Press Your Luck 40

Hours after Harlow and Rosemarie had finished their mani-pedis Harlow got off of the elevator  on the twelfth floor. Checking his small red purse once again, ensuring that his phone, condoms, emergency cab fare, and mace were all still inside. Rosemarie said the man had passed whatever vetting process she utilized but she still advised caution. “It’s better to have it and not need it than need it and not have it.” She had reiterated multiple times on his first date and continued to do so on this one. Harlow briefly wondered if that was a lesson she had been taught by someone else as well…or by personal experience.

Pausing in front of the door Harlow adjusted his black off the shoulder bodycon dress so the thin mesh aligned perfectly with his cleavage. Harlow knocked on the door of the suite. “Comin’.” A voice called from the other side of the door. Harlow pushed the worry away from his face, calling up his usual pleasant smile as the door opened a moment later.

A man that stood at five ten and looked to be in his mid-forties with broad shoulders and a beer gut, answered the door with a jovial smile that lit up his sharp blue eyes. “You’re not pizza.” He said with a slight Brooklyn accent, “So you must be Candy.”

Harlow giggled, “Funny.” He smiled, “You must be Frank.”

“I’ll do my best.” He chuckled as he stepped out of the doorway allowing Candy to enter his suite, watching her ass sway in her little black dress as she took in the room. “I hope you don’t mind me saying but you look…amazing.” Frank said as he continued to undress Candy with his eyes.

“This old thing?” Harlow giggled. He didn’t have much experience with actual dating but it seemed almost customary that whenever he complimented a woman’s outfit she would smile and act like any effort she had put into it was no big deal. Only now that he was on this side of things did he realize just how much effort they were hand waving.

Frank licked his lips as he walked to the small bar on the opposite side of the room. “Would you like something to drink before we get started?” He asked politely.

“Totally.” Harlow cheered after confirming with quick glances they were alone in the hotel. Harlow had been in suites before, better ones than this one even, but after living in the cramped motel room for over a month Frank’s basic suite was a palace by comparison. Harlow sat his purse on the small single person bar and himself on a short bar stool in front. “So what brings you to town?”

“Who says I’m from outta town?”

Harlow smirked, “The accent. I lived here, like, my whole life and you totally got the ‘I’m walkin ere’ accent.” He said doing his best Dustin Hoffman in Midnight Cowboy accent before breaking into a fit of giggles.

Frank finished pouring the drinks and fought against rolling his eyes and instead simply laughed lightly before smiling at the pretty girl. Three different cities in fifteen years and every time without fail someone would quote that line to him at least twice a week. “Youse got me there.” He chuckled, playing up his accent to the extreme, “I’m about to get pretty busy at work and I thought; Why not a mini-vacation in Vegas, you know?” He said rhetorically as he finished pouring Candy’s drink, “Kind of unwind before all the stress comes on.”

“That’s smart.” Harlow giggled. “What do you do? If, like, you don’t mind me asking.”

Frank shook his head, as if considering whether or not he should tell the truth. “I’m the assistant coach for the Arizona Cardinals.”

“No way!” Harlow gasped.

“Way.” Frank chuckled, passing the drink to the sexy redhead, “Here in a couple of weeks we’re about to start open try-outs.”

“Really?” Harlow whispered.

“Yes, really.” Frank whispered back before smiling playfully and continuing to speak normally, “Open try-outs are always a pain in the ass, pardon my french.”

Harlow thought for a moment as he considered the opportunity that presented itself. “I can think of a couple of ways to help you be totally stress free.” Harlow giggled as he raised his glass.

“I’m sure you can.” Frank said as he tapped his glass against Candy’s.

Harlow didn’t care about the obvious innuendo. They both knew why they were here after all.  Frank wasn’t model handsome, few people were, but he wasn’t a hideous troll either. Rosemarie had explained like she had with Richard that if he felt uncomfortable for any reason he could always call off the date. Depending on the reason why she would simply send another girl. But that would leave him without getting paid. And Frank didn’t set off any alarms inside his head other than the usual that he shouldn’t be in another suite with another man about to do what they were about to do.

Harlow glanced towards Frank’s crotch hidden behind the small table between them.  ‘Hopefully he’ll…’ He let the thought die away as he finished the drink. This was just a job. It didn’t matter if Frank was handsome. He wasn’t here for pleasure.

“On that note,” Frank said as he finished his drink, “I think it’s time you got dressed.”

Harlow glanced at his tight dress before looking back at Frank in confusion. “I, like, I am dressed.” He giggled nervously.

