Ashley's Prostitution Ventures #05

March 11, 2005

"I wish you wouldn't go." The words came from a cell phone speaker.

"I'm babysitting," Ashley Saunders said into the phone, avoiding the real reason for her boyfriend's concern.

"It's what you plan to do afterward..."

"We've talked about this, Corey. I need to make more money if I'm gonna get out of here when school's over."

"Or you could stay with your parents for the summer and go to college with me."

"Don't forget that one of us didn't get into Stanford, or anyplace closer to the Bay Area than SacState. And I doubt I'll go there either if I'm paying for my own food, rent, and classes."

"There are community colleges in the Bay Area," Corey said, his patient tone annoying her for some reason she could not quite articulate.

"Yeah, you keep telling me that, and I keep telling you that it's only a three-hour drive from here to Palo Alto, and that's with traffic. We'll be able to see each other."

"But you wouldn't have to... you know."

"Be a whore?"

"Please, don't."

"Don't call myself one or be one? Because I think it's too late for the second."

"I don't want to fight."

"Then don't tell me what to do."

"I'm not, Ashy. I'm asking you not to do it."

"And I'm asking you not to push me—on any of it."

"I'm just worried."

"I know. But don't be. This won't change me. Or us. Okay?"

"Yeah."

"Hey, you still taking me to my date tomorrow?"

"I guess."

"Great. I've got something to show you that I think you'll like."

"Okay. See you then," her boyfriend said with almost no inflection.

"Yep, see you then, baby. Love you."

"Love you too, Ashy." At least there was some life in his voice with those words.

The eighteen-year-old brunette ended the call and sighed. Corey would come around. At least she hoped he would. But for now, she could not worry about it. She had to get ready for her evening without it being obvious she was prepared for anything more than babysitting.

Ashley pulled her new, hot pink bra out of her backpack, which she had used to sneak it into the house. The undergarment cost more than any other single item of clothing that she owned. The push-up structure of the bra and padding at the bottom of the cups created the illusion that she was at least a cup larger than her actual size. It also maximized her cleavage, something she felt that Ken Davidson, her babysitting client, would appreciate. And once he did, she would move forward her plan of making him a different kind of client.

Since January, Ashely had been helping her male classmates of suitable age in a very special way. They paid her $100, and she took their virginity. Her first client, Corey, became a kind of business partner—he drove her to her 'dates' and received sex in exchange—and then her boyfriend. He did not like the idea of her expanding to older clients, but she wanted to make more money. So far, she had earned over $1700 from her new occupation, but she knew that would not be enough both to buy a car and to move out of her parents' house by graduation, if not sooner. It did not help that the new bra had set her back over $100. But she was confident that Mr. Davidson would provide the perfect opportunity to grow her business.

***

"Mr. Davidson, can we stop and get a drink," Ashley asked, composing her full lips into a slight pout.

"Um, yeah, I guess," the older man said, his eyes meeting hers before they dropped to her chest for a slightly longer than fleeting moment.

Ashley suppressed a smile. The thirty-something Ken Davidson must have noticed the illusion of extra heft that her new bra gave her bust. He always tried to sneak a few peaks if he drove her home after she babysat for him and Mrs. Davidson, but nothing like tonight.

The brunette, her soft hair curled somewhat more than usual, unhooked her seat belt as they parked at a convenience store. A touch on her leg brought unexpected butterflies to her stomach, and she met Davidson's gaze.

"I'll get it, Ashley. My treat."

"Thanks, Mr. Davidson! Can I have a Diet Coke, please?" she patted the hand resting on her denim-clad thigh.

"No problem," he said, exiting the SUV. Ashley watched him as he walked away. The man was tall, maybe a bit gangly, but he seemed in decent shape. She could do worse for her first older client.

Ashley unbuttoned the top two buttons of her dark gray, fitted blouse and examined herself in the visor mirror. She undid the third button, winked at her image, and flicked up the visor. Davidson should see not only a good amount of the impressive cleavage created by the bra, but the hot pink material of the bra itself.

The eighteen-year-old drummed her fingers on the dashboard, looked out the window, and wondered what might be keeping Davidson. Several seconds later, she checked her appearance again in the visor mirror, this time intending to focus on her makeup. But she rechecked the look of her open blouse as well. The black lace bra she normally wore on dates with clients was more comfortable as well as sexier looking, in her opinion, but she could not deny the benefits of this one.

