Girls Who Park

****Author's note: I am entering this for the Literotica Winter Holidays Contest, so if you enjoy this story please give it a vote! This story does contain mild themes of reluctance. All characters in this story are over the age of 18.

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The doorbell rang, and Gladys Newsome bit her dark red lip with excitement as she put on her pearl earrings and matching necklace. She'd agonized over this outfit for weeks, ever since George Miller asked her to the Christmas Eve sock hop at the nicest jazz club in town. Gladys' shoulder length brown hair was perfectly styled in pin curls and pulled back at the front, her curvaceous body was complimented by a dark red sweetheart neckline dress made of the most luxurious velvet material in New York, and she wore a white fur (genuine of course) shrug. Her dress fell to mid calf, complimented her slender ankles, which were further accentuated by matching velvet kitten heels. Gladys was a senior in high school and ready to start looking for a husband, and the only other family in Manhattan in 1947 that was as wealthy as hers were the Millers.

Gladys descended the staircase, her white satin-clad hands gently gliding over the banister. George was at the bottom, shaking her father's hand and kissing her mother's. He had a charming smile on his face. George offered Gladys his arm and she took it gratefully, imagining what it might be like to be on his arm every night for the rest of their lives. Gladys' mother subtly eyed her ensemble and pursed her lips.

"Gladys, you left your pocketbook in the parlor earlier," she said, and Gladys reluctantly let go of George's arm to step into the other room with her mother.

"Don't you think you were a little heavy-handed with the lipstick, dear?" her mother inquired gently, handing Gladys the aforementioned pocketbook, "You don't want to give this boy the wrong idea."

Grateful her mother couldn't see the neckline of her dress underneath her shrug, she replied: "Mother, the rest of the girls will be wearing lipstick. Unless you want me to be an old maid living with you and Father until I'm 30, I need George to ask me to go steady tonight. I need all the help I can get. George is a respectable young man, he won't do anything I don't want him to." Mrs. Newsome nodded reluctantly.

"Have a good time, dear. This would be an advantageous match for the company, but remember not to damage your reputation in the process."

Gladys and her mother left the parlor just as George was shaking Mr. Newsome's hand one final time.

"Have her home by midnight," Mr. Newsome said with a smile, and Gladys' heart nearly leapt out of her chest. Her father had never let her stay out this late, he must have really wanted tonight to go well.

The Newsome's had owned a small slew of car factories prior to The War, which had been temporarily converted to munitions factories. The demand for munitions meant the Newsomes had opened more and more factories, their wealth quickly accumulating. They were "New Money", and the Millers were blue bloods, able to offer the status and business connections the Newsomes desperately craved. The Millers wanted to expand their business prospects to automobiles. It was 1947, the automobile business was booming during the newly re-established "peacetime economy", so both families needed this match to go smoothly.

Gladys and George walked out to his brand new 1946 Triumph Roadster, the convertible top was up of course, and George opened Gladys' car door. She smiled at him and blushed as he shut her door, and then walked around to the driver's seat. Gladys was over the moon, her heart pounding beneath her pert cleavage. She shivered, the cold reaching her shoulders from underneath her mostly decorative fur shrug. The car roared to a start and George began the 15-minute drive to the jazz club. The city lights sparkled against the snow that hadn't been trampled on. The two found they had much to discuss as George attended an all boys school, and Gladys went to an all-girls school and were soon chatting along and laughing about the nuns who taught them, and how they would both soon be graduating. George was to study under his father to one day inherit the family business. His family was insisting on sending him to an Ivy League school, because only an educated man could handle business affairs of that magnitude.

Once the couple arrived and entered the dance hall, George checked her shrug at the door. His hungry, devilish eyes swept over the way her pearls highlighted her collarbone and her ample cleavage, the way her curls brushed her shoulders. This dress was very revealing, and George felt a stirring in his trousers.

"Ms. Newsome, may I have this dance?" he asked, offering his hand, and she accepted. They walked to the dance floor together and began to dance. Gladys hadn't even bothered to fill out her dance card, every dance was for George and George alone. George was a perfect lead, firm but not demanding, his hand resting gently on her tiny waist and guiding her hand with confidence. Gladys found herself blushing as she considered where else George's confidence might be of use to her. The air smelled like cinnamon and mint as the pair danced; they were a perfect match. It was as if they'd danced together dozens of times before.

While George was acting the perfect gentleman, his thoughts were less than gentlemanly. The Christmas lights glittered above the dance floor, and like any good Catholic family, the Millers celebrated Christmas. But as George looked down at Gladys, her cleavage gently brushing his chest, he had absolutely no intention of leaving room for Jesus.

