Dollars and Desire
Copyright© 2025 by brabo1978
Chapter 7: The Party
Erotica Sex Story: Chapter 7: The Party - 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 Ma/ft Mult Teenagers Coercion Consensual NonConsensual Fiction Brother Sister Exhibitionism First Facial Masturbation Petting
Laying on her bed, Ashley tried to get her meeting with the principal out of her head. It had been a few hours since she had left his office, ashamed and disgusted. She had taken a shower, trying to wash away the feeling of his hands on her, his ... him inside her, even the memories of what had happened. But it was no use. A few hours later, she was still reliving the encounter, over and over again.
Even more than when she was still in his office, Ashley was determined that it was over. The flow of clients had slowed to a trickle anyway, and it just wasn’t worth it. Despite the financial consequences, she felt good about her decision. It was about the only thing she was feeling good about right now.
The next day in school, Ashley kept her head down. Avoiding eye contact with anyone, she actively tried to blend in with the background. She felt like everybody was watching her, judging her. She admonished herself for being paranoid. No one except she and Principal Smith knew what she had done the day before. No one was watching her. Several were judging her, mostly girls, but that had nothing to do with the most recent events. That was something she was used to by now.
Of course, as seems to happen all the time, right when she had decided to quit her business, that’s when a new request came from one of her classmates. More than one even. Her mind made up firmly, she turned them all down. She felt sorry for them, seeing their disappointment, but she didn’t waver.
Until school got out, she tried to concentrate on her classes. For once she was actually glad she didn’t have many friends at school. She really doubted she’d be able to talk and banter with them as if nothing had happened. Without anyone questioning her behavior, she could keep to herself. There were of course questions from the boys she turned down, but those were easily deflected.
A few days went by like this. Things were almost back to normal, to before she started her side job. She did get a little more looks than before, but all in all, no one suspected anything was amiss. Again, the advantage of not having many people who really care enough to look closely. That weekend though, her resolve faced a more serious test.
Ashley was sitting on her bed, doing her homework, when Chris came knocking on her door.
“Hey, sis, can I come in?”
Her pen stopped writing mid-sentence, her mind flashing back to their last encounter. She had managed to avoid being alone with him after that moment, but apparently that lucky streak had ended now. The door opened slightly and Chris stuck his head in.
“Ash?”
“What is it?” She realized she sounded annoyed, but she thought he deserved that.
“Look, I’m sorry about, you know...” Chris trailed off.
So he was able to force her into letting him cum on her face, but now he couldn’t even say out loud what he was sorry about? The blackmail? The incestuous facial, or rather facials? The bukkake party she endured for his sake? What a man he was. Ashley didn’t know if she could, or should forgive him, but she did realize he would remain her brother forever. And at least he had the good grace to feel remorse.
“Thank you,” she replied curtly after a few seconds.
The relief on his face was clear when he entered the room. Ashley was a little surprised. She thought he’d leave after she accepted his apology, but Chris lingered in the room, looking uncomfortable. Looking at him, she waited, curious what was making him so nervous.
“I ... I’ve got something to ask you, Ash.”
Ashley raised an eyebrow.
He hesitated, rubbing the back of his neck. “Okay, I know this is a weird question, but ... it’s about your, uh, job.”
Ashley felt a shiver run down her spine. “Chris, we’re not going to do that again, okay? I ... I just can’t.”
Chris held up his hands in a placating gesture. “No, no, not like that. I just...”
He trailed off, and started over after a few seconds. “You know I’m Josh’s best man, right?” He looked at Ashley, but not seeing any reaction, he continued. “Which means I’m in charge of his bachelor party next weekend. And yesterday, some of the guys were asking about the strippers.”
Ashley could feel her cheeks turning slightly red, not liking where this was going.
“I never thought Josh would want something like that, but everyone assured me that it was essential for a good bachelor party. Only, I can’t seem to find any who are willing and available at this short notice.”
“No! Don’t even think of asking me,” Ashley interrupted him.
“There’s 20 guys and they’re all willing to put up $100,” Chris continued regardless.
It did startle her. Two thousand dollars for one night? That was a whole lot of money. She still wanted to say no, but the bait was really tempting her.
“I don’t know, Chris. I’ll have to think about it,” she replied after a while.
“Actually, there’s one more thing. I think the guys wouldn’t be very happy if they paid that much money for just one girl.”
“Oh, so first you try to reel me in with $2000, and now you’re telling me I’d only get who knows what part of that?”
Only after her outburst, did Ashley realize that her words made it clear that she was going to accept it, at least for the original number he had quoted.
“Uhm, I was actually hoping that maybe you had a friend who, you know...” Chris trailed off.
“No! I’m not gonna ask a friend to do this! Get out!” she snapped.
