Press Your Luck 15 (Patreon)

Waking up early the next morning Harlow, having slept deeply through the rest of the evening. He wasn’t sure exactly when he fell asleep or when Danny had gotten up but in the early light the next morning Danny had obviously showered and changed clothes. Danny’s boxers were different, he wore no shirt, but his hair was cleanly washed and still slightly damp, his face was clean shaven and he smelled nice, sharp and crisp. He couldn’t quite place it but the smell put a genuine smile on his sleepy face and invited him to lay back down and soak in the pleasant aroma. Was he wearing cologne in bed? Why? Harlow wondered as he sat up. Danny had no blanket for covering, he simply held Harlow close to his chest, Harlow’s own arm had wrapped around Danny’s broad chest at some point in his unconscious state.

Harlow had gotten over the fact he woke up most mornings cuddling his best friend, chalking it up to being touch starved. He heard somewhere once that humans needed at least ten to fifteen minutes of hugs per day in order to regulate. Before this the last time he had received a hug was three years ago when he booked his mother on a cruise for mother’s day and birthday, both falling on the same week. He had won two tickets at one of his regular casinos, of course when he found out he couldn’t cash in either ticket he was stuck with them, he did learn that he could upgrade the two simple cabins into a single luxury suite. So it was fine, and even natural, that he found some comfort in being held by Daniel, even if he knew he shouldn’t. Just like he had enjoyed the bath for its warmth as well.

Harlow was forced to slide over Danny, yet again, if he wanted to leave the bed in the heels he still wore. Climbing out of the cramped bed was hard enough in bare feet but it was nigh impossible in heels. Sliding over Danny he felt the slumbering titan shift, “Ready for round two, Babe?” he said softly, still half asleep, his eyes still shut, yet awake enough to pull Harlow down onto his chest.

“Go back to sleep, ya horse.”

Danny smirked, “Yeahbaby! Youknowit.” He let out a single soft laugh as he fell back to sleep.

Harlow giggled back and shook his head with the smile that became far too routine as he tried to pull himself away. Pulling himself upright, putting one heel on the floor, he felt Danny’s cock grind into his exposed ass. His smile once again fell away as yesterday flashed in his mind like a trailer to a movie he hated. Worst of all he had a starring role.  He trembled as it came flooding back, bits and pieces all at once! He had fucked himself with a dildo! Harlow quickly threw himself off of Danny’s crotch and rushed to the bathroom as his stomach twisted into an Edwardian knot. ‘I wasn’t that drunk was I?! Jeez my ass hurts too!’ His mind screamed in the quiet bathroom. 'She did this somehow…she got me drunk and tricked me…' As much as he hated to admit it he could remember Valerie leaving and him continuing to pleasure his hole with the rubber cock and giggling with pleasure. “I’m not gay.” he said gently to himself in the mirror.

As if his penis wanted to argue the opposite, he felt his cock throb, and Harlow noticed for the first time his skirt had a tentpole poking straight out. “Man, what a bad time for morning wood.” He told himself and quickly turned on the shower, as cold as it could possibly get. He knew for certain he wasn’t hard thinking about having masturbating with a dildo, it was just his usual morning erection, something he hadn’t seen in awhile because Valerie had glued his dick away. “...Did she give me the remover?” He wondered, as he stripped naked. He didn’t remember a lot about last night, and his thoughts were still a jumble with what he did remember. But he could say for certain Valerie was incapable tricking him, as smart as he was and as dumb as she was. Looking back in the mirror at his bare breasts he wondered if she had given him the remover then why wouldn’t he also take off the fake breasts? Of course, he had been so damn horny lately, maybe he just didn’t think about taking them off or maybe it had been part of the deal or pay for losing. He had to assume he lost otherwise he would have woken up with Valerie and definitely not Danny.  With a shiver Harlow got into the shower, taking special care not to put too much pressure on his foot, he briefly considered a bath but decided against it, his bath was significantly smaller and he didn’t have the set up Valerie did.

