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Cindy's Adventures in NYC Ch. 01

By: writemarksmith



Cindy took a deep breath. She was about to walk into a room of strangers wearing just a thong and high heels. Just three months before she had only been naked for one boy...her mind raced through how much had changed so quickly.

Cindy had left her home in Wisconsin in May, only 2 months after her eighteenth birthday. She was sad to leave her the only real boyfriend she had had, but she was focussed on her dream of becoming a reporter and knew NYC was where she could make it big. She had received top marks for English all through school, and had been the head reporter and editor of her high school paper. 

When Cindy arrived, quickly discovered that her high school degree meant little and she would have to start at the bottom to work her way up. She worked as an intern at a small company that sold advertising on blogs, but she quickly found that the stipend she was paid was not nearly enough to get by. He parents had paid for her share of the rent for through the summer (she shared an apartment with three other girls), but food, transportation...everything was so expensive her in the city. 

Cindy knew she was a pretty girl, so she thought perhaps she could do a little modeling to help pay some bills. Scandinavian by descent, Cindy had milky smooth white skin, large breasts, a firm young bottom, and her blonde hair naturally caught guys' attention. She was often compared to a young Carrie Underwood. 

Cindy tried a couple of modeling jobs she found on Craigslist. The first went all right. A man in his early forties wanted to take pictured of her feet. Cindy thought this was rater strange, but he told her she had perfect little feet. As she lay back on the couch, lifted her legs and wiggled her toes for the camera, she could see that just looking at her feet was making him hard, but he was a gentleman throughout. The $60 he paid her ($10 more than promised) was much needed to get food for the week. 

The second job as not as easy. The ad had said the modeling it would be for bathing suits. When Cindy arrived at the apartment she met a boy who was in his early twenties. Somehow she felt more uncomfortable with a guy much closer to her age paying for her to pose for him, and when he told her to just strip down and pose in her lingerie, she balked. When the boy promised to pay her twice the $50 that was advertised, she decided that her panties were not much more revealing than a bathing suit, and after taking the money, she took off her jeans and t shirt, and stood before him in her beige bra and pink panties. She saw in the mirror that her panties were rather small, and she pulled them to better cover an ass cheek that was almost completely exposed, then decided there was not much use. 

The boy told her to pose in sexual ways, similar to Sports Illustrated Swimsuit edition. She had to push her breasts together to accentuate her ample cleavage, give a pouting come hither look. The boy told her he wanted some good shots of her ass and told her to bend over the table. Cindy felt very exposed as she followed his instructions, but the boy wanted more. He walked over and pushed her back down, then patted her ass, direction her to raise it even higher. She felt the material of her panties pulling against her, and wondered just what she was exposing as he took picture after picture. She felt very uncomfortable, but also a little aroused as he kneeled just behind her, taking a close up of her ass that she was pushing out for him. 

Suddenly he stopped and told her she better get dressed before his parents got back. He thanked her for coming and asked her to come again in a few days. Cindy pulled on her clothes with some urgency. When she got out to the lobby of the apartment, she felt like the people entering must all know what she had been doing. She still felt naked. On the bus back to her place she asked if she should even consider another modeling gig, even though she was grateful to have some cash. 

The next morning, Cindy slept in late behind the curtains of her makeshift 'room' in the apartment she shared. She heard her roommates leave for their jobs and reminded herself she needed to find a proper one.

Cindy forced herself to get out of bed, then took her old laptop out on the kitchen table and began searching the ads. Every one seemed to want a college degree or to pay the minimum. She cursed quietly to herself, and switched to Craigslist, taking another look at the modeling gigs that were offered. Many offered only pictures for compensation, others were clearly just covers for guys wanting sex. She stopped on one ad that made it clear what he wanted. He was looking for a college girl, 18-21 who would pose naked for him. No sex. Cindy thought to herself that she had done nearly the same for the boy yesterday, but this ad promised $200 just for posing. Still, she couldn't possibly pose completely nude, could she?

Cindy felt a little aroused again, and also a little dirty. She decided to take a shower and clear her mind, and walked a few feet to the bathroom, closing the door. Cindy felt refreshed by the shower and was determined to find a proper job, but when she opened the bathroom door she saw Barry, the boyfriend of one of her roommates at the kitchen table looking at her computer.

