Press Your Luck 18 (Patreon)

Harlow squealed again as he bounced on the bed where Danny dropped him, his fake breasts bouncing heavily in his dress. “Lucy, you are so beautiful.” He said as he threw off the expensive coat.

“You don’t look so bad yourself, handsome.” Harlow giggled drunkenly. Though he hated to admit it, Danny did look handsome in his suit. While Danny took off the vest Harlow reached into the nightstand and pulled out one of the many condoms. “You’re not gonna take all night, are ya?”

“Someone’s eager.” Danny laughed. Daniel was happy to see his friend was much happier than he had seen him in years. Harlow was clearly much happier as Lucy.

“Something like that.” Harlow’s once flat poker face had been replaced, he no longer had to think about smiling, it was simply something that was a part of his face now.

Daniel discarded his pants, his rock hard cock bulging in his boxers, then pulled Harlow to his heeled feet, kissing him passionately. Harlow nearly fell into the taller man as he raised one heel off of the floor in an attempt to keep his balance. Which is why he didn’t attempt to push Daniel away, at least, that’s what he told himself. He couldn’t push the much larger man away on the best of circumstances, but with one heeled foot on the floor and practically standing on his toes there was nothing to do but enjoy it let it happen. Finally Daniel released him and Harlow gasped as he held onto his giant friend.

He tapped Daniel’s nose with the condom and giggled awkwardly, not sure what else to say. “Boop.”

“Really?” Daniel took the condom.

“I’m not ready to be a mother, Daniel!” He giggled again.

Danny rolled his eyes with a smile and kissed Harlow again. “Turn around.” He said firmly. Harlow cocked his head to the side for a second before turning around, it wasn’t like he hadn’t seen his friend’s cock by this point, but then it wasn’t like he wanted to see it again either. It was extremely awkward the first time he had to be in the same room as Danny jerked off. Harlow simply assumed he was going to do like they had done in the pool bathroom. Suddenly he felt the straps of his dress being pulled down exposing his lack of a bra. His fake breasts pulled slightly with their weight. “What are you doing?” He shivered as more of his skin was exposed to the bedroom.

“Don’t worry, I won’t forget the condom.” Daniel whispered before kissing Harlow’s neck.

Harlow moaned. Why did that have to feel so good? He could simply let Daniel kiss his neck all night, riding the blissful feelings of pleasure while his strong hands explored Harlow’s body however he wanted and in that moment he could think of nothing better.

His penis pulled painfully against the glue against his skin breaking the fantasy. “No.” Harlow gasped, turning around and covering his chest with one hand. “You’re supposed to use the condom.”

“I will.”

“No…just the condom.” It was Danny’s turn to cock his head to the side in confusion. “I’m not gay, Danny.” Harlow blushed. Whatever was going on with Danny, he was not a part of.

“I know you’re not.” Danny tried to tuck a strand of Lucy’s hair out of her face but Harlow turned away.

“Just put on the condom and…do your business.”

Lucy sat on the bed, covering his chest. She refused to meet Danny’s eyes, choosing instead to stare at the nightstand. Danny frowned but took off his boxers anyway. He should have known it wouldn’t be that easy, he thought to himself tearing open the condom wrapper. Val had warned him that she wasn’t used to a straightforward relationship yet.

Harlow watched the nightstand as he listened to Danny struggle to place the condom on his hard cock, why didn’t he just leave? He asked himself when he heard Daniel wincing in pain. “Ah, fuck.” he swore.

Finally facing him, he saw Danny holding his wrist in hand. “What’s wrong?”

“Nothing.” he lied.

“No, tell me.”

“...my wrist.”

“Because you’re not wearing your brace.” Harlow stood, taking Danny’s hand in his and kissing his injured wrist.

“I know.”

Harlow tenderly kissed Danny’s wrist, “Why didn’t you wear it tonight?” he asked softly despite his anger. Why was he even angry? He wondered. So Daniel was being stupid, why should that bother him?

“It didn’t go with my suit.”

“Bullshit.” Harlow still kissed Danny’s wrist tenderly again.

“Eh, that’s another chip in the jar.” Danny smiled. His smile quickly faded seeing the angry glare the half naked girl was giving him, “I wanted to look good for you. Okay?” Danny said feeling a bit awkward talking about wanting to dress well for Lucy when he was sitting there naked and with his dick at full mast.