After his shower Harlow went ahead and wanting to get more practice with his makeup and not wanting to go back to bed with Daniel for fear of what might happen, he washed his makeup clean of last night’s smeared makeup as Valerie had shown him dozens of times now. It was almost second nature by now as he painted his face with light and casual makeup. It wasn’t until he finished that he realized Valerie would give him shit for not practicing the new style. Which didn’t make a lot of sense to him, shouldn’t he just practice it at night? ‘...No. That’s double the times I gotta do this.’ He told himself and washed his face again. This attempt took more concentration to get correct. As he was tracing the deep red lipstick across his pouty lips a memory flashed behind his eyes of his same lips wrapped around Danny’s cock. Harlow shook the thought away immediately, smearing lipstick on his cheek. “What the hell?!" Starting over his makeup fared better this time, his blush was a little subtler and his contour a little more control. He almost felt proud, until he realized he was a man proud of his ability to do slutty makeup. Again as he passed the lipstick over his lips he thought ‘It’s too bad Daniel’s not awake so I can go ahead and test it.’ Not that he wanted to kiss him of course, it was the stupid rule that Valerie insisted he did. With that thought came more memories, kissing Danny as he rocked his own hips on Daniel’s cock. Again he scrunched his face, turning away as if the thought was in front of him. “Son of a-” he growled and washed his face yet again. Before he started again he found a tent under his towel. “Stop that.” He hissed. He was having these weird daydreams about being fucked by Danny and his dick was getting hard?! “We already…” he let the thought die. Telling himself he already had masturbated would mean having to admit he had fucked himself with a dildo, and he enjoyed it enough to orgasm. 'Nope.'

This time as he did his make up again he steered his thoughts to his upcoming threesome with Naomi, and possibly Candy. He messed up a few more times and his dick was still hard but at least it was more appropriate, at least that’s what he told himself.

By the time Harlow finished his makeup an additional three times, each time his fantasizing about Naomi caused him to make obvious mistakes he knew Val would chastise him for it and redid it each time. Finally he felt it was good enough so he crept back into the bedroom to not wake the sleeping man and picked out an outfit for the day.

After doing all of that he had just enough time to start breakfast before Danny woke up. Surprisingly he didn’t go to the shower, instead he made a straight line for Harlow. “Hey, sexy.” He smiled as he wrapped his arms around the much smaller Harlow and kissed the back of his neck. Harlow felt his penis stiffening again. “What the hell?” Harlow giggled anxiously as he pulled himself free.

“Uh-oh, you owe a quarter to the swear jar.” Valerie said as she joined them in the kitchen, already dressed for the day.

“Swear jar?”

“We talked about it yesterday, good girls don’t use foul language.”

“...whatever. I don’t have a quarter anyway.” Harlow frowned with that realization. As Danny ignored their conversation, his hands taking a tour of Harlow’s flat tummy exposed by his crop top.

“It’s fine. We’ll use poker chips for now.” Valerie smirked as she went to the laundry room to pick up a stack of five dollar chips. “ When you get enough you’ll have to do a punishment.” She ignored Danny trying fairly obviously to not feel up Lucy in front of her and threw a chip into an empty mason jar before walking into the dining room.

“Wha-Can I help you?!” Harlow said pulling away just enough to turn to face the man.

“I’d like to think we can help each other.” He pressed his lips against Harlow’s. Instinctually Harlow slipped his tongue past Danny’s lips. Kissing Danny warmed his face, especially when Danny’s hands grabbed his ass and lifted him onto the countertop.

“Daniel!” Harlow hissed, pulling himself away from Danny’s lips. “What are you doing?”

“I thought that was pretty obvious.” Danny chuckled.

Harlow giggled, “Don’t you have work?”

“Yeah…I can take a day off.” He smiled.

“Just to jerk off?”

“I can’t, remember?” He held up the wrist brace.

“Well…sucks to be you.” Harlow started to push himself off of the counter but saw the strange bulge under his skirt. Not wanting to give his friend the wrong impression he simply stayed in place, covering his crotch with his hands. His five inch heels were able to reach the floor with little effort but now they were rendered useless..

“...I mean…after yesterday I thought-”

“What?!” Harlow hissed. “I don’t know what you’re talking about.” Harlow’s face burned now in embarrassment.

