Press Your Luck 35

By selling his plasma twice weekly and with some creative budgeting, and stretching of what defines “a meal”, Harlow was able to stay in the motel for nearly a month. As he got into the Uber  he happily greeted the familiar driver. "Heya, Jace!"

"Hi, Lucy." Jason said back with just as much cheer as he greeted his regular with a happy smile, "Someone's in a good mood tonight."

"Mhm," he hummed as he squirmed playfully in the front seat, "I, like, totally got a raise for being a regular! So, like, I'll be getting forty more dollars every time!" Harlow bounced excitedly while clapping his hands with joy. Fully aware that the man beside him stared at him with lust in his eyes.

"Speaking of; did I tell you I needed to increase my fee?"

"You're kidding!" Harlow stared at Jason in disbelief as his mouth hung open. Jason couldn't hold it longer and burst into laughter. "OH MAH GAWDUH!" Harlow giggled and slapped Jason's shoulder, “You’re such a dick!”. Harlow knew Jason wanted him but was either too shy or too scared of being shot down and making things awkward and losing a regular at the same time.

"But no seriously, this is a cause for celebration." Jason started the celebration by playing a song by Taylor Swift. The girl beside him rolled her eyes as she checked her phone but after a few quick texts back and forth to someone she joined in with the chorus. Jason still couldn’t figure out how she, or any girl, could text with nails as long as hers but somehow she managed.

As confused as he was he certainly was not going to complain about the dark red polish she had meticulously applied to her fingers to match the long sleeve crushed velvet crop top she wore. While her black high heels matched the black leather mini skirt. Try as he might to keep his eyes on the road while Lucy sang along happily with Katy Perry he could not keep his eyes off of her legs as they rubbed against one another, no doubt to warm herself against the cold night air she had just stepped out from. Jason knew from bitter experience not to ask why she didn’t dress more conservatively for the cold nights when she was always complaining about it being cold. He just turned the heat up and kept driving. Enjoying the mini-concert she put on for him.

The bubblegum pop assault continued until Jason pulled into the motel parking lot. Harlow hadn’t been a fan of “girly music” as he used to call it but that seemed to be the only type of music he found on the online high heel dance classes he had been forced to take part in. The one good thing about being…about leaving Danny’s was he didn’t have to keep up with that nonsense anymore. But it had left an unfortunate mark on him as he now knew so many pop songs word for word.

Harlow climbed out of the passenger seat, hurrying in the chilly night air to the driver’s side window and sticking his head inside for the last bit of warmth he could get before he’d have to make the run to his room. “Thank you so much for the ride!” He cheered, instinctually giving the sweet guy a hug before feeling the cold wind against his exposed butt. Saying their goodbyes as he stood he tried not to think about the show he was giving passersby as he bent at the waist to give Jason the hug. The act had become so commonplace for him it took a greater deal of focus and effort than he was currently capable of after donating so much plasma.

The short walk through the motel was another thing that had become second nature to him now to the point he no longer thought about it as he walked the path. Instead, like always, he was texting. Most nights he was texting Elana who would either update him on the latest gossip at her school, if not that then she was inviting him out to another club, or worse she would ask about how things were going between her and Daniel. Even though they had stayed in contact with each other, Harlow and Daniel hadn’t seen each other in the weeks since he moved out. Likely due to Vanessa. It was hard enough for Harlow to explain to himself, let alone a teenage girl who thought life was a romcom with a happy ending. Tonight he had told her the good news about his small raise in pay and she of course immediately insisted they go shopping and buy an entire cosmetic line released by some youtube star he had never even heard of. ‘First thing I’m totally going to buy is going to be a decent pair of pants!’ He giggled excitedly, ‘Maybe jeans! And a shirt with sleeves!’ He was still Lucy, but that didn’t mean she couldn’t wear pants and not freeze her ass off anytime he went to the store. He would have to count up all his money but he could possibly afford one or the other, possibly both, if he missed a meal or two. He would first have to do laundry again. He had plenty of clothes, but few were good enough to keep him warm against the cold desert nights. ‘I wonder if Elana’s ever, like, been to a thrift store?’ The thought of how she might react caused him to giggle again.