But in the end, that was kind of what she turned out doing. That Monday she vented to Riley about her own brother wanting to pimp her out. To her surprise, Riley didn’t commiserate or laugh at the idea though. The combination of the high reward for one night work and no one of her friends or anyone at school knowing about it, definitely triggered her interest.
When Riley texted her that night to confirm that she was in, Ashley in turn texted Chris one simple word. “Ok”
“Thank you thank you thank you” Chris sent her back.
At least for once he was smart enough to understand without making her explain what she meant, Ashley thought. She also realized she wasn’t as mad at him anymore. She hadn’t forgiven him for forcing himself on her yet, but despite his offer that made his apology seem opportunistic, his remorse had sounded genuine. She was still planning on quitting, the bachelor party would just be an exception. She did realize though that, just as her brother’s offer had sucked her back in, there was no guarantee she’d resist any more offers after that.
On Friday night, Chris drove Riley and Ashley to the venue he had rented for the evening. It was an old warehouse on the outskirts of town, transformed into a party space with a music installation and a bar. He dropped them off at a side door, where the base thump of the music was softly audible outside. Entering a small storage room, they started to take off their clothes, as they had discussed with Chris earlier.
Now naked except for some little black panties, they looked at each other and blushed. They had known each other since elementary school, but this was the first time they saw each other almost naked. For the first time, Ashley noticed that Riley’s breasts were somewhat bigger than hers. And while they didn’t sag, they definitely had more jiggle in them whenever Riley moved around. And though their areolas seemed to be about the same size, proportionate to their breasts, Riley’s nipples were definitely larger than her own pointy nubs. They were also slightly darker in color than the light pink she was used to.
“I can’t believe we’re about to do this,” Riley whispered in disbelief, as she looked up and down her friend as well.
Before Ashley could answer, the music stopped. Through the door to the main space, they heard Chris’s voice as he announced their arrival.
“I hope you’re all having fun yet. Now, because in a few days our dear Josh will have to make do with only one woman for the rest of his life, we’ve arranged for some special waitresses tonight. I’m sure everyone will love their ... outfits. Because it’s such a special occasion, they even told me that you’re free to feel them up as far as they are showing skin. Oh, and if you can’t stand it anymore, you don’t even have to look for a bathroom to relieve the pressure. For a small tip, they’ll be more than happy to receive your precious gift anywhere on their body! I’m sure that doesn’t count as cheating, right Josh?”
Fucking Chris! They hadn’t talked about getting groped by twenty drunk and horny men. But it was too late to back out now, was it? Besides, she did like the sound of “a small tip”. Nor would it do them any good to come out and set the record straight in front of his audience. There was not a chance that those guys would accept her “no” after Chris had already promised them free access. At least Riley didn’t seem too upset about it. She probably didn’t even realize that groping had never been part of the deal in Ashley’s earlier encounters.
“Ashley, Riley, come and say hi to Josh! Show him what he will be missing out on from now on.”
Time to face the music, Ashley told herself. She exchanged a glance with Riley, who nodded, at the same time nervously and determinedly. Opening the door, they stepped into the main room under the appreciative whistles and catcalls of the twenty or so men gathered there. The music started up again as they were led towards the groom-to-be. Several hands reached out to smack their asses or get in a quick squeeze of their breasts as they made their way through the crowd. Finally standing in front of Josh and Chris, Chris introduced them both to the man of the hour.
“So, Josh, this is Ashley, and this is Riley, our waitresses and entertainment for tonight. They are very excited to meet you.”
As if, Ashley thought, while smiling at Josh. Not that he was bad looking, on the contrary, but the fact that she was standing almost naked in front of a fully dressed guy had more to do with the money than with any real excitement on her part. She noticed though that Riley was playing up the infatuated school girl part with a high pitched “Hi, Josh” as she twirled her hair and fluttered her eyes at him.
“Come on, Josh, that’s no way to greet a pretty girl who is offering herself up this way,” Chris teased him.
A little hesitant, Josh stepped closer and kissed Riley on the cheeks. As he did, Chris took his hand and placed it squarely on one of Riley’s breasts. Instinct took over almost immediately as Josh’s hand cupped her breast and kneeded it, his eyes alternating on her breasts and her eyes. Riley gasped at the intimate contact, but then giggled as Josh continued to fondle her. Looking into his eyes, she even leaned into his hand.
“Hey, aren’t you forgetting about Ashley here?” Chris then asked. Ashley was a little shocked that her own brother would encourage him to feel up his sister like that. Then again, was this really so unexpected after he had made Josh grab Riley’s boob or after asking her to do this job in the first place?
