Cindy's Adventures in NYC Ch. 05

Cindy woke up to her alarm and remembered the previous night in a blur. She had been in her boss' lap in that tiny skirt, everyone in the bar had seen her ass, and every colleague at Happy Hour had kissed her. Then...on the way home, gosh, she given a stranger a blow job?!

It occurred to Cindy that her roommate Stephanie knew what a slutty girl she had been and for a while she considered staying behind the curtain of her little room. She decided of course, that she had to get to work, so ran out and into the shower.

Despite herself, Cindy felt a little turned on in the shower as she remembered more about the night before. She had to admit that she did love all the attention. They all seemed so pleased with her.

Cindy didn't spend a lot of time worrying about her outfit since she knew she would have to change to the maid's outfit that had been chosen for her and was waiting at the office. As much as Cindy at first had concerns with the men at the office picking out outfits for her, she had to admit it was easy, and she knew they enjoyed it.

Cindy did spend some time considering her lingerie. She went with a black bra and panties. She was a bit concerned that the panties were a thong as she knew her bum would be exposed a few times, but her other panties were all rather unappealing. Cindy realized she would have to invest in some better lingerie to do well in this role.

As she threw on jeans and a tight t shirt and hustled out to the bus, Cindy felt the tingle of anticipation of what was to come. The bus shook slowly along and when she arrived she had a skip in her step as she got to the lobby. Cindy waved at the smiling security guards as she got to the elevator and when she got to her floor she went to her desk and quickly retrieved the maid's outfit. She was about to retreat to the ladies room to change but as she turned she saw Tony, who must have arrived early.

Cindy felt her heart beat a little fast at seeing Tony, who had always made her nervous. She started to say good morning, but he cut her off.

"Cindy, is that your outfit for the day?"

Cindy nodded but Tony barely waited for the answer. "Why don't you change in my office? I'd like to hear how things are going."

Cindy hesitated but Tony caustically reminded her he had seen everything before. She decided it would be best to go ahead before anyone else arrived and followed Tony into his office as he shut the door.

Tony did not say anything, but pulled his chair away from his desk and sat so he was now facing the teen. Cindy felt like she was about to do a table dance for him, and she realized that she was indeed about to strip right in front of him. She felt grateful that she had chosen the nicer lingerie.

Cindy paused a moment waiting for instructions, but realized that Tony was waiting on her. Her hands shook slightly as she lifted her t shirt over her head. Cindy now stood in front of her boss in a bra that pushed her tits out invitingly. Tony studied her body but said nothing and expressed little. Cindy undid the button and zipper on her jeans but as she started to peel them down she realized she needed to remove the open toed, black high heel shoes she had chosen. Cindy awkwardly bent down to remove the straps. As she did so she could see that Tony was enjoying watching her. He could probably see her nipples, and as she bent forward they were just a foot away from his face.

Cindy struggled a little with the straps but Tony made no effort to help and said nothing. She finally stepped out of her shoes, stood up and pulled down her jeans. As she did this it occurred to her that she could never have imagined the scenario just a week earlier. She was standing in front of her boss in just the tiniest of lingerie. She had in fact stripped for him without any objection. Cindy felt herself getting excited by Tony's intense gaze.

She paused a moment then reached for her outfit when Tony finally spoke, mocking Cindy quietly.

"So you do like showing off that tight little body to everyone?"

Before Cindy could answer he asserted calmly "Turn around for me."

Cindy turned with little hesitation, even though she knew her bottom would be almost fully exposed to Tony given how tiny her thong was. She bent forward without being told to do so, and could feel herself get wet as he placed a hand just above her knee then slowly let it rise on her leg.

"You do, don't you Cindy? You like having all these men see you wearing these slutty outfits."

Cindy could not bring herself to speak as her breath started to quicken. She nodded although Tony could not have seen her do so with her ass in his face.

Tony's hand lightly stroked Cindy's bare skin as he followed her leg up her inner thigh. Cindy wiggled her ass a bit in anticipation. He teased her with his fingers tracing along up her ass crack, then back down again, stroking her clit ever so softly through her tiny panties. Cindy couldn't help herself as she pushed her ass out close to him and whimpered softly. She wanted his fingers inside her, and it was driving her crazy to have them so close.