“Yesterday you-”

“Daniel…” His soft breathy voice begged and his lips pouted without him realizing he had done it, “I know…okay? But can we just…,like, pretend it didn’t happen okay?”

“You want me to act like it didn’t happen?”

“I was drunk, okay?” He looked up to the still taller man, his lips pouting, his eyes pleading to his friend.

“...Okay.” Danny walked away, not letting Lucy see the frown on his face even when he stopped at the door and turned back to her. “Are we okay?”

Harlow dropped his shoulders, “Of course. You’re still my best friend…right?”

“Always.” He forced a half smile to his face and left the kitchen.

After Danny’s shower he refused Harlow’s comforting kisses on his injured wrist while he ate his breakfast in silence despite his sister’s best efforts to engage him. Harlow was again rejected as Danny left without kissing him goodbye. No, not rejected, he wasn’t a boyfriend that refused to kiss his girlfriend goodbye. They were friends, he was helping out by playing a part…but he was upset about something and forgot to play his part…if this continued…that’s all. He was worried about his safety. “Is everything okay with you two?” Valerie asked, putting a book into a bag.

“I…yeah. We’re fine.”

“Then why’s Danny so down? I would’ve figured after yesterday you two would be-”

“We’re not gay, damnit!” Harlow shouted.

“Chip.” She glared angrily. “Now.”

“Fine.” Harlow picked up one of the chips from the counter and dropped it in the jar. “Still not gay.”

“Sit down.” Harlow felt his bones jump back three feet. Her usually bubbly voice was gone. It had been replaced by something sharper than he had heard from her before. He was sure she was about to kick him out, even after everything he had done so far just to appease her?! Valerie glared down at Harlow as he smoothed his skirt out and sat in an empty chair. “What did you do?”

“Nothing.” He lied.

“If you lie to me again I will drag you back to your apartment and leave you there. After I put a call into Marcus. We’re doing this to help you.”

He had gotten used to her being nice and cutting him slack when he wasn’t perfect at being Lucy. He almost forgot what a vindictive streak she had when it came to people she cared about. “Okay.”

“Now, what’s going on with you two?”

“I don’t know…I mean…after yesterday-”

“So what?”

“I’m not gay.”

“Who gives a shit?!” She yelled.

“Ah..chip…” he tried pathetically.

“I’m not a lady right now. I’m your judge and jury, if you’re not careful I’ll be your executioner too. Now as far as this homophobia business, it stops now.”

“I don’t hate gay people. I’m just not one of them.”

“Label yourself whatever you want. But tell me the truth, did you enjoy what happened yesterday?” Harlow opened his mouth and was immediately cut off by Valerie’s cold voice, “Remember what happens if you lie.”

“...I guess…a little.”

“All the moans I heard when I came back, it sounded like more than a little to me.” Harlow pouted and stared at his black five inch heels, his eyes moving across each of the black straps. Valerie sighed and sat next to him. Softening her voice she started again, “If you liked it, why is Danny upset?”

“I really don’t know. I just asked him to forget about it cause I didn’t want him to think…”

“You’re afraid he’ll think what? You’re gay? You liked it? You want to do it again?” Harlow blushed but nodded. “How many relationships have you had like this?”

“I don’t know. You said Lu-I had a few but…”

“Fine. How many did Harlow have?”

“....none.” He pouted. “This…” Harlow let out a breathy giggle as he spoke at the ridiculous notion, “This is actually my longest relationship.”

Valerie managed to keep her giggling inside, “It’s scary isn’t it? Serious relationships.”

“...Kind of.”

“But you’ve had sex before.”

“Mostly with e-escorts.” he dug his pink, chipped, nails into his leg. He wasn’t ashamed of it before, but admitting it to Valerie he somehow felt…smaller.

“I get it. I haven’t dated in a while. The longer it takes…the scarier it gets. But-” Valerie’s phone beeped. She peeped at her alarm, telling her she needed to leave now or she’d be late for class. She pouted as she put her phone back in her purse, “Would you want me to explain things to Danny?”

