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Chapter 12 by Nicegent42
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Chapter 12
Cal swung open the door to Clara’s newly assigned locker, while his mind let out the hundred curses his mouth couldn’t yet betray. ‘Fucking shit insane idea, undercover boss my ass…’ he thought, the stream of profanity only continuing. The new garment he was laying eyes on for the first time brought those internal rantings to a grinding halt. He touched the dress, feeling its fabric. The dress itself wasn’t anything special, but the sight of it caused his mind to lean a specific way, bringing thoughts of the last girl he had fucked wearing the same uniform in the very same hotel, not long ago.
Stripping out of the blue wrap dress, something he would love to see his Moriah wear, yet it was on him, a man in women’s garb pretending he was someone else. Knowing what he looked like, standing there in high heels and suggestive undergarments, a slight blush tinted his cheeks. He touched the offensive yet enthralling garment once more. Every time he’d undressed since the drastic change to his body, he couldn’t take his eyes off the naked form that still felt like it belonged to somebody else.
Years prior, back when they were opening the hotel, a lot of deep discussions took place about the aesthetic of the environment, and a huge part of that would be the staff uniforms. They were to be the walking talking representation of the enterprise after all - the people the guests would see more than anybody. Moriah wanted something simple, and tasteful for the custodial staff. Uniform pants, and a matching button-down could portray a dignified, unified workforce, there to serve the customer’s needs, but attired in such a way to not inhibit their ability to move around while performing the difficult task of taking a usually destroyed hotel room, and turning it into a pristine, welcoming abode, one where the guests couldn’t possibly conceive of the disgusting horrors that must have taken place in every room at least once before.
Calvin obviously had other thoughts on the idea. In his mind, the perfect uniform for the maids would have been something similar to the little number he bought for his conquests, the one Moriah had been keeping him in lately while she rode his face. Even he knew that would be a step too far though, so he decided to split the difference, and pitch the simple black linen dresses. “They show that we have a timeless professionalism here… that we won’t forget the little touches that a lot of our larger competitors have.”
Of course Moriah knew that was bullshit, but she was trying to pick her battles at the time, and compared to some of the ideas she knew were swirling around in her then husband’s head, it was rather tame. The idea that currently swirling through his head was the thought of his slightly older wife on all fours, while he had his way with her.
Slipping into the shirtwaist garment, Cal blew out some air from his puffed out cheeks, forcing a positive spin to what he was putting on. ‘Least I don’t have to worry about any unwanted erections in this thing, when I walk past a mirror. The dress can hardly be considered sexy after all… matronly, sure.’
His mind strayed away, as the deep breath caused his ample chest to rise and fall. The feeling of the breasts he shouldn’t have gave him visions of a certain particularly busty immigrant woman, one of his many encounters with the hotel maids, and how he felt when the bodice came unfastened, and her breasts spilled out when he ravaged them.
Buttoning each of the white pearlescent buttons, all the way to the open collar at the top, covered his cleavage, and prominent assets in a way he’d been dreaming of for days. Modesty, it was a welcome change. Without the apron, the thing could almost pass as something simple, casual even, but the white piping around the short sleeves made sure that everybody knew this garment was something else entirely. Even the three-inch pumps that just barely squeezed in under the uniform code were a welcome change compared to skyscrapers he’d been strapped in for a few days. Though it was a relief, truly the dungeon master had only come by and loosened the **** rack by only a few turns. ‘What’s wrong with me… fucking cursed perspective…’
After slipping the simple white waist apron into place, and pining on the little gold plated nametag that proudly displayed the name Clara, a name he loathed more by the minute, he approached the mirror, this time speaking out loud.
“See, nothing sexy about it.” Calvin’s eyes slid across the girl’s body he was seeing in the mirror. Her heeled feet making her smooth legs look long, the uniform dress covering her tight body, her large breasts and… His tightening panties disagreed with his own statement even as he forcefully pulled his gaze away from the reflective surface, all while fastening the name tag felt like locking his own shackles.
Though he didn’t feel like he had much choice in the matter, the other maid’s dress, as fetishistic as it was, was something a person wore of their own accord. They wore it to feel pretty, to feel erotic, to feel powerful in a way, even. Even as something he wished to see others in, it was because of the beauty it would add to their already glorious form, and those women chose to wear it themselves for their reward. His current ensemble couldn’t quite be spoken of with the same reverence. It was a garment that came with a waged position, and one that didn’t pay that much. It was something to denote your lower standing to the others around you. It was a mark of shame. The fact that it was still causing a stirring in his loins just the same, Calvin couldn’t deal with it. All he could do was stuff that into the pit of his stomach along with everything else, and hope his digestive fluids would take care of it.
