Press Your Luck 11

Danny let the small girl pull him inside, ‘No..n-not a girl...right?’ Harlow pulled him inside, he was beyond begging for sex and Danny had let him pull him inside. Why? Even with his wrist hurting he could easily stop Harlow. But Lucy was so…sexy. “L-Lucy.”

“Shh, no talking, lover.” ‘Lover?’ Lucy pulled Danny into a passionate kiss that made him weak in his knees. ‘Fuck me.’ He gasped. ‘Okay…this is gonna happen.’ He chuckled nervously, feeling his cock trying to tear through his jeans.

Once inside, Valerie locked the door behind them, as Harlow closed the curtains. “Is he gone?”

Valerie peeked out of the small window in the center of the door, “He’s gone.” Danny jumped, having just realized Valerie was there.

His face burning bright red, “Ah, Val…I uh..forgot you were here.” He bit his lip as he looked to Harlow, ‘Should we get a hotel? I don’t know…seems kinda cheap.’

“Well yeah, where else would I be?” She rolled her eyes.

“Lucy, are you okay?”

Harlow nodded, “I thought I was gonna lose it but, like, Daniel played his part amazingly.”

“My part?”

“Yeah,” Valerie smiled, putting her arm around Harlow, “getting all flustered like you do when a pretty girl comes on to you.”

“Uh, yeah…I guess?”

“You did great.” Harlow hugged Danny before kissing his cheek. As he pulled away his eyes widened, realizing what he had done out of habit. “...Uh..I should see what we have to, like, ya know,”-Harlow giggled-“make for dinner.” he hurried into the kitchen with Valerie covering her smile as she followed Harlow, giggling along with him.

Danny stood in the living room alone as he watched his sexy girlfriend’s ass jiggle in her high heels. His cock still throbbing worse than the pain in his wrist. “I’m gonna run out of cold water at this rate.” He grumbled as he headed off to the shower.

The ice cold showers had proved little help in dealing with his situation, as soon after Lucy was once again in his lap, cuddling close to him and speaking softly into his ear in that breathy voice of hers. ‘She has to be doing this on purpose.’ He thought every time she’d shift in his lap, or put an arm around his neck, or ran her fingers through his short hair. ‘How did she not feel how excited she was making him? Or maybe she did and that was the point.’ For Harlow it was more than annoying that Danny kept getting hard like some teenager in class and no matter how he moved, he couldn’t get away from it. Val had made it clear, Danny’s lap was his seat, so there wasn’t much he could do about it. Somehow he survived the day and Lucy had fallen asleep before he had, her perky butt exposed by her sheer lace-up teddy.

Every time he tried to sleep he would see Lucy, sitting in his lap, completely nude. Every time she’d beg for him to take her. And every time he would reach out for her only to wake up in bed, his cock grinding into her ass and his hand hurting from squeezing her breasts. ‘Fuck this.’ He groaned and slipped out of bed. He grabbed his phone and silently walked into the bathroom, this time making sure to lock the door. Opening his phone he’d search his usual sight until he found a sexy redhead walking around her house in nothing but lingerie and incredibly high heels. It wasn’t lost on Danny that the pornstar he found looked similar to Lucy, other than her larger breasts and smaller nose. He struggled to pull his boxers down with his one good hand while the woman opened her door and found the pizza man, or plumber, or random dude, he didn’t care.  The man slipped his hands under her bra, squeezing her tits and kissing her neck. She cooed as she kissed the man. Danny sat his phone down, removing his brace, as the man reached into her silk panties. Danny gave his cock a few gentle tugs. In his mind he had replaced the man, kissing her long smooth neck, squeezing one of Lucy’s exposed breasts with his left hand, his right hand reaching into her panties and pulling her penis out.

Danny stopped as a sudden pain shot through his wrist, “Fuck.” he swore quietly, holding his injured wrist in his other hand. He watched more of the video in frustration. The man now stood in front of the woman, kissing and sucking on her breasts as he walked her back towards the couch. Feeling his cock twitch, begging for satisfaction, he massaged his hand as the man laid the woman down on her couch, preparing to slide his large cock into her waiting hole. Danny tried again, wrapping his hand around his member only for the same pain to shoot through his entire hand again. ‘Fuck, must’ve tweaked a nerve.’ He frowned and unfortunately closed the video before starting up yet another cold shower.

