The Virgin Artist Ch. 01


Note: All characters engaging in sexual activities are 18 years or older.


Winston Thomas, a lanky artist with lanky hair and lanky eyes and lanky everything, lean and sharp as a blade of grass, leans against the railing of the cruise-ship Allure and stares out at the ocean, trying his best to sketch the distant waves and not worry about being a member of that most ignominious of combinations: a college freshman and a virgin.

It almost works. Drawing water is no mean feat. It never stands still — it’s even more poorly behaved than small children and only slightly more favorable in comparison to wind because you can’t really draw wind, you can only draw windy things. Like trees and waves and hair. A girl’s hair, long and beautiful, caught in the jealous fingers of the wind. And with that fatal thought, Winston’s back to worrying about being a virgin.

It always comes back to that. Girls have a sixth-sense about it. They can just tell. They just know and that’s that. They like an experienced guy, an older guy. Now, Tiffany Rosens, she of blonde hair and blue eyes… he had a chance with her. That is, she mostly ignored him but a couple weeks back, she’d told him she really loved his artwork. The look she’d given him… Smoldering is the only word Winston can think to describe it. He understands looks. He has an eye for them, an artist’s eye. Yeah, Tiffany Rosens — he had a chance. Key word: had. But, instead of making business with her, his parents had forced him to go on this trip, a graduation gift that they just so happened to have invited themselves upon.

Cause, really, a Caribbean cruise? How trite.

Winston pauses, erases one of the white-caps of a distant swell, and amends his thought: the cruise is alright. There are some parts he doesn’t mind. He likes people watching, the range of people from fat to skinny, swarthy to pale, smooth to wrinkled, red-heads, gold-heads, raven-heads. He likes the gentle almost imperceptible rocking of the ship in its ocean cradle, the inescapability of the sun and the infinite expansion of the sea. And, of course, he likes the girls in their bikinis, all curves and slopes and—


Startled, Winston looks around, nearly has a heart-attack when he almost drops his sketch-pad into the ocean, and then watches with some annoyance as a young girl, no more than eight or nine, bodily drags one of the lounge chairs up to the railing and proceeds to stand on it to look out over the edge.

“Oooh!” she says followed shortly by the requisite “Ah.”

Oooh, she says again, and … ah! Ooooh… ah! Like the vocal beat of a techno song. It irks Winston. Unfairly, of course, definitely unfairly. The girl’s still innocent, still able to appreciate the primal beauty in things. Winston had been like that once. And then he’d hit puberty. With a sigh, Winston turns back to his sketch pad — but then, from the corner of his eye — he sees the girl tilt too far, overbalance, and fall.

Winston reacts instantly. His arm shoots out and snaps hold of the girl’s wrist. Small though she is, her weight jerks his arm, and he nearly lets go. But he doesn’t.

Winston’s not exactly a football jock, and the girl’s wrist, slick from the ocean air, begins to slip from his hold. “Help!” he shouts.

Two nearby sailors hear his cry and rush over. They grab the girl by her other arm, her clothing, and haul her up. In moments, she’s back over and safe. Her mother, a pretty but mousy lady, rushes over and grabs her daughter and begins to cry. The little girl, not quite realizing her peril until now, bursts into tears as well.

One of the sailors turns to Winston. “Wow, kid. What the hell happened?”

“Dunno,” says Winston. “She slipped.”

“And you caught her?” The sailor offers his hand, which Winston awkwardly shakes. “Timothy Owens. Pleased to meetcha, and how’d you manage it anyway? What are you, some kind of martial artist?”

“Winston Thomas,” says Winston. “No — just an artist.” And saying it, Winston realizes that in his haste he dropped his sketch-pad.

“Quick of the eye then huh?”

But Winston, not finding his sketchpad, has already exited the conversation. He leans slightly over the edge and spots his expensive moleskine, caught on a balcony several floors below. “My—” but the wind grabs it and carries it off into the sea. “Shit,” says Winston.

Meanwhile, the girl’s mom displays a rapid switch of emotions that would have sent any nearby psychologists screaming for some lithium. She gets angry and scolds her daughter Madeline and shakes a finger at her and cries, and then turns to Winston with a melon-eater’s grin and offers effusive praise, giving him a fierce hug that crushes his lanky frame. He can’t help but notice her large breasts, rare as they are on a woman — as Winston now notices — of oriental descent. Or, at least, half oriental, by the slanting of her face, the dusky tone of her skin.

Drawn by the commotion, a crowd begins to gather and Winston slips away. He prefers the cool silence, the distance, and always had. It’s easier to observe, easier to capture motion, when you aren’t a part of it. And anyway, he needed time to mourn the loss of adana escort his work.

