems to me that you put a whole lot more into planning your road trip then you've put into getting ready for A. Ham."

He wasn't wrong, at least not entirely. "I've been thinking about thinking about it," I said a little lamely.

"Sure," said Charlie encouragingly. "You met your roommates, you've thought a little about classes you might take, that's all good. I don't know that I did much more before I got to NYU. I guess I'm offering some advice like what I wish I'd been told, kind of like the guys at the beach. I'm no Elder so I'll shut up if you're not interested."

That's not what I wanted, and I said so. "I care more about your advice than what the Elders told us. As fun as that was. I just wonder how many first years will try on a `new' persona at school."

"I'll bet a lot of students will show up as the bestest, smartest, mostest prepared version of themselves, even if that's not who they are at home. Maybe most students. I know I did some of that, probably everybody does. Well, probably everybody but the prep school kids," said Charlie, grimacing.

"Go on," I said with a look.

"The preps will all know each other, more or less. Some will be normal, but if A. Ham. is like NYU, a lot of them will lean hard into their prep identities." I shrugged to say I didn't know what that identity was. Other than Quiddity and Tee's mention of Duxbury, I didn't know anything beyond stereotypes.

"It'll be the core of their brand,'" said Charlie. "You'll be able to tell from how they dress, their hair, their nicknames . . . "--Allen's brother had said something about nicknames--". . . so their topline brand will be prep,' and their specific brands will be Dannington Academy, excuse me The Dannington Academy, or Holden Hall, or wherever they went to school."

"That specific?"

"Maybe not to you, but they'll be able to tell who went where from little things. Red socks with suede boots for the Beasley School, or green Patagonia vests for Braintree. They all have a tell, if you know how to read it."

"Their brand is the high school they went to?" I assumed that Charlie knew the doubt in my voice was directed at these prep school kids, not him. "That sounds . . . weak."

"It's not just their identities, it's their families' identities too. Or at least part of them."

"Weird," I said. "I must be missing something. Their parents' status is their own?" My school was too small to have much of a social hierarchy, especially based on their families. Maybe parents' Park Service rank meant something to our teachers, but not to us.

"It might not be that way at A. Ham," said Charlie. "It has a reputation that they won't allow easy admittance for legacy students, blah, blah, blah. But if it's anything like NYU, there'll be plenty of kids whose brand doesn't go beyond `prep school kid.'"

"I think I'd be ready to move on," I said. I liked my high school well enough, but I couldn't imagine letting myself be defined by it.

"It's not like that. They aren't looking backwards," Charlie said, thinking as he talked. "Going to the right' school just reinforces their brand within their world." Charlie must have seen that I didn't really follow him, so he kept explaining. "It's one thing to say, Percy went to Harvard Law,' but just about anybody with good grades and high-test scores can so that."

"With a little luck," I said, thinking about Henry and Pete.

"It's another thing entirely to say, I'd like to introduce you to Percy, A. Ham. undergrad and Harvard Law.' For a lot of people, it's another level entirely to say our Percy prepped at The Hotchkiss School and then went on to A. Ham. and Harvard Law.' It makes dear Percy bulletproof for the investment bank or law firm or society wedding."

"And here I was thinking prep school kids are just rich and dumb."

"Plenty are," said Charlie. "Or not dumb, necessarily. `Entitled' is better. They lack drive, curiosity, initiative. They're raised with generational wealth and every privilege you can imagine. Combined with well-educated families surrounded by others who're all raised the same way, some of that socialization rubs off. Even the idiots will know some stuff. At least the ones at A. Ham. will."

I shrugged. "Not my world," I said. "I couldn't care less." Only about ten percent of A. Ham's students went to traditional prep schools. When I was on campus last spring, they'd gone out of their way to emphasize how little impact prep school culture had on student life at A. Ham.

"I didn't mean that you should," Charlie said. "We got a little sidetracked. But they make a good example of how much information about your brand you can convey without any real effort. In this circle, a certain haircut and a few accessories tells you everything there is to know about them."

I laughed. "Or at least, everything they want you to know. You aren't saying I should prep it up, are you?"

Charlie shook his head. "Lord no," he grimaced. "Prep school fakers are the worst."

I wondered what Charlie meant.