The jazz band played a slow dance, the singer crooning I'll be Home for Christmas as George and Gladys slowed down. They were swaying in the corner by the large Christmas tree, the colored lights and glittering ornaments making it seem that much more romantic. The two were pressed together closer than what would've been considered decent, and George leaned down to plant a soft kiss on Gladys' cheek. Her cheeks turned bright pink, making her innocence that much more enticing to George. George was careful to angle his hips away from Gladys, slightly, not wanting her to feel his gradually hardening cock. He moved his hand from the small of her back to her true waist, underneath her arm. George's thumb gently brushed the very bottom of her breast, subtly enough that he could apologize or even deny it had happened with little repercussion. But the skin underneath Gladys' dress was on fire, and she felt an unfamiliar heat growing between her legs.

"Is it me, or is it a little warm in here?" George whispered in Gladys' ear, his hot breath skating across a spot on her neck where she'd always longed to be kissed. She nodded, and George retrieved her shrug from the coat check as they stepped outside. There were some young men smoking fags to the side of the door, and Gladys coughed as the smoke blew in her face.

"Shall we go sit in the car?" George suggested, and Gladys froze. She knew exactly what happened when girls her age agreed to 'park', but she was so flustered and George's bright blue eyes seemed so kind and gentle. So, against her better judgment, she didn't protest when George had the valet bring his car around, and they found a semi-secluded spot around the corner to sit.

The leather seats were cold against Gladys' skin so George slid across the bench seat a few inches and put his arm around Gladys, under the guise of keeping her warm.

"I'm having an amazing time with you tonight. You're the prettiest girl I've ever danced with," George said, gently stroking her cheek.

"Thank you, I'm having a fine time myself," she breathed, every touch setting her aflame.

"Could... Could I maybe kiss you?" George asked. Gladys' mouth went dry, this would be her first kiss. But how could she refuse? She nodded and George leaned in, planting a chaste kiss on her very red lips.

Gladys gasped a little, involuntarily, and hoped it went unnoticed.

"Did you like that?" George asked, and Gladys nodded. So George leaned in for another one, this one with a little more passion. That heat grew between Gladys' legs and this time she definitely gasped against his mouth. Gladys pulled away and George looked a little disappointed.

"I'm not that kind of girl, George," she said softly.

"I apologize, I just got a little ahead of myself is all. Let me take you home."

"No!" Gladys exclaimed, it was only a little after 10, she knew her father would be displeased if she arrived home so soon, regardless of her success.

It was at this moment that George knew he had her where he wanted her. She needed this match for her family, she'd worn a provocative dress to catch his attention, and if she told anybody about what was going to happen next, it would ruin her and any decent marriage prospects she could possibly have. It was Christmas Eve, and George knew he could walk right back into that dance and have the news of Gladys' fictional promiscuity spread before they even arrived for Christmas morning service at Church the next day.

George untied the ribbon of her shrug, and the cold air hit Gladys' exposed flesh, giving her goosebumps. He traced a finger along her newly exposed collarbone and a shockwave of pleasure ran down her spine, causing her to push her chest forward in a sudden movement. George seized this opportunity, snaking a hand around her waist and pulling her toward him. He kissed her passionately, and her breasts heaved as her breathing sped up. She didn't know what she wanted, but she knew if she didn't play along with him he could tell anybody whatever he wanted to. She never should've come out to the car with him, but she also couldn't stop kissing him.

George leaned down to kiss her neck, and she gasped, now knowing she wasn't going to put a stop to whatever was about to happen. She could feel how damp the crotch of her panties was, and bit her lip when George ran his thumb once more across the underside of her breast. She stiffened momentarily, but George pulled away.

"You're so beautiful, Gladys," he said, and she melted once more, saying nothing when his hand moved up to cup her breast over the fabric. She hadn't worn a brassier, counting instead on the support from the stiff velvet of her dress. The dress crept lower down her chest, until her nipples were all but exposed.

"Should we stop?" she asked, but then George lifted one of her breasts out, gently massaging her nipple. She moaned, arching her back, her other nipple coming free as she unintentionally pushed her perky tits right into George's experienced hands. He leaned down to take one of her pink nipples into his mouth, his left hand inching her skirt up her thigh to reveal her lace topped stocking. His hand went further up her skirt, his thumb finding her erect bud over her panties. She moaned out loud and George kissed her to quiet her, lest she draw attention to them. She rocked her hips on his hand as he played with her clit, making her feel things she'd never felt before. She never knew anything could feel like this, when her mother had talked to her about sexual relations, she made it seem like a chore. But this... this was amazing.

