It was break time and Emily looked towards the view of downtown Chicago. She never got tired of it, even after five years on the job. Room service was something she enjoyed. She got to make people happy, meet new and fascinating people on a regular basis, and her work environment was 5 stars.
Her daily meditative moment was disrupted when she heard a distinct voice from behind.
"Sorry about yesterday."
Emily turned around to see a man in a nice suit. He was clearly a business person, a successful one at that. One of Emily's strengths as a room service attendant was that she had a great memory and was able to keep track of most of the guests. This man was Michael.
And judging by that sly smile on his face (which he tried so hard to conceal), nope, he wasn't sorry at all.
The other day, she had brought food to his room, a standard breakfast which he ordered. She knocked several times and there was no answer. Following protocol, she let herself in the room, where she was greeted to the sight of Michael fucking some woman from behind. It was rough and crude. The woman moaned loudly and their bodies made slapping noises from the hard sex. Michael must have definitely heard her knocking and entering, but chose to ignore it.
After getting his attention, he acted apologetic, and the woman he fucked acted mortified. He covered himself by wearing a robe and signed for the food, then she left.
That was yesterday. Today, their meeting was much more proper.
"It was my mistake," she answered diplomatically. "It's my duty to respect the privacy of our guests to the best of my ability."
"But things happen."
He seemingly made himself comfortable standing right next to her by the window.
Emily tensed and changed the subject. "In town for business?"
"Business and pleasure."
"It seems like you've got the pleasure part worked out" she quipped.
Michael laughed. "I have business in Chicago. And I'm also here for the wedding. I'm the best man, and the groom is my business partner. So we're taking care of a lot of important things during this visit."
"The Callahan wedding?"
"That's the one," he acknowledged. "Like I said, business and pleasure. I handle our work-related things while in town, and he gets to marry his honey, who's actually from around here."
Emily couldn't help but give a sly expression of her own. "Speaking of honeys, who was that woman you were with? An acquaintance?"
"Something like that," he smiled. "Someone who shares my passion for passion."
"And exhibitionism, it seems."
"You sound like you're used to walking in on that."
Emily nodded. "It's somewhat of a secret understanding that most in the hotel service industry have. Usually it's a naked guy parading around in his room when he knows an attendant or cleaning lady is coming. Or it's a woman walking naked down the halls with a smile on her face, while her husband takes pictures. And you kind of get used to it. It's part of the job, though it's not written anywhere in the terms of employment."
"I understand. Human sexuality is a complex thing, but I shouldn't have to tell you that."
"Why are you asking me this?" Emily calmly retorted. "Does this turn you on further? Flashing me one day, then questioning me about it the next? It seems like you get twice the thrill, which is both clever and perverted at the same time."
"You're feisty for a polite room service attendant."
"I'm not being feisty at all. I'm just taking my break, so we can talk plainly."
"You want to talk plainly?" he asked.
"Only if you have something interesting to say. You seem enlightening."
"It's naughty. But I want to tell you anyway."
"Why?"
"You'll find out at the end of my story."
Emily's interest was piqued. "Go on, Mr. Interesting. Let's see if you can impress me with your dazzling story."
"It's a habit I picked up from a woman I dated years ago. We were colleagues so we traveled a lot together. She loved public places and the risk of getting caught. She had a penchant for room service in particular. She'd wear a robe after a shower, order some extra towels or food, and 'accidentally' her robe would open, giving the unsuspecting attendant a peek. The look on the attendant's face was always fun, whether it be man or woman. Afterwards, she'd get so aroused that I'd have to fuck her. And that, was what changed me."
"So you're blaming your sinful ways on your ex-girlfriend? Classy."
"Blaming? No way. I love her for it. She really opened my eyes to these sorts of experiences. It brought color to an otherwise bland sex life, though I must admit, I do feel guilty at times."
Emily's eyes wandered around, praying no one heard this very dirty conversation she engaged in. She had worked too hard for her honest reputation.
"Thank you for the interesting morning," she said pleasantly, after she felt it was time to put an end to this. "I hope you got what you wanted from our conversation. Now if you'll excuse me, I have work to do. If you need any room service, be sure to keep your robe nice and tight next time."
"We haven't gotten to the best part yet."
"Oh?"