“You’d do that?” He perked up, he never liked discussing his feelings with anyone, let alone other guys. As short and spinly as he was, everyone teased him for being a girl.

“Totally.” Valerie stood and picked up her bag and purse. “But, I want you to clean while I’m gone, and for god’s sake fix your nails.”

“Fair.” Harlow giggled. If it meant he didn’t have to talk “feelings” with Danny, and for his friend to stop being mad at him for some weird reason then painting his nails and sweeping was a small price to pay.

Valerie had given Harlow a quick rundown of what she expected, and where he could find everything he would need. “Since you’ll be doing a lot more than dishes today, you should wear this over your dress.” She said, practically forcing an apron into Harlow’s hands.

“Really?”

“Yes.” She said matter of factly before moving on. Before leaving she had handed him an actual chores list that included everything from dishes to laundry.

With the frilly white apron tied over his green dress and matching five inch heels he shook his head and giggled. ‘If I had a string of pearls I’d look like a slutty June Cleaver.’ He thought when he caught his reflection in the bathroom mirror as he cleaned the sink and counter.

In the kitchen he mopped the floor with an old sponge mop that would fall apart if he pushed too hard. “Stupid thing.” He groaned after having to re-clean where he already mopped just to pick up what was left behind by the ruined mop. “Soon as I get some money your days are numbered.” He threatened the mop as he continued cleaning the floor. Finally finishing he made a horrible realization. He had mopped the kitchen floor and it was spotless…and he was trapped in the corner beside the refrigerator. “Shit.” He swore. “I, like, totally gotta put a chip in the swear jar.” He mocked Valerie as he rolled his eyes, thankfully the bimbo wasn’t there to hear him or swearing or mocking her.

With no other recourse he was trapped in the corner, forced to stand in his painfully high heels while he waited.

After a few minutes he got bored and looked through the contents of the refrigerator as he thought about what to make for lunch when he was freed from his self imprisonment. ‘I already make him breakfast and dinner, maybe I should make Danny’s lunch too.” He thought for a moment as he eyed the sandwich meat, “Yeah, then he can afford a new mop!” he said to no one, closing the bottom door before opening the top freezer. “Oh wow!” He cheered, pulling out a ziploc bag of frozen pork chops. “Danny loves pork chops!” He smiled as he thought about making them for dinner as an apology for the morning incident. He didn’t like seeing his friend upset, and this would certainly put a big smile on his face. “Ooh!” He cooed, putting the bag back in the freezer and taking out a bottle of cold vodka. “Hah! I know what I’m having for dinner.” He giggled.

After being freed from the corner he was able to resume his chores for the day. He picked up the discarded clothes in Danny and his shared room. Feeling awkward as he picked up the discarded thongs he had left lying around. Putting the clothes into the dryer was another struggle as it was a top loader and even in his five inch heels he was barely able to retrieve the clothes stuck in the bottom of the washer without stretching himself further than he thought he was capable. “Stupid piece of junk!” He shouted into the washer as he struggled to pull himself out of it, barely keeping a single toe on the floor. An hour later, after he had his lunch, when he went to get the clothes out of the dryer he was dismayed to learn the dryer had been overloaded and would require multiple dryings before it fully dried anything. “Old piece of–'' He swore as he slammed the lid shut and started it once again. “Ugh…I need a nap.” He groaned, pulling off his heel for a moment and attempting to massage the pain away. He checked the chore list and realized he was only half done. And she still expected him to have fixed his nails by the time she got home according to the very last reminder on the bottom of his chore list. With nothing else to do while he waited he went into his bathroom, finding the multiple bottles of nail polish and paints Valerie had bought for him he searched for a color that would match his nails and painted them at the dinner table while he waited on the laundry to finish. Valerie of course intended for him to simply fix the chipped pink paint on his nails but he had a better idea. Finding a color to match his nail it would blend in and hardly be noticeable. And she couldn’t blame he-him if he simply said she should’ve been clearer. After cleaning off his nails he picked up the small jar of nail polish, “Pomegranate red.” He said before shaking the tiny bottle, “Bet that bimbo couldn’t even spell Pomegranate red.” He giggled. He thought for a minute as he continued to jerk the jar, “P.O.M.A.G.R.A.N.I?T.E.” he stopped and read the black swirled script label once more. “Eh, bad example that one’s tricky. But still.” He excused himself, unscrewing the top and went about painting his nails with the dark, glittery, red liquid.

