Story 22
Summary:
Amy, a nineteen-year-old virgin. She’s going to a beach party with some friends to try and meet a guy and finally lose her virginity. But when she doesn’t meet anyone who interests her, she wanders off.
John, mid-thirties. He walks in on Amy in a staff room and makes a move.
Oral, titty sucking, jerk off, fingering, pussy licking, jerk off, blowjob.
It hadn’t been Amy’s idea to come to this party and she still wasn’t fully convinced that it had been a good idea.
Her friends had insisted that it was going to be the social event of the summer, and they had been so full of conviction that she had been forced to just go along with it.
She told herself that it would be good for her. Her friends often criticized her for not being sociable enough, and she knew that she had to put the effort in.
In her own group of friends, she could be outgoing, bubbly, and full of fun and laughter. But whenever there were too many people around she would find that she suddenly seemed to run out of things to say. She would become quiet, and introverted.
When she had been in high school and had seen her friends getting their first boyfriends and starting relationships, she had been somewhat jealous. That was the kind of thing that she wanted for herself - someone to be close to, someone to be intimate with. She just felt suddenly shy whenever a guy would show her any attention.
She was nineteen years old now and she had felt her frustrations grow and grow. Surely she should have had a proper boyfriend by now.
There had been a couple of guys who had stuck with it, put in more effort than others, and had managed to win her confidence. She had shared kisses with those guys and they had felt good - so good, so tantalizing, hinting at so much more to come.
But as soon as they had tried to move things forward and do something else, she had always pulled away from them. And then it would all fall apart - the confidence that she had been faking so far would suddenly leave her and she wouldn’t be able to carry on.
Whenever this happened she would see that the guys were dismayed by what had happened - they would ask what they had done wrong and she would shake her head, looking away. They were frustrated - of course, they were - and they would think that she was teasing them, leading them on. They would be annoyed with her.
“It’s fine,” they would tell her in a tone that would let her know that it really wasn’t fine at all.
She wished that she could have let things carry on just a little bit longer. She would feel her excitement growing and she was sure that if she could only have kept things going for just a little bit longer then she would have been able to fully give in to what they wanted - to what she thought that she wanted as well.
Her failures didn't stop other guys from trying their luck with her. At first, she didn't understand why they kept trying. She wasn't as outgoing and friendly with them as her friends were. She didn't flirt with them or laugh at their dumb jokes the way that her friends did.
She did know that people thought that she was attractive, anyway, and she did her best to make the most of her looks. She had pretty, delicate features and she had her black hair cut shoulder length and arranged so that it framed her face. Her eyes were big and dark green, her lips full and red which contrasted with her pale skin.
She was short but had a great figure. Her legs weren’t long but they were toned and looked good. She had a great figure with large breasts that seemed to be highlighted by her short frame.
She knew that she would keep getting chances to go further with guys, but she just didn’t know how to take advantage of those opportunities.
She sometimes had this idea that she should show some initiative. Maybe that was the problem - that she was too reactive rather than proactive. She waited for other people to make the first move and maybe she should be the one to make the first move.
She thought about what it would be like if she had a guy in her home. If it was just the two of them. If she knew that he wanted it - wanted her. She’d play it cool at first, acting as though she didn’t know just what it was that he wanted. She’d give him a guided tour of the house. She knew where it was that she was taking him, but she wanted to draw this out, build up the expectation.
Then they’d make it upstairs. When they reached her bedroom, she’d turn to look at him with a knowing look on her face as she pushed the door open. That would be when he’d know - when he’d realize that this time was going to be different, this time he was going to get everything that he wanted - and she was going to get everything that she had ever wanted as well.
When they were in her bedroom, she’d grab hold of him and kiss him. She imagined what it would feel like - the sense of power when she took control.
She thought about the shock on his face, the way that his body would tense before relaxing as he understood what was happening.
She’d push him up against the wall, kissing him, her hands pulling at his top, wanting to get him undressed. He’d pull at her clothes as well, peeling her tight top away from her body.
She thought about his hands on her breasts. That would be it - that would be the point when she would know that it was really happening, there was no turning back.
She’d push him down onto the bed and then she’d climb on top of him, straddling him. When she imagined this, she was wearing tiny, tiny, denim hot pants. They clung to her ass with just a hint of her ass cheeks pushing down beneath the edge of them.
When she thought about straddling him she thought about his hands on her thighs, the fingers digging in slightly. Then she’d look down at him with a little smile. She imagined the look of lust on his face.
Then she’d undo her bra and his lust would reach whole new levels as he buried his face between her bountiful breasts.
She thought about his hands and his mouth on her hot body.
She thought about taking hold of his body, then slipping her hands into his pants, feeling what he had down there. That was one mystery that she was desperate to see uncovered for her. She wanted to know what the big secret was, the thing that all of her friends seemed to find such pleasure in.
Sometimes when she was lying in bed alone at night she would wonder what it would feel like for a man to reach down into her pants as well. Her hand would go down there and she would begin to touch herself, imagining that it was a man doing it to her. She would sigh happily to herself as she continued touching herself.
But no matter how much she did it to herself, no matter how good it felt, she always knew that there was something else out there, waiting for her - something better. She wanted a man, needed a man. And so her frustration grew and grew.
Her friends had told her that this party was going to be the party to end all parties - the event of the summer. It was being held at a beach club in a town nearby. She had been there before and she knew the kind of place it was - lots of gorgeous people sunning themselves by the pool while the DJ played. It certainly seemed as though it could be a good time and it could be just the kind of place to meet a guy. At the same time, she did prefer smaller gatherings where it was just her and her friends. She knew that was no way to meet new people but at the same time, she liked staying in her comfort zone. She'd tell herself that it was called a comfort zone for a reason, after all - because it was comfortable. What was so wrong with being comfortable, really?
As she stood in her bedroom, her clothes scattered all over her bed as she tried to decide just what she was going to wear, she kept telling herself that she had to do it - she had to get out of her comfort zone. She told herself that she had to go to this party with a positive attitude and that was the only way that she was ever going to manage to get ahead.
She furrowed her brow as she looked at all the clothes on her bed. She was trying to choose something that was just right for the occasion. She had chosen a simple, black, bikini to wear under her outfit, just in case, she decided to sunbathe or go for a swim in one of the many pools at the beach club. The bikini was slightly too small and that was just how she liked it. It clung to her breasts with parts of them pushing out of the top and the bottom. When she had worn it before she had noticed guys desperately trying not to stare down at her breasts. As she was quite short they had to look down to talk to her anyway and her breasts were right there, right at the periphery of their vision. She wouldn't have minded if they had taken a good, hard, look at her breasts. She quite liked to have guys looking at her like that. It made her feel desirable and gave her a sense of power at the idea that they wanted her. A part of her thought that if only she could harness that power then there would be nothing that she couldn't do. If she could only hold onto that feeling then she wouldn't be too shy, too timid. She'd be able to take the things that she wanted.
With her bikini chosen, it was the rest of the outfit that drew her focus now. In the end, she chose a short, checked, skirt that stopped above her knees. She chose a simple black top - to match her bikini - that showed just a hint of her toned midriff and a hint of her breasts.
She put the outfit on and then checked herself out in the mirror. She pushed her breasts out and pouted at the mirror. She turned sideways to look at her ass. As she spun, quickly, her skirt went up and showed a flash of thigh. She lifted herself up to show more of her midriff.
She put her hands on her hips and looked at her reflection closely. She nodded to herself. Yes, she thought to herself, she did look pretty good.
She had a new sense of confidence. Maybe this really could be the day when she made things happen when she managed to move things to the next level.