Some hours later, Danny felt the weight of the beautiful girl next to him shift. Her leg curled over his waist. “Hi, lover.” She whispered as she kissed his neck.

“This again?” He groaned.

“Why not again?” She kissed his bare chest.

“You’re not real.” He looked at the beautiful woman, now sitting astride him as he slipped an arm around her naked hips.

“Then what’s the problem?” Lucy ran her hands through the hairs of his chest, rocking her hips back and forth.

“If she ever found out…she’d freak.”

She kissed his lips softly, “Real or not, we can still have fun. You can do whatever you want to me and she’ll never have to know. Though keep in mind she didn’t care what happened the first night you were in bed together.” Lucy slowly traced her face over Danny’s, like a predator sniffs its prey to ensure it was safe to eat. “She wants it as bad as we do.” She whispered in Danny’s ear before sitting up and slowly rocking on Danny’s bulging cock.

Danny thought for a moment, “You’ve got a point.” He smirked before pulling the woman down onto him and kissing her passionately. If he couldn’t have the real thing, at least dream Danny and Lucy could have some fun. She rocked her hips more feverishly as he continued kissing her, his free hand pulling his boxers down. He would normally concern himself with foreplay but he didn’t know when he would wake and didn’t want to risk losing this moment. Even if it was just a dream.

“Let go, Daniel.” She moaned in his ear.

“I’m about to, baby.”

“Let go.” She bit his ear. “Let go, Danny.” She begged louder. “Daniel, let go!” She yelled.

Danny woke to find Lucy straddling him, grinding Danny’s crotch, his arm around her hips. Realizing he was awake he let go of Lucy and she rolled onto the floor with a thud. “Ow! Fuck.” She hissed.

“Are you okay?”

“No.” Harlow growled.

“What were you doing?”

“Me? I was trying to go to the bathroom and you pulled me down on you.”

“You had to straddle me to do that?”

“It’s the only way to get out of that bed. We really need to talk about rearranging this place.”

“Okay.” Danny let the lie settle. He knew it was difficult to get out of the bed when you were with someone else, and maybe he grabbed Lucy in his sleep, but that grinding felt almost real.

The next morning, Harlow’s routine had remained unchanged. Getting up earlier allowed him brief minutes alone until Valerie got up. As he was cooking breakfast she came into the kitchen, “Morning, Lucy.”

“Mornin’ Val.”

“How’s your baby doing?”

“Huh?” He turned away from the eggs he placed onto a plate to look at Valerie.

“Daniel?”

“Oh. Uh…fine I guess?”

“Did you check?”

“N-he felt fi-I mean he looked fine.” Harlow blushed as he remembered Danny’s hands pulling at him just a few hours ago.

They both heard the familiar sounds of Danny’s shower running. “You need to check, remember?”

“I will.”

With a sly smile Valerie went into the cabinet and took out a glass, poured some water, and took out a bottle of over the counter pain meds she kept in stock just in case, “What kinda girl are you sending the husband you love so much off to work in pain.”

“He’s my boyfriend. I mean…we’re not married.” His face burned red as he quickly took the plates into the dining room.

“Silly me.”

A few minutes later Danny entered the dining room to the now usual sight of Valerie and Lucy sitting at the dinner table and his breakfast ready to be eaten. Lucy immediately stood from her seat and inspected his hand before he even had a chance to speak. “How’s your hand?” She asked softly.

“It’s fine.” He lied. After last night’s attempted masturbation session his hand hurt worse than before. The doctor had assured him it was just a sprain, but he should still refrain from using it as much as possible.

“Liar.” she cooed softly, gently massaging his bare wrist. His brace forgotten and left in the bathroom while he showered. Once again she gently kissed his wrist, making a trail to each finger. He thought briefly about breaking his wrist so she’d never stop, but thought better of it. “I have something that’ll make you feel better.”

“Yeah?” this morning he couldn’t contain his goofy grin.