“For me? Why?” Harlow’s face softened. Why would he care what Harlow thought? He looked handsome in his suit, but most men did. That was the power of a well tailored suit.

Danny shrugged, “I don’t think I can do it…myself. Not tonight anyway. Maybe when I’m off the injured list.”

Harlow nodded, why was he still half naked and still kissing Danny? The thought of Oswald in their room suddenly filled his mind. He had been in here…he had looked through things, searching for whatever he wanted under the premise of searching for Lucy’s purse. “No.” He said suddenly, “It needs to be done tonight.”

“Wh-I can’t. Like physically cannot.” An idea popped into Danny’s head, “Unless…you?”

“What? No!”  Harlow shouted, dropping Danny’s hand all together.

“You want it done, right?”

“Y-yeah.” Harlow pulled his arms into his chest.

“And I can’t. So…”

“...I’m not gay!”

“I know you’re not. You’re my girlfriend. Helping out her boyfriend.” This time when he tucked a strand of hair behind her ear Lucy didn’t pull away.

Harlow thought for a moment, his eyes frequently glancing at Daniel’s large cock. He couldn’t do this. He wasn’t gay. But they had proven multiple times that they could and would break into their home and search for proof that Lucy wasn’t who she said she was. Danny was hurt because of him after all.

Danny sighed, “What’ll you give me?”

“What?”

“You want it done. I can’t. So you’ll have to.” He said as he sat on the bed next to Lucy. “But what do I get out of it?” Danny hated himself for saying it, but if Valerie was right and it was looking more and more like she was, then Lucy would be more comfortable making a deal.

“Getting to cum isn’t enough?”

Danny shrugged, “I can wait.” He lied. It took every ounce of strength in him not to throw Lucy on the bed and ravage her like some caveman.

Harlow nodded, “What would you want?”

Danny thought for a moment, he recalled the look on Lucy’s face as she stared at Isabella with envy. She wasn’t a great dancer, or even good really, and she so clearly wanted to be. “I want you to dance.”

“Right now?”

“No. I think you should learn to dance. For me.” He quickly added. If she thought of it as a way to pay him back for something then he knew she would be more likely to go through with it.

Harlow nodded, “Okay.” Harlow stood and took another condom out of the nightstand, the original lost in the dark somewhere. He should have expected this even from Daniel, he thought, Jefferson wanted sex from Lucy. Harry definitely wanted to have sex with Lucy. No, not Lucy…him. Harlow.

Harlow sat on his knees in front of Daniel, finding it the easiest place to be for what he was about to do, and opened the condom. Daniel’s cock now hung limply in front of his face. Even soft Danny’s cock was bigger than his own penis that was tucked and glued away. ‘Not like I haven’t done this before.’ Harlow reminded himself, hoping that would clear his anxiety, as he grabbed Daniel’s cock in hand and stroked it slowly until it stiffened. “Hmm, baby that feels good.” Harlow’s smile fought to try and widen itself at the compliment while Harlow rolled the condom on Danny’s now hardened cock. He had actually gotten Danny hard! He had seen him hard before, more so these last couple of weeks, but now he had actively stroked his best friend’s cock in the hopes of getting him hard and succeeding. Harlow shook the thought out of his head as he jerked Daniel’s cock aggressively. The only way to pretend this hadn’t happened was to finish as quickly as possible!

Danny moaned as Lucy jerked his cock furiously. Between the beauties grinding against him all night and the memories of sex with Lucy just a few days ago he wasn’t sure how long he would last even with the condom in place but he fought as hard as he could to hold himself back. “God damn!” He moaned and grabbed Lucy’s hair in his hand, pulling her closer to the tip of his cock so he could feel her warm breath on him. He wanted to shove his cock into her mouth, and judging by her smile she may have even wanted him to, but that wasn’t part of their deal. Lucy adjusted so she could jerk his cock while in between her large breasts.

“You like that?” She cooed.

“Ahh. I love it!” He moaned again, “Mmmfuck!”, fighting the urge to push his girlfriend down onto himself.
“Cum for me Daniel, cum for me.” Harlow said in the breathy Marilyn voice that Harlow no longer had to think about it to talk in.

Danny bit down hard on his lip, trying to hold his cum back. But hearing Lucy begging for his cum was simply too much and he exploded in the condom as she milked every last drop out of him.

“Fuck!” Harlow swore. He had been doing everything he could to make Daniel finish quickly and in so doing he had ripped the condom without even noticing until it was much too late. When Daniel came the first spurt was all the condom could contain before it fell off and thick white ropes of cum had landed on Harlow’s face and tits.