"People react differently when seeing exhibitionist acts," he said. "Some attendants just turn around and leave, or storm out. Others gawk for a moment before slowly leaving."
"And me? What category did I fall under when I caught you screwing a woman from her behind? Was I repulsed? Or was my inner-slut finally awakened, yearning to be free?"
"In all seriousness, Emily, you had a look which I had seen before in the past. Curiosity. It's a common fantasy for women, this exhibitionist thing, and I've long desired to coach a room service woman into the lifestyle."
Emily gulped loudly. Did this guy really have the balls to ask her such a thing? If so, she wanted to commend him for that kind of courage. In all her years on the job, no one had ever sexually propositioned her so directly and bluntly. It was almost something to be admired.
More importantly, Michael was right. Emily's sexual history was rather bland and routine. Sure, she had fantasies, plenty of them. But they were just that, fantasies. Not something to be explored with a hotel guest, much less a relative stranger.
Could she really...
"I admire your confidence in asking me," she said, mustering her courage to reply.
"I like taking chances. This is something I really want to experience. And I strongly suspect that you do too. I saw your lingering eyes, watching me fuck, watching my cock hang between my robe when I put it on. Maybe I'm being rude by asking you this, but in my opinion, it's best to be upfront, so we're clear about things."
Emily gave an uncharacteristically long pause. "How long will you be staying with us?"
"The wedding is this evening. I leave tomorrow night."
She squinted. "If you plan on marching me to your room for casual sex, then you're sadly mistaken, sir."
"I would never be so brazen."
"Then?"
"A small series of exhibitionist games," he replied. "If you're uncomfortable, then we'll stop. If you're enjoying yourself, then we delve deeper."
"Did you have anything in mind?" she asked without thinking.
"Actually, yes. There's something in mind that I have for you, and just for you. It only works because you're a room service attendant. If everything goes according to plan, it could be quite exciting... for you. Would you like to hear it?"
She slowly nodded. "Why not? It wouldn't hurt to listen."
As Michael talked, Emily made her decision. Surprisingly, it was an easier decision than she ever could have imagined, and that terrified her.
***
After running a few errands, they went to a vacant guest room on the 20th floor. She brought a prepped service cart along with them too.
Once there, she stepped into the bathroom to make a few crucial adjustments underneath her outfit, at Michael's instruction. When she was ready, she stepped out and allowed him to inspect her tidy uniform as she modeled herself.
Outwardly, she looked impeccable, ultra neat, and cute.
Inwardly, she was braless and pantyless.
"How does it feel?" he asked while sitting casually on a bed.
"The fabric of the uniform brushes against my nipples, which are sensitive. It feels more freeing. As for down below, it feels much different. It feels liberating."
"This look suits you well."
"Is it noticeable?" she asked. "Wearing a bra is really important for any woman in uniform. It's necessary to maintain the right shape up top. Otherwise it'll look like my small breasts are hanging freely underneath."
"Your breasts are small enough so that it's not so obvious. But of course, I already know that you're braless, so I can tell."
Emily looked down and smoothed the fabric of her top. "I'm a little insecure that people will notice. That it'll be
too
obvious."
"Only the right people will notice if this works out. Are you aroused now? Does it excite you being dressed like this for work?"
"Yes," she replied curtly.
He probed deeper with his eyes. "Has this always been a fantasy of yours? Have you ever been tempted at all? Or maybe you're a secret bad girl and you've done it already."
"It's a fantasy. A big one of mine. No, I've never flashed a guest before, or anyone else. I'm much too scared. My reputation means a lot to me and I could never forgive myself if my reputation was ruined in any way. And I'm also easily embarrassed, in case you couldn't tell."
"Then why do you trust me? Why make this your first foray?"
Emily gave an honest reply. "I don't know. I guess this is a
'right place at the right time'
sort of thing. You caught me in the right moment with the right approach, I suppose. You seem like you have this all figured out."
"I'm discreet, more than anything."
"As ironic as that sounds," she smiled.
"Emily, I've planned this out with expert precision. I'm treating this like a high-stakes business venture. I've mapped out all the details and scenarios. In short, you'll be fine."
"God, I hope so."
He approached her, then with two hands, he undid the top button of her uniform, then the second one below that. He gave gentle tugs around the chest area, digging his fingers in between the fabric.
