The Housekeeper, Chapter Twenty

[*Lady Lucia*]

This one is an ongoing commission; Ethan Dalton gets credit for the overall concept and a good portion of the details. I get credit for bringing it to life and putting a few of my own twists and ideas in along the way. :)

--Lady Lucia

-----------------------------------

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. More importantly, it wasn’t fair that her chest was better than mine. It 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 Jess bend to my will.

[*Lady Lucia*]

PART TWO

Jess

I wasn’t in love with the idea of wearing just a bikini.

My initial thought had been to wear a sundress over my swimwear, but I ended up changing my mind once I had a moment to myself. Hannah was a lot older than I expected, which meant my game plan needed to change. What if she thought I was a total prude by not doing what she suggested and matching her? She had also suggested I would be ‘boring’ if I didn’t get in the pool. A teenager’s opinion of me really shouldn’t matter, especially not from one I’m supposed to have authority over, but I was still determined to make a good impression.

If I could connect with her, get her to respect me more as a peer than an uptight adult, then maybe the rest of the summer would go more smoothly. After all, I tended to trust advice from friends. If she viewed me as such, then I could gently nudge her away from anything her parents wouldn’t approve of. It would be a delicate line to walk, but I could already tell that my height was going to be a big issue now that I was a lot closer in age to my charge than I expected. I was technically older, but Hannah towered over me!

“Get my back, Jessie?” Hannah asked. She gestured to the sunscreen sitting on the small table next to her chaise lounge chair. Rather than turning away and scooting over so I could sit behind her and apply the lotion, she proceeded to lie down on her stomach and reach back with one hand to untie the strings on her top.

I flinched at the use of ‘Jessie.’ It was the second time she had said it, and the second time I was reluctant to correct her. The first had been back at the front door, where she had bounded off before I could say anything else. I was left to haul all my things inside and park my car in what I hoped was an acceptable spot. This time around, I was immediately distracted by the blonde’s totally bare back as she pulled her hair over her shoulder so all of her fair skin was on display. It was less about what I could currently see, and more about the fact that one wrong move might give me an inappropriate glimpse of her bare chest.

Still in that weird headspace where I didn’t want to start things off on the wrong foot, I bit my tongue about everything. Instead, I grabbed the nearest chair and pulled it up so I could sit right next to the girl. “So, I guess we’re stuck together all summer, huh?” I said, trying to make light of this arrangement in an effort to connect with her. Ultimately, my goal was to spin things as ‘I’ll stay out of your way as long as you behave,’ but I needed to work my way there.

“Guess so,” Hannah replied. Now that she was settled, she lay perfectly still. Waiting for me to get to it, probably.

If only she gave me something to work with. A chuckle, a more full reply. That was my system for new babysitting jobs–get a read on their attitude, their humor, whatever I could use to figure out whether I needed to be easy-going or stern. “This is going to be a little cold,” I said. Cringing immediately at the patronizing warning, I squeezed a decent amount of lotion onto my hand and hoped she wouldn’t take it the wrong way.

Once again, nothing. When she didn’t reply at all, I tentatively placed my hand on her back so the majority of the sunscreen was centralized. I should have expected it, but her skin was so warm. The sun would do that, of course, but it gave me enough pause that she mistook my hesitation for something else entirely. “You’re not a lesbian, are you, Jessie?”

What?! “NO.” My response came out a lot more harsh than I expected. It’s not that there’s anything wrong with liking girls–I have several friends that are gay or bi–but Hannah’s question was just so blunt and out of the blue. “No. I’m straight.” I lowered my voice to a more normal level. While it might have been worth explaining that it was more that I felt awkward about this kind of contact with a girl I was supposed to be babysitting, I made a snap decision that ‘less is more.’ Instead, I chose something else to focus on. “And it’s ‘Jess.’”

“Jeez, no need to freak out about it. I just wanted to check. When I’m home alone, I like to be comfortable. Good to know you won’t be ogling me or anything.”

Comfortable? Like . . . ? I barely registered the subtle idea that she considered herself ‘home alone’ when I was literally going to be there. Instead, I found myself dwelling on what the girl meant. Just because I wasn’t into girls didn’t mean I wanted Hannah walking around in, well, whatever she wanted. “Comfortable, how?” I asked. Little by little, I found myself bailing on the ‘friend’ plan and slipping into the babysitter role I was more comfortable with. It was only after I asked for clarification that I remembered what I was supposed to be doing. Spreading out the sunscreen with my hand, I worked on making it even before rubbing it in.

Hannah let out a sigh before explaining. “I don’t know; it depends. Long tee and nothing else? Sports bra for a workout? A towel if I haven’t picked out an outfit yet? I mean, it doesn’t really matter. We’re both girls, so it’s not that big of a deal. Right?”

“Umm . . .” Technically, no. I had seen plenty of friends like that. Well, maybe not the t-shirt thing. Still trying to figure out this whole dynamic, I tried to split the difference. “I guess not,” I said, “But maybe get dressed before coming downstairs?”

She simply replied with, “Well see.”

Noncommittal. Great. I went quiet, focusing on Hannah’s back. Since I wasn’t there when she applied the rest, I made sure to hit her shoulders and sides, just in case. As for her lower back, I only went so far down after the ‘lesbian’ question. She was certainly capable of getting that last area herself, and it was important to keep up boundaries. If I had it my way, this wouldn’t be happening at all, but it’s not like I could deny the girl protection from the sun.

By the time I was finished, I could already feel my own skin heating up. Unlike Hannah, I hadn’t put on any sunscreen yet. Sitting up and informing the blonde that she was all set, I quickly rubbed the excess lotion on my shoulders. Before I could get much farther, she shifted her head to face me. “So, Jessie. Fuck any guys lately?”

What?!

Similar to her question about my sexuality, I was completely taken aback. Feeling a blush coming on, I blurted out the first thing that came to mind. “That’s none of your business.” The truth was, I was a virgin. It was a bit embarrassing for my age, especially since it’s not like I was a prude or saving myself. I had gotten to second and third base a handful of times, but those short-lived relationships never felt serious enough to go all the way.

Plus, even if I had slept with someone or multiple someones, what kind of question was that? Hannah and I just met. It would be one thing if she had asked if I was seeing someone, but that wasn’t at all what she said.

“Whatever,” she replied, “It’s just sex. I don’t know why people have to be so weird about it. Want to hear about who I fucked last weekend?”

“No!” I exclaimed. Once again, a little louder than I had intended. “You-” I began, before changing course. There was one thing I was dying to know, especially since Hannah was somewhat topless as she lay on her untied bikini top. “How old are you, Hannah?”

To my relief, she said, “I’m eighteen. You?”

The good news was, that made it more acceptable to see her in any number of ways that would otherwise be less appropriate. I had seen my fair share of undressed women in the locker room, after all, though I preferred to change in a stall. The bad news was, I had been hired to babysit an eighteen year old?? How on earth did that not come up when her parents and I discussed the job? It might have been my fault for not asking, or their fault for not looking closely enough at my website. No matter where the blame fell, I was apparently supposed to be in charge of a girl who was practically the same age as me!

I wanted to lie, but decided against it. Since I was going to be there for the next six weeks, there was a good chance I’d accidentally contradict myself at some point. “I’m twenty,” I confessed. Silver lining, Hannah had been told I was a ‘housekeeper.’ If she knew the truth, I could only imagine how insulted she might feel. And how difficult it would be to make her listen to me. Well, that was going to be an issue either way.

“Oh, cool. Hey, would you mind putting some snacks together? I have some friends coming over in a few minutes.”

Wait, what? “Hannah!” I exclaimed. She had said it so casually, but that’s not at all how I felt about the information sprung on me. “I didn’t-” My voice caught my throat. UGH. Since I wasn’t officially her babysitter, why would she need me to approve an invitation like this? I was quickly finding myself in a difficult position thanks to her parents’ insistence on this charade. “How many friends?” I asked. Thankfully, years of experience had taught me to be quick on my feet, and I pivoted. “Look, you need to ask me about this kind of stuff ahead of time. Otherwise, I can’t do my job as well.”

Hannah sighed. Taking care to grab her bikini top before doing so, she sat herself up. “Jessie. You’re my housekeeper. Isn’t that right?”

‘No. I’m your babysitter.’ If only. “Yes, that’s right,” I nodded. For now. First chance I got, I was going to give her parents a call and try to work this out. Either I needed to be able to tell Hannah why I was really here, or they needed to tell her that she had to listen to me. “And it’s Jess.”

“Then please do your job,” she said, “Snacks and drinks. You should also bring out some towels for us, and maybe some more sunscreen? There might not be enough in this tube for everyone.”

Oh, God. She was talking to me like a servant. Swallowing my pride, I nodded again. “Of course, Hannah. I’ll be right back.”

Not wasting another second with the presumptuous blonde, I went back inside. I had no intention of actually following the girl’s orders. My phone was just up in my room, and I also no longer felt comfortable wearing a bikini. It was one thing when I was trying to get Hannah to warm up to me, but she clearly didn’t see me as much of a friend. That, and apparently her friends were going to be there soon. I’d have better luck compelling respect if I dressed like the young adult that I was, rather than trying to hang out at the pool like ‘one of the girls.’

