Moonlighting Pt. 01

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An innocent college student moonlights as a prostitute.
9.4k words
4.62
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Part 1 of the 3 part series

Updated 10/18/2022
Created 06/01/2010
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Chapter 1: The City of Angels

In the City of Angels, there is no such thing as weather. It's always the same. Everyday. It was six in the evening and the sun melted on the horizon, reflecting off every surface and window in downtown Los Angeles. The 405 and 101 were packed bumper to bumper with vehicles inching closer and closer to their valley homes. It was an Indian summer in southern California, and the heat was finally starting to get the best of people. Shop owners sprayed the sidewalks down in front of their stores and people near the Ocean piled into cars to spend the remaining hours of daylight cooling off in the icy cold Pacific Ocean. Punks and elderly citizens sat covered in sweat at bus stops in the inner city, panting like dogs as their respect buses came. It was over 100 degrees still, and the people without air-conditioning were most bitter of all.

It was going to be a long night.

As the sun finally set and bled into the inevitable twilight, Nick Palmer made his way through the traffic on a tightly configured and well-maintained mountain bike. His earbuds were in, a soothing trance song drowning out the ambient noise all around him. The cares of the day slipped away from him as he eventually broke away form Santa Monica Boulevard and took back roads the rest of the way home. He had just gotten out of his last class at Pepperdine and was making his way to his Westfield apartment. It wasn't anything special -- just a small 1 bedroom he was subletting for a year from some spoiled brats running around God knows where in Europe with their parents' credit cards.

Still, he couldn't complain. He kept the place clean and the location couldn't have been better. He was just a bike ride away from the airport, the beach, school, and a nice enough movie theater.

Nick was not a complex man, like most men. He was a nice guy, good-enough looking with a great body from biking everyday. He had short-cropped black hair he gelled up and a sort-of indie meets rock and roll look to him, but he never outdid himself. Jeans and some form-fitting dark tees defined his wardrobe and he was perfectly fine with that. They were comfortable and it was a look he felt comfortable with. He was an English major at Pepperdine -- a school he got into on the grace of a scholarship program he entered back in high school. He still had some expenses to pay out of pocket, but mostly he had made out with a pretty good thing since moving out to the west coast from Kentucky three years ago.

A car drove up a few blocks away from Nick's apartment building, downtown Century City and Beverly Hills looming up in the background against an ever-darkening sky. The car parked in a residential neighborhood outside of a very expensive home. The woman behind the wheel was a rail thin brunette with a rock-hard body. Her hair was cut short and styled over her heavy make-up. Her wardrobe was skimpy at best -- short, shorts -- an elaborately designed bra covered only by an unzipped vest-sweater. Her mascara accentuated her gorgeous eyes, and her choice of jewelry was spot on for the part -- she was a hooker.

Her name was Sierra Miller. At least that's what the ID in her back pocket said...

She went to the local coffee shop and was by now used to the raised brows and harsh stares. How dare she revert to this profession in 2010, seemed to be the consensus frustration by everybody who assumed the worst of her. It made no difference to her, in fact, she was glad. This was precisely the kind of situational hazard she was thirsty for. When she put on the clothes, she never broke character. The most devoted of method actors would have been blown away by her dedication and conviction.

Still, she was kind, gentle, and good with people. She was never rude. The girls behind the counter seemed to take a liking to her. Whether they felt sorry for her or not, she didn't care. If only they knew the truth. She took her coffee a couple of blocks down and met eyes with a bear of a man in a trashy outfit sitting outside of a closed electronics store -- this was Vinnie (the pimp). He was chatting up a couple of the other girls who all called and waved to Sierra enthusiastically.

"Hey," Vinnie said with a genuine smile on his face.

"Hey," replied Sierra, used to his rugged exterior by now. She handed a coffee to Vinnie and began to dispense the others to everyone around. They all had their poisons of choice, and Sierra had memorized them all. They all made chit chat and exchanged gossip for a little while longer. Sierra interacted occasionally, but was careful never to become the center of attention. She didn't want to taint the field by involving herself anymore than she already had to. She looked over and caught Vinnie staring down at her flat stomach. She was always complemented on it. In high school, an early friend had told her that it was one of her more attractive features and that she could appropriately exploit it without being called a slut.