As happy as he was he didn’t notice the extra wiggle he put into his step as he continued texting Elana. Passing under the stairwell Harlow also didn’t notice the man sneaking up behind him until he felt an arm suddenly wrap around his throat and a hand grab his left hand, sending the phone skidding to the stone floor. “Hand over your take!” The man growled deeply.

“M-what?!” Harlow’s shriek came out more as a choke as he tried in vain to pull the arm away from his throat, only for the arm to tighten even more, cutting off his oxygen and snuffing out any resistance the feminized man had in him.

“Your purse you stupid bitch.” The arm squeezed around Harlow’s throat, “Drop it or I drop you!” The unknown man growled even deeper as his arm somehow tightened further. With the shifting of the arm, not only could Harlow not breath, the already dimly lit stairwell was beginning to darken even more. With no other choice Harlow pulled at the strap on his shoulder, letting it fall free to the stone floor. “I wasn’t being literal you…” with a heavy shove the man sent Harlow to the floor several feet away.

The man hurried to pick up the purse as Harlow coughed and gasped for air on his now skinned knees. “P-please!” He begged between gasps of air, “I-I need that money!”

“Everybody’s got problems, toots.” he laughed as he stashed the purse into a pocket inside his coat and turned to leave.

“Please. I’ll-I’ll do anything.”

The man stopped and turned back to Harlow, “Really?” Even in the dark and through his blurry tear stained vision he could see the masked man’s smirking face as he approached. The man ran his hand through Harlow’s hair before grabbing Harlow’s chin in his hand, “You know, I’ve never been with a ginger.” He laughed. Instinctually Harlow pulled away, “Tch.” he scoffed, “Next time then.” He shrugged and shoved Harlow away again before leaving, “Don’t worry the night is young, you’ll make it up on your knees in no time.” He chuckled as he rushed off into the night.

Harlow sat on the dirty stone floor for what seemed like hours before he finally picked himself and his phone up off of the stone floor and carried himself back to his apartment. He stuffed down the shame and forced himself to move forward. To his credit he made it into his motel room without breaking down. Before he even thought to tend to his wounds he opened the top drawer under the small bolted down television and pushed his panties aside until he found the small clutch purse he had hidden specifically to protect the money he earned and would use to pay for another week in the rundown motel.

The purse was empty. But he already knew it would be. He had foolishly purchased food that morning, expecting the pay from the blood bank to be enough that he could pay the motel the next morning. He had tried so hard to stay positive even when his life was crumbling around him, or at least to not let himself drown in the miserable reality he found himself in but life had once again kicked him in his tucked away giblets and even laughed as his money was stolen. It was then that Harlow finally broke down and cried onto the uncomfortable bed. And soon he would lose even that!

He had let himself forget…or maybe he wanted to forget that he was a wanted man. He let his guard down and life reminded him why he should never do such a foolish thing! He did nothing to fight back or get away and worst of all the man didn’t even pull a gun. ‘God I’m pathetic.’ he thought as the tears continued to stream down his face. No he was never a fighter like Daniel, or his father, or even capable of throwing a punch without hurting himself but…he had been better at talking himself out of situations worse than that! But lately…it was just so hard to think. It must be from being lightheaded after giving blood and plasma multiple times a week. He should’ve been able to stop it from happening.

As his sobs slowly subsided he took stock of his situation in the silence of the small single room. Every day he delayed payment they would add another thirty-five dollars onto his next bill. If it wasn’t paid in full after a week they would kick him to the curb! If he didn’t go willingly they had no trouble calling the cops either. A sight he had seen on more than one occasion. He scrounged the entire room in all of his various purses and found all the discarded change and bills he could. Whenever she got change from something his mother had a habit of leaving it in whatever jacket or pocket she had been wearing at the time, “I’ll find it sooner or later,” She told him one day, “maybe on a bad day and it’ll be a nice surprise to cheer me right up.” It had become a habit Harlow had picked up over the years for similar reasons as well. Right now he needed that nice surprise more than anything. But since he didn’t have anything with pockets, that meant purses he had left scattered around the room. His mother was right though, finding that first bill inside the third purse he looked through was a nice surprise that lit a tiny spark of cheer inside of him. For a second he wondered how his mom would react if she knew Lucy had more purses at one time than she had in her entire life. Not wanting to dwell on that he continued his search.

