The Housekeeper, Chapter One

Author’s Note: Commissioned by EthanDalton96. Thank you for your pledge, and for all the ideas that are making this story possible!

Chapter One

Jess

I couldn’t believe my luck!

University wasn’t cheap, so I had decided at the beginning of my first year there to keep my babysitting business from high school going. My website was already set up and, it may sound braggy, but I was pretty great at my job. Reliable, punctual, great with kids, and almost always asked back. By the time I graduated high school, I honestly could have given up higher education and made a decent living with the rates I had established by the end. Between the referrals and the repeat jobs, the only thing holding me back from babysitting every night was the fact that I still wanted a social life. 

So, since I ended up at a local university, it made sense to keep running my business. I was a lot choosier when it came to the jobs, since I could only give up one or two nights a week while still keeping up with my studies and enjoying the freedom of living alone. Not totally alone, as I had a roommate, but that was still more liberating than sharing a roof with my parents. For the most part, I tried to stick with younger kids with earlier bedtimes, so I could knock out some homework and studying for a few hours at the end of the night. As for the rest, I referred them to friends of mine that were still in high school, as not many other girls my age were still babysitting. For a small, one time fee, of course. It’s not that I was greedy. But textbooks were expensive, and I had put a lot of work into my teenage babysitting career. I wasn’t just going to give more than half of it away for nothing. 

Then, at the end of my sophomore year, I hit the jackpot. Some wealthy family halfway across the state got my name somehow, and offered me the job of my dreams. For starters, it was a lot of money. More money than I currently had in my checking and savings account combined. If that wasn’t tempting enough, the summer job involved watching a teenager. Personally, I’ve never minded babysitting teens. While the attitude can sometimes be an issue, the huge ‘pro’ is that they’re self sufficient. My trick is to just treat them with respect, lay down a few basic rules, and otherwise let them do whatever they want. When I pull it off correctly, they get a whole night of doing their own thing without being bothered, and I get paid for doing nothing but maybe making a meal if the parents didn’t leave money for ordering something. 

Part of the reason I was being offered so much was due to the commitment involved. Six whole weeks staying at their house and watching their kid while they were on vacation. I had only done two overnight jobs before, and both of those were just a Saturday/Sunday thing. This was definitely outside the scope of my usual experience, but that didn’t mean I wasn’t equipped to handle it. It was summer, so I had the time, and it was really good money. On top of that, a quick online search of their address showed me that the family lived at this huge manor, complete with a guest house and a pool. I would probably be staying in the main house, but there was always the possibility of inviting a friend over and having a sleepover across the way after my teenage charge was fast asleep. Oh, and they had a pool. 

In a lot of ways, this could be both a job and a vacation. No parents or other adults around, and a fancy, expensive property for me to relax at whenever Hannah was content entertaining herself. That was the girl’s name–Hannah–though I didn’t get many details about the girl herself. For the most part, the messages were about the job. And it made sense that the girl’s parents were hiring a babysitter. Plenty of teenagers could be trusted to be home alone for a day or two, but six weeks was a long time. Hannah probably didn’t want to be shipped off to some relative’s house for half the summer, so this was the better alternative. 

When the day arrived, I must have spent hours getting ready. Hannah’s parents had an early morning flight, so they wouldn’t even be there to greet me. However, teenagers could be quite judgmental, and I wanted to make a good first impression. Also, I was stuck between being daunted by the fancy manor and wanting to look like my usual summer self. And that was just one outfit. Packing was a whole other thing, though I solved that problem by simply throwing everything I owned into my suitcases and duffel bags. It would be easier to choose future ensembles after seeing how Hannah dressed. Normally I wasn’t afraid to just throw on jeans and a tank top, but that was when I was a middle class girl babysitting for middle class families. This was different. 

Heels were a must. 

I was short for my age; only 4’11”. Breaking five feet would have been wonderful, but I hadn’t grown in years. Now that I was twenty, I was more or less resigned to my embarrassingly short height. Thankfully, I had plenty of other things going for me. My chest was a point of pride. 32C exactly, which made bra shopping simple compared to other girls I knew. I also worked out a minimum of three times a week, leaving me with a well-defined stomach and a hint of tone everywhere else. 

