Ashley's Prostitution Ventures #02

Author's Note:

I appreciate all the feedback I received on the first installment of

Ashley's Prostitution Ventures

. I do need to clarify an issue regarding the structure of this series. I did not intend the first installment to be labeled as Ch. 01. The title I submitted was

Ashley's Prostitution Ventures #1,

but it was changed when it was published. I am hopeful that for this second installment the title will not be given a chapter designation.

My plan for this series is for the installments to be stand-alone episodes (with some setup for future episodes as needed, as in the first installment) rather than chapters of a larger work. Each individual installment will focus on a new adventure for Ashley, although recurring storylines (e.g., her relationship with Corey) will also appear in most installments. For example, the second installment below includes the story of her second client as well as new developments in her relationship/deal with Corey. The third (which should be available in April) will focus on a less positive client experience for Ashley.

My plan for the foreseeable future is to post one installment a month starting after the second installment posts. I may take breaks here and there between installments, but I will endeavor to stay as close to a monthly schedule as I am able.

Thank you,

Kveldulf

Please note that the following story is fictional, and all characters involved in sexual activity in the story are eighteen-years-old or older.

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Ashley's Prostitution Ventures #2

January 2005

"You sure about this Ashley?" Corey asked the eighteen-year-old brunette, his concern evident in both tone and expression.

"Yeah, I'm sure," Ashley Saunders told her her friend, although her churning gut was trying its best to contradict her words. "It's all good."

"Well, you look really pretty," the young man said, his cheeks reddening.

"Oh, opposed to normal when I look like crap?"

"No, you're pretty all the time."

"You said I was beautiful last week. Was that only because I had just fucked you?"

"What? No. That's what I'm saying—you're beautiful."

"Beautiful isn't the same as pretty," the young woman countered, a bemused smile on her full lips as she watched her friend squirm.

"Are you messing with me?"

"Maybe."

"To stall going in because you're not sure about this?"

Ashley opened her mouth to object but said nothing. Corey was right. She was stalling. But she was not doing so for the reason she suspected Corey believed. The banter with him was helping her ready herself for the task ahead. Since she had started teasing him, warmth and wetness had spread between her denim-clad legs

"Oh, I'm sure, dude," she told him, brushing her lips against his. "I'll call you when I'm ready to be picked up. Then maybe we can find a nice place to park."

"Maybe," her partner grunted as she got out of his car.

***

"Hi Grant!" the brunette said, smiling at the bespectacled young man who opened the door. "Um, can I come in?"

Grant Limbocker stared, eyes wide, jaw slack. Like Corey, Grant was one of Ashley's classmates and had recently turned eighteen. He was also painfully shy in addition to being one of the 'geek' group at school. Still, like with Corey, she had known him since grade school, and both she and Corey had felt he would be a good choice to be her second client. Based on the look of terror etched on his pale face, however, Ashley's confidence in that decision wavered.

"You okay?" she asked when he continued to stand by the open door and stare at her even though she had walked well into his house.

"Ashley Saunders? You are the companion?" he inquired, voice breaking on the second question.

"Um, I'm not sure what you mean," Ashley replied, although she had an idea what he must mean. It was the use of the term 'companion' that had thrown her.

"Like Inara. From

Firefly

."

"Still in the dark here, Grant. What's an 'Inara', and what's it got to do with lightning bugs?"

"

Firefly

was a TV show. Inara is a character on the show. She is a companion."

"So, like a call girl or something?"

"Only in the simplest terms. She is much more. Companions are elegant, trained courtesans who provide many intimate services. They are respected, almost revered, members of elite society among the Central Planets."

"Oh, I see," Ashley replied, although half of what he had said seemed like nonsense to her. "But in the, um, 'simplest terms', these 'companions' have sex with men for money, right?"

"Well, not always sex, and not always with men. Companions are more than prostitutes, as such women of ill-repute exist in the 'Verse and are contrasted with companions. Although, the episode that directly dealt with such characters never aired on TV. It is available on DVD..."

"Yeah, I get the gist of it. And I guess the answer is yes, I'm a companion, as I wouldn't want to be considered a woman of 'ill-repute'. Now, to more important matters, is there someplace I can put my coat, Grant?"

