holiday-hobo
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Holiday Hobo

Holiday Hobo

by lingeringafterthought
19 min read
4.81 (15200 views)
adultfiction
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Thanks for reading my

Literotica Winter Holidays Story Contest 2024

entry! Have fun and please take good care of yourselves through the holiday season.

*

I couldn't tell you what jolted me awake from a sound sleep with a sense of impending doom that snowy December morning. There were no ominous tolls of the grandfather clock in the study, although those gongs often gave me the willies. Why did they decide to make those things sound like that, anyway? Nothing says "consequences are coming" like the ominous ringing of a grandfather clock.

The sense that karma was soon going to be crash landing on my life wasn't triggered by the fact that the bed that wrapped me in ridiculous thread count sheets was not actually my bed... or that the owner, Mr. Jacob "Jake" Michaels, had no reason to believe that I was using his house temporarily. It wasn't even that I knew that somewhere in the house there was a 120 lb Rottweiler named "Baby" according to his tag. Baby and I had an understanding: I let him snack on anything that looked interesting in the fridge or pantry, sleep on the bed, and snore like a freight train and in return for these courtesies, Baby let me borrow his master's house for a few weeks.

It's not that I'm a squatter. I'm not! I don't want to own any of these places that I inhabit for a short time. I just... really like them. They feel right! They're homes! They have food and warmth and comfort. They have incredible showers and come furnished with skin and hair products. They're like an oasis of recovery in an otherwise cruel world. I love these homes! Probably a lot more than any of the people who leave them abandoned for weeks at a time while they go do XYZ things in Dubai or Singapore or wherever. These gorgeous places need love instead of abandonment, and me? I have a lot of love to give.

So anyway, there I was waking up with a contented sigh on a pillow that could only have been invented with NASA technology, and I just felt... off. Feeling "off" is such a waste in a home like this, so I decided to just open my eyes and deal with the situation. That's when I saw him. Jake Michaels, I presumed. He looked tired, slumped low in an armchair across from where I slept on a luxurious cloud of whatever this mattress was made of. His clothes were the usual rich guy stuff, a bit rumpled, though. His shirt had two buttons undone and his chin nearly rested on the patch of skin that peeked through the opening. He looked to be in his late 30's, his body strong, but weary, at the moment.

Now, I'm not brilliant at social situations, but even *I* knew this one was awkward. Most people who come home to a modern-day Goldilocks, or Redlocks in my case, sleeping in their bed... well, they call the police, or scream, or generally take loud action, whereupon I would quickly exit and call out apologies for getting the wrong house, being drunk, or some other plausible excuse. Jake Michaels carried an armchair over to the side of the bed where I was sleeping and just sat there... well, honestly, it looked like he had melted there. It was pretty passive-aggressive, if you think about it. He obviously wanted me to know I'd been caught, but didn't want to invest the emotional energy to actually deal with the confrontation of throwing me out of his house. That's pretty toxic, if you ask me.

Well, since I have no tolerance for narcissists who can't be bothered to freak out when they're supposed to, I began the process of creeping out of the massive bed by butt-scooting backwards, away from my drowsy, passive-aggressive supervisor, until I would drop out of the other side of the bed, disappear from view and quietly crawl out of the house after gathering my things that I kept ready for quick escapes in a bag under the bed. That was the plan, anyway.

With the first backward butt scoot, though, Jake Nonconfrontational Michaels opens his eyes, rubs his hand over his face, blinks a few times, and says "Good morning."

"Good... morning?" I said, looking around uncomfortably.

"So..." he said, taking a short break to do a lion-like yawn, "Everly Landers, daughter of Renae Landers -- deceased -- and 'unknown father'... are you a tramp, or are you a hobo?" he asked.

Have you ever had a conversation where a guy just starts flexing by showing you they know way too much about you without explaining how they know it? Totally passive aggressive... and creepy. Not to mention that he wanted me to claim either the title of 'tramp' or 'hobo.' He seemed interested in the answer, though, and he wasn't just wrapping up his "WTF are you doing in my house" inquiry in veiled insults. Was I a tramp or was I a hobo?

"Is there a difference?" I asked, genuinely curious.