Danny was sitting down to lunch in the breakroom, grease, soot, and sweat on his arms and chest, his face contorted in obvious frustration as he wiped it clear of some of the sweat at least. His morning was terrible, his girlfriend not only didn’t want to have sex with him but possibly no affection whatsoever. “You shouldn’t eat that when you’re upset.” Valerie said, sitting at the empty bench attached to his steel table. “It’ll make for a negative association.”

Danny grumbled and sat the greasy bacon cheeseburger with extra onions and jalapenos he got from the food truck outside on the small paper plate they had given him. “Here I thought it’d just get me full.”

“Hmm, the brain is a very strange machine. You associate the short rush of happiness the burger gives you and before you know it you’re forty with a beer gut around your knees.” She giggled, hoping he would join her. If only to see him happy.

“What are you doing here, Val? Don’t you have class?”

“My next class isn’t for another hour, besides, I wanted to talk to you about Lucy.”

“There’s nothing to talk about.” He said, picking the burger back up.

“Yes there is.”

“Fine. Nothing I want to talk about with my sister. No matter how smart she is.”

She pushed his burger back onto the plate, “Then just listen.” Danny shrugged, “Lucy is going through a tough time right now.”

“I know. I’m trying to help her but it’ll be a minute before I can do any more side jobs.”

“No, not just that.

“What do you mean?”

“Lucy…You remember how she used to be, right?”

“In what way?”

“You know what way I mean.”

“...yeah.”

“Well, Lucy is seeing for the first time what a good relationship is like. And it scares her.”

“So it is my fault?”

“...Kinda sorta? Only because you are a good boyfriend and she has never had one of those.”

“Shouldn’t she be happy then?”

“You’d think, but like I said the brain is a strange machine. Lucy is used to having a give and take type of relationship, where emotions don’t enter into it. It’s her comfort zone. You…you’re an emotionally intelligent man.”

“Geeze don’t say that too loud. I’ve got a reputation to uphold.”

“You’re an idiot. But you are smart enough to know what I mean.”

“I guess I get it, but what am I supposed to do then? Be mean? Be an asshole? I…I don’t think I can do that. She’s still my best friend and now…”

“I know. But being mean isn’t what I’m talking about, I’m talking about meeting her on her level. Like I do with our bets and our games. It’s somewhere she’s comfortable until she’s ready to own her truth.”

“I have to make bets with her just to get a kiss?" Danny groaned.

"I don't know. Has she ever done or said anything that you can think of that might give you a clue? Maybe she's already shown you the way she's comfortable being more open with you or other people."

“I don’t know.” He said softly, picking at his burger.

Valerie frowned and placed her hand on her brother’s arm, “You’ll figure it out. Like I said, you’re smart.”

“Should I even bother?” He asked as he looked up from his burger. “This is all pretend…isn’t it?”

“I can’t answer that for you. I do know she’s liked you for a while now.”

“She has?”

“Of course. She’s clever enough, she could’ve gone anywhere and gotten away or hid. She came to you because you’re a comfort to her. Somewhere, someone she feels safe with.”

“Yeah but…it was your idea she dress up like a girl.”

“No it wasn’t. I helped her make the changes, yes, but she asked me for help along the way. She even asked me to speak to you.”

“Why couldn’t she do it herself? If I’m someone she feels safe with-”

“Because she's not ready for that level of vulnerability. Even with you. Maybe especially with you.”

“What?”

“If she says something that scares you off, she’ll lose you. Her best friend. Her love. And her safe place. All in one.” Danny frowned. “Hey.” She said softly. “The good news is the more of her truth she accepts the less complicated it’ll be. I know this is a lot to carry right now, so I’ll understand if you don’t want to continue. I can talk to her and I can work with her.”

