Press Your Luck 25 (Patreon)

Danny sat on the couch early one morning, shutting off his phone alarm and stretching his back and his neck with audible pops in both. “I can’t keep doing this.” He mumbled to himself. His new job necessitated him waking up two hours earlier than he used to, which he had become accustomed to easily enough. What he still had trouble with was getting comfortable on the couch where he had been sleeping for the last several days.

Danny had apologized to Lucy that first night when she returned home. She had said it was fine, but there was still a distance between them that worried him. Had he really pushed her too hard too fast? Talking to his friends was no help: Harry simply said, “Women are crazy, man.” Ray pretty much said the same thing Valerie had, “You gotta talk to her about her feelings and shit. Just be honest and listen.”  Neither of his or Val’s advice made any sense to him. It felt a lot like lying to each other. Wasn’t that supposed to be bad for relationships?

One bonus of waking up early was it at least made it easier to avoid Lucy. Him being there couldn’t possibly help her deal with whatever was going on. When he came home at night she still cooked dinner despite the doctor telling her to stay on bed rest. “As if.” She’d scoffed the first time he brought it up, “I’ve been laying in bed so long, I’m like, going crazy. I need to do something.”

“Okay…but that’s it. After dinner go to bed. Okay?”

“No problem.” she said with her usual smile…but she didn’t look at him. She did everything she could to avoid looking at him. Whatever she was going through…he was the problem.

Finally one Saturday Danny couldn’t take any more and confronted his sister, “I can’t keep doing this.” He told her, “Is she wanting to break up with me or something?”

“What? Why would she?”

“Because I ‘pushed her’.” he said in air quotes.

“Not that she’s mentioned to me.”

“Then why’s she acting like this?”

“I told you. She’s still upset.”

“I apologized.”

“I know. But it’s no different than how she shows affection.”

“Then what do I do? Cause…”

Valerie frowned and hugged her brother. “It’s gonna be okay, Danny.” She said gently. After a minute they broke the hug, “I have an idea. We should go shopping.”

“Retail therapy doesn’t really help me.”

“One, surprised you know that term, two, we’re going shopping for Lucy. The doctor said once the swelling goes down her feet will be smaller. None of her shoes will fit after that.”

Danny sighed, “That’s as good of an idea as any I guess. At least it might get me off the couch.”

Weeks passed before Harlow was allowed to wear his own heels again. The doctors ordered him to stay on bed rest as much as possible, only walking to go to the bathroom or when otherwise absolutely necessary. The weeknights and weekends he enjoyed being waited on by Daniel and even Valerie though she still insisted he do his makeup even if he was only laying in bed. But during the weekday he was bored out of his mind. He could watch only so many soap operas and read his magazines before he started craving something more exciting. He hadn’t realized just how much of his daily routine centered around physical activities like yoga, dance, and even cleaning!  Harlow could not fathom how prisoners did not go insane. He was hardly a week removed from his latest routine, even one he hated, and he was already anxious to return to it.

After several days of absolute boredom he finally had enough and snuck into the kitchen to cook dinner. Daniel was still upset with Harlow despite cooking one of his favorite meals. “After dinner, go to bed.” He ordered.

“No problem.” Harlow nodded as he stared at his plate. Why didn’t Daniel just kick Harlow out if he were so disgusted by him?

Other than cooking dinner, the closest to a physical activity he got during his downtime was painting his or Valerie’s nails. He had managed to convince Valerie to get ‘his wedding planner’ started in exchange for doing her nails. Of course she took complete advantage of their deal and poked and prodded him for details about his new sex life. Excluding what he and Daniel got up to beyond Harlow telling her they had gotten as far as “Third base.” A fact she found shocking enough to probe Harlow with more questions about what kind of men he liked. She was determined to not accept “I’m not.” or “I don’t know.” as answers though.