Looking myself over in the mirror after my shower, content with how my naturally tanned skin looked better than usual after a fresh shave, I got to work blow drying my brunette locks so any lingering dampness on my body could air dry at the same time. I’m not vain, but I’m also not blind. I know I’m decently attractive, minus the pathetic height, and today was especially important to highlight and accentuate all my best qualities. After building a good rapport with Hannah, I could probably get away with messy hair and PJs. But on day one, I had to look my best.

Ultimately, I decided on a dark green sundress. It was one of my favorites and, like many dresses of that variety, did a good job of looking nice yet casual. It was comfortable, too. For footwear, I opted for a pair of brown heels that gave me an extra three inches of height. Returning to the bathroom, I made short work of putting in my contact lenses and adding a light curl to my hair. Picking out an outfit was one thing, but I didn’t trust myself with a curling iron without my contacts. Aside from my height, my poor vision was the other thing I wasn’t particularly fond of. That, and my tiny feet. 

My parents were already off at work, so I hauled all my suitcases and duffel bags downstairs and to the car by myself. After triple checking my room for anything I tended to forget when it came to trips–chargers, toiletries, and socks–I jotted a quick note with Hannah’s address and her home phone number in case there was an issue with my cell, and then hopped in the car to make the four hour drive. 

I’d be getting there just after lunch. Her parents had assured me she would be fine for half a day by herself, but I still felt a little bit nervous along the way. Normally, I would arrive and greet the parents before they left, especially for a new job. Halfway through the drive, I considered calling Hannah during my stretch break at a rest stop. I had already added her cell phone number into my Contacts, as well as the landline. After thinking for a minute or two, I decided against it. The average teenager didn’t enjoy talking on the phone, and it would be better if my first interaction with her was face to face. 

Finally, after a healthy combination of podcasts and music, I arrived at Walker Manor. Turns out, the online images didn’t do it justice in the slightest. As I drove through the main gate and looked around with wide eyes, it was difficult to tell where their property ended and nature began. The time it took to get up the road/driveway was enough to get a good look at the perfectly kept grounds, a gorgeous lake off to the left, and the enormous stone house that I would be staying in for the next six weeks. Suddenly, my sundress felt entirely inadequate. I should have shown up in a fucking ballgown. 

Where was I supposed to park? There was plenty of space right in front of the house, but the smooth driveway also looped around the side towards the smaller guest house and perhaps a nineteen car garage. I wouldn’t be surprised. For the moment, I stopped the car near the main door. Hannah would know better than I would, plus this would be easiest in terms of hauling all my things inside. Taking a deep breath, feeling entirely out of my element, I stepped out of the car and approached the front door.

‘Housekeeper.’ That’s what I was supposed to be. At least, that’s what Hannah’s parents had strongly suggested. Since I’d be doing a bit of the cooking and cleaning, like I ended up doing at most of my jobs, they thought it would be a better term than ‘babysitter.’ While I understood where they were coming from, as their idea would be theoretically easier to swallow for a rich teenager who probably thought she didn’t need supervision, I had been in this line of work for a while. Kids aren’t stupid, and that goes doubly so for teens. If I had to guess, Hannah would see right through the white lie. 

But I would try. Jess, the housekeeper. 

As long as Hannah and I could coexist, I’d go with whatever title worked. It was going to be a win/win. I’d get a six week vacation at a place that would cost me thousands if it were a bed and breakfast, and their daughter would get the freedom she wanted. As long as she didn’t destroy the house, I could be flexible about a lot of other things. 

Taking another breath, I took the brass knocker and officially announced my arrival.

Hannah

A babysitter. A fucking babysitter. 

I was going to kill my parents. What, they didn’t trust me because I hosted a party one time when they were out of town? It’s not like I left a huge mess for them to clean up. Hell, I hired an outside maid with my own money to put the whole house together in a matter of hours the next morning. The only reason they even found out is because one of my (former) friends ratted me out. She was too hungover, and bombed a university interview. Her parents managed to interrogate her enough that she cracked and tried to put the blame on me to save her own skin. 