"You can't fake like you know the prep school world. Generations of learning go into looking that carefully sloppy. You could buy the exact same wardrobe, style your hair into that exact same mop, do everything just like them, and they'd still spot you a mile away."

"Good thing I don't want to look like a prep school kid," I said.

"Don't get me started," Charlie laughed. "I'm just using them as one type you can expect to find when you get to A. Ham., and also how you can tell a lot about yourself by your choices."

Henry had said something about projecting confidence when I got to school. "First impressions do matter, is that what you're saying? God, I sound like my mother."

Charlie laughed. "You sound like my mother too. But yeah, that's some of what I'm getting at. What do you want as your first impression? And not just on your first day. You'll be making first impressions all four years."

"I hadn't given it much thought," I admitted.

"It's about time, right? This time next week you'll be driving up to school."

I groaned. I really had been putting off thinking about A. Ham.

"Think of it as another form of mindfulness," Charlie suggested, tying his brand pitch back to a conversation about yoga we'd had the day before.

I wasn't sure I agreed with his comparison, but I saw what he was getting at. "Maybe intentionality more than mindfulness," I suggested.

Charlie nodded. "Right, choosing how people see you, conveying yourself deliberately."

"But I have to do that authentically, don't I?"

Charlie shrugged. "Sometimes it's part put-on. Project how you want to be seen, even if you don't feel that way inside. Fake it until you make it."

"What, pretend authentic?"

"If you tell the right story, you'll really stand out."

"But if I do it wrong, I'll look like a faker. A fool."

"Well, don't do it wrong," said Charlie with a smile.

I didn't say anything. I was trying to process the conversation. I'd been rolling the Elders' advice around in my head, starting to get excited about the start of school, but I was starting to feel a little nervous talking with Charlie. His focus on clothes and identity and brands made me feel like I was about to take a test I hadn't studied for. I didn't know any of the rules.

Charlie interrupted my spiraling thoughts. "Did I lose you?"

"I don't know anything about any of this," I said, more than a little frustrated. "I don't even like shopping." Charlie gasped melodramatically. "I get what you're saying about my brand, but I can't even imagine how to put everything together in a way that won't make me look like I'm trying too hard."

"Well, that's not the end of the world," said Charlie smiling. He was trying to tell me not to overreact.

I nodded to let Charlie know he hadn't lost me.

"What I'm saying is, you could drive up to A. Ham. with your cute raggedy-assed beard, and your look how hard I don't try to try' clothes, and you'd be Just Jon,' the road-trip adventurer, rugged outdoorsman, earnest student just looking to settle in. That's authentically you and it's nothing to feel worried about. But," he paused, "maybe we could be a little more intentional in how you project yourself."

"We?"

Charlie laughed. "You don't think I'm telling all this to you just without any plan, do you? Of course I can help with all that, if you'd like. This is a roundabout way of me offering. And I have a friend who might be able to help."

I felt a wave of relief. And then annoyance. "Who are you calling raggedy?"

Charlie's eyes sparkled. He was having fun. "Have looked in a mirror lately?"

I bumped his shoulder with mine, maybe a little harder than necessary. "I take care of myself okay," I said.

"Mm-hmmm," said Charlie. "This from the guy whose shampoo, conditioner, and body wash are all in the same bottle?"

"Hey!"

"From the guy who has literal holes in his underwear?"

"Nobody sees my underwear."

"From the guy who grew a beard only because it's easier than shaving?" He said "easier" like it was a character flaw.

"You try shaving with cold water in the back of a truck when it's raining outside!"

"From the guy whose dress shoes are hiking boots?"

That wasn't fair. Charlie had admired my boots, freshly cleaned and oiled, just the day before. "You like my boots!"

"They're very nice. For hiking. But anyway, aren't you the guy who gets his hair cut the mall sports clips places?"

"Maybe I'll find something better in Albany," I said. I wouldn't tell Charlie, but he had me there. My hair was already looking a little shaggy, even though I'd had it cut less than two weeks before.

"What I'm saying is that you look like a road tripping hippie," said Charlie. "For a road tripping hippie, you take care of yourself. For your introduction at A. Ham., I think you can do better. Hell, Jon, I didn't even know you're gay at first. I mean, unless that's what you're going for, passing."

Gaydar again. Mine was getting better, but I took Charlie's point that my style didn't really say much about me. I honestly hadn't thought about how my look communicated my sexuality.