"Cindy, you're soaking wet and I have barely touched you. Are you like this with every man?"

Cindy answered quickly with a hoarse voice, "No...I mean I don't...other men have not..."

Tony chuckled and it startled Cindy as she had never seen him smile or laugh. She turned to look back at him over her shoulder but as she did she felt two of his fingers slip under her panties and into her. She groaned and pushed so the fingers went deeper.

"Mmm...that's my girl Cindy, you need this don't you?"

Cindy could only whimper as she moved her pussy up and down over his fingers.

"Cindy, going forward I would like you here at 8am to change in my office, is that understood?"

Cindy nodded again as she kept her rhythm. She thought about what a whore she must look like, almost naked, bent over and riding her bosses fingers while he sat fully clothed in his chair. This somehow excited her more and she could feel that she would cum.

Tony suddenly pulled his fingers away without ceremony. He wiped them on her legs, which already had her own juices on her inner thighs.

"We'll have more time tomorrow." Tony said in way that made it clear she was excused until that time.

Cindy tried to collect herself as she saw Tony shift his chair and start to work at his desk, paying her no further mind. She fumbled to put on her maid's outfit, wiping the wetness with her hands first so as not to stain it. She felt so dirty and she smelled strongly of sex.

Cindy put her shoes back on, then picked up her jeans and t shirt.

"Thank you." she said, unsure of the protocol.

Tony said nothing as he tapped on his computer and Cindy left his office quietly. Cindy hoped against hope that she could get to the restroom without anyone seeing her and although she heard Ed's loud voice on the phone in his office she managed to do just that. Alone in the bathroom she caught her breath and looked at herself in the mirror. She saw just how sexy she looked and felt a strange mix or pride and shame. Was she now going to get finger fucked every morning by her boss? Or perhaps more?

Cindy felt herself getting wet again and tried to shake off the thoughts. She was concerned on how fast her life was changing. She had so little experience with men, and now her career seemed to push her into situations every day that were new and exciting, but also scary.

Cindy adjusted her skirt so she could keep as much decency as possible. The black maid skirt was actually slightly less revealing than the previous day's, but since the short skirt's white ruffles jutted out it promised and delivered an easy view of Cindy's bottom with the slightest bend or breeze. The top was a black bustier that was more lingerie than a blouse. They presented her tits as though they were a gift for anyone passing by to enjoy.

Cindy looked at her watch and saw she was now late, so she pushed her jeans and shirt into her purse and walked quickly in her heels out to her desk. She was happy there was nobody around as this would give her a chance to gather herself. Cindy shuffled through some papers on her desk and got up to get a water when the FedEx man arrived. Cindy looked over and waved with a smile. It was the same man who had been there every day this week, and he seemed to have a crush on her. He was just a few years older than Cindy. Not an attractive guy but he showed off some large muscles in his black polo shirt.

The delivery man let out a whistle, "Hoo, look what they have you wearing today!"

The man looked Cindy up and down and said, "Come here doll so I can have a better look. You're the highlight of my day."

Cindy demurred, standing still a few feet away but when the man asked again a little louder she thought it best not to make a scene. She took a couple of steps forward so she was now just over a foot away. Cindy curtsied a little, trying to lighten the nervousness she felt.

"Wow, you are a hottie for sure. These guys really know what they are doing!"

The man then started to walk around Cindy, who stood in place, letting him take look at her as he wished Suddenly she started as she felt his rough hand go up her skirt and grab an ass cheek with a squeeze. The man moved in close and whispered over her shoulder into her ear "Good girl. I'll see you tomorrow."

Cindy stayed frozen in place while the man walked out the door and towards the elevator. The day had just started and two men had already had their hands on her. She didn't even know the name of the last man.

The remainder of the morning was relatively uneventful. Ed and Danny both came. Both gave Cindy a hug, telling her how fun last night had been. Both told Cindy how great she looked and both allowed their hands to go up under her skirt and grope her ass. She was keeping count and it was now four men who had grabbed her bum and the morning wasn't over.

