Ashley’s Prostitution Ventures #03

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February 2005

Ashley Saunders, a pretty, eighteen-year-old high school senior with soft, full lips and expressive brown eyes, which she worried were too large for her face, twirled a strand of wavy brunette hair around her finger as she stared out the car window.

“You nervous, Ashy?” the driver asked her, drawing her gaze. “Is it because Darren is such an asshole?”

“Yeah, kinda,” she shrugged, and that was part of the truth. She was not sure she was ready to reveal the rest of what was on her mind to Corey.

Ashley and Corey had been friends in elementary school, but as middle school and high school had worked to separate them into different social groups, that friendship had dimmed. But now it was stronger than ever, and perhaps more than friendship. At the least, Ashley wanted it to be more, and she believed that Corey did too. There was just one problem. Over the last several weeks, Ashley had been accepting payment from some of her male classmates to take their virginity.

It had started with Corey. A rumor that she had engaged in sex for money with another classmate led Corey to approach her about losing his virginity. At first, she was offended, but then the possibilities of what Corey suggested intrigued her. It didn’t hurt that she had known him a long time and that he was a decent looking guy, especially for the nerdy group with whom he hung out. She went forward with the deal, and to her surprise, she and Corey clicked physically as well as rekindled their friendship. That also made a deal—he would help her find other guys who wanted to lose their virginity and help her to get to her ‘dates’, as she had no car of her own. In exchange for his help, she would continue her sexual relationship with him.

In the ensuing weeks, she went on four more dates, all with guys Corey knew, all of them virgins. And while she had been aroused enough for sex with those guys, none of them brought her to orgasm like Corey did. So, after each one, she and Corey parked someplace inconspicuous where he fingered her to a much-needed climax and she reciprocated by going down on him. She would have preferred sex, but he was not comfortable doing so after she had been with another guy. Besides, they had been getting together at his house after school as often as they could, and those times he had no problem having sex with her or making her climax. And it was the afternoons they spent together, talking and fooling around, that made her think maybe there was more than friendship there. Or would have been, if she were not a whore.

“If he is too bad, call me. I’ll stay close by.”

“Thanks, Cor,” she said, rubbing his arm and trying to not think about how much she wanted to tell him to find a secluded spot so she could give herself to him instead of going through with her date with Darren Connors.

It would also give her time to talk about Valentine’s day, the other issue on her mind. Her mother, who Ashley viewed as far too controlling, and who had been steadfast about her not having a serious boyfriend in high school, loved Corey. In fact, she had suggested to Ashley that she could stay out past her school night curfew—Ashley did not believe she should even have a curfew since she was eighteen—when Corey took her out for Valentine’s Day. The issue for Ashley was that since she and Corey were not really a couple in the way her parents and his parents believed, he had not asked her out. And that meant she would have to ask him, at least to keep up appearances.

“Or just kick him in the balls if he gets out of hand. He probably deserves it anyway.”

Ashley laughed, then looked back out the window, chewing on her bottom lip. Corey was right that Darren Connors was an asshole and no doubt deserved a kick to the nuts. He was a senior like they were, and he had turned eighteen in November, just like Ashley. But while Ashley was popular and Corey was well liked in his own group and at least respected outside of it, no one she knew liked Darren. He was an arrogant, spoiled, pudgy young man with a round face, small, dark eyes, and longish slick, black hair. He also claimed to have been sexually active with several girls in their class, but Ashley and most everyone else believed that the stories of his alleged conquests were lies. And she considered the fact that he had contacted Corey about her services as proof that those who doubted him had been right.

“Well, it is the next block over. You ready?”

“I guess,” the young brunette sighed. “I just hope he showered like I instructed in the email.”

After her fourth ‘date’, Corey had created an anonymous email account for her, and she had started sending instructions to her new clients. The top of the list was showering right before she was supposed to arrive. That was because the young man who was her fourth client was drenched with nervous sweat when she showed up, so she had made him take a shower before they did anything.

“You’ll be lucky if he did,” Corey grumbled. “That guy always looks like he needs one.”

“Thanks for the support, pal,” ankara türbanlı escort Ashley replied, managing a weak smile as she rolled her brown eyes.

“That’s what I’m here for,” he said as they pulled up to a good-sized two-story house with a large, green, well-kept front yard.

