The Virgin Artist Ch. 01

Of course, disaster strikes. The next day, Winston meets Luna at La Parisian. She's positively glowing, but her news is less so.

"We're getting off -- going to island hop and rejoin the ship in Labadee."

"In Haiti? On Wednesday?"

"Yes. On Wednesday."

Wednesday is two whole days away. "Maybe I can convince my parents to do the same..." says Winston.

"Even then," says Luna. "I'll be with my parents the whole time --"

"Tell them you want to stay with the ship," says Winston.

"I can't, I -- "

"You should stand up to them."

"They're my parents, Winston. I want to go with them. Remember, this thing we have is just on a trial basis."

"Fine," says Winston and folds his arms, notices that Luna's upset and immediately apologizes. "Sorry. It's just..."

"Yeah. I know me too. Which is why..." She blushes. "Do you have a camera?"

"Yeah?"

"Here." Luna hands him a SD card. "But don't look at it until tonight -- and when you're alone okay?"

"Okay," says Winston.

"Cheer up," says Luna. "It's only two days. And I think you'll have a lot to think about." She leans in and kisses him on the lips. She tries to pull away but Winston holds her there, kissing her for a good half minute. Finally she pulls away, gives him an awkward wave, and turns and leaves.

#

Winston's in a sour mood the whole day. He even feels sour at being sour. Why should her being gone for a mere two days upset him so? He's on a Caribbean cruise for Christsakes. But his self pep-talk does no good. He feels vulnerable and knows it. Only the prospect of looking at her pictures gets him through it. After having supper with his parents at the cruise's burger joint, Winston returns to his room and gets out his camera and replaces the SD card with the one Luna had given him.

The first picture is of her holding a piece of paper on which is written: "Pick your favorite." The next picture is of her wearing a familiar green dress, that dress of what he supposes can be called their first date. The next has the dress off her shoulders, revealing the same shiny green bra she had worn after he had come on her breasts. Winston sets down the camera and takes off his pants and underwear and slowly begins to stroke his cock. He continues on with the pictures. The third picture has the dress completely removed; Luna is clad only in her pair of green underwear and bra. The fourth picture, she's naked but her arm covers her breasts and her hand covers her pussy. In the fifth picture, Luna is completely clothed again, in a pair of jeans and a white top that's tightly stretched across her breasts. The picture after that, she's flashing him, lifting up her shirt to reveal a yellow bra with black polka dots. In the next picture, her jeans have also been pulled down her olive thighs. Her underwear matches her bra, of course. She's a matching kind of girl. Yellow with black polka dots all around. Winston really likes that picture -- how sexual she seems -- and he stays on it for two minutes, his hand steadily pumping his cock, his eyes roaming the picture, memorizing every detail, searching for every sexual nuance, like a detective at a crime scene or an artist analyzing his model. Then he continues on. Despite the nature of the pictures, she's very shy. Her breasts are never fully revealed and her pussy only rarely; either underwear or her hands are constantly in the way. Even her face is often turned aside. She saves his favorite for last: pictures 43 to 49 have her first in a sexy black cocktail dress, and then a sort of strip tease: a black bra with lace trimmings that seems more mature, more erotic than her other bras, and then a matching black set of black panties with a very thin waist-band. He really likes picture 49 -- which clearly shows her breasts, spilling out over the tops of the pulled-down cups of her bra. But when he reaches the 50^th, and last picture, he moans out Luna's name and immediately comes. She must have used a timer. She's bent over her bed, completely naked, her ass in the air and facing the camera. He can see her curvy back and everything else too. Her pretty pussy out on display, and even her asshole. He knows exactly what this means -- sex. Actual sex. That's her way of saying that's what will happen when she returns. He thinks that's what it means, anyway.

The next day, Winston's parents invite him on a shore trip -- hiking on the El Salto del Limòn -- and he hops to it, hoping that maybe Luna and he will cross paths. They don't, and he spends the noon-time swimming in a cold pool beneath a 100 foot waterfall, its roar unable to drown out his dreams of Luna. He sees in all of nature's visual beauties a reflection of her curves, and in all of nature's auditory beauties a reflection of her voice. When he tries to draw anything, he only ends up drawing her.