Lucy nodded and sat him in his usual chair. She placed the pain relievers next to Danny’s morning glass of orange juice. “Take these. They’ll, like, help. I think.” Harlow said, tilting his head from one side to the other and bouncing a little.

Danny chuckled, ‘She’s definitely doing it on purpose.’ he thought as he took the pills.

During breakfast the pair watched Danny struggling to eat with his left hand, the other not as used to it as his right. Harlow watched impatiently, he wanted Daniel to hurry up and leave so he could put as much distance between him and last night as possible. Last night it had taken him over a half hour to eat his dinner. “Here.” Harlow said finally in frustration and took Danny’s fork.

“What are you-”

“Shush, baby.” He intended to sound more insulting as he changed seats to sit beside Danny but with his gentle voice and constant smile, he sounded as if he was calling him a pet name. He cut a piece of sausage, stabbed it and scooped some egg onto the fork before offering it to Danny.

“I can feed myself.” Danny argued.

“I want to help. Now open up or I start making airplane noises.” Danny looked between the fork full of food and Lucy in confusion, but he relented and took the offered bite. He learned long ago it was better to not argue with your girlfriend on minor issues. And he didn’t have time to fight  over something so trivial. So Harlow sat the rest of breakfast beside Daniel, taking turns feeding him and feeding himself.

Later, as Danny was leaving Harlow rushed out to meet him at the end of the drive again, “Daniel! You forgot something.”

“I did? I’m sorry.” He didn’t think he had, but he pulled Harlow in and kissed him lovingly on the lips. The kiss lasted for ten seconds before he released Harlow.

“Not that.” He blushed, giggling with a mix of anger and anxiety. “This.” He handed Danny his forgotten wrist brace.

“Oh.” He laughed. “What would I do without you?”

“Be incredibly bored.” Harlow smiled. If nothing else, he brought excitement to his friend’s life. As he was fond of reminding his friend over the years.

“I suppose I would.” Was his usual response, but the way Danny looked at Harlow made him blush again. It sounded different. It felt different. Softer. “I should go. I’ll see you later tonight, okay?” Harlow nodded. Danny once again pulled Harlow closer and kissed him again, and Harlow was unable to stop himself from giggling before Danny drove away. Still feeling the blush on his cheeks, Harlow reminded himself why they were doing all of this and took a look around the street for any cars he would recognize that belonged to those he was avoiding. He didn’t see them, but they could also just be in a vehicle he didn’t know. Shaking his head he told himself the ruse was working, if it wasn’t he would have broken legs or would be dead.

For a brief moment, Harlow thought he was safe. Save for simple cleaning chores he had no plans for the day, and no way Valerie would want to go to the mall again. But as he was finishing washing the dishes Valerie returned dressed for going out. “Alright, Lucy. We need to get you ready.”

“Ready for what?” Harlow grimaced for a moment but quickly rebuilt his smile, hoping Valerie didn’t notice.

“Your doctor’s appointment, remember?”

“...no?”

Valerie just rolled her eyes, “Just follow me. I swear, you’re,like, such an airhead sometimes.” She giggled. Harlow giggled and followed the true airhead into her room.

As Harlow sat in front of the vanity mirror he caught himself pouting, ‘I already did my makeup and dressed myself. What else could she want?’ Harlow had once again woke up before Valerie, considering himself lucky he got started in his routine and enjoyed the relative silence. No annoying bimbo knocked on the door every five minutes to remind him to wash his beautiful hair, or shave his ugly beard, not that it even grew that quickly but she wanted to make sure he had no signs of stubble, which meant plucking the few arrant hairs that tried their best to grow. Which was incredibly tedious on some days and utterly painful on others. He vowed, once all of this was done he would grow a full viking beard, to make it up to all the little beardlings that never got their chance at life. For now though, he considered asking the bimbo about if nair could be used on his face.

In Danny’s room he had quietly slipped on one of the many thongs Valerie had purchased for him, Harlow having exhausted his supply of more comfortable panties earlier in the week. He stood in front of their shared closet as he searched for a halfway decent outfit that wasn’t completely slutty. He had agreed to dress sluttier for Daniel but…he wouldn’t be home for most of the day so he could probably get away with something simpler until he came home at least. Every rustling or moaning sound Harlow heard from Danny caused him to glance back at the sleeping giant and remember the events of last night.