Jake leaned back in the armchair, crossed one long leg over the other, and then smiled like he found my question amusing. "Yes," he replied.

What a nice conversation, I thought, refraining from rolling my eyes. You know you're in trouble when you're trying to talk with someone who answers your yes-no questions with only "yes" or only "no." That bullshit is both passive... and aggressive... with each word pronounced separately with a smug, but handsome, smile. Ugh.

"What is the difference between a tramp and a hobo?" I asked, trying my best to appear interested rather than intensely irritated that I was having this conversation rather than being chased through the neighborhood by the police.

"The difference, Everly, is a willingness to work. A tramp is a person who travels around from place to place, avoiding work whenever possible. Whereas a hobo is a person who travels around from place to place, but is willing to work whenever possible," he said, tilting his head to the side and blinking slowly at me. "More particularly, in your case, the difference between a tramp and a hobo is a felony conviction."

"I haven't committed a felony!" I protested, sitting up in bed, "I just borrowed your house while you were gone!"

"Breaking and entering..." he said, flicking some lint off the leg of his pants, like the conversation was boring him.

"I didn't break anything and your dummy dog walker leaves the door unlocked and the security system off while he walks Baby. Practically left a "welcome" sign lit on the place. At best, I'm a trespasser and that's not a felony... I'm just a lingering party guest who doesn't leave a mess and only eats expired pantry items."

"Impressive. Your moral relativity is utterly wasted outside the legal profession. Trespassing, however, is a felony when performed with the intent to commit burglary... and that bauble around your neck is worth a small fortune."

That was when I noticed the weight of the necklace that hadn't been around my neck when I fell asleep last night. With trembling fingers, I reached up and touched it. I knew what it was without even looking down, remembering holding the impressive diamond necklace up against my decolletage when I found the jewelry stash in the walk-in closet suite near the bedroom. I usually don't go in for jewelry, but it's like there was some kind of magical charm surrounding it, drawing me in. That didn't explain why it was around my neck now, though.

"I... I didn't put this on, though! I just looked at it!" I squawked.

"And yet, there it is... I imagine the security footage showing you taking it out of the box and displaying it against your body will be enough for the prosecutor, though," he said, smiling at the rock resting on my upper chest.

"I... I didn't..." I stammered, clawing at the back of my neck, trying to feel for the clasp and remove it. I remembered that was the reason I hadn't actually tried the necklace on -- I couldn't figure out how to open or close it, and that's a recipe for trouble. Don't put on any jewelry you can't get out of. Then, it occurred to me, "You! You put this on me!" I accused.

"Unfortunately, I don't think there is security footage of that... I must have accidentally placed my luggage on the dresser and blocked the camera's view," Jake said with a tsch of regret. "As it is now, if you attempt to leave without my consent it will be quite simple for the authorities to track your location with the geo-tag concealed in the necklace and bring you to justice for several years. Pity."

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"What... what do you want from me?" I asked, still trying to understand why I wasn't being chased through the neighborhood by the police.

Jake didn't respond. He just away from me with eyes that were more than tired... they were weary. His eyes were just done. He didn't even have the energy to get angry about a weird woman sleeping in his bed or walking around his house wearing nothing but one of his old sweaters and her underwear while he was away. I thought he was going to fall asleep again when he finally spoke, "I've been trying to get home for 37 hours... and in the middle of it, I realized that it was Christmastime again. Until I looked over and saw that stupid, sappy movie playing across the aisle... I've been working so much... it hadn't even occurred to me. Another year come and gone with nothing to come home to but an empty house, plus-one work events, holiday cards... pictures of families with stories to tell... well-meaning pity invitations to friends' homes..." he trailed off, his eyes looking at the ceiling fan, but his gaze was miles away.

I knew that gaze. I'd seen it in the mirror more than a few times. He didn't really care that I was in his house because, for whatever reason, he was done caring about anything. He was looking at another shitty, empty Christmas as a single guy with everything he could ask for and nothing of worth. He needed what he couldn't ask for...

"Want me to get you through it?" I offered. Jake's eyes moved to mine, suddenly alert. I cleared my throat and continued, "I... I could hang out... be your holiday hobo and fend off the ghosts of Christmas expectations for you... and in return, you'll take this pretty ankle-monitor off my neck and we'd just call this whole housesitting thing a misunderstanding?"

