Press Your Luck 36 (Patreon)

Monday evening Harlow returned to the casino, stepping into the building felt like returning home. With the lights and sounds, the sight of people with as many emotions as there were colors as they gambled, won and lost.  That morning he had been practically beside himself with excitement at the idea of making his own money so he could fix things and do it all while being at a casino just felt like serendipity. Harlow hadn’t even considered the fact that he would be wearing a uniform and had changed his mind on what to wear several times before heading out. His new boss Carl wasn’t exactly an impressive man, it felt like a shame what he had to do with him to get the job and an even bigger shame that the man had left him unsatisfied. Carl had said he would get to be where the high rollers were, but he was willing to bet that would only stay true if he was kept happy. Looking at himself in the cheap motel mirror he saw Lucy’s smile as she gave herself a wink. The outfit she had decided on was a black pleated miniskirt, black opaque thigh high stockings, a pair of five inch pointed toe stiletto heels and then lastly she added a black three quarter sleeve bolero jacket, deciding the tube top wasn’t classy enough.

She was all smiles when she met Carl, a small pout forming on her face as he seemed mostly dismissive, seemingly looking anywhere other than at her, a direct contrast from every other man she had passed on the way to his office. Carl brought Harlow into a rectangular room with a row of ten lockers and a singular bench that acted as the changing room and introduced him to a tall pretty woman in her mid-thirties, the faintest hint of a wrinkle around her hazel eyes covered by foundation and concealer something Harlow wouldn’t have noticed only a few months ago and would have assumed she was ten years younger. Her wavy black hair fell over her shoulders contrasting the gold bustier corset. A black leather miniskirt clung tightly to her wide hips, exposing just the slightest hint of the lace tops of her black stockings. Taking her in, Harlow realized the woman wasn’t as tall as she first appeared, but rather, wore six inch platform stilettos.

Carl motioned his hand in the woman’s direction as he spoke. “One of my olde–” Dianna loudly cleared her throat, fixing the balding man with a glare, causing his words to stumble as he tried to correct himself. “Dianna is our most seni–” Another glare from Dianna stopped the word in his throat–“she’s my head waitress.”

“I thought that was our little secret, Carl?” She said with a playful smirk.

“Ah geeze.” Carl ran his hand through what remained of his hair, a blush filling his cheeks as he glanced at Harlow, “Dianna, this is Lucy. Lucy, Dianna. You’ll report to her. I’m gonna…yeah.” He turned away from the two women and retreated to the safety of his office leaving Lucy alone with Dianna.

“He’s fun.” Dianna giggled.

“Y-yeah.” Harlow giggled back, “He seems, kinda…”

“Too shy to boss around a bunch of half naked women?”

“Uh…yeah.”

“He’s a teddy bear but he’s always putting himself down, I think cause of his weight, so I like to boost his ego a bit. Plus, it’s just fun.” Her smile wavered for a moment, before it snapped back into place, “Speaking of half naked; let’s get you into uniform.” She turned and pulled a box off of the metal shelf beside the sink, “This…yeah, this should fit you.” She pulled out a gold corset bustier identical to her own and handed it to Harlow before turning back to the box. “You’ll have to leave your clothes here, your stockings are fine. Ah here.” She turned around and handed Harlow a black leather miniskirt, “Do you have higher heels?”

“A couple.”

“If they’re black or gold, wear them tomorrow. The higher the heel, the higher the tips.” She said, holding her heeled foot to the side as she continued. “If you lose the stockings you will too but your cute little legs will be icicles within the hour. Though we all freeze at least a little with our uniforms.” Dianna winked.

After changing into his uniform and placing his clothes in an unoccupied locker Harlow began his first day as a waitress, Dianna giving him a brief introduction to a man in a black button up and sparkling gold bowtie who tended bar before giving him a run down of the cocktails they offered. “Have you ever tended bar before?”