“Nope… nothing sexy about it at all.” he repeated in the flowing feminine voice he had practiced, the little mantra he had not just repeated, but recorded running through his mind. ‘I believe in manicures, I believe in overdressing, I believe in pink, I believe in primping at leisure, and I believe in wearing lipstick. I believe that laughing is the best calorie burner aside from kissing, and I do believe in kissing, I believe in kissing, a lot. I believe in being strong when everything else seems to be going wrong. I believe the happiest girls are the prettiest girls. I believe tomorrow is another day, and it’s a wonderful day for me to be a happy, pretty girl.’
The mantra didn't help settle his nerves but to pull this off he needed to be Clara and the words reinforced who she was… who he was until the ordeal was over and behind him.
“Clara, do you need any help!?” Bethany shouted through the doorway, after checking her watch. “I can be of assistance if it’s required!” she offered, counting the seconds.
“I’m coming!” Cal shouted back. “Just locking the rest of my things away now.” The last thing he wanted was the middle-aged beauty pawing around his body. His thing wasn’t to be trusted at the moment.
Turning to the door, Calvin’s puffy lipstick covered lips shifted into something closer to a snarl as his employee offered to come assist. He knew it wasn’t a real offer, just her way of saying he was taking too long. Something he had used to give a slow worker a hint, and now it was being used on him by someone beneath him. Still, at the moment he couldn’t do anything about it so after that, Cal had to follow Bethany for a short walk to the elevator. It felt like the longest walk of his life, his heels clicking with each step, knowing he shouldn't own the pair, let alone walk so well in them.
Every face passed was a familiar one, and most probably didn’t have a kind word to say about their formerly looming overlord. What they saw was another demure little immigrant girl, nervous about her first day on the job, as she fell in line behind the second most ruthless taskmaster in the company’s employ. While Cal delusionally clung to the none held that first notion, even if not, the second would still have felt far more upsetting. People not liking him was one thing, but people pitying him was something he could hardly tolerate.
As the elevator door opened, that familiar chime sounding, Calvin, and Bethany stepped out onto the fifth floor of the hotel, where a young woman, her skin a strikingly similar shade to Cal’s, was waiting with a cart full of bleach, rags, and what-have-you, in front of an open room.
“Clara, this is Ana. She’s one of our trainers, so you’ll be shadowing her today. Stick with her through lunch, and I’ll be back to collect you some time this afternoon.” After introducing the maids, Bethany looked at her watch before stepping back onto the elevator, leaving Cal to size up the girl.
He’d seen Ana around before. She’d been working at the hotel for the previous six months, and in that time had managed to find her way into a training position. The girl had a measure of seniority, as high as the turnover rate was for the department. While employee retention at the Ahuva Bahyeet was higher on average than most similar hotels, for reasons Cal couldn’t understand, the maids seemed to leave almost as quickly as they arrived. Everyone else in management understood perfectly why. All in all it felt insulting that he needed to be trained to clean. Many of the girls were just far too lazy for his liking, but so long as they looked how he desired, he felt it was the right atmosphere for his hotel.
The owner in disguise had thought about bedding the girl a few times, but for a little while, there was always some prettier, younger thing to grab his attention. After that, he decided to keep his hands out of the cookie jar at work, at least for a little while until things got back to normal between him and his love, not that he had been great at sticking to his self imposed restriction. It wasn’t even that Ana was anything to snub either. She just carried herself in a way that let Cal know she wouldn’t be an easy conquest, and his desire to stick to the path of least resistance won out.
“Hola, Chica! Bienvenido al infierno!” Ana threw her arms around the new girl's neck, and pulled her in for a tight welcome hug, nearly **** the life out of her.
Cal found himself giving her a ginger pat on the back, not wanting to incentivise the behavior, but also wanting to be able to breathe again. It didn’t help that the image of two sexy maids having their way with each other before inviting him to join them in bed filled his thoughts. Once he broke free, he finally managed to speak. “I’m sorry, but I don’t speak Spanish.” all while he bit his tongue, the ideas of American exceptionalism blaring like an alarm in his brain. ‘We speak English here in America… Chica.’
