Room Service Hotel Window

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.

"What color are your nipples?" he asked.

"Pink."

"Perfect. It's the bride's favorite color."

Suddenly, Emily tensed and squirmed. She felt her thighs clenching.

"Are you sure this is a good idea? I don't want to interfere with anyone's wedding or relationship. That's never been my thing."

"Trust me," he said. "Bill and Karen are madly in love. They're normal, everyday people. Most importantly of all, they're kinky behind closed doors. You couldn't tell by looking at them, especially Karen, but they know how to have a good time. Are you ready to find out?"

"I'm nervous."

"Are your hands trembling? Are you feeling that adrenaline rush?"

Emily nodded. "Yes."

"Are you wet? That's the big question."

"Yes."

"Well then, Ms. Room Service. You have a job to do. Get to it. They're both still in their separate rooms with their friends. Like I said, you'll be fine."

***

Emily fixed her posture, even as the top of her uniform was open, and from the right angle, either nipple could be seen. She was certain of that because of the air she felt flowing onto her chest and small tits.

The plan was now in effect.

She pushed the cart to the door, and Michael was gentleman enough to open the door for her.

The first stop was the groom's guest room. It was just down the hall and her stomach was in knots as she knocked on the door. It only took a few moments before the groom himself answered. He was dressed in a business casual attire and some of his groomsmen were in the room watching tv. It looked like they were getting ready to head out for lunch.

"Mr. Callahan," she said with her trademark charm. "I have some wine for your room, in anticipation for your wedding this evening."

"How thoughtful of you," Bill Callahan replied. "Please, come in."

Emily pushed the cart inside, thinking how much of a gentleman this guy was. If only he knew about her lack of undergarments. Would he find out? Would he accidentally have a peek? Or did he already catch a glimpse that her top seemed rather open and her small breasts clearly reflected that she wasn't wearing a bra?

Either way, the answer would soon become clear.

When she entered the room, the other men looked at her and smiled, politely saying hello. They were too far away to catch any sort of glimpse at her nipples. Not wanting to be rude or gawk, they returned to watching tv and having their conversation.

She brought the cart to the table and bent over as she put the wine bottles down, allowing her top to fall open from her new position. Bill Callahan approached her from the side to help place the drinking glasses.

"Am I supposed to sign anything for..."

His words came to an abrupt halt. Emily instantly knew why. She couldn't bring herself to face him. Not yet, anyway. She kept her eyes down as she finished placing the items neatly on the table.

Finally, she lifted her eyes and looked at Bill, who had been gazing inside her uniform to see a hardened pink nipple. His eyes turned away the moment he was caught.

"There's nothing to sign," she said with a slightly squeaky voice. "The wine is a gift."

He spoke in a low voice, so his friends wouldn't hear. "Be honest, is this wine really from the hotel, or is it from you?"

"It's from me. My gift to celebrate your momentous occasion."

His eyes gestured down to the top of her open uniform. "And, that?"

"Something for you and your bride to see," she said, nerves bundling. "The hotel has nothing to do with this. It's my gift. Is it too much?"

"No, no, not at all," he replied to put her at ease. "It's the perfect gift, actually. Are those other two wine bottles for my bride?"

"Yes, I'll be taking this to her room next."

"You're just her type," he smiled coyly.

Emily blushed hard, felt a tingling sensation between her legs, and thanked him. When he thanked her in return, she pushed the cart away with her head held down, embarrassed but aroused.

*

Her first exhibitionist moment was a success. She was both mortified and intensely excited. It could have been a career ruining moment. But instead, it was a morale booster of sorts.

As she pushed the cart down the hall to the bride's room, she wondered how Karen would react. It's one thing to 'accidentally' flash a man, but to flash a woman? Her adrenaline was pumping fast.

She knocked on the door to the bride's room. One of the bridesmaids answered, and Emily was allowed in with the service cart. The women in the room were making last minute adjustments to their dresses. They were all barefoot with their dresses on, hair down, with hardly any makeup.

Finally, she met the woman of the hour.

Karen Zhang was a sweet looking Chinese woman who, if Emily remembered correctly, worked in the financial investment world.

