Taking A Virgin's Cherry

by Tom Land

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Consensual, First, Oral Sex, Masturbation, Petting, Pregnancy, School, .

Desc: Sex Story: Tom becomes friends with a young woman who's been jilted by her fiance and in the process he finds himself the lucky recipient of this sexy young woman's determination to lose her virginity at her first opportunity. That opportunity only knocks once.

She wasn't your typical virgin since so many girls lose their pussy cherries sometime between 14 and 20 years old. But, Jessica was quite different from many young women and when Tom came in contact with her, she was in her early 20s and she was still very much a virgin.

Jessica had been saving her virginity for her wedding night. She'd been engaged to a guy who she thought would be her lover for the rest of her life. Then, when she found out that Ted, her fiancé, had been banging one of their mutual female friends, Jessica had quickly broken off the engagement and used some choice words to tell Ted what she thought of the way he'd treated her and cheated on her.

Ted's fuckup was Tom's gain because he'd met Jessica shortly before the summer during which her betrothal to Ted had occurred. Being Jessica's only serious male contact in the town where she was living, Tom found himself the almost immediate beneficiary of Jessica's newly "single" status. And he soon found out that wasn't the only thing he was to become the beneficiary of. With her hoped-for marriage to Ted dashed to the rocks of infidelity, Jessica determined to spite Ted and lose her virginity with the first horny hot man that gave her the slightest attention at all. That lucky guy would be Tom.

Jessica was a beauty and she had such innate beauty and sensuality that she certainly never realized what a sexy and very attractive woman she was. She didn't seem to focus on her natural beauty and her very sexy voluptuous body in any way. But any man who saw Jessica couldn't help but notice what a gorgeous and thoroughly hot woman she was. Jessica never realized those things about herself until Tom showed her the first time. And that first time was quite an eye-opening experience for her.

One thing Tom had noticed immediately about Jessica was that she was a big girl. No, she wasn't fat and she wasn't overly tall, but she was every bit of 6'7" or 8" and she had a big-boned body with an startlingly well-developed womanly figure. Jessica's breasts were at least D-cup in size and she'd always had rather markedly large breasts from puberty and yet Jessica had never allowed her early physical development to override any other parts of her figure or her own personality. Even though early on she'd had to learn how to buy the kinds of well-fitting bras that held her sexy tits nicely, Jessica just put that in the back of her mind as one aspect of her own physical being that her future husband would find attractive and give her his personal attentions. Now that Jessica had been disappointed in her engagement, she was slightly beginning to think of herself in somewhat more sexual and sensual ways, but still nowhere near as sexual as Tom thought of her whenever he saw her. Jessica took his breath away every single time he laid eyes on her, and he couldn't help but find himself fantasizing about her sexually frequently.

Tom had met Jessica in a public location but they'd immediately struck up a conversation and when he'd found out that she was new to the area and that she'd just recently broken up her engagement to her fiancé, Tom decided to strike while the opportunity to take advantage of Jessica's new availability was still prime. Tom was actually amazed at how quickly he was able to talk Jessica in going back to his place with him. He figured he'd have to make a date and all that but little did he realize that he was talking to a woman "on the brink" and she just wanted a man to show her that she was attractive and that she meant something to some man. Tom was more than happy to give Jessica just what she wanted. He got her over to his place quickly and then as they went inside the door, he moved over to Jessica and took her into his arms. Tom wasn't quite sure what sexual experience, if any, Jessica had and as soon as he wrapped his arms around this sexy young brunette, he began to realize that she was not only a virgin in the sexual sense but she was totally uninitiated in every sense of being with a man. As Tom moved to kiss Jessica, he could tell that she'd really never been kissed much at all before and he found that a huge turn-on, knowing that Jessica's sexual initiation and education were pretty much all left up to him. Tom closed his arms firmly around Jessica's mature womanly body and he allowed his left palm to slide down and cup the roundedness of Jessica's ass through her clothes while he pulled her closely against the hardness of his erection pushing out against her pussy mound.

It didn't take long at all before Tom and Jessica were both getting each other undressed. Tom was so horny to fuck Jessica that he could hardly wait and Jessica was fighting against the desire to preserve her virginity and the conflicting desire to actually have a man make love to her for the very first time. She wasn't really sure at that very moment that she'd go through letting Tom fuck her, but Jessica was certainly giving it very serious consideration as she realized they were probably about to pass a point of no return. And she also knew that once she did lose her virginity, there was no recovering that status either.

Tom quickly had Jessica's blouse unfastened and he quickly moved to get her skirt off her sexy body as well while she began undoing and removing his shirt and pants. Jessica found that she was rapidly becoming very horny and the closer she and this new man in her life got to actually consummating a relationship as lovers for the first time, the more Jessica found that she wanted just that to happen.

Tom quickly got himself totally undressed so when the moment came to mount Jessica and get his cock inside her, he wouldn't have to stop and take any more time doing something like pulling his briefs off or anything that might give her a moment's pause to change her mind. Tom knew Jessica was a virgin and he'd deflowered enough virgins to know that the moment of truth could sometimes backfire and when a guy was hot and horny, he could suddenly find his dick waving in the wind when he'd been planning to bury it inside the woman of his attentions. Tom didn't intend to force Jessica to fuck him, but he also didn't intend to give her even a single opportunity of backing out of their fuck together.

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Story tagged with:
Ma/Fa / Consensual / First / Oral Sex / Masturbation / Petting / Pregnancy / School /