Press your Luck 13 (Patreon)

After about thirty minutes Valerie knocked on her bathroom door and found Harlow reclining in the tub, with a rag over his eyes. Looking at him, the bubbles that hadn't yet dispersed clung to his breasts as they gently rose and fell with his breathing. It was almost easy to forget Lucy was ever Harlow in that moment.

But she carried on; woke the sleeping Harlow and watched him redo his make up, with more than a little coaching on her part until he looked ready for the clubs, and he got dressed again in a pink bustier and matching miniskirt. Of course this meant a change of heels as well. He now wore clear five inch heel platform sandals.

“Did you enjoy your soak?”

“The water was a little hot.” He refused to admit just how relaxing such a girly activity was, at least not to Valerie. When this was all over and he was back in suites he would definitely try and recreate the experience.
“You’ll get used to it. It’s, like, really good for your pores.” Valerie nodded, agreeing with herself, “Now,” She shifted her voice, trying to sound like an 80s computer villain, “would you like to play a game?”

“Huh? Oh. The drinking game. Sure.”

Valerie was thankful that Harlow didn’t get her reference as she brought out a bottle of clear tequila and two shot glasses. After high school she stopped hiding, what others would call, her nerdiness and love of science fiction books and movies. Just another way she had to fit in with her friend group who hadn’t fully matured yet.

“Okay, so the rules are simple; First one to fall out loses, obviously. You have to swallow all of it, something we already know you’re used to.” She teased, making Harlow blush, “And I thought of a way to make it fair.”

“How’s that?” Harlow asked, sitting at the table. Grateful to be off his feet. His ankle didn't hurt in the heels but everything else seemed to, and walking was something else entirely. If nothing else he had a new appreciation for those ballet girls who walked on their toes.

Valerie placed a pair of dice between the two of them as she sat down. “It’s called 7/11. Whoever, like, rolls a seven or an eleven the other person has to drink. But, like, if you touch your glass before I touch the dice you have to do two shots. If you don’t drink before I roll, you have to do two shots.”

“Sounds fun.” Harlow smirked, he always cleaned up playing craps, Val had no idea what she was getting into. “So who goes first?”

“Why don’t you, since you lost the last game.” Harlow frowned but picked up the dice. These dice were definitely not your standard issue dice used in casinos. Most used a translucent red or green dice, these were solid white, with clock faces indicating the numbers rather than standard dots.

He watched Valerie pour the alcohol into each of their glasses. ‘Whatever, she’ll still lose.’ He shook the dice in his hand for a quick second before rolling them onto the table. The dice bounced and clattered, hitting a salt shaker and rolling to a stop on five and six. “Hah! Drink up.”

Valerie smirked, “When you pick up the dice I will. Nice try, sis.” Harlow shook his head, ignoring her teasing and picked up the dice, when he did Valerie tossed back the shot, making a pained face as it made its way down her throat.  “Ugh…Yahtzee!” She giggled. Harlow giggled with her and rolled once more, landing on two and five. “Hah, seven!”

“Wow, what are the odds!” Valerie grimaced as she poured her second shot in ten seconds. Valerie had planned for this, she knew from high school his favorite games involved dice as he had been caught more than once rolling bones in the gym. The game, of course, enticed him and he was no doubt good at it, hearing some of the stories from Danny. Though those were likely exaggerated by Harlow and Danny was simply too trusting to question him. But, she had loaded up on crackers and bread while he napped in the tub. She wanted him to be overconfident and have a good lead before she pulled the rug out from under him. Now she simply had to play her part. Harlow picked up the dice and rolled once again as Valerie drank.  And again he won.

The next three rolls were the same, and Harlow was feeling cocky having watched Valerie throw back six shots in under a minute. “I hope you didn’t go to any trouble for your deal. Cause it looks like you’re gonna lose.”

“Juss you way. I have,um, stragetemies.”

“Sure you do.” He he said in his breathy  voice before giggling.

Before he could roll again Valerie asked, “Wah…wut did you, like, want if, maybe, like, you won?”

He smirked, “I think you should definitely take a bubble bath.”

“Souns fun.”

“With me.” Valerie giggled. Harlow joined her before rolling the dice once again. This time he only managed a three and a five.

“Oof, so close.” She giggled, reaching for the air beside the dice before grabbing them up herself.

“Yeah, yeah, the game's not over yet.”

Valerie smiled, rolling the dice softly out of her hand. Her first roll was a one and a six. “Yo! You drink!” She giggled.

“Beginners luck.” He giggled, picking up his glass and throwing it back.

“Ah, ah! You didn’t let me get the dice first.”

“Shit.” He swore, pouring himself a second shot. “I’m just used to you drinking.” He teased, throwing back his second shot.

Valerie giggled loudly, “You did it again!”