"Sorry that took so long," Ken Davidson said as he entered the SUV. "Here's your diet..."

The man's words trailed off and he openly, unabashedly stared at her chest. Ashley took the offered bottle of soda, making sure to brush his fingers as she did so.

"Um, we should get going," the man finally said, starting the big SUV.

"Okay. And thanks again for the soda." The brunette opened the bottle and sucked the top of it between her lips, hollowing her cheeks briefly before she drank. From beside her, the older man's sharp intake of breath told her he had noticed.

"Is it okay if I take the back way?".

"Sure." He almost always did anyway, and before she had wondered whether the reason was to spend more time with her or less with his wife. Tonight, she did not wonder.

The Davidsons had lived down the street from her family, and she started babysitting their kids a few years back. Now they lived across town, and while she still babysat for them regularly, the drive time was much longer. It was even longer still if one took the backroads, but such a route offered many secluded places to stop. That had been a factor in choosing Ken Davidson.

"I know you could pick someone closer, so I really appreciate you guys asking me to babysit," Ashley said after a few minutes of silence, during which Davidson's increasingly less furtive glances at her exposed cleavage assured her of his interest. "I'm trying to save up for a car. I have almost $500 saved from babysitting over the years, but that's not enough. So, I started a new business with some of my classmates."

"Oh? What kind of business, Ashley?" Davidson's voice seemed strained, as if he had to force it to some measure of normality. The young woman did not bother to suppress a smile. She touched his thigh and ran her fingers toward his groin.

"I relieve them of their virginity, for a price."

"Ah, you're joking around with me." It was not a question. Ashley suspected he had said it more to convince himself than anything else.

"I'm not," she told him in her huskiest voice. As she spoke, she rubbed his inner thigh, fingers inches away from his crotch. "But I need to expand my, um... services."

Davidson groaned and pulled the SUV off the road. His fingers found her wrist and tightened around it, but he did not move her hand away. Brown eyes, hopeful and excited if she were any judge, stared at her. She moistened her parted lips, reaching her free hand up to stroke his dark hair.

"So, are you interested in helping me increase my earnings?"

"God, yes," the man croaked, releasing her wrist and sitting back in his seat.

Ashley grinned, leaned toward him, and massaged the bulge in his slacks. Davidson gasped and closed his eyes. The eighteen-year-old squeezed his erection, noting the thickness of it. The choice of Ken Davidson seemed better all the time.

"A blowjob is $150," she told him, stroking his length through his clothes. "A cock-worshipping session would be $250. Fucking my pussy is $300. If you want a combo, we can work out a deal."

"Fuck," the man said, staring at her in apparent disbelief.

"Are you expressing your amazement or what you want?" she teased him.

"What does 'cock worshiping' entail," Davidson asked after several more seconds of him doing nothing but staring at her.

"Oh, you'll love that, Mr. Davidson.," Ashley smiled, giving his hard penis another squeeze. "I'll use my fingers, mouth, and boobs to take you to the edge of coming and keep you there. By the time you finally come, you'll explode."

"What if I wanted that and sex?"

"Well, I'd say we need more time. After a good cock-worshipping session, you'll need a bit to recover." At least she suspected that to be true. Ashley did not have direct experience with older men, so she relied on what she had heard from a friend who did.

"Oh, that makes sense."

"But I could suck you off quickly and probably get you hard again if you want sex. That's what I do for the boys. It helps them last longer for their first time too, since they've already come. I'd do it for $350."

"Umm... I don't have that much on me."

"How much do you have?"

"$230 something, I think."

"Well, you can get just the blowie, if you like, and we can set up a date for later."

"Would you take $230 for the cock worshipping?"

"Sure, Mr. Davidson. For you," she purred.

"Okay, do you want the money now?"

"Yes, please. I always ask the guys to pay first."

"That's smart," the older man nodded, taking a stack of bills from his wallet. "Do you want me to count it?"

"I trust you," Ashley took the money and stuffed it in her purse. While she was occupied, Davidson grabbed her nearest breast and squeezed it.

"Not quite yet, Mr. Davidson," she scolded him, moving his hand away. "I'm in charge, okay?"

"Um, yeah. Fine," the man nodded, his gaze locked on her chest.