“That was so hot.” Danny gasped, his face bright with euphoria and his chest heaving with exertion. He hadn’t expected Lucy to pull the condom off at the last second so he would cum on her face, but he certainly wasn’t complaining at the moment.

“Towel.” Harlow demanded, his right eye sealed shut with thick white goo.

“Oh, right.” Danny laughed, covering his cock as he hurried into the bathroom, taking one last look at the sexy sight of his large chested girlfriend dripping with his semen and thinking just how hot it was that she did that.

“Stupid cheap shit.” Harlow swore, tasting Danny’s cum on his lips and on his tongue. Some got in his mouth as he talked as the cum dripped down his face.

The next day was once again awkward for Harlow as he woke up with an arm and a leg draped over Danny, the taste of his cum still in his mouth. Quietly, Harlow snuck out of bed, hoping to go through his morning routine uninterrupted. But after he softly closed the bedroom door and turned to make the short distance to the bathroom he saw Valerie. “Good morning.” He smiled and forced himself to act casual.

“More like good night.” Valerie smirked. Before he could ask what she meant she walked away laughing.

“Airhead.” He whispered to himself and walked to the bathroom. In the mirror he immediately understood why Valerie had laughed. Right there on the corner of his lips was Daniel’s dried cum from the night before. Missed by his hasty towel scrubbing. Harlow made sure he washed his face as Valerie had shown him. Twice.

After making breakfast and getting ready for the day Harlow kissed Daniel goodbye, ensuring first he had his brace before he had allowed Daniel to leave. Catching Valerie’s eye, Harlow quickly picked up the dirty dishes and started to wash them. Valerie followed of course. “Sooo. I take it you had a fun night?”

“The food was good.” He scrubbed an already clean plate.

“Yeah? Did you do anything else?”

“Not much else.”

“I don’t know, I left around ten and you guys were still out.”

“Yeah. Where did you go?” He asked, not really caring but hoping to change the subject.

“I went to hang out with Naomi for a bit. We talked, had some wine, and I crashed in her spare room.”

“Sounds like you had the fun night then.” He placed the cleaned dish into the dishwasher.

“It was nice. How about you?” She prodded once again.

“I told you. The food was nice.”

“Ugh. Come on! We both know I saw what I saw. So spill.”

“I don’t know what you’re talking about.”

“Uh-huh. So you just, what? Snuck out of bed, had ice cream in bed, and then snuck out of the room again this morning?”

“You caught me. I like ice cream.” He spoke flatly, still staring at the dishes in the sink.

“Come on!” Valerie grabbed Harlow’s shoulders, turning both towards her. “Spill, girl.”

Harlow ground his teeth against each other, “Why? What the fuck business is it of yours?” Valerie paused for a moment. In her excitement she had forgotten to maintain her distance. They weren’t friends, at best they were patient and doctor and she wasn’t technically a doctor yet. She was simply pretending to be the friendly, bubbly, bimbo she used to play back in highschool. Excited about all the latest gossip and who slept with who. That wasn’t who she really was, she told herself that she was had just got caught up in the moment.

“You’re right.” It was Harlow’s turn to be taken aback as Valerie stormed out of the kitchen. She returned with the horrible dildo in hand, "Since you were, like, so kind to remind me, we are not friends.”

“What the fuck is that for?”

“Punishment.”

“What?”

“You keep swearing! I told you I’d come up with a punishment for your potty mouth. So for the next hour you’re gonna suck on your little friend here.”

“I’m so not doing that!”

“Okay. Then leave.”

“What?”

“I let you slide on too much. But we’re not friends. So either you get to suckin’ or you get to walkin’.” She slammed the dildo on the chair, the suction cup immediately catching it in place.

“I’m not doing that!”

“Then leave! Right now as you are. I tried being nice but you spat in my face. I’m trying to help you and you clearly don’t want it. And if that’s the case then leave.”

“Fine!”

“Good. I’ll call Marcus or Jefferson or whoever else and let them know.”

“They’d hurt you and Daniel.”

“Not when I tell them you lied to me and duped Danny. They clearly like him. I can spin it.”

“You’re not that smart to manipulate these guys.”

“You wouldn’t be the first girl who’s life I ruined because she made me mad.”

