Cindy's Adventures in NYC Ch. 02

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Men take advantage of naive Midwest teenager in big city.
4.3k words
4.4
101.6k
37

Part 2 of the 6 part series

Updated 10/29/2022
Created 09/14/2013
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Cindy shuffled on her high heels anxiously. So much as had happened to her over the few months since she arrived in New York, she had never done anything like this. To parade around the room in front of all those men...wearing just this tiny little thong. Her thoughts continued to drift to how she had got to this point.

Posing nude for her roommate's boyfriend Barry had been a wake-up call for Cindy. It's true she had thought about how naughty she was, and even fantasized about him watching her masturbate as she lay down in her tiny curtained off 'room'. But she always felt angry at herself afterwards. Since Barry had cum on her feet, Cindy has avoided him the best she could, and was determined to find a real job.

Cindy had gone on many interviews, but always seemed to fall short. She thought she came across well, but her complete lack of experience seemed to be a real roadblock. Cindy was resilient, and her roommates would sometimes tease her as she put on her only 'interview outfit' every morning before heading out.

One Friday, just when she was at a low point and thinking she might have to admit she couldn't cut in the big city, Cindy got a call asking her to come in for an interview with a small agency that rented out office space. It had nothing to do with her aspirations to become a reporter, but it didn't require a lot of experience. Cindy put on her suit, a gray skirt then went just above her knees, with a matching gray jacket and a white blouse. She generally put on tights, but because she had to rush for the interview, left with bare legs. Cindy tottered a little in the black high heels she only wore for interviews as she raced down the street to get the bus.

Standing on the bus on the way to the interview Cindy tried to psych herself up. She really wanted to make a great impression. Cindy looked at her reflection in the bus window as it rolled slowly down the road and told herself she looked good. She reminded herself to relax during the interview. The man on the phone had sounded very nice and laid back.

When Cindy got off the bus she raced down the street to the address. She was tight on time and knew she couldn't afford to be late. Cindy arrived at the office with a few minutes to spare. There was no receptionist to greet her, so Cindy stood in the small lobby anxiously. Suddenly a man arrived. He was an average looking man, but had a nice energy about him. He walked up to Cindy and with a jovial voice and a southern drawl shouted, "Cindy, is that you?"

Cindy smiled, nodded and put out her hand. The man shook it firmly and looked her up and down. "I'm Ed. Come on in, have a seat in my office."

Cindy followed Ed into his office and he motioned for her to sit on the couch as he pulled up a chair. Cindy sank into the deep cushion and as she fell back she felt her skirt ride up her legs. Cindy wanted to pull it back down but with Ed right in front of her she didn't want to seem as if she was concerned with him looking at her legs.

"So, you'd like to be our new Office Assistant?"

Cindy hadn't even known what the role was. She had applied to so many jobs it was hard to keep track. She expressed her enthusiasm for the role and asked if he could tell her more about it.

"Well, there are five of us here in the office when we're not out in the field. We need someone to answer the phones and greet visitors. The guys may need some help from time to time, copying or filing. And of course it's important to have a pretty girl around to brighten things up a little."

Cindy nodded sagely while Ed talked, trying hard to look professional. She crossed her legs, then realized that in doing so she was exposing even more skin, perhaps even showing a bit of her panties . She couldn't do anything about it without making it seem she though Ed was a perv so she acted confident.

"Well, I think I'm your girl."

Ed smirked a little and slowly gazed down at Cindy's breasts, her legs, her shoe, then back up and right into her eyes. "Mmm...you do, do you?"

Cindy nodded vigorously. Her throat felt dry. She really needed this job.

"Well, darling, I guess there is only one way to find out. You come back at 9am Monday and we'll get started."

Cindy squealed a little, before realizing that was very unprofessional. Ed gallantly put out his hand to help her rise from the plush couch and she accepted, falling into him a little as she stood. While walking her out Ed stopped at another office. "Cindy, this is my partner Tony, Tony, this is our new Office Manager."

Cindy started to out out her hand, but Tony just looked at Cindy without a serious expression. "I see. Well, we'll see how you do."

Cindy smiled and assured him "Oh, I am very eager to make a good impression, thank you for the opportunity." Tony looked her up and down again, then simply nodded.