After throwing the seventh purse onto his bed he no longer felt the initial spark of cheer as he counted all the money he could find. Even after turning out all of his socks and drawers it wasn’t even enough for one more day in the motel but…maybe he could change that.

Hours later Harlow found himself walking into a casino, clutching the crumpled bills and change in his hands. Nine dollars and thirty-seven cents the sum total of all the money he had left in the world after being mugged, not even ten dollars or a five dollar bill, everything he had left was in change and singles. Disgusted, he hadn’t even bothered to change his clothes, leaving his now ripped pantyhose on, the chilled wind bashing against his already red knees. Instead he repaired his hair and makeup before walking to the nearest casino he could find. Changing the crumpled ones into a small stack of chips, Harlow already felt better. He let people convince him he had a problem when he didn’t. He had a job. Maybe it wasn’t as stable as what Daniel had been doing but it kept him off of the streets at least. Ten minutes at any one of these tables and he would have rent money for a month. One hour and he’d have enough to get the hell out of town. Just because they refused to see the skill and intelligence it took to accomplish that wasn’t his fault.

Harlow took a deep breath to calm himself and found a seat at the lowest bid blackjack table he could find. He needed to focus, to think, he didn’t need to be working himself up into an angry frenzy. The first hand he had won, doubling his dollar bet to two. ‘Yay, double digits!’ he thought sarcastically but pressed on.

Harlow spent the better part of an hour winning and losing and enjoying the free drinks the cocktail waitress offered as long as he kept gambling. Every victorious hand only made him more desperate for another win. In his desperation he made riskier and riskier bets. Letting the previous bet ride once he managed to make twenty dollars as he was now playing with “house money”. Until ultimately he lost even more than that, losing all but two dollars. He stared at the chips warily, the smart play would be to play conservatively and slowly build up his nest egg. Even if that meant just one dollar bets…but if he lost that? Harlow was wondering how much he could pawn his clothes for when he saw the cocktail waitress stomping towards him. Holding up his now empty cup he called out to her, “Can I get anoth–”

“Piss off!” She swore as she slapped the cup away and continued to storm off.

“What?” Harlow watched in disbelief as two security guards soon flanked the woman and followed her out.

“I apologize for that ma’am.” A short heavyset man said as he approached the table, “If you’ll allow me I’ll  have another drink sent over right away.”

“What happened?”

“Some people just aren’t cut out for this line of work.” He said as he picked up the cup off of the floor and collected the ice off of the table, “Anyway, is there anything I can get you?”

“Actually…there might be. Can we go somewhere and talk?” Reaching out with one hand, Harlow stroked the man’s arm and gave the man his best flirty smile.

A few minutes later, Harlow followed the heavyset manager, who had introduced himself as Carl, into his back office. The office, such as it was, was already cramped with the small desk in the center and two filing cabinets jammed into one corner of the room. When Carl had entered the oversized broom closet it felt positively full.  “So,” he said as he sat behind his desk with a heavy sigh, “you want to work as one of my waitresses?”

“Totally!” Harlow continued with his fake cheer as he sat in a chair beside the small desk, “I, think, like, it’s, like sara-serinpidity, we met when we did.” Harlow giggled, ignoring how he had stumbled on a simple word in his nervousness.

Carl eyed the beautiful girl, she was a knockout and dressed for attention but they all did at first. Still, he took out an application form and a pen, “Do you have any references I can call?”

“Not really, just, like, my bestie.” Harlow kicked himself for using the juvenile term, but it was too late to take it back. All he could do was lean into the bubbly personality Val had forced on him.

“Do you have any work experience?”

“N…no.”

“Anything that might make you qualified for the job?”

“I’m, like, really good at cooking and cleaning now.”

