Ashleys Prostitution Ventures 06

March 12, 2005

"So, what was it you were going to show me?" Corey Strickland asked.

"Oh, that has to wait until afterward," Ashley told him, patting his thigh.

"Does it have something to do with why your... um... chest seeming larger today?"

"Maybe," the brunette eighteen-year-old grinned. "A girl has to keep her secrets... until it's time to show them."

"Oh. Sure," her boyfriend said, but Ashley was not convinced he believed her.

"It's nothing bad." She did not like silence between them, so she decided to give in a little. "Just a new bra."

"You don't need it," Corey grumbled.

"I kinda do need bras. Well, maybe not need, but really, really prefer having..."

"Not a bra. That bra. One that's... like that."

"Like what?"

"You know."

"Makes my tits look bigger? Who are you to say what I need, Corey? Maybe I like the way I fill out my clothes with this. Maybe I just want to see what it's like to have larger boobs. Maybe..."

"This is because that asshole Darren said you needed a boob job."

Ashley sat back in her seat, arms crossed over the topic of conversation. She did not want to talk about Darren Connors or anything he did or said on their 'date'. He had been by far the worst client she had dealt with since deciding to take money to relieve select male classmates of their virginity. Corey had been the first, but that developed into something more. The rest were mainly nerdy type guys, awkward or shy or just distant, but none mean. Except Darren.

"You don't. Your tits are perfect."

"I don't need you telling me what my body is," Ashley snapped, regretting both her words and her tone.

"You're right," Corey nodded. "It's not my position to tell you what to think about your body or what to do with it. But I can't quit caring, and I can't sit by and say nothing when I think you are making a mistake."

"Let me off here," she said, hand gripping the door handle. "I'll walk the rest of the way."

"I can't not say anything because I think you're beautiful the way you are?"

"Don't give me that bullshit, Corey. This is about me fucking Ken Davidson last night. About me trying to get older clients. About me becoming someone you don't want to be with."

"Thinking you're beautiful is not bullshit and you know it," the young man said, anger hovering at the edge of his voice. "But I am worried about you. You don't have to do all this."

"Not again, please."

"It's few blocks more. Do you want me to stop?" Corey asked. She had wanted him to change the subject, so why did it make her even more angry that he did what she asked?

"No."

"Fine."

They spent the next several minutes in silence, and Ashely suspected that her boyfriend found himself as lost in his thoughts as she was in hers. She did not want to fight with him. But it seemed fighting and sex, either in person or over the phone the night before, dominated much of their time together lately. That had not been the case on Valentine's Day, and the memory of the evening they had spent together helped erode her irritation with Corey.

"I'm sorry," she said as they pulled up to an older one-story house.

"Me too, Ashy," her replied, and the love in his blue eyes almost made her decide to forget her scheduled 'date' and go someplace with him. "We probably should talk about..."

"Everything," Ashley finished for her boyfriend. "And not when you're taking me to... well, you know."

"Yeah."

"I love you," she said, leaning in to kiss his soft lips.

"Love you to," he said before she exited the car.

Ashley resisted the urge to look back at Corey as she walked up the driveway toward the house. The lawn, green and well cared for, contrasted with the brown house with its slightly darker brown door. And to Ashley, who had spent much of her life hating the color of her eyes and hair, brown was boring. Corey did not think so, but he had blonde hair and blue eyes. What did he know about having to watch as everyone fawned all over people with his coloring?

It's not his fault,

she told herself. And she accepted the truth of that. But accepting it did nothing to allow her to feel better about herself.

She knocked on the dark brown door. When she started her ventures into prostituting herself, she would have been nervous at this point. She might have even needed to calm her breathing or make herself relax. But not anymore. Plus, it was only Simon Lancaster, a shy, soft, pudgy boy who seemed scared of everything, including girls. Her main concern about the 'date' was a fear that she would be sore from the sex the night before with Ken Davidson. But after a restive sleep, she felt ready to go.

The door opened to reveal Simon, who stood in the doorway, mouth ajar, his eyes roving over every inch of Ashley. For several seconds she waited for the inevitable, "Your Ashley Saunders" or something to that effect, but it did not come.

"May I come in, Simon?" she asked in a soft, sweet voice after several seconds of awkward silence. but the young man just blinked, and Ashely's smile faltered. This was going to be a lot of work, she realized.