Anyway, Sierra let Vinnie's look go unchallenged. For one, he was in charge. And secondly, as long as he kept his hands to himself, he could look all day and night for all she cared. But really, she knew Vinnie had a soft spot for her, and besides, he treated her well. Why shouldn't she let him steal a glance from time to time? It only made her feel sexier anyway. Too bad she wasn't permanent, Vinnie thought. You see, Sierra wasn't actually a hooker -- she was just playing one undercover.

No, she wasn't an undercover cop or a federal agent or anything like that. She was actually just a regular college girl from San Diego State doing a provocative sociological study on sexuality in regards to pornography and prostitution as it relates to the single male. Right now, she was writing a first-hand experience under an assumed name based on her experiences undercover as if she were interviewing a real-life informant who had wished to remain anonymous. What her colleagues would never know was that she was actually the informant.

She had literally split herself into two identities and was always careful to make sure they never intersected. That was all about to change tonight.

Vinnie had immediately thought her to be a cop when they first met, but she soon explained herself and promised that she would always buy the girls and him coffee every day. Vinnie couldn't argue with this and brought her on board as a sort of liaison who would only oversee business, but never participate. Vinnie quickly took a liking to her even though Sierra had expressly told him on day one that she would not be seeping with him under any condition. Vinnie was disappointed by this, but soon found that he only respected her and liked her all the more for being so up-front and stern with him. He wasn't used to being told what's what by the women in his life, quite the opposite actually.

Though she would never consider this man attractive in her other life, she could see the pull and allure of his charisma in this one. He was protective of his and his own and never made Sierra feel uncomfortable. He always stood up for her and even one time knocked a guy to the ground when he shoved Sierra up against a wall during a scuttle with one of the girls she had followed into an alley in hopes of witnessing her first public sex act. Unfortunately she only ended up nursing a strained wrist with a bag of frozen peas that night. The sex would eventually come, little by little, until she was finally asked to by Leila, one of the girls she befriended, to watch her fuck one of her regulars.

It was odd, at first, watching another couple go at it, but she quickly overcame her own embarrassment and was overcome by her own sexual curiosity which she felt had laid dormant for so long now.

She sat in the corner of a dark bedroom and watched her friend Leila, a pale redhead with naturally large breasts, stick another man's dick into her mouth and bob up and down on it. She watched her fuck him in every position possible, and even at one point, take it in her ass. Sierra's panties had soaked through at this point, but she swore she would never act on her own impulses... even if they were toward something as innocent as self-gratification. Masturbation would only add fuel to a dangerous fire burning wildly inside of her.

She just about exploded when she watched Leila clamber off the man and shove his dick back into her mouth just as he cried out and shot his load deep into Leila's throat. She swallowed every drop and that was that.

Ten minutes later they were taking the stairs back down to the lobby. She couldn't believe this girl did this with a different group of guys every night.

Now, Sierra was not a prude, but she wasn't all that experienced either. She had had sex a couple of times with a guy she liked back in high school, but didn't get much out of it and just never perused it since. Today she was following girls along -- actual hookers, and watching their experiences first hand. The deeply pornographic and degrading nature of what they would do both disgusted her and fascinated her. She saw past the degradation and realized quickly it was a mutually beneficial relationship -- assuming both parties were being safe and smart about it. Not to say that's all these girls wanted out of life, but for the time being, they made it work.

Sierra quickly became immune to it all and quickly realized she was masturbating much more frequently than before she had delved into this world. Her fantasies also transformed from PG-13 romps in the hay to NC-17 fuck-fests. She even bought a vibrator that she couldn't get enough of on some nights. But they were only ever fantasies still, safe areas she could quickly create or erase at the whim of a thought -- and she would never act on those fantasies or dare to mix business with pleasure.

Until Nick...

Chapter 2: The Dance

Sierra was standing on the corner, just inside the old electronic store that Vinnie ran in the day, still chatting up some of the girls. It was by now nighttime, some of the girls already noticeably missing from the crowd -- already hard at work behind closed doors.