“You’re kidding me?” The senior maid wore a genuine expression of shock. “What are you, like one of those dreamers who came here as a baby… or were you born here? It’s a shame, Latinas like us are losing our culture, little by little. You’ve just inspired me to teach you, Cariño. As long as you can last here, I’ll make sure you learn a little bit more about where you come from… Where do you come from actually?”
“Me…” Cal was genuinely shocked that the woman could mistake him for anything other than what he actually was. Sal’s friend at the DMV was one thing, but this was an actual hispanic girl looking at him, and just assuming. “I’m white actually… Mediterranean of sorts, I guess. My mom’s family has been here so long, they stopped keeping track, and my father’s parents were Greek immigrants.”
For a moment Calvin wondered if he should have given such an honest answer. There was a story for Clara, but not one he wanted to claim as his own, though none of the help would have any reason to know about his background so he breathed easy. What he didn’t account for was Ana not believing a word he said.
“Okay, whatever you say. Dreamer it is… You must not have your card yet. They’ll help you out with that here. It’s like one of the few things they’re actually good about. Now, a pay raise… good luck. You might want to try a different background for your dad though, if you wanna stay under the radar. Bent isn’t a very Greek name… It’s not a very Latin name either, now that I think about it, so good move there, I guess. I know getting some new documents with a better option isn’t easy or cheap, so you’re probably stuck with it for now. Honestly though, it sounds kind of sexy, you know?” Ana wondered what the girl’s real last name was.
The beleaguered hotelier opened his mouth, but no words came out. His first impulse was to argue, and set the mouthy employee straight, making it very clear who he was, and where he came from, but the humiliation of outing himself won out. After that, he couldn’t find any other argument with which to dispute her, so he just grit his teeth and blushed, while the woman continued unfettered.
“For now, you can call me Profesora. I like the sound of that. Come along, Flaca. We’ve got a lot to do, and I want to eat my lunch on time today. Flaca means skinny girl, by the way… though you’ve got some meat on your bones where it needs to be, don’t you?”
After entering the room, toting the cart behind them, Ana closed the door and locked it. Apparently what it took for Calvin to be pulled from his stunned silence was for his trainer to begin unbuttoning the buttons of her dress, just above her apron.
“What the hell are you doing?”
While he still desired to have his way with the girl, doing it with the current state of his body wasn’t quite what he had in mind. His mind was put at ease, when she retrieved her smartphone from the waistband of her white cotton undies. “Just getting us some music to listen to, while we clean.”
“I thought there was a rule against having your phone on your person while you’re on the clock.”
“Silly girl,” Ana smirked, “are you reading that, out of the rulebook. It’s fine. That’s just one of those rules that they make so they can feel like they had anything, at all, to do with the hotel getting cleaned properly, and justify paying themselves in a week what we make in a year. So long as you do your job well, nobody is going to come check up on you. They’ll only check behind you if you start getting guest complaints. Just clean like you’re supposed to, and you’ll be fine. Besides, I don’t get paid enough to follow that rule. If they try to take my music away, they’re just going to have to fire me. The only exception is Miss Long, Bethany, she sometimes tries to crawl up someone's ass, but she isn't that bad so long as you do your job… I mean actually do it.” Ana rolled her eyes showed Cal how much she believed in the idea of hard work to earn an honest day's wage.
It was in fact a rule made by management, one Calvin Bennet actually. It was agonizing for the man to bite his tongue, but he couldn’t reveal his identity. Instead he just decided to say something to Bethany before he left, and let her deal with the insubordination. While Reggaeton began to play out of the tiny speaker, the only consolation Cal could find was that Ana immediately set to work, scrubbing a spot out of the carpet with a little hand brush, letting him get an excellent view of his trainer’s amazing ass.
“Don’t just stand there holding that mop, Clara.” the woman playfully chastised to the person gawking like a fool behind her. “You gotta use it. Get around the window ledges, and the curtain rods. After that, I’ll check behind you later, but you can go ahead and get started in the bathroom. If you have any questions, I’m right here. We always vacuum last, so just sweep everything onto the floor.”
For the next half hour, Cal scrubbed the toilet and sink, sprayed out the shower, polished the furniture, changed the sheets, and emptied the trash, while Ana continued to deal with the stubborn stain on the carpet. The new maid began to feel an air of superiority having completed more tasks, so therefore more work, but Ana was diligent, and the wine in the carpet was relentless.