"Simon..."

"Uh, okay," he muttered, eyes cast down, hands in pockets as he shuffled to the side, leaving just enough room for Ashley to squeeze by him.

"Nice house," she said, amazed by the cat figurines and pictures everywhere. The faint aroma of a cat box reached her nose, and she scanned the entry way and living room for the furry little creature or creatures she knew must be somewhere.

"My mom likes cats." Blurted the young man, eyes cast down and cheeks red.

"Cats are cool," she told him, running her fingers up his arm. The young man widened eyes met hers for an instant as he stepped back out of her reach.

"My mom got a lot of them when my dad left," Simon told her after several seconds of silence, his gaze again locked on the floor between them. "They're okay."

"So, you want to go up to your room?" A feeling she could not quite name but knew she did not like had settled in the pit of the brunette's stomach. Moving this along would probably help. At least she hoped it would.

"Um..."

"I'll strip for you, if you want."

"Really?"

"Yeah. I mean, that's why I'm here, right? To do things for you?"

"Really?" he repeated, and this time the word ended with a squeak.

"Yeah. If you got the hundred. You do have it, right?"

"Yeah." Simon nodded while fishing a wad of bills out of his pocket. He handed the case to her, and Ashley noted the dampness of his hands from the brief contact during that exchange.

He's nervous as fuck,

she thought, wondering how she could help alleviate some of that. With some other clients she had done it by being the aggressor. But she feared that might backfire with Simon.

"It's all there," he said in a rush as she straightened the bills.

"I trust you, Simon. Do you trust me?"

"Uh... yeah."

"Good." Ashley shoved the money into her purse, set it beside a Japanese style Lucky cat statue on a small table, and held out her hand. Simon was at most a few months her junior, but he seemed much younger. She felt his moist hand tremor as it clasped hers, and she gave him what she hoped was a reassuring smile. "Lead me to your room."

The mousey-haired boy led her down a hallway adorned with more cat pictures and into a small, cluttered bedroom. Superhero figurines stood on almost every flat surface, and comic book posters covered nearly every inch of visible wall space. Many were of female superheroes whose exaggerated curves were covered by tight, skimpy costumes.

"If I would've known, I could've brought a Wonder Woman costume." A large poster of the character hung over Simon's bed, and she guessed from that and the number of Wonder Woman statutes that she must be a favorite of his.

"You'd... you'd do that?"

"Sure," Ashley shrugged. "But I wouldn't fill it out quite like her.

"You're beautiful, Ashley," he said, eyes cast to the side. "You'd make a great Wonder Woman."

"Well, maybe after today, we can come to a deal..."

"I... we have a costume."

"You do?"

"It isn't mine," he said, face crimson. "It was my sisters from a few years ago. It's in her room."

An image of Jeanie Lancaster, Simon's sister, swam to the surface of Ashely's mind. Jeanie, a thin, pale, blonde-haired girl a few years older than Simon, seemed the least likely woman Ashely could think of to wear a Wonder Woman costume, but she must have at some point.

"We had a big family Halloween party. She was Wonder Woman, Dwight was Batman, and I was the Flash."

A new mental image, this one including a pudgy Flash and a rotund Batman alongside a skinny, blonde Wonder Woman, filled her head, and Ashley had to stifle a laugh. Dwight Lancaster, Simon's older brother and Jeanie's twin, was a large, round young man with long, lank, brown hair. Like Jeanie, he had gone off to college a couple of years back.

"Sounds fun," she beamed at Simon. "I'll do it if you go get it for me."

"Oh... I can't go in Jeanie's room. She'd kill me."

"She's not here, Simon. She'll never know."

But the young man shook his head while he wrung his hands. Ashley made herself give him a small smile and a pat on one sweaty forearm.

"Which room is hers?"

"First on the left," he mumbled, not meeting her gaze, as usual.

"Be right back," Ashley said in an airy voice that did not at all match her mood. She did not mind dressing up. Indeed, she hoped it might make what appeared to be a disaster in the making at least somewhat fun for her. But she could not escape the growing suspicion that nothing she did could save this 'date' from inevitable catastrophe.