“Rose did tell ya what I wanted, right?” Frank asked as he walked out from behind the small bar with another drink.

“She told me to dress up.” Harlow pouted, picturing himself in a tight leather corset, leather pants, and leather thigh high stiletto boots, wielding a whip. Harlow wasn’t a stranger to the concept of BDSM but he had really only participated in it once and that had been on the receiving end of Naomi’s hidden dominance. Before when he had brought a lady to his suite he really enjoyed taking control as if it were another victory he had won and couldn’t fathom giving up that power, that control, to someone else. Until he was forced to. Well Naomi didn’t force him exactly, but he would have had to have been insane to turn her down for any reason!

That night had been…magical and not just because he finally fulfilled a lifelong fantasy of sleeping with Naomi but because he knew for certain everything he was doing she wanted. Every moan from Naomi’s lips and grunt of pleasure from Ray and later with Daniel had been truthful and something he had caused. Feeling Naomi shuddering from his tongue. Daniel pulsating in his mouth. Harlow eyed Frank’s crotch once more, having a better view now that he had walked from around the bar. ‘Ugh…fiddle faddle’ Harlow thought as he bit his lip, ‘I’m hungry, I mean horny.’ He shook his head, clearing his thoughts as he stood up from the bar stool.

He should tell Frank the truth; that Rose would have to send another girl who could give him what he wanted…but he really needed the money. ‘I could probably fake my way through it.’ He thought as he stood up from the bar. ‘How hard can it be? You just…do whatever you want, right?’ He added and turned back to Frank and shifted his posture, hoping to appear more in control than he felt.

"G-get over here. Right now, mister! Harlow demanded, which was twice as hard considering he spoke like Marilyn Monroe without having to try anymore. If he were still blonde he could be a dead ringer for the late starlet.

Frank grinned and did what he was told. The sight was almost comical; Candy looked like Jessica Rabbit, sounded like Marilyn Monroe, and whimpered as she tried to bark orders at him. “I thi–”

“Silence, slave!” Candy’s voice cracked as she shouted. “You…you, like, can’t talk without my permission.” Frank nodded, biting his lip to keep from laughing as she scrunched up her face in an attempt to look authoritative but could only manage looking like a coed upset her daddy wouldn’t lend her the car.

“Sit on the bed.” She said, placing her hand awkwardly on her hip. Frank sat on the foot of the bed and silently stared up at her. He knew he would have to tell her the truth sooner rather than later that he wasn’t into the whole mistress/master scene, but her attempt to please him was just adorable.

“You are, like, so bad.” Harlow hissed. “You know what you need?” Frank shook his head. Harlow pouted, he had hoped Frank would suggest something. He was already running on fumes trying to scour his brain for porn references. “You…like…totally need a spanking!” Harlow hadn’t actually known what he was about to say when he started and nearly cheered when the memory of Daniel spanking him when he decided to be rough finally came forward. ‘Yeah?’ He thought, biting his lip to suppress the nervous giggles that kept trying to come to the surface, ‘That could be fun.’ “So…actually…” He bit his lip again, “like, stand up.”  Harlow felt a twinge of embarrassment, realizing the first thought was of being spanked instead of smacking a perfect ass from a girl he had once hired. ‘Wait...I think that was Candy.’ He thought before noticing Frank still sat on the bed, now holding his hand up like a student waiting for permission to speak. “Yes. Slave.” He remembered to add.

Frank let a little chuckle slip before he spoke, “Circling back to that. I think we’ve got our wires crossed. I didn’t ask for this. I had called Rose and requested someone who was willing to dress up in a cheerleading uniform. Not uh…a mistress.”

“Ar…are you sure?” Frank nodded. “Oh. That’s…that’s what she meant.” Harlow pouted. Rosemarie had mentioned dressing up for the client and mentioned something about cheerleaders but by that point Harlow had become distracted by his nails and the faint tan line on his ring finger. “Oops.” Harlow giggled nervously. His relief was overshadowed by the wave of embarrassment that washed over him.

“You want another drink?” Frank asked with a smile.

“Gawd yes!” Harlow's exasperation apparent in his voice. Taking Frank’s glass and quickly downed the liquor. Immediately regretting it once the burning liquid hit his throat. “Thanks.” He coughed. ‘I should go before I, like, make a fool outta myself even more.’ He thought as Frank stood back up and took the glass from the embarrassed feminine man. “I hope, like,you don’t blame…Rose.”

“Huh?”