Charlie was having a little fun at my expense, so I decided to have a little fun with him. "What does any of this matter, so long as I'm comfortable That's what's most important isn't it?"

Charlie pretended to clutch his pearls, gasping. He knew I wasn't serious but he played along. "You're right, I suppose," he said breezily. "You saw the caftan Eric threw on when we were leaving the beach yesterday? We could find you a whole wardrobe of them. I'm sure they're very comfortable."

"Do they make dressy caftans? Sparkle caftans for the First Year Dance? Business-casual caftans for my academic meetings?" I said. "It'd be sort of like Hogwarts' robes."

"Quizas," said Charlie with a fake-thoughtful air. "Or, if caftans won't work, there's an Agita outlet a few towns over, I noticed. They'll have plenty of the dressiest track suits. Even sparkly ones, I'll bet."

All the jokes cut the tension. "Tempting," I said. "Assuming I don't go the caftan route, what's your plan?"

"What do people see first? Clothes, haircut, styling, right?" I frowned. "It's superficial, but it creates your first impression. Based on what you've said, that didn't go so well with your roommates."

I'd told Charlie about the Zoom. "Allen wasn't impressed but nobody else said anything."

"What do you think `Cutie' thought?"

Charlie loved calling Q and Tee "Cutie," which he said was their Influencer Brand.

We'd watched some of their posts together, which I found remarkably unremarkable: the boys bathed in natural light, intertwined or holding hands, lip synching pop songs or "meaningful" movie dialogue. Sometimes they were just "vibing," according to Charlie, gazing into the camera, or looking at each other, conveying a mood. Beautiful, tasteful, and vapid, I thought.

"Gorgeous boys, stellar production, consistent output," Charlie had assessed their content. "Minimal scripts but well put together, especially for high school students. Their videos are high quality; they work hard for their clicks."

I groaned at "Cutie," which Charlie said was one of the weakest aspects of the brand. "It's okay for lovey-dovey kids," he'd said, "but they'll need to sex it up or make some other big changes if they want to keep the eyeballs over time. Sooner or later, they'll need to age up the content if they want to stay relevant. Fashion is a natural choice, or maybe fitness."

"Probably not politics," I said, remembering that Quiddity's mother was a Senator. That would take some getting used to, I thought.

Charlie shook his head smiling. "Political branding is really different than what I've focused on.

Superficially, he should cause his mom all sorts of problems with her base. I mean, he's really gay, and his boyfriend is Black, but her voters don't seem to care."

"I don't know what they thought of me," I said. "It almost like they were performing for us rather than interacting, or at least, that's how it felt with Quiddity. Tee seemed more genuine. I take your point, though. They weren't openly nasty like Allen but based on these videos, I doubt they'd think much of my style."

"Such as it is," joked Charlie. I threw another fry at him.

But Charlie did have a point. After two months on the road, my clothes were, to put it charitably, well-worn: faded, stained, stretched out. I'd also added some muscle, so they didn't all fit great. I'd always planned to pick up some new clothes before school, so why was I resisting Charlie's suggestion?

"Evan and Justin didn't seem to care," I said, but it sounded like an admission of Charlie's point.

"We're circling around the most important question," said Charlie. "I think I know the answer, but I want to hear it from you. Do you care what people think?"

"Do I care what my suitemates think about my clothes? Or what they say about me? Not really," I said, and I sort of believed myself.

Following fashion and trends had always seemed exhausting to me. I hadn't tried in high school, but mostly because there was no point. And now, I wasn't even sure how to do it. At the same time, I didn't want to stand out as a slob or a hick. I said so to Charlie.

"Okay," he said, circling back to persuasion mode, "let's think practically. What will you wear on the first day of class? Not a faded tee shirt and gym shorts, right?"

"I hadn't planned out my outfits on a daily basis." I knew I sounded mulish.

"It's a few weeks away," said Charlie generously. "I don't know what I'll wear when I go back to classes either." I wasn't sure I believed him. "What about your first meeting with your faculty advisor. What will you wear? I don't necessarily mean specific outfits, but how will you dress?"

I thought for a second. "A little dressier than normal. Maybe a polo or button-down shirt. Nice shorts if it's hot, probably jeans or khakis otherwise." Were there any other kinds of pants?