“No? This is, like, my first job.” He said with a confused pout, “But, like, I thought I was just gonna be a waitress?” The sound of one of the slot machines hitting a jackpot rang out in the distance, pulling Harlow’s attention away. He wasn’t much for slot machines, he wasn’t one for work either. He had made it just fine… mostly fine with playing the tables. His mind started to wander thinking of the things he absolutely needed to get with his first paycheck and how much he could grow at the tables, but he didn’t get much farther than knowing he had to reinvest in himself, the cost of a long overdue mani pedi, getting his hair done, when he realized Dianna was still talking to him.

“First off I just wanna say I love your voice. You sound like Marilyn!” She giggled. Harlow couldn’t help but giggle along with her, he had not spoken in his own voice in so long that he almost forgot that how he spoke now wasn’t really him, “How to marry a millionaire was my favorite movie.” Dianna added, “But anyway,” She waved her hand, her bangle bracelets jiggling as she did so, “Sometimes Chris will be too busy to make the drinks for you, especially on weekends, so you’ll have to make them yourself or you’ll risk losing your tip. And in the high roller sections that could be double digits.”

“Oh.”

“Don’t worry, after a while it’ll be second nature and they have cards telling you how to make everything. C’mon.” She placed a hand on Harlow’s bare shoulder, turning him around and guiding him to the high roller rooms. Harlow was all smiles returning to the quieter high rollers room. This was where he truly belonged. Even if he was currently dressed just shy of a stripper.

The first few hours were easy enough, the hardest part was remembering the drink orders of an entire table. But as the night progressed the patrons became drunker and more emboldened by their alcohol. At first he didn’t mind the flirtations, in fact he was finding he enjoyed the attention as they called him “cutie” or “beautiful” when they thanked him, the tips certainly helped, but when the first drunken patron reached out and pinched his ass he couldn’t help but yelp in surprise. When he whipped around to see who had done it, he was surprised to find a woman. Confused and unsure what to say or do, he did as Valerie had taught him, he giggled and smiled.

By the end of the first night he had been pulled into three different men’s laps or to their sides who all insisted he was their good luck charm. He didn’t mind too much since it gave his legs a rest and being called Lucky Lucy once again gave him a warm feeling inside. Harlow imagined he must have walked twenty miles before his dinner break. The shift had left his feet sore and his whole body freezing. He thought his bolero jacket would look cute with the gold and black corset, but none of the other girls were wearing something to keep themselves warm. Though he did see one girl wearing block heels, a contrast to Dianna’s stilettos, though Harlow knew from experience the two inch platform on her shoes helped with their height. It was when they would let their hands roam and grope his hips that he had to make excuses to leave.

Being touched and wanted by so many men and a surprising number of women reminded Harlow of just how desperate he was becoming. He tried once more to jerk himself off once he got home, only to leave himself limp and more worked up than before and cursing Valerie! Unaware that the chip implanted under his arm was pumping estrogen and spironolactone into his bloodstream, further feminizing the already feminized man every day. The major effect of course being reducing his penis in size and causing impotence. But, Harlow didn’t know any of this. All he knew was it was impossible to get a hot shower in the motel and it turned out to be a blessing in disguise as the next few days wore on and the groping continued.

Standing in an empty corner behind the bar one late evening Harlow counted the meager tips he collected midway through a grueling shift. “Better hurry up, Luce.” Dianna said as she walked around the bar and stood beside Harlow, “If you don’t go on break soon Carl’s gonna put you back to work.”

“I am. I just gotta count my tips.”  He said without taking his eyes off his money and mouthing the numbers as he counted. Some of what he had earned was in cash and others some of the casino’s poker chips.

The older black haired waitress bent over the counter, placing her cleavage on display for any of the customers who came by but she didn’t care. She had a huge grin on her face as she started, “Three, forty-seven, six, one hundred and twelve, thirty-tw–”

“Cut that out!” Harlow slapped Dianna with a handful of cash, “You’re, like, so mean.”

“I’m only teasing.” She laughed, holding her arms up in surrender.

“I know.” He sighed, “You’re still mean.” Harlow bit his bottom lip and groaned as he scooped up the crumpled bills and started over.

“Want me to help?”

“I can count.” Harlow snapped defensively, “It’s just been, like, a rough day. Between rent, being on my feet all day, and every horny drunk from here to Atlantic City pinching my ass I totally get why Carl has a hard time keeping girls.”