"Hey Cindy" Barry said eyeing her up and down. 

Cindy silently thanked god she had wrapped herself in a towel, despite believing she was alone in the apartment. 

"Didn't mean to startle you...I just got up myself." 

Barry stretched lazily. He had long hair and a beard, and was showing off his skinny, yoga-sculpted body by wearing just shorts, with no shirt at the table. Cindy flushed a little, but forced a smile and started to go to her 'room' .

"I see you've been looking for a nude modeling gig?"

Cindy froze, feeling heat rise to her face. "I...I was just..."

Barry smiled and looked down at Cindy's legs. "You know, I would pay you...you're very beautiful."

Cindy didn't know what to say, she just stood there, wrapped in her towel, dripping a little on the floor. 

Barry continued his push "Really. I mean you're already almost completely naked, and we're both here. I can't pay you $200, but...$100...pose for me for just half an hour?"

Cindy knew she couldn't. She didn't know Barry's girlfriend Anna very well, but it was her roommate and... 

Barry got up from the table and took three steps towards Cindy until his over six foot frame towered above her. He looked down at her cleavage, then into her eyes, then he took out his wallet and pulled out five $20 bills. 

"Come on Cindy. Just you and I. Drop the towel and pose for me."

Cindy tried to say no but the words would not come out. Her throat felt dry and her heart was beating fast. She knew she needed the cash to pay for her phone bill, and if she didn't have a phone she'd never get a job. She shook her head but Barry kept looking right into her eyes, a small smile on his face. 

"$120, Cindy. Just let me take off the towel for you, then you pose for 30 minutes. Deal?"

Cindy felt the same strange mix of fear and arousal she had felt the day before. Almost as though it was out of her control, she raised her arms, rather like an angel. 

"Good girl Cindy" Barry said, then he reached down and gently pulled the wet towel off of her, leaving her completely naked for him. 

Cindy felt cold despite the fact that there was no air conditioning in the apartment. Her nipples were rock hard as Barry surveyed them. He took his time, slowly lowering his gaze down her her pussy. 

Cindy stood there for what seemed like forever as Barry took her in. She could see he was hard through his shorts. 

Finally, Barry placed the $120 on her laptop and said "I'll never regret spending this. Turn for me."

Cindy obediently turned, then without being asked she put her hands on the couch and raised her ass for Barry. Barry stood behind her and said nothing. Cindy felt so naughty just bent over naked like this for a stranger. Somehow this fact that Barry was not taking pictures made her feel even more like a slut. Suddenly she imagined what the scene would look like if one of her roommates came home now.

"Bend over some more Cindy." 

Cindy almost immediately thrust her ass up higher, and was rewarded with a whistle of appreciation. She felt hot, and realized she was quite wet from posing for Barry like this. She realized that he might be able to see this, which somehow made her wetter still. 

Even Cindy's boyfriend had never seen her like this, back home they were usually in the car and rather rushed. Barry seemed to be in no rush at all. She was too shy to look back at Barry now, and she started to squirm, unable to stop herself. Barry murmured appreciatively and Cindy was mortified to feel a trickle go down her leg.

"Cindy you might have the finest ass I have ever seen." Barry said emphatically. "Would you be ok spreading your ass cheeks for me?" 

Cindy wiggled her ass a little and pretended not to hear, not wanting to say no but hoping to avoid the humiliation. "Spread them for me." he said softly.

Cindy put her hear on the couch, reached back and slowly spread her ass cheeks. She knew now that she was completely exposed to a boy she had met only twice before in passing. She knew he could see how excited this made her. 

Cindy heard a grunt and looked back to see Barry stroking his cock, staring right at her asshole, less than a foot from her. She recognized the sound of a man about to cum and she spread her ass cheeks a little wider for his appreciation. Barry shot all over, getting a little on her feet while he did so.

Cindy's Adventures in NYC Ch. 02



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?"




Cindy's Adventures in NYC Ch. 02



Cindy's mouth opened but nothing came out. She was mortified that he knew about what she had done, and now...he expected her to...?

"Just a look Cindy. I can pay $25. I know you need the money, you owe the girls $50."

Cindy was taken aback. She had forgotten that she owed for cable and utilities. She only had $35 to her name, and she needed that for her prepaid phone and a bus pass, not to mention food. She looked at Eric with his pleading eyes. "I...just a look?"