The skinny young man blinked several times, then closed the door behind him. Ashley hoped that was a positive sign that they could move past whatever he had been going on about.

"Um, I can take it," he finally said, his voice squeaking on the last word.

"Thanks," Ashley beamed at him, handing him the coat while pushing out her chest.

Grant blinked a few more times as his gaze settled on her cleavage, but he made no move to take her coat. The young woman let out another sigh, then shook the garment at him. When he still did not respond, she called his name.

"Huh?"

"My coat?"

"Oh, sorry," he mumbled, his face a bright pink.

"They're just boobs, Grant," she chuckled, hoping to put him at ease. "You'll see more of them soon enough,"

Her words did not have the intended effect. Her classmate's face went from bright pink to gray in an instant, and he let her coat slip from his fingers and fall to the floor.

Shit, this isn't going well

, she told herself as she picked up her coat and threw it on an armchair in the living room.

For this to work, I'm going to have to take charge.

"Relax, Grant," she purred, taking his clammy face between her palms. "And enjoy yourself."

Not waiting for a response from the obviously overwhelmed young man, she kissed him, her tongue pushing against his firmly clamped lips. After a few seconds, his jaw relaxed, and her tongue slipped into his mouth. He did not reciprocate, however.

"You don't like kissing?" she asked him when she pulled back.

"Um, I don't know."

"You don't know if you liked what I just did?"

"No. I liked that."

"So, you like kissing?"

"I have never kissed anyone like that before, so I don't know if I like kissing. All I have the data for is kissing you."

"But you liked that, right?"

"Yes. Very, um, very much."

"Want to do it again?"

Grant nodded but made no move to do anything. Fighting the urge to roll her eyes, Ashely leaned in and again brought her lips to his. This time, she pushed her tongue into his mouth right away. But even after several seconds, he had not responded in the way she had hoped.

"Put your tongue in my mouth when I kiss you," she whispered in his ear. "Push it against mine."

"Oh," the again pink-faced young man replied before she renewed the kiss.

When his tongue met hers, she felt an unexpected twinge between her legs. The initial awkwardness of the situation had dispersed any lingering arousal she had been feeling from her teasing banter with Corey in the car, but Grant actually reciprocating in the kiss was enough to bring some of it back. Deciding to blaze forward, the young woman took her client's trembling hand in hers and brought it up to her chest. For a moment his palm just rested against the swell of her breast, then it gave a tentative squeeze.

I didn't expect that,

Ashley thought as a jolt of pleasure shot from her chest to her pussy.

He's barely touching me.

But it was enough, she realized. The feeling of providing something that the young man could have never had without her help, a sensation that was much stronger with Grant than it had been with Corey, worked its magic on her. She doubted Grant would be able to take her to orgasm like their friend had, but at least she should be ready for sex by the time she led him to that point.

With a gasp and a jerk, Grant recoiled from her, his unexpected action pulling her out of her thoughts. Ashely stumbled, almost falling forward into him. At the same moment, he stepped back, wringing his hands and looking everywhere but at her.

"What the fuck?" she snapped, glaring at her classmate as he seemed to shrink in front of her.

"Sorry, Ashely," he replied, eyes moist. "I did not really expect this. I thought Corey was joking around about, um, knowing a companion who could take my virginity. And then you showed up, and I knew it must be a joke, because you are, well, you."

"So, what's the joke? Me being a whore and willing to fuck you for a hundred bucks?"

"Companions are not whores. Like I said..."

"I'm not a companion, Grant," Ashley snapped, unable to stop her voice from betraying her annoyance. "I'm a whore. I'm here to fuck you, to 'take your virginity' as you put it, if you have the money. Is that the problem—that you don't have the money?"

"No. I, uh, I do. Have the money, that is."

"Okay, so go get it and we'll get down to business. Did Corey tell you what would happen? I'll suck you off first, since that will probably help make the actual sex more enjoyable for us both. Then I'll get you hard again...

"In the 'Jaynestown' episode of

Firefly

, Inara is engaged to be the first experience for the magistrate's son. There is a greeting ceremony that she performs before the physical intimacy," Grant interrupted, wiping his hands on his pants as he spoke.