"Chinos, babe" said Charlie, making clear he was queening it up a little for emphasis. "Khaki is a color. Jeans and chinos is what you might wear. Khaki colored chinos."

I rolled my eyes and laughed. "I was going to do some shopping online to get everything delivered before I head up to campus."

"Mm-hmmm," said Charlie dubiously, "you could do that. Hey, you said there's a Presidential Invocation on your first day of orientation, after you're all moved into the dorms. And a dance, too, right? What'll you wear?"

I smiled a harrumph. Half-way between a smile and a grimace, maybe. I felt like he was cornering me, but I didn't mind. "Dunno," I said. I was getting close to admitting he was right.

"Do you have a suit?"

"I have a jacket. I'll wear it with khakis and a tie." Charlie arched an eyebrow. "Fine, chinos. Khaki colored chinos."

"That'd be okay," said Charlie, making clear that he though I might pass a minimum threshold. "I'll bet the prep school boys go that route, mostly. Part of their brand is trying to look like they don't care about how they dress."

"Are you saying the convention is a suit, not pants and a jacket?"

"I'm not sure about A. Ham., but at NYU, we wear suits for anything formal or important, like a presidential address. I think A. Ham. is probably stuffier than NYU, but anyway, it's easier to pass if you're overdressed than underdressed."

"Pass?" Charlie had said that before.

"Blend in with the crowd," said Charlie. "Pass by without standing out. Unless you want to stand out?"

It had never occurred to me that I could be a guy who would stand out by my clothes. "Is this your very long way to tell me you think I need a makeover?"

Charlie smiled. "You care a lot about being `Just Jon.' I didn't think you'd react well if I just came out and said it."

Charlie was right, I thought. Without his coaxing, I'd probably have just said "I hate shopping."

"So?" asked Charlie, "what do you say to a little glow-up?" He grinned, his eyes glittering.

"You'll help me?" I laughed. "You know I don't know where to start. You've seen my clothes."

"Such as they are," Charlie sniffed, teasing.

I decided not to dignify his point, but he did have one.

"Is this really `brand' thing just an excuse to make me go shopping?" I asked.

"I don't want to make you do anything," Charlie said. "Anyway, one cannot be made' to go shopping," he continued, like he was speaking from a place of deep wisdom. "You either shops, or you don't shop, there is no middle ground." You could just buy some clothes,' but that's not proper shopping. Mindful shopping. Intentional shopping."

"I hate shopping, of every sort."

"We'll see about that," said Charlie before he turned a little more serious. "Here's the thing. All jokes aside, I don't think you--the Just Jon I've got to know this week--shows through the Just Jon you look like. Maybe it isn't a big deal to you, but I think the A. Ham. environment will be just as judgmental as NYU. I want people to see the Jon I've gotten to know."

"I don't know where to start," I said a little lamely.

"I have a plan, if want to hear it. And a place to start. I've called in the big guns."

"There are things I'd rather try more," I said in a low, sexy voice. "What about these 'big guns?'"

Charlie rolled his eyes. "Horndog. Plenty of time for that later."

I leaned forward and said, "there's plenty of time right now."

Charlie snorted. "Here's what I think we should do," he said. "Based on those clouds"--he gestured over my shoulder with his chin--"there's more rain coming. Let's go back to your cabin, snuggle up in bed, and I'll show you some styles I think you'd like. Like I said, I have a friend who can help but we need to get to work now if we're going to pull it off."

"I like the snuggle in bed part," I said, trying to distract him.

Charlie ignored my seductive efforts, such as they were. "It's supposed to rain until tomorrow morning.

I have a friend from college who runs a clothing brand who invited me to come by tomorrow for a fitting for some things he thought I might like. It would really work for you too. C'mon."

As the first wave of rain hit us, we made a dash back to my cabin.

Half an hour later, Charlie and I were under the covers, disappointingly mostly dressed, looking at his laptop. Rain pounded the cabin's roof, drowned out by regular thunderclaps. I wasn't going for a run today, that was sure.

First, Charlie pulled up a folder from one of his fashion merchandising courses. He opened a page of thumbnails showing images from fashion shows. Handsome men, or striking men, or interesting looking men, usually photographed from the front. He did something to jumble the photos, mixing different designers and shows.

