Dollars and Desire
Copyright© 2025 by brabo1978
Chapter 4: The First
Erotica Sex Story: Chapter 4: The First - 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 Coercion Consensual Fiction Brother Sister Facial Masturbation Petting
300 dollars. Three hundred. 3-0-0. Should she do it? Could she even do it? Like most girls she had dreamed of it being special. A special occasion, a special person and an expression of deep love between them. But maybe dreaming was a luxury, a luxury a girl in her position didn’t have. She had something a lot of boys wanted, he had something she needed. Desperately.
Especially now that business was slowing down. It was the one weakness in her “business plan”. Her customers were willing to pay for the novelty experience of cumming on a girl’s face, but once they finished, the novelty part of the experience was gone. She didn’t get many return customers. For a few weeks she had a booming business, but by now ... Let’s just say it was a good thing she didn’t have any operational costs or investments to pay off.
When she had started her business with Logan as her first customer, she would never have considered it. Not even for a second. Actually, even just a week ago there was no way she would have entertained the thought. But she hadn’t had a single customer for a whole week now. Michael had timed his offer perfectly, whether by design or by accident she didn’t know. But it was the first time Ashley felt tempted to cross the line she had drawn for herself. The line that allowed her not to think of herself as a prostitute.
$300 for her virginity. It was a lot of money. It was also a lot to ask. She had turned him down immediately, reflexively. But now she was wondering if maybe she should have at least considered it. She wasn’t in love with him, but at least he had been nice to her. If past events had taught her anything, it was that “nice” was already a lot. But was it enough?
It took her two more days to make up her mind, very aware that it was a bridge she could not uncross. But somewhere in the back of her mind, she knew. From the moment she began questioning her refusal, she knew she would give in. So it didn’t really come as a surprise that she found herself asking him to come talk with her, amidst knowing smiles from his friends. Or at least, they thought they knew.
“Does this mean you changed your mind?” Michael smiled hopefully at her.
“Maybe. Do your friends know about ... this?”
“I haven’t told them,” Michael said, his grin widening.
“Good. I feel it’s somehow different from just ... you know, the other stuff. I don’t think I want people to know ... I don’t want to be a prostitute!” Ashley blurted out in a hushed voice.
“Oh ... So ... you don’t want to...” Michael concluded, his previous smile gone now.
“I don’t know. I mean, I think I want to, but I’m not sure if I can. But only if you keep it to yourself,” she rambled, her face flushed with embarrassment.
“I promise,” Michael quickly assured her. Then, wanting to convince Ashley his promise would actually be worth something, he added, “I get that you don’t want people to know you’ll have sex for money. To be honest, this would also be my first time. And it wouldn’t do my rep any good if the boys knew I’d pay this much for it.”
Looking at his face, she could see his sincerity, or at least what she thought was his sincerity. Wanting to believe him, and at the same time looking for any excuse to refuse his offer for good, it took her a few seconds, but then she nodded.
“Okay,” was all she said. What more was there to say? Michael’s smile made it clear that he was perfectly happy with that one word.
Later that day, Ashley found herself on the porch of Michael’s house for the second time. She was a little nervous, but not as much as she had expected. Still, she wasn’t sure she could actually go through with it. She had decided to put her faith in Michael’s promise to accept a “no” if at any point she felt uncomfortable and wanted to stop. It was the main reason she had agreed to go through with this.
Mere seconds after she rang the doorbell, Michael opened the door. Thinking he may have been waiting by the door for her to arrive, made her smile. She was actually surprised how much his eagerness pleased her, made her forget the circumstances that could easily feel awkward, and instead even made her feel good about herself. Without hesitation, she followed him into the house and up the stairs to his room. Once again, the size of his room sparked a little bit of jealousy inside her, but she quickly managed to push that feeling away. Michael invited her to sit down next to him on the bed and she complied.
“So, uhm, what now?” Ashley asked, looking around his room as if she was waiting for a sign.
“I was thinking,” Michael began, his voice a little husky. “Maybe we could ... uhm, maybe you ... could kiss me first?”
Ashley looked at him in surprise. She hadn’t expected this. She had thought they would just get naked and get straight to it. But Michael looked sincere. Only then did she understand the impact of his admission earlier that day. He was a virgin as well. He wanted to have his first time, but he wanted it in the way he imagined it should be. The way a boyfriend and girlfriend would experience it.
She felt a pang of guilt for charging him and she had to remind herself that she wasn’t his girlfriend. Not really. But knowing this wouldn’t feel like a business transaction was going to help her go through with it. So she nodded. “Okay.”