As if. All she succeeded in doing was uninviting herself to every party since then. Were the pity points worth it, Brittany? None of us trusted her with anything any more. Goes to show what happened to girls who crossed me and my friends.

More importantly, I was eighteen years old. A legal ADULT. A high school graduate who absolutely did not need supervision. And yet, my parents decided that it would be a good idea to hire someone to watch me while they went off on some charity cruise. Like they actually cared about whatever their donation was going to. It was just an opportunity to lounge on a boat and see a few exotic countries along the way. Just like their real motivations for their trip was obvious, it was also painfully clear what ‘housekeeper’ really meant. We already had two maids. We had a groundskeeper. So why hire someone new at the exact time they were leaving for vacation? What a crazy mystery. 

My parents were long gone by the time I woke up. It was summer, which meant I didn’t plan on ever waking up before 9 AM. This new hire was supposed to arrive some time after noon, which meant that I had all of three hours to myself. I considered throwing an impromptu day party just to make her deal with dozens of inebriated high school graduates and perhaps some university students as well if I gave my friends the green light to invite their older friends and relatives. 

It was a fun idea, but it wasn’t a smart play. Why risk something that bold before even meeting the woman that was supposed to be supervising me all summer? I’m a people person, after all. I’d rather get a read on her and then plan accordingly. While I hated sucking up to authority figures, it wasn’t beneath me. I’ve done it plenty of times with teachers, especially the male variety, and playing nice with Jess could yield some equally positive results. She would lower her guard, and I could start pushing the envelope. Anything she lets me do once is something I could then do forever. Backpedaling is difficult once you’ve already said ‘yes’ to something. 

Also, what kind of name is ‘Jess?’ Short for Jessica, or maybe Jessamine? Most adults tended to shed such nicknames as they got older. Then again, this woman accepted a babysitter job, which meant she wasn’t well off financially. Maybe lower class types are more keen to stick with nicknames. Or maybe Jess was just an anomaly. Whatever. There could be a million other reasons, but dwelling on something like that was a total waste of time.

Changing into one of my many bikinis, I grabbed a bottled smoothie and some lotion before heading out to the pool. Jess was going to be here in a few hours, which meant this was my last chance to tan while topless. Practically, I just hated having pale orbs on my chest that didn’t match the rest of my skin tone. But also, it was exhilarating to be half naked outside, even if no one was scheduled to work this morning. Low risk, but still alluring to be reminded of my nudity every time a light breeze brushed my bare breasts. 

I stayed by the pool all morning. Texting, scrolling, and occasionally drifting off. I eventually got up to grab myself a pitcher of water, but that’s about it. Once noon hit, I was a little more alert, but opted to keep my top off for as long as possible. I think it was safe to assume that Jess would frown upon such exposure, which meant this would be my last opportunity to tan topless for six weeks. 

Honestly, having a babysitter was going to be worse than my parents being around. They worked so much, I almost always had the place to myself during the day. Now I was going to have to deal with near-24/7 supervision. Fuck me. 

Finally, I heard her. We were the only house in at least a half mile radius, which means the sound of a car was either the mailman or the new ‘housekeeper.’ Odds were on the latter, simply due to the timing. Groaning to myself, I grabbed my bikini top and tied it into place. Goodbye, peace and quiet. Goodbye, freedom. Despite the negativity coursing through me as I walked back inside, I forced a warm smile onto my face. The best way to sell a good attitude was to ease into it. While I was quite adept when it came to all things social, trying to flip the switch from ‘bitch face’ to ‘genuine smile’ was difficult to pull off without showing at least a trace of disdain. 

Just to be sure I had it right, I glanced at my reflection in the kitchen microwave. Perfect. My expression was hospitable, but my bikini-clad body would serve to throw her off guard as I opened the door. A lovely concoction to test how Jess handled herself when facing the unexpected. I waited in the kitchen, as I had no idea where the woman was going to enter. Front door? Side door? Or perhaps she’d just sit in the car and call the house. I had tried to break into my father’s home computer earlier to see if there was an email exchange between him and the babysitter, but couldn’t find the password anywhere in his office. 

