Dollars and Desire
Copyright© 2025 by brabo1978
Chapter 2
Erotica Sex Story: Chapter 2 - 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
The next day, Ashley searched out Logan. When she did find him, he was talking to some of his friends.
“Hey, Logan,” Ashley said, walking over.
He looked at her, surprised. “Hey, what’s up, Ash?”
“Could I talk to you for a moment?”
The grins on his friends’ faces and their snickering whispers immediately turned into a series of catcalls and wolf whistles. Ashley had expected it and was at least partially successful in blocking them out. Luckily, Logan quickly agreed to talk with her separately. Ashley had to admit to herself that he genuinely seemed ashamed of his request three days ago. He was also one of the rare people in school who didn’t partake in making fun of her. If she was honest with herself, that was part of the reason why she felt comfortable enough to approach him with her proposal.
“Uhm, remember when you, like, wanted to ask me out a few days ago?” she started.
“I’m sorry, Ashley! You were totally right, I shouldn’t have asked you ... that,” Logan tried to apologize again.
“Ssh, it’s ok,” Ashley reassured him. “Just, you never said exactly what you wanted from me. Can you ... can you tell me?”
“Ashley, please, just forget about it, I’m sorry,...”
“Logan, don’t worry about it. I’m not mad anymore. I just need to hear you say it. Can you do that for me? Please?” she asked again. After all, if she was going to make her suggestion to him, she needed to be absolutely sure that’s what he had in mind in the first place. She didn’t feel a need to find out whether there was an 8th circle of hell.
“Well, uhm, Jake said you ... after your date he gave you a ... facial?” The last word was barely a whisper.
“It’s ok. I told you, I’m not mad anymore. This is an embarrassing question, but ... how much ... how much would you have spent on that date to ... let you do that?”
“I don’t know, 50 maybe?” Logan asnwered hesitantly, looking down at his shoes.
“I think that sounds ok.” Ashley hesitated for a moment, but then made up her mind. She had been arguing with herself enough about this last night. It was now or never.
“What would you think about it if instead of spending that 50 on a date ... you just give it to me and I’ll let you cum on my face?” she blurted out.
Logan’s eyes widened in surprise before he began to stammer. “Wait ... Seriously? ... You’re offering me...”
“Yes, I’m serious. Everyone in school is giving me shit anyway. But just to be clear, I’m only offering the facial, nothing else,” she added, wanting to make sure there were no misconceptions. Then, when he didn’t react, she prodded him. “So? What do you think?”
“I think that I might regret it forever if I say no. How did you want to do this?” Logan asked, still looking quite shocked at her proposal.
“Meet me at the men’s room on the first floor at 2.15. There shouldn’t be anyone there at that time,” Ashley said, trying to give him a seductive smile.
“I’ll be there!”
Logan sounded a lot more enthusiastic than she did, but that probably was to be expected. She wondered if he was nervous as well. She knew she was! Her nerves did have one advantage: though she was sure the sneers and glares of her classmates were most likely as bad as the past few days, they didn’t fully register this time. Besides, she’d better get used to it, because she sort of needed the reputation if she really wanted to make money out of doing this.
A little after 2pm, Ashley was walking through the hall on the first floor, noticing with some relief that it was indeed deserted. Arriving at the men’s room, she hesitated for a moment, but then quickly entered. To her relief, Logan was already there, waiting for her. When he saw her coming in, a big smile broke out on his face. She smiled back, nervous jitters still racking her body.
“Hey, Ash,” he beamed. Logan was clearly looking forward to this.
“Hi Logan,” she replied, unsure of what else to say. “Are you ... are you ready for this?”
Immediately she felt like that was a stupid question. Of course he was ready. Maybe she should have asked herself that question.
“Yes. How did you want to do this?” he answered, nodding eagerly.
“Uhm, do you have the money?”
Ashley was surprised at how difficult she found it to ask this. Somehow it felt like this part was even dirtier than what she was going to do for him. Luckily, Logan wasn’t giving her any difficulty about it.