There was one upside of having to suffer through a bunch of unfamiliar songs, save a couple of top forty hits, and one country radio tune. While there was some Mexican folk music on the playlist, the bulk of it was reggaeton. Originally a Caribbean thing, it was still quite popular in Mexico, the country even producing a few stars of the genre on their own. With thumping drums, and baselines, it was the perfect music for Ana to bounce the tush she was sticking up in the air to, as she hummed along to herself, still scrubbing the floor with all her might. The free show almost made it all worth it to Cal, but then he’d get a shooting pain in his foot, and rethink the idea.
After dropping some powdered absorbent on the saturated patch of carpet, Ana supervised Cal running the vacuum, while she danced around the room to her music. With the whirring in the air, he was beginning to get a sense of a job well done. He’d put in his day's work, and he should be proud. That’s what he told himself, just before Ana interrupted his self-congratulations. “Okay, one down,forever to go.”
Looking at the little clock on the nightstand, Cal suddenly realized that the hours of labor he’d been breaking his back doing all took place in the span of about an episode of television. “How many more rooms do we have?”
“The whole floor… at least the ones that aren’t occupied, and some of those we still have to empty the trash, swap the towels, take out the trash, and make the bed… unless they have a do not disturb sign. Fingers crossed.”
As cheerful as the moment she arrived, Ana loaded the cart back up, and moved onto the next one, while the newest maid stood frozen, trying to calculate just how much work the day was actually going to be. If he hated the maid’s dress for the things it was making him feel, he hated it even more for how hard the thing was to work it. His knees felt rough from the carpet, every time he had to get under a piece of furniture to pick something up, not to mention just how difficult it was to not let Ana know what color his panties were. The way she moved about effortlessly had the undercover boss wondering if she used to be a dancer.
This cycle continued room after room. If it was a routine cleaning for a guest, they tried to be in and out as fast as possible, but after checkout, they’d scrub and scrub until the room was so clean, the idea of anyone having ever occupied it before seemed completely absurd. The hotel held itself to the highest standard after all.
When it was Cal’s turn to scrub a stain out of the carpet, he quickly realized that the girl wasn’t giving herself the easy task. Chemicals, and brush work, and more chemicals, and using muscles in a way he hadn’t in years proved quite difficult. Even worse, after taking the time to appreciate Ana, he was very aware that his ass was now the one proudly displayed in the air. Another reminder came when Ana gave it a playful swat as she walked by, before saying, “Good job, Clara. Way to get that done.”
After a few hours, and keeping himself distracted by the tasks, Cal began to relax, almost forgetting what he was wearing, at least until he’d swing around too fast, and feel the tug on his chest. Still, mopping out a bathroom, the Reggaeton thumping out behind him, it was almost zenlike for the emotionally exhausted entrepreneur. Without realizing it, he began swinging his hips along to the music, as he worked his way back out of the bathroom.
“Damn, show me what you got, chica!”
At the sound of Ana’s voice, Calvin realized what he was doing, froze, dropped the mop, and then stood straight upright. “I don’t know what you’re talking about.”
“I saw you shaking that perfect caboose I’m not at all jealous of. You got some moves, girl! Dance a little more while I plot my **** on you for being the perfect woman.”
“I can’t dance!” Calvin shot back defensively, as though she’d just hurled the worst possible accusation she could think of at him. The phrase “perfect woman” felt like a knife had somehow stabbed his pride. ‘No! I’m a man…’ his internal voice started out strong becoming more of a whimper.
The senior maid just smirked. “Of course you can. I just saw you, plain as day. Are you the type who gets insecure when she thinks people are watching? Were you, like, ugly in high school or something? C’mon, let’s dance.”
Ana slipped an arm around Cal’s waist, and pulled him in so close, they were almost straddling each other’s legs. As her hips began to gyrate with the music, he found himself almost compelled to follow along, as he breathed in her floral perfume. The girl was definitely hot. That was something he couldn’t get out of his mind, but he was beginning to see she was also fun.
As he caught a glimpse of the two of them in the mirror, his mind drifted back to two college girls doing much the same thing, on a night out. The way they beckoned him closer with the wag of a finger stuck in his mind for years to come. As he gazed at his reflection, the idea of Ana and Clara doing the same popped in his head, and the inevitable three-way that followed would have been spectacular. The only problem was that Cal quickly realized that the girl in the mirror was him, and once again he was extremely turned on by the prospect of fucking himself. All he could do was be grateful that the panties he’d chosen for the day had absolutely no give.