When Cindy got out on the street she had a skip in her step. She finally had a real job! In New York City! She realized she had not asked the pay but she was knew it would be much more than she had been making to date. She was determined to do great there - and she started Monday!

When Cindy returned she wanted to share her big news with everyone, but she was taken aback to find only two men in the kitchen, Barry and Eric. Cindy was immediately self-conscious, as she had been every time she had seen Barry since the time she had 'modeled' for him. They had never spoken about that time, and until now he had always been with Anna, her roommate and his girlfriend.

Cindy noticed that Eric, a large black man who was Eric's friend and the sometimes boyfriend of Stephanie, another roommate, was staring overtly at her body with a smirk. She thought she saw him share a knowing glance with Barry and folded her arms over her breasts. She wondered if Barry might have told Eric what she had done for him. Cindy excused herself to her little room, and could feel four eyes on her ass as she walked away. She closed the curtain then let out a little squeal again with excitement around her new role.

It felt like Monday would never come, but when it did Cindy was up early. She had noticed that Ed and Tony were dressed 'business casual', so she wanted to find the right outfits. She had been to H&M and bought parts of two outfits, including the one she had chosen for her first day, black slacks, and tight white top and a beige jacket. In doing so she had maxed out her credit card, but even with no cash she figured she could get by until payday.

Cindy checked herself out in the mirror and knew she looked good. The top was tight enough to show off her curves, but the jacket kept it professional looking. It also covered her ass, which she knew sometimes distracted guys. Cindy was confident she would make a good impression on Ed, Tony and the new men she had yet to meet. She even practiced her phone voice on the weekend and felt she was ready to go.

Cindy arrived more than half an hour early so she walked up and down the block a few times. Finally, about ten minutes before 9am she went up the elevator and into the office. Again nobody was there, so she tentatively walked towards Ed's office.

"Good morning doll!" Ed said with a booming voice when she stood in his doorway. "Aren't you an eager beaver?"

Cindy blushed a little and Ed motioned for her to come in. Ed looked at Cindy and frowned. It was the first time Cindy had seen him look serious, even disappointed, and she worried about what might be wrong.

"Cindy," Ed started with a slow drawl, "I thought I mentioned that a big part of this role was to 'brighten up' the office for the boys."

Cindy was confused and waited for Ed to continue, and when he didn't she felt even more anxious "Yes, you did. I mean, is there...?"

"That outfit. Very professional and all but we need something more...playful."

Cindy tried to process the implications. Ed has made it clear that she was meant to brighten up the office. Does he mean brighter colors, more revealing? She thought about what she could have worn that might have pleased Ed more.

"Why don't you head out and come back wearing something more appropriate."

Ed took out his wallet and handed her $50. "This will help if you need to buy something pretty."

Cindy took the money and thanked Ed, then scurried out of his office and back to the streets. She felt rather like a scolded girl as she waited for the bus back to her apartment. She knew she had to do well at this new job and her mind raced through possible outfits she could wear. She looked out the window on the bus ride home for inspiration based on what other girls were wearing. Which ones brightened up their surroundings? Which girls looked 'playful'?

When Cindy arrived at her apartment she was focused and wanted to change quickly so she could return to the office and get started. When she arrived she saw two of her roommates, Stephanie and Anna sitting at the kitchen table drinking coffee and smoking pot. They both looked up at Cindy.

"Hey girl, I thought you started your big job today?" Stephanie asked with a giggle.

Cindy murmured something about forgetting something and went into her little room. Her clothes were in a suitcase in the corner and she looked through them frantically to find something more appropriate. Of course with all men in the office they would want her to wear something prettier she thought, chastising herself. Ed had said so himself, and she needed to do a better job listening.

Cindy found the blue dress she wore to her prom. It was rather revealing, showing a lot of leg and ample cleavage, but she certainly knew she looked pretty in it, and there was no doubt it was 'bright'. She didn't really have time to waste, so she undressed quickly and squeezed herself into the dress. It was strapless, and she could not wear a bra with it. Cindy remembered that her ex. boyfriend in Eureka had lifted the dress up and fucked her in the back of his car after the prom and felt herself moisten a little. She shook off the thoughts, put her heels back on and looked at herself in the mirror. She definitely looked nice, but was it too much? She decided it would have to please Ed and the boys at the office, grabbed her purse and left the room.