“Oh yes, of course,” was all he said, as he reached into his pocket, fumbling as he tried to get out a few crumpled bills.
After a quick check that he had indeed handed her a total of 50 dollars, Ashley pocketed the money.
“Okay, well uhm...”
Ashley looked around. She had thought of asking the money first, but she hadn’t gone through the logistics of what she was going to do. She had to lower herself in front of him, obviously, but she didn’t feel comfortable with the idea of kneeling on a dirty bathroom floor.
“Would it be ok if I sit down on the toilet? Then you can ... you know ... do your thing?”
Logan nodded and Ashley walked over to one of the stalls, perching herself on the toilet seat. As Logan followed her, he was already unbuttoning his pants. She felt a bit nervous and excited as she watched him pulling down his jeans. His dick sprung free and bobbed in front of him, already hard in anticipation. It wasn’t that different from Jake’s, Ashley thought. Maybe a little larger, but she wasn’t sure.
It was a strange sight. This boy, that she only knew superficially, standing right in front of her with his dick out, throbbing and pointing at her, looking at her expectantly. Ashley took a deep breath and leaned forward, hesitantly taking his dick in her hand. Having a dick in her hand felt a little familiar after having jerked off Jake a few days before. Just like the feeling of excitement and awkwardness of pleasuring him felt familiar as well, though there was a different reason this time for the awkwardness and her nerves.
Logan’s moan, almost as soon as she took his dick in her hand, seemed to indicate he didn’t share her reservations. Probably for the best, maybe he’d become a returning customer. That is, if she had the courage to continue this activity. Ashley looked up into Logan’s eyes, trying to put some confidence in her smile. She saw him looking at her expectantly and began to slowly jerk him off.
She felt a little calmer as she listened to his soft moans and whimpers. His dick felt nice in her hand as she tried to remember how exactly Jake had adjusted her grip and motion on his dick. Maybe this wasn’t too bad. She did think it hot to touch a boy’s cock, and after all, she wasn’t giving herself up. She’d end up dirty, kind of, but that could be washed off.
“Does it feel good like this?” Ashley asked, looking up at Logan again.
“Yeah, it feels amazing,” and then, after a few seconds he added with a pleading face, “but it would be even better if you’d show your tits.”
Ashley jerked back, surprised. In hindsight it was stupid of her to not expect the request. Of course he would want to see her body and at the very least her boobs. But she didn’t feel comfortable with that. Jerking off a boy was one thing, exposing herself to him was a whole different thing.
“I’m sorry, Logan, but I’m just not comfortable with that,” Ashley finally responded shyly.
“Oh, come on. Please? I promise I won’t touch you. It would just add a nice visual to your handjob.”
“Look, I told you I’d do for you what I did for Jake. I didn’t show him my boobs. Now, do you still want to cum or are we calling it off?” Ashley asked, getting a little irritated.
“Of course I still want it, Ashley. I’m just saying, showing some skin would make it that much better for me,” Logan tried to coax her into it.
“Maybe this was a bad idea,” Ashley muttered, as she pushed him back and stood up.
“Okay, I’m sorry. I’ll just stick with the facial,” Logan caved.
Still a little miffed, Ashley sat back down. Content that her boundaries were clear and respected, she tried to get back to on the task. Logan’s cock had softened partially during their discussion, but it quickly responded to Ashley’s touch as she took it in her hand again. With a renewed sense of purpose, Ashley decided to focus on finishing him off. She took him a little firmer in her hand and quickened her pace.
“Oh yes, just like that,” Logan moaned.
Ashley continued to stroke his cock with increasing intensity, her eyes locked on his face, changing hands when she got tired. She could see the tension building in his body as his climax began to build inside him. His breath came in shorter gasps, his thigh muscles tightened, and his balls drew up. Ashley’s own heart started racing, knowing that the moment of truth was near.
“Yes, yes, don’t stop! I’m almost there!” Logan grunted.