Closing the bedroom door behind me, I grabbed my phone from the top of the dresser and called the number on the mobile note I had made about the summer job’s details. Straight to voicemail. “Fuck,” I huffed. They could be on a plane, or simply enjoying their vacation if they were already there. I hated leaving voicemails, so I just sent off a text politely asking them to call.

I made short work of stripping off my bikini and tossing on a skirt/blouse combo that was one of my favorites. Just for good measure, I added a pair of heels. Normally I wouldn’t wear shoes inside, but I was feeling extra self conscious about my shortness compared to Hannah.

The entitled eighteen year old had said ‘soon,’ but I didn’t realize just how soon she meant. By the time I made it downstairs, I practically ran into an unfamiliar redhead as I turned the corner. She was wearing short shorts and a bikini top, and I honestly wouldn’t have been surprised if that’s how she drove. Before I could get out a word, she said, “Oh! You must be the new housekeeper. Is that your car out front? You should probably move it before it messes up everyone’s parking.”

Shit. I had hauled all my stuff up to the guest bedroom, but hadn’t found a chance to park my little sedan properly. It’s not even that I had forgotten about it; I just wanted to ask Hannah if I could have one of the garage spots. With no idea how many people were coming over, and with at least one already here, there wasn’t any more time for that. I ran up to grab my keys, then hopped in my car as soon as possible. Two other empty vehicles were already out there, and I maneuvered mine to line up with the others on the opposite side of the driveway.

Hurrying back inside, not wanting to leave the girls unattended for too long, I made a beeline for the pool. My initial plan of calling Hannah’s parents had failed, and preparing refreshments for everyone would solidify a subservient image of me in her eyes. Instead, I strutted outside in the hopes that I could pull her away from her friends for a quick one-on-one. I wasn’t totally sure what I wanted to say yet, but I’d figure something out. I was a professional babysitter, after all.

Right away, I was faced with the exact kind of situation I had been hired to prevent. Hannah, the redhead, and one other girl were all sitting together and drinking. Like, drinking. All three of them were holding hard seltzers, which was absolutely unacceptable. Day one on the job, and I was already failing miserably. The ‘housekeeper’ role was working against me, and my charge was illegally drinking under my watch.

“HANNAH.” Raising my voice, I began storming over. “Absolutely not. Your parents were very clear about the house rules when they hired me.”

“Relax, Jessie,” Hannah said. Her bikini was tied up again, thank God, which made it easy for her to stand up and meet me halfway. Despite my heels, she still had a good bit of height on me. “They don’t have to know, do they? I won’t tell them. You won’t tell them. So, what’s the problem?”

“It’s Jess. Get it right,” I insisted. Narrowing my eyes and not letting the fact that I had to look up to match her gaze deter me, I continued. “And no, I’m not going to cover for you. But if you hand it over, this can just be a warning. Okay? Otherwise, I’m going to have to call your parents.”

“Ooh, call my parents? So scary!” she giggled for a second, before going totally deadpan. “Fuck off. This is my house, and you can’t tell me what to do.”

“Yes. I can.” Screw this. I tried the ‘housekeeper’ cover story. It clearly wasn’t working. Maybe coming clean and embarrassing her in front of her friends would do the trick. As a former teenager, I could only imagine how it might sound to hear that you still need a babysitter. Eight or eighteen, some attitudes need a firm adjustment. “Hannah, I-”

But that’s as far as I made it. Out of nowhere, she dropped her can and shoved me with both hands. Hard. Unable to react quickly enough, I stumbled backwards only to find no ground waiting for me. Gasping at the way too late realization, I fruitlessly flailed my arms to no avail before plunging into the pool behind me.

My body submerged completely and I scrambled to upright myself and resurface. The section of the pool was too deep to find any footing, so I had to awkwardly tread in my clothes once my head was above water. The other two girls were sitting there with dropped jaws, before finally giggling as they came back to reality. Meanwhile, Hannah was just smirking down at me as she picked up her partially spilled drink for a victory sip.

I was furious. FURIOUS. But I couldn’t yell at her from the pool. Plus the chlorine was going to ruin my clothes and my contacts. Ugh, and my hair. It clung to part of my face in what I had to assume was an unattractive way, and I quickly pushed it to the side as I paddled to the nearest ladder. My heels caught on one of the metal steps, and I was pissed off enough that I cared a lot less about my height than before. Quickly undoing the straps and pulling them off, I climbed out of the pool barefoot with shoes in hand.

“Hey!” I yelled. My clothes clung to my body, and I was dripping all over. I didn’t need a mirror to know that I must look ridiculous, but I tried my very hardest to be intimidating anyway. “Laugh while you can. I’m going to take a shower, and then you’re going to be in deep shit.” It felt lame threatening an eighteen year old like that, but what other ammo did I have? Trying not to lose steam, I added on, “Your friends better be gone by the time I’m back, or else.”

“Whatever you say, Jessie,” Hannah said, “Now, go get naked.”

Not dignifying that with a response, even though it’s technically what I was about to do in order to rinse off, I marched back to the house. Normally, I would care a lot more about dripping inside, but I was over it at this point. What was I thinking? Of course I wouldn’t be able to control an eighteen year old rich girl. At this point, I was strongly considering quitting. I had never bailed on a job before, and I had dealt with some pretty awful kids over the years. But a whole summer of this? It was good money, but Hannah wasn’t some tween! For the life of me, I couldn’t think of a way to course correct without involving her parents. It would make me look so weak, relying on someone else in order to achieve authority. Groaning to myself after the glass door was fully closed behind me, I made my way upstairs, being careful not to let my bare feet slip out from underneath me on the way up the stairs.

The warm water helped. Not with the Hannah situation; it was just nice to have a moment to myself. To breathe, to calm down. Thank goodness I had taken a minute earlier to set the hallway bathroom up for myself. While I didn’t mind getting the rest of the house a little wet, I would hate to do that to my own room and give the smirking blonde the satisfaction.

I couldn’t believe Hannah’s audacity! What if my phone had been in my pocket? Plus, any kind of water was terrible for contact lenses. Thankfully, I had some spares lying around, so I could go grab a fresh pair while the current ones sat in solution. My wet clothes monopolized the towel racks for a moment, though I’d be running them through the wash the moment I was done showering. Initially, I had planned to be quick about it, but eventually settled into the idea that the longer I stayed behind the fogged glass doors, the longer I could pretend the outside world didn’t exist.

Eventually, however, I had to face the music. The voices through the bathroom window were a pretty good indicator that Hannah hadn’t listened to me in terms of sending her friends home. I could only hope that my long shower had given her parents enough time to check their messages so I could reach them momentarily. Turning off the water and finding myself twice as blind as usual thanks to the blurry vision and the heavy steam around me, I pushed open the door.

No.

No, no, no.

How could I have been so stupid?! Even with my poor eyesight, I could see what was wrong: The entire bathroom was empty. No clothes on the racks, no stack of towels on the sink where I left them; nothing. Even the towel that had previously been laid on the floor to prevent dripping had been taken. This had to be Hannah, or one of her friends. And I couldn’t help but blame myself a little bit–leaving the door unlocked? Horrible move.

I hated being seen naked. It’s why I changed privately no matter the setting. I mean, I’m confident enough about my body, but it’s MY body. And I could already imagine a gaggle of girls waiting on the other side of the bathroom door, cameras aimed to capture every second of my exposure. Hell, I was lucky they hadn’t quietly been waiting in here. With that in mind, I was extra careful as I peeked my head farther out of the shower.

Wait, there was something in here! On the back of the door. A towel, or a robe, or something. I couldn’t see very well, but I immediately let out a sigh of relief when I realized Hannah missed something. Taking a second to brush as much water off my bare form as possible, I wrapped my arms around my private areas and padded across the bathroom, bracing myself for someone to barge in at any second. The tile on the outside of the shower was a lot cooler than on the inside, and I grimaced as the bottoms of my feet dealt with the cold, hard surface. Without the warm steam, my nipples almost instantly stiffened as I delicately moved forward.

Once I made it a few feet away from the warmth and safety of the fogged glass, the blurry thing on the door came into view enough for me to make out what it was. My heart sank and my cheeks flushed at what I saw.

Hannah had left me a fucking french maid dress.

For a second, I froze. The dots weren’t difficult to connect. I was supposed to be her housekeeper, so she wanted me to dress up like a subservient little maid. But what else could I do?! I was tempted to scream out her name, but the last thing I wanted to do while buck naked was draw attention to myself. And hiding in the bathroom wouldn’t do anything for me. Wrapping the outfit around myself as a towel crossed my mind, but it looked small and that felt too risky if I ended up outnumbered even two to one. Ugh, why did it have to be frosted glass for the shower? If there was a curtain, I could use that as my makeshift towel/bathrobe.

Groaning more loudly than before in pure frustration, I snatched the hideous thing from the door. What other choice did I have?

I was going to put it on.

[SDS]

Great story LL xx

Funny enough I once drafted but never finished a very similar story... but the 'maid' was a cleaners daughter covering for her Ill mother who gets caught by the rich girl and blackmailed into a maids dress haha

[*Lady Lucia*]

CHAPTER THREE


Jess

I couldn’t believe I was dressed like a fucking MAID.