Left with little else to do during the day in his first week at home Harlow picked up the book Valerie had taken from the hospital, continuing where he left off as the rugged farm hand first met the beautiful dancer when her car broke down on a lonely stretch of road during a thunderstorm. Unfortunately Thankfully Daniel hadn’t asked him for anything sexual while he recovered. Valerie was so kind as to remind him that if he and Daniel wanted to get physical all he had to do was ask and she would let him borrow the remover. Not that he would. He had some pride left after all.

‘Maybe she told him after all?’ He thought after the first week. ‘It would explain why he hasn’t, like, even tried to come to bed.’ He pouted as he closed his book and watched the door for a moment,  ‘Not that I want to cuddle Daniel of course, but a g-a person gets used to sleeping in a certain position with my arms wrapped around the big lug…just makes it harder to sleep any other way. Maybe he thinks I’m a freak too.’ He’d sigh and slip the book under his pillow before hugging himself to sleep the final thought, ‘I would if I found out Daniel was g-got turned on by turning men on.’

One Saturday night, before bed, Daniel knocked on their bedroom door. “Come in?” Harlow said with confusion in his voice.

Daniel walked in and quickly closed the door behind him. “Hey.” He said softly.

“Hey?”

Daniel frowned slightly and sat on the side of the bed, “Can we talk?”

“O-okay.” This was it. He thought as he slid to a spot beside Daniel. He was going to tell him to leave! He could barely walk and still they were going to kick him to the curb?!

“I know this is probably a little late, but I wanted…me and you…ugh…here.” Daniel said finally and placed a box in Harlow’s hands.

“What’s this?”

“Open it and find out.” Harlow slowly opened the box and his eyes slowly widened as a smile crawled across his face. Inside the box was a simple pair of pink lace five inch peep toe stilettos with a matching pink bow just above the heel itself. “What do you think?”

‘They’re, like, so super cute!’ He thought with a smile happily as he picked one heel up and examined them, “I can’t wait to wear them!” Lucy giggled with genuine happiness. ‘Fu-dge!’ he swore, sort of, ‘I’ve been, like, hanging out with Val too long! I’m starting to even think like a girl.’

“I figured…I thought it might be strange, ya know.” He cleared his throat, “I know you hate wearing them, but you did agree to wear five inch heels for me. People…might think it’s strange if my sexy girlfriend started dressing differently."

Harlow smiled and squeezed Daniel's hand, 'Finally.' he thought with relief, 'The big lug finally catching on.' How he dressed wasn't out of some secret desire, but a necessity to save his life.

Danny gazed deep into Lucy’s beautiful blue-green eyes, shimmering now with more green flakes. Her dark purple eyeshadow was as immaculate as ever. He didn’t like that she kept her surgeries a secret, or risked doing them all at once, but he couldn’t argue with the results. There was nothing more that he wanted than to take Lucy into his arms and explore every inch of her new body. He knew Lucy’s true age and even he thought she bordered on nineteen. He knew her true sex too and he still couldn’t tell. ‘Not true sex.’ He corrected himself, ‘What was it Val said? Birth assigned something?’ Before he could clarify his own thoughts he felt Lucy’s lips press into his.

Harlow stared up into Daniel’s eyes, watching as they roamed over his modified face with lust. Despite knowing the truth that what he was looking at was really a man Daniel still clearly wanted him. Harlow licked his plump lips as he thought, ‘He wants me.’ The thought still felt weird to him, ‘We made a deal.’ he reminded himself and pushed the feeling down. ‘I have to keep up my end of the deal after all.’ He locked the feeling away and buried it somewhere in the back of his mind where he buried all the feelings he didn’t want to deal with and leapt onto Daniel, wrapping his arms around the giant’s shoulders and kissed his boyfriend’s with a passion that reminded him of the escorts he had been with before. He wondered briefly how much of it had been forced and how much they actually enjoyed being with him the same way he enj-"Sexy?" she cooed in her breathy voice.