After several hours of fevered thoughts, Winston returns to the ship, goes into room, gets out his camera, and masturbates. He turns to his favorite set of pictures and imagines being the one to pull that black dress from her shoulders, undoing her bra, slipping that small set of panties down her waist, her thighs, past her knees and ankles. He turns to the last picture and imagines bending her over the bed, grabbing hold of her waist, lining up his cock with her beautiful pussy, and sheathing himself inside. He imagines prim and proper Luna getting so horny that she starts dirty-talking. Oh Winston, fuck my little pussy with your long cock. Ram it in me. Harder. Make me come. "Oh Luna," he whisper-moans and comes.

He takes a short nap, dreams of Luna, and wakes up hard. He masturbates again. This time he focuses on the previous picture, the one that mostly clearly shows her breasts, and imagines rubbing himself in that delicious valley between her large globes. Her holding her tits together, providing friction, able to lick the very tip of his cock at the end of each his thrusts. He holds that image and climaxes the second time that night.

After Winston cleans himself and takes a short shower, a worry strikes him, and he heads to the convenience shop located at the front of the ship. He grabs a pack of condoms and surreptitiously glances around the store. After a wholesome family of four buy matching t-shirts and leave the store, he takes his condoms to the front.

"Hey, it's our hero Winston!" says the clerk. "It's me—"

"Timothy... Owens?"

"You remembered. Save any more girls? What're you purchasing for today?"

"Not exactly," says Winston and slides over the condoms.

"Not exactly," laughs Timothy. "I'll say!" He grabs hold of the condoms and goes to ring them up, hesitates, then hands them back. "Make those on the house."

"Thanks," says Winston. He turns to leave, then stops, and turns back. "Do you -- would you know of any private place?"

Stan stares at Winston then leans over the desk to look out into the corridor. "Don't tell anyone this but you know the actor Borden Saint?"

Winston nods. He remembers their photo shoot well.

"Well, he's off the ship and won't be coming back. Going to stay another two weeks and take a private jet back home. He's already moved out."

"So..."

"So," says Timothy. "His suite is empty, and I have the key." He reaches into his pocket and pulls it out. "I've charmed this sexy local beauty, but..." he raises one finger to the sky in a divine posture. "I believe your need is greater than mine." He hands the key over.

"Really?"

"You bet. The room number is on the key. Good luck and make it count," says Timothy, offering his hand. Winston shakes it and then returns to his room. Before he can get to sleep, he masturbates a third time, a long slow stroking set to one of her fully-clothed pictures. He takes his time and instead just thinks about her, the essence and totality of her. Without even coming, his hand still around his cock, he drifts to the land of dreams, soundly and pleasantly, like a baby rocked to sleep by the mother ocean.

#

He wakes up early, and the sharp edge has returned to his horniness, stoked by a night filled with Luna-laden dreams. He loads up her pictures and masturbates while thinking of their night of oral exploration. She swallowed his cum three times that night. Three times. The re-realization sets him off easily, taking him to one of those heady orgasms that seems to suggest but never delivers enlightenment. He cleans himself off, gets ready, and sets up shop at the La Parisian café with his sketch pad. He does a scenery sketch in a cubist style, the 'Boardwalk' filtered through a non-Euclidean universe, a warped, twisted, but ultimately cheerful hell.

At 10:30, just as he is finishing his second cup of tea, a pair of hands cover his eyes. "Guess who?!" says a high-pitched voice.

"Uh..." says Winston.

"Maddy! Stop that!"

The pair of hands reluctantly uncover Winston's eyes, and he turns around to see Luna's sister Madeline grinning impishly. Luna is still about twenty feet away and rushing closer.

"Hi Winston!" says Madeline.

"Hey... Maddy? Been climbing up any more railing?"

"Nope! Are you and my sister going to have sex? I told her she had to. I'm not old enough, or I would."

"Madeline!" says a horrified Luna and marches her sister back and plants her on a bench well out of ear-shot.

"Sorry," says Luna. "She doesn't really know what that means. She just heard it at school and keeps bringing it up because she knows it makes us all uncomfortable."

"Kids these days," says Winston. "Growing up fast."

"Mmhmm," says Luna, pulling out a chair and taking a seat.

"Did you have a nice island hop?"

"Yeah. Did you have a nice, uh, cruise?"

"Yeah. Wish I could have seen you though."

"Me too." She pulls her little notebook out of her back-pocket and retrieves the pencil that apparently has made a nest out of her hair. "So. Did you choose a favorite?"

Winston nods. "The last one, the black dress... and everything underneath it."