But the story spreads — thanks in no small part to Timothy Owens, who runs the cruise ship’s little commodities shop (toilet paper, toothpaste, & t-shirts) — and eventually Winston is recognized the ship over. Men stop him and shake his hand, and women say things like, “Bless his heart” as he walks by. Frankly, it’s annoying. He’s even drawn aside by the celebrity attendee, the famous Hollywood actor Borden Saint, for a quick publicity shot in the cruise-ship’s ‘Gardens of Allure’ a little indoor pseudo garden filled with gurgling fountains and bright flowers kept in a state of perpetual bloom through a healthy amount of sun and an unhealthy amount of chemical motivation. For some stupid reason, Borden gives him a little garland of flowers, which Winston tosses over the side, as easily abandoned as Borden’s fake smile, once the photo shoot is over.

Three days after saving the girl, three days after being greeted by complete strangers and people pointing him out as he’s trying to relax by the pool or get a sandwich to eat, Winston finds himself sitting at the La Parisian outdoor café, drinking tea, and sketching on a small legal pad when his latest ‘fan’ sits down.

“Hi,” she says.

“Hello,” he says, without looking up. He’s drawing a caricature of Borden, having great fun with giving him a chimera look: the tail of a scorpion, the wings of a bat, the snout of a hyena.

“Are you Winston?”

He sighs inwardly, but then he looks up. His fan’s a girl — his age, for once — and actually, well, actually kind of cute. She has a lively face, full of emotion and mystery. A small nose — she’s maybe a quarter Asian, three quarters Caucasian — and just a hint of slant to her eyes, and olive skin. A bridge of freckles across her nose. A real weakness for him. He likes freckles. Long, almost unkempt dark hair, thick and silky, and a pencil stuck behind one ear. She seems both eager, yet cautious, and Winston doesn’t quite know how to interpret her look.

“Yes,” says Winston. “That’s me.”

“Hi, I’m Luna. That was my sister you saved. I want to pay you back.”

“Oh. Uh, thanks. I mean, that isn’t necessary. Borden Saint gave me a hat of flowers and shook my hand. Everything a boy can ask for.”

“That’s nice,” says Luna. “So how can I pay you back?”

“Really,” says Winston. It’s okay, it was –“

“I’ll take you to dinner. Meet here at 6? Okay? Okay. See you then.”

“Uh, okay,” replies Winston but she is already gone.


Winston dons his best pair of jeans, a white under-shirt, a long-sleeved t-shirt with sleeves rolled up, and tries his very best not to project the aura of a virgin. Luna arrives at exactly 3 minutes to six, dressed in a green summer dress, light and airy. She hooks her arm into his and steers him down the cruise’s ‘board-walk’ and into a Japanese-themed restaurant with a red triangular arch and red columns, etched with golden dragons.

“Hello,” says Luna to the hostess. “Reservation for two under Luna.”

“Right this way,” says the hostess, dressed in a kimono that whispers as she walks.

She leads them to a secluded table in the back, bordered on one side with a screen depicting the earth on the back of a turtle and another side by a bamboo wall. Winston rushes to pull out the chair for Luna, which she happily takes, smoothing her dress before sitting down.

“Thank you,” she says.

“Your server will be right with you,” says the hostess. She hands them two menus before leaving them to their privacy.

Luna takes her menu, scans it rapidly, and sets it down, before Winston has even made past the appetizers — crab wontons and calamari.

“You already know what you want?” asks Winston.

“Yes. I looked up the menu before-hand. Don’t want to get it wrong.”

“Right,” says Winston. “That makes sense.”

“I know. So, Winston,” she says, folding her hands on the table. “Tell me about yourself. How old are you? Are you still in high school? What do you do when not rescuing small girls from plummeting into the ocean? Do you always dress so casually? What is your favorite animal?”

Winston places the menu aside, notices that, like her mother, Luna has large breasts, and does his best not to look rudely at them while talking to her. “I’m 18 and no — I’m entering college this next year. My –“

“What college? I have a scholarship to Cornell.”

“Really? Me too. I mean, I’m going there too.”

A smile lights up Luna’s large, dark eyes. “What? No way. What major? I’m comp sci.” Winston’s mesmerized by her face and starts to zone her out. “Maybe mechanical engineering too. They have an incredible robotics program there.” She has the perfect face for drawing. Crayons would be just perfect for it. “Are you going into engineering too? Are we going to be classmates?” Yes, crayons. A broad children’s caricature almost, to capture the energy, the liveliness. “You’re not a liberal arts major, are you? You’re not a…” she lowers her voice “… an artist?”

Or maybe some combination of water-color and — “Huh what? Er, well, yes, I am an artist.”

“Oh…” says Luna. “I like art. Do you paint?”