Two loud knocks on the front door answered my question and put an end to my impatient waiting. Brushing my hair back and pushing another wave of warmth onto my smile and into my eyes, I sauntered down the hallway towards the front door. Taking my time, but also not making her wait forever. Similar to my appearance, I wanted to strike a decent balance when it came to my response time. 

With no hesitation, as I had always been the kind of girl who just rips off the band-aid, I unlocked the door and opened it wide for her. “Hey,” I said, “You must be Jess.”

Jess

The first thing that caught my attention was the bikini. Matching top and bottoms in a sharp emerald. Coincidentally similar to the color of my sundress, but I was more focused on all the bare skin that greeted me when I had expected Hannah to be clothed. But that isn’t where the surprises stopped. She was tall, easily towering over me despite my heels, and I instantly noticed what else was wrong when I looked up and took in her blonde hair and sharp facial features. 

Wait, what?

How old was this girl?!

When her parents had said ‘teenage daughter,’ I had first assumed that they meant thirteen or so, as that’s about the oldest I’ve ever had to supervise. I find that around that age, parents begin trusting their kids alone for a few hours when they go out for the evening. Since this was six full weeks, I had stretched my assumption to maybe fourteen or fifteen, where the girl could be self-sufficient while still needing someone around to make sure she wasn’t getting into trouble. 

But the girl in front of me had to be older than that. Sixteen, minimum. Or seventeen? Not legally an adult, so therefore needs a ‘guardian’ around in her parents’ absence? The moment she opened the door, I regretted jumping to conclusions and not asking for more details before accepting the job. I was only twenty years old! True, I had a solid eight years of experience babysitting, but still. How could I possibly earn the respect of a girl just a few years younger than me? 

I couldn’t just stare and overanalyze, however. “Hey,” I replied, hoping that she didn’t catch the faint hesitation. The blonde looked friendly enough, rather than a scowling teenager who didn’t appreciate someone disturbing her privacy. “Hannah, right?” I asked. It was a stupid question. Who else would be here in a swimsuit? 

“Mm hmm,” she nodded, “And you’re Jess. Or is it ‘Jessica?’ Aren’t you going to come in?”

“‘Jessica,’ technically,” I said, “But you can call me ‘Jess.’ And in a minute. I should grab my things. Do you-” Catching myself halfway through a request for help, I scrambled to think of something else to say instead. While I’d ask just about any friend for assistance with my luggage, I didn’t want my first encounter with Hannah to include me asking her for manual labor. What if she was the kind of girl that didn’t lift a finger around the house? What if this got us off on the wrong foot? Still determined to make this more of a vacation than a job, both for myself and for her, I pivoted. “Do you know which room I’m staying in? I can get myself settled if you want to go back to the pool. Sorry if I interrupted.”

“It’s fine! You actually got here at just the right time. I really need someone to get my back. You brought a suit, right? You should get changed up and meet me out there. I’d much rather get to know my new housekeeper by the pool, instead of in this stuffy house. Sound good?”

It was a lot to take in. While it would be irresponsible to let the girl burn, I didn’t know how I felt about physical contact like that before establishing my authority. Then she was suggesting that I join her by the pool, and in swimwear instead of my dress? On top of all that, the phrase ‘my new housekeeper’ didn’t sit very well with me. If I wasn’t careful, she’d assume that I was around to be more subservient. That was the opposite of what this dynamic was supposed to be, and suddenly I found myself wishing she did see through her parents' retitling of my babysitter role. 

So much to process, so little time to respond. And she didn’t even answer the question about where my room was! Okay, two could play that game. Remembering that she was a teenager, there was a good chance that she was at least playing a little bit dumb on purpose. “So where’s my room?” I casually asked. Not actually confirming anything, but also knowing that I’d need my own space to change if it came to that. 

To her credit, Hannah didn’t miss a beat. Maybe she wasn’t being difficult on purpose after all. “Upstairs, on your left. The room with the gray sheets.”