"And if I'd known about that being what you wanted, I would've watched the show and come prepared. But I didn't know, and I don't know any ceremonies for, uh, this. So, if I'm not going to be acceptable to you..."

"No, you are, um, you are much more, uh, much more than acceptable."

"Great. Then go get the money, and then we can have some fun."

"Okay," the skinny young man nodded before scurrying away.

What the fuck have I gotten myself into?

Ashley asked herself.

***

"Did you like feeling my tits?" Ashley asked Grant once she had the hundred-dollar bill stashed in her purse.

"Well, I only felt one..."

"So, you only have the data to say whether you liked feeling that one, right?"

"Right," the skinny young man smiled as he nodded.

"And did you? Like feeling that one, I mean?"

"Um, yes. It was... incredible."

"You want to see them?"

The eighteen-year-old brunette did not wait for an answer. She unbuttoned her blouse, then tossed it on the chair on top of her coat. Her client's eyes, which were fixed on her bosom, looked as if they might explode out of his face. When her bra followed her shirt, Grant's mouth fell open.

"You like?" Ashley asked, cupping her breasts with her hands, pushing them closer together.

"Yes," the young man breathed, his eyes larger than ever.

"Want to see my puss too?"

"You're what?"

"My pussy. My vag? My honeypot?"

Grant nodded, and Ashley figured that he was once again speechless. Taking pity on him, she gave him a kiss on the lips before starting to work her jeans and panties down her hips.

"Oh. You are shaved. Like the girls in pornography online."

"Oh, you've seen porn?" she asked as she leaned toward him, letting her breasts hang in his line of sight as she finished removing her pants. The low moan from the young man assured her that he was enjoying what he was seeing, even if he did not really know how to express it.

"Um, yes," Grant nodded.

"You've seen girls suck dick?" Ashley asked, straightening back up.

This time, he only nodded, eyes still glued to her chest.

"And would you like me to do that for you?"

Another nod was his only response before he pulled his polo shirt over his head, exposing white skin and a narrow, almost sunken chest.

"Slow down there, Mr. Eager," the brunette smirked. "Let your companion do the work."

"You said you were not..." Grant started to object, his eyes finally traveling back up to her face.

"I did, but let's pretend I didn't so you can pretend that I am what you want me to be."

"Oh, Okay, I guess. I mean, I would like that. Thank you, Ashley."

The young woman gave her nervous client what she hoped was an encouraging smile, then she dropped to her hands and knees and crawled forward, scrutinizing his face as she closed the short distance between them. As she had expected, shock was the first emotion to show on his pale face. But after that, she thought she saw something more primal drive the shock away.

Nice to know he can feel lust

, she told herself as she knelt upright in front of him and yanked his zipper down.

This might not be as bad as I thought.

"You're nice and hard," she purred before mouthing the bulge of his erection through his white, clean smelling briefs. "Guess you like your companions a bit more on the whorey side, huh?"

"Uh, I guess."

Chewing her bottom lip and making sure not to lose eye contact with the young man standing in front of her, Ashley pulled Grant's underwear down, letting his longer than expected penis bounce free. Dropping her gaze, she studied his manhood, noting that the shaft was skinnier than the head. None of the guys she had been with before had such a shape, and she wondered how it would feel inside either her mouth or her pussy.

"Nice," she smiled up at him, giving the tip a kiss and pushing her tongue into the hole to lick out his oozing precum. "You want me to suck on it now?"

"Y...y...yes," Grant stammered, his pelvis moving forward maybe an inch or two.

Opening her mouth wider, Ashley engulfed the head of his shaft, lips tightening just where his penis narrowed behind the mushroom tip. Making sure to reestablish eye contact, she winked then wiggled her tongue against the underside of his bulbous crown.

Seconds later, Grant let out a long, low groan as his hips bucked forward and pushed his length another couple of inches into her mouth. Ashley sucked hard for a second, then the twitching of the penis in her mouth alerted her that she had miscalculated. But it was too late. Salty and slightly bitter semen gushed over her tongue and into her larynx.

Not thinking of the consequences, the eighteen-year-old brunette ripped her lips off her young client's erection, dropped to her hands and knees, and coughed semen from her mouth and nose. And while she did so, feeling a growing ache in her chest as well as a burning sensation in her nasal cavity, she came to the awareness that something cold and damp had landed on her scalp.