Rumors had swirled around the cheer squad about how many lives they had ruined just for fun and games. Supposedly the worst of them all was their head cheerleader, Valerie. “...you wouldn’t risk you or Danny.”

“Wanna bet?”

Harlow looked between Valerie and the dildo. Maybe he could get out of town, but Lucy was a great disguise and it wouldn’t take long for Marcus to catch up with Harlow or Lucy. Hell, he probably wasn’t that far from the house now. “Val,” He said softly, “I’m s-”

“The only sounds I wanna hear come out of your mouth for the next hour are grrgle glech!” She imitated short choking sounds as she glared at Harlow.

“Fine.” Harlow stomped to the kitchen as best as his heels would allow him. His heels clicked furiously across the floor.

“No alcohol.”

“What?!”

“You’re gonna have to get used to doing it sober sooner or later.”

“I don’t want to get used to it!”

“Please.” She scoffed and rolled her eyes. “You’ve sucked more dick in a week than most girls do in a year.”

“I have n-”

“What did I say? Get on your knees and get started on your boyfriend or get started walking.”

Harlow shook his head as he slowly walked to the dildo before sinking to his knees and gripping the large rubber phallus in his painted hand. “Don’t act like this is, like, your first time.” Valerie sat in a chair beside Harlow so she could watch.  Harlow sighed and finally wrapped his deep red lips around the cock. He started slowly at first but soon found a rhythm while Valerie filed her nails.

About ten minutes into the hour Valerie finally finished filing and spoke, breaking the painful silence, “Hold on.” Harlow took his mouth away from the dildo hopefully, “You’re waaaaay too quiet. You should definitely be, like, moaning. Guys love that stuff.” Harlow pouted and turned back to the fake cock, “Don’t forget to smile and touch yourself.” Harlow grimaced as he forced a smile to his face and inserted the dildo into his mouth yet again. He thought for a moment he would get some peace when she stood and walked into the living room but instead she would shout, “I can’t hear you!” He rolled his eyes and moaned loudly, keeping away from the dick suctioned to the chair in front of him. “I can also see you.” Harlow flushed at the new knowledge that from her position on the couch she could indeed see directly into the dining room. “Try that again and you’ll be out on the street corner with the rest of the trash.” She held a magazine in her hand and he thought maybe this would distract her, but he had no way of knowing if she was looking at it or him. Again he was trapped on his knees, forced to not only pleasure this sex toy but somehow himself. As he sucked on the wet dildo he began rubbing his fingers against the length of his small penis. It gave him a small jolt of pleasure which was subsequently killed by the sudden pain as his dick twitched and tried to harden, pulling painfully against his flesh. Any time he attempted to stop Valerie would “gently encourage” him by reminding him what would happen if he stopped.

For the next forty-five minutes Harlow rubbed his shaft as he practiced his oral skills, with frequent advice and help from Valerie. Tips like, looking in the man’s eyes as he sucked him off, asking if he liked what he was doing, saying phrases like, “Ooh baby, I want your cum so bad!” and “Cum for me!” repeatedly over the half hour from when she decided the phrases needed to be repeated if he couldn’t come up with his own. Despite the pain and embarrassment of his actions Harlow continued to feel his dick attempting to get hard to no avail.

When it was finally finished Valerie took two chips out of the jar, “There, that’s paid for. Don’t forget you have chores to finish today. I left your list on the counter. You can play with your boyfriend later.”

“Val.” Harlow asked weakly as he stood up, rubbing his sore jaw. “Can we talk?”

“We can talk when I get back from class. If you do everything on the list.” Valerie rushed out of the door.

Now alone, Harlow immediately tried to remove the dildo from the chair but found it too slick to get a good grip. Forced to leave it he instead looked at his chores list. He was expected to clean his and Daniel’s room, sweep, dishes, paint his nails and “...what the hell is P.E?” He wondered out loud. Surely she couldn’t mean P.E. like in school? And how was he supposed to do that in heels?! “This is fucking stupid.” He growled. Looking at the jar and the half dozen or so chips that remained checked to ensure the house was still empty before he reached in and grabbed three chips and quickly placed them in the small chip tray from whence they came. He was tempted to grab all of them right now, but even Val would notice an empty jar. But if he grabbed two or three every day she would simply think she had miscounted. Something she was surely used to at this point in her life. He grabbed a couple of paper towels and once again tried to remove the dildo he had spent the last hour drooling on. With a satisfying pop he removed it and was able to toss it in the bedroom before continuing with his chores.