Episode 1 – Off to the City

I’m fifteen, but don’t look it. I’m cursed with a baby face…blond hair, blue eyes, peaches and cream complexion. You get the picture, right? Mom still pinches my baby cheeks, tells everyone I’m “cute as a button” and taunts me to smile so she can show off my perfect teeth (braces just removed) and embarrassing dimples. Lately, I use any fucking excuse to stay away from home.

It’s Summer vacation, but September to May, I attend The Chandler-Dilworth School in Putnam County. Since school ended, I’ve been stuck in my dinky home town, Findlay, NY, which is dead as a fucking doornail. I’ve totally grown out of hanging at the local hot spots…the Wooden Nickel deli, Wally’s CD’s, and our shitty mall which is on the verge of bankruptcy…half empty stores, no national chains…just a liquor store, home furnishing store, pharmacy and a couple of women’s boutiques. The food court’s a fucking joke. Only two counters are open, Betsy’s Burgers, and Buddy Chen’s, both sub-marginal. I avoid them like the plague. A bunch of kids have gotten food poisoning because of the unsanitary conditions, namely r-a-t shit. I oughta know because Dad’s an internist and Mom’s his nurse.

At school, my best friend and roommate is Ryan Hughes, but he lives down in the city, so I don’t get to see him all Summer. It pisses us off big time, so this year, we’ve plotted to do lotsa shit during vacation. His family always goes to East Bumfuck, Maine, but this year Ryan’s convinced them to let him stay home with his 19-year-old older sister, Nina, who’s also blowing off the family trip. She got a job at Baskin and Robbins so she can shack up with her boyfriend.

Ryan gave his parents a bullshit story that he’s been bitten by an Astronomy bug, and decided to take a Summer course at NYU…has as much interest in Astronomy as I do in herpes…probably less…but his parents got sucked in, probably wishful thinking because Ryan’s a basketball stud, but not much of a student. As part of the deal, he told his folks I’d come down and keep him company which, amazingly, reassured them. Guess they figured anyone with my baby face and clean reputation, wouldn’t lead their son to debauchery and ruin…Lol.

On the flip side, my parents are upstaters…can’t imagine their little guy in the Big Apple. Perish the thought! They think I’m ten instead of fifteen, which is a major pain.

Fortunately, Nina’s pretty crazy, and agreed to help us by imitating her mom over the phone…totally convinced my parents I’d be welcome and well supervised, and they bought it hook, line and sinker (one of our quaint upstate expressions).

So, here I am on Metro-North heading to Sin City. It’s a muggy, July day, and I’m in my Bosox shirt and hat, cargoes and high tops. Kids consider me a traitor because I’m a Boston fan, but Dad’s from Worcester, Mass, so I have a legitimate Sox pedigree.

For the first forty-five minutes, the ride’s pretty quiet, but when we hit Brewster, people pile on…including a bunch of screaming girls heading to the city (at least I hope so!).

As usual, I get lots of curious glances. It used to piss me off so much, Mom would try to explain it away. “Caleb, it’s a complement, not an insult. Your darling face attracts attention,” but I still felt like shit. In public…like on the train, it’s embarrassing…sometimes attracts the wrong attention, like the weird forty-something guy across the aisle who can’t keep his eyes off me. Pretends to be talking on his cell..but then there’s a click and a flash, and I’m royally pissed. Glare at the fucker, and he’s all embarrassed: “Sorry, son, I’m still trying to figure out this cell…keep pushing the wrong button.” Total bullshit. He’s such a fucking pain, I look for another seat.

By the door, there are facing bench-seats filled with girls…one place empty. “Is this taken?” I ask.

They give me a quick look. “Sure, no problem.”

I settle in. Try to act casual…pretend not to notice they’re checking me out from head to toe. Of the five, three are sizzling and two are nothing special…just don’t have the fashion sense, or bodies, of the hotties. One’s heavy and the other’s anorexic and hyper.

Unfortunately, the chubb can’t keep her eyes off me. Finally asks if I’m headed into the city.

I nod, smile. “Yup, I am.” No reason to be a snob. I like pleasing people….goes back as long as I can remember. When people stare, I automatically smile….always does the trick….like I’m fulfilling their dreams or something.

“Any place special?” She asks.

“Upper West Side…visiting a school friend. How about you?”