"Did you get cum in my hair?" she croaked, glaring up at Grant.

"Sorry," he moaned, backing away from her. "I could not help it. You pulled away but it was still going everywhere."

"Fuck, Grant," Ashley sighed, sitting on the floor. "Warn a girl if you're going to shoot that soon. I think I took half your load down my windpipe."

"You have some, um, stuff coming out your, uh, nostrils."

"Yeah, and it burns like hell," she replied, using her hand to wipe her nose and upper lip.

"I should get you a washcloth," Grant announced, then he was gone, leaving her naked on the floor.

***

"Thank you for getting the washcloth and showing me where the bathroom is," Ashley said, strolling into Grant's bedroom where he waited for her, shirtless. "I'll still need to take a shower before I leave to make sure I got everything out of my hair, but I'm good to go."

"Again, I am very sorry, Ashely."

"It's done. It's not a problem. And let's just say I'm glad I sucked you off first, because I think you would have been pretty disappointed in your first time if you had exploded in my puss that fast. And speaking of your first time, we should move on to the main event. How do you want me? Doggy style? On my back? Riding you?"

"What do you like?" the young man asked, backing into a corner of his room.

The room looked much like Corey's, expect more sterile. While Corey's room was as tidy, his walls were adorned with game posters and his shelves topped with different models of what she had assumed were spaceships. No pictures of any kind decorated Grant's walls, and his bookshelves contained only books. It was as if the room had failed to absorb any of the personality of its inhabitant.

Or maybe it has,

a voice in her head spoke up.

Maybe it's his personality that is too sterile.

"It doesn't matter what I like, Grant. This is what you want."

"On your back then, I guess."

"So, you don't want me to take charge and ride you? That might be easiest for you."

"No," he replied, his voice growing stronger as he took a few steps toward the middle of the room. "If I am going to lose my virginity, I want to be the one who, um, does the work."

"I can't argue with that," the brunette chuckled, pleasantly surprised by even a modicum of assertiveness on the young man's part.

Ashley climbed onto the twin bed before rolling to her back and spreading her legs. For a moment, she noted that Grant's eyes fixated on her exposed, and again damp, sex. A smile crossed her lips, and she slipped her fingers between her legs and used them to spread her labia.

"You want to ram your dick inside there?" she asked Grant, who nodded without looking up.

Reaching down with her other hand, Ashley slid two fingers into her vagina. It was not as slippery as she would have liked, so she pumped her digits in and out a few times to get everything flowing. The combination of the sensations from her warming loins and the shocked and lustful expression on Grant's face brought her to readiness in only a matter of seconds.

When she withdrew her now dripping fingers, she watched her client's eyes track them as she brought them to her lips and sucked them clean. The young man gulped, then struggled to remove his pants, underwear, and socks. And while she watched him, afraid he would fall, Ashley realized that she should have helped him undress before getting on the bed. She sat up, intending to assist him, but Grant had already managed somehow to remove everything without tripping. His jutting erection leading the way, he climbed onto the bed.

Smiling, Ashley wrapped her hand around his skinny shaft and used it to gently pull him toward her. When he was in position, the bulbous head of his shaft poised between her wet and swollen labia, she let go of him and ran her hand up his narrow chest.

"Ram it in, Grant," she breathed, pushing her pelvis toward him.

The young man closed his eyes, shuddered, and pushed his way inside of her. As he did, Ashley felt her pussy expand around the bulbous head then tighten around his shaft. She did not feel as full as she had with Corey or other guys with thicker penises, but that rounded tip of it stimulated her in a way that caused a sudden wave of tingles to spread from her loins to her belly.

"Does that feel good?" she asked him, hoping he would slide the rest of the way inside of her. "You're not a virgin anymore."

"No, I am not," Grant agreed in an awestruck voice. "And I never dreamt it would feel this good."

"Bury it in me," she moaned, humping up at him. "Fill me all the way inside."

Grant stared at her for several seconds without moving. But just when she thought she would have to encourage him more, he thrust home. And as he did so, the crown of his penis rubbed inside of her, igniting more tingles and eliciting a throaty moan.