Stephanie and Anna immediately catcalled as she walked by.

"Wow, girl, what kind of job do you have over there?!" Stephanie giggled.

Cindy had no time to explain, not that she would have known what to say, so she just smiled and left the apartment. She decided she needed to get back to the office as quickly as possible, so she used $15 of the money Ed had given her to take a taxi there. She noticed the taxi driver checking her out in his mirror and was conscious of how much leg she was showing as she sat in the back seat. She reminded herself how great she looked and told herself Ed would be pleased at how she listened.

Ed was indeed pleased when Cindy arrived. He had her spin around for him and told her that was exactly the kind of outfit she should wear. "I mean of course you're here to do work darling, but you also make an impact just by being here." he smiled.

Cindy thanked him and promised she understood. Ed walked her over to Tony's office and although Tony said little she could see he was impressed with her. She thanked him for the opportunity. Ed set Cindy up at the receptionist desk and gave her some company literature to read. He told her she would be introduced to the rest of the team, three men, at 11am.

Cindy settled in. She read through the brochures she had been given in a few minutes, and wondered what time the other men would arrive. She sat up straight, as she noticed that any time she slouched her dress rode up such that anybody at the desk could see much far too much leg. She hoped the other men would understand why she was dressed in such a small dress. It was, after all, just for them. She listened to Ed talking on his speaker phone and wondered if there was any work she should be doing.

At 10:30 Ed came bursting out of his office. "Cindy, how about you fetch me a coffee darlin'?"

Cindy was grateful to be of some use as she walked over to the coffee machine and took out a pod. Ed stood and watched her, and Cindy felt very conscious of how she was walking in her high heels...and how tight the dress was around her ass. At Ed's instruction she added lots of sugar, then walked over to him with the cup.

At that moment a young man walked in. He was Cindy's age, but looked even younger, skinny and awkward the way 18 year old boys can be.

"Junior, right on time!" Ed bellowed.

"Cindy, this here is my boy Eddie!" Ed put his hand gently on Cindy's bottom and directed her towards the young man.

Cindy put out her little hand and Eddie took in in a soft handshake, looking down at her tits, unable to meet her eyes.

"Nice to meet you Eddie." Cindy smiled.

"Not bad eh Junior?!" Eddie smirked. "We got ourselves a winner in Cindy, right?"

Eddie smiled but looked down at his feet.

"Look alive Junior. A beautiful young girl joins the team and you look like you'd rather be somewhere else!"

Ed reached over and steered Cindy to turn around. "Look at her Junior" he said gesturing to Cindy's ass and legs, "Isn't she going to brighten up the office nicely?"

"Yes sir she will" Eddie answered softly.

Two more men arrived, both taking note of Cindy in her tight prom dress immediately. One was a big, tall Hispanic gentleman, very attractive Cindy noted, the other a small man who never took his eyes off of the new Office Manager. Ed greeted them warmly and promised they'd get to meet the young lady shortly. He took them into the conference room, along with Eddie. About a minute later Tony walked by, nodding simply at Cindy as he too walked into the conference room.

Cindy sat alone at her desk, waiting for 11am. One call came in, but it was someone selling office supplies, so she took a message. Just before 11, Cindy rushed into the restroom to make sure she looked good. She felt a pang of nervousness, but also excitement. She was to be officially introduced to all the men she would be assisting in her new role and wanted to ensure she made a great first impression.

Cindy was waiting at her desk anxiously when Ed came out to get her a 11:05. Cindy walked in and found the four other men waiting for her, looking up from their seats around the conference table.

"Guys, this is Cindy, our new Office Manager. Cindy, come closer so the boys can see you." Ed once again placed his hand on Cindy's ass and guided her so she was at the front of the room for all to see.

"Very nice!" the short man remarked and there was a murmur of approval in the room.

"Cindy doesn't have any qualifications, but she has assured me she is up for the role." Ed noted.

Cindy blushed a little and wondered if she should say something. Instead she nodded dumbly.

"Tell us where you got that lovely outfit Cindy." Ed asked.