It was so embarrassing. Even without my glasses, I could see and feel all the things that were wrong. The whole dress was too small; my breasts were uncomfortably smushed behind the fabric up top, and the skirt sat so high on my thighs that I was worried that something as simple as walking would risk exposing me while I didn’t have underwear for protection. The outfit also awkwardly clung to me a little bit, since I was still damp from not being able to dry off after my shower. My hair was a whole different story, but I was just going to have to deal with that until I got my hair dryer and brush back.

The worst part? This was probably exactly what Hannah wanted.

Well, I’m sure she would have been satisfied with me being naked as well. Either way, I now had to brace myself for Hannah and company poised to take countless photos the moment I opened the bathroom door. Wait, speaking of smartphones, where was mine?? With my blurry vision, I had only been focused on the lack of clothes and towels in the bathroom. Toiletries, too. Now that I was thinking about potential ways out of this mess, I realized that I didn’t even have the option of calling Hannah’s parents. The girl had taken my fucking cell phone.

Now that I was stalling, I took the time to examine my surroundings a little more carefully. Right away, I noticed there was something I missed. In my half blindness, I had mistaken it as something to do with the soap dispenser by the sink, but upon closer inspection I found that my glasses were waiting for me.

It was anything but a relief. True, I would be able to actually see, but at what cost? There was a reason I always wore contacts. The prescription required for my horrible eyesight didn’t have a lot of cheap options for glasses. And, since I couldn’t afford the prettier ones, my ‘last resort’ was an incredibly ugly pair. I hated, hated, HATED how they looked on me, and pretty much only wore them for studying when I was secluded in my dorm back at university. Even then I was on edge, as I had a roommate.

On top of that, this meant that Hannah had pilfered through my things while I was in the shower! My glasses had been stashed away in my backpack. While there wasn’t anything particularly private that I had brought with me for the summer, I still felt violated thinking about the blonde teenager strutting into my room and checking out all my stuff. God, I could just imagine her turning my suitcase upside down and ruining the way I had everything perfectly folded. And then there was my precious laptop; it was password protected, but it would still be frustrating if she ‘confiscated’ it along with my phone.

‘One thing at a time, Jess.’ Projecting like that wasn’t going to help with my current predicament. Taking a deep breath, not particularly ready to face the reality of how I looked, I put the glasses on anyway.

It was even worse than I imagined. From the waist down, I looked like a total slut. My thighs were fully on display, and a quick turn to check out my backside confirmed that the skirt barely, barely covered my ass. The top half was the total opposite. While some tight bras and tops would make my boobs ‘pop,’ the neckline of this maid outfit was high enough that my chest was just squished and nothing more. The perky Cs I was normally so proud of looked at least half their normal size without a bra for support and when trapped behind the awful dress.

My hair actually looked better than expected after a good cleaning, but I knew from experience that it would get a little messy if left to air dry without proper care. And, without make-up, my face looked a lot more youthful. Then there were the glasses themselves, which were as horrible as always. Overall, my appearance was the weirdest combination of immature, slutty, and awkward. And there wasn’t a damn thing I could do about it.

Nervously padding over to the bathroom door again, cringing at the continued wave of coldness against my bare feet, I cracked the door ever so slightly. “Hannah?” I quietly asked. In my mind, I had been aiming for something a little more assertive. After all, I was supposed to be the one in authority here. But in my current state, I felt slightly at the blonde’s mercy, at least until I was dressed in my own clothes again.

To my surprise, no one was waiting for me. Similar to when I found my glasses, I felt more worried than relieved. If not right outside the door, then where was she? Around the corner, waiting to get a more full picture of me when I stepped out into the hall? After all, I currently had a door to hide behind. “Hannah.” Finding a little more backbone as the frustration of the situation began creeping in and outweighing the embarrassment, I curtly addressed the girl. “Hey. Bring me back my things. Right now.”

Silence. She and her girlfriends were so giggly earlier; either they had a lot of self control at the moment, or they weren’t here. But all it would take was one photo for this whole thing to get more complicated. “Hannah!” I yelled. So much for not drawing attention to myself.

Nothing.

Fuck it. Exhaling in annoyance, I crept out into the hallway, bracing myself to skitter back to the bathroom at the tiniest sound. Actually, wait. Running to my room was a better idea. Being conscious of the fact that my feet were still slightly damp, I made a beeline for the door as quickly as I could manage while being safe about it. Of course, there was always the daunting thought that Hannah could just as easily be waiting in the guest bedroom. If she would shamelessly dig through my bags, then what was stopping her from waiting in there for me?


Instead, I found a totally different issue waiting for me: The door was locked.

Groaning at the unexpected obstacle, I aggressively jiggled the doorknob for a few seconds in the hopes that maybe it was just stuck or that Hannah’s latest trick wouldn’t hold. No luck. The door held fast, and none of my efforts to make it budge seemed to matter. I had felt so close to a fix, and it was such a psychological blow for that hope to be snatched right away from me. Still in that odd limbo of embarrassed and pissed off, I stormed down the hall towards Hannah’s room. She was bigger than me in every way, but I’d still prefer slightly baggy clothes to the maid dress.

Just like the guest room door, hers was locked. “Come on!” I whined. What about her parents’ closet? It felt a little wrong borrowing clothes from my employers, but that was still a better alternative than my current getup. All the upstairs doors were closed, so it was no surprise when the master bedroom was locked as well. For fuck’s sake.

I could always try the downstairs bathroom for a towel, or the laundry room to see if there were any clean clothes to change into. Hell, I would strongly consider putting on one of Hannah’s used outfits if it meant keeping her from the victorious smirk I could already visualize if I walked outside wearing this. From what I could tell from the faint female voices in the distance, she and her friends were still outside. And it was definitely more than three girls at this point. If she had gone through the trouble of making sure all these doors were covered, it was safe to assume she had been just as thorough downstairs. Fucking brat.

It didn’t matter. I was the babysitter here, and she was the entitled eighteen year old. The girl in the bathroom mirror didn’t look particularly intimidating, but that was before I had gotten worked up by the audacity of the teenage blonde who clearly didn’t respect me in the slightest. But she would.

Not wasting another second circling the house in the hopes for something different to wear, I just swallowed my pride and made my way downstairs. Taking a deep breath in the kitchen, followed by several more with closed eyes in an attempt to calm my nerves, I finally stepped back outside.

My eyes instantly went wide at the sight before me. How many friends had Hannah invited?! From what I could tell, there were at least ten girls clad only in skimpy bikinis. A handful were hanging out in the pool, but most of them were sitting or lying under the sun and gossiping about who knows what. The self conscious girl within said I could easily be the subject of the giggling. Even worse, there was alcohol everywhere. Empty cans of beers and seltzers littered the ground, each and every girl had a drink in their hand, and it was easy to spot a handle of vodka sitting near the bitchy blonde who had started all of the trouble.

“HANNAH.” A bit more shrill than I had wanted, thanks to the unexpected crowd and illegal mess that I had literally been hired to prevent, I tried not to let my first impression ruin everything. Striding forward with a purpose, I ignored the other girls and set my sights on Hannah. She was lying in the same lounge chair as before, and hadn’t done much in response to my arrival; she just slightly shifted her head to glance my way. “Inside. Right now.” I didn’t care about privacy in terms of her reputation with her friends. Admittedly, it was mostly because it would be easier for me to handle this without an audience.

Considering how I was dressed, I had braced myself for laughter. That’s definitely how my university friends would react to seeing me in something so ridiculous. These girls, however, didn’t know me. If anything, they looked more annoyed than anything else. And I was about to see why.

“What’s up with your maid, Hannah?” one of the brunettes in the pool asked, “Is she allowed to talk to you like that?”

I could feel myself starting to fume even more. It was so rude to talk to someone right in front of their face, and doubly so when that girl was your elder. The only reason I didn’t bite her head off is because I wanted to walk the line between collected and authoritative. That, and this was between me and Hannah.

“I-” I opened my mouth to assert my demand for Hannah to meet me inside, but that’s as far as I made it.

“No, she’s not,” Hannah said, “But little Jessie is a recent hire. She hasn’t learned how things work around here. Although she’s not a ‘maid.’” For a moment, I thought she was actually defending me. A stupid notion, considering what I was stuck wearing thanks to her thievery. “She’s my housekeeper for the summer.”

“What’s the difference?” the girl next to her asked.

“It’s simple. Maids are only responsible for all the inside chores. Jessie will be handling everything outside, too. Which is good, because we really need someone to clean up this mess.”

It took a conscious effort to keep my jaw from dropping. Was Hannah serious?! Stealing all my personal possessions was already over the line, and now she was still pretending like this was all normal? “Hey. Hannah-”

“Jessie.” Hannah set her glass down hard enough that I could actually hear her attitude from the gesture. “You’re serving as my housekeeper this summer, right?”

NO.

That’s what I wanted to scream. Before I had been pushed into the pool, I was prepared to drop the whole ‘housekeeper’ act and lay things out for the spoiled, presumptuous brat. To hell with her parents’ idea that I present myself as something more posh. But now that I was standing in front of all her friends, I was quickly hit by a number of potential complications.