"Let's get a sense of what you think looks good. These are all from fashion runway shows, but most of the photos will be more ready to wear and less high fashion. What do you think of this?"

Charlie's next image showed a man in trim pants and an oversized jacket, covering what looked like a button-down shirt, paired with cowboy boots. All the clothes were made of the same green fabric, maybe cotton or a blend.

"It's so . . . green. Way too matchy. Pass."

"Sweet, literal Jon," said Charlie like I wasn't there. "Point taken. I'd never suggest you dress entirely in green, but let's back up. A lot of what gets shown at fashion shows is part of a story designers want to tell. Only some of the clothes are for wearing. Try to ignore the storytelling and just tell me what you think about each piece."

I looked at the photo again. "I like the pants," I said. "They're tight enough to show off his figure but they're not skin tight. The jacket's too big. Too much fabric. I'd get annoyed wearing it, plus it looks like a costume. I can't tell about the shirt, other than that I don't like that shade of green. Swampy. The boots are too clunky for the pants."

"The pants aren't too fitted? Your jeans are all pretty loose."

"Everybody wears 501s," I said. "Well, that or Wranglers. I don't think I've ever really thought about it. I know I hate the skinny jeans the goths wear, but I guess I like how these fitted jeans look more than my Levis."

"I agree with you about the boots," said Charlie. "Every model in the show wore them, it worked better with other outfits." Charlie clicked to another photo. "What about this?"

The next picture showed a man dressed in light gray pants made from a soft, drapey fabric. On top he wore a darker gray shirt, also loose, under an oversized gray sweater open at the front with a large collar. The sweater was another shade darker than the shirt.

"For this, I don't mind that it's all gray. I feel like they work together since they're different shades?" I was figuring it out as I talked. "And I know I said I like the fitted jeans in the last one, but these pants look nice. The shirt and sweater too, although maybe they'd be too loose. And I guess I should say, I don't know where I'd ever wear this stuff. But it looks dressy. Dressy but comfortable."

"Really useful feedback," said Charlie. Charlie brought up an image of a cadaverous model wearing a layered outfit clearly based on traditional Japanese clothing. A jacket like a kimono over a thigh-length collarless button-down v-necked shirt, all worn over a white tee that might have been made of silk. The pants looked wide-legged, but it was hard to tell from the image.

"He could use a burger," I said. "And a milkshake."

"Focus!" snickered Charlie, nudging me with his shoulder. "What about the clothing?"

"I like the look. I dress in layers when it's cold. But more than that, it looks comfortable but also flattering. It seems formal for such a casual look? I'm going to stop saying `costumey' but together, the look is too much."

"Do you see how all the tops elongate the model? All the lines draw your eyes up and down. Plus the fabrics are very high-end. Even if you don't know that's what you're looking at, your brain takes that sort of thing in. Is that what you meant by formal?"

I looked more carefully at the picture. "It all looks good together. The layers go together, the colors compliment each other but aren't matchy like the last one. I wouldn't wear baggy pants like that, though."

"Too much fabric?"

"Annoying," I nodded. "Plus, I don't want it to look like I'm playing dress-up. I feel like all these super oversized pants just scream, `I'm trying so hard.'"

"Interesting," said Charlie. "What's wrong with trying? Or trying hard?"

"Vanity," I said after thinking for a minute. "I guess I think about fashion as superficial, material. So the more obvious it is that I'm trying too hard, the more it looks like I've got my priorities wrong."

"That's good for me to know," said Charlie. "I'll push you, though. Not because I want to change your mind, but I don't want you to write off clothes or styles too soon. Think about wearing that shirt and sweater on a lazy Sunday morning in your dining hall, eating bagels, avoiding a paper due on Monday."

"It seems like a lot for bagels in the dining hall, but I see what you mean."

"Not in that gray, though. It would wash you out. Maybe in dusty blue?"

Oh god, I thought. More rules I didn't know.

"How about this?" Charlie asked, skipping over a few outlandish pictures before stopping on a photo of a striking man in a patterned gray suit, lavender dress shirt open at the neck, and a burgundy silk handkerchief in the breast pocket.

"I could never pull that off," I said. "He looks good, but talk about me playing dress-up."