Wrapping an arm around Harlow’s bare shoulder she pulled the feminized man into a half hug “It can be tough, I know. But it’ll get easier over time, and unless you want to take up dancing and really have to deal with groping…” Dianna put one finger on a fifty dollar poker chip. “You aren’t going to be getting much of these.” The older woman looked over her shoulder and off into the distance. “I know Racheal, who is handling drinks in the slots area today, would trade with you in a heartbeat. Dianna said gently, giving Lucy’s shoulder another squeeze.

Harlow glanced at the hand on his shoulder with a small pout. At least she had someone to go home too. Harlow had been living mostly alone with his mother before his escape from Marcus and Oswald. ‘God that, like, feels so long ago.’ They were hardly ever home at the same time but it was nice knowing she was there. Living with Daniel…and even Valerie was even better but now his mother was gone and he was thrown away and discarded by Valerie and Daniel. He was alone. “At least…at least you have that to protect you.” He said with a gesture to the ring rather than what he really thought.

“Oh this.” She pulled away from Harlow to hold the ring up to the light with a smile, “It does really do a good job keeping most of these losers at bay.” She paused to look at Harlow before continuing, “That’s the thing, I don’t have a fiance. I wear this beautiful bauble to keep the men away. Unless they’re really cute.” She laughed, bumping her hip into Harlow’s as she winked.  “You should definitely get yourself one.”

“I can barely afford food and rent.”

“Pawn shops have hundreds of them, you just gotta find you one that fits. And if not I got a pair of pliers and a blowtorch.” Harlow’s eyes widened, imagining the cackling Dianna wielding a torch with a bright blue flame and coming towards his delicate fingers. The older woman smirked, almost as if she was reading Lucy’s mind, “For the ring.”

“Oh.” Harlow giggled anxiously even as he still rubbed his fingers protectively.

“Think about it.” Dianna said, picking up a tray, “I gotta get back to work.”

[

That night continued on, and Dianna’s suggestion turned over and over in his head as he was delivering another round of drinks to the high rollers. When a drunk man grabbed Harlow’s wrist and pulled the feminine man to his side. “Lucky Lucy!” The gray haired man laughed at her nickname. “Need you to blow me, baby.” He held up the green dice to Harlow’s lips, nearly shoving them into his mouth as he swayed beside Harlow. Rolling his eyes he blew on the dice. “Yeah, just like that.” He laughed again before shaking the dice in a jerking motion and tossing the dice onto the table. The dice bounced around the table until they landed on five and five.

“Ten the hard way.” The dealer said as members of the table cheered in excitement.

The drunken man squeezed Harlow tighter to him, “I lost the three rolls in a row because you weren’t there to blow me.”

“That stinks.” Harlow said with a vapid smile on his face, trying to resist the urge to roll his eyes.

“I forgive you since you just won me ten times what I lost.” The man laughed as he collected his winnings.

“Lucky me.” Harlow said sarcastically, taking the man’s momentary distraction to walk away from the table.

Before he could reach the door Harlow heard the drunk man’s voice again, “Hold on now,” He said cheerfully, holding up a fifty dollar chip, “This here is for you.” He said. Harlow was about to thank the man when he suddenly slipped it between his breasts. The man continued as Harlow just stared in stunned silence at the chip sticking out of his cleavage, “I have not been able to stop thinking about you since I heard your voice.”

Harlow giggled uncomfortably, “Thanks, I had to practice it a lot.”

The drunk man laughed at what he assumed was a joke. “But, I would rather hear that sexy voice of yours moaning with my cock in your mouth.” He said as he gave her ass a squeeze.

“I, like, couldn’t do that.” Harlow giggled nervously as he looked around, hoping someone would notice what the drunk man was doing but everyone was too focused on their gambling to see.

“How about now?” He asked, slipping another chip between Harlow’s breasts.

“I don’t do that.”

“Here.” He said with a soft growl as he took a hold of her wrist and placed another chip in Lucy’s hand.

“Look,” Lucy said forcefully, “I said it’s not going to happen.” she stopped as she caught sight of the chip in her hand. It wasn’t another fifty dollar chip but a hundred, which matched the second chip he had slipped in between her breasts like some flesh doll slot machine.