“What?”–Harlow giggled–“No, that was, like, the penalty one.”

“Yeah, but the rule still, like, applied.”

“Ugh, fine.” Before he could pour another Valerie scooped up the dice and rolled again, landing on three and four.

“Hah! You gotta do two!”

“Wai-no fair! I was still pouring!”

“Gotta keep up, girly. And since you swore you gotta do another penalty shot.”

“What? Why?”

“Good girls don’t swear.”

“You’re just trying to get me wasted so you can win.”

“Fine, if you don’t wanna do another shot, you can be punished later with something worse.”

Shaking his head, Harlow quickly poured another shot as Valerie reached for the dice. He immediately swallowed it before she could roll. Harlow shivered, “Yahtzee!” He giggled.

Valerie giggled back, not even mad she rolled a nine total. Harlow had just drunk four ounces of alcohol in thirty seconds, while she had been given a short reprieve from her own drinking. “My turn!”

“Yeah, yeah, game not over.” She smiled. Harlow picked up the dice and shook it in one hand. “Bet you like doing that, huh?” Valerie teased, making a jerking motion with her own hand.

“Gross.”

“Nah, it’s hawt. You know you love it.” They both giggled again, as a dice slipped out of Harlow’s hand and bounced on the table.

“Oops!” He giggled again as he reached for the dice.”

“Don’t touch it!” Valerie said quickly, “It’s in play.”

“Fine.” Harlow groaned, looking at the one, knowing it would be impossible to get a six. As he expected he rolled a three on the second.

“Heh, my turn.” Valerie scooped up the dice, rolling two threes.

“Ha.” He laughed reaching for the dice, but Valerie was quicker and grabbed them both.

“Doubles, I roll again.”

“Oh…okay.” He couldn’t recall if that was a rule or not but in some casinos it was allowed.

Valerie’s next roll was a three and a four. “Yay!” She cheered and reached for the dice.

“Yeah, yeah.” He threw back his shot.

“What are you doing?

“My shot, cause you already touched the dice?”

“I hadn’t.” Her hand hovered over the dice, blocking their view from Harlow until he changed his angle lower.

“Son of a bitch.” He poured another shot and heard the familiar clattering before he could finish. “Wait!” he coughed, some of the liquor going down the wrong way.

“Another! better hurry up.” Valerie managed to trick him four more times with the same and similar tricks before her next rolls forced her to stop. “And you swore,so you’ll have to be punished.”

“Whatever.” Harlow now shifted unsteadily in his seat trying to keep in time with the room as it spun. Harlow grabbed the dice and dropped them. “Sev?” He asked, blinking at the hard to read dice.

“Sure.”

Harlow grabbed the dice again, dropping one almost immediately and rolling the second, rolling a one and five. “Okay…” he forced his eyes to focus on Valerie’s shot glass. “Did you do your shot?”

“Totally.” She lied, picking up the dice. Dropping them softly they landed on a two and three. “Seven!” She cheered. Harlow grabbed his shot glass and slowly drank it down. “Eh, I didn’t touch the dice yet.”

“Uh…” He groaned, doing another shot and three more.

“Eleven.” Valerie said without even touching the dice. Harlow reached for the glass, but stopped.

“Eh, almost got me. But, like, eyes to smart.” He pointed. “Pick em up first.”

“You got me. You’re so much smarter than me.” she giggled and picked up the dice.

“Of course I am.” He drunkenly giggled back before throwing back his next and final shot.

Valerie dropped the dice. “Seven.” She said without looking.

“Oh kay.” He reached for the bottle, frowning as only a few drops came out, but swallowed it down anyway. “All gone.”

Valerie smiled, he really was a lightweight ditz but a dozen shots of 90 proof on an empty stomach will do that to just about anyone. “Looks like. I win.”

Harlow rested his chin in his small hand. “Uh huh.”

“So I think it’ll be easier if you go ahead and pay up now.”

“Hmm, okay.” He reached into his skirt, sad and pouting that he couldn’t find a pocket. “Someone stole my pockets!”

Valerie giggled, Harlow drunkenly giggled, laying his head on the table. “Yeah. But you are so sexy.”

“I am sexy.” He smiled.

Valerie took out her phone and started recording. “What are you?”

“Sexy.” He giggled drunkenly.

“A sexy what?”

“Um…a sexy slut for sex.” He laughed.

“Have you and Danny had sex yet?”

“Nooo!” He groaned.

“But you want to?”

“I want sex.”

“With Danny?”

“Nooo. Not…not with Danny.” he slurred somehow.

“What about Harry?”

“Hmm. No Harry.”

“Why have I been seeing used condoms in the trash then?”

Harlow giggled. “My idea.”

“You jerk off in the condoms?”

“Nooo. Danny does though. I’m supised they fit. He’s so big!” Harlow giggled again.