"You could make it work," Charlie said seriously. "Maybe it's a little much put together like this, but the colors would all look great with your complexion. Get rid of the plaid on the suit, go with a simple charcoal or navy, and you would absolutely rock this look if you were going to a reception or play, maybe a concert."

"I'm stuck on the handkerchief."

"Pocket square," corrected Charlie gently. "It dresses-up the outfit, makes it a little more formal, lets you get away without wearing a tie if the occasion doesn't absolutely require it."

I groaned. "So many rules," I said. "I'll break them without even knowing they exist."

Charlie nodded. "This one is probably Advanced Placement when it comes to fashion. For every day, just do what your classmates do and you'll be fine most of the time. I'm showing you this extra credit stuff to see how far I could push." I groaned again.

"I don't even know where to begin with all this stuff," I said. I wasn't exactly frustrated, but I was so far outside my comfort zone I wondered if I had any chance of pulling off any new wardrobe without seeming totally phony.

"Do you trust me?" asked Charlie.

I did.

After about an hour of looking through photos, Charlie said he'd learned enough. "I have a pretty good idea of your comfort zone, and what you might consider, and some ideas to push you too."

I reached under the blanket and gave his thigh a squeeze. "Do you want to take a break and let me push you?"

Charlie scoffed through his nose. "Focus, you horndog! We still have lots of work to do."

"Just a little break?" I wheedled, running my hand from the top of his thigh inside and up towards his balls.

"Focus!" he said, but Charlie was close to laughing. "We're making real progress." He shook my hand off his thigh. "Have you ever heard of a company called `Eclat Quantum?'"

I hadn't, I told Charlie. "But I don't really follow fashion."

"That's why we're here," Charlie said, bumping me with his shoulder again. "Okay, so EQ was founded by one of the RAs from my freshman dorms. Troy's a technology whiz. Hardware, software, programming. Guys he met in business school found a way to use his tech in the fashion industry."

He was excited talking about EQ. "Troy's their Chief Technology Officer but he's also really involved in finding their right niche and scaling as they come to market. CTO and COO combined."

I wasn't entirely sure what any of that meant, but it sounded like the company is new and growing.

Charlie said he started helping Troy because, ironically, none of the founders had much experience in the fashion industry. "I gave Troy some suggestions for styles, fabrics, trends, that sort of thing. I'd done a project on fabric supply chains that he found really helpful. In return, he sends me clothing. I have an appointment to visit his showroom tomorrow. Troy wanted me to invite you too."

While he was talking, Charlie opened up a new program on his laptop and started to build a profile based on my height and some measurements he'd taken using his phone and a piece of twine. "They can fine-tune this tomorrow," he said to himself. When he was done, the screen showed a three-dimensional body shape that looked a lot like mine.

"Now that you've got a profile, let's make fashion!" he said with a flourish. "First shorts, since that's what you live in and there are fewer options. It'll be a good place to start." With a few more clicks, a pair of very short khaki shorts appeared on the model. Tan chino shorts, I thought.

"No way," I said. "Maybe for a bathing suit, but not around campus."

Charlie nodded like he expected my reaction. "That's a five-inch inseam. All the slutty boys in New York wear them."

"I don't want to look like a slutty boy."

Charlie reached down and squeezed my inner thigh. "Even if you are a slutty boy, Horndog?"

Before I could answer, he began typing and clicking. What a tease.

"What do you think about six and seven inches?" He pulled up side-by-side images of the same shorts with longer inseams, one less revealing than the slutty shorts and the other downright modest in comparison.

"Six or seven inches?" I used my most earnest voice. "It's not the size of the boat but the motion of the ocean, Charlie. What matters is it's who it's attached to. Thick is nice, though."

Charlie groaned and batted away my arm as I tried to grab his thigh again. "Focus!"

I gave up trying to distract Charlie. He was trying to help and what he was doing was important to him.

"I think six is the right length for me," I said. "But I'd want to try anything on before I bought it. This looks pretty expensive.

"Don't worry," Charlie said. "You'll be able to try on everything tomorrow. We're just doing homework right now. And it is high quality, but it's way less expensive than it looks."

After shorts, Charlie pulled up pant styles, each with a drop-down menu for cut, color, and fabric choices. He created a folder to save what I liked, which included clothes he thought I should like even if I wasn't sure.