It probably didn’t take twelve girls to pull off the prank that led to me being out here dressed like this. Unless all of them were acting their young hearts out, which I wouldn’t necessarily put past a bunch of pretty rich girls, there was a good chance some of them actually thought I was a housekeeper and nothing more. If I asserted why I was actually here, how much respect was I going to get if they all saw what Hannah did to me within the first hour of my arrival? And unless I could get my phone back, which could be hidden anywhere at this point, I had no means of reaching her parents. Well, my laptop had their numbers in an email somewhere, but Hannah had definitely gone through my things. What if she took that, too? Even if I was supposed to be babysitting the girl, how was I supposed to get a whole party of irresponsible eighteen year olds to take me seriously?

Then there was the other thought. What if part of this was about their family’s social standing, and less about putting Hannah at ease? Any of these girls could gossip to their own parents about anything they witnessed here, and maybe it would reflect poorly on Hannah’s parents if their recently graduated daughter needed supervision? It’s not that I owed them anything at my own expense, especially if something like that was never communicated to me, but all of this would be for nothing if they decided not to pay me for ‘breach of contract’ or whatever.

Regardless, my inner fire was dwindling against the peer pressure before me and the embarrassment of how I looked. Screw it. “Not your housekeeper,” I replied. Waiting until I could get a one-on-one with Hannah sounded more appealing, but that didn’t mean I had to fully roll over. “Your parents hired me, Hannah, and they gave me specific instructions to follow.” Read between the lines, girl. As for everyone else, I was hoping it would make it sound like I wasn’t a total pushover.

My hopes for some semblance of authority and respect were quickly dashed when the same girl in the pool spoke up. “I can totally see her vagina.”

It was said so casually, but the mortifying observation was enough to make me gasp and throw my hands over my crotch while trying to pull the skirt down a little bit as well. The motion caused the back to ride up and expose part of my ass; my immediate instinct was to cover my backside somehow as well, but I fought that urge when I realized no one was behind me. It felt wrong to allow it to stay like that, but what else could I do?

“She’s kind of a slut,” Hannah said, “A shameless little lesbian, too. She probably couldn’t resist showing herself off when she saw all these hot girls in bikinis. Seriously, Jessie. You did bring something more modest, right? Or underwear, for that matter?”

“I’m not- I didn’t-” Still recovering from the fact that all the girls in the pool probably got a good look at my womanhood before one finally pointed it out, I wasn’t prepared at all for the subsequent accusations. Now that I had allowed the ‘housekeeper’ thing to continue, of course Hannah could fucking say that this was MY dress. “I’m not a lesbian!” I finally exclaimed after the flustered sputtering. For some reason, that felt like the most important thing to clarify. Not only was I very much a straight girl, but the suggestion that I dressed myself like that to get attention was outright false. There were just too many fronts to fight on. I wasn’t really a housekeeper. I wasn’t a slut. My name was JESS, despite the constant use of ‘Jessie’ recently. And all my real clothes and underwear were in the locked guest room.

Trying to say all that out loud, however, would be a total mess.

“Jessie.” Hannah snapped her fingers twice. Vaguely gesturing to the poolside around her and the other girls, she said, “No more talking. Be a good little girl and clean all this up.”

That same fire from earlier started pushing up. Narrowing my eyes and looking right at Hannah, I started saying, “You-”

“Yes, Hannah!” The two girls beside her said it in perfect unison. Like twins, totally in sync, despite how they looked nothing alike. It wasn’t intentional, apparently, as they both looked at each other in surprise before bursting into a fit of giggles.

“That’s right,” Hannah said, “That’s how you’re supposed to respond, Jessie. Thanks, girls. See, they have maids, too. I know you’re new to this whole serving thing, so we’ll give you a pass or two. Now, let’s try again.”

“But-”

“Jessie. Clean up this mess. Now.”

Blushing deeply and still clinging to my skirt in the name of keeping myself covered, I reluctantly responded the way I was just instructed. “Yes, Hannah.” What else was I supposed to do? I had already resolved to play along until I could find a private moment with the girl, so any pushback would make me look worse and worse. No longer prepared to face off with the bitchy blonde, I just wanted to go back inside and kill time until her friends left. No, not kill time. I was going to find a way to pry my bedroom door open.

“One more time, Jessie,” Hannah said, “So you can get used to it. You’re welcome. Now, be a good little maid and clean up this mess.”

Sighing in defeat, I muttered, “Yes, Hannah . . .”

[*Lady Lucia*]

CHAPTER FOUR


Jess

Right away, I realized that my plan might not be as simple as I expected.

The whole point of begrudgingly going along with the bullshit role I was trapped in, thanks to Hannah’s parents and my own inability to sort things out with their daughter when an audience was around, was so that I could ‘do my job’ and avoid the girls while trying to find myself something less humiliating to wear.

Surely not all the doors locked, right? I’m sure there had to be something around. I hadn’t tried the downstairs rooms yet, and I’d honestly prefer to wear one of Hannah’s dirty outfits in the laundry room than the way too small french maid dress. However, I couldn’t exactly retreat inside when the blonde eighteen year old just demanded that I clean things up around the pool. As her ‘housekeeper,’ it’s not like I could pick and choose which messes I wanted to clean up. The title had sounded fine when I thought it was just some posh term that implied I had some degree of authority, but I probably would have thought twice about it if I knew how old Hannah was before arriving on her doorstep.

Hannah and her friends all looked like bikini models, with perfect hair and perfect bodies as they lounged by the pool. I would have expected rich girls to have some class to go along with such pristine appearances, but perhaps they were used to being waited on hand and foot. Rather than simply placing their empty drink cans down on the numerous side tables, most of their trash was strewn about the side of the pool on the ground. That came with two separate problems. One, there wasn’t a recycling bin out here, and there were only so many cans I could hold at the same time. Two, the skirt I was wearing already threatened to expose me with every step I took while standing. How was I supposed to bend or squat to pick things up without showing off everything?

“Well, Jessie?” Hannah said. She vaguely gestured to the area surrounding her, “Hop to it. And what do you say?”

Swallowing my pride, and a good bit of anger and frustration as well, I repeated the demeaning phrase. “Yes, Hannah.”

Normally, squatting was the safer play. But not this time, when I was pretty sure the whole dress would ride up on both sides and leave literally nothing to the imagination. Choosing the lesser of two evils, I approached the first few cans I saw and bent over to retrieve them, purposely keeping my backside away from the nearby girls. I could feel the outdoor air on my lower cheeks, and immediately blushed at the thought of how I must look from behind. My proximity to the nearest girls also made me feel self conscious, in that my hair was wet from my shower and no towel, while pretty much all of Hannah’s friends were perfectly put together.

I managed to secure an armful of cans without mooning anybody, and suddenly had the hopeful thought that perhaps a lack of receptacle would work to my advantage. Taking a second to adjust the back of my skirt and praying it would cover me, I turned back towards the house. Drop off the empty cans, and then take advantage of the solitude and the empty house to hunt for my things instead of coming back out.

“Where are you going, Jessie?” Hannah asked, after I had barely taken a single step.

Feeling self conscious all over again as her voice cut through any other little side conversations and brought the attention back to me, I tried to glance over my shoulder without fully stopping. “To toss these,” I said, “I’ll be right back.”

“Taylor will go with you! She can get the door. Then come back right out, okay?”

Was I that transparent? My intentions weren’t supposed to be so obvious, especially since I had feigned obedience. Or maybe Hannah was just micromanaging me and it happened to screw with my idea. “Yes, Hannah,” I muttered. So much for getting a moment to myself.

With a different bikini clad escort every time, as the bossy blonde clearly enjoyed sending one babysitter after another to open the sliding glass door for me and linger so I couldn’t stray beyond the kitchen, I gradually cleaned up all the cans from the poolside. No one made another comment about my exposure, but there were plenty of whispers and giggles going on throughout the experience. With only one hand to cover most of the time, I could only imagine how often the girls caught a glimpse of me despite how carefully I tried to position my body and keep the too-short skirt down. There were just too many of them around, which made it impossible to find a modest angle for my body most of the time. Next, I was made to scoop all the leaves out of the pool, and then clean up a few more empty seltzers that the girls had finished by the time I finished that task.

“Come here, Jessie!” Hannah called out to me after my latest trip to the kitchen. I was already headed back her way anyway, though of course now it seemed like I was doing so because she summoned me. Once I was close to her chair, and trying not to blush as the group of girls all watched the interaction with interest and curiosity, she held out an unopened can. “Here. You look thirsty.”

“No, thanks,” I said. My hands were devoted to keeping my outfit in place now that I wasn’t stuck doing chores, though I had to resist wiping a bead of sweat from my forehead. Every other girl here got to lounge in a bikini, but I was the one moving about in a dress. The summer heat wasn’t my friend after nearly a half hour of work, though the constant stops inside kept me from fretting about burning like before. Regardless, I wasn’t about to drink on the job. I had enough working against me already.

“Come on, Jessica,” she smiled, “Live a little. Tell you what? Shotgun the whole thing, and you can go inside.”