“Thanks, Hannah,” I said. Ugh, she was SO tall. The sooner we were both seated, the better. It would be much better laying down a few ground rules when I didn’t have to look up to meet her eyes. “I’ll be out in a few minutes, okay?” In my sundress. While it would be nice to relax by the pool and get some sun, it was way too soon to wear a bikini around her. Now that I was dealing with an older teenager, I’d have to adjust my entire game plan. 

“Oh, I can’t wait to see what you brought for swimwear! Trust me, you’re going to fucking love the pool here. You’re not the boring type who never jumps in, right?”

Boring? Me? Not a chance! I decided to let the swear word go, as that would almost prove her point right then and there. Not that she was making a point. The question had more of a playfully curious tone than anything else. “Of course not. I love to swim,” I replied. It was the truth. 

“Good!” she exclaimed, “Bikini. Pool. Ten minutes. I’ll be waiting, Jessie!” 

Hannah

The moment I opened the door, I had to forcefully shove down a laugh that was threatening to burst through my lips. 

No way. No fucking way!! 

This was Jess?! A short brunette girl who looked almost as young as I was? This had to be a joke. For some reason, I had expected a no-nonsense woman in her late twenties or early thirties. An age that could still work for a ‘Jess;’ an age that was old enough yet young enough to put up with the shit of a rebellious teenager. Or a manipulative one, in my case. Never in my wildest dreams did I imagine that it would be someone so much smaller than me, and so close in age. 

Did my parents know when hiring her? Or did they massively screw up? Only one way to find out. 

I started off friendly, testing the waters. Throwing a bunch of friendly ideas out while acting like she was just another girl like me. I half expected her to flip some domineering switch and lay down the law, but she didn’t. Instead, little Jess just tried to brush past my questions. Nice try, girl. At that point, I was determined to get her into a bikini and down to the pool. I would be her ‘friend,’ and she would have a difficult time fulfilling her babysitting duties when so underdressed. 

Hopefully my parting words would do the trick. Pushing too hard on the subject would put her guard up, so I simply swiveled on my heel and strutted away. Unfortunately, that meant I couldn’t study her reaction to ‘Jessie.’ Oh, well. There would be plenty of opportunities to try out the alternative nickname and see if it made her cringe or object. For the moment, I would once again have to be patient. Either Jess would change and prove that she was a fun girl who wanted to get along with the teenager she was hired to babysit, or she would come outside fully dressed and I would have to shift tactics. 

While I waited, I simply sat by the edge of the pool and dipped my feet in to cool off. Leaning back and killing time on my phone; making it seem like I was content to do so for hours even though I was restless with the countless ideas to put Jess in a situation where she felt more pressured to be a roommate than a babysitter. 

To my partial disbelief, the girl actually came outside in nothing but a bikini!! Not even a towel draped over her shoulders to hide part of her bare skin, which was almost as surprising as the fact that she changed in the first place. I couldn’t help but wonder what the deciding factor was. The excitement about what she brought? The insinuation that she might be boring? The general need to make our first day together as smooth as possible? Probably that, though it was fun to imagine that my directive before walking away was what sealed the deal. 

As Jess got closer, however, my internal smugness quickly evaporated when I caught a glimpse of her breasts. 

FUCK.

I hadn’t noticed it before, as the cut of her dress was more modest at the neckline, but her cleavage was a lot more obvious in the bikini top. How on earth did such a small girl end up with boobs like that?! While I was thoroughly hot, tall, and slender, and could have pretty much anyone I wanted, it would have been nice to have a little more in the upstairs department. And this little college girl had bigger breasts than me? Fuck that.

The plan to shift Jess into more of a friend/roommate was no longer acceptable. Right then and there, I dismissed all the floating ideas that had occupied the majority of my headspace just moments ago. It was one thing for this fucking brunette to show up at my house and think that she could boss me around. I was way too old to need a babysitter, especially one her age and her size. It was something else entirely, however, for her chest to be better than mine. That was bullshit. 

New plan.

I was going to humiliate Jess, and make her regret ever taking this job. She was going to feel small in more ways than one, in front of me and in front of my friends. And, if she was claiming to be my ‘housekeeper,’ then I was going to make sure that she conformed more to that role than anything else for the next six weeks. 

By the end of the day, I was going to make little Jessie bend to my will. 

Read Chapter Two

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