“Yeah, I thought that might change your mind.”

Lucy paused and bit her lip, she could really use the money. The job itself didn’t pay much, but this man’s tip  alone would get her a week in the motel. With a pout she passed the chip back to the man, “I told you I don’t do that sort of thing.”

The man glared at the sexy redhead, his happy tone vanishing as he spoke, “Then how about I tell your boss about your little side hustle.”

“What s–”

“Prostitution outside of a certified brothel is illegal, even in Las Vegas, little girl.”

“I’m not a–”

“If your boss doesn’t fire you he could lose his job, the casino could be fined. I doubt the casino wants the scandal.” The man gave the red headed girl in front of him a smirk, he knew the game. He came out here twice a year, and the last trip they not only comped him his room after how much he spent, but when he requested a girl to keep him company a little blonde in the same uniform Lucy wore had been sent.

“But you–”

“Of course, you could be smart for once and just do what I paid you to do and everyone gets to walk away happy and gainfully employed.”

Lucy bit her bottom lip again, as her eyes darted around the room, Carl would never…he might believe the man considering how she got the job but he was a good man and probably wouldn’t fire her. Which would mean he would lose his job with the casino and Lucy would be fired anyway! And then what about the other girls who worked for Carl? If they didn’t lose their jobs along with him they might get a boss who did take advantage of them. She imagined the gray haired old man whipping Dianna as two waitresses served at his feet in nothing but heels and thongs. Her mind’s thoughts picking up its pace with every beat of her heart as panic started to grip her. Every thought making things feel grimmer if she didn’t comply.

Could she really risk all of that? ‘It’s not like cum is that bad anyway.’ She thought, “Fine.” She said, holding out her hand for the chip. The ugly gray haired man sneered and placed the chip in her hand as he led her out of the high rollers room and into the nearest bathroom.

]

The next evening, Harlow arrived at work and after changing into his uniform he took the little ring out of its box with a smile, ‘Daniel may not be here himself but, like, he’ll still be protecting me from jerks.’ He thought as he slipped the finger on his right hand ring finger. After the relative success of the previous evening he went out to a pawn shop first thing that afternoon to buy his own fake engagement ring, after washing and styling his hair and doing his makeup of course. Harlow knew shops would pawn anything in Vegas, but the number of rings was more than a little surprising. The hardest part was finding a ring in his size that he could afford.

Harlow stared at the ring, twisting it around his finger as he thought about Daniel. Until he caught a glimpse of himself in the mirror. “Oh? You wanna grab my butt?” He asked his reflection, “WAPOW!” Harlow exclaimed, flicking his ring finger at his reflection, “No can do! I have a fiance.” he giggled. “Wasat?” he asked, turning his ear towards the imaginary customer in the mirror, “Nice rack? Yeah my fiance thinks so too!” He held his hand to his exposed cleavage, putting the ring in the eyeline of the fictitious asker. “Now run along before I show you how much a karat hurts!” He moved his hand suddenly as if he were about to backhand someone. “Bluh!” Again he giggled at his own silliness. “Dinner?” He asked his reflection again, “Sorry.” he pouted, elongating his phony apology to himself, “I have a fiance.” this time he held up gently to display the ring “His name?” His reflection asked, “His name’s Daniel.” He felt his lips curl into a smile, “Oh he’s, like, totally handsome.” He paused, staring at the ring, “And sweet.” The smile on his face slowly began to fade as he twisted the ring on his finger, “I, like,....”

“Alright, enough of that.” Dianna’s voice said suddenly to her right as she closed the door behind her.

“Hey!” Harlow squealed in fright, “When-w-how long…like how long have you been there?”

“Somewhere around grabbing your butt and…‘Wapow’?”

“Ugh!” Harlow groaned, “You’re kidding me!” he whined.

“Please, I’ve caught girls doing a lot more embarrassing things in here than that. Though that is up there.” She smirked, “Let me see the ring.” Her smirk quickly dropped when Harlow raised his right hand, “Good cut, nice color, but Luce…engagement rings go on your left hand.”