That’s when the senior maid dropped another bomb. “So… he’s out of town now, but when Mr. Bennet gets back, you might want to watch out for him. A pretty girl like you is right up his alley, and he’s not exactly the safest person to be alone with. I don’t know how much of a consolation it is, but if he does try anything, you’ll at least get a good payday out of it, when you go to HR to sign sign one of those things. They’ll send you on your way after that, but that also puts an end to them helping with a green card, so keep that in mind. That’s probably how I got this training gig already… everybody quit… not that the money has been worth it… but just… be careful with him, okay? You’re a delicate flower, I can tell. Maybe we’ll get lucky, and he’ll never come back.”
Cal wanted to speak up. He wanted to tell the girl that she had him all wrong. He believed he’d never **** himself on anybody, though the concept of power dynamics, and privilege were not things he actually understood in a meaningful way. While he couldn’t quite put his finger on why, the last thing he wanted was his new friend thinking of him that way, but he couldn’t very well correct her without giving up the game. All he could do was **** a smile, and nod in agreement, while he bit his tongue. He decided to just prove to her he wasn’t that guy. That would have to wait until after things went back to normal, perhaps over a nice dinner, and whatever came after. Whatever the case, he knew Ana was certainly too good for a quick tryst in an empty guest room.
When lunch finally arrived, the pair found themselves standing in line at the employee meal service area, essentially a cafeteria where they could purchase premade items, and even some of the same dishes as the guests, though out of their sight of course. Ana snatched a wrapped hoagie from the line, as they passed, while Cal eyed the food that he knew to be sub par, but also looked like the most delicious thing he’d ever seen. He’d been wearing the corset non-stop for two days. While the rumbling never ceased, the few scraps he’d had in that time filled him up quickly, just long enough for him to get comfortable before his stomach started shouting at him again.
Worse still, the junior maid had been working up a little sweat, and his head was beginning to itch fiercely. The weave stopped him from being able to scratch it though, so all he could do was swat the side of his head to dull the sensation, and hope nobody thought he was completely insane. At the very least it distracted him a little from the screaming of his feet, his toes crushed into the toes of the shoes, after hours standing.
When he got to the front of the line, an older woman was waiting by a register, and a drink machine. Ana checked out first, getting a soda as well. When Cal approached the register, he forlornly said, “Water.” before following behind Ana, who was now wearing the first sad expression the feminized man had seen on her face. When they took a seat at the picnic table in the employee break area outside, the first thing Cal did was kick off those heels, and start massaging his feet, while Ana slid half her sandwich across the table.
“Do you not have any money?” she asked out of concern.
Unsure how to handle the genuine show of care from another person, Cal nodded his thanks, while he cursed under his breath, as he thought about the flush bank account under his name that he just couldn’t access. He still hadn’t spoken to Sid, but the man was supposed to come over that night to remove his corset so he could talk about the funds with him then. The mental math, after how much that cappuccino machine actually cost sunk in. The skirted man quickly realized he’d probably prefer dinner free of the corset over a sparse lunch, so the **** decision was made to delay his gratification.
“Yeah, just broke till I get paid.” It wasn’t quite a lie. Whatever the case, he didn’t think of much more of an excuse than that, and hopefully Ana wouldn’t press any further. He’d very quickly learn that of course she would.
“What about Mr. Larson? Aren’t you two dating? Can he give you some money?”
“Sid is not my boyfriend!” Calvin replied, completely horrified by the idea.
“Okay, okay.” The young woman smirked, clearly not believing a word. “It’s just, I heard that he got you this job, and you didn’t even have to interview. What’s your connection, then? That’s an awfully casual use of his name, cariño… for someone who protests so much anyway.”
“He’s just a… friend…” Cal struggled to come up with any other word for the man that wouldn’t betray the quiet loathing he carried, but fell short. Unfortunately, to Ana, it just looked like the new girl just wasn’t quite ready to call her fuckbuddy her boyfriend yet.
“Okay then… Well, if you’re single, we should go out clubbing soon. Don’t give me that I can’t dance nonsense. That excuse will never work on me again. Sorry to say, you’ve ruined it.”
