Jamie Avery had always been boy crazy. Her latest boyfriend was Jeff, a college Sophomore whom her parents didn't approve of, mostly because he was older than her. That only made him that much more appealing to the little 18 year old brunette. And so, one May evening, after leaving cheerleading practice with a feigned stomach ache, Jamie found herself in the front seat of Jeff's car, making out.
Jeff was a total novice, and a virgin at nineteen. The girls his age and older found him to be kind of tall and dorky with his rusty red hair and freckles. It was only lately, since he decided to expand his horizons to some of the younger girls, that he had begun to gain some self-confidence. Before he started dating Jamie, he had only been able to convince the girls to let him feel their breasts through their clothes. With Jamie, he got even further. After only a couple of dates, she already had let him reach under her blouse and play with one of her small but perky nipples inside her clasped bra.
This afternoon they sat as close together as the bucket seats would allow, their lips locked together in an unending, steamy kiss while Jeff awkwardly fumbled around again inside of her bra. Jamie was gasping as he tweaked her nipple, her face flush and her pussy wet. Jeff was hard as a rock to the point of being painful when he suddenly got an idea. He gently coaxed the arm she had wrapped around him off of his neck, his body-language indicating that his neck was stiff from being cocked in the same position for such an extended period of time. In truth, he was just using that as an excuse to get her to place her hand on his thigh, a mere five inches from the tip of his hardon.
Jeff returned to squeezing her boob, his efforts doubled to catch up for the momentary break. On the next gentle grope of her swelling boob, Jamie instinctively squeezed his thigh in response. Jeff squirmed, straining to move his cock closer to her hand, and succeeded at closing the gap in half. His next squeeze brought forth another from her that was almost painful to the boy. He reached down to grab her wrist and remove her clawing grip for a moment, or at least that's what Jamie assumed at that moment. Without removing his lips from the overheated girl, he placed her hand back squarely on top of his raging hardon.
Jamie was not aware of the difference until the next squeeze of his hand on her boob triggered hers on his cock. Suddenly, she felt the steel-like pole in his pants in the palm of her hand. Surprised, she pulled her hand away, even as Jeff's lips remained locked on hers. Jeff acted quickly and grabbed her hand, placing it back where it had been.
Even though Jamie was surprised at first, she really didn't mind, as long as Jeff continued to kiss her and play with her boobs. Quickly, she got used to it and loved the hot feel of his "Thing", as she still called it. She also loved how it made Jeff squirm back and forth. Soon, she was helping him, moving her hand back and forth along with him. She heard his breathing get faster and more uncontrolled and responded by stroking him faster. A few moments later, she heard him wheezing and knew he was enjoying the feel of her hand. Then, she heard him gasp and felt his hips lock up.
Jeff unexpectantly found himself cumming in his pants as Jamie continued to squeeze his dick. His underwear was soaked with his cum, and it quickly seeped through to stain the ouside of his dark pants. A moment later, he reached down to remove her wrist from his pants, stopping the kiss and flopping back in his seat in exhaustion.
"Oh my god, Girl. That was freakin' amazing!" he said.
"What was amazing?" she asked, naively.
"That!" he said, pointing to his crotch. "What you just did."
Squinting her eyes in the faint light, she could make out the growing stain in his pants. Shocked, she said, "Did you just cum?"
"Yeah," he gasped, nodding his head.
"Ewwww!" she said. "Gross!"
"No, it's not gross. In fact, it was great," he corrected.
"Really???" she asked, not convinced she'd done anything that was all that remarkable.
"Oh my god, it was fantastic. I loved playing with your boobs and feeling your hand on my dick. It was the greatest thing in the world!"
Jeff's praise seemed extreme to Jamie but she only cocked her head in amazement. She didn't know what to think but, since he was so happy, she guessed she should feel, well, proud.
Softening, she said, "Well, if you say so." After checking the car radio clock, she said, "Oh my god, look at the time. You'd better take me home."
Jeff agreed. "Yeah, I need to get home too. I'm going to have to clean up and put this stuff in the wash right away. We made a real mess," he laughed.
That night in bed, a still excited Jamie lay on her belly, struggling to sleep. Unable to resist, she stealthily reached her right hand under her belly, and pushed the fabric of her slight panties aside. Swishing her finger inside the gusset, she began to finger her clit, a guilty pleasure that was becoming increasingly common for the young girl in the past few weeks. As her diddling became more frantic, she buried her head in her pillow, biting her lower lip and stifling her moans.
A few times she reached her middle finger deep up inside her pussy, pressing firmly against the suffocatingly tight inner walls of her cunt. She remembered how, only a couple of years ago, she had been unable to get more than a fingertip up inside of her, but after a briefly painful accident while doing a split in cheerleading practice which resulted in the tearing of her hymen, she could now get her entire finger inside. And, of course, there was no longer any pain.
Tonight, though, she was in a hurry, after getting so worked up in the car. She removed her finger and resumed the external stroking of her clit, until her fingers gave her the orgasm she so badly needed. As she came, she imagined what Jeff's "Thing" actually looked like. It sure felt hot to her touch. As her ass shook in place, she wondered if she'd have the guts to find out.
CHAPTER TWO
She wouldn't have long to wait. A couple of days later, she had cheerleading practice after school again. She didn't feign sickness this time but did manage to tell her mom that practice would run a little later that evening.
Inside Jeff's car, she sat with her hands raised in front of her. "I just want to tell you, I only have a half an hour today, OK? It took some creative lying to get that much."
"Um, OK. I guess we'd better get going then," Jeff responded and, instantly, they were making out hot and heavy. It took only a minute or two of kissing before Jeff went for Jamie's breasts and only a few more before he got up the courage to unsnap her bra. Jamie had to help him, but moments later her B cups were released into the palms of his hands. The improved access felt awesome to Jeff, now that he could massage her entire breast. It also felt much better to Jamie than the cramped poking, pinching, and twisting they were subjected to last time. Within ten minutes, Jamie was already as hot and worked up as she been by the end of last time.
Jeff could sense she was ready for more and moved her hand down onto his crotch again. This time she did not flinch and immediately began to slide her hand over his hardon. Jeff loved it and kept on repeating, "Yeah, don't stop, Baby," as he continued to squeeze her boobs. Two minutes later, he was ready to cum and, somehow, managed to stop her hand from stroking him. Holding her wrist still, he croaked, "I... I don't wanna cum in my pants again. Last time, I nearly got into trouble with my mom. Please, we gotta stop."
"But, we still have like ten minutes!" Jamie gasped, not wanting it to be over yet. In a way, she felt the night would be a failure if she didn't make him cum.
"Well, maybe..." he said, summoning up his courage, "Maybe, if I took it out for a second, I could cum... um, oh I know, on my chest." He pulled his t-shirt off.