Chapter I: First Date
by Mark Singer ©
Dan was a little nervous as he pulled in front of the big white house. He'd been enthralled with the looks of Jennifer Grayson for close to three months, ever since he'd seen her in the halls of school, and was as close to "in love" as any eighteen year old guy could be.
He'd only recently gotten up the nerve to ask her out, and had spent a good share of his time simply fantasizing and watching her in the halls and in class. Almost every boy at Washington High was doing the same thing.
Jennifer was the type of girl that was simply too beautiful to be approached by the normal high schooler. Her habit of wearing short skirts that showed her incredibly long legs, and her obvious distaste for bras made her food for every boys dreams.
Jennifer was any boy's dream come true. Long, thick brown hair that reached almost to her waist, a wonderful sense of humor, a lot of brains, and a body most men, sixteen or not, would kill for. Although she didn't possess large breasts that most of his friends lusted after, hers were firm and high, with nipples that stood out proudly against her blouses and sweaters.
And she had more of a sophisticated style of dressing than most of her friends. It was definitely sexy, but also very classy. In fact, Jennifer Grayson oozed sex. It radiated from her with each and every move she made.
Jennifer's only problem was that, because of her classy, sexual exterior, she appeared out of reach to most of the guys. She'd been dating fairly often, since she'd transferred from her old high school, but usually they were just one night. She hadn't chanced to meet Mr. Right yet. Or, for that matter, Mr. Okay.
What Dan didn't realize, as he pined for her from a distance, was that Jennifer had been watching him, too, and hoping he would get up the nerve to ask her out! Jennifer had her own fantasies.
They'd finally met on the beach during the summer, and, he had to admit, it was her body that attracted him first. She'd been wearing a small bikini that barely covered her full, upturned breasts, and, although it wasn't a 'thong', had ridden up into her ass crack, exposing most of her butt to all who happened to look.
She was also eighteen, although she carried herself with the poise of a worldly model. She also carried herself within a body that was definitely worthy of modeling.
And on that day at the beach, every male eye was following her around. He'd gotten up the nerve to introduce himself, and was pleasantly surprised when she reacted positively to his overtures.
He especially liked the way her eyes drifted over his body as they talked about the day, the beach, and life in high school.
And he was mildly surprised when she accepted his offer for a date that coming Friday. When he asked her out, she merely said "Sure...call me..." and had walked away down the beach, her hips swaying in a wonderfully sexy way. It wasn't until later that he realized he didn't get her number.
If this were a movie, there'd be a few minutes of comic scrambling as Dan combed the beach, looking for his lost lady. Finally, he ran into a girlfriend of hers he'd seen her with earlier, and finagled the number from her.
That evening, to his major relief, he dialed the number and heard her sexy voice on the other end. And, after a couple minutes of chatter, they'd made a date for this evening.
All this to explain Dan's nervousness as he sat in front of her house. He'd dressed rather casually, in Docker's and a knit shirt, and he was hoping that Jennifer would approve.
Dan considered himself very lucky, although his young ego would never admit that to anyone. He knew all the guys envied him, and he liked that. but it was Jennifer, most of all that he liked. Tonight was going to be their first, official "date".
He felt his cock stiffening inside his pants as he thought of her.
He had suggested a light dinner and a movie, but she had countered with the suggestion of getting a bottle of wine and going to the drive-in. She'd said she could 'liberate' a bottle from her parent's pantry.
When Dan had asked what was playing at the drive-in, there was a pause on the line before she whispered..."Does it matter...?" Jennifer loved to tease, and she did it very well. He'd felt his cock stiffening as their conversation continued, her sexy voice driving him crazy.
When they'd finally hung up the phone, Dan went to the bathroom and masturbated, his cum shooting in a wide arc into the sink as he thought of Jennifer.
Back in his room, he drifted off to sleep with visions of this lovely lady dancing in his head. The next three days seemed like an eternity as he waited for this night to arrive.
Now tonight, as he sat in his car, waiting for his hardness to subside, he tried to control his excitement. Finally he felt ready to walk the final 'mile' to the door. He took a deep breath as he pushed the doorbell.