Eric nodded eagerly, and Cindy interjected "I'll need $50."

Eric laughed and noted that he good get a couple of lap dances for that, but agreed to pay if she would show her ass for a full two minutes. He encouraged her to hurry before the girls got back. 

Cindy felt a sense of shame wave over her as she took Eric's $50 and slowly turned around, but she also felt a jolt of excitement at what she was about to do. Cindy slowly turned her back to the two seated boys, bent over and lifted her little dress to reveal the thong panties she wore. She wondered if she would have to remove the panties, but instead felt Barry's hand touch her right ass cheek as he told Eric how it was just as nice as he remembered.

"Yeah," Eric laughed as he ran his hand along Cindy's left ass cheek, "I guess this is the result of all that fresh milk." 

Cindy felt like the two hands on her bottom were shooting heat up her body. Eric continued to run his hand up and down Cindy's ass and was brushing along her labia as he stroked downward. The two of them were chatting about her wonderful her ass was, but now Cindy was doing all she could to stop getting too turned on. She felt her panties getting soaked and prayed that Eric would not notice. She wanted to move away, but knew the time was not up so instead thrust her ass out slightly more, giving her ass to the boys for the remaining time. 

Cindy was suddenly started by Stephanie's voice as she came down the hall towards the apartment. The boys yanked their hands away and Cindy rushed to her room. She was half way through her curtain when the door opened, her bare ass still exposed. Cindy dove on to her bed on the floor, her heart beating fast. She heard the girls talking to Eric and Barry and realized that she must not have been caught. 

Cindy was angry with herself for getting in that situation. She was also exhausted. She took off her dress, then lay in her panties listening to some music. She thought about all the men who had looked at her today, and all the times her ass had been touched. She heard the guys talking just outside and thought about how naughty she had been. Cindy touched herself thinking of their hands on her, and remembering how she had spread her ass cheeks for Barry and made him cum. Cindy brought herself to orgasm, whimpering quietly so they could not hear, then fell asleep with her hand in her panties. It had been quite a first day, and she was blissfully unaware of the adventures that were to come.



Cindy's Adventures in NYC Ch. 03



Standing there in just underwear and heels, Cindy remembered back to the morning of her second day at work. 

Cindy had thought a lot that morning about what she should wear. The men she worked for had all enjoyed the dress she had worn for her first day, but she didn't have any other nice dresses and figured she couldn't wear a dress every day. Cindy knew she had to brighten up the office and look 'playful', but she was still unsure what exactly that meant. She very much wanted to please Ed and the other men. 

She decided to wear an outfit she had received compliments for any time she had worn it. She wore her best jeans, which hugged her body well, showing off her ass nicely. She put on a tight red top, very bright. It emphasized her large breasts, with a deep v-neck. She knew the men enjoyed staring at her tits, as men had since she was 15, so she was sure this would please them.

The stares Cindy received while taking the bus to work reassured her that she had chosen well. She felt a little excited imagining Ed praising her when she arrived. She felt that overall she had done well on her first day and wanted to ensure that she made everyone happy so she could have a strong start to her career.

Cindy wanted to get to the office by 9am, so she walked quickly towards the elevator when she arrived at the building her office was in. Ed was there waiting at the elevator with a gentleman in a suit she had never seen. He greeted her with a booming voice as she arrived. "Hey darling, you excited about Day Two?"

Cindy smiled and assured she was as the elevator arrived. Ed pressed for their floor, the other man for a higher floor.

"So, let me see that outfit of yours." 

Cindy awkwardly stood and pulled her hands away from her side. Ed stared at her cleavage and she could see the stranger doing the same. "Hmmm...can you turn around for me darling?"

Cindy felt rather silly turning around, especially with the other man watching, but of course she did as she was told. 

"You look nice doll." There was a long pause, "...but I think it's best if you stick to skirts."

He turned to the other man "Don't you think Cindy should wear skirts for us?"

The other man agreed emphatically as the elevator stopped. Ed patted Cindy on the ass and said "Why don't you go buy something a little more playful and come on back then?"

As an afterthought Ed handed Cindy $20. The elevator doors shut and Cindy turned around. The stranger was still looking at her, a smirk on his face. He got off on his floor with a leer, and Cindy took the elevator all the way back down to the lobby. 