"A gift for your wedding," Emily said, gesturing to the cart. "Two bottles of fine wine. I had already brought some to your fiance's room."

Unlike the groom, Karen knew right away that Emily was braless. Maybe it was a woman thing, Emily thought. She noticed Karen looking over her chest, wondering if this was intentional or not. Emily blushed again. For some reason, she felt herself becoming more aroused exposing herself to Karen than Bill. It seemed far more taboo. Maybe it had to do with the fact that Karen was this ultra smart Asian woman, Emily thought.

Emily entered and the bridesmaids seemed enthusiastic about the courtesy wine. Emily smiled at them and they exchanged pleasantries. When the other bridesmaids went back to their dresses, it was just Emily and Karen at the table, putting the wine down.

"You're not wearing a bra," Karen said in a purposeful low voice, without much emotion, while still neatly arranging the glasses.

Emily gulped and tensed. "No, I'm not."

"Did my fiance put you up to this? Was this his idea?"

Karen's face was stoic and impossible to read.

Emily's heart rate was through the roof as they stood face-to-face, woman-to-woman, while the other bridesmaids were busy on the other side of the room.

Was this the part where she'd get into trouble? Was this the part where she'd be reported to management? Her hard-earned reputation destroyed?

"It was my idea," Emily said sheepishly.

"No one put you up to this?"

She confessed. "Michael, one of the groomsmen for your wedding."

"Why didn't you say so?" Karen asked rhetorically, sounding as though her heart rate was rising as well.

Karen's eyes moved downward and Emily could feel that gaze undressing her. A finger was lifted and Karen tugged at Emily's uniform, pulling a button further to the left.

When Emily looked down at her own chest, she saw that the top of her uniform was opened enough on one side so that her stiff pink nipple was visible. The exposure caused her to moisten between the legs.

"Thank you for the wine," Karen said, properly buttoning up Emily's uniform after getting a nice peek.

Finally, the pretty Asian woman cracked a small smile, which she tried to suppress, and then she smoothed the uniform top with the palms of her hands.

Emily stood still and turned her head to make sure none of the bridesmaids had caught them.

"Don't worry," Karen whispered. "I know how to be careful. None of them have seen a thing. Thank you for showing me."

Emily composed herself with proper professionalism. "Ms. Zhang, I wish you, your fiance, and all the guests in attendance nothing but the best. Thank you for staying with us and please let me know if I can be of service."

The comment was loud enough for the bridesmaids to hear, and they all expressed their gratitude once again for the wine.

"You're so very kind," Karen said with a knowing smile, signalling her own arousal.

***

The curtains were wide open when Emily brought the cart back to the vacant room. Michael was sitting by the window, which was adjacent to an office building.

"Amazing view out there," he said, before turning his attention to her. "And keep the door propped open."

Without questioning the order, Emily propped the room door open and went to Michael.

"I did it," she said. "To both of them. They both had a peek inside my top."

"Did they see your nipples?"

"Yes," she replied.

"Did you like it?"

"I did."

"What did you like about it?" he asked.

"It was a massive adrenaline rush," she replied. "Above all else, it reminded me what I love about this job. Whether I'm welcoming visitors who seem enamored with this hotel, helping people solve their problems, or bringing up great food to people's rooms, I'm always helping to brighten someone's day."

"You must have certainly made an impact then. Bill and Karen must have really loved the view."

Emily nodded. "They were both enticed by it. Especially Karen. She actually used her finger to lift my uniform to look at my nipple. It's like she understood what I was feeling at the moment."

"Touch yourself between your legs. Then show me your fingers."

She took a moment to decide. When she made her decision, she reached underneath her skirt, gave herself a soft touch, and showed the wet result to Michael.

"There," she said, holding out her open palm.

"Good girl. Now take off your uniform."

Emily's eyes instinctively shifted to the hotel window. She saw office workers going about their day. It was mildly foggy outside, so there wasn't any glare from the sun. The view was clear and unobstructed.

"Why?" she asked nervously.

"You already know why."

Emily did. She pinched the hem of her skirt and lifted the entire uniform overhead, tossing it to the bed. There she stood, naked and bare. Her slender and youthful figure on full display, with her small tits pointed forward and her pink nipples at full attention.