“Now.” Carl said to himself as he placed the pen back in the coffee cup set on his desk, “Have you worked anywhere before?” Harlow pouted, shaking his head. Rubbing his chin Carl did his best to hide the frown upon his face, “Then there really isn’t much I can do besides put your application in the computer and give you a call once I’m done interviewing other applicants.”

“It…it’s, like, just waiting tables isn’t it?”

“It is entry-level work but if I just up and hired you off the street on the spot then that wouldn’t be fair to the other women who’ve applied.”

“Please,” Harlow pleaded, “I know I, like, don’t have a ton of work experience but I really need this job.”

“I have hundreds of women with more experience who need this job too.” Carl ran his hand through his thinning hair, “And how do I know you won’t just up and quit over some harmless fun like my last waitress? Sure you need it now, but when your check clears suddenly you have issues or everything’s sexual harassment and suddenly I’m out another waitress. That doesn’t look so good to my bosses.”

“What if…, like, what if I could prove to you I’m sooo not like those other girls?” Harlow forced a smile to his face again.

“In what way?”

Harlow swallowed what little male pride he had managed to rekindle as he giggled, placing his hand on Carl’s arm, “Let me show ya.” Immediately after Harlow dropped to his knees, hiding the wince of pain by keeping his head down as he reached for Carl’s belt.

Lucy hadn’t even given Carl time to process what she was saying before she began unbuckling his pants. “Whoa! Whoa!” Carl shouted as he jumped back and out of his chair as if a snake had just been thrown in his lap, “Good God, girl! I’m a happily married man!”

“I can make you happy too.” he begged, ‘You couldn’t make Daniel happy enough to keep you from kicking you to the curb.’ The thought came from out of nowhere, striking him in the chest like a sledgehammer. Pushing that thought deep down into the dark where it came from she looked up at the man and doing the best he could to look both hurt and hungry for his cock he whispered, “It can be our little secret.” Harlow licked his lips as she continued, “I can see your friend there wants it too.” His hand caressed his breast outside of his top as she moaned, “Please?” He had been used and manipulated by women plenty in his old life as Harlow so he knew all the ways a woman could manipulate a man but ever since he started living as Lucy men just…wanted her. The thought alone had become intoxicating.

Carl walked around the other side of his desk, his stiffening cock screaming at him as he reached the door.  Looking up at the ceiling, tilting his head back. 'Fuck it, it isn't like my home life is that good. She’s always accusing me of doing this anyways. Why not actually do the thing I'm in the dog house for?' He thought with a sigh and closed the door. "You really want to suck me off, don't you?" He asked as he turned back, looking down at the kneeling girl.

"Mmmm, I really do!" Lucy nodded, ‘It’s not that I want to! I just like,...sleeping indoors.’

“I can respect a cock hungry girl.” He laughed before walking back to his desk. "Show me what you can do,” Carl said as he sat back in his chair, “if you do a good enough job I can have your cocktail route keep you in the high earner areas."

Kneeling underneath Carl’s desk she pulled the man’s pants down further, giving herself more access to his cock. Lucy wasted no time as she kissed the tip of Carl’s cock. Much like the man himself, Carl’s cock was slightly larger than average but thicker than most. She moaned as she licked the shaft of the first cock she had in weeks. ‘That’s just, like, too long!’ she thought as she teased the tip of his cock with her tongue while stroking the shaft slowly. The first droplets of precum seeped out of Carl's cock with an excited moan. Lucy eagerly lapped them on her tongue, responding with a blissful moan of her own. Carl grasped a handful of Lucy’s hair in his hands before pulling her down onto his cock, no longer wishing to wait. Lucy gagged against the girth of his dick forcing its way deeper into her mouth knowing from her own experience just how much men loved hearing a girl gag on their cock.

“Fuck!” He hissed, “You like that?”

Pulling her lips away from his cock just enough to respond Lucy moaned, “I love it. I love your cock.” She giggled and kissed the tip of his wet cock. He shoved her back down onto his dick and continued thrusting into her wet, warm, mouth.