Sure enough, with much less hesitation this time, Josh moved over to Ashley and placed a hand on her breast, even before he leaned in to give her a chaste kiss on the cheek. She had to admit that he knew how to handle a breast, while smiling shyly at him. Only when Chris spoke up once more, did he let go.
“Still sure you want to get married, bro, and miss out on fine women like these?” he taunted him.
“They are hot, I give you that, but you know I love Lisa. I’ll stick with her,” Josh replied with a chuckle.
“Alright, just making sure.” Then, addressing Ashley and Riley, “Okay, girls, time for you to get to work. There’s plenty of thirsty guests to serve.”
And so, Riley and Ashley started the work they had been hired for, serving drinks and refilling them for the guests. Given the free pass, most of them took the liberty to touch or grope them while receiving their drinks. After a while, following Riley’s lead who seemed surprisingly comfortable, maybe even enjoying herself, Ashley started to play along with the guests. She began flirting with the gropers, giving them innocent touches here and there, encouraging them to touch her even more.
Obviously, she had to fight the guests at the same time as they continuously tried to reset the boundaries. She tried to be playful about it every time she admonished one of them for putting his hand on her panties, cupping her pussy, every time one of them tried to dry hump her. Then she noticed how Riley accepted some cash from one of the guests after which he slid his hand into her panties without her making any effort to stop him. Realizing Riley was making this a losing battle, the next time someone grabbed her ass to push her against his obvious erection, she didn’t fend him off.
“You know, that’s extra,” was all she commented.
“Oh, uh, ok.”
He quickly grabbed a twenty and offered it to her. After tucking it away in her panties, Ashley now wrapped her arms around him as he began to grind into her and even allowed him to kiss her. After a minute or so, she excused herself by pointing out there were more guests she had to attend to. Sure enough, a few onlookers had gathered, watching her press her body against their friend, waiting their turn. But before she could even accept the extra tip from the second guy, someone across the room yelled “belly shots!”
Clearly there were plenty of college age guys here, Ashley thought, but considering what she was already doing, she didn’t feel the need to object. Riley seemed even enthusiastic about it and was already working out the logistics.
“Ok, I’ll lay down on the table like this. You can pour a little tequila in my belly button, put a lemon wedge between my boobs and some salt on my nipple. You lick the salt, take the shot, then suck the lemon, so it’s nipple, belly button, tits. Come on, Ash, come lay down next to me,” she eagerly rambled off.
Just go with the flow, Ashley told herself while laying down next to Riley. Soon enough someone was eagerly pouring tequila into her belly button and carefully placing a lemon wedge and some salt on her breasts.
“I think Josh and his best man should start this off,” one of the onlookers suggested.
A lot of the other guys agreed and Chris and Josh came forward. Ashley got pretty nervous, but luckily, Josh came to stand next to her, so her brother positioned himself next to Riley. Before she could dwell on the possibility of her brother touching and tasting her body, Josh had leaned over and started licking the salt from her nipple. A shiver ran down her spine as his tongue made contact with her sensitive flesh. As she expected, Josh took his time, first licking around her nipple, before taking it into his mouth and sucking gently. His lips never quiet lost contact with her skin as he traveled to her belly button. It was a bit of a ticklish experience to have him suck the tequila from there, but she managed to stifle her giggle. Moving back up, Josh placed his hands on the outside of her breasts and pushed them together, claiming with a smile that it would make it easier for him to take the lemon wedge. He grabbed it with his teeth and sucked on it for a while, his hands still holding her breasts together. Finally, he let go.
“Next,” he announced with a broad smile.
A renewed chorus of hoots and cheers erupted from the crowd as Josh stepped back and the next volunteer came forward. Looking next to her as her body was prepped for the next belly shot, she watched Chris being replaced by another guy as well. Her attention was drawn back to her own body as the next participant began licking her nipple. Several guys came and went, and Ashley found that she did actually enjoy them. The hardest moment came when one of the guys had finished taking his shot from her and was replaced by Chris.
“What are you doing?” she hissed softly at him.
“The other guys don’t know you’re my sister, we need to keep up the pretense. Or do you want them to start asking why I don’t want to touch you?”
Ashley sighed annoyedly, but she couldn’t argue with his point and allowed him to take his turn. Knowing her brother was licking her nipple felt weird, but the sensation itself was just as nice as with the other guys. In order to keep her composure, she closed her eyes and tried to ban any thoughts about who was doing it to her, instead concentrating on the pleasurable sensations. Fuck! Why did it have to be pleasurable? She wasn’t supposed to like this. She got a moment of respite when he slurped the tequila from her belly button, but all too soon he was back at her boobs, touching them, holding them, and then taking the lemon wedge from between them. Chris seemed to take more time than the others doing so, but finally let go of her boobs and Ashley could try to forget this weird experience.