“I know,” she told him, her smile stronger. “Even if you were joking.”

Corey started to object, but she silenced him with a kiss.

“Call me if you need me!” he reminded her as she exited the car.

Ashley waved, then strolled up a decorative stone walkway to the front door. She did not look back as she heard Corey’s car pull away. She knew he would have preferred to wait until she was inside, but she did not like the idea of her clients seeing him do so.

Inhaling deeply, she rang the doorbell, wishing she had one last chance to check her makeup.

“Holy fuck! Ashley Saunders!” Darren said when he opened the door, his surprise obvious on his round face. It had been the same with all her clients after Corey.

“Yeppers. Can I come in?”

“Fuck yeah,” the plump young man in grey sweats and a loose, black t-shirt chortled. “This is fucking fantastic. I’ve been trying to figure out who you’d be since Corey set this up, but I have to say I never thought you’d be you.”

“Well, I’m me,” the brunette shrugged, noting the way Darren’s eyes had fixed onto her chest when she had taken off her dark gray coat.

As had been her practice on her previous dates, Ashley had dressed casually. For her date with Darren, she wore form-fitting jeans a blue so light it was bordering on white and a darker blue, button-up blouse. A pullover top would have been better for disrobing and dressing again afterward, but the button-up one allowed her to leave her house looking modest yet arrive at her date with enough buttons open to show off her cleavage. Her preference would have been to complete her look with calf-high boots, but her experience was that the low-top canvas sneakers she was wearing were much easier to take off.

“So, you got the email, I presume.”

“Um yeah.”

“And you’ve been told what to expect?”

“Uh huh. You’ll suck me off then I’ll fuck you.”

“Exactly,” Ashley nodded, although she had not phrased it like that in her email.

“Your first experience will include special oral attention to make sure you are relaxed and ready for the main event, with the stamina to make the most of your rite of passage into manhood,” was what she had written. Corey told her it was too flowery, but she did not want it obvious what she meant if an email made its way into the wrong hands. Yes, Corey assured her the address he made for her would be anonymous and more difficult to trace for anyone who wasn’t a hacker or IT professional, but she was still nervous.

“So, what’re you standing there for. Strip.”

“Wouldn’t you rather go to your bedroom?”


“So, you want to, um, do it here, in your entry hall?”


“Then what do you want?” Ashley asked, trying to keep her mounting irritation out of her voice.

This part—when the guy had no idea what to do next—was her least favorite part of the whole thing. After she had been too direct with a young man named Grant, her first client after Corey, she had worked on helping her clients relax, taking them to their bedrooms after receiving her payment, then moving slowly enough to put them at ease, or at least at as much ease as possible. It was torture for her, as she would have like to have proceeded quicker, but it was what they needed. That was obviously not true with Darren, however.

“I told you to strip. Then you can follow me.”

“Look, I hate to do it this way, but I’m going to need the money first.”

“What if I decide I don’t think it’s worth a hundred bucks? That’s why I told you to strip.”

“I can just leave,” the brunette snapped, her eyes fixed on Darren’s small, dark orbs.

“Yeah, but you’d be out a hundred bucks.”

“And you’d still be a virgin.”

“Who the fuck said I was a virgin? I get lots of trim.”

“Then the price triples. The hundred bucks is a virgin special.”

“Shit, I’m not paying three bills to fuck you,”

“Then I’m gone,” Ashley said, turning toward the door.

“Wait. I’ll get the hundred.”

“Three hundred.”

“Okay. Okay. I’m a virgin. Happy?”

“I will be when I get…”

“I’m fucking getting your money, whore,” the thick young man spat, a scowl twisting his round face into a mask of anger.

“Thank you,” she called after him as he headed up the stairs.

Get the fuck out of here, a voice in her head suggested, but Ashely shoved that thought into the back of her mind, along with her anger at being called a ‘whore’. Darren was a loudmouthed asshole, but she suspected he was all bluster. After all, he had quickly backed down on his claim that he was not a virgin.

“Here’s your hundred,” the pudgy young man sneered, as he took a hundred from ankara ukraynalı escort a money clip, the first she had ever seen someone her own age carry. It was also not lost on her that she had seen at least two more hundreds in the stack of money in the clip.