He had woken up sometime early that morning, desperate for the bathroom and had no choice but to take the quickest route over Daniel. As he crossed over his sleeping friend he felt something tugging against his crotch. Something from that stupid teddy Valerie told him to wear was caught on the button of Daniel’s boxers. Blind in the dark he first reached for the source of the tugging, and found only his disturbingly smooth crotch. He dug deeper underneath and found what felt like the button. ‘It’s somewhere around here then.’ He thought as his fingers traced the button. As he blindly searched for his release he found Danny’s bulge slowly growing underneath. ‘Dude, really!?’ He screamed silently as his hand grasped his penis and quickly let go as if he had grabbed a hot poker. ‘You really need to get laid.’ He shook his head but forced himself to continue. The only way out being forward after all. He’d rock back and forth trying to give himself more room, just when he thought he found the thread Danny’s arm wrapped around his waist and he was pulled down into a deep kiss from Daniel. Daniel’s cock pressed hard into Harlow’s now trapped hand as he tried to pull himself free but as always found himself no match for the strong man underneath him even with his busted hand. Trying to wriggle himself free was a mistake. With his hand pinned to his crotch, moving at all only caused him to grind against what little of his own penis he could reach. Every twist, push, and pull only caused pain as his dick tried to free itself from its sticky imprisonment as it tried to expand from the stimulation. A painful reminder he really needed to get laid too.

Finally he was able to free his own hand, feeling Daniel’s growing cock pressing into his own neglected penis. “Let go!” He whispered, trying to pull himself backwards only for Daniel to pull him back down with his other arm by wrapping it over his shoulders. “Let go, Danny!” he begged in the slumbering giant’s ear. Harlow’s heart pounded and he bit his lip in frustration, “Daniel, let go!” he all but yelled in his friend’s ear. Suddenly he was thrown from the bed and he landed with a thud on the floor below, before getting up to his heeled feet. He hated it, but wearing them to bed kept his foot from hurting

Harlow turned away from his sleeping friend and quickly picked something that, according to Valerie’s magazines, went together and left to quickly dress in the bathroom. ‘Fuck Danny. I need to get laid.’ He thought as he slipped on the high waisted leather black miniskirt. ‘Soon.’ He smiled, remembering Naomi’s invitation. Soon he’d not only have sex again, but he’d join in a threesome. If he played his cards right he could get released from his sticky prison without Valerie ever knowing. ‘She would just find some way to ruin it.’ he thought as he slipped on the purple lace camisole with its deep plunging neckline and thin straps he showed an amazing amount of skin, but it was so damn hot and he wasn’t going anywhere so he’d be fine.

That’s what he thought anyway, but now he was going to some appointment? He balked as Valerie tried to wipe his face clean, “I already, like, did my makeup.” He whined.

“I know, and you’re getting pretty good at it,”-Harlow felt himself smiling with pride-“but remember I said there were five looks you needed to master?”

“Yeah?”

“Consider this graduation.” Valerie smiled. “You finally made it to second grade. Yay!” She giggled. Despite his face burning with humiliation and anger he giggled along with her.

“Yay.” He cooed sarcastically.

“That didn’t sound like a smile.” She furrowed her brows.

“Huh?” His eyes widened.

“Okay, pro-tip, girly. It’s not enough to just wear a smile. People can tell you’re faking by the sound of your voice.”

“You didn’t say anything before.”

“Like I said, it’s graduation day. So, it’s important you not only look happy, you sound happy. And you should use….happier sounding words, okay?” She almost slipped and said ‘Excited’, but Harlow thought she was a bimbo and she still needed to play that part until she was sure Harlow was stuck in his prison of stupidity.

“Okay.” He said blandly with his practiced smile. Valerie’s pursed lips told him he had done wrong and was expected to start immediately, “I mean, like, totally!” He practically cheered.