Cal thought about a night out with the girl, her on his arm, as they hit the club and danced the night away, before a more intimate activity as they greeted the sunrise. “Yeah, that sounds like fun.” he agreed, not really realizing just what he was agreeing to.
The free spirit Cal was fast becoming acquainted with found her eyes drawn to the new girl's feet, as she watched her massage them tenderly. “Why do you wear those heels, by the way? I have to ask. They can’t be comfortable.”
“Because they’re the only ones in my closet.” Cal answered honestly.
‘What a fashion hound this one is.’ Ana thought. ‘I’ll have to get her to take me out shopping sometime. I bet she’s better at makeup than me. Maybe I can get her to give me a makeover before a hot date sometime. She definitely feels like new best friend material, that’s for sure.’ She smiled, and offered a simple compliment. “Well, they look nice.”
After the short half-hour meal break, the new friends, as Ana was already thinking of them, returned to their duties, where they continued toiling away at cleaning the floor. For Cal, time might have slowed to an actual crawl if not for the friendly maid trying her best to squeeze as much fun as possible into something that most definitely wasn’t. Between the music, and the constant impromptu Spanish lessons over every single new noun they came across, the man in the painful shoes hardly noticed four o’clock had snuck up on them.
The trainer was very pleased, and quick to dish out praise. “Good job today, cariño. You pick up quick… probably cause you heard it a lot growing up, I bet, but you seem like a smart girl. I like everybody here, but it’ll be nice to have someone around that I feel like I can have a good conversation with. ¿Hasta mañana, mi amigo? We didn’t scare you off?”
“No, I’ll be here.” Cal answered, not thrilled with the prospect, but at least that day wasn’t a total disaster. ‘Perhaps tomorrow I’ll get a chance to take a peek in the offices.’ he thought before replying, “Thank you, Ana… I’ve been having a rough couple days, and it’s just nice to have someone be… nice. Thank you.”
Staring at her perfect ass while she danced around while they cleaned also didn’t hurt.
“No, no. Espaniol, seniorita.” the trainer playful chastised.
“Lo siento.” Cal replied, smiling, but rolling his eyes. “Gracias.”
“De nada.” Just then, Cal was even more confused when the girl threw her arms around him, and pulled him in for a familiar embrace, as though the two had known each other for a lifetime already. “Anyway, Miss Bethany wants you to do a simple room by yourself before we leave, so she can, like, assess your progress, or whatever. She’s really particular… but not ridiculous, like that Mr Bennet. Just do a good job. I’m gonna hit one more room for the day, and then I’ll wait for you in the changing room. We can drop off the laundry cart on the way out. Meet Miss Bethany in the room at the end of the hall. She set it aside, special for you. Just remember, don’t tell her about our little dance party. She’s nice enough… but not that nice.”
After entering the room, Bethany stood waiting in a space that didn’t seem that disheveled compared to what they’d been working with all day. Only the bed appeared in disarray, and Cal had to assume it was one of the facility's rare overnight guests who disappeared first thing in the morning.
“Good afternoon, Clara.” Bethany greeted. “I’ve been told you did well today.”
“Oh, umm… yes, ma’am. Thank you.” Cal pointed his eyes to the floor, with his hands clasped in front of him. It wasn’t intentional, or for the act even. Without realizing it, Cal was flashing back to a time when his mother would appraise his efforts to clean his room with the same kind of cold detachment, all while it felt so wrong to speak to her, his employee, like she was superior to him.
“Let’s call this your first test. I’m going to step outside, and set a timer for ten minutes. That’s the amount of time it should take one of you girls to turn over a room like this. Sounds reasonable, yes?”
“Yes, ma’am.” Cal nodded. It was him that set that standard after all. How could he disagree?
“Alright then. I’ll leave you to it. Hurry now.” And with that Bethany stepped out the door, closing it behind her.
‘I’ve totally got this.’ Cal thought. ‘How much easier could this get… and it’ll be the perfect opportunity to show those maids that my expectations aren’t unreasonable at all.’
This went on for a moment, until the feminized man suddenly realized that he'd already wasted two minutes patting himself on the back. From there he tried to hurry. All the room needed was dusting, vacuuming, and a sanitized bathroom. Nothing too difficult. What he didn’t realize was without the music in the background fueling his efforts, it was quite easy for his mind to wander.