The austere décor in Jeanie's room fit what little Ashley knew of Simon's older sister. Everything was neat and proper and boring. Crossing the sterile room, Ashley resisted the urge to see what might be in the dresser drawers. She found the costume hanging at the end of the closet and pulled it out. To her surprise, there was not very much costume to the costume. Ashley has expected a modern, more modest Wonder Woman outfit, but this one looked like the one from the 1980's TV series.

The brunette stripped out of her blouse and jeans. She hesitated for a moment before taking off the hot pink bra that made her breasts appear a cup size larger than they really were. She would have liked to have that additional fullness for the costume, but the outfit had no shoulders, so the bra straps would show. So, she slid off the bra.

"Here goes nothing," Ashley sighed aloud, pulling on the costume, or at least trying to. It proved considerably tighter than she had expected, and she recalled again that Jeannie was a skinny girl. Peeling it off, the brunette found the tag and groaned. It was sized for a teen, not a woman. And although only eighteen, Ashley certainly had a woman's body.

"Fuck me," she said to the room before pushing her panties down and stepping out of them. Even their thin silk was too thick for her to be able to get the costume on over them.

This time, Ashley managed to wiggle the bottom of the costume up over her hips. The shiny, star-spangled material clung to her like a second skin, and a quick glance in a full-length mirror mounted confirmed her fear. Without panties, the costume created obvious camel toe between her legs.

"Fuck me," she said again, closing her eyes as she pulled the top of the costume up, holding the front with her left hand while trying to zip up the back with her right. She managed to pull the tab about half-way up, but she could not move it past there.

"Hey Simon, I need help."

Ashley walked to the door and turned her back to it. A few seconds later, she heard a sharp intake of breath behind her, and she knew that he must be looking at her bottom in the skintight outfit.

"Zip me up, please," she asked, sweeping her hair forward over one shoulder.

"Um, okay," Simon said, his voice low, almost hoarse. Ashely felt fumbling fingers on her back, and she sucked in a breath. Inch by inch, he worked the zipper up, and Ashley wondered if this is what a corset must feel like. She had wanted to buy one a few months back, but she knew her mother would not approve.

"Okay, thanks," she said when the ordeal was over. "I'll be there in a minute."

For a moment nothing happened, then she heard Simon shuffle from the room. Ashley took several test breaths to make sure she could still breath, then moved so she could look in the mirror.

"Fuck me," she said a third time, examining her reflection. The chest of the costume, which was designed to cup smaller breasts, crushed hers, pushing their top swell up into impressive cleavage that looked like it might spill out at any moment. Afraid to bend over, both from concern of splitting a seam as well as falling out, Ashley crouched down to pick up a bag that had been on the hanger with the costume. Inside she found bracelets, a black wig, a plastic gold tiara with a star on it, and a coil of yellow rope. She opted out of the black wig, even though her brown hair was considerably lighter. She did place the tiara on her head and snap the bracelets around her wrists. The coil of rope she hung from a small plastic hook sewn into the waist of the costume. And when she looked in the mirror, she sighed.

I look like street walker Wonder Woman,

Ashley told herself.

I just need a pair of red, high heeled boots.

Moving carefully, she went back to the closet. Sure enough, she found a pair of red boots. The heels were maybe three inches, so not that high, but she was sure they must have been for the costume because they matched nothing else in the closet.

"Oh, thank God," Ashley whispered out loud when she looked at the shoe size of the boots. They were a size too big for her, but she could deal with that. Her fear had been that they would be too small and she would have to endure her toes being smooshed up like her breasts were. The brunette sat on the bed, conscious of how the costume's middle section strained as she did so. Slowly, she drew on the boots then pushed herself to a standing position while trying to keep her abdomen as straight as possible.

She returned to in front of the mirror, and this time Ashley smiled. The boots completed the look, and had the costume not been a size or two too small for her, she thought she would have looked good. Perhaps she would find one that fit better and see if Corey might like her in it.

"Okay, can't stall any longer," she told her reflection. "Show time."

Putting some sway in her hips, Ashely strolled into the hall and headed for Simon's room. A black and white cat streaked past her, and she nearly tripped. A faint ripping sound reached her ears, and her fingers traced up the seam on her right side, finding a small hole. Trying not to breather too deeply, the young woman made her way the few feet her client's room. When she reached his doorway, Simon, who had been sitting on his bed, stumbled to his feet. His wide eyes roved up and down, and Ashley forced her biggest smile onto her face.