"Unless you want to pay me enough to take charge. We'd have to negotiate that."

"Really?"

"Yeah," Ashley shrugged, hiding a sudden nervousness. She had not planned on offering anything of the sort. But now it was out there, and Ken Davidson seemed interested. She wondered how much she could charge him. "But let's talk about that later. I have this hard cock to worship."

"Okay..." he gasped while she loosened his belt, unbuttoned his pants, and yanked the zipper down. "Do I get to see your tits?"

"All in time, Mr. Davidson," she grinned, pulling his erection free from his boxers, noting that the man looked to be longer than anyone she had been with before.

"You can call me Ken," he told her, but whether he planned to say anything else, Ashley had no idea. His voice squeaked at the end of his name, coinciding with her lips wrapping around the head of his penis. When she swirled her tongue around the sensitive skin of his glans, the older man groaned and thrust his pelvis up. She swallowed half his length. She knew from experience with Corey, who was as thick and almost as long as Davidson, that she likely would not be able to deepthroat the man at this angle. But since she had not told him that would be part of the service, she doubted he would miss it.

"That feels fucking fantastic, Ashley," Davidson told her, his hands resting lightly on her head. "But didn't you say..."

"This is the warmup, Ken," she replied. "Trust me, you'll be delighted by the time I'm done."

"Okay," he sighed as she engulfed his shaft again, this time sliding her lips up and down the top half with deliberate slowness.

"My wife almost never does this anymore," he said out of nowhere a few seconds later.

Ashley felt a surge of guilt. She knew Mrs. Davidson, had known her since before the couple's kids were born. And here she was, sucking on her husband's penis. But a warm tingle from her loins, as well as the memory of the stack of bills Davidson had given her, helped her overcome any doubts.

If she satisfied him, would he really pay me for this?"

she rationalized. And when her conscience did not answer, she buried her misgivings. She had a job to do.

With a loud pop, Ashley pulled her lips from the man's erection. Sitting up, she smiled and unbuttoned her blouse. Davidson licked his lips and leered. Little jolts of pleasure shot from the eighteen-year-old's damp sex. She embraced the unanticipated arousal, sure it would aid her in providing an enthusiastic cock-worshipping session for her client.

"Want to see them now?" she asked, cupping her breasts over the hot pink bra. Her folded blouse lay on top of the dashboard.

Ken Davidson only nodded. Ashley's nipples stiffened, both in anticipation of the cool air and from the realization that she had rendered the man speechless.

"Okay," she grinned, unhooking the front clasp, the little surprise that had caused her to spend more on the bra than she had planned.

As the halves of the bra fell away and her breasts bounced to their natural position. Davidson moaned, his eyes seeming to bug out of his skull. Concern that he might be disappointed now that the illusion of her being a cup size or so larger proved unfounded as she watched his eyes examine every inch of her naked chest.

"Amazing tits," he said after several seconds. He held out his hands but stopped short of touching her. "May I?"

God, yes

, a voice in Ashley's head moaned. "Of course, Ken," she said aloud.

Tentative at first, his fingers traced the contour of her breasts. She thrust her chest forward, hoping he would turn his attention to her achingly hard nipples. A little moan escaped her lips when he finally did, and she failed to repress a shiver. She thought she detected surprise in his widened eyes.

"Can I taste?"

"Please," Ashley breathed, only aware after the word left her mouth that she intended to say it.

Davidson's tongue, wet and a little rough, lapped at first one nipple, then the other. Ashley shuddered and moaned. She considered stopping him. She was supposed to be pleasuring him. But when he sucked her nipple into his mouth, she mewled and stroked his hair.

A new idea occurred to her. Would it be so horrible if she let him have sex with her tonight even if he did not pay for it? He could pass along her anonymous email to his friends, help her build an older client base. Would that not be worth the freebie?

What about Corey

? The thought floated through her mind, uninvited. Her boyfriend was not in favor of this new enterprise. If he knew that she had let herself become aroused enough to consider sex with her older client without any additional charge, he would probably be angry and hurt.

Keep it under control, whore

, she told herself.

You're in charge. If he wants more, he has to pay. Period.

Ashley tugged on Ken Davidson's hair. He looked up at her. She pulled him up for a quick kiss. It grew longer, their tongues battling. When they broke apart, both were short of breath.