It really was that easy. “Fine,” I said. Taking the can from her, I cracked it open without a second thought. Anything to let me go inside so Hannah could stop bossing me around. Besides, it was just one drink. I may have been small, but I wasn’t that much of a lightweight. Although the smile and the lilting way she said my full name didn’t exactly put me at ease. Was it really that difficult to stick with ‘Jess?’

“Good girl,” Hannah said, “Okay, you have thirty seconds. Starting . . . NOW.”

Wait, what? Even though the word ‘shotgun’ was involved, I didn’t expect her to put a timer on my chugging. With such a full audience, however, I immediately fell for the peer pressure. Lifting the can to my lips, I tilted it back and began drinking. I wasn’t the best at downing things quickly, and the coldness and the carbonation of the hard seltzer served to be a more daunting challenge than expected. Taking as big of gulps as I could manage, my eyes widened when one of the girls called out ‘Fifteen seconds!’ There was definitely more than half a can left, so I redoubled my efforts in order to avoid Hannah going back on her word or something if I failed the task I didn’t realize I had signed up for until it was too late.

Near the end, most of the girls joined in chanting, “FIVE . . . FOUR . . . THREE . . . TWO . . . “

Finishing off the last of it, I sharply exhaled as I removed the cool metal from my lips. Done. I felt a little bloated from both the bubbles and the speed at which I downed the drink, and there was also a hint of internal warmth from the alcohol making its way into my system. Unless I was imagining the latter.

My victory was short lived, however, as Hannah sat up and brought the attention back to herself. “Good job, Jessie. Okay, girls! Let’s go inside.”

Wait, what?

It didn’t take me long to sort out that Hannah technically never said I would be going inside alone, although her phrasing had hinted pretty strongly at it. As she and her friends started to get up and collect whatever drinks they had yet to finish, I spent a few seconds debating how to proceed. My whole plan had hinged on getting back into the house alone, but it’s not like I could complain. I was outnumbered, and any number of the girls around me could come to Hannah’s defense about what was said. Besides, it was the blonde’s house, and I wasn’t exactly in a position to tell her she couldn’t go inside.

So, I simply followed the group of girls, making a point to slightly lag behind. Anything to keep my backside from being revealed again as I held down the front to obscure my womanhood that was also on the precipice of exposure at pretty much all times. The price to pay for being the last one inside was that I was once again the center of attention as all the girls had congregated around the spacious kitchen island.

“This isn’t your first housekeeping job, is it, Jessie?” Hannah asked, only after I slid the door closed behind me.

I had been a babysitter for quite some time, and a pretty professional one at that; doing a few chores came with the territory, often after the kids went to bed. And, since Hannah had put me on the spot, I couldn’t overthink my answer. “Of course not,” I said. One, this was supposed to be a similar job to what I was used to anyway. Two, any confessions about being inexperienced with wealthy clients and unprepared for an unexpectedly older teenager would give her more room to define the job for me. More than she was already doing, that is.

Hannah set her glass down with an idle smile on her face. “Good. We’re going to put some clothes on and hang out in the other room. You should get started on snacks.”

Right. I had completely forgotten about that task given to me earlier after everything that had transpired since then. The prideful babysitter within was tempted to berate this girl for talking to me in such a way, but we were well past that. I was supposed to be in charge, sure, but that’s not exactly where things stood at the moment. “Yes, Hannah,” I said. Still playing along, in the hopes that the girls before me would scatter and I would finally have a second to breathe.

That was somewhat the case, though Hannah insisted I stay in the kitchen to work. Once she and her friends were settled, I’d be told what to do next.

What did rich girls even snack on? Hopefully something easy, as their taste in alcohol clearly wasn’t as snobbish as I might have expected from someone who grew up in a house like this. After a minute of searching, I found a pantry full of junk food that would hopefully suffice. I found a few appetizer bowls and took the effort to prepare the snacks beyond the boxes and bags they were packaged in, then made a small pile of fruit on the counter as well. Ever the responsible girl, I at least had to try to offer some healthy options.

It didn’t take long for the girls to filter into the spacious living room. Bringing them snacks was only the first part of this new ordeal. I figured out quickly that my new role would be something of a waitress, or perhaps female butler. Despite my insistence to Hannah that I knew what I was doing, this was all new to me, and I couldn’t think of a way to avoid being taken advantage of.

Calls of ‘Jessie!’ were nonstop. A different voice almost every time, requesting a new drink or a snack refill. Every time I delivered something, I was to clear the various surfaces of used bottles and glasses as well. My other task was to clean the kitchen from top to bottom; according to Hannah, it had to sparkle by the time I was done. However, I’d barely get three minutes into one of the many areas required before I had to drop everything to tend to the girls.

A number of them had decided to swap to liquor, and I also became their bartender. Rum and coke, vodka cranberry, gin and tonic; their requests were simple, but ensured that the counter was constantly full of liquor and mixers. At first, I attempted to barely put a splash of liquor in each drink, as a way to subtly control the situation. After a number of complaints that I was making everything too weak, however, I gave up and actually prepared alcoholic drinks for the group of eighteen year olds I was supposed to be watching.

All the while, I cleaned whenever possible, but hardly seemed to be making a dent due to all the interruptions. I kept trying to think of ways to get out of my predicament, but found it difficult to think most of the time. I needed to get upstairs and break into the guest room somehow, but I was summoned so frequently that there was never a minute to slip away. And with all the gossiping and giggling and other piercing girly noises from one room over, it was impossible to focus.

I also hadn’t gone to the bathroom since before my drive. First I had been reeling from the surprise of Hannah’s age, and my next trip to the restroom had me too concerned with getting all the chlorine off. Add a chugged can of hard seltzer to the mix, and I found myself with a possibly broken seal and an urge that was no doubt heightened from something that would have naturally come up around this time anyway.

Stepping away to get into my room and get out of the degrading maid uniform was one thing, but I was well within my rights to take a bathroom break. Hannah and company would just have to deal with a minor delay if one of them needed something. Even so, I found myself tip-toeing out of the kitchen to avoid having to deal with a conversation about it. The cool hallway was almost worse on my bare feet than the kitchen tile due to vent placement, and I ended up faced with a series of closed doors. Which one was the bathroom, again? It didn’t matter, because every single door I tried was locked. Just like upstairs after my shower.

Inwardly groaning to myself when I heard one of the girls call out for me, I ducked back into the kitchen to approach from that direction. Taking the empty glass, as well as two half empty ones that a couple of the other girls decided they wanted topped off, I retreated back to the kitchen. Instead of getting to that right away, I made a quick trip upstairs, only to find that the bathroom I recently showered in was also closed and locked. Seriously?!

After an aggressive jiggle on both the bathroom door and my guest bedroom on the off chance that one of them would yield, I dejectedly went back downstairs. Taking care of the drinks, I returned to the living room and was half tempted to ask Hannah why she was keeping everything locked up. Surely her friends would need bathroom breaks as well, especially since they were drinking so much. But asking in front of an audience would be so embarrassing. Hannah’s babysitter–or rather, housekeeper–essentially asking permission to use the restroom? No, thanks.

Instead, I threw myself back into my work. Making the kitchen shine in an effort to avoid Hannah finding another excuse to make the afternoon difficult, and constantly waiting on the girls whenever they called me. After another hour, however, the urge became too pressing to ignore. In fact, it was much worse this time around due to the fact that I had put it off for so long. Hannah and her friends seemed content to drink and snack and hang out to their hearts’ content in the other room, and I couldn’t wait any longer.

The next time I returned to the living room with a new bowl of chips and a refill for Hannah herself, I paused next to her and hoped that the fact that I was standing and she was sitting would at least give me a modicum of authority despite my getup and the fact that I had been serving them for half the afternoon. “Hannah, I need to use the restroom,” I said. Direct, and to the point. Even if it was embarrassing to say it in front of a whole room of eighteen year old girls. “And all the rooms are locked.”

“That’s not a very polite way to ask,” Hannah said. Brushing back her hair with a smug smile, she glanced up and met my eyes. Clearly not daunted at all, despite the height disadvantage she had against my standing self. “Try again, Jessie.”

Swallowing my pride, I began saying, “May I please-”

“Ah, ah,” Hannah held up her hand, “What do you say when I tell you to do something? Try again, Jessie.”

I was tempted to slap her. But with all her friends here, something told me that wouldn’t end well. “Yes, Hannah,” I said. Starting with the housekeeping phrase she was pushing on me, I then went on to ask the full question. “May I please use the restroom, Hannah?”

“Hmm,” she mused. Deciding rather quickly, Hannah said, “Maybe in a minute. First, I have some questions for you. We all do.”

[*Lady Lucia*]

CHAPTER FIVE

Hannah

This was going better than I thought it would. Way better.

Especially since it’s not like I had a plan. My friends had already been set to come over, as it’s not like having a ‘housekeeper’ meant that I was grounded or anything. But once I had decided to put little Jess in her place, having power in numbers certainly wouldn’t be a bad thing. The brunette was young, and small, and poor; why else would she take a summer job? And with the lovely title my parents had given her, as well as her inexperience when it came to my lifestyle, it would be simple enough to push her into the role she had technically signed up for.