George moved Gladys' hand to his trousers, letting her feel his hardness for the first time. Gladys had no idea what a penis looked like, and she was both nervous and excited to find out.

George shifted Gladys so she could straddle his knees, her back against the dash, with plenty of space between her and his belt. George unbuckled his belt, pulled down his briefs, and let his hard cock spring free. Gladys froze, staring at the mushroom head, the tiny slit leaking pre-cum. Suddenly, it hit her that George meant to deflower her.

"We need to stop," she said firmly. But nothing covered her breasts besides the very bottom of her pearl necklace, and her skirt was pushed up her thighs. George wasn't going to stop now.

"Don't be a tease," he said, "you want this, and you want me." Gladys looked down at his cock, and then at George's blue eyes. She remembered what it felt like to be on his arm, and in his arms, on the dance floor. They could be engaged by next Christmas and married the one after. Maybe she would even have a Christmas wedding, the photos beautifully backdropped by glittering snow, their gifts wrapped in red and green paper...

"We shouldn't do it before we're married," she said, referring to their Catholic roots. But as soon as he had said "tease", her mind was made up. "Tease" was just as bad as "hussy". She was in over her head.

"We'll be married soon enough," he said. And excitement blossomed in her chest. All she needed to do was make love to him, and he would be hers. Her family's future would be as good as written in stone, she would be taken care of for the rest of her life.

"What do I do?" she asked. George grinned at this, and helped her slide off her panties, even in the awkward position she was in. George easily lifted Gladys up by her hips, teasing the head of his cock at her sopping wet entrance, hidden only by a short, well-trimmed layer of curls.

"This will hurt a bit," he said gently. Although he had wanted her pussy, and he had been willing to do pretty much anything to get it, he wasn't a monster. So he thought, at least. Gladys nodded, squeezing her eyes shut. "No," George said, "Relax, open your eyes, I want to see you. This will feel much better if you relax your muscles." Gladys obeyed, opening her eyes as George pushed the head of his cock into her entrance, sliding in millimeter by millimeter.

"Ow!" Gladys exclaimed as she felt some pressure, a searing burst of pain, and then it was over. She was resting on George's lap, his cock buried deep inside her.

Gladys squeezed the walls of her pussy and shifted her hips a little, exploring this new feeling. She'd never even touched herself in the dark of the night. Having him inside her felt so good, she decided, partially because it was so deliciously wrong. She began to rock gently on his cock, moaning when his swollen member brushed the right spots. George's head was leaned back against the seat, his eyes taking in her gently swaying breasts and hard nipples.

George's cock was about average, maybe 5 inches long and two finger lengths wide. But his cock parted her folds, and when he lifted her red skirt he was treated to the view of his member disappearing inside Gladys' fuck hole. She began to grind on him harder, a little faster, moaning and gasping as she took him in her tight snatch. She leaned forward to use the seat to support her weight, her perky breasts and puffy nipples now swaying directly in George's face.

George reached up to fondle her, making her moan. She gasped as he took one of her pink nipples into his mouth, licking and sucking, and had to bite her lip to keep from crying out when he used his teeth to gently bite down. His hands snaked underneath her dress and to her pert ass, squeezing and even gently smacking her as she rode him.

"Oh my god!" she gasped, taking the Lord's name in vain. "Please don't stop!" but George couldn't have stopped if he'd wanted to, she was riding him so vigorously and had a vice-like grip around his shaft. Gladys yanked her tit out of George's mouth and leaned back with her back against the dash. She kicked off her heels and put her stocking-clad feet on either side of George's lap on the leather seats. George lifted her skirt and played with her exposed clit, watching his dick feed into her tight little pussy.

"Oh, oh, yes, oh god, oh god, oh god, oh GOD!" She moaned, a bitch in heat overtaken by lust. She felt something building, and she worried for a second that she had to relieve herself. But George knew better and rubbed her clit faster with his thumb. He wanted to reach up and use his other hands to muffle her screams, but she was too far. Her pussy spasmed around him, her primal moans driving him over the edge, and he found his climax. He shot his hot cum deep inside her, her pussy pushed as far down on his cock as it could possibly go. She shuddered and shook on his lap, riding out the waves of her first orgasm.

Gladys was out of breath and leaned forward to lay against George, still sitting on his lap. Her heaving breasts were pressed into his suit jacket, and he placed his arms around her to hold her.

"Can we do this again, soon?" Gladys asked him.

"I'm sure they'll have another dance for the New Year," he replied.