“Perf. Now come on. I want you to, like, get some practice in before we go.” The pair spent the next two hours doing and redoing Lucy’s makeup. Valerie showed him the techniques once and expected him to pay attention. Each time he made a mistake he had to wash it off and start again. There wasn’t much difference in foundation as they were going out during the day, the harder aspect for Harlow had been the different level of contouring and highlighting now expected of him. Either his nose looked too thin, too wide, or simply wasn’t blended well enough. Now under his bottom lip needed contouring and his top needed more highlighting. His first attempt resulted in a badly drawn van-dyke. After a few more tries he saw what a dramatic change it made. His already plump lips looked even larger and so inviting he felt himself stirring just looking at himself in the mirror as he imagined the slutty bimbo’s lips wrapped around his cock.

The next challenge came with his new eyeshadow; before he had only done simple, singular, colors, now he needed to learn to blend multiple and contrasting colors together to create a coherent look. Repeatedly he added too much or too little and he either ended up looking like a clown or a mugging victim. Checking the time Valerie sighed, “You’ll just have to work on that more later.” Valerie washed his face one final time and once again redid his makeup. She did more makeup in the past two weeks than she ever remembered doing in high school. Of course she was a natural beauty and needed little help from makeup.

As Valerie finished Harlow’s makeup, an idea struck him, “What about my lipstick?”

“What about it?”

“The kiss test? Danny’s not here.”

Valerie smiled, knowing exactly what he was getting at. “Good point.” She cooed, standing Harlow up.

‘It worked!’ he smiled.

“I haven’t done this in a while.”

“M-me either.” he giggled nervously. ‘Why did I say that?!’

“You kiss my brother all the time.”

“I meant-”

“I know.” Harlow leaned in to kiss Valerie but she pulled back at the last second, “Last time I did this was with Naomi.”

“R-really?” His member pulled painfully against the glued prison.

Valerie nodded, “She’s a great kisser.”

“I’ve not gotten any complaints.” He smiled.

“Yeah?” She asked softly.

“Yeah.” This time Valerie leaned in, turning her lips to his ear, “Tell me something else.”

“What?” he begged quietly.

“Something else you like about yourself, Lucy.”

“Uh…”

“If they’re good enough…I’ll let you do more than just test your lipstick.” They both giggled.

“Um, like, my boobs are sexy as hell.”

“They are.” Valerie smiled, giving them a playful squeeze Harlow briefly wished he could feel.

“My…my ass. Looks really good.”

“Right you are.” She smiled and this time squeezed his butt sending pleasure and pain throughout his body. The sexy cheerleader grabbing his butt turned him on and in doing so his dick twitched, pulling painfully in its prison once again.

“My…lips.”

“Yeah?”

“Yeah…” He had half expected her to kiss him immediately, but she just continued staring at him, licking her own lips.

“What do you like about them?”

“They’re…uh…sexy?” He blushed, giggling nervously.

Valerie giggled and bit her lip, “Sexy how?”

Harlow stared at Valerie’s lip, hungrily, imagining her lips on his member, “I’d love to feel them in action.” Harlow bit his lip, ignoring the pain in his crotch, tilted his head to meet Valerie’s lips. This time Valerie didn’t pull away, she leaned in closer her lips nearly brushing his. Harlow closed his eyes and pressed forward. His lips making contact with her cheek.

Opening his eyes, he saw Valerie looking at her cheek in the mirror. “Welp, they pass the test.” She smiled, turning back to Harlow.

“I thought you said-”

“I know what I said. But remember I told you to tell me three things you like about being Lucy.” Truth was Valerie herself couldn’t remember if she had told him to do this before, but it was something she wanted him to do, so she probably had.

“I did.”

“No, silly.” She smirked. “You told me you like certain body parts. Doesn’t count. Unless…do you like being sexy?”

“Y-yes.” He lied.

“Okay. That’s one, but you need to say it, And what else?”

“Uh… I, like, totally love that I’m sexy! And… uh…”

Valerie giggled, “You can try again tomorrow, okay?” Harlow giggled as he nodded his head, “Right now, we need to go.” Harlow took a final look in the mirror as Valerie dragged him away. The final eyeshadow ended up being pink and glittery with hints of purple to create shadow and white to create light. He almost missed the normal “everyday” makeup he had been doing. At least he looked like a regular girl. Now? Now between the makeup, the mini-skirt and five inch heels on his feet he looked like a woman on the prowl.