With one hand she massaged Carl's balls as she allowed him to use her mouth and with her other she began to massage the front of her crotch. It had been so long since anyone had done anything nice to her cock she had all but forgotten it was there until she felt the urges swelling up inside of her on nights she couldn’t sleep. Part of her knew teasing herself as she did would only leave her frustrated and unsatisfied again but she couldn’t help it. She missed being wanted. She pushed her fingers deeper into the pussy, the thin material of her panties and hosiery dulling the edges of her painted nails but still managing to touch her penis enough to activate the small twin vibrators as she continued to bob her head up and down on the cock in her mouth.

Having been so long since his wife had given him a blowjob, let alone one as good as the more experienced Lucy gave, Carl did his best to hold back as he all but face fucked the eager young woman under his desk. Gripping her hair tight in both hands he shoved Lucy’s head down onto his cock and moaned as his body was rocked with a shockwave of pleasure. Shooting three jets of cum into her mouth before he could no longer hold on and released Lucy’s hair. Lucy continued stroking the cock with one hand as she drank the pent up load. As the torrent of cum slowly subsided his cock slipped out of Lucy's mouth and Carl shuddered, "God you're amazing at that.” He gasped, “You look so sexy with my cum on your lips. Tell me you love my cum."

Lucy swallowed the literal mouthful of cum in her mouth with a satisfied sigh, “I love your cum in my mouth.” She licked her lips, she was treated to the cum that she couldn’t swallow fast enough. It was weirdly tasty. Lucy continued to lick Carl’s cock clean, enjoying the sweet and salty flavor. Kissing the still hard cock in her hand, she brought her wet fingers to her lips, tasting her own precum that had leaked through her panties under her prodding.

Seeing Lucy hungrily lick his cock caused his little soldier to stand at attention again. ‘Fuck!’ He thought, ‘That hasn’t happened since college.’ “No sense in wasting it.” He chuckled as he helped Lucy off the floor. The little nympho moaned like a puppy as he pulled her away. “Oh, we’re not done, yet.” He laughed as he raised the girl’s skirt and grabbed her pantyhose and ripped them at the seam, exposing the red g-string to the small room.

Lucy shrieked at the sudden force that ripped her pantyhose apart. But that moment of anger was forgotten when the man slipped his finger beneath her panties and into her pussy. Unknowingly to him, activating the small twin vibrators around her cock. His fingers continued to probe her moist slit, bringing her closer and closer to the edge only for him to suddenly stop.

Sitting back in his chair, Carl smiled and spread his legs wide. He didn’t need to say anything, she knew exactly what he wanted. What they both wanted. Lucy took her position straddling the shorter man as she aimed the cock for her pussy. The tip of his cock pressed into her, grazing the little vibrators into soft tormenting pulses.

In a flash the door flung open and Carl all but threw Lucy to the floor. “Hey boss ma–” The female voice froze, “N-nevermind!” She shouted and slammed the door as she left.

For the longest time the two remained frozen in their positions, “I…I guess you should go.” Carl swallowed the lump in his throat as if the reality of what he had done and…what he almost did came crashing down onto him.

“Do…did I get the job?” Lucy asked as she stood to her heeled feet and pulling her skirt back down in place.

Carl refused to look at Lucy as he nodded, “Yeah…just don’t…we can never do this again. Got it?” Lucy pouted but nodded in agreement, “Okay…Come by Monday.”

As Lucy was leaving she avoided the eyes of the women who all seemed to be staring at her. She couldn’t believe yet again she was leaving unsatisfied! Maybe she should give the dildo a try after all…worse that would happen would be she would have to use it on her ass and it wasn’t like she was a virgin there. Hearing the click clack of her heels on the wood floor she paused and looked around the small bar…she could probably find another man and bring him back to the motel. The last guy she let stay over even paid…maybe s he could– 'Dangit dangit, dangit!’ Lucy shook her head and forced herself to keep moving, ‘Get it together Lucy you aren’t a girl... my name is Harlow, my name is Harlow.' He thought to himself as he continued to walk out, unconsciously swaying his hips more than normal to draw more than a few men's gazes.