He was expecting to be greeted by a stern faced 'father face', and breathed a sigh of relief when Jennifer herself opened the door.
"Come in, Dan..." she breathed. "My parents are at a party for another hour or so, but I'm almost ready."
He was glad to see that she'd dressed as casually as he had. His eyes drifted over her body as she walked up the stairs. She told him to make himself at home in the parlor, but instead, he stood in the foyer, watching her ass as she walked up the steps.
She wore a short denim skirt that accented her ass beautifully, and he felt himself getting hard again as he watched her walk. She paused on the top landing and turned to him as if she KNEW he'd be watching.
"I'll be right there, Dan..." she smiled, then moved out of sight. Dan shook his head in disbelief at his luck, and went to sit in the living room.
Jennifer was true to her word. In less than five minutes, she appeared in the doorway. She stood there, her leg cocked to one side, and her hands clasped behind her back. Dan sighed inwardly as he drank in the sight of her. She wore sandals on her feet, and Dan's eyes started there, moving slowly up her long legs, over the denim skirt and up to her chest.
She wore a short cotton top, kind of 'T-shirt' material, but with buttons up the front. The bottom was cut to about three inches above her belt, exposing a delicious expanse of her midriff. The bottom hem stayed away from her skin, held out by her firm breasts
It was painfully obvious to Dan that she'd opted to not wear a bra. Her nipples stood out against the cotton, and seemed to expand as Dan watched.
He whistled under his breath.
"So you approve...?" Jennifer whispered with a smile. Dan could only nod, his mouth suddenly dry and unmovable. Jennifer's smile grew as she watched his discomfort.
"So let's go, shall we...?" she laughed, pulling a short jacket out of the closet. She turned to Dan as he walked up to her, and put the jacket over her shoulders. The movement of her arms caused her tits to press against the cotton of her shirt, and made Dan lose his voice once again.
They were almost out the door when Jennifer asked him to wait. She ran inside and returned in a second with a bottle of White Zinfandel under her jacket. She looked at him with an evil smile.
"It'll help us to relax...." she grinned, and led the way to his car.
Dan held the door for her as she got in and whistled again as she let her skirt ride up her thighs as she slid over the seat. He shook his head as he shut her door and ran over to his side.
He grinned when he got in, seeing that she had moved over to his side of the seat. Her denim skirt stayed high on her thighs.
Dan pulled away and headed for the drive-in. His heart was pounding in his chest as he paid the attendant and drove into the lot. It was already fairly crowded, and as Dan drove from lane to lane, looking for a good spot, he felt Jennifer's hand on his leg. He slowed and turned to her.
"We can see pretty well from the back, you know. There's a couple good spots up there..." She raised her eyebrows and grinned at him. Dan didn't hesitate, finding a spot in the back, and away from the concession stand, almost immediately.
He parked the car, and reached for the speaker, rolling up the window to hold it securely. He nervously tried to adjust the sound and the position, but finally ran out of things to do. He sighed and turned to Jennifer. He found her leaning back into the seat, a huge grin on her face.
"Wine...?" she said, offering him the bottle. He opened the wine and they sat there in the dim light, drinking from paper cups and watching the first movie. It was a movie called "Body of Evidence" with Madonna and Wilhem Defoe. As it turned out, it was pretty erotic thriller, with a lot of excitement and a fair amount of nudity. And there were a number of shots of Madonna nude and semi-nude.
Dan found himself getting engrossed in the film, many of the scenes were making his cock harden in his pants. In one scene, Madonna was standing on the hood of a car, in a parking garage. Defoe was standing in front of her as she hiked her skirt up her legs, exposing her stockinged thighs and black garter belt. Dan was engrossed, but was pulled from his hypnosis, by Jennifer's' voice.
"Do you think she has nice breasts...?" Jennifer asked him "innocently", staring at the screen.
Dan's brow furrowed. He knew from experience that this was a loaded question. He thought for a moment before answering. He turned in his seat, letting his eyes drift over Jennifer's body. They settled on her breasts and then moved back to her face.