He stared, thinking about it. As weird as the idea was, I had a feeling he would accept. When you're looking down the double barrels of a shotgun loaded with holiday self-reflection, loneliness, life judgement, and depression buckshot, a bit of ill-considered novelty to distract you from everything can be a real lifesaver.

He dragged a hand down his face and sighed, "Get out of my bed, hobo... we'll talk about it when I feel human again."

"You got it, boss," I said, jumping out of bed and grabbing my clothes.

*** *** ***

Hours and hours later, Jake walked out of the bedroom and into the kitchen wearing only a pair of boxers. I took a glass out of the cupboard, filled it with water from the fridge and handed it to him. He drank it, filled it again, drank that, and then filled it again while checking out my bare legs sticking out from under his oversized old sweater. I figured I'd wait for him to talk first, but it was hard for me because I'd been busy and had a lot to say.

"What's that smell?" he said, after an eternity.

"Flour, butter, egg, vanilla, baking powder, baking soda, and sugar. Cookies. Sugar cookies. Except without the sugar. I mean, there's sugar in the dough, but there wasn't any colored sugar to sprinkle on top, so they're naked," I said, glancing down to his boxers for some reason.

"I don't eat--"

"Yeah, I know you're keto. You're so ripped that sleeping with you is probably like cuddling up to a pile of rocks. I can smell your nail polish breath from here. Your pantry is full of dried meat products and low-carb snack foods, which makes me wonder if crushed pork rinds might taste good on these things. Of course you're keto... but, you told me to get you through Christmas, and there's no way of doing that if you're staying in ketosis," I said, taking an oven mitt out of a drawer (earning an offended snort at my familiarity with his kitchen) and took the frying pan serving as a cookie sheet out of the oven and put it up on the stove to cool.

"I'm not eating that," he said, frowning as I began using a spatula to move them out of the pan and onto some paper towels on the counter.

"Okay," I said, placing more balls of dough in the frying pan and popping it back into the oven. "They're better than Xanax, though. Eat some cookies and drink some wine. Christmas was never meant to be faced with a clear head and perfectly chiseled washboard abs. It's just not Christian."

"What?" he snorted, turning away from staring at the sugar cookies cooling on the paper towels.

"Okay, well see, God sent Jesus to be born because people couldn't live under the demands of God's law. It was too much. The law demanded perfection and peoples' imperfections separated them from God. Nobody's happy when there's too much pressure to be perfect. God sent Jesus so we wouldn't have to be perfect anymore. So, basically, it's not Christian to be perfect at Christmas," I explained with a shrug.

"I see. Does it say anything about home invasion in this heartwarming story?"

"Not that I'm aware of... just a stable invasion and an angel rave."

"Delightful. So, what does any of that have to do with cookies?" he asked, leaning against the counter.

"Um... I don't know," I admitted. "Thought they might soften you up. I really can't go to jail." At that, he looked me up and down like he had something to say but was holding back. Probably something about my life choices. I decided to change the subject. "Um, so I unpacked your suitcase and did the laundry... your clothes are ironed and back in the closet. Your home automation assistant thingy asked if you wanted the groceries ordered, so I said "yes," but I added a few things. Hope you don't mind. Just stuff for the holidays.

"Whatever, it's fine... thanks for the clothes. I hate doing all that when I'm jet-lagged."

"Yeah, I figured. The assistant thingy said you had a work party tomorrow night. You going to that?"

"*We* are going to that. Wear something Janell left behind... you're about the same size."

"Janell... you guys break up recently?" I asked.

"Six months ago. You'll meet her at the party... she's with my boss, now."

"Sounds complicated... and like your boss sucks."

"He does. She does, too. In fact, I found her sucking on him at the company picnic last summer. Now, he spends his time trying to find petty faults in my work so he can justify removing me without alienating company leadership and most of his client base."

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"Damn. Insecure boss and climbing ex-girlfriend... so, I guess you need me looking revenge-good at this thing? Enough to get peoples' tongues wagging over something other than your boss stealing your girlfriend?"

"That would be delightful, yes. Formal. I'll be in black tie."

"Okay... um, I'll see what I can find."