She saw Nick bike up and park outside his apartment's main door across the street. Sierra moved quickly when she saw him. Vinnie watched her go and knew that sparks were flying in her head with this kid. He was nice enough, he thought. He had stopped in to buy a couple of batteries once, and a pair of headphones another time. Cordial. Polite. Paid in cash. He was the perfect customer. Not too many guys like him the neighborhood really. Plus, Vinnie would never let Sierra get mixed up with a lowlife. Long as he minded his manners with her, he was square with him talking to one of his girls off the clock.

Nick was fishing through his pockets for his keys under the streetlamp high above his head.

"Hey," Sierra said approaching from across the street. Nick turned and almost blushed at the sight of her. She was always dressed to kill and take names in the process.

"Hey," he smiled back, knowing his second-take on her outfit and body did not go unnoticed. She smiled and bit her lower lip at the thought of being instantly taken in and mind-fucked in less than a second. Hopefully the fantasy took longer than that though. Men's brains made little to no sense to her sometimes.

"You ever going to buy a car?" she toyed.

"If I ever bought a car, I wouldn't be home in time to see your pretty face," he shot back.

Nick was good enough with the ladies, but just independent enough that he didn't need one in his life right now. He had some favorite sites bookmarked online whenever the feeling got the best of him. He had had beautiful girls before too, but all nice small town girls back in Harlan County and Elizabethtown. Never in a million years would he have imagined himself to be so casually conversing with a hooker (or a girl he believed to be a hooker at least).

But he wasn't the judgmental type. She was nice enough to him, and he was always going to show her the same decency and respect in return.

"Is that right, babe?" she threw back. She loved giving him pet names because she knew he was not used to them.

Nick smiled. "So how are you?" he asked.

"Can't complain. How about yourself?"

"Oh, another day, another dollar," Nick replied.

"I hear ya."

Nick smiled uneasily and knelt down, pretending to busy himself by fixing an imaginary problem with his gears. It would be rude for him to leave mid-conversation, and he didn't want to shrug a beautiful woman away so quickly either.

"So when are you going to invite me up to your place?" Sierra asked with a devilish smile on her face.

Nick's cheeks flushed red and fueled an uncontrollable smile.

"When it's not so messy, I suppose."

"You used that excuse last week - and the week before that - oh, and the week before that too," she said, honestly recalling every time he had individually rejected her.

Nick just smiled again. "Well, I guess I better get on that. But I don't suppose it would help if I said I couldn't afford a pretty girl like yourself."

"It's never polite to discuss price with a lady Mr. Palmer," she stated, eyes wide and cheeks flushed. He immediately apologized but she quickly reminded him that she had only been teasing him.

Nick turned back to his chain. Sierra loved that she could never be the center of this guy's attention. At school, guys asked her out regularly. Not that she was one of the "popular" girls or part o a sorority where guys were throwing themselves at her, but she was a confident girl.

"Anyway, price shouldn't matter. I told you... the first taste is free..." she bit her lower lip and made sure Nick had seen this gesture. He nearly froze in place when he considered her words literally.

"I -- uh -- will consider that. Trust me. But I do have to go."

"Your loss."

"Yes, I suspect that it is..." Nick hot up and walked into his building finally, dragging his bike behind him. When he got inside, he exhaled heavily.

Sierra just stood her ground a moment longer, smiled at how she imagined Nick to look right now, turned on her heel, and crossed the street.

What she was trying to pry out of Nick was an understanding of the moral implications regarding prostitution when it came to regular men who didn't or wouldn't otherwise turn to woman like her (or the type of woman she was pretending to be). She thought it might be the price, but she clearly missed the mark there, as she still couldn't seduce him. She had then thought it might be a matter of cleanliness, so she immediately brought him an actual test-result for Nick one evening just to prove to him that she was clean as a whistle.

He just smiled and shrugged her off, even then. He offered up some uneasy playful banter on his way up to the apartment just like they had just done.

This was their dance.