“Thank you, Darren,” Ashley smiled, taking the money and putting it in her purse, which she set near the door in case she might need to grab it in a hurry on her way out the door. “So, you ready to go to your bedroom now?”

“I already said no to that, bitch,” he snarled. “Strip.”

“Don’t call me a bitch, Darren.”

“Why the fuck not? I paid you, didn’t I?”

“Yes, you paid me. But I’m not here to get abused by you.”

“Whatever helps you sleep at night.”

Kick him in the balls, Corey’s voice interjected, and that made Ashley smile. It also helped her relax enough to decide it was better to go along in order to get it all over with. And the sooner she was done with Darren, the sooner she would be back with Corey.

“What about my coat?” she asked, holding it out. “Where can I put it?”

“On the floor, I guess. What the fuck do I care? Now quit stalling and stip.”

Ashley made herself count to ten while she kicked off her shoes, placing them by her purse. She then folded her coat and laid it on top of her shoes. She did not look at Darren while she did so, but she could feel his eyes on her.

“Am I ever gonna see those tits?”

“Sure, big boy,” the eighteen-year-old brunette purred, standing and turning to face him.

Forcing a smile onto her face, Ashley trailed her dark red nails across her exposed cleavage before undoing the first button, at least the first that was fastened. The top three had been undone before she walked in the door.

“Fuck this slow, wannabe seductive bullshit. Just get your clothes off and show me what I’m getting.”

“You’re the client,” Ashley said, stopping herself from rolling her eyes as she finished unbuttoning her top.

“Fuck yeah I am. Now show me those tits.”

Ashley paused, blouse in her hand. She had intended to take off her jeans next, but clearly, Darren wanted a different order. Still, she folded her top and put it on top of her coat.

“Fucking today, whore,” her plump client snarled.

“I don’t want my clothes to get all messed up.”

“I don’t give a shit what you want. Take that fucking bra off and show me your tits. Not even sure why you wore the fucking thing knowing you were gonna be fucking me.”

Ashley glared at the young man, trying to decide whether she really should just throw his money back at him. She did her best to ignore what she considered a slight to her choice of underwear. The black lace bra and panty set she was wearing was the one she had worn her first time with Corey, the one she had worn for all her clients. She thought she looked sexy in them, and up until now, the guys had all seemed to think so too.

“You gonna just stand there or…”

“I’m taking it off,” she shot back, her decision made.

Normally, she would have turned her back to the client, slipped out of her bra, and faced him again for the reveal. But not today. Reaching behind her, she unclipped the bra, then pulled it off. For a moment she thought she saw his eyes widen as her breasts fell slightly to their natural position, then he smirked and shook his head.

“Not as big as I was expecting, really.”

“Sorry. Most guys like them. So, is it okay with you if I take my pants off?”

“Sure. And they’re okay, your boobs, I mean. I was just expecting more.”

“Like you’ve seen boobs before.”

“Yeah, I have. And bigger than yours.”

Ashley closed her eyes and again counted to ten as she wiggled her jeans down, much more aware than normal how much her bosom jiggled as she did so.

“The internet doesn’t count, Darren,” she countered when she opened her eyes again, standing in front of him in only her lace panties. “Most things you see on it are fake.”

“Yeah, but a cup size wouldn’t hurt you at all, so you should think about going the fake route.”

“Have fun jerking off,” the eighteen-year-old brunette snarled, having reached her breaking point.

“Yeah, I figured this was all a setup of some kind when you showed up at the door.”

“What the fuck does that mean?” Ashley yelled, fists tense at her sides, her near naked state forgotten in her anger.

“You’re scamming guys, getting their money, giving them a peep, then scurrying off like a fucking tease, sure they won’t call you on your BS because you’re Ashely Fucking Saunders. Well, I’m not afraid to call you on it, bitch.”

Ashley knew what Darren was doing, knew he was trying to goad her into staying by saying she was a tease and scam artist. She also knew it was working, and that fed her anger. But despite her rage, she forced herself to find her clam.

“No, I came here to do what I said I would do, what I know you’ve heard I will do. But maybe you don’t really want ulus escort it. Maybe you’re not even really interested in what I have to offer.”

“Fuck, get those panties off, and I’ll show you how interested I am.”

Ashley met Darren’s glare, her eyes locked on his as she slid her lace underwear down her toned legs.