"What do you think?" she asked, performing a slow twirl in the doorway.

Inarticulate noises came from Simon's slack jaw as his breathing grew heavy. Still smiling, Ashely closed the distance between them, both excited and a little disgusted at the way he stared at her barely contained cleavage.

"Do you want Wonder Woman to be your first?"

Simon's face, which had been beet red, drained of color. His pale gray eyes met her gaze and held it for several seconds before he nodded.

"In the costume, I presume. Well, that'll be okay for the first part. It'll need to come off for the second, of course."

"I washed," he blurted, and Ashely narrowed her eyes as she processed the seeming non sequitur. "Like you said in the email. I took a long shower just before you got here."

"Oh. Well, good." Ashley patted his arm and watched as the muscles quivered beneath the surface at her touch. "So, I guess you're ready for Wonder Woman to suck your cock?"

"Uh... I... um... um..."

"Or maybe, you're a villain and you captured her lasso. It's magic, right? You could use it to make her give you a BJ."

Ashley knelt, taking care not to bend too much in the tight costume. Once in places, she held the coiled rope out to Simon. The young man took it but did nothing else except stare down at her. Ashley made herself not roll her eyes. Instead, she clamped her arms to her side.

"Put the lasso over my shoulders, then slide it down and tighten it under my boobs. That'll trap my arms too."

His hands shaking, Simon followed her instructions, although she noticed he was careful not to touch her breasts. Had her arms been free, she might have smashed his hand against her chest.

"Okay, now pull your pants down."

"Yeah... yeah..." Simon breathed, unbuckling his belt and shoving both his jeans and briefs down. His erection bounced free, and Ashley grinned up at him. He was about average size, at least from her experience, and nicely shaped. She preferred a bit more girth, but she had been with guys a lot thinner. With sudden hope that her earlier concerns about this 'date' turning into a disaster might not be accurate, Ashley let herself relax into the role she had chosen.

"I will never suck your filthy cock, Dr. Simon," she said, hoping her expression conveyed a mix of fear and unwanted desire.

"Um... I have bound by your magic lasso, Wonder Woman," Simon said, his voice unsteady and high-pitched. "You must obey my command."

"I will resist with all my Amazon might!"

Ashley squirmed, doing her best to give the appearance of trying to escape the lasso.

"You cannot resist, Princess." Simon's voice came out steadier but no lower, and Ashley suspected she would have to prompt him a bit more to get things going.

"I will never do what you want, like lick your hard, throbbing prick."

"Um... yes you will. Lick my... um... penis."

"I can't resist you," the brunette said, leaning forward and running her tongue up the underside of her pretend captor's shaft. Simon's body stiffened and a sound between a whimper and a moan came from above her. Ashley looked up and saw the young man's eyes were clamped shut. At the same moment, his penis twitched and a lower moan escaped his lips. Ashely drew back. However, a second too late, she realized she should have taken him into her mouth instead. Spurt after spurt of semen erupted from his erection, coating the brunette's face and upper chest in warm, sticky fluid.

Quickest yet

, Ashley thought as the last little bit dribbled out of Simon's already softening manhood. Her second client, a sweet, shy young man named Grant, had ejaculated unexpectedly moments after she started sucking him, but even that had taken longer than Simon.

"I.... I'm sorry," he stammered, and Ashely sighed.

"Take the lasso off, please."

"Oh, sure." And Ashley endured her client's fumbling as he loosened the rope and then pulled it up over her head.

"And help me up."

Simon held out his hand, and Ashley took it, drawing herself to her feet.

"I'm going to go clean this off," she said, trying to hold his elusive gaze. "Then we'll try again, okay?"

"Really? You're not mad?"

"No, I'm not mad," she said, rubbing his arm. "You're excited. But you need to tell me before you're going to come, okay? If I'd known, we wouldn't have such a mess now."

"Oh... sorry."

"Don't be sorry. It's okay. Really. You're not the first guy to get too excited and do that."

"But... girls don't like it... um... on their face. Except in porn."

"If I'm ready for it, I don't mind. But I need to be told first, okay?"

"Oh... um... sorry."

"No more sorries, Simon. Now, I got to go clean up. Unless you want me to let it dry. Do you want to make Wonder Woman suck you off again with your cum drying all over her face? It'd be pretty fucking naughty, huh?"