Harlow frowned, as embarrassed as he was he didn’t want Rosemarie’s rep to be tarnished because he had been too distracted to listen. “She did, like, tell me what you wanted. I just–” He pouted as he cleared his throat– “I can be a total ditz sometimes and just forgot. So…like if you wanted me to, like, call her and send over another girl I totally get it.” ‘Hopefully Rosemarie doesn’t cut me loose for being an airhead.’

“Why would I want to do that?” Frank asked, continuing before Candy could answer, “We all forget stuff now an’ again. I don’t see why we can’t keep this between you and me.”

Harlow smiled and gave a small nod, “Thank you.”

“If you’re up for it we can just start over.”

“You still want me after…all that?”

“I won’t lie, that wasn’t exactly something I was into but you’re still sexy as hell.”  he smirked seeing the small blush come to Candy’s cheeks. “If you still want to leave I’ll take you up on that offer for another girl.”

Harlow thought for a moment before answering, “I guess it couldn’t hurt to, like, know what you wanted before I make up my mind, right?”

Frank nodded, “I’m a pretty simple man actually. I have this cheerleader fantasy, that’s actually what I meant when I said you should change. The uniform is already hanging up in the closet.”

“I bet that confused the heck out of the maid.” Harlow giggled.

“She has been giving me weird looks ever since.” Frank laughed.

“So,” Harlow asked, “you just want me to wear the cheerleading outfit?”

“Well…not just that. Obviously.”

Harlow giggled again. “I think I can handle that then.”

In the bathroom Harlow strained to pull the red skirt into place without tearing it or worse his glittery red nails. In the last month he had tried to eat as sparingly as possible to save money, but between the free trip to the casino’s buffet and splurging on chips and candy at the laundr-o-mat’s vending machines more than a few times a week now he was certainly eating more than he had been when he first left Daniel’s and now it would seem the weight was finally catching up with him. When he had struggled to pull the white and red top over his chest he had chalked that up to it being a size too small but ensuring the white stripes that ran along the sides of the skirt were in line with the center of his hips made it all the more obvious that it was his body that was causing the problem. ‘Ugh.’ He thought as he turned around in front of the mirror to examine just how tightly the skirt clung to his now larger behind. ‘I gotta do something before I, like, totally have my mom’s butt. Or worse, Daddy’s beer gut!’ He pouted and grasped his, thankfully, still flat tummy. ‘But gawd the buffet is so totally tasty after a full shift!’

Harlow was unaware of several things when it came to biology in general, namely that of the pellet implanted in his body slowly dispersing estrogen, spironolactone, and progesterone in his bloodstream day and night which caused his body to change where it would first store the fat in the body. Shifting it from his stomach to his hips and thighs and even his chest first. He was equally unaware of the fact that his late night trips to the vending machine and the daily trip to the buffet were both high in fats and sugar. Accelerating this distribution and compounding the curves of his already feminine form.

‘I can't wait to, like, not have double Ds anymore.’ He thought as he caught his reflection in the mirror and let the dress fall to the floor. Harlow paused for a moment, taking his large chest in his hands with a pout, ‘But, like, I, so, wouldn’t have any money without them.’ In the end he was at least grateful for them for that much.

Holding his chest Harlow bit his lip, reminiscing about the last time he held a girl’s breasts in his hands. ‘I think Naomi was the last boobs I got to hold.’ He thought fondly before pausing and giggling at his image in the mirror, ‘Like, ones that aren't my own.’ He corrects. After a moment, he imagines sucking on Naomi's perfect nipples once again as he continues to rub his chest through his top. ‘Wonder if, like, I can ask for a lady client next time?’ He wondered while biting his lip to stifle the quiet moan that tried to escape his lips. ‘Maybe even Candy?’ He thought with another giggle, ‘Maybe she’s, like, what I need to help me get off? We did, like, do it before already.’ Unconsciously Harlow’s tongue rolled around his mouth at the memory of sucking on her beautiful breasts.

The memory of the salty warm taste of cum slid over his tastes buds as he thought about sucking... the mental image of a breast changing to a cock "Gah! I hate this, I need to get back to my life." He says wishing his own nipples weren't hard.

“You look even better than I imagined.” Frank said from his seat at the edge of the bed, his voice laced with hunger and desire.

“What, this old thing?” Candy cooed as she ran her hands along her body, her left hand slowly lifting the hem of the bright red skirt playfully.

“I bet it wasn’t so long ago you wore it.” Frank rubbed his crotch as he undressed his cheerleader with his eyes, “I bet you even still remember the cheers you and your girlfriends used to do to tease all the players.”

