Dollars and Desire
Copyright© 2025 by brabo1978
Chapter 1
Erotica Sex Story: Chapter 1 - After a disastrous date that is ruining her reputation, Ashley decides to sell her face as a canvas for boys to come on.
Caution: This Erotica Sex Story contains strong sexual content, including mt/ft Teenagers Fiction Facial Masturbation
“Oh, come on. Please?” Jake pleaded.
She had his hand in a grip, preventing him from going any further. They had been kissing in his car and with some hesitation she had allowed him to touch her boobs over her top. But that was as far as she was willing to go. When Jake’s fingers started to wander down to the waistband of her pants, she had stopped him and his begging had started.
“I’m sorry, Jake. I can’t do that,” Ashley said, still gripping his hand.
He sighed and leaned back against the seat of the car. They had just come from a fancy dinner at one of the nicest restaurants in town, a place Ashley had never been before. Jake had made a point of paying for everything and Ashley had wondered about it. For a high school senior he seemed unusually generous. No one had ever lavished her with so much attention or money before, and she did feel flattered.
Ashley knew she was pretty, but her family wasn’t particularly well off and most people at school knew. Add to that her reputation of being a good girl and not putting out, she didn’t get a lot of attention from the boys, or anyone for that matter. Jake asking her for a date last week had been a surprise. He seemed to be every girl’s dream. He was popular, being a star athlete and a more than decent academic performer. He was handsome, charming and had a quick wit. And on top of that, he lived in a mansion and his parents had gifted him a RAV4 for his 16th birthday.
Naturally, when he asked her out, Ashley had been a little suspicious, but she also knew she couldn’t pass up the opportunity. He had been a complete gentleman on their first date and Ashley had really enjoyed herself. Jake had kissed her when he dropped her off at home, but otherwise he hadn’t tried anything. When he asked her out for a second date two days later, she didn’t hesitate. Now she was here, sitting in his nice car with his hand grasped in hers.
“Why not?” Jake tried to argue. “I thought you were having fun.”
She sighed. “I did have fun. But I don’t want to rush things. I’m not that kind of girl.”
“You know I really like you, Ash. I wouldn’t be asking if I didn’t,” Jake said, giving her a hopeful look.
“I know you do, Jake. But I’m just not ready for that. I’m sorry,” she said, giving his hand a gentle squeeze.
“Would you at least help me out? Just kissing you has made me so worked up. You can’t let me go home like this,” he protested as he took her other hand and placed it on his crotch.
Ashley gulped, she could feel his hardness underneath her hand. It was the first time she ever felt a boy’s dick and she had to admit to herself that it made her tingle with desire as well. She didn’t fight when Jake rubbed her hand over his erection, trying to explore him further.
“Can I take it out? Please? Just a handjob.”
She hesitated. She knew she should say no, but the urge to see him, to please him, was strong. If she could avoid disappointing him this way, keeping the possibility of more dates and maybe even a relationship open, would it really be that terrible? A decision was made. She let go of his other hand to unbutton his pants for him. If she was going to do this, she might as well show some initiative herself. Show that she was on board, that she was willing to please him, that if he respected her she would eventually be his.
Ashley unbuttoned his jeans and slid down the zipper. His erect cock strained against his grey boxer briefs. She looked up at him to see him smile and give her an encouraging nod. Slowly she pulled down his briefs, freeing his dick, Jake helping her by lifting his ass. With both his pants and his briefs at his knees, Ashley got her first look at a man’s cock, a real one. It wasn’t as overly large as the one she had seen once in a porno, but that was probably a good thing: even though Ashley had no intention on having sex with Jake right now, she sure wanted to give herself to him at some point. It was smooth and veiny, crowned by a plump and shiny pink head.
“Go ahead, touch it, baby,” Jake encouraged her.
Gingerly, Ashley wrapped her hand around it, surprising by how warm it was or how it was soft and hard simultaneously. Fascinated, she watched her hand move up and down the length of his erect member. When she sped up too much, Jake put his hand over hers to show her she could put a lot more pressure on his cock and what speed to use. She caught on quickly, and Jake’s head fell back against the headrest. His dick throbbed in her hand and she couldn’t deny she liked having his dick in her hand. There was no way she’d tell Jake, but she was actually getting wet doing this. He was groaning and making small noises of pleasure.
“Your hand feels so good on my dick,” Jake panted out.
Lost in the moment, she got more into it, putting almost all her energy into pleasuring him. Spurred by his approval, she varied her pressure and grip slightly, going from loose to tight around him, twisting her hand and jerking him roughly at different moments. Jake couldn’t hold back anymore.
“I’m gonna cum, baby ... I’m gonna ... fuck!” he grunted and pulled her hand off his dick.
Before Ashley could ask what was wrong or why he had stopped her, Jake grabbed her by her hair, pulling her closer. She looked into his eyes and saw them burning with a strange intensity. With his other hand, he fisted his cock and started pumping it so vigorously his hand was only a blur. Just a few seconds later Ashley watched in horror how a thick stream of cum spurted out towards her face. She fought to get out of the way, but Jake was too strong for her and before she knew it the first spurt had landed on her cheek.