Drinking with my friends set her off just like I hoped it would, and it was SO satisfying to watch her flail backwards into the pool. The way her wet top hugged her chest, however, was a reminder of how obnoxiously well endowed she was. Something would need to be done about that ASAP. And, sure enough, she gave me an opportunity to really screw with her. Taking a shower.

I took half of my friends upstairs once I heard the water running, and put them to work stealing everything in the guest room Jess had chosen for herself. While they handled that, I took the job that was both more fun and more risky. I soundlessly slipped into the bathroom and scooped up Jess’s pile of wet clothes on the floor, followed by the clean ones she had left neatly folded on the counter. All the while, I stayed low, making sure my blondeness and my movements wouldn’t be easily noticed through the fogged glass. Last but not least, I swiped all the towels; even the hand towels, so the naked girl wouldn’t have a single thing to dry off with.

When I returned to the guest room to check on my friends’ progress, I was happy to see an empty room waiting for me. Jess had just arrived, after all, so it’s not like she had unpacked much. To finish things off, I locked the door. That would keep her out for a while. And, if she somehow picked the lock or climbed in from the outside, then she would learn that her efforts were totally wasted.

Just when I was relishing in the fact that I had stranded my babysitter buck naked in the bathroom, as I went so far as to lock ALL the doors in case she decided to pilfer through my stuff or my parents’ closets out of desperation, I thought of something much better for the girl. I had no idea how long Jess would be in the shower for, so I was suddenly running down the hall in my bikini to find the french maid outfit. It was more of a costume than a uniform, designed to be slutty for girls who liked to wear such things on Halloween. Or, in my case, to use for roleplay every now and then. I had a number of costumes for both girls and guys, because I appreciated both genders equally.

Only for Jess, this wasn’t about sex in the slightest. I just wanted to visually seal her in the role of ‘housekeeper.’ And, if she happened to look a little slutty at the same time, all the better.

I snuck into the bathroom again. The french maid number was left on the back of the door, and I also swapped her contacts out for a pair of ugly glasses that Taylor found deep in one of the pockets in Jessica’s backpack.

Shame there wasn’t a way to install a few cameras in the room to watch the girl’s reactions to what I had stolen and left behind. At least, not at the time. Maybe I could order some cameras for a few rooms of the house. Correction; maybe Jessica could order them. I had her wallet now. Her credit cards were mine to play with, and I assumed her driver’s license would have the zip code required for online purchases. But that was fun I’d have to have later. For now, I was happy drinking with my friends and waiting to see if little Jessie opted for nudity, the slutty maid costume, or something ridiculous like finding curtains or a rug to cover herself up.

To my delight, she went with the costume. And it was amazing! The top half squished and flattened her breasts to the point that she no longer looked bigger than me, and the skirt showed everything. I don’t think even Jessica was aware just how often she was exposing herself. Because my friends and I were all seated by the pool, some in chairs and some with their legs dangling in the cool water, we all had great angles to check her out.

The subservient girl was totally bare down there. Her pale little ass was nothing to write home about. And, most importantly, her tiny slit was easily visible again and again from both the front and the back. With her modesty being stripped away, as well as her dignity while cleaning up after us like a proper maid, I could tell that none of my friends would take little Jessie seriously moving forward. On top of everything else, I took a lot of pleasure in how hot I looked with my perfect hair and perfect body in comparison to Jessica’s damp hair, nerdy glasses, and pathetically petite frame wrapped up in a slutty french maid costume.

For a while, I just bossed her around with the help of my friends. Not only for the fun of it, but also to get Jess used to her role moving forward. If my parents were dumb enough to label her a ‘housekeeper,’ and if Jessica was enough of a pushover to allow all of this to happen with very little protest, then I wasn’t going to relent any time soon. Instead of a babysitter, I was going to have an obedient little maid for the next six weeks.

It was a great afternoon. My girlfriends and I got to hang out and drink to our hearts’ content, and for once we didn’t have to take turns dealing with snacks and clean-up. Instead, we simply had ‘Jessie’ do everything for us. I could tell that Jess wasn’t a huge fan of her full name, but her little reactions to the alternative nickname made it clear that I had found something she liked even less. And, after making her serve us for a few hours, she voiced that she needed to use the bathroom. Better yet, she politely asked for permission after just the tiniest bit of prodding.

She was at her most vulnerable yet. Dressed up like an obedient slut, worn down from all of our orders, and needing to pee. The perfect time to strike.

“So, Jessie,” I began, enjoying the subtle twitch of distaste that always seemed to follow my new name for her. Give it time, Jess. You’ll get used to it. “You said you’re not a lesbian?”

“No!” she immediately snapped.

“You didn’t say that?” I clarified, “So you are a lesbian, then?”

“Ugh, no! I’m straight.”

Boring. But also predictable.

Just to my left, Lillian was the first to pick up on this new game I was starting. Granted, it wasn’t that new. Jess wasn’t the first girl we had grilled. There were plenty of parties where my friends and I were able to overwhelm a girl we wanted to destroy with difficult questions. And, when said questions came from all sides, it seemed more like intense group curiosity than a targeted attack. “How many times do you masturbate a day, Jessie?” Lillian asked.

Jess’s cheeks turned SO red. “W-what? That’s- that is none of your business!”

“Jessica.” Opting for the full name this time to get her attention in a different way, I flatly said, “Answer the question. If you want a break, then act like one of the girls.” Gesturing to all the bikini-clad high school graduates around me, I explained, “We do truths like this all the time.”

“But-”

“Yes, Hannah,” I said.

“Yes, Hannah . . . ” she echoed.

“Good girl. Now, how many times do you masturbate a day?”

The look on her face told me everything. There was absolutely no way to safely answer a question like that. Because she was right; it was super personal. Any number would basically be telling the whole room that she pleasures herself. Girls that were confident in themselves and their sex lives would be able to say anything and not give a shit what others thought. But it was clear that Jess wasn’t like that.

Amusingly enough, her answer was exactly what I thought it would be. Nervously glancing away, the little brunette mumbled, “Once . . . ”

Easily the tamest answer without seeming like a total prude. I actually had no idea whether or not it was the truth. Just because Jessica was a doormat didn’t necessarily mean that she didn’t take time to play with herself multiple times a day. Girls could be unpredictable like that. I didn’t have time to press about it, however, as Lillian followed up right away. “Just once? Cute. How do you do it, Jessie? Fingers, or toys?”

“Umm . . . ” One look towards me and my stern gaze was all the girl needed to comply. “Fingers.”

It was difficult to tell whether it was the questions that were causing the girl to fidget, or the need for the restroom. While it wasn’t quite the cliché bathroom dance, it was close. Since Lillian was the one interrogating Jessica at the moment, I was free to look the slutty maid up and down. The most noticeable movement was the way her hips were slowly gyrating as she adjusted her thighs and posture again and again. Then there were little things, like the way her bare toes would twitch, and how her hands couldn’t stay still.

True, it could have been the cold floor under her feet, or the fact that she was the center of attention during the uncomfortable line of questioning. But I knew better. If it was just those things, then the college girl would have pushed back harder against the barrage of inappropriate questions. No, little Jessie was trying to keep from bursting, and playing along only because it felt like the only way to get the bathroom key. If only she had managed to think outside the box–our property was pretty secluded, and sneaking outside to pee behind a bush would have probably been more comfortable than subjecting herself to all of this.

Taylor spoke up when Lillian was done asking about fingering technique, and porn preferences, and a number of other questions that made Jess stammer out the most vanilla and minimalistic answers in an attempt to save face. “What’s your favorite sex position?”

Jessica’s face went white.

In contrast, my eyes lit up. I knew it. I KNEW IT. She was a fucking virgin! If she had a real answer to the question, even something as boring as missionary, her reaction would just be awkward and hesitant like it was when it came to her masturbatory habits. Instead, there was a distinct panic in her expression and body language. The kind where she’s about to be caught in a humiliating truth in front of the worst audience possible. Worse than peers; we were girls she was supposed to be in charge of. And there was no getting away from this. Not if I had anything to say about it. “Jess.” My tone was gentle, as I gazed at her with a fun combination of pity and curiosity. I wondered if she caught that it was the first time I had used her preferred name in quite some time. “Have you never fucked a guy?” Less scary than the V word, but still with a swear in there to make the question blunt and a tad intimidating.

Jess

This was my worst nightmare.

So far, I had managed to avoid anyone finding out about my virginity. At university, I would simply lie by omission. It was easy enough to imply that I had experience in the bedroom, and it’s not like it was a total lie. I had done pretty much everything except penetration. But now Hannah was calling me out, and I was totally on the spot. I was a lot better at half-truths than flat out lying, and it sounded like she already knew the answer. But could all of her friends tell, too?

“That’s none of your business,” I meekly replied. Same attempt as before, and I could tell right away that it wasn’t going to stop the blonde from pushing the matter.

“Jessie, tell us the truth,” she said, “Or would you rather continue your chores naked? And without those pretty glasses?”

She wouldn’t! The sarcasm in regards to my glasses hardly registered, as I was too busy worrying about being stripped. While Hannah had claimed to her friends that this mortifying outfit was mine, technically it belonged to her. Which meant she could take it back if she wanted to. Plus, the urgent need to pee was still there. “Hannah, please . . . ”

My plea fell on deaf ears. “Answer the question, Jessie. Have you ever fucked a guy?”