“Oh.” Harlow pouted now having a new reason to be embarrassed.

“You’re fine, it’s a common mistake.” Dianna waved the pouty girl’s sadness away as she slipped the ring off and held Harlow’s left hand, “Lucy?” She asked softly, her voice steady and serious, “Will you marry me?”

Harlow rolled his eyes, his smile faintly returning to his face, “Just gimme my ring.”

“Fine, but I aint signin no prenup.” She groaned as she slipped the ring onto Harlow’s finger. “There. Perfect.” She smiled at the younger girl.

“Really? Cause when I pictured this day I pictured harps and doves, and a ten gallon hat filled with margaritas.”

“I’ll get you a bourbon at the end of shift.” Dianna waved the girl off again, and opened the door, “Now come on, there’s drunk men out there begging for what they can’t have.”

“That’s right, I’m off the market now!” Harlow adjusted his breasts in the corset, “Time to break some hearts and like make some money” He giggled as he walked out ahead of Dianna.

Things started to get easier as Harlow got used to the job, it felt nice to feel appreciated and being allowed to get a plate of food from the buffet with each shift had helped to alleviate the hunger pains he had been dealing with since he had been kicked out. Some men didn’t care one way or the other about the ring on his finger, but it did make life easier in terms of the amount of men who hit on the engaged Harlow. There were still the few men and women who grabbed him and insisted he stand with them as their good luck charm, but that was just part of the job he had learned, though from his experiences in the casinos he should have already known that lesson, things were just different on this side of things.

One late evening, or morning in this case, Harlow sat at the bar and ordered a rum punch before laying his head on the bar with a heavy groan. “Just getting started or just getting off?” a familiar feminine voice asked.

Harlow looked to his right through his long red hair that had fallen over his eyes and found a beautiful freckled redhead at the furthermost corner of the bar. “Uh…like, just getting off.” He giggled nervously.

“Same here, mind if I join you?” She asked with a bright smile.

“S-Sure.” He tried to reflect her own smile back as he sat up, frantically fixing his hair and checking his makeup in the mirror at the back of the bar.

“I’m Candy.” She introduced herself as she moved to the stool beside Harlow.

“L-Lucy.” He shook her offered hand, swallowing hard as he took the woman in.

“It’s a pleasure, Lucy.” She smiled and Harlow felt his trapped member twitch in the gel of the prosthetic that trapped his member. Candy took a second and studied the cocktail waitress and Harlow felt his heart clinch in his chest, “I’m sorry. I don’t mean to stare.”

Harlow giggled nervously, “You’re, like, totally fine.” He wasn’t feeling fine though, he recognized the freckled girl, he had paid for her company more than once. Now she didn’t see him as a man, a girl he had slept with only saw him as a female. ‘Please don’t recognize me, please don’t… ‘

“You’re not half bad yourself.” Candy laughed and took a sip of her drink, “So, what’s got such a pretty girl so down?”

“How much time you got?” He asked as he took a sip from his glass. ‘Why did I say that!? She needs to go, I need to go before she figures out who I am.’

“Well I usually charge four hundred for an hour.” She shrugged. “But since you’re cute and you look like you had a rough night already, we’ll do this one for free.” Candy giggled. Harlow coughed, half shocked by her openness, half reflexively giggling back at her as she flirted with him, or at least he felt like she was. “You okay?!” Candy asked with a raised eyebrow.

“I’m fine!” He giggled still, “Just…,like, it went the wrong way.” He took a deep breath before knocking back half his drink. ‘She said I’m cute, does that mean she likes me? She said free, is this going somewhere? Be cool, girl, be cool.’

The two spent the better part of an hour talking about their respective evenings, which consisted of complaining about customers. It was a surreal and terrifying experience talking to someone he not only already knew but had slept with, it was a blessing she didn’t seem to recognize him now. But that didn’t make his breath any easier to catch with every pause in conversation or lingering look, each making him think she was about to out him right there and then or invite him back up to her room

“That’s terrible.” Candy laughed, “I’m sorry I shouldn’t laugh the amount of times I’ve had my ass pinched.” She rolled her eyes. “Or slapped. But pouring the drinks right on him was great!” She continued to giggle.