"Madonna has a pretty decent body..." he replied, "but it's her attitude that I find attractive. She enjoys what she does and it's obvious." He watched Jennifer as she turned to him, listening intently. He felt instinctively that he'd chosen the right approach in his answer.
"It seems to me", he continued," that she understands how people think, and she enjoys the game of sex as much as the physical part." He hoped his answer would suffice.
Jennifer looked at him for a minute, a blank expression on her face, then smiled broadly. Dan mentally released a sigh of relief. His method of answer had been the right one.
She leaned forward, placing a hand on his thigh, and kissed him lightly.
"Good answer..." she whispered. Dan grinned and put his arm around her, squeezing her tight as they turned back to the screen. Jennifer kept her hand on his leg, and the feel of her warm palm on his thigh made his cock bloom to full hardness. Out of the corner of his eye, he saw Jennifer look down at his bulge, then turn back to the screen, a sexy grin on her face.
They watched the actors making love on the screen, and Dan was getting extremely turned on. He felt his cock was going to rip through his pants as Jennifer began to stroke his thigh lightly. His own hand began to move up and down her soft arm, as the smell of her perfume began to take it's toll on his senses. Jennifer responded by cuddling closer, leaning her head on his shoulder.
Dan was in heaven. He was sitting in a dimly lit car with the girl of his (and everyone's) dreams, with his arm around her and her hand on his leg. His bravery increased as the moments ticked by. As his hand moved up and down her arm, Dan spread his fingers wider. His thumb barely grazed her right breast as he passed and he waited for a response.
When none came, he grew bolder. On the next pass of his hand, his thumb made heavier contact with the side of her tit, being obvious in the fact that it was not merely an accidental contact.
Jennifer sighed and moved even closer, her own hand continuing to move along his thigh. Dan's heart was pounding in his chest as he took the next step. This time he allowed his fingers to join his thumb, running his hand over the soft curve of her breast. Her skin felt very warm, even under the fabric of her shirt.
Dan got bolder, moving his arm around and running his hand over her breast, cupping it lightly, and feeling the hardness of her nipple as his palm brushed over it. Jennifer let go with a low moan, sliding her hand higher on his thigh.
Dan continued to play with Jennifer's right breast, then boldly moved to her left, cupping and squeezing that one also as they silently watched the movie.
He had a moment of fear, when Jennifer pulled away slightly. She drew her head away from his shoulder, and leaned back into the seat. Dan's first thought was that the fun was over before it began, but Jennifer was merely adjusting her position to allow him more comfortable access to her breasts.
She looked up at him and smiled. "That feels good..." she whispered, then turned back to the movie. She leaned her head against the seat back and her eyes closed to thin slits.
Dan thought he was going to have a seizure right then and there, his heart was pounding so fast. He pushed a finger in between two buttons, and felt her bare flesh underneath. Pressing on he found the hard nipple of her left breast, running his fingertip over it again and again.
Jennifer sighed and moved her left hand higher up his leg. Her hand was still a ways away from his hard-on, but her new position caused her elbow to make contact with it. Dan groaned and he saw Jennifer smile. She pushed her elbow down against his cock and squeezed his thigh. Dan was afraid he'd come right there, but steeled himself and held back. It simply wouldn't do to come in his pants on their first date. He turned his mind from the burning in his pants, and returned his attention to his fingers.
His breathing was ragged as he made contact with the top button of her blouse. He flicked it open effortlessly, causing Jennifer to begin to breath heavier as well. He quickly undid four of the buttons and reached his hand inside her blouse.
"Mmmmmm..." Jennifer sighed as Dan cupped one naked breast, then the other. She looked up at him again, a look of lust on her face.
"Do you think I have nice tits, Dan...?" Dan looked down at her. Her lips were parted and she was breathing through her mouth. Her lips glistened in the flickering light of the movie screen.
Dan grinned at her foolish question. "You've got the most incredible body I've ever seen, Jennifer." he said sincerely. He cupped her breast and then gently pinched her nipple. "Yeah....I think you have nice tits..."