When Cindy stammered that she had got it for her prom, and the men laughed heartily and told her they were glad she had found another use for it. Ed noted that Cindy must have pocketed the money he gave her, then chastised his son for not finding a hot girl like Cindy for his prom. Cindy felt the heat rise to her face as she blushed again. Ed had Cindy turn around for the group and Cindy was reminded of her 'modeling' for Barry when she could feel everyone's eyes on her ass. She felt herself get a little aroused and shook her head to clear her mind of the thought.

Ed asked her to go an introduce herself to everyone, so she walked tentatively to shake the short man's hand who was closest to her. He stood up to give her a hug, which surprised her. She felt her breasts press against his neck as he introduced himself as Danny. Danny then patted her ass twice, seemingly as an indication she was free to move on. Cindy noticed her nipples were hard and knew they must be showing through the dress.

Tony was next and though she had already met him, it seemed to Cindy he also expected a hug. Tony did not get up from his chair so Cindy bent down, realizing as she did so that she was exposing an awful lot of cleavage. Feeling very awkward since Tony did not hug her back, Cindy thanked him again and gave him a bit of a kiss against his cheek. Cindy felt something brush against her bottom and realized that in bending over she might be exposing herself in this short dress. She turned her head to see that she had given Danny a close-up view of how tight her skirt was around her bottom, and that from his seated vantage point he had almost definitely seen even more.

Cindy scurried over to the other side of the table, feeling a little dizzy. She almost tripped as she maneuvered on her high heels. Everyone seemed nice, but she somehow felt she didn't belong. She tried to clear her head as she approached the handsome, tall Hispanic man. He wore a white shirt and a jacket and looked quite striking. The man stood up and smiled. Cindy felt relieved by his welcome, and fell into his open arms, her head against his chest. She realized as she did this that she probably looked like a little girl in her daddy's arms, but he smelled nice and held her tight. The man kissed her forehead, whispered that his name was James and told her with a soft accent that he was glad she had joined the team. James loosened his embrace and as Cindy withdrew she felt him squeeze her ass cheek with a big hand. Cindy knew this was not normal behavior for the office, but she was somehow a little grateful...it was like she had been accepted into the club. She looked up and him and smiled, thanked him, then looked over to see Eddie in the final chair.

Eddie hesitated, then stood and Cindy gave him an awkward embrace. He mumbled something unintelligible. Cindy could feel that he was hard and reflectively pulled away. Eddie looked mortified.

Ed, still at the front of the room scolded his son once more, "Junior, you don't even know how to hug a beautiful woman!"

Ed then took Cindy by the hand and slowly wrapped his arms around her. His hands rested on her ass and she let him pull her in so her head was on his shoulder. He whispered in her ear that she had done very well, then patted her twice on the ass as Danny had done earlier.

The rest of the day was rather uneventful. When Cindy brought the men lunch they all seemed pleased to see her. Danny and Ed both managed to cop a feel of her ass as she squeezed between them to reach the table.

In the afternoon, Cindy was actually given a small assignment, filing some papers. The men stayed in the conference room for the rest of the day. Occasionally one would come out and ask for a coffee, always staying to watch her make it for them. Danny came out and chatted Cindy up a while bending over her desk. He didn't hide that he was checking out her tits. Cindy felt confident she could handle Danny. If he enjoyed looking, well, I guess that was part of her role, right?

At the end of the day Cindy asked Ed it was ok to leave, then received hugs goodbye from James and Danny. During his hug, Danny stroked the back of Cindy's bare leg, just below her ass, then gave her bum a lingering squeeze. Cindy wondered if perhaps she should have protested or moved his hand earlier. Now Danny seemed to believe he had free access.

Despite some misgivings Cindy felt very good and decided to walk back to her apartment. She noticed the lustful glances from men as she walked awkwardly in her heels, but it didn't matter. She had started her career here in New York, and everything seemed bright.

Cindy hummed a song as she arrived back at the apartment. She opened the door with a skip, and once again found Barry and Eric, sitting at the table as if they had been waiting for her. The two complemented her on how nice she looked in her pretty dress, as she noted the smell of pot in the air. She started to walk to her room when Eric put a hand on her arm and said "Cindy, when are you going to show me your sweet ass like you showed Barry?"

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