Daniel slipped his hands under Harlow’s purple cami top and dug his fingers into Harlow’s supple skin. The once loose top, like everything else, clung desperately to Harlow’s new breasts. Harlow rocked on Daniel’s crotch, enjoying the feeling of Daniel’s cock twitching underneath him even through his jeans. Daniel’s hand slid from Harlow’s back to his front, grazing the new chest underneath.

Harlow pulled back, breaking their kiss for a moment, gasping in pleasant surprise. For a moment they just stared at each other.

Danny feared he had done something wrong when Lucy stood off of his lap and locked the door. For a long minute she simply stared at him, her hands nervously playing with the loops in her denim skirt. “D-don’t laugh.” She begged. Before he could say, ‘he would never’, Lucy took off her top and bra in one smooth motion and tossed it into the corner.

In that moment he knew why she had begged him not to laugh. This was the first time he actually saw her breasts after her surgery. She was worried that what? He wouldn’t like them? He would be disgusted? What straight guy would be disgusted by boobs? “You’re beautiful.”

“Beautiful?” She asked, taking a step closer to him.

“And sexy.”

“Sexy?” She cooed, standing in front of him now.

“The sexiest woman I’ve ever known.” He gently took Lucy’s hand.

“Shut up.” She giggled, her face a hot pink matching the thong that peaked over the top of her skirt.

“Make me.” He pulled her back on top of him, both falling back onto the bed. Lucy’s breasts hung closely to Danny’s lips. She wasn’t much larger than she had been before, but now they had a realness to them that the breast forms lacked. Gently he caressed her breast. Again, Lucy gasped. Danny stopped until she nodded, licking her lips. The process repeated for several minutes, Danny becoming more and more bold. When he sucked on her nipple for the first time she moaned so loud both of them jumped to cover her mouth. Both sat in silence, trying to determine if Valerie had heard Lucy or not.

After a minute of listening to the silent house they both laughed together, figuring that Val must have gone out on a date. Harlow held a hand to Daniel’s chest, for a moment he stared at the broad chest of his friend. “Do you want to stop?”

He inhaled sharply, not realizing he had been biting his lip, “Huh? No. I, like, still need to pay you back.” he giggled and lowered himself to the floor, taking Daniel’s cock out of his pants.

Something in the back of Harlow’s mind screamed out to him that he shouldn’t be doing this, shouldn’t be enjoying it! They were men! Neither of them were gay! He shouldn’t be leaking precum into his panties just from sucking Danny off!

Harlow stopped, pulling his lips from Daniel’s cock. “Babe?” Daniel asked.

“Just…gimme a minute.” Harlow bit his lip, staring up at Daniel’s oversized cock. He swallowed hard and quickly reached to the nightstand and tore open a condom. “Almost forgot.” He rolled the condom over the tip of Daniel’s cock before placing his mouth over the tip and rolling it down his shaft with his mouth. He only made it halfway before he pulled back, choking and gagging.

“Impressive.” Daniel panted, “Where’d you learn that?”

“Ms.Lucia’s health class.” Harlow blushed as he rolled the rest of the condom down Daniel’s rod.

“Oh yeah. She was hot. Uh-I mean not as hot as you.”

“Shut up.” Harlow giggled, “She was hot.” Daniel’s laugh turned to gasps of pleasure as Harlow wrapped his lips around his cock. Hearing Daniel’s moans and feeling him pull Harlow’s hair as he took control turned Harlow on more than he cared to admit, even as he stroked himself through his pantied prison. Worst of all, in his mind, was he found himself missing the taste of Daniel’s penis not covered by a rubber.

Feeling himself edge closer he pulled Lucy by her hair, freeing her lips from his dick with an audible pop. “Get up here.” He ordered, tugging at the length of hair in his hand. She hesitated for a moment before biting her lip and climbing on top of his lap. He grabbed her ass with both hands, feeling her sitting over his crotch. For a moment he thought seriously about pulling her little pink thong aside and shoving his cock into her hole.