As he wiped down the surfaces, his thoughts drifted to Moriah, alone in that big house. He wondered if she missed him. He definitely missed her. As he cleaned the glass in the bathroom, he thought about Sid and his friend talking about him at the DMV like he was a bimbo piece of meat, and he had to fight the urge not to break the mirror. By the time he was vacuuming, Cal realized that all he’d done that day was clean rooms - that he was no closer to his goal, and he still had yet to see the object of his ire to arrange access to his bank account.
Calvin was tying off the garbage bag when Bethany returned. “You didn’t finish in time, Miss Bent. That won’t do at all.”
“But, I literally just have to throw this on the cart.” Cal tried to defend himself, but the operations manager remained unimpressed. Silently, she slipped on a white glove, and ran a finger across the dresser. She formed a stern expression, then held it up to show just a hint of dust and lint remained. “Oh… I…”
The exhausted man didn’t have a reply, at least not one the severe woman would have accepted. It infuriated him though that there was a hundred times more grime on his apron than what he was being silently chastised for, but conveniently forgot that should he have found the same situation, he wouldn’t have been anywhere near as kind.
“This is unacceptable, Clara… Was the training not adequate? Did she not go over this with you?” Bethany asked, suspecting the problem was not with Ana.
Cal thought back to that morning when he decided to report the girl for using her phone on the clock, but in the time since, Ana had been the only person who he felt like gave half a shit about him in days. Not only that, but she did go over all the rules and policies. The music might have even been helpful if he was being honest. That might be a policy worth revisiting when he was back in a position of power, he considered before his original concerns of the staff openly listening to something that would upset those that actually mattered, the guests. Though every impulse at his disposal was screaming at him to throw her under the bus, for a reason even he couldn’t make sense of, Cal threw himself on the sword instead.
“No, she was fine. I’m just very tired, I guess. I haven’t been on my feet this long in a while, and I didn’t eat much lunch today. I’m very sorry. I’ll do better tomorrow, I promise.” The lunch comment was true. He could hardly take more than a few bites of the half a sandwich before the corset put a stop to him enjoying the worst sandwich he’d had in as long as he could remember. Cal wasn’t sure if that was a blessing or a curse.
“Alright then, I appreciate your honesty. I’m a believer in working towards improvement, and if that’s what I see then we won’t have any issues. Tomorrow will be better, and so on, or I don’t care who your boyfriend is, you won’t be employed here much longer. Do we understand each other?”
“He’s…” Cal started to argue, but he truly was exhausted, and he’d run out of steam trying to convince anybody that Sid was anything but a romantic interest. Instead he bit his tongue, stood up straight, and politely nodded, hoping that it would be the last thing he had to do that day. “Yes, ma’am.”
Bethany shocked Cal then, more than ever before. He’d seen the woman smirk. He’d seen her sneer. What he’d never seen Miss Long do before was offer a kind smile, and words of encouragement. “See, you’re already showing improvement. You didn’t argue. That’s the right way to handle it. I don’t like the way Sid went about getting you this job, but I’m not going to hold that against you. Just be a good girl, do as you’re told, and I’ll be here if you need anything at all. My door is always open.”
Down in the changing area, Ana threw a bundle of black and white cloth into a nearby laundry basket before replacing her nametag in her locker, while the new Clara struggled to unbutton the bodice of their dress. “Just rip that shit off, girl.” the trainer said, walking over, and just doing it herself. “They’ll wash and press those things before we get them back, so you don’t have to be delicate. Just show up tomorrow, and a clean one should be in your locker. Just tear it if you have to, and get that sexy body dressed. I’m not trying to miss the bus.”
Cal should have felt humiliated, being a grown man getting undressed like a child, but in the years since they’d opened, he’d never wanted to leave the hotel more. He just let Ana slide the garment over his head, careful to avoid messing up his hair, and then cast it into the cloth bin. Quickly, he dressed in the blue dress and heels he’d arrived in that morning, and followed his new friend along to the time clock, while she carried a bag of cloth over her shoulder like Santa Clause.
“Technically, we’re supposed to drop this off with laundry before we clock out, but it’s on the way, and they can have the extra two minutes for the ten it saves me in backtracking. Come on, I’ll give you the dime tour on the way out.”
‘Another tour.’ Cal grumbled to himself. ‘Like, I really need one of those.’