Wincing at the crass way to describe the first I had yet to have, I blurted out the simple answer before I could stop myself. “No . . . ” I didn’t even bother explaining myself. My answers to the deeply personal questions so far had been bad enough; they didn’t need to hear about my second and third base experiences.

A few hushed whispers and giggles filled the room, but Hannah didn’t partake. Instead, she kept her gaze trained on me. “And what does that make you, Jessie?”

I knew what she wanted to hear. With a lump in my throat, I practically whispered, “A virgin.”

“What was that? Say the whole thing, girl.”

“I’m a virgin.” My lip quivered the slightest bit as I said it for the whole room to hear. Deep down, I knew it wasn’t that big of a deal that I hadn’t had sex yet. But that internal logic was impossible to listen to when this was the very first time I confessed my virginity to anyone, ever. And, of all people, it was to Hannah.

With a smirk, the blonde picked up one of the water bottles I had recently delivered the girls. Apparently they knew how to hydrate amidst day drinking. Rather than tease me about my lack of sexual experience like I expected, Hannah simply held out the water from the fridge. “You look exhausted, Jessie. Sweaty, too. Why don’t you show us those chugging skills again?”

But- but-
No way. I couldn’t drink a whole bottle! My bladder was already feeling a bit bloated and pained from waiting so long to speak up about my need to go. The last thing I needed was a drink. “Hannah-”

“Go on, Jessie. Then we’ll talk about your break, okay?”

Okay. I guess that was fine. If I was able to use the restroom immediately after downing all the water, then it wouldn’t be a problem. And, as I had already learned, arguing with Hannah was impossible. It would just drag things out and result in her getting what she wanted anyway. So, resisting the urge to sigh, I simply said, “Yes, Hannah.” Unscrewing the cap and steeling myself with a huffed exhale, I pressed the bottle to my lips and tilted it back.

The first half of the process was fine as I opened my throat and allowed the cool liquid to flow through as quickly as possible. The rest, however, made me regret the decision to do as I was told. As I drank, I felt an intense pressure on my bladder. Oh God, I had to go SO badly. Chugging more water was beyond counterintuitive, but I forced myself to keep going. Just a little more . . .

Gasping as I finished the last drop, and pressing my thighs together as tightly as possible, I was suddenly worried about my ability to walk to the bathroom without disrupting the delicate balance I had created with my posture. “There. Now, can I please have the key?”

“Hmm, what do you think, girls? Does Jessie deserve a break? Show of hands.”

Not a single hand went up in the air.

“And who thinks she should get back to work?” Hannah raised her own hand, and literally every girl followed suit. Putting on a mock pout, she said, “Sorry, Jessie. Majority rules. You’ll have to hold it. Now, how about a fresh round of drinks?”

“NO.” My voice came out a little more shrill than I had expected, but I tried not to let it discourage me. Volume was more important than tone. “Hannah, I need to use the bathroom. Like, now!” Like, desperately. “Look, just-”

“JESSIE. God, what the fuck? You’re supposed to be my housekeeper this summer. That means serving me like a mature, proper girl. Not acting like a pathetic little baby and whining about the toilet. You should have gone when you got here, or before your shower.” She stood up. Towering over me with each step forward, she demanded, “Now, are you my housekeeper? Or an immature brat? And for fuck’s sake, Jessie, stop fidgeting.”

Hannah placed her hands on my shoulders and jostled my body into a more proper stance, which was enough to cause the inevitable to happen. I had no choice but to slightly pivot one of my feet to keep from falling over completely in response to her movements, which slightly separated my thighs. It wasn’t much, yet it completely destroyed the dam I had been working so hard to maintain.

I was completely powerless to stop it. Tensing up, and gasping in horror, the floodgates opened and I began wetting myself right there in the middle of the living room.

[*Lady Lucia*]

Author's Note: Just gonna preempt the potential complaints. While there will be plenty of ENF parts to this story in Jess's future, the commission does call for wetting to be part of the story as well. As it's a bit of a hybrid genre, apologies to those who don't appreciate those story elements!

CHAPTER FIVE

Hannah

This was going better than I thought it would. Way better.

Especially since it’s not like I had a plan. My friends had already been set to come over, as it’s not like having a ‘housekeeper’ meant that I was grounded or anything. But once I had decided to put little Jess in her place, having power in numbers certainly wouldn’t be a bad thing. The brunette was young, and small, and poor; why else would she take a summer job? And with the lovely title my parents had given her, as well as her inexperience when it came to my lifestyle, it would be simple enough to push her into the role she had technically signed up for.

Drinking with my friends set her off just like I hoped it would, and it was SO satisfying to watch her flail backwards into the pool. The way her wet top hugged her chest, however, was a reminder of how obnoxiously well endowed she was. Something would need to be done about that ASAP. And, sure enough, she gave me an opportunity to really screw with her. Taking a shower.

I took half of my friends upstairs once I heard the water running, and put them to work stealing everything in the guest room Jess had chosen for herself. While they handled that, I took the job that was both more fun and more risky. I soundlessly slipped into the bathroom and scooped up Jess’s pile of wet clothes on the floor, followed by the clean ones she had left neatly folded on the counter. All the while, I stayed low, making sure my blondeness and my movements wouldn’t be easily noticed through the fogged glass. Last but not least, I swiped all the towels; even the hand towels, so the naked girl wouldn’t have a single thing to dry off with.

When I returned to the guest room to check on my friends’ progress, I was happy to see an empty room waiting for me. Jess had just arrived, after all, so it’s not like she had unpacked much. To finish things off, I locked the door. That would keep her out for a while. And, if she somehow picked the lock or climbed in from the outside, then she would learn that her efforts were totally wasted.

Just when I was relishing in the fact that I had stranded my babysitter buck naked in the bathroom, as I went so far as to lock ALL the doors in case she decided to pilfer through my stuff or my parents’ closets out of desperation, I thought of something much better for the girl. I had no idea how long Jess would be in the shower for, so I was suddenly running down the hall in my bikini to find the french maid outfit. It was more of a costume than a uniform, designed to be slutty for girls who liked to wear such things on Halloween. Or, in my case, to use for roleplay every now and then. I had a number of costumes for both girls and guys, because I appreciated both genders equally.

Only for Jess, this wasn’t about sex in the slightest. I just wanted to visually seal her in the role of ‘housekeeper.’ And, if she happened to look a little slutty at the same time, all the better.

I snuck into the bathroom again. The french maid number was left on the back of the door, and I also swapped her contacts out for a pair of ugly glasses that Taylor found deep in one of the pockets in Jessica’s backpack.

Shame there wasn’t a way to install a few cameras in the room to watch the girl’s reactions to what I had stolen and left behind. At least, not at the time. Maybe I could order some cameras for a few rooms of the house. Correction; maybe Jessica could order them. I had her wallet now. Her credit cards were mine to play with, and I assumed her driver’s license would have the zip code required for online purchases. But that was fun I’d have to have later. For now, I was happy drinking with my friends and waiting to see if little Jessie opted for nudity, the slutty maid costume, or something ridiculous like finding curtains or a rug to cover herself up.

To my delight, she went with the costume. And it was amazing! The top half squished and flattened her breasts to the point that she no longer looked bigger than me, and the skirt showed everything. I don’t think even Jessica was aware just how often she was exposing herself. Because my friends and I were all seated by the pool, some in chairs and some with their legs dangling in the cool water, we all had great angles to check her out.

The subservient girl was totally bare down there. Her pale little ass was nothing to write home about. And, most importantly, her tiny slit was easily visible again and again from both the front and the back. With her modesty being stripped away, as well as her dignity while cleaning up after us like a proper maid, I could tell that none of my friends would take little Jessie seriously moving forward. On top of everything else, I took a lot of pleasure in how hot I looked with my perfect hair and perfect body in comparison to Jessica’s damp hair, nerdy glasses, and pathetically petite frame wrapped up in a slutty french maid costume.

For a while, I just bossed her around with the help of my friends. Not only for the fun of it, but also to get Jess used to her role moving forward. If my parents were dumb enough to label her a ‘housekeeper,’ and if Jessica was enough of a pushover to allow all of this to happen with very little protest, then I wasn’t going to relent any time soon. Instead of a babysitter, I was going to have an obedient little maid for the next six weeks.

It was a great afternoon. My girlfriends and I got to hang out and drink to our hearts’ content, and for once we didn’t have to take turns dealing with snacks and clean-up. Instead, we simply had ‘Jessie’ do everything for us. I could tell that Jess wasn’t a huge fan of her full name, but her little reactions to the alternative nickname made it clear that I had found something she liked even less. And, after making her serve us for a few hours, she voiced that she needed to use the bathroom. Better yet, she politely asked for permission after just the tiniest bit of prodding.

She was at her most vulnerable yet. Dressed up like an obedient slut, worn down from all of our orders, and needing to pee. The perfect time to strike.

“So, Jessie,” I began, enjoying the subtle twitch of distaste that always seemed to follow my new name for her. Give it time, Jess. You’ll get used to it. “You said you’re not a lesbian?”

“No!” she immediately snapped.