A last minute moment of doubt flitted through Ashley’s mind. But before she even had a chance to react or change her grip, Logan’s cock twitched and his semen spurted out of it. Ashley barely had the time to realize what was happening before the first glob hit her cheek. A second one landed on her nose and lips, while a third one landed straight into her mouth. She could feel more semen running down her chin and onto her neck, staining her white blouse. Finally Logan took hold of her hand around his dick to slow her down.
“Wow! That is so hot!” Logan whispered excitedly, watching his cum dribble down her face.
Ashley just sat there, not knowing what to do. She wanted to get his cum off her face, but as long as he was studying the results of his handiwork, she felt she should let him. He had paid for it after all. Only when Logan began putting his dick away, did she stand up to check herself in the bathroom mirror.
It wasn’t too bad. Forcing herself to look at her reflection, Ashley felt confident she could do this again. She wiped her face with some paper towels and rinsed her mouth. Only when looking up again, she noticed the stains on her blouse. Fuck! This hadn’t happened the first time with Jake. Getting cum on her clothes was definitely not something she had factored in her little plan. She tried to wipe it off, but it was no use. Luckily school was over for today.
“Hey, Ash, uhm, thank you. And I promise I’ll keep my mouth shut about this,” Logan assured her as he was ready to leave.
“Actually, uhm, you don’t have to keep it for yourself ... I was kinda hoping you ... you’d advertise a little?” Ashley asked, trying to sound more confident than she felt about her request.
Logan was clearly taken aback by her request. He just mumbled something along the lines of “oh, uh, sure,” before he left the bathroom. Ashley couldn’t blame him for being surprised. It was a strange request after all. But getting more customers was the whole point of this little enterprise.
Ashley looked at her reflection in the bathroom mirror again, mostly thinking about the cum on her blouse. She realized that this would happen again if she continued in this line of business. This time she was lucky that school was already over, so she could head straight home. Getting stains on her clothes once could happen, but she didn’t want to explain to her mom why she suddenly started getting her clothes stained all the time.
Two days passed uneventfully. Somehow people still found it amusing to give her shit about what happened with Jake. But no one propositioned her. Was no one interested? Did Logan not tell anyone? Maybe he was too embarrassed about paying for it? Should she just come out and make the same offer to another classmate? She wasn’t too sure she could do that. Maybe she just had to keep it to a one time $50 extra spending money. The problem was that she really could use the money.
Just then, Matt came up to her, looking around to check that no one was watching them. He had been one of the worst guys to tease her in the beginning, but these last few days he had more or less ignored her. Ashley steeled herself for whatever taunt had taken him so long to find.
“Hey, Ashley, uhm, do you have a moment?”
That was unusually polite coming from him, Ashley thought.
“Is it true that Logan paid you to cum on your face?”
Logan had told about it! Her business wasn’t dead from the start!
When she didn’t immediately respond, Matt hastily added, “I’m not asking to make fun of you. I was wondering if ... Logan said you’d accept ... Would you let me do it too?”
Ashley loved how this guy, usually so confident about himself, was now having trouble finding the words to tell her what he wanted.
“Sure, why not?” she smiled at him. They quickly arranged to meet at lunch break behind a shed at the edge of the school property, and went their separate ways.
As lunchtime rolled around, Ashley made her way over to the arranged spot. No one was there, good. Less than a minute later, Matt’s head peeked around the corner before he joined her. Ashley looked at him and observed how he tried to mask his nerves with his smile. She actually liked it. It felt comfortable to have the upper hand, to be the one in control.
“Do you have the money?” Ashley asked bluntly, her directness softened with a sweet smile and a hand resting gently on his chest.
“Uh, yes, of course,” Matt stammered slightly, hastily pulling out a wad of cash and counting out fifty dollars before he offered them up to Ashley. As she accepted the money, Ashley noticed he seemed to have plenty more with him. That encouraged her to make her next suggestion.
“You know ... for an extra twenty bucks, you can see my boobs while we do this,” she offered casually.
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