"I thought you might choose that one," she says and makes a quick note. "So, come to my room at --"

"No," says Winston. "I have a special place I want to take you. Meet me here at nine?"

"Nine-thirty," says Luna. "My parents always go to sleep at nine-fifteen. Okay. Until tonight?"

"Yeah," says Winston. "Until tonight." And as she walks away, Winston realizes that his heart is hammering in his chest. Just having a conversation with her... and he feels more alive than, well, he has ever felt before. He has to restrain himself from chasing after her, thinks about it, says fuck it, and does exactly that. He catches up to her, jerks her around, and does one of those ridiculous swooping movie kisses: here's looking at you, kid. Her eyes open wide in surprise but close as their kiss continues.

When he decides that he'll pass out if he doesn't get back to breathing, Winston pulls away. Madeline is staring at them with round eyes, her mouth rounded in a surprised O. Luna glances over at her. "I'll never hear the end of this from her now," says Luna. "But too late now." She gives Winston a quicker, more chaste kiss, and then twirls away. "Until tonight," she says and hurries off.

Winston nods. Until tonight.

#

Winston's dad had told him to bring a suit jacket "just in case" and Winston's glad that he had. At 9 o' clock, he puts on a pair of jeans, a belt, a dark t-shirt, and his suit jacket. He tells himself it's about as nice as he could manage with his given wardrobe, but then admits it's about as nice as he's ever dressed anyway. He's an artist, damnit! And artists have, well, artistic license. That's some rule.

He takes a couple deep-breathes and gives himself one of his pep-talks. Alright Winston, you can do this. It's as easy as painting waves. Yep, just go with the flow. Properly psyched up, he heads for the door, but just before he exits, his dad comes out.

"Winston! Where are you going?"

"Um..."

"Why the hell you all dressed up?"

"Well..."

"Oh you going on a date? Nice. Go get em, son," he says, yawns, and returns to his room.

Luna beats Winston to the café, and he takes the opportunity to look at her from afar. She's far more pretty in person in the black dress than she was in the picture. She's just more... vital, more alive. She just looks so perfect, so cinematic underneath the light of a fake streetlamp. And sexy too. The dress isn't that short, but short enough to show her knees. Her shoulders somehow manage to seem both feminine and strong. Luna's definitely not one of those overly delicate types, and Winston likes that. He also likes her really cute butt, the curves of which he can just make out dimpling the back of her dress.

"Hey Luna," says Winston as he closes the distance between them.

She gives him a little wave. "Hey -- look at you."

He shrugs embarrassed.

"I like it," she says. "Where are we going?"

"It's a surprise."

"But --"

"But you like things neat and orderly? Too bad," he says with a smile. He takes hold of her hand and leads her on. Though she's undoubtedly curious, her nervousness prevents her from asking him where they're going. But when they finally do arrive in front of the cabin, Luna says, "What?"

"It's Mister Borden Saint's cabin -- but he's staying on the island." He fishes out the key.

"How do you know that?" asks Luna.

"Just trust me." Winston slips the key into the door and opens it up. He begins to step inside, but Luna hesitates. "Come on," he says and pulls her inside.

The cabin is the plush in a way that only movie stars, rock stars, and wall street traders would fail to call excessive. It's at least three times the size of either Winston or Luna's cabin, and theirs are suites with double bedrooms and a private bathroom. Borden's has three rooms, a living room with its own little bar, a huge bathroom with a golden-framed mirror and a Jacuzzi bath, and a massive bedroom with a king-sized bed. The attached private balcony is equally enormous.

After they're done exploring, Winston leads Luna back to the bar and finds a bottle of champagne. "Thanks ol' Borden Saint buddy," he says as he pops the cork. He fills two champagne flutes and hands one to Luna. "A toast to the most awesome girl on the planet," he says.

Luna rolls her eyes. "A toast to our futures," and taps his glass. They both drain the fizzy alcohol in one gulp.

"So..." says Winston. "To the bedroom?"

"Okay."

Winston follows her into the bedroom, and she takes a seat on the edge of the bed and smooths her dress over her knees. Winston sits next to her, hands firmly gripping his knees, his beating like a demon-possessed drum.

"So..." says Winston. "So I guess there will be 'fucking around' after all."

"Yeah..." says Luna. "Yeah." She turns to look at him. "We're here to learn, and... I like you. I don't want anyone else to take your virginity before we have a chance to see each other at college. I want to be the one. I want to be your first."