Just before lunch James came in, along with a prospective client. Cindy hasn't seen James since Tuesday and she remembered why he was her favorite. He was tall, dashing, and somehow made her feel safe when he was around. James greeted Cindy warmly with a gentle hug. James admired Cindy's body but in a much more discrete way than the others.

The client with him was less genteel. His eyes almost bugged out as he stared at her tits. James introduce him as Wu Chan, but the man insisted in heavily accented English that she call him 'Harry'. Harry was a short Asian man, dressed in fancy designer clothes. James explained that Harry was looking to invest in a retail space downtown.

James told Harry that they could meet in the conference room down the hall. James started that way but Harry stayed with Cindy. He asked how old she was and Cindy could see he was excited to hear she was just 18. Harry looked at her maid's outfit and asked in halting English if she cleaned at the office. Cindy said she did a little but mainly answered the phone and greeted guests.

James came back to get Harry and the two of them walked down the hall, but Cindy saw them stop as Harry was trying to emphasize some point. The two of them went back and forth until she heard James tell Harry to sit in the conference room so he could check.

James walked a little slowly back to Cindy's desk and started, "So, Wu Chan really likes you and..."

Cindy looked up at James quizzically. He looked anxious.

"Cindy he would like you to clean his office for him this afternoon. I know that is really unusual, but he is a major potential opportunity for the firm. If you can do this I will cover off for you with Ed an Tony and can give you an extra...$100?"

Cindy bit her lower lip. She could certainly use the $100 but she was unsure about how wise it would be to go off with this stranger to clean for him wearing this tiny outfit. She looked at James and could see how important it was to him and knew she very much wanted to please him.

"Yes...I mean, ok if that's what you want..."

James was jubilant. He kissed Cindy on the lips and thanked her telling her how much this would help. He even gave her the $100 right there from his wallet.

"Just give me a call if there is any concerns Cindy." James said as he walked her to the room.

"Good news!" he exclaimed as they walked in, "Cindy has agreed to be your maid for the afternoon Harry!"

Cindy was a little taken aback that she was being referred to as a maid, but she supposed that was what she would be doing. Harry beamed a bright smile as he looked at Cindy. Unsure of what to do, Cindy curtsied as she had with the FedEx man.

Harry high fived James, then turned to Cindy, "Let go, driver is waiting."

Harry grabbed Cindy's hand as he walked out. Cindy looked back at James who simply smiled approvingly.

The car was indeed waiting, and Harry opened the door of the big black limo for her. Cindy felt like a little Princess as she fell back into the soft seat. She had never been in a limo before. Her boyfriend had looked into one for their prom but it was too expensive. She has ended the night in the back seat of his Kia as usual.

Harry offered her some whiskey and she thought it rude to refuse. She was reassured that he was not as grabby as some of the other men as he toasted to her. Harry took some pictures of her with his phone and Cindy felt even more special. Soon they arrived at Harry's office. Harry took her hand again and let her to the elevator. The security men in the lobby knew Harry, and were surprised to see him with a scantily dressed French Maid.

As they got off on the top floor Cindy felt a little light headed from the whiskey. She hadn't eaten anything all day. Harry opened the door to his office. She had not known what to expect, but it was a small office, very bright, with nice views of the city. There were three people sitting in the open space, two Asian men one in his thirties another in his fifties, a cute, perky Asian girl who looked to be 25. Not surprisingly they all looked up at the young girl dressed in the little maid's costume that was with their boss.

Harry started to speak in a sing-song foreign language to the others, gesturing occasionally at Cindy who stood there awkwardly. At one point they all laughed as they looked at her, which made her shift her feet and look to the floor. Harry motioned for the younger man to take pictures then posed with his arm around Cindy as the man clicked away with his phone. Harry then talked fast in his language to the girl who shuffled her feet to join Cindy and pose with her. The girl was smiling and laughing as she showed a bit of leg lifting her skirt, then she pushed her small tits together and motioned for Cindy to do the same. Cindy felt rather silly as she lifted her much bigger boobs for the picture but everyone was enjoying a light hearted moment and the man continued to take pictures. Harry poured everyone shots of something strong which everyone including Cindy drank down after a toast in some other language.

