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Chapter 14 by Nicegent42
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Chapter 14
There he was, standing in a hotel room that a guest had just vacated, the bed had been stripped, the sheets and comforter replaced with something not soiled by sex but there was a lot more work to do. Music played gently from the tv from one of the smart devices apps. It wasn’t some Spanish pop or rock like he had been **** to listen to. Looking at the mess, it seemed daunting swaying his hips to the beat he got to work. That was when someone came in the room or had already been in the room watching it was like things just changed yet it had always been, it made sense in the same way things did in the moment in a dream. The thing was, it was wrong, wrong enough to jar Calvin’s sleeping mind to break the **** flow of the dream. The man in the room with him was one of the hotel owners, himself. Standing there in one of his favorite suits, a charcoal gray tailored number with a metallic blue tie that had been a gift from Moriah on his birthday back when they first started to date and Calvin was looking him over like a predator might do to its prey.
Here he was in an outfit that was definitely not the hotel’s uniform. The short skirt of the French maid costume exposed his smooth legs that ended with his feet perched in a pair of overly tall glossy black heels. “Sir, I'm working” Calvin heard himself say in a soft breathy voice that sounded almost flirty. He had just talked to himself, it was wrong, so much was wrong.
“Just admiring the view, you know Clara, you are beautiful.”
That was when Calvin felt the hand, his own hands or the hands of his non feminized self wrap around him from behind Grasping and massaging his breasts, tits that seemed slightly larger than they should, not that he should have them at all. The hands began massaging as lips found his neck. It was a burst of sudden pleasure that had his red lips opening slowly like he was going to call out, but no words escaped. It was so intense his knees buckled casing him to fall forward, the hands could have held him place, but instead they let him fall to crash on the mattress. The bed now for some reason has a light dusting of rose petals across the surface.
“I see why you started with the bed you little minx!” Calvin heard his voice, his normal real voice that sounded so vastly different from what would come out of his own mouth right now if he could speak. Face down on the mattress, ass up he felt those hands under his skirt massaging his ass before pulling down his panties.
“I saw you shaking your ass for me and now it's going to be mine!
“No! Nooooooo! The yell wasn’t out loud it was in his mind, his own voice yet what came out as he moved his puffy lips was vastly different. “Yes, yes please!” Clara’s voice said, purring happily.
That was when Cal sat bolt upright in bed, not his real mattress, not the hotel room’s but back on the small thing bought for him in the small apartment. “It was a dream…” He said, trying to clear his voice and say it again to just hear himself use his true voice, not that of Clara, but even after two attempts it didn’t sound right. It was close but more like the sound of someone trying to sound like Calvin David Bennant. The worse thing about the insane dream was he woke up with a raging hard on. “Huh… I should have finished last night.” White he sad that, he left his noticeable arousal alone, swinging his feet of the bed almost putting them on the floor before slipping them into the white heels. “Another day… I need to find the fucking stealing from my hotel and then find a therapist to work through this trauma.”
Not at all happy with how he woke up or what he woke up to, Cal began getting ready for another day. The corset still on, meant no shower again so he gave himself a sponge bath. Then began his new routine to look his best, an experience he disliked, but it was to get his character in order. “Clara Diane Bent, I’m Clara Diane Bent” He repeated a few times in the mirror, seeing his… Her reflection, pointing to her face that had a growing smile, **** more and more to try to look more natural.’Just a character, I live in California. Not Hollywood but I should win a fuckint Oscar for this. I will just have to settle for millions in my bank account from Mega Corp.
Stepping into his hotel his brown faux leather pointed toe four inch heels clicking on the floor with each step. The wrap dress from yesterday was so much easier to slip on than what he chose for today. A skirt that went with the shoe he assumed was brown and faux leather, though not exactly the same shade as the heels, a bit lighter but they were similar. A cream colored blouse that had the top half lace along with its three quarter sleeves and of course Clara always had jewelry. Not wanting to wear the feminine jewelry like this, he missed opening the drawer in his closet back at home where he kept his watch collection. His collection of expensive watches and the cheap old pocket watch he had been given as a graduation gift back so long ago when he graduated high school, it was a reminder to good times, unlike the things he put on now. ‘Thank god for my bank account… my real one, Clara could afford expensive things, so… small miracles I didn’t have to shell out the cash for anything real.’. He thought, feeling the few thin gold bangles on his left wrist shift as he walked and back, the large gold hoop earrings, the weight already feeling more normal than he liked after only a few days of them hanging from his ears. "Time to start my… err Clara;s miserable work day, smile, smile, girls like her smile…’ he told himself putting one heeled foot in front of the other and his hips rocked with the feminine gait.
The hotel didn’t have a large security team, but seeing one of them standing by the front desk talking to the receptionist. Calvin kept the smile in place, but squinted in the pair's direction trying to remember the attractive brunette's name. ‘Brooks.. Something Brooks.. Lauren!’ Youthful in appearance but if he recalled correctly she was only a few years off from thirty. Making her around his age but older than Clara’s twenty two. She wasn’t a maid, and had a teen son, so he had never considered her as anything more than an employee, but the security officer in his dark slacks with his collared polo shirt made him irrationally angry, thinking about Sydney the head of the hotels security, who was often used as a “fixer” by himself and Moriah.
Taking in a deep breath or trying, the corset making it difficult he gave a small wave in the same manner he had done to Ana the day before when waving goodbye as the receptionist smiled and waved hello when noticing him looking. Not wanting to be drawn into a conversation about the pretty girl’s sad life again and still not comfortable being seen as…as.. A girl. He started walking again to head to the employee locker room. ‘So far so good? Good? Is that the word I want to use for keeping my real identity a secret?’ He asked himself taking the maid uniform out from the locker. Putting it on, swapping his brown faux leather four inch heels for the black ones that were essentially his work shoes. ‘I love it when Moriah wears heels and… god it would have been nice if some of the umm my conquests wore them when I bent them over…’ His mind trailed off briefly, his body having stopped moving as he looked at the maid uniform.
Once fully redressed he glanced in the mirror, his eyes lingering on Clara’s.. His… chest before sliding down across his legs to the footwear. Shaking his head he slightly slapped both cheeks at the same time, smiling once more before leaving the area to head to his destination to tear the prick a new one.
The door to the security office was locked with key card access much like the guest rooms but Calvin no longer had his key card; he only had the one provided to the newly hired junior maid and it was not going to work on any of the office doors. He wanted to call Bethany Long a bitch for telling him he had to earn the right to be trusted, but he also knew when this was over and being looked at like a latina immigrant was over he would fire her if she just handed out access like it is candy to day one employees. ‘Fuck her for being…her, for being responsible like me fuck her for being the right person for te operations director role… the fifty year old… old bat!.’
One problem was that he liked her, but he did not like being treated like he was lower than her. Of course he once liked Sydney Larson too. The man in his young forties with his broad shoulders and dedicated work ethic had freaking betrayed him!
Restraining himself from pounding on the door, he once more mentally reasserted the happier attitude or at least the appearance of it as he knocked on the door.
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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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- 14 Chapters Deep
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