The worried but obedient look on Lucy’s face made him think better of it and instead he started grinding into her while sucking her nipples.

Harlow moaned loudly as he rode the edge of Daniel’s cock, both relieved and saddened that Daniel didn’t just put it inside of him. He knew he shouldn't want him too, he knew he shouldn’t enjoy dry humping his friend like horny teenagers. But as he listened to Daniel moan,his penis screaming for release as it drenched his panties, he could no longer help himself. Daniel’s hands moved to Harlow’s hips and he resumed his thrusting, slow at first, but soon his pace increased. Harlow bit his lip to hold in his moans of pleasure as Daniel sucked on his nipples. His own penis pulsed and twitched like mad in its prison, the precum running down his inner thigh. It began deep within him somewhere between his stomach and his crotch. With every twitch against the glue prison he felt the familiar sharp pain mixed with new found pleasure. Once the pain had slowed him down, it now added to the pleasure he felt as he exploded like a volcano that erupted out of his limp imprisoned penis.

Being that Danny was already on edge as Lucy rode his cock. Her voice as she moaned out his name was huskier than normal but still kept the Marilyn Monroe quality he had become used to hearing from her lips. Soon his primal urges took over and he picked Lucy up by her hips and used her like some living sex doll. After a few minutes of riding the edge of orgasm Lucy began to moan louder and louder, her voice rising in pitch with each thrust. The only thing he could think to do was pull her into a kiss. As their tongues danced he exploded inside of the condom before they both collapsed on the bed. Exhausted, spent, and content. For the moment.

Finally the day came when Harlow was no longer trapped in bed or the medical boots given to him by the hospital. “How’re you feeling?” Danny asked as Lucy stood barefoot beside their bed, finally freed from her “Ugly boots” as she called them.

Lucy pouted, “...weird.”

“Why?”

She shrugged. “I know what she needs.” Val exclaimed with a giggle as she handed Lucy a pair of heels.

“Oh goody!” Lucy cheered and sat back on the bed to put on her heels.

Harlow sat on the bed as he slid one foot into his chunky cobalt blue suede platform peep toe heel. When Val handed it to him he had responded sarcastically, despite his giggling, not wanting to tell either of them that it felt strange to be standing flat footed again or the fact he was happy to wear his cute heels again. But now something else felt odd as he slipped on both heels. “Um…” he pouted, “they don’t fit. Are you sure these are mine?” He asked, looking up at Val.

“Are you sure? Those are definitely yours, I don’t have anything that high.” Harlow pouted, he was a man and he wore higher heels than the bimbo. Val looked at Daniel, “You didn’t try them on and stretch them out did you?” They both giggled at the image of Daniel’s large feet forced into such dainty and feminine heels.

“Not for all the tea in china.” He smiled weakly. “The doc did say he reshaped your foot, remember?

Harlow pouted, his foot was already small enough to fit into an eight! How much smaller could they get?

“Try these.” Valerie grabbed a pair of white kitten heels from his closet. Again the same result. “Hmm…you’re gonna need more shoes.”

“What will I wear until then?”

“You could wear what I got you?” Daniel smiled.

“They don’t really go with what I’m wearing.” Harlow pouted as he stood flat footed in front of Daniel. He had gotten used to the extra five inches of height and felt suddenly like a pixie looking up at a frowning giant. “That totally came out wrong.” He took Daniel’s hand and pulled him down, “I love them.” He said with a gentle kiss, “I’ll just have to change to match.”

Valerie pretended to cough, “I should go…take care of this cough.” She coughed loudly once again as she left the room and closed the door behind her.

“What’s her deal? Not like she hasn’t seen me naked before.”

“She has?”

Harlow paused before giggling, “Like oh my gawd!” he shouted as the realization hit him, “You’ve both totally seen me naked now!”