After the drink Cindy felt even more disoriented. She wondered if anyone other than Harry even spoke English. She started to ask Harry about whether she should clean but he broke in and shouted something to the Asian girl who scurried off and returned with a cloth and some cleaning spray.

"Ok, you clean floors." Harry said, smiling.

Cindy looked down at the floors, which seemed be sparkling. She looked back at Harry who seemed eager to have her get to work. Cindy knew she had to follow through with her promise, and decided she would have fun with it. Harry was an important client and she knew James was counting on her.

Cindy took the spray and cloth and knelt on the floor. She raised her ass, knowing what the men would want to see and started to scrub the perfectly clean floor. While she did this she wiggled her bottom back and forth. One of the men started to take pictures from behind, and Cindy looked back and smiled for the camera. When the man bent down for a closer picture Cindy worried that she may be exposing some of her asshole bending over in such a tiny thong but realized it was too late now. Maybe it was the drinks, but somehow she was enjoying the genuine excitement of everyone. Cindy cleaned for some time as the men watched and took pictures.

Finally Harry told her to stand, taking her hand to help her up. He said something to the perky Asian office girl who waved her hand and seemed to say no. The other men were encouraging her in their language and finally the girl laughed and walked to Cindy. Harry poured them both shots and Cindy accepted the girl's toast before they both drank them down. The girl then moved in close to Cindy and kissed her. At first it was a little kiss, but when Cindy didn't object and the men cheered, the girl kissed Cindy harder. Cindy had never kissed another girl like this. The main thought in her head was how soft this girl's lips were compared to the boys she had kissed. Cindy didn't object when the girl squeezed her tit and the girls continued to please the men with their show.

When the girl finally pulled away Harry was clearly delighted. He praised the Asian girl, then asked Cindy if she would clean his office a little. Harry put out his hand and when Cindy took it he led her to his private office. Cindy was amazed how elegant the office was and she admired the view and Harry shut the door.

Harry asked in broken English if Cindy would take off her top and shine his shoes. At first Cindy did not understand but the man made it clear what he was asking for with hand language. Cindy looked at Harry's shoes as if this would help her understand what to do next. Harry went to his desk and pulled out a box. He opened it and exposed a pretty necklace. He motioned for Cindy to turn, then placed it on her neck.

Cindy was shocked to receive such a nice gift. She was impressed by what a gentleman Harry was and decided it would be fine to shine his shoes if that is what he wanted. She knelt in front of him but Harry reminded her that she needed to take her top off. Looking up at him, Cindy unbuttoned her blouse and removed it, exposing her jiggling breasts and perfect pink nipples.

Harry was delighted and told her how good she was. Cindy started to shine with the cloth. She remembered how innocent her friends all thought she was so innocent and wondered what they would think if they saw her wearing only heels and the tiniest of skirts, shining the shoes of a man she just met.

Harry broke her reverie by asking her to look up. When she did as she was told, Harry unzipped his pants and pulled out his cock. Cindy immediately flashed back to last night and thought how much smaller it was than Keshon's.

Cindy was not naive and knew what the man expected. She also knew she needed to make him happy so she wrapped her lips around his thin cock and took it down her throat in the way her teacher had taught her to do in the back of his car. Cindy looked up at Harry and saw his eyes were rolling back in his head so she knew she was doing it right. Cindy moved her mouth back and forth on his cock and was surprised when she realized he was already about to cum. She swallowed it all, again as she had been taught to do by her teacher and Harry pulled his cock from her mouth.

Cindy stayed kneeling for a time while Harry breathed heavily. Finally he looked down and told her she did very well. He helped her up. Harry looked Cindy in the eye as he pinched one of her nipples and told her in broken English that he hoped to see her again. He helped her on with her bra and blouse then he escorted her out of his office.

Cindy was a little unsure if anything else was expected of her, but the Asian girl smiled and took her to the elevator. On the way down Cindy felt pleased with herself. She was confident she had done what she needed to do for an important client. When she walked into the street Cindy squinted from the sun and realized she was still rather drunk. She did not know the neighborhood and wondered what bus line ran nearby when she saw James standing by his car on the street waving. She walked over and saw him beaming.