Jennifer smiled and tilted her head up to him. Dan leaned over kissing her lightly, then harder as he felt her tongue brush his. Jennifer moaned and turned towards him, pressing her chest against his.
Dan almost screamed as he felt Jennifer's right hand move over to his thigh. She broke their kiss, leaning back and looking into his eyes as she slid her hand higher and higher up his thigh. She was grinning as she continued higher. Her hand cupped his full balls and then moved to cover his hard cock.
"God, Dan..." she whispered, "You're hard as a rock..."
Her eyes closed to slits once again as she wrapped her palm around him and began a rhythmic squeezing. Dan groaned a gain and returned his lips to hers. Their tongues intertwined, dueling wetly as they breathed each other's air. Jennifer was moaning as they kissed and her hand was working wonders on his cock, running up and down it's full length, squeezing and pawing.
Dan's left hand was busy also. He undid the last of her buttons, and pulled the thin cotton away from her tits, exposing them to the cool night air. Her naked flesh felt wonderful under his hand, and he gently teased and stroked her breast, paying particular attention to her nipples. She'd shown that she enjoyed that, and the only thought he had was to pleasure this girl as well as he possibly could.
Well, maybe not his ONLY thought.... His breath caught in his throat as he felt Jennifer move up to his belt buckle. He pulled back allowing her the space to work. He began to moan as she undid his belt, then unbuttoned his pants. She was kissing him fiercely as she pulled his zipper down and reached her hand inside his open pants. He groaned loudly as she pulled his underwear back and wrapped her hand around his hard cock, pulling it out into the dim light of the car. She began to stroke him up and down, jerking him off as they continued to kiss.
Dan dropped his hand to her thigh. Jennifer thrust her tongue deep into his mouth and spread her legs wider, inviting him higher. Dan grinned into her mouth and slid his hand up until he felt the hot dampness of her panties under his palm.
There was no more teasing now. Both of them were fully intent on exploring their lustful fantasies. "You've got a great cock, Dan... Mmmm...it's so hard.. "
Dan was excited beyond belief. He'd never been with a girl who so obviously enjoyed sex as much as he did. He'd gotten hand jobs before, at this same drive-in and in this same car, but always from girls who had to be "coaxed". He'd never had a girl take his cock into her hand so eagerly. And he'd never, ever heard a girl use the word "cock" as she stroked it.
Jennifer stroked him faster, as Dan moved her panties aside. She stiffened when his fingers found her naked pussy lips, then she let out a long "Aaahhhh...." as he worked his fingers between them. Dan flicked his thumb lightly over her clitoris, stimulating her further as he slid his finger into her pussy.
She was wet enough to allow him effortless passage, and he pushed deeper until his entire middle finger was inside her. Jennifer's hips began to move, and he followed her rhythm, fucking his finger in and out, continuing to pay attention to her clit at the same time.
Jennifer broke their kiss, pushing her face into Dan's shoulder. Her hand maintained it's grip on his cock, but her stroking stopped, much to Dan's relief. He'd felt he was going to come at any second, and didn't want to spray all over the two of them. He looked down at this lovely vision beside him.
He continued to slide his finger in and out of her pussy, as he gently pushed her back onto the seat. Jennifer didn't resist at all, leaning back until her head was against the passenger door. She was an incredible sight as she lay there. Her skirt was hiked up to her hips, and her blouse lay on either side of her firm tits.
Dan continued to finger her as she looked up at him with smoldering eyes. She brought both hands up to her tits, squeezing them as she spread her legs wider.
"Make me come, Dan...." she panted, "God, your finger feels so good inside me...Please make me come...oh....yes..."
Dan was happier than he'd ever been in his short life. Jennifer's hand had felt wonderful on his cock, but he felt even better to know he was pleasuring this girl of his dreams as much as he was. He'd never been with anyone who was this exciting and free. He only wanted to do more.
Although his experience with cunnilingus was limited, so far, to his fantasies, he didn't hesitate for a moment. He leaned forward, until the sweet smell of Jennifer's pussy greeted his senses. He pushed his face deeper and began to lick her wet pussy with the tongue of a master.