“Nice shaved cunt. I guess you really are a fucking whore.”

“Fuck you, Darren,” Ashley sneered, flipping him off.

“Yes, you will,” he laughed, making her want to punch his fat face until he cried. “Now get on your hands and knees and follow me.”

With that, her pudgy classmate turned and strolled into the next room. A seething Ashley stared after him. Most of her wanted to flee, to have Corey pick her up and go someplace they could be alone. But that felt too much like letting the asshole win. Plus, she knew she would have encounters that were not exactly to her liking, and maybe it was good to get a bad one out of the way. She just hoped it did not end up being too bad.


Ashley crawled into the next room, which appeared to be the living room. Darren was already sitting on a large, red couch, his thick legs spread wide and his erection sticking up straight into the air. Trying not to let the humiliation overwhelm her, the brunette moved toward the couch. But the swaying of her pendant breasts, along with his smug stare, brought heat to her face despite her best efforts. And by the time she reached him and moved between his legs, her cheeks were on fire. But even worse, her loins were just as heated as her face, and wet enough that she was afraid he would smell her arousal.

At least he has a nice dick, she told herself, surprised that any part of him was attractive to her, especially given the way he had treated her so far. But his penis was thick, veiny, and maybe a little longer than average, and she was forced to admit to herself that she thought it could fill both her mouth and her sex very nicely. The thought brought a twinge between her legs, making her both excited and even more ashamed.

“Do you need a fucking invitation, whore?”


“Yeah, that’s my dick. Now suck.”

“No, I meant you’re a dick.”

“And you’re a cock sucking whore. Now do what I paid you to do.”

For a moment, the thought of biting him crossed her mind. But she was afraid she might really hurt him, and then he would need medical help and everything would get out. She either needed to leave or move forward without hesitation and hope it did not take too long.

“I’m waiting.”

Fuck it, Ashley thought as she leaned in to suck the head of his shaft into her mouth. Then the smell of body odor hit her.

“Fuck,” she blurted out, kneeling upright to put as much distance between her face and his groin. “Did you shower?”

“Not for a couple of days. After I saw your fucking patronizing little email, I decided to be as rank as I could be for you. Oh, and I took a piss just before you got her and didn’t shake any of it off.”

“You’re a disgusting…”

“A disgusting what, whore? Were you going to call me a ‘pig’?”

Ashley stared at Darren for several seconds, saying nothing and hating the sickening arrogant grin on his fleshy face.

“Guess I need my money back…” he started, but she cut off his words by diving forward and sucking the first two inches of him into her mouth.

The odor coming from his loins was worse than the taste of his penis, at least at first. But after a couple of seconds with him in her mouth, a sour, acidic flavor led her to gag around his thick shaft. That he chose that moment to grasp her head and forced her to take more until the tip hit the back of her throat did not help matters.

“I thought you were experienced at dick swallowing, whore,” Darren snickered when she struggled against his grip. “Didn’t think you’d gag so quickly, although it’s kinda hot knowing my dick can gag a slutty whore like you.”

Ashley fought the urge to bite down. Instead, she slapped his thighs and continued to push against his controlling hands. After a few seconds, he relented, and she pulled her lips from his erection, turned to the side, and coughed, relieved that she was able to keep her rising bile down.

“It’s not the size, asshole,” she said once she had caught her breath. “If you didn’t reek, I could swallow the whole thing. Too bad you’re never going to experience that with your stink.”

“Maybe I’ll just make you.”

“And Maybe I’ll bite your fucking dick off.”

For a moment he glared at her, and she returned the favor.

“Wait right there, bitch. Do not move,” he snarled.

Not saying a word, Ashley watched the thick young man push himself off the couch, pull up his sweats, and then storm over to what looked to be a bathroom. She heard the water running for several seconds, then Darren reemerged carrying a hand towel.

“Here, I wet one end. Clean me up then get to sucking,” Darren ordered as he pulled his sweats down to his knees and plopped onto the couch.

“How chivalrous of you,” Ashley mocked, taking the warm wet towel and moving it along his still rampant shaft. After that, she wiped through his black, curly pubic hair as well as along his inner thighs. Finally, she used the still damp part on his round abdomen before she repeated the entire process with the dry end.

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