"Sit back and relax, Ken," Ashley told him, needing to move things along. If this went on too long, she feared she would give in to more.

"Okay..."

"So, has your wife ever worshipped your big, thick cock?" she asked the man, fingers tracing his twitching member.

"Um, she used to give me more BJs. That happens a lot less now."

"How often?"

"A few times a year, at most. My birthday. Christmas. Our anniversary. You know, special days."

"What about steak and a blowjob day?"

"What?"

"March 14th. It's Valentine's Day for guys."

"That exists?"

"Yep," Ashley said.

And Corey's gonna get a steak sandwich for lunch and then one hell of a blowjob when we go to his place after school

, she added in her head. She had not yet told her boyfriend her plans, but she had verified she could come home with him on the afternoon of the 14th.

"I doubt it," Davidson said. "She probably never heard of it either."

"Too bad. You have such a suckable dick." To emphasize her words, the brunette slurped the man's penis into her mouth, sucking and licking first the head, then the shaft as she bobbed her head up and down.

"God, you're an awesome cocksucker," he said, voice raspy.

A thrill of excitement radiated from her clitoris at the compliment, setting her skin tingling. The eighteen-year-old made herself think about Corey, hoping that would help suppress her growing arousal. But it had the opposite effect.

Almost too late, she noticed Davidson's heavier breathing and twitching penis. She slipped her lips off him, planting light kisses up and down his slick shaft. The man panted, hands on her head, body tense. After several seconds passed, his breathing eased, and he relaxed back into the seat.

"That was close," Ashley said between quick pecks along his length.

"I almost came," he croaked, staring down at her.

"Sorry. I kinda got carried away sucking. I'll pay more attention."

"Don't be sorry. I've never felt anything like that, being just on the edge of coming like that."

"But I still need to use my boobs," the young woman said. "But that might work better in the back."

"Okay," the man agreed.

"Can you fold up one of the second row seats?"

"Yeah. Why?"

"Oh, you'll see. Go sit in the back row and tilt up the seat in front of you."

Ken Davidson nodded, pulling up his pants. Holding them, he got out of the car, opened the back door, folded one of the second row seats forward, and climbed into the back, closing the door behind him. While he did so, Ashley wiggled out of her jeans, taking her socks and shoes off with them. Once she was down to just her pink panties, she crawled between the front seats and past the second row, ending up on her knees in front of the staring man.

"You ready?" she asked him, but she did not wait for an answer. She pushed her breasts around his throbbing erection, trapping it. The man moaned and stroked her hair. His eyes held hers, although the lids fluttered when she started moving her breasts up and down his length.

"You ever tit-fuck a girl before, Mr. Davidson?" she asked, reverting to her prior mode of address. The man groaned and shook his head. "Do you like it?"

"Yes," he gasped, nodding vigorously as well.

"I bet you'll like this too," Ashley grinned, moving down until the purplish head of his penis stuck out between her smashed cleavage. Making sure to maintain eye contact with her client, the brunette licked the spongy tip.

Davidson's grip on her head tensed, and for a heartbeat, Ashley thought he might force her head down so she had to take him in her mouth. Despite her earlier caution that she was in charge, a spreading wetness dampened her panties. But he did not make her take it deeper.

Both relieved and disappointed, Ashely straightened her neck, winked at her client, and pressed her breast even tighter around his shaft. Davidson moaned and grasped her hair. She picked up speed. The man humped his hips. Friction built up, so she worked up enough saliva in her mouth to let it flow over her bottom lip, falling between her breast, lubricating both her flesh and his penis. He groaned louder.

Maybe a minute later, Ashley dropped her hands, letting her breasts fall away. Ken Davidson gasped and shuddered. His fingers in her hair trembled. She was sure she had brought him to the edge again. She kissed the underside of his shaft and it jerked. She kissed it again, then ran her tongue up to the tip. When the man's body stiffened, she wiggled it back down to the base. A thought occurred to her, something she had not even done with Corey yet.

The brunette licked lower. She fought back an initial revulsion at the feel of his pubic hair and the wrinkled skin of his scrotum on her tongue. But within seconds, it faded. She concentrated on her task and the man's increasingly frequent moans and groans. He clearly enjoyed what she was doing, and that made her want to keep it up.