"Incidentally... where did you get the sugar?" he said, casually looking over the assembly of cookies on the paper towels again.

Oh crap. I was hoping not to get into that particular bit of information just yet. When I decided to bake the chewable mood-enhancers, I discovered that he didn't have a speck of sugar in his house... and I couldn't make cookies with that weird stuff he used to pretend that he could eat sweet things and still look like a Greek god. "Well, you had everything else for the cookies, so I just popped over and asked your neighbor for some."

"You talked to my neighbor?"

"Yeah."

"You talked to my neighbor."

"... yeah?"

"Which one?"

"The one with all the Christmas stuff in their yard? They seemed like they'd have sugar... they were really nice."

"Oh dear God. Not them. Everly, stop talking to people. It has consequences."

"Yeah... okay. Sorry," I mumbled. I realize that, at this particular time, most people would have mentioned that the sugar I borrowed from the neighbor came along with a promise to have Jake come Christmas caroling around the neighborhood with them on Friday night to help them round out the baritone parts. Then again, most people weren't trying to avoid irritating a jetlagged guy dangling a felony conviction over their heads. Things being as they were, I figured we could get into the whole caroling thing later.

*** *** ***

Okay, I don't know who Janell was, but damn... if these were the dresses she left behind, I can only imagine what she took with her when she went to go suck on Jake's boss for a living. I stood in my underwear, held a long midnight blue gown in front of me and looked in the full-length mirror on the back of the closet door, trying to see how it would look on me without doing the gymnastics of actually putting on the dress. Suddenly, the door opened and I squeaked, backing into the hanging dresses to hide myself.

Jake walked in, unconcerned with the fact that neither of us were properly dressed, took a garment bag with a tuxedo in it off the rack and walked out again. "Not that one," he called over his shoulder as he left. "She wore that when I proposed. She'll think I'm not over her."

"Well, which one should I wear? It's not like you have a lot of options for a redhead in here..." I grumbled, emerging from the hedge of formal gowns filling his closet with bitter memories. "Black is basic and I'll just disappear... which is great, unless you're trying to rule the room with a revenge look. Green is good, but then again I'd just be another redhead wearing green because it's the opposite color spectrum from my orange head. Red? Forget about it. Too complicated, potentially explosive. Yellow? Yes, let's make 'candy corn' our--" I ranted, getting cut off when he walked back into the closet and handed me a garment bag I hadn't seen before. "I swear to God, if this is brown..." I began.

"Just hurry up and put it on, hobo. I have someone coming to do your hair and makeup soon. We leave at 7:00," he called from the other room, just before the shower started.

I unzipped the unusually heavy bag with some trepidation. Too many colors looked completely wrong with my pale, pinkish skin and my long red hair... and he wanted me to be looked at. When the bag opened and the dress was revealed, I knew I was in big trouble. I wondered briefly what was being served for dinner at the women's prison, before I screwed up my courage and put the damn thing on and marched into the bathroom.

"Nude?" I yelled over the sound of the water spraying into the foggy glass enclosure. Jake poked his head out of the shower and looked me up and down, a satisfied smirk growing across his face into a full grin. "I can't wear this! I look naked!" I yelled.

"You look good naked," he answered, simply. "Like a work of art. There is also an extremely costly lace of champagne beadwork over it, so you don't look completely naked... just sparkly naked. Get me some more soap, would you?" he said, nudging his head toward the cupboard across the bathroom.

"How did you even get the right shade? It's nearly impossible to get the right shade of nude for me! I look like some kind of --" I yelled, cutting off when he walked out of the shower wearing only some really lucky water droplets and got himself some body wash out of the cupboard.

"You were saying?" he said, stepping back into the shower with his bottle.

"I forgot," I said, sitting down on the edge of the jacuzzi tub nearby.

"Hmm. I'm sure it will come to you later," he said, closing the door again, fogging the glass and obscuring his body from view.

I sat there nodding, sure he was right. The thought in my head that turned invisible was something about being naked. It would come back to me. Funny how things just fly out of your head randomly like that.

*** *** ***

"I'm nervous..." I said, taking his hand as we walked up to the venue. "For all appearances, I'm wearing only beads and if you keep looking at me like that, they're going to think you hired a hooker to be your date to this."

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