Jennifer groaned as she saw his head begin to descend, anticipating something she'd only dreamed of. She stifled a scream as Dan began to lick and suck her pussy. She reached down with both hands, cradling Dan's head as he licked the full length of her, starting at her asshole and ending at her clit. He sucked her clitoris into his mouth and ran his tongue over it in tiny circles, then he repeated the process, over and over, driving Jennifer over the edge.
She spread her legs as wide as the car would allow, knowing that she must look like a complete slut if anyone happened to pass the car and look inside. She truly did not care, though. In fact, the thought of someone watching her as she got her pussy eaten only heightened her lust.
She was about to pour her cum into this handsome boy's mouth, and that was ALL she cared about right then. She began to move her hips up and down, in the opposite motion of Dan's tongue. She could feel her orgasm approaching, and knew it was going to be a good one.
Dan could feel Jennifer tensing up as he licked and sucked her. He was loving every aspect of what he was doing. The sloppy wetness of her pussy as it moved over his face was particularly exciting. His whole lower face was covered with her wetness, and the taste and texture of her juice on his tongue made his cock throb. But he especially loved the smell of her pussy as her orgasm approached.
He began to shake his head from side to side as he ran his tongue up and down her lips. Each time he made contact with her clit, Jennifer would let out a tiny scream. He knew she was close and doubled his efforts.
Jennifer stiffened, and pulled Dan's head tight against her cunt. Dan grinned and continued to lick, holding his head still. Jennifer's hips began to shake like San Francisco, and she released a huge sigh.
Dan felt her juice begin to flow into his mouth. Jennifer began to moan, shaking like a tree, and Dan sucked like a madman, as she filled his mouth with her cum. She began to moan over and over and her hips started to fuck against his face as her orgasm overtook her and she spilled wave after wave of cum into Dan's sucking mouth.
She'd never, EVER, had an orgasm this powerful! She humped against Dan's tongue as she pulled him deeper with her hands. She wanted to scream out, but a small voice in her head told her they were still at the drive-in, and she was able to control her voice. But she continued to moan low as she poured load after load of sweet cum into Dan's greedy mouth.
Finally, after what seemed like hours, she collapsed, exhausted, against the door. She looked down at Dan and began to laugh with sheer pleasure.
"God!! That was incredible! Dan...that was the most incredible....that was...oh my....Dan! Where did you learn....Oh....my...!"
Dan looked up and grinned at her. His face was covered in her juices, and he was licking his lips to get as much as he could into his mouth. He didn't bother to tell Jennifer that it had been his first time. Some things are just better left unsaid. She reached down and pulled his head up to hers. she kissed him hard, thrusting her tongue deep into his mouth, and when she tasted her own cum on his tongue, began to lick his lips and face, drawing her juice into her mouth.
Leaning over her, as he was, Dan felt the wetness of Jennifer's pussy against his hard cock. As they kissed, he began to slide his cock against her slick lips. Jennifer groaned and parted her thighs, loving the feel of his meat as he slid it's length along her outer lips.
Dan pulled his hips back slightly, causing his cock to stand out straight. He positioned his cock head against the entrance to her pussy, and groaned when he felt her lips fold around him. Jennifer tensed, though, and pushed his hips back.
"We can't....Dan...we can't..I mean I've never...I've never done that...." Dan stopped his forward progress. He was disappointed, but looked down at her with a grin.
"That's okay..." he whispered. "Either have I..." Jennifer relaxed visibly. "Maybe some other time...huh?" His grin was disarming, and Jennifer smiled. She looked up at him with love.
"Yeah..." she replied. "Definitely another time. Thanks, Dan..." She reached a hand between them and found his hard cock. Dan groaned as she wrapped her fingers around it. She looked at him with a big grin.
"But there are other places this can go, you know...." she teased. She began to stroke him as Dan began to push in and out of her fist. "Maybe we should try them first...." She grinned again and began to sit up, pushing Dan backwards as she did.
To Be Continued...
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