“Let me think about it.” He said in a near whisper.

“Okay.” She responded just as softly before standing and hugging her tall brother. “We’ll talk later.”

That night Danny didn’t balk at Lucy's attempt to kiss him, or when she sat in his lap as they watched television, but it was no less awkward for the couple. Danny found himself lost in thought for most of the night as Lucy and Valerie talked about something or other, mostly centering around her nails from the pieces he picked up. He thought back to his relationship with Harlow. Harlow got upset often when anyone would suggest the two were boyfriends, and now he was Harlow’s boyfriend. Of course he was Lucy now…or maybe she always had been? Was he upset because he didn’t think of Danny that way, or was she upset because she did and thought it could never be? This thought reframed so much of their relationship. Just a few short years ago before Danny had graduated high school they were hanging out in their living room watching an old movie. ‘What was it called?’ he thought, picturing the beautiful blonde in her purple wrap dress. ‘Ah. How to marry a millionaire.’ Harlow had made fun of him on more than one occasion when Danny mentioned how he thought Marilyn’s voice was sexy. Even going so far as to prank calling him one day and flirting with him in her voice. It only lasted a minute before Harlow broke down and started laughing.

Was he actually making fun of him, or…was he afraid of being rejected?

Another memory that stuck out was an incredibly hot spring day long ago when the two were in the backyard and played war with water balloons at each other while the sprinkler acted as a death laser. It was getting just before dinner and Danny had lost Harlow for several minutes. When his mother had called the two in for supper. Out of nowhere Harlow tackled Danny screaming like Tarzan. Being relatively the same height at that age he managed to slam Danny to the ground. As the water balloons he had taped to his chest and stomach exploded against the two. At the time he thought nothing of it as Harlow sat on him giggling, his shoulder length hair dripping wet as he smiled down at his friend. Harlow claimed his mother was too busy to take him to get a haircut, but at the time Danny couldn’t fathom how a mom could be too busy for something so simple. He was older and understood now, but then he couldn’t. Thinking back to that year he thought, with his high pitched voice, many people thought Harlow was a girl of ten instead of a boy of almost twelve. Including Danny in that moment. But a quick change before Harlow’s first and only year of baseball a week later cleared him of that confusion. ‘Did she know even then?’ He thought. Harlow always got upset whenever anyone called him gay, or implied he was Danny’s boyfriend…was that what was upsetting him the most? Now they were, kind of, dating and she seemed just as upset. Maybe Valerie was right, she’s just scared, but…that didn’t mean he had to stay with her. Didn’t he deserve someone who felt safe enough to engage in their relationship with openness and honesty?

“You got her?” Val asked gently as she stood in front of the couch stretching her back.

Danny looked down and, sure enough, Lucy had fallen asleep on his lap again. “Yeah.” He smiled softly, picking her up as gently as he could so as not to wake her.

Placing Lucy on their bed Danny started to turn so he could finally go to the bathroom and relieve himself after holding it for the last two hours only to be stopped by Lucy who grabbed his hand. “Does it hurt?” She moaned, her eyes barely more than slits.

“Does what hurt?” He asked softly, sitting down next to her.

“Your hand.”

“A little but I’ll be fine.”

“I’m sorry.” She moaned, burying her face in her pillow.

“Hey, I’m fine.”

“Nooo.” She pouted, half looking up to Danny, the other half of his face still hidden by the pillow. “You’re my best friend.” She giggled, “And my boyfriend. You’re my best boyfriend!” She giggled again before closing her eyes.

Danny smiled, “And you’re my best girlfriend.” He kissed her gently on the cheek. He hadn’t noticed before that whenever Lucy got up she was a little more unbalanced as she walked back to him. But he recognized a drunk girl when he saw one. Danny watched for a moment until he was sure Lucy was asleep. Tucking her hair out of her face he decided she may be more obviously scared, but so was he. If they broke up he’d lose his best friend too. It was one of the reasons Naomi didn’t want a relationship with him. At the time he didn’t believe her when she said she simply “liked him too much” to risk that with anything more. ‘Harlow always was a gambler.’ he thought as he left the room.