“It was an accident!” Harlow giggled along with her, “I swear. Mostly.” He giggled more mischievously. It had felt good, though it was a bit undercut when he had to bring the guy another drink, this one with top shelf booze in way of an apology from the casino.

“Oh obviously it was an accident. Mostly.” Candy winked.

“But he was better than some at least.” Harlow couldn’t help but think back to the older man who insisted on buying a blowjob from him. The money was good enough to get him the cheap engagement ring.. ‘Pay attention girls, blow the right man and you too can get a ring.’ Harlow giggled at his own joke.

“I know what you mean.” Candy nodded, glancing at the ring on Lucy’s finger, “But at least you have a good guy or girl to go home to.”

Harlow paused, before remembering the ring on his finger. “Oh, this.” He smiled awkwardly, adjusting the ring that was just good enough quality to not leave a green ring on his skin.“I actually got this to stop the guys from pawing at me.”

“Has it helped?”

“Mostly, some” Harlow gave a small shrug of his shoulders. “Depends on the guy.”

Candy nodded, “I figured. Most people will respect the ring but there are some men who’ll view you as a challenge. As if stealing you from another man somehow makes them more of a man.”

Harlow immediately thought of Harry and the stories Daniel had told him, “I think I know a guy like that.”

“It’s pathetic really.” The freckled girl giggled as she took a sip of her drink.

“It really is.” He giggled back. “But, like,–” Harlow’s smile turned into a pout–“I get less in tips too which stinks cause, like, the manager at my motel told me this morning they’re going up in rent and it was already totally hard enough to pay rent.” Harlow stared at the dregs of his drink considering ordering another and spending the rest of his week in the motel curled up inside a bottle. He was already in the cheapest motel in town, the only thing cheaper was living in a tent. ‘I don’t even, like, remember how to set up a tent.’ he thought. The last time he had been in a tent was when his mother had taken them both out of the city and into the desert to watch the stars light up the night sky. He loved staring at the stars with her, making smores and listening to the quiet. She said it was important he knew there was beauty beyond the strip and took him out to their little camping spot every few months. Maybe if he had listened to her more he wouldn’t be in the position he was now. Eight days from being homeless, less than a hundred dollars to his name, and all alone.

Harlow jumped slightly when he felt the warm arm wrap around his still bare shoulders. He felt the corners of his lips tug into a small smile as he looked up at her beautiful face. Looking at her freckles reminded him of looking up into that star-filled sky with his mother. Harlow let the smile come as he leaned into her. He had hired Candy more than once because she was a sexy woman with a beautiful smile and didn’t think much about her beyond that. But there was something in the way they talked and how she held him that his mind insisted she was a kind person as well.

They sat in silence for the next couple of minutes before Candy spoke again. “You know,” She started softly,  “if you ever want to make some more money on the side, I know a couple of clients who would just love you.”

“I don’t know…” He hesitated as he pulled away from her warmth, wanting to tell Candy he couldn’t imagine himself having sex with someone for money, but he had done so twice now. Three if he included Carl but that was just a bit of oral to get a job.

“I don’t wanna force you. I know even in Vegas people still have a puritanical view of what I do.” Candy paused, seeing Lucy pouting again. The girl was sweet but obviously not the brightest of bulbs, “It’s not as bad as people think though. I can make about five hundred dollars for an hour’s work. Sometimes less, but never less than two fifty. Those aren’t the most…fulfilling guys of course but–” she shrugged–“ that’s why god invented vibrators, right?” She giggled, bumping the other redhead at her side with her shoulder. “Here, why don’t you take my card?”

Harlow looked down at the paper rectangle in his hand, the paper of the business card was almost silky smooth with his high gloss finish. He read it aloud “Rose Event Staffing.” When he saw the name on the card he looked up at the girl. “Rosemarie Edwards?”

Candy smiled, giving the girl a small nod. “My government name, I go by Candy when I work. Though I’m working on changing roles to work more in management. Maybe you can be the next Candy.” She said with a smile, positive that if she didn’t close the deal with the girl now, she would be calling her before a full day had passed.