“You didn’t say that?” I clarified, “So you are a lesbian, then?”

“Ugh, no! I’m straight.”

Boring. But also predictable.

Just to my left, Lillian was the first to pick up on this new game I was starting. Granted, it wasn’t that new. Jess wasn’t the first girl we had grilled. There were plenty of parties where my friends and I were able to overwhelm a girl we wanted to destroy with difficult questions. And, when said questions came from all sides, it seemed more like intense group curiosity than a targeted attack. “How many times do you masturbate a day, Jessie?” Lillian asked.

Jess’s cheeks turned SO red. “W-what? That’s- that is none of your business!”

“Jessica.” Opting for the full name this time to get her attention in a different way, I flatly said, “Answer the question. If you want a break, then act like one of the girls.” Gesturing to all the bikini-clad high school graduates around me, I explained, “We do truths like this all the time.”

“But-”

“Yes, Hannah,” I said.

“Yes, Hannah . . . ” she echoed.

“Good girl. Now, how many times do you masturbate a day?”

The look on her face told me everything. There was absolutely no way to safely answer a question like that. Because she was right; it was super personal. Any number would basically be telling the whole room that she pleasures herself. Girls that were confident in themselves and their sex lives would be able to say anything and not give a shit what others thought. But it was clear that Jess wasn’t like that.

Amusingly enough, her answer was exactly what I thought it would be. Nervously glancing away, the little brunette mumbled, “Once . . . ”

Easily the tamest answer without seeming like a total prude. I actually had no idea whether or not it was the truth. Just because Jessica was a doormat didn’t necessarily mean that she didn’t take time to play with herself multiple times a day. Girls could be unpredictable like that. I didn’t have time to press about it, however, as Lillian followed up right away. “Just once? Cute. How do you do it, Jessie? Fingers, or toys?”

“Umm . . . ” One look towards me and my stern gaze was all the girl needed to comply. “Fingers.”

It was difficult to tell whether it was the questions that were causing the girl to fidget, or the need for the restroom. While it wasn’t quite the cliché bathroom dance, it was close. Since Lillian was the one interrogating Jessica at the moment, I was free to look the slutty maid up and down. The most noticeable movement was the way her hips were slowly gyrating as she adjusted her thighs and posture again and again. Then there were little things, like the way her bare toes would twitch, and how her hands couldn’t stay still.

True, it could have been the cold floor under her feet, or the fact that she was the center of attention during the uncomfortable line of questioning. But I knew better. If it was just those things, then the college girl would have pushed back harder against the barrage of inappropriate questions. No, little Jessie was trying to keep from bursting, and playing along only because it felt like the only way to get the bathroom key. If only she had managed to think outside the box–our property was pretty secluded, and sneaking outside to pee behind a bush would have probably been more comfortable than subjecting herself to all of this.

Taylor spoke up when Lillian was done asking about fingering technique, and porn preferences, and a number of other questions that made Jess stammer out the most vanilla and minimalistic answers in an attempt to save face. “What’s your favorite sex position?”

Jessica’s face went white.

In contrast, my eyes lit up. I knew it. I KNEW IT. She was a fucking virgin! If she had a real answer to the question, even something as boring as missionary, her reaction would just be awkward and hesitant like it was when it came to her masturbatory habits. Instead, there was a distinct panic in her expression and body language. The kind where she’s about to be caught in a humiliating truth in front of the worst audience possible. Worse than peers; we were girls she was supposed to be in charge of. And there was no getting away from this. Not if I had anything to say about it. “Jess.” My tone was gentle, as I gazed at her with a fun combination of pity and curiosity. I wondered if she caught that it was the first time I had used her preferred name in quite some time. “Have you never fucked a guy?” Less scary than the V word, but still with a swear in there to make the question blunt and a tad intimidating.

JESS

This was my worst nightmare.

So far, I had managed to avoid anyone finding out about my virginity. At university, I would simply lie by omission. It was easy enough to imply that I had experience in the bedroom, and it’s not like it was a total lie. I had done pretty much everything except penetration. But now Hannah was calling me out, and I was totally on the spot. I was a lot better at half-truths than flat out lying, and it sounded like she already knew the answer. But could all of her friends tell, too?

“That’s none of your business,” I meekly replied. Same attempt as before, and I could tell right away that it wasn’t going to stop the blonde from pushing the matter.

“Jessie, tell us the truth,” she said, “Or would you rather continue your chores naked? And without those pretty glasses?”

She wouldn’t! The sarcasm in regards to my glasses hardly registered, as I was too busy worrying about being stripped. While Hannah had claimed to her friends that this mortifying outfit was mine, technically it belonged to her. Which meant she could take it back if she wanted to. Plus, the urgent need to pee was still there. “Hannah, please . . . ”

My plea fell on deaf ears. “Answer the question, Jessie. Have you ever fucked a guy?”

Wincing at the crass way to describe the first I had yet to have, I blurted out the simple answer before I could stop myself. “No . . . ” I didn’t even bother explaining myself. My answers to the deeply personal questions so far had been bad enough; they didn’t need to hear about my second and third base experiences.

A few hushed whispers and giggles filled the room, but Hannah didn’t partake. Instead, she kept her gaze trained on me. “And what does that make you, Jessie?”

I knew what she wanted to hear. With a lump in my throat, I practically whispered, “A virgin.”

“What was that? Say the whole thing, girl.”

“I’m a virgin.” My lip quivered the slightest bit as I said it for the whole room to hear. Deep down, I knew it wasn’t that big of a deal that I hadn’t had sex yet. But that internal logic was impossible to listen to when this was the very first time I confessed my virginity to anyone, ever. And, of all people, it was to Hannah.

With a smirk, the blonde picked up one of the water bottles I had recently delivered the girls. Apparently they knew how to hydrate amidst day drinking. Rather than tease me about my lack of sexual experience like I expected, Hannah simply held out the water from the fridge. “You look exhausted, Jessie. Sweaty, too. Why don’t you show us those chugging skills again?”

But- but-
No way. I couldn’t drink a whole bottle! My bladder was already feeling a bit bloated and pained from waiting so long to speak up about my need to go. The last thing I needed was a drink. “Hannah-”

“Go on, Jessie. Then we’ll talk about your break, okay?”

Okay. I guess that was fine. If I was able to use the restroom immediately after downing all the water, then it wouldn’t be a problem. And, as I had already learned, arguing with Hannah was impossible. It would just drag things out and result in her getting what she wanted anyway. So, resisting the urge to sigh, I simply said, “Yes, Hannah.” Unscrewing the cap and steeling myself with a huffed exhale, I pressed the bottle to my lips and tilted it back.

The first half of the process was fine as I opened my throat and allowed the cool liquid to flow through as quickly as possible. The rest, however, made me regret the decision to do as I was told. As I drank, I felt an intense pressure on my bladder. Oh God, I had to go SO badly. Chugging more water was beyond counterintuitive, but I forced myself to keep going. Just a little more . . .

Gasping as I finished the last drop, and pressing my thighs together as tightly as possible, I was suddenly worried about my ability to walk to the bathroom without disrupting the delicate balance I had created with my posture. “There. Now, can I please have the key?”

“Hmm, what do you think, girls? Does Jessie deserve a break? Show of hands.”

Not a single hand went up in the air.

“And who thinks she should get back to work?” Hannah raised her own hand, and literally every girl followed suit. Putting on a mock pout, she said, “Sorry, Jessie. Majority rules. You’ll have to hold it. Now, how about a fresh round of drinks?”

“NO.” My voice came out a little more shrill than I had expected, but I tried not to let it discourage me. Volume was more important than tone. “Hannah, I need to use the bathroom. Like, now!” Like, desperately. “Look, just-”

“JESSIE. God, what the fuck? You’re supposed to be my housekeeper this summer. That means serving me like a mature, proper girl. Not acting like a pathetic little baby and whining about the toilet. You should have gone when you got here, or before your shower.” She stood up. Towering over me with each step forward, she demanded, “Now, are you my housekeeper? Or an immature brat? And for fuck’s sake, Jessie, stop fidgeting.”

Hannah placed her hands on my shoulders and jostled my body into a more proper stance, which was enough to cause the inevitable to happen. I had no choice but to slightly pivot one of my feet to keep from falling over completely in response to her movements, which slightly separated my thighs. It wasn’t much, yet it completely destroyed the dam I had been working so hard to maintain.

I was completely powerless to stop it. Tensing up, and gasping in horror, the floodgates opened and I began wetting myself right there in the middle of the living room.

[shmeckle]

Author's Note: Just gonna preempt the potential complaints. While there will be plenty of ENF parts to this story in Jess's future, the commission does call for wetting to be part of the story as well. As it's a bit of a hybrid genre, apologies to those who don't appreciate those story elements!

I promise not to be pissed off.

[Guru]

Such a wonderful story and wonderful casting of cfnf moments. Been waiting for the story for past 3 months and will be better if you update them frequently. Also this story kinda take me to my fav short show of cfnf about 'Nude descending the stairs " .

[*Lady Lucia*]

I can only update it so much! This is a Patreon commission, which means only one story part per month with potential feedback/suggestions/ideas given to me in between.

--Lady Lucia