“I know what I want you to do since you lost.”

“C’moooon. Double nothin’.”

“You wanna double or nothing again?”

“Mhm.”

“Alright.” She smirked wickedly before closing her phone and standing up to get a quarter out of a small change jar on the counter. “Heads I win, tails you lose. Okay?”

“Kay.”

“Okay.” She flipped the coin, it bounced and spun before landing on tails.

“You lose again.”

“Ugh.”

“For this one though, I think it’s time you paid up. Come here, girly.” Valerie helped Harlow stand and held on to him as they walked back to Valerie’s office.

Ten minutes later Danny's phone pinged while at work. Seeing it was an email he left it for now and continued welding.

Back in Danny’s room, Harlow sat on the edge of their shared bed as Valerie took out a small bottle of lube and dripped the oily substance over the hard rubber cock. “Are you sure you’re ready?” She cooed, already knowing the answer would be no if Lucy wasn’t drunk and horny enough to not understand what she meant when she said she would show her how to use her new toy. Instead, Lucy nodded eagerly. “Okay.” Harlow didn’t question why Valerie stood him up again, or why she pulled down his panties as she sank to her knees. All he cared about was the fact he was about to watch this sexy bimbo get off. “Okay.” She stood back up, her breasts touching his own now exposed chest. “I think you’re gonna love this. But you’ll have to do what I say. Okay, Lucy?” Harlow nodded, ignoring the given name at this point. Slowly Valerie massaged Lucy’s back before working her way to her butt. Harlow blushed as the motion did just graze his tip enough to cause his penis to throb and pull painfully against the glue trap. Harlow didn't question it as Valerie lowered him down on the bed, at least, not until it was too late and he felt his cheeks being spread  apart as the greased up cock slid into his hole.

“What are you doing?” He gasped and tried to pull away, but he wasn’t prepared for Valerie’s superior position.

“I told you. I’m gonna show you how to use it, and you’re gonna love it.” Before he could protest further he felt a sharp pain as the cock entered its halfway mark.

“Fuck! Get it outta me!” He yelled.

“It’s okay. Just relax.”

“How am I supposed to relax with this bitch inside of me?!”

“If you don’t it’ll only hurt worse!” She yelled back.

Harlow grimaced, his thighs burned as he was trapped between sitting and standing, unable to move in either direction without pain. Valerie kept her hands on his shoulders so even if he could get his balance she would be more than capable of pushing him back down. Harlow bit his lip and tried to force himself to relax. If he was lower he could possibly roll away or something less than dignified but at least he could escape.

As he passed the seventh inch his heart jumped. Something...felt good. Drunk and stressed Harlow couldn’t prevent the small smile that escaped as he gasped when the dildo first grazed his prostate. He quickly hid it away again, hoping that Valerie didn’t see it and thought he actually enjoyed this.

Valerie smiled, pushing him further, she was right. He was going to love it, he just needed to get out of his own way. “See? Doesn’t it feel good?” She cooed as she ran her fingers through his hair.

Harlow’s entire body rippled with pleasure, both sexual and sensual, as the fake cock slid futher in and the ridges sent ripples upwards. Harlow had never had a woman play with his hair before so it caught him by surprise at how good it could feel as that sensual pleasure rippled downward. It was too much for his mind and body, he couldn’t hold back his smile as he stared at her tits and bit his lip. His mind would come up with reasons why he enjoyed it later, reasons that would protect what still remained of his heterosexuality.

Finally he managed to take the last inch of the cock, its balls touching his pulled back penis. After more than two weeks of being given little to no contact his own penis twitched, feeling someone, something, finally touch it. His lower half was a mix of pleasure and pain as Valerie pulled him down to his side.

“What are y-” He started to say, cutting himself off with a girlish squeal as he felt the dildo slide out, only for it to come forward again sending another sudden burst of pleasure to his brain.

“Do you like it?”

Harlow gasped but said nothing.

“Do you like it?”

“N-no.” he lied, the pain of his penis trying to tear itself to freedom the only thing helping to focus his thoughts.

“Tell the truth, Lucy.”

“I-I don’t.”

“We both know you love it, why don’t you admit it?”

“I’m not gay!” His yell turned into a moan as the dildo continued to massage his prostate.

“It’s not gay if you like it, Lucy. Is it gay if you touch your dick?”

“MMM.” he groaned.

The pleasure stopped as did Valerie. “Is it?”

“I guess not?” He gasped, not really listening but glad for the reprieve. The dildo started moving again. “Fu-” Harlow moaned.

“So how’s this any different?” She grabbed his free hand as she continued. “You’re just getting yourself off.”

“Not…don’t…like.” Harlow said between gasps, unsure how to order his thoughts. “Drunk.” He finally said.

“You’re drunk?” She asked.