“Just shopping,” then she fucking grills me about where I go to school, if I play sports…what music I like? Yada, yada. I tell her about Chandler-Dilworth. How I’m addicted to sports…go out for soccer, wrestling and baseball. She’s surprised I’m in the same class they are.

“What’s your name?” She asks.

“Caleb Dawson.”

Her eyes brighten. “What a cool name…Caleb’s, like, Biblical, right?”

I chuckle. “Yup,” ask her name in return.

“Kathleen Coletti, but my friends call me Kat.”

Kat’s a type of girl I’m familiar with…jolly, outgoing, might be pretty if she lost a few pounds, but as it is, her features are kind of lost…except her big brown eyes, which are amazing.

After a while, our conversation trails off, but right away, one of the hot girls, picks up the slack. “Did you say you were visiting a friend on the Upper West Side? How far up?”

“Not too far. 73rd right off Central Park West.”

“That’s a cool area. We’re heading to the East Side.”

“It’s great there too,” I say, not that I know the city very well. “What are you planning?”

“Hang for the day…shop. We’re gonna hit Bloomies, Saks, maybe Ralph Lauren.” She gives me a warm smile….sort of a baby face like mine…big green eyes, perky upturned nose, and endless blond hair…can’t help staring. The more I look, the more I’m becoming obsessed!!!

“You two could be brother and sister,” Kat says.

I laugh. “Yeah, right!” But she has a point. There are similarities, especially coloring-wise, but my face would look a helluva lot better on a long, slim body, instead of a pint-sized one.

The girl studies me without saying a word.

Figure I better dive in. “Name’s Caleb,” I tell her. “What’s yours?”


I nod, then we don’t speak a while. I pretend to fall asleep as the train rumbles along…actually get a little drowsy. Cross my hands in my lap as a precaution. Willa’s showing some awesome cleavage…a pale crease between white downy orbs. I’m in heaven! Kat catches me staring…smiles slyly. Get the definite impression she has a crush on Willa…maybe my interest turns her on. Who the fuck knows?

The thin, nervous girl pretends not to notice a thing, just stares out the window at the world whizzing by. The two other hotties are deep in discussion about…no big surprise…boys:

“I can’t believe he said that to you. What an asshole!”

“It’s weird. He’s such a strange guy.”

“I thought he was going to ask you out.”

“Me too, but he doesn’t seem interested. I don’t get it.”

“God, he’s so gorgeous. Is he gay? Have you heard any rumors?”

“Not really, but he’s having a bromance with Tommy Mulder. They hang together 24/7.”

“Lacrosse studs. Doesn’t he date at all?”

“Occasionally, but nothing serious.”

“Is he a virgin?”

“It’s possible, but s-o-o-o hard to believe nobody’s gotten in his pants.”

I start dozing for real. The train’s hot…makes me really groggy. The girls change subjects…start whispering about me.

“What’s his story? He can’t be fifteen.”

“No way. He looks, like…thirteen max.”

One of them whispers to Willa. “How old do you think he is?”


“I don’t think so. He’s cute and all, but think about it. Does anybody in our class look like that?”

“That doesn’t mean anything.”

“You’re delusional.”

“Why would he lie?”

“To impress us. Think about it. He’s a horny underclassman. They’re all alike.”

I doze off…wake up as we’re entering the Grand Central tunnel.

The girls are still chattering, except Willa who’s watching me. I stretch and yawn. “Wow, I’m so sleepy!”

She smiles. “It’s hot. I don’t think the air-conditioning’s working.”

“Hey, guys,” Kat asks. “Where we going first?”

“H&M and Urban,” one of the hotties says. “God, I love Urban!”

After a while, the darkness ends, and we stop beside the lighted platform.

Willa turns to me as she’s gathering her stuff. “How long are you in town?”

“Probably three weeks.”

“Wow! I wish I could stay in the city three weeks. It’s s-o-o-o awesome! You’re staying with your friend’s family?”

“Sort of, just him and his sister.”

“Can I have your number? Maybe we can plan something?”

“Sure.” The other girls watch in stunned silence. I’m psyched.

One of the hotties chimes in: “You’re not really fifteen are you?”

“Yes,” I tell her, “I really am.” Does she think I’d lie???

Willa gives her a dirty look. The others roll their eyes…like, whatever.