“Well… I haven’t found my style yet. I’m just, um, experimenting. I like drawing. In fact, I was doing some sketching when your sister almost fell. Lost my sketchpad — into the ocean. It’s probably been swallowed by a whale by now…” Misinterpreting her downcast look, Winston hastily adds, “Not that I mind losing it! Well, I mean, I do — but in exchange for your sister, it’s no problem. It’s no good. I mean, it is good that she’s okay.”

“Yeah,” Luna says. “Maddy won’t shut up about ‘her hero.’ This was her idea, actually. She told me I had to um…” she blushes and changes topics. “I’m sorry about your sketchpad. Maybe an underwater kingdom will find it and enshrine it their museum of lost artifacts?”

“Maybe,” says Winston.

“Do you know what you want yet?”

“No. You were asking me questions and –“

She tsks. “Better hurry. Our waiter is on his way.”

Luna, who it turns out had spent two years in Japan with her Japanese grandmother, orders Tako, Ika, and Tamago sashimi and what’s called the “Allure roll” while Winston settles for a simple Teriyaki Steak meal.

“Can I ask you something?” asks Winston after their waiter leaves.

“Yes. Of course. Ask me anything. You’re my sister’s hero, after all.”

“Do you have a boyfriend?”

She pauses to pour herself some hot tea. “Why d’ya wanna know?”

“Just curious. You don’t have to answer if it’s a problem.”

She sips her tea, staring at him over the rim of her tea cup. “Well, no as a matter of fact. Between the APs and the tennis team and piano recitals and volunteering at the library and working at my uncle’s software company, I haven’t had time. Do you?”

“No,” says Winston and adds, “I’m straight.”

Luna stares at him uncomprehending then rolls her eyes. “You know what I mean.”

“Uh, well. No. I’ve also been busy,” he says.

“Have you ever had a girlfriend?” she asks.

“Well, in sixth grade –“

“So you don’t know anything about sex?”

Winston hides his embarrassment by drinking water. He may not have had a girlfriend since sixth grade, but he’d listened to his buddies. He’d watched porn. These days, who didn’t know about sex? “I know plenty—”

“That’s okay,” she says. “Since you’re single and I’m single, we should be boyfriend and girlfriend on the cruise. We can learn — before we get to college.”

“Boyfriend and girlfriend?” he says. “Learn what?”

“Sex, obviously,” she says, looking directly at him. “Sex things.”

He looks away, folding and unfolding his straw wrapper. “Like…” kissing?”

“Sure. And other stuff.”

“What other stuff?”

She gives him a flat look. “You know, sex stuff.” She pauses then adds, “Handjobs, blow jobs. Sex stuff.” Winston avoids the temptation to pinch himself; if this is a dream, he doesn’t want to wake up from it. Instead, he drinks some more water.

“I’m still a virgin, are you?” asks Luna.

“Yes,” Winston admits.

“Okay, then you have no choice but to say yes.” She waits. “So say yes.”


“Okay, good. I predicted you would say yes, but…” she reaches into her large purse and pulls out a notepad emblazoned with an orange crescent moon. “I have three rules: First. You have to do whatever I do. I believe in equality. Second. My parents must not find out. They would absolutely freak. If a boy even looks at me, I get grounded. If they were to see me with one…”


“Decapitation. Third, don’t think this means we’re boyfriend and girlfriend elsewhere. This is special and it’s on a trial basis. We’re here to learn.”

“Okay,” says Winston. “So no fucking around.”

Luna rolls her eyes for the second time that night, but then adds “We’ll see.”


The next day, the ship pulls into the port of San Juan, Puerto Rico, and Winston’s parents disembark after failing to convince Winston to join them. At the pre-scheduled time of 10:30 am, Luna knocks on his door. Winston lets her in, checks to make sure the corridor is clear, realizes he doesn’t even know what he’s looking for, and shuts the door.

“Hi,” he says.

“Hello,” says Luna. If Winston had thought her purse last night was large, then the one she carries now is huge. Less purse, more toolbox. Perfect size for a wallet, a drill, and a car battery. She sets it to the side as she pulls up a chair and sits down. Winston takes a seat opposite her, on the couch.

“So…” she says.


“Winston, we’re boyfriend, girlfriend, right? You’re serious about this? Because I am.”

“Yeah, sure.”



“I want to see your cock.”

Winston manages the impressive feat of choking on air. “What?”

“I want to see your cock. Or should I say something else? I read that some people like to use euphemisms for their parts. To make them comfortable. Seems silly to me. Would you like me to call it Mr. Johnson?”