“You’d win that bet.” Candy giggled before taking half a step back from the bed and calling up all the memories she could of watching Valerie and her squad at practice, not even realizing she was unconsciously swaying her hips to unheard music. Taking a deep breath she cheered, “Ready? Okay!” and shook her pom-poms in front of her chest, “Gimme a C!” before using her arms to make a C shape.

“C!” Frank chuckled.

“Gimme an O!”

“O!”

“Gimme a C!”

“What, again?” Frank smirked.

“I said, gimme a C!” Candy stamped her heeled foot and shook her pom-poms at Frank in faux anger.

“C!” Frank laughed as he playfully batted the pom-poms away.

“Gimme a K!” She shouted and kicked her leg high into the air while balancing on the ball of her bare foot.

“K!” Frank cheered along.

“What’s that spell?! COCK! COCK! COCK!” She cheered as she bounced up and down shaking her pom-poms excitedly and kicking her leg higher and higher in the air. Too excited or too unpracticed Candy’s leg swung too far forward in the unfamiliar act causing her to lose her balance and stumble backwards. Luckily Frank’s fast reflexes allowed him to catch the sexy cheerleader. “Oopsie!” Candy giggled as Frank helped right her. “Do you always play the hero?” Candy asked now standing on the balls of her feet.

“I guess you should know the truth,” He paused and allowed his wide smile to fall into a thin line, “I’m Batman.” His voice deepened into a low growl as his eyes narrowed on the beautiful redhead.

Candy raised an eyebrow before smiling, “There’s, like, only one Batman and that’s Kevin Conroy.” She giggled.

“Ya got me there.” He smiled at the beautiful ginger. Half a breath later Frank somehow pulled Candy closer and kissed her beautifully painted lips. A second later Candy folded into him, kissing him back as she wrapped her arms around him.

The kiss had shocked Lucy for the briefest of seconds. She wasn’t sure why. Lucy knew she was there to have sex with Frank. Rose made it abundantly clear that unlike (previous client), Frank wanted sex with her. Not a companion for the evening. But it wasn’t the kiss itself or even what was to come before the night ended. It was the fact the moment Frank’s lips met hers that she thought of Daniel and how his lips felt against her much more plump lips. For a second Lucy let herself pretend she was back in his arms and kissed Daniel.

“I have a little gift for you in the nightstand.” Frank said, breaking Lucy’s spell.

“I like gifts.” Lucy cheered. Opening the night stand drawer Lucy’s eyes widened. Frank’s “little” present was a large purple vibrator. “That’s so not little.” She giggled nervously.

“There’s lube if you need it.” He said without turning back as he opened the heavy curtain against the window that overlooked the parking lot. “C’mere. And bring your friend.” He reminded Lucy. Grabbing the dildo and the lube Lucy did as she was told and met Frank at the window. Frank took Lucy’s hand and pulled her close again, this time pressing her back into him as he kissed her neck and sending little pulses of pleasure all over her body.  “What do you see?” he asked.

“Uh…” Lucy moaned as the kissing continued and her penis twitched in its prison.

“Tell me.” He ordered while his hands caressed her body.

“P-people!” She gasped when Frank twisted her nipple. The pain waking her up even more to the pleasant feelings thrumming all over her body.

“How many?” He asked. His left hand migrated south until it found the edge of Candy’s skirt while his right continued groping her breasts.

Lucy moaned again, gripping the vibrator tight in her hand and forced herself to focus on the people on the street below. The strip was so close. Two stories below her feet were dozens of people walking passed from one glittering building to another; only a few feet from them was a street packed with cars filled with people, only a few feet from them still were dozens more people seeking the next attraction or show. Little did they know how close they were to a show that was only seconds from starting. “I…I don’t know.” She admitted, biting her lips. “T-twenty? F-fifty?” She panted.

Frank’s hand slid further south until it found Candy’s pussy. He smiled as he found the swollen button that pulsed inside and began teasing it with his fingers. “That’s right.” He whispered, “They’re so close.” He kissed her neck again and pulled her cheer top up, exposing her tits to the world, “All it would take is one person to look up and they would see you in all your glory.” He growled, twisting Candy’s nipple before biting her neck. Frank smiled hearing her let out a small gasp as his teeth dug into her flesh just enough for her to feel it before he kissed her neck again. It thrilled him to imagine tomorrow she would have a hickey to either hide or explain.