As Cal praised himself for knowing the hotel like the back of his hand, when Ana swung open the door to the maintenance halls hidden away from the guests, he realized he hadn’t been back there since the building was being constructed. The laundry room was the first door on the right, where the bag got tossed in a cart, along with Ana giving a little finger wave, and a “Hello, Rosa. You’re looking lovely today.” While the old woman waved the girl off, she was smiling brightly. Ana had that kind of energy after all.
Continuing down the corridor, they came up on the back side of the kitchen, where it bumped up into the loading docks. People were abuzz as they wove through each other like a well-oiled machine, occasionally the shout of “Corner!” filling the air. Weaved into all this, people were talking, and cheering. That’s when Cal noticed some people exchanging packages over in the corner.
“Are they selling… ****?” the disguised manager asked, shocked such a thing could be happening right under his nose.
“What… Girl, you’re silly.” Ana chuckled, as she shot back a decidedly unserious smirk. “It’s just the community helping each other. Like, Maria fixes people’s clothes, and Hector will take a look at your car if it breaks down. Jake, the pastry chef, will bake you a lovely cake if you’ve got a birthday party, or something coming up. We all look out for each other here… Don’t worry, we’re gonna look out for you too. Now, through here is the back exit. Technically we’re not supposed to go out this way, but only the kitchen guys will see us, and none of them are gonna say anything. It saves the ten minute walk around the block to get to the bus stop. Maybe, just maybe we might actually make it before we have to watch it drive off without us while we wait an hour for the next one.”
Stepping through the security door with the alarm disengaged, Cal found himself in an alley that he didn’t even realize ran up into the building. Off to one side, a guy in an apron squatted down, and to the other, a young bespectacled woman, no older than thirty Cal assumed, was smoking a cigarette as she leaned against the wall.
“Lauren!” Ana squealed, as she rushed over and gave the woman a big hug. “I haven’t seen you in forever, girl. How are you? Where have you been?”
“I’m good!” Lauren replied, returning the gesture. “I moved to nights because I got a new day job. Had to make stuff work, you know… since… well… Anyway, gotta sneak in a smoke when I can. I really should quit... It’s so good to see you, though. Taking the bus today?”
“Yeah, my brother has the car. Anyway, this is Clara. She’s very cool. I’d introduce you better, but we gotta hurry. Don’t want to be late.”
“I get it. Hurry up, girl. We can catch up later.”
As the brunette in the front desk uniform smiled and waved goodbye, Ana and Cal continued to walk at pace. Wearing the white heels he arrived in that morning, after being on his feet all day, was its own type of ****.
The senior maid continued to fill in the blanks. “She’s great. My favorite guest-facing girl actually. Most of them can be a little hoity-toity. Had some trouble with the husband, and he’s out of the picture now, but she’s got the cutest little boy at home, Emmanuel. Looks just like his mother… Honestly, he’s too pretty to be a boy. I wonder if she’s going to keep the name Brooks.”
Cal tried not to think too hard about the phrase, “Too pretty to be a boy.” Instead he began to ponder ways to seal all the cracks that he’d just been shown. He also wondered how anybody on that undercover boss show didn’t just immediately break character, and announce themselves the second somebody did something similar, but he was doing the same. The alternative, revealing who was under all the makeup and breasts, was just too horrifying to even consider.
As they crossed the street out of the alley, they seemed to have the gods of timing’s favor. They made it to the open swinging doors just in time to follow a little old lady, and watch her fumble her cash at the slot.
The ride back into town was far more pleasant than the morning. Ana’s glares at any of the staring men proved to be far more effective than Cal’s. She had to head all the way to the depot to transfer, so he wouldn’t be burdened by a lonely trip. The girl even offered to drive him back to his apartment on days she had the car. Overall the day was a win, not exactly a win-win scenario but he would take it, even though he felt no closer to his actual goal. All he had left to do was go back to the creaking little abode, and wait patiently for Sid to arrive. The man got off not much later usually, so it wouldn’t have to be long.
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Maid Undercover
Chapter 1
Calvin Bennent owns 49% of a high end hotel called Ahuva Bahyeet - Beloved House It is doing so well that Mega Corp is interested in buying it out, the problem is the company is missing money and they aren't able to find out who is stealing from them. In order to fix this for the deal to move forward Calvin goes undercover as a maid, but this isn't done willingly.
Updated on Jun 21, 2026
by Nicegent42
Created on Feb 3, 2024
by Nicegent42
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- 15 Chapters
- 14 Chapters Deep
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