After pants, we built out the order for shirts, jackets--"outerwear" according to Charlie--and even a couple of suits. It was nearly dark when Charlie submitted the folder to store's website.

"We have an appointment at their showroom at 10:00 tomorrow morning," Charlie announced. "It's in downtown Philly, but it'll be worth the drive.

That was probably three hours in each direction, in the rain, in city traffic. And it would be on a Friday, so traffic back to the beach would be especially terrible. None of that sounded fun.

"Is this really worth it?" I asked. I'd found an outlet mall less than an hour away, and it even advertised as "premium." I was sure I could find whatever I needed there. Couldn't I?

"EQ will totally be worth the hassle," said Charlie. "They'll have everything ready for us to try on, in the measurements we submitted. It's all mocked-up from basic fabric, just muslin or something else inexpensive, to make sure the fit is what you want. They have a green screen to show how it will look in different colors and fabrics, plus swatches so you can feel everything before you place the final order."

"Hold on," I said, my adrenaline spiking. "Handmade clothes? Or personalized? There's no way I can afford this."

Charlie smiled. "It's not handmade. Other than tweaking the fittings tomorrow, it's all robotic and mostly based on existing templates. That's the EQ innovation. They use machine learning, artificial intelligence, neural networks, programmable supply chain equipment, all sorts of cutting-edge technology. Once you finalize the order, it only takes about 48 hours to make it."

"You're not making it sound any less expensive, just too good to be true."

"The clothes I have from them are great. One the basic side, but they were early products, prototypes almost. But I've been waiting to visit their showroom for a long time. Troy's promised me a real experience. I mentioned you when I was setting up my appointment and he said you had to come too."

I breathed a sigh of relief. It took off some pressure to know that Charlie was shopping too.

"So we show up, try everything on, and they'll magically make a whole new wardrobe in a couple of days? An affordable wardrobe? They should call themselves `Rumpelstiltskin.'"

Charlie laughed. "It's even better than that, based on what Troy's been saying. Tomorrow we'll see their `Atelier' model. They'll have a Consultant who can suggest fabrics, different styles, things they think will look good if we didn't already consider them."

I shook my head. I trusted Charlie but the idea of a personal shopper on top of everything else seemed impossible.

"They're trying to figure out the business model," Charlie said. "Troy said they negotiated enough funding to buy equipment and materials to test the concept. They got a ton of interest so they have some room to try to execute. He thinks they're just about to break through."

The more Charlie talked about the company, the more enthusiastic he got. He wasn't exactly lecturing, but I felt like he had switched into pitch mode. It was fun to see his excitement, even if I didn't understand all his business-speak.

"When they were starting production last Spring, they had some quality issues. Seams and cut mostly, but also some of the customization wasn't right. Troy said they've fixed everything. Now, they're somewhere between proof of concept and beta, trying to find the right quality levels and price points. We'll see more tomorrow, but Troy told me he'll show us their high-end product."

"Oh boy," I said with a weak laugh. "That sounds even more expensive."

"Stop worrying," said Charlie confidently. "Troy told me he'd give me the `friends and family' discount."

"If you say so," I said. "You're sure I don't have to pay for anything if I don't like it?" The list we'd submitted had more than three dozen pieces of clothing, many in more than one color or fabric choice.

"And I even paid the materials charge for the mock-ups," said Charlie, somewhere between proud and smug. " It's my parents' present to you for letting me sleep `on your couch.'" He laughed at the air quotes.

"I ain't no whore," I said in my best Julia Roberts voice. Charlie didn't get the reference so maybe his grandmother didn't love "Pretty Woman" as much as mine. "I don't want you to pay for staying with me. I've had too much fun."

"You want fun, Horndog?" Charlie said. "I'll show you a real good time." He closed his laptop, whipped off his shirt, and proceeded to do just that.


AUTHOR'S NOTES:

Thank you as always for your comments and critiques. I'll publish the next chapter--an unplanned Charlie C--which was originally part of this chapter before it took on a life of its own. I'll have Charlie C out by early next month. Next will be the final chapter of Jon's Roadtrip, which will be short, transitional, and sexy. And then deeper introductions to Jon's suitemates.

In the meantime, thanks to all of you for your thoughtful comments. Please let me know what you think!

cottagecore.stories@gmail.com

Also, if you can, please donate to Nifty at https://donate.nifty.org/


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