tagFirst TimeJailbait

Jailbait

byKaishaku©

Jailbait. Harry had to smile at the term. To think that the voluptuous woman sitting in the car next to him would have been considered a child just yesterday, that suddenly, with the passing of a single day, she somehow gained the judgment, wisdom and maturity to be considered an adult. Forget the fact that she was considered too young to drink or smoke, she was, in the eyes of the law, old enough... old enough to enjoy the comfort of a man, a man like Harry.

Harry was patient, why even today he calmly waited in his car parked just outside the school grounds like he had since the beginning of the school year... like he had since the beginning of each school year for the past several years. He had waited for cheerleading practice to end and for Jenny to gather her things, chat some with her friends, flirt with a few of the football players before walking over to Harry's car.

"Happy birthday," Harry had said with a proud smile as Jenny slipped into the leather seat beside him.

"Thanks, I need to get home early tonight -- my parents have a little something planned."

"Well, we better get going then, but not before..." He watched her eyes as he held up the small box to her.

"For me?" she smiled. Her smile grew larger as Harry opened the box. "Is it real?"

"Of course," he lied, "two whole carats. It took me a while to find a heart shaped one." He slipped the necklace out of the box and eased it up over her head. He held his breath as the sparkling stone nestled between her breasts.

"It's beautiful," he heard Jenny say.

"Not as beautiful as you," he whispered, leaning forward to grasp the stone, letting his fingers lightly rest against her flesh. He leaned forward, turned his head slightly and touched his lips to hers.

It wasn't their first kiss. No, in the past several weeks as Harry and Jenny worked together they had gone from the doting kiss on the forehead, to light pecks on the cheek to even the quick lip to lip kiss. But now it was different, Harry had no plans to leave it there. This kiss was only the beginning.

Harry kept his mouth on Jenny's as he opened his mouth just slightly letting his tongue taste her cherry flavored lip gloss. When she responded opening her lips slightly he pressed onward, letting his tongue enter her mouth and then lightly touch her tongue. His hand moved from the necklace sliding downward as he lightly cupped her breast.

"Instead of going back to the studio today, I want to take you somewhere special."

She smiled again, nodding in anticipation.

"I had planned a nice dinner, but since you have plans with your family we can go somewhere else."

"Okay," she replied.

Jenny wasn't stupid, nor was she the type of girl to simply fall into the grasp of an older man. No she was very smart and cautious, it's just that Harry was good, very good. He also looked considerably younger than he really was. Over the years, being surrounded by the beautiful young women in his agency, he maintained a style and technique that kept him successful, Successful in business and successful around women, especially young women.

The penthouse overlooked the beach and as Jenny stepped out onto the balcony he watched the sunlight play over her skin. The cubic zirconia sparkled nearly as much as her eyes. Harry walked up and stood beside her, handing her a glass.

"I know you are too young for this, but it's not every day you turn 18. Besides it's just champagne."

She took a quick sip, hiccupped from the fizz and then giggled. Harry watched her take another sip and then took her glass, placed it on a table and lightly touched her shoulders, turning her to him. Turning his head, he pulled her close to him and kissed her. His tongue slipped into her mouth and touched hers as he pulled her against him, feeling her breasts press to his chest.

He then broke away, took a deep breath and then said, "I guess you can feel it, I... I... it's just that you are so beautiful, so nice. I just can't help..." He pulled her to him again, this time letting his hands slide down and lightly cup her ass. He kissed her mouth, then her neck and then whispered, "You are so special to me."

Taking her hand, he walked her back inside and standing there, at the foot of the bed he whispered, "I want to see you, to see all of you wearing just the necklace." He let his voice quiver slightly as he finished the sentence.

He waited for a moment, wondering if perhaps Jenny might stop this, might say, "No." Harry watched as her brow furled slightly, as she lightly bit her lips and then as she reached up and gloriously began unbuttoning her blouse.

"Oh yes, you are so beautiful," he whispered, encouraging her as she removed her blouse, which Harry took, carefully folded and placed on a nearby chair. He watched her hands drop to her pants which she unbuttoned as she kicked off her shoes. Once again, as she stepped out of her pants, Harry neatly folded them and placed them on the chair.

Seeing her pause, standing there in her bra and panties, he stepped forward turned her toward the mirror and as he unfastened her bra he whispered, "Look there in the mirror. See how beautiful it is, how beautiful you look with it dangling between your breasts." He nestled up close behind her and cupped each breast as the bra fell to the floor.

Harry then turned her again, backing her up to the bed. Kneeling in front of her he gently slipped her panties down, gazing at the nicely groomed tuft of hair just above her delicate slit. Working the panties down to her feet, he leaned toward her lightly pushing her against the bed until she sat down. He slipped his hands between her knees and then opened them, moving his head forward as he began kissing the soft skin of her thighs.

He moved his hands up her thighs and then reached around and grabbed her ass, pulling her to the edge of the bed as he moved his kisses closer and closer to something that just yesterday was so forbidden, but now, with the passing of a single day was so easily accessible. He whispered silently, "Happy birthday," as he eased his tongue between her tight lips, slowly working it up and down. Slowly, the lips blossomed open and he pushed his tongue into her, tasting her, feeling the flood of wetness as she overcame her nervousness and gave into the sensation.

Plunging his tongue in and out of her, Harry glanced up seeing her breasts heave with each of her breaths, her face, eyes closed appearing and disappearing with each deep gasp. After savoring the taste of her, he worked upward, searching, finding the tiny nub. As his tongue pressed firmly onto her clit he heard her moan loudly.

His tongue circled her, teasing her as her hips rose and fell, her gasps and moans pleading to him, wanting more, just that much more. Opening his lips he sucked her clit in and lightly pinched it between his tongue and his lip, she then sucked it as his hands grasped her ass. He held her tight as she moved beneath him.

Finally, just as he sensed she was about to come, he plunged his finger into her, first just one, but as her pussy opened to him he worked as second into her. He heard her groan loudly as he pushed two fingers into her. Her body suddenly relaxed as her pussy began to twitch, squeezing his fingers again and again.

Harry couldn't bear it any more. He slid his fingers out of Jenny's still convulsing pussy, kicked his shoes off, pulled his pants and underwear down and leaned onto her, his cock finding her soaking wet opening and plunging inside. He wondered for a moment if she was a virgin, but realized it really didn't matter now, all that mattered was what he felt, the warm, wet softness that drew him into her body.

He eased his cock into her, not really worried about hurting her, or if this were her first time or even thinking about pleasing her. No he simply wanted to savor the sensation, the feeling of her as he let the thought play through his mind that he, he alone was there inside this young girl who so strangely, with the passing of a single day, was now a woman. The physical sensation was one thing, so tight, yet wet and soft, but it was more, so much more as his cock exploded with pleasure and his cum filled her.

Yesterday this would have been a crime. Today it was simply an act of pleasure between a middle aged many and a newly blossomed woman. Harry eased his cock out of Jenny's pussy and whispered to her, "You were incredible, so wonderful and so beautiful."

He noticed the tears running from her eyes back towards her ears. Sitting her up he asked, "Happy tears?"

"Oh yes, yes, it's just that I'd never done..." she replied pulling him tight against her.

"You were a virgin?"

She nodded, shrugging her shoulders.

"It's a bit surprising, I mean these days for someone to wait..."

"I was waiting for the right time... for the right man."

Harry paused a moment, then smiled, "You know Jenny, I have plans for you. Big plans."

"Really?"

"Yes of course," he replied, taking her head and guiding it to his lap. As her mouth closed warmly over his soft cock he continued, "Yes, big plans."

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