"...see each other at college?"

"Yes," says Luna. "Do you still want to date me after we get back?"

"Yes! Absolutely. Totally, Luna. I was being totally serious when I said you're the most awesome girl on the planet. You are completely, totally awesome. And I want to be your first too."

"Okay," she says and pulls out her ubiquitous notepad and pencil from god knows where. "I've got a list of positions --"

Winston interrupts her with a deep tongue-twisting kiss. He stops, moves her hair back behind her ear, and kisses her again. The list and pencil fall by the wayside. Winston kisses her neck. He slips her black dress off her shoulders and kisses her sharp shoulders, and then the tops of her breasts. Luna pushes him back and slides the sport coat off his shoulders. Winston tosses it aside and pulls his shirt up and over his head in one motion. He moves back toward her, but Luna stops him.

"No, your pants too."

Winston stands up and undoes his belt, the metal buckles scraping against one another. He snaps out the button on his jeans, pulls down the zipper, and slips his jeans and boxers down. His hard cock springs up proudly. He kicks his pants and boxers aside.

Luna hikes her dress up her hips and begins to pull down her panties but Winston stops her. "No. I'll do it."

Without waiting for permission, Winston leans back in and slides his hands up her athletic legs, toned from countless hours of practice at her jujitsu dojo. The thin waistband of her panties does little to hide the smooth flesh of her flank, and Winston takes the opportunity to slide his hands up to squeeze the two globes of her ass. He hooks his two fingers in the band and slowly pulls down her underwear to reveal her beautiful pussy, already wet with her arousal. Seeing it again after the two-day hiatus, Winston feels a sudden hunger and says, "I want to taste you."

Luna nods, and Winston finishes pulling her black panties down past her knees and ankles, feeling a déjà vu with how closely this matches his fantasies. After Winston drops her underwear to the floor, Luna scoots a little farther up the huge bed, sliding her dress up to her hips. She spreads her legs and says, "Go ahead."

Despite his hunger, Winston takes his time. He kisses her ankle, her calves. He notices for the first time a little moon-shaped birth mark above and to the left of her knee and kisses that. He licks and gently bites her thigh. His tongue makes a circuit around her pussy, carefully skirting the edges, carefully avoiding the dangerous areas. Only after Luna chastises him with a half-whispered, "Winston..." does he finally spiral in to the folds of her pussy, slipping the point of his tongue inside her, inside the place that he hopes his cock will soon be. After their night of oral exploration, he knows exactly what she likes, and proceeds to give her just that, sucking on her clit, making little spirals around it with his tongue. But after a handful of minutes, and before she reaches orgasm, Winston stops.

"What are you doing?" she asks.

"I need to be inside you," says Winston. It's true. His desire is a need, the separation of their flesh is a palpable lack, a tangible disconnection with how things should be.

"But... yes, okay."

"I have condoms," says Winston, glancing toward his jeans.

"No need," she says. She slides up the bed until she's lying back with her head against the pillows. Winston joins her and climbs between her legs, until his cock is inches away from her pussy. He watches Luna's face: she's biting her lip and gently shaking from nervousness. She's balled up her fists.

"Are you okay?" asks Winston.

She nods.

"Relax," says Winston. "Or you won't be ready for Mr. Johnson?"

Luna laughs in spite of herself and then says, "Don't say that."

"Sorry," says Winston and then takes hold of his 'above average' manhood and after a couple seconds of searching, places the head inside of her pussy. He gently sinks himself into her. When he's about 4 inches in, she says, "Yes, that's good."

Winston stops. "Should I stop? Does it hurt?"

"Not really," says Luna. "A little uncomfortable. Just take it slow?"

"Yeah," says Winston, relieved. No matter that he masturbated four times -- or was it five? -- in the past two days. He's so turned on that he's afraid any real movement would have him immediately coming. He doesn't dare look down at his cock inside of her, knowing that the image will set him off. Instead he leans in and kisses her freckled nose, trying to distract himself from the extraordinary pleasure of her womanhood.

It works, sorta. After making it past that initial rush of pleasure, Winston settles on a steady rhythm of short, gentle strokes. As tight as her virgin pussy is, she's very wet, and he can slip himself in and out easily.

"Do you like this?" Luna asks. "Does my -- does it feel good?"