“Uh, no,” says Winston shifting uncomfortably. As soon as she walked in the door, even dressed conservatively in a pair of sweat pants and a loose-fitting shirt, he had started to grow hard. Now his ‘Mr. Johnson’ is fully erect, and visibly so. “Cock is fine.”

“Okay,” she says primly. “I want to see your cock. Take off your pants.”

Winston stands up and fumbles with the button and zipper of his jeans, suddenly the most complex contraption known to man. After an excruciating fifteen seconds, he manages to unstick the zipper. He pulls his jeans off, revealing boxers tented by his hardness. Still shy, Winston glances at Luna and notices her staring at him intently. He hooks his thumbs into his boxers and pulls them down; his cock springs free.

Luna purses her lips and nods. “Do you know how long you are?”

“Er, no? Average, I guess.”

“I mean, actual length. Do you mind if I measure?”

“I guess not?”

Luna reaches into her huge purse and pulls out a 12-inch ruler.

Winston cracks a smile. “You brought a ruler?”

“What do you mean?” says Luna. “I always have my ruler with me. Lean back now.” She measures him, taking great care to avoid touching him any more than necessary. “Almost seven inches,” she says. “Six and nine-sixteenths. That’s bigger than average.” She opens her moon notebook, retrieves the pencil from behind her ear, and makes a quick note. “I’ll take off my pants now.”

She manages her own sweatpants with relative ease, revealing simple green underwear, very shiny. Winston wants to ask to be the one to take them off, but before he can work up the courage, she lifts up her hips and rolls them off. He sees his first pussy, in the flesh anyway. It’s beautiful. Not that he has anything to compare it with, but that animal part of his brain — the ancestral part — that long genetic lineage that has baked from womb to womb to womb for the last thousand years — it knows. He feels for the first time that insatiable hunger, those pangs of a lust that can only be satisfied by burying himself in a woman. But he doesn’t really understand all that yet. He just knows he wants her and that she is beautiful.

She lets him look, a blush growing steadily in her cheeks, before she crosses her legs. She looks annoyed, but most of all, annoyed at being annoyed. “So?”

“I like it,” says Winston.

“I meant, now what?”

“Can I see your breasts?”

She shakes her head. “No.”


“Hm,” says Luna. “I think… Can I touch it — your cock, I mean?”

Yes! Winston almost blurts out, but instead says, “If you show me your breasts.”

Luna gives him a scandalized look, then tilts her head in a curious manner reminiscent of a bird hearing the distant song of a potential mate, and after a second of thinking, offers her hand. Winston shakes it. “Deal,” she says.

She takes off her shirt to reveal breasts that are just as pretty as her lower parts. They’re much larger than he would have thought, and he’s particularly drawn to that sloping valley between the two teardrop-shaped mounds. He wants to kiss her right there. After she takes off her bra, also green and shiny like her panties, he gets a brief glimpse of nipples — incredibly long and lightly brown – before she covers them with an arm. He decides that she has the most fantastic coloring, and he doesn’t know whether he wants to have sex with her or draw her.

Instead, however, she scoots up and sits next to him on the couch, close enough that her thigh touches his, a touch that sends a jolt of electricity straight into his heart — and his cock.

“Okay, ready?” she asks.


One arm still covering her breasts, she reaches out with the other and grabs hold of Winston’s literally throbbing manhood. The sensation of someone else taking hold is awesome, it’s fantastic. At first, she simply feels her way over him like a tactile adventurer, exploring the ridged head, the vein underneath, even cupping his balls. Noticing his gasp when she touches his head, she begins to rub him up and down.

“Does that feel good?” she says. “Should I keep doing it?”

“Yeah,” he says. Her fingers are thin and feminine, and cold at first. But they quickly grow warm as she jacks him off.

She’s watching his face intently and Winston, feeling self conscious, tries to keep his face perfectly neutral. But he clearly doesn’t do a very good job because she asks him, “Are you going to cum?”

“If you keep doing it,” he says. “Can I see your breasts?”

She hesitates then lets her arm fall. “Are my nipples weird?” she asks.

A weird question, but he answers anyway. “No.” They’re long and puffy and crinkly. Textured. Nipples with character. Beautiful, he thinks, but lacks the courage to tell her so.

“Okay,” she says and keeps her hand motion going up and down. Her fist is tiny, but she has no trouble wrapping her fingers around him. He can feel every finger moving over his sensitive head. She takes her time, enjoying the sensation, becoming lost in it, like a pianist gently running her fingers along the keys. She strokes the full length of him — her hand sliding from the base at his groin all the way up to the tip. But as she grows comfortable, she begins to speed up her strokes, shortening them to focus just on the head. Soon, her small fist is flying up and down his cock, and Winston begins thrusting his hips up in rhythm with her strokes. It doesn’t take long for him to cum all over her hand and his stomach.

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