Danny laughed along as he watched Harlow disrobe. He didn’t think everything Val had told him about Lucy so far had been completely accurate but he noticed that originally Harlow had either left the bedroom or made Danny leave before he would get undressed. At first he hadn’t minded himself, not wanting to see another guy naked, until he realized that Lucy was obviously not a guy. She was shy for the first week or so after her surgery due to the bruises and swelling but now that they had faded she didn’t seem to care that Danny was in the room as she changed for bed.

After he was sleeping in their bed again he found out Lucy had been spending her night reading a romance novel, even tearing up enough to keep tissues by the bed to dab at her eyes. He would’ve commented on it, not taking her for a big reader, let alone romance, but thought better of it considering what happened last time. And especially not when just before bed she would put her book away and kiss him before grabbing a condom and either giving him a handjob or a blowjob. ‘Just one of those things Harlow had to repress that Lucy no longer had too.’ He told himself. Like when he caught Lucy tearing up at a laundry commercial featuring a talking teddy bear and babies.

When Harlow was finally able to get out of the house he did not expect his return to civilization would be to the grocery store but Valerie had insisted he come with her. “After all,” she said, “we can’t keep spoiling you just because you’re totally super cute now.” Harlow simply blushed as he left with Val to the store.

Being out with Valerie felt strangely amazing, lighter somehow. Though he would never tell her that. Knowing her she would take it the wrong way and insist he do even more shopping with her. He had actually been feeling better the last few weeks since he returned home. At first he chalked that up to the medication, but when that ran out he just assumed it had to do with being away from the hospital. After they had gathered their groceries for the week Val pulled Harlow into the magazine section between the pharmacy and the registers. “What are we doing?”

“Duh. You’re, like, the one who said you were bored. So obvi we should get you something to read.” Val smiled as she placed a people magazine and an US weekly in the cart. “You should grab one of those recipe magazines while we’re here.”

“...sure.” Harlow walked down the aisle, picking up cooking magazines and skimming them for a few seconds before putting them back or not, depending on if he found a recipe that sounded good and one he might be able to make. Finding only two magazines he walked around to the other side and sadly only found books. Skimming the covers he stopped when he found a book titled Tango del Fuego with a latina woman in a beautiful red dress wrapped around a half naked man. Looking up, Harlow saw Val flirting with some dark haired man. With a blush he picked up the book and skimmed the first couple of pages.

“You find anything good?” Harlow jumped hearing Val yelling from behind the rack.

“Totally.” He coughed, pocketing the book. “A few recipes I could totally make on my own, but like, one or two I could…if you’d help.”

“Let me see.” Val walked around to Harlow’s side, noting the romantic smut books he stood in front of with an almost permanent blush to his cheeks. “Hmm.” She said examining the recipe he had earmarked, “Looks like a ton of work.”

“But, like, you can help, right?”

“Maybe.” She smirked.

“What do you want?”

“What’s the magic words?”

“Please?”

Valerie giggled, “So more than one word, cutie.”

Harlow giggled back, the pink that flooded his cheeks only making him appear younger, “Pretty please?”

“I don’t know…the deal’s not sweet enough.”

Instead of rolling his eyes out of his head, Harlow gave Val a side hug, resting his head on her shoulder, “Pretty please with sugar on top?”

Valerie couldn’t help but giggle at Harlow’s over the top performance, “Like wow, how could I resist such a cute young girl?” They both giggled, “I can totally help you.”

“Yay.” Harlow cheered with his permanent smile.

When Harlow and Val walked in the house that evening they found Daniel sitting in his usual chair. “H-hey?” Harlow swallowed hard. Maybe this was it after all. He could barely walk…Daniel wasn’t cruel enough to kick him out when he was still crippled. But now that he could.

“Hey.” He stood. “Can we talk in private for a second?”

Harlow bit his lip and looked to Valerie for help, “I’ll put the groceries away.” she said softly, taking the bags out of Harlow’s hands. Of course she was no help.

Daniel took Harlow’s hand and sat with him on the couch, “W-what’s up?”