I get down my bag and we file onto the platform. Can’t get over how dirty and drab it looks…guess nobody gives a shit. Grand Central’s too big and bustling to stay spruced up…especially in the tunnels. We say goodbyes. Willa glances back and our eyes meet…just a split second, but so obvious we’re interested.

I grab a cab and head to Ryan’s on West 73rd Street. Feel good. Picture Willa’s beautiful face. She’s definitely the hottest girl I ever saw…by miles! Just thinking about her makes my cargoes rise. After a crazy ride, we pull up in front of a fancy building…doorman out front. Quickly make adjustments and step out.

“May I help you?” He asks. Looks me up and down, like he’s wondering what I’m selling.

“Hi, uh…I’m here to visit R-y-a-n Hughes.”

“Your name is?”

“Dawson…Caleb Dawson.”

“Just a minute.” He dials the number. “Mr. Hughes, Mr. Dawson is here to see you.” Obviously, Ryan gives him the okay, so the tension evaporates. He directs me to the elevator which whisks me to the tenth floor. When the doors open, I’m in the apartment, which is immense, and Ryan’s waiting.

“How was your trip?” He asks…slapping me on the back. “Great to see you, dude!”

“Super! it was easy. I got a cab right away, but holy shit. I met the hottest girl on the train!”

“Did you get her name?”

“Not exactly. Her first name was Willa, and oh man, was she awesome…asked for my cell number.”

“Did you get hers?”

“No. We were getting off and it was crowded.” Think to myself: you dumbass…can’t you do anything right? Cool guys always know what to do, but me? One fuck-up after another!”

Ryan grabs my shoulder. “Dude, read my lips. Anytime you meet a hot girl, get her number! You can call just as well as she can.”

I shake my head. “Yeah, I know, but I didn’t want to seem too desperate.”

“Dude, if she asked for your cell, it’s a go signal.” He looks me in the eyes. “Got it?”

“Yeah, of course,” I reply, totally intimidated. Ryan’s a tall, lanky guy…handsome. Looks ten years older than me. Oozes confidence…unlike me, who oozes inexperience. The fact that we’re best friends constantly amazes me.

“Dude,” he says, “I don’t know whether it’s because you’re short or what, but stop thinking you’re twelve years old. No girl will mind you asking her out. I know you…because you look young, you think girls’ll be insulted, but Christ, dude, look at yourself in the mirror. You’re a blond wrestling stud. That adds up.”


“No maybes. Come in and get comfortable. Wanna beer?”

“Yeah, that’s what I need. I’m pretty fried.” My cell buzzes. “Shit, who can that be? Hello?”

“Caleb?” A girl’s voice.


“Yes, from the train. I enjoyed meeting you…maybe we can do something next week?”

Her image shimmers in my head. I’m totally hooked, and “next week” sounds like a year. “How about Sunday?” I ask. “Is that too soon?”

“Wow, Sunday. Like the day after tomorrow? Yeah, I could do Sunday. Where shall we meet?”

I’m like jumping out of my skin. “How about Grand Central, at the clock, around eleven? We can hang on the Upper West Side. There’s the park, and the Museum of Natural History which is really cool.”

“Okay, Caleb,” she says enthusiastically. “That sounds perfect! What are you doing today?”

“I’m not sure. My friend Ryan’s my social planner.”

“Okay. See you Sunday. I’m so glad we met!”

“Definitely. look forward to seeing you!”

After the call, I’m in shock. Close my eyes and raise my fists in the air. “Fuck yeah! I can’t believe she called!”

Ryan hands me a beer. “Take it easy, dude. Girls don’t like hyper guys. Chill…enjoy your brew.”

“But, Ryan, you should see her! She’s spectacular, and oh my god, her body is so fucking awesome! I almost lost it just looking at her.”

“Well, I hate to tell you this, but I asked Nicole to set you up, so she’s bringing a date over.”

“Are you serious?”

“Yeah, her name’s Gigi and she’s a total nympho.”

I take a deep breath. “A nympho?” Try to keep cool, but I’m in total shock. How the fuck am I going to handle an experienced girl who’s expecting to fuck all afternoon…and how can I blatantly do shit with her when I’ve met the girl of my dreams??? Ryan’s ultra psyched…tells me he and Nicole have already hooked up multiple times…he even gets blow jobs and shit, but I haven’t done squat. What a fucking mess! I chug my beer and get another.”

To be continued… Read next episode!