Getting close, Michael reached a hand up to gently touch her cheek. Ashley felt a warmth spread through her at this gentle touch. His lips met hers and she savored the softness of his mouth. It was a simple kiss, just two pairs of lips touching. Then she found herself kissing him back. It was a soft kiss, gentle, sweet, and it felt ... nice. Before she knew it, she had parted her lips slightly, inviting him in. Michael took the cue and traced the outline of her lips with his tongue before slipping inside her mouth.
As they continued to explore each other’s mouth, Michael’s hand began to wander down her side. Then, ever so slowly, he moved it up again, cupping her breast through her t-shirt. As much as she had expected it to happen, it still came as a surprise, but not an unwelcome one. Unconsciously, or maybe not, she leaned into his touch, and their kiss became more passionate in response. Her hand landed on his chest, not to hold him back, but because she wanted to touch him. Wanted? Yes, she realized, she wanted this. At that point she knew she could go through with this.
She began pulling at his t-shirt, lifting it over his stomach, then his chest and his head. She wanted to feel his skin. And she wanted to encourage him to reciprocate, she wanted to feel his hands on her skin as well. When their lips separated and Michael looked at her, his question and her answer were unspoken. The look in his eyes communicated what he wanted, and Ashley nodded. A few seconds later, her t-shirt was on the floor, and her bra followed shortly after.
His look of admiration was as sincere and as profound as the first time he saw her boobs. But when he reached out this time, it wasn’t an act of pure lust from a boy who was completely absorbed by a fantasy of becoming a man. It was almost like a reverent touch, in awe of her body, of her. His fingers lightly traced the curve of her breasts, experienced the softness of her skin, the hardness of her nipples. Ashley could feel the goosebumps rising on her skin, her body responding to the gentleness of his caress.
This was nothing like her other transactions. This didn’t feel like a transaction at all. She may get paid to have sex, but it didn’t require much imagination to actually feel loved. And just like Michael gave her more than money, she wanted to give him more than just her body. She wanted him to feel cherished, special, as well. So she pulled him in closer, her breasts flattening against his chest, her hands wrapping around his back and kissed him again. Pressing herself against him, she could feel the hardness of his cock through his jeans. She reached down to his ass and pulled his lower body closer still, liking the feeling of his hardness rubbing against her stomach.
Clearly, so did Michael. Keeping one hand on her shoulder blade for stability, his other hand moved down to her ass, slipping under her pants to hold her flesh in his grip as he rubbed against her. Instinct was beginning to take over, but Ashley didn’t mind. His urges were now being met by hers, and she let herself be carried along. Their kiss had become hungry now, as if they were drowning and the only way to find air was through each other. Ashley welcomed it when Michael began fumbling at the button of her jeans and reciprocated by unbuttoning his jeans and lowering his zipper. The heat coming from his crotch felt like it was almost burning her hand. But that only encouraged her to slide her hand into his opened jeans and cup his cock through the fabric of his underwear. It twitched at her touch and Ashley discovered how intoxicating it was to have this much control over someone’s pleasure.
There was no hesitation on her part when Michael unzipped her jeans as well. When his hand slid inside her jeans and her panties, his fingers finding their way through the curly hairs to her already wet folds, stopping him didn’t even cross her mind. She gasped in his mouth when she felt a boy’s fingers probing her wetness, touching her clit for the first time. It felt incredible, so much different from anything she had ever done to herself. Automatically she tried to angle her pelvis to give him better access. Soon after, she felt his finger slipping inside her. Her mind was racing as his finger moved in and out of her slowly, exploring her inside. Fully focused on the new sensations, it took her a while to remember that she was supposed to bring him pleasure as well.
Her hand was still on his underwear, wrapped around his cock. Catching up to Michael, who had is hand on her bare pussy, his fingers even inside her, she lowered both his jeans and his underwear. His cock remained trapped by the fabric as she began pulling them down and she stopped for a moment to untangle it. Finally free, his cock sprang up, and Ashley appreciated the sight. Grasping him firmly, she began to stroke him. To her surprise his cock felt ... different. Somehow, knowing that this time it would go inside her, made it feel different than when she had given him a handjob the first time.
“Are you still okay?” Michael asked, his voice a hoarse whisper, his eyes watching her intently.
Ashley’s hand paused on his cock, but she realized that, yes, she was. Looking in his eyes, she nodded. “I’m ready.” She could feel her heart racing knowing what was going to happen next. She was nervous, but also excited. This was it. This was the time, the place, and most importantly, the boy she’d remember for the rest of her life. But she hadn’t lied to him. She was indeed ready.