She wasn't actually going to sleep with him, but she wanted it to get that far at least. She was convinced every guy had a reason, and Nick's was one she longed to have. Somehow, she would find a way to seduce him and answer an age-old question for her case study.

She was going to make Nick want to fuck her one way or the other...

Chapter 3: The Art Project

They had first met when Nick nearly ran her over one day as she stepped out from a blind corner by his apartment. He had been speeding down the sidewalk on his bicycle and nearly killed her and himself in the process. A couple of pedestrians who nearly got taken out in the process shouted some obscenities in the street.

"Asshole!"

"Jackass!"

Sierra, though, had been knocked flat on her butt and Nick thrown over his handlebars. A couple good Samaritans checked to see that he wasn't injured, but he just shrugged them off. Vinnie ran over after seeing the whole thing go down from his usual chair in front of the electronics store.

"Hey, asshole, you nearly killed my friend here!" he yelled down to Nick.

Sierra wasn't all too pleased with him either.

"Yes, sorry, sir -- it was all my fault. I really am sorry..."

Sierra and Vinnie were both stung by the 'sir' -- it was a habit he had formed long ago. It wasn't anything military related, just a since of cordiality his Aunt Sandy had instilled in him long ago as a boy. She had told him it would help ease the worst of situations and mostly she had been right. Including now.

Nick looked into Sierra's eyes. This whole incident had taken place only two weeks into her stint. She immediately saw an honest and genuine compassion in his eyes and knew immediately that she could not be angry with this boy. He, on the other hand, was immediately scared and intimidated by her. Being enveloped in Vinnie's shadow didn't help either. But she quickly forgave him and the two introduced themselves -- and that was the beginning.

--

Nearly six months later, Nick sat in front of the computer and watched old episodes of Breaking Bad online while eating a bowl of cereal. His completed homework was laid out on the rickety table in the kitchen. That was another bad habit of being raised by his Aunt Sandy -- work first, play later. But still, it had never been advice that got him into any sort of trouble. It always helped him avoid it.

His cell phone rang.

"Hello?"

"Hey -- is this Nick?" came a semi-familiar female voice.

"Yeah, who's this?"

"This is Amanda, I was going to model for you this weekend?"

"Was?" He recognized the girl's voice from his Art-242 class as the in-class model the class was to work with on an individual basis for a unique photography assignment due at the end of the week. Nick's time with her was scheduled for tomorrow morning.

"I just got a call back home, one of my cousins is in the hospital and she's not doing so well."

"Oh no, I hope she's alright?" he asked, genuinely concerned, already knowing he was screwed out of his grade.

"I hope so -- she was in a car accident and is pretty banged up, but I'm going to need to fly home and be with my family is the thing..."

"Of course, don't worry about it."

"Are you sure?"

"Yes, of course. Don't worry. Go."

"Okay. Thanks!"

"No worries, we'll figure it out later."

And with that, the line went dead.

"Shit..." he thought.

He had just borrowed a really nice camera and some small lights from his friend Jim in the photography department to take these pictures. The assignment was to take photos of this particular, the same model everyone in class was going to be taking photos of -- and then compare all the photos in regards to what people thought was erotica. It was also going to be an assignment going on display in the new art hall that had just been finished a few weeks ago at the end of summer. He knew many important people would be looking at these photos and wished more than anything that he was able to get something in there.

Photography was a hobby of his after all.

Nick quickly made a call to his professor who was already aware of the situation and assured him his grade was not going to suffer. The professor said he would still accept photos of a different model so long as he remained on point. He said he would attempt to find a last minute replacement, but knew that would be next to impossible with a beautiful woman on a Friday night.

But then a dim light clicked on in his head.

Nick walked over to his window. He pulled the shades aside and was looking four stories down on Vinnie chatting with some random guy, presumably a friend of his.

Moments later, Nick crossed the street and met eyes with Vinnie. He finally approached him.

"Hey man," he said.

"Hey," Vinnie came back, the other man with him looking at him just as curiously as Vinnie.

"Uh, is Sierra around?"

"She's with a client." Vinnie stated sternly.

"Oh, okay." Nick nodded, and turned back.