“Firstly,” he started, “I need you to stay calm.” Harlow nodded as his heart leapt out of his chest and pounded in his ears like a war drum, “We had a visitor while you guys were out shopping.”

A little over an hour ago, Danny had just finished showering off the day’s heat when the doorbell rang. “Just a minute.” He shouted uselessly as he scrambled to find pants and a t-shirt. The bell rang two more times followed by a heavy fist pounding against the door with an all too familiar knock before Danny managed to answer it. “What’s up, man?” his voice was less aggressive than it had been on previous occasions.

“I hate to do this,” Marcus said with an apologetic tone, “but we gotta search your house again.”

“We?” Danny looked up from Marcus and noticed the lanky Oswald standing beside another man with a thick mustache he recognized but couldn’t recall from where. “Why?”

“We got a tip that your buddy Harlow was still in the area.”

“He’s not here.”

“I know.” Marcus nodded, “But orders is orders.”

Danny clenched his jaw and sighed before opening the door and letting the trio inside, “Just don’t break anything.”

“No problem, Jolly Green.” Marcus smiled as he led the two men inside, “You check the garage,” he told the mustached man, “you check the attic.” He told Oswald before heading towards the bedrooms.

Danny followed Marcus as he searched through Valerie’s room, “So who told you Harlow was here?”

“No one said he was here.” He checked the closet, slapping clothes out of the way and scanning for anywhere someone could hide in a pinch, finding dozens of new heels now overflowing the space it once had. “Got a tip not too long ago, said Harlow contacted him about getting some cash together.” Marcus came out of the closet and checked the bathroom, “Usually guys do that before they rabbit.”

Danny grimaced, was Lucy going to run away? Leave him and his sister to deal with all of this? No, Harlow…Harlow might have thought about it but Lucy wouldn’t do that. “When?”

“Couple weeks back.” He said as he walked out of Valerie’s room and into Danny and Lucy’s.

Danny followed, ‘Lucy called someone for cash.’ He thought, ‘Why?’ Money wasn’t tight anymore, she couldn’t possibly be risking exposure just because he was working for Jefferson’s brother-in-law? “Wait…a couple weeks ago and you’re just now coming to check here?”

Marcus sighed and faced Danny, “Like I said, I know he’s not here.” Marcus opened Lucy’s closet, noticing the distinct lack of shoes of any kind. ‘Weird.’ “ You got your new job,–” again he slapped the clothes around quickly scanning for hiding places,–“your gorgeous sister,–” he checked under the bed before glancing around the room and seeing a trash can full of tissues with several used condoms lying on the top–“your beautiful girl.”

Danny blushed. “Uh..that, um-”

Marcus held up his hand to stop the larger man, “I know what it looks like when a man just got out of the doghouse.”

Danny couldn’t help but laugh, “You got me there.” ‘He’s not entirely wrong.’

“I don’t see anywhere he could be hiding.” Marcus said walking out of their room and watched as Oswald descended the attic stairs, “Anything?”

“Just decorations and old comic books.”

“My comic books are still up there?” Danny gasped.

Marcus concealed a smirk and turned to Oswald, “Check on Fitzgerald.” Oswald nodded and left Marcus to close the attic door, “You’re not an idiot.” He said looking at Danny, “You got too much worth protecting to risk getting involved in his bullshit.” a frown came to his face, “Stay smart, okay?”

“No problem.”

Harlow sat frozen, his pink nails digging into his bare thighs. ‘‘I can’t believe Sam really did rat!’ his thoughts screamed. ‘Long as I live they just won’t stop looking!’ “-ucy?” ‘They’re gonna just keep coming!’ “Lucy?” Harlow shook his head and realized he had been staring in wide-eyed silence for five minutes.

“Are you okay?”

“....no.” She said weakly, “Th-they’re never going to leave us alone are they?”

“Maybe.”

“How?!”

Daniel struggled to find a believable answer that would help Lucy, but all he could come up with was, “I’ll figure something out.” He said hopefully.