Lucy bit her lip as Frank continued playing with her nipple. ‘He’s right,’ she thought as she looked out at the sea of people below, ‘What if, like, someone is already looking?’ Goosebumps rippled throughout her body as fear and excitement overcame her at the thought that she was being watched. She didn’t even notice Frank’s hand guiding her own into her skirt until she felt the tip of the vibrator graze her thigh.

Overcome with lust Lucy pulled her panties aside as she watched the people going about their lives unaware outside of the large window. The thought again sent a small shiver along her exposed skin. Pausing briefly she licked her lips as she caught Frank’s reflection in the window before she pushed the tip  of the vibrator into her vagina. The silicone and rubber head looked much too big to fit the small slitted entryway that trapped his own much smaller penis that desperately twitched inside but she was able to insert it with minimal discomfort.

It was a strange sensation at first, neither was real yet she could feel the presence of some new weight as she cautiously pushed further inside until finally she felt the familiar buzzing of the small twin vibrators wrapped around the head of her penis. The buzzing was subtle but wrapped around the most sensitive part of herself; it was maddeningly exquisite! But Lucy’s slow and gentle thrusts wouldn’t be enough. They would only further her frustrations.

“Good.” Frank spoke in a soft voice. “And now…the fun part.”  He had positioned one of Candy’s fingers until they both could feel a small groove in the base of the vibrator. Pressing into the groove  activated its own vibrations. This alone was enough to cause Candy to squeak and squeal as the vibrations accelerated her own vibrators but the purple vibrator began thrusting inside of her as well. The effect of which was instead of a singular steady vibration against her penis was instead waves upon waves crashing into her body just as the last had begun to fade a new one would rack against her.

Lucy closed her eyes feeling the vibrator’s every thrust inside her. She could hear Frank's breathing. Shallow and rapid. The vibrator was doing its job, but hearing his desire in every breath while his hands continued to grope and his lips continued to kiss her neck flooded her mind more with the fantastic dream of the throngs of men who wanted her. All the men and women on the streets who could be looking up at her now and burning with desire to trade places with Frank. Her own cock twitched and leaked behind its prison as she continued to plunge the dildo deeper. Driven solely by her maddening lust by the images of men and women caressed and groped at her exposed flesh. She could feel the familiar crescendo building inside of her. She was so close now! She had been here before. She knew this was as close as she could get. Whatever was wrong with her was like trying to demolish a dam with a spork.

Lucy moaned in frustration as she rode the edge of her orgasm when Frank suddenly spun her around and before she knew what was happening she was flat against the cold glass sending shivers across her back and her new favorite toy gone. The ever present vibrations was quickly replaced with something else, something with less weight, something smaller, something that attacked her with a ferocity she was not expecting. Lucy had barely any time to understand that Frank had dropped to his knees to go down on her before she felt his wet tongue, slick with the juices of her own precum lapping at the head of her penis buried within her prosthetic. “Wha–” She began, only to be cut off by a new explosion of pleasure different from what she felt with the vibrator. Grasping Frank’s hair as she groped at her chest just for something to hold on to Lucy arched her back as that edge that had been so impassable before began to crack. Her nimble fingers pinched her nipples as the world outside the window faded away and the cracks became breaks. Lifting her breast to her plump lips she sucked on her hard nipple until everything, even Frank, was gone from her mind and the dam burst wide open, letting the pleasure wash over her even as her body convulsed in short bursts.

Watching Candy playing with herself, how her cheeks flushed with every kiss upon her neck, how she moaned at every touch of his hand followed by a soft barely audible gasp begging for more had been too much for Frank. He had intended to watch more but the scent of sex was already in the air and driving him wild. Dropping to his knees he had easily turned the smaller girl around and pulled the vibrator out and away before lapping at the folds of her smooth pussy. The scent of sex meeting his nose spurring him on. Feeling her twitch and shudder under his tongue while her hand gripped his hair in uncontrollable desperation made him smile and his cock stiffen. He loved the different flavors of women and would recall the memories often when he’d masturbate but Candy’s tasted so radically different he wanted, no, needed more! He found her engorged clit and doubled his efforts as each new drop of precum touched his taste buds. It wasn’t long under his skillful tongue before he felt her cumming and he lapped up every bit of it as the moans escaped her thrashing body. When he was sure he could find no more of this new flavor of woman and her body had stopped convulsing in orgasmic bliss, reduced to a quivering mass, he stood and kissed her lips. Candy giggled as she happily kissed him back. Only to shriek as he lifted her up and used the glass to hold her in place before pushing his cock into her wet pussy. She had had her first orgasm of the evening, now she would give him his. The first of many.