“Mhm.”

“It doesn’t count if you’re drunk?” She placed his hand on the bottom of the dildo, continuing her sawing motion together.

“Mhm.”

“So you like it?”

“Mmmmhm.” He finally answered. It didn’t count. He was drunk. He liked weird 80s glam music when he was drunk too, but not when sober. This was no different. Plus, he lost a bet. If he hadn’t he wouldn’t have been this drunk and definitely wouldn’t even attempt this.

“Like what?”

“This.”

“What is it you like?”

“The…pl-lp…the touching.”

“Touching with what?”

“Myself.”

“What are you touching yourself with?”

“Mmm.” he groaned, feeling his left hand being moved atop the fake breasts he still wore.

“Tell me.”

Harlow massaged his breast as he continued, unaware that Valerie’s voice now came from a different place,“The…the dildo.”

“What’s a dildo.”

“A fake dick.”

“Would you like it if it were real?”

“No.”

“Why not? The real thing feels a hundred times better.”

“Imnotgay!”

“No you’re not. You’re Lucy. And you like the dick inside of you right now, right?”

“Hmm.”

“It’s okay, Lucy. It’s just us girls here. I won’t tell anyone.”

“Yes.”

“You like the dick inside of you?”

“...yes.”

“Do you wish it was real?”

“Mmm…yes” Harlow said in a small, soft, voice.

“What did you say?”

“I do.” His face burned bright red.

“You wish it were real?”

“Yes.” He said slightly louder as he felt his ass moving on its own in time with the cock in his ass.

“You wish you had a real cock in your ass?”

“Yes.” He gasped, the dildo twisted and touched his prostate even more than before.

“Then say it.” Harlow pouted. “It doesn’t count, remember. You’re drunk.”

“I…I wish it were real.” He gasped, imagining if it felt this good when it was fake…if it were real and supposedly a hundred times better…how good must that feel?!

“See, I told you you would love it.”

“Hmm, Love it.” He moaned, imagining himself with Naomi, his cock deep inside of her and Candy behind him. She had told him before that some men liked that, if he could get ahold of her he would have to ask her how much it would cost.

Harlow continued in the silence, unaware Valerie had left several minutes ago before he heard a new voice. “Lucy?!” Harlow jumped, forcing the dildo painfully deeper and at an odd angle before it fell out just as painfully as he saw Danny’s bright red face staring at him. Between the hot water, the constant pulling as he tried to get hard, and now the jumping motion, it was too much and the last of the glue separated as his penis ripped free, standing straight up and pointing at Danny as it leaked precum.

Harlow pulled the covers over his naked body. “Danny! You’re here?” He yelled.

Danny swallowed hard and closed the door behind him, locking it. With his long legs Danny cleared the distance in one large step and pulled Lucy into a deep, soulful, kiss.

Earlier, Danny had gone on break and decided to check his messages. He found a new email from a new person not yet in his contacts called LustyLucy. He would have immediately deleted it but the subject read, “Lucy loves her boyfriend Danny.”

Taking the risk he opened it and smiled, seeing it was a message from Lucy. She didn’t  have a phone so she found a way to send something sweet to him anyway. Judging from her smile in the video’s preview she was very happy. “Danny!” She giggled as the video started. “I miss you!”

“Aw.” He smiled as he ate his late lunch.

“I wish you were here.” She moaned slightly. Danny blushed and checked the empty break room once more to ensure he was still alone. “I’m soooo bored.” She giggled again. “But, like, I have an idea.” His eyes widened as she pulled out her breasts from the pink leather bustier she definitely wasn’t wearing that this morning. He swallowed hard as she started to massage her breasts. “If you come home right now. We can play a game.” She paused for a moment before reaching off screen and bringing out a dildo.

“When did she get that?!” He couldn’t imagine Harlow had ever owned one of those…but this was Lucy.

“I guess I’ll just have to play with myself.” She pouted and Danny felt his cock twitching in his jeans. “Unless…you come home soon,” She slid the cock between her breasts, “then, like, we could play together. But you better hurry. I won’t wait forever!” She blew a kiss to the camera just as the video ended.

So, Danny raced home and found his girlfriend masturbating in their bed, her penis begging Danny to help her. Immediately he kissed his girlfriend. She had said something, but he wasn’t paying attention. He was tired of jerking off in condoms while this sexy woman lay next to him. He didn’t want to be the first to admit it, afraid he was misreading signals yet again, but he wanted Lucy! And she obviously wanted him just as bad. But she got tired of waiting. The way her tongue danced with his, her hand squeezing and pulling his sides in closer, the soft little moans she made as they kissed. They were both finally going to get their wish. They would discuss what that meant for their friendship later on when they were in their right minds once again. But for now, all either of them wanted was the pleasure of each other's bodies.