Cindy was disappointed with herself. She really wanted to please her bosses. Why was she complicating things? When she wore the dress yesterday it was clear they all enjoyed it. 

Cindy walked over to the 'Forever 21' store down the street. The store had just opened so she was the only customer. She looked at the clearance rack since she had only $25, including the money Ed had given her. There were only two skirts close to her size that would fit her budget. One was a mustard color skirt that would go to her knees. She knew this would not be playful enough. The other was a bright purple skirt, that was a size 2. Cindy normally wore a size 4, but thought it might work. It certainly would clash with her top, but it was bright, and quite short. She was sure her bosses would like it. The reduced price was $29.99 but she hoped it was further discounted.

Cindy found a sales assistant (one of only two other people in the store) and asked him what the final price was. He was a weasely looking fellow, a bit shorter than Cindy. He stared at Cindy's tits, then looked at the tag and told her it was $29.99. Cindy nervously said that she only had $25. She asked if they had any skirt for that price and the man told her that everything was on the rack, and besides there would be tax on top of the prices. 

When Cindy looked like she was going to cry, the man added. "Well...if you wanted to give me a quick flash, I could give you an extra markdown."

Cindy was genuinely shocked, "You..you want me to flash you? Here...in the store?!"

"Sure" the man said licking his lips. "Nobody is here, we can go behind this rack."

Cindy looked at him, wondering to herself what kind of city this was. She knew she needed to get a skirt and get to her job. It was only her second day and she was already off to a bad start. She bit her lip and ventured, "Just for a few seconds."

The man nodded vigorously and Cindy followed him behind the rack of hoodies. Cindy took a breath, then lifted her purple top for him, exposing a small red bra she had chosen, and most of her plump breasts.

"No no!" the man said, "your tits, not your bra."

Cindy had expected he might insist. She decided she had best just accept that he had her where he wanted her. Cindy reached down and lifted her bra, exposing her hard pink nipples for the little man. He moved in closer and Cindy allowed him to enjoy a lingering, lustful stare, before lowering her bra and top. 

"Nice." he said simply. "Hey if you let me have a feel I'll give you the dress for free."

Cindy was amazed at how crude the man was. He wanted to feel her up right here in the store? She looked around and saw there was still nobody around. Cindy realized she was actually considering the offer. Of course she couldn't let this stranger feel her tits in public...certainly not for $20. But she did need the money, and she couldn't deny that she was feeling a shiver of excitement about the idea. Only three boys had ever felt her tits.

Cindy stammered that he would have to be quick and again lifted her top and bra, this time moving closer to give the man access. The man took a breast in each hand, then pinched both her nipples. Cindy bit her lip as the man started to stroke her nipples, making them even harder. She shifted her weight and pushed against a hanger. The noise startled her enough that she quickly lowered her top thinking somebody was there. She looked at the man who was now wearing a lustful grin. 

The man took the security tags off the dress and let Cindy leave the store. She felt a bit of the excitement that she had felt when she had exposed herself to other men, but she also felt a little dirty. Why couldn't more men be a gentleman like Ed was?

Cindy ran back to the office lobby and ducked into the restroom, using a stall to try on her new skirt. The skirt was smaller than she had expected. Cindy could barely get the zipper done up. When she came out of the stall and looked in the mirror she saw that the skirt was so tight it actually rose in the back. She would need to be very careful not to bend over or she'd definitely be showing her ass at the office.

When Cindy arrived in the office Tony and James were already there. She felt bad that she was now late, but peaked in Ed's office to see if he was there. She was anxious for his approval. She peeked into his office and heard him beckon her. 

"There you are darling, come on over here."

She walked over to his desk and stopped at his chair. She thought she may have come too close but Ed did not move. 

"Now that's much better doll. Turn for me"

Cindy suppressed a smile as she turned. "Very nice." Ed said as he felt the material on her little skirt. "You will brighten up the office for sure today. Let's go show James."

Ed stood and patted Cindy's bottom, indicating for her to follow him. Cindy kept pace with Ed down the hall, then Ed called out to James. "James, I wanted you to see how nice Cindy made herself up for us!"

James got up from his desk and studied Cindy carefully, towering over her. Finally he walked around her to look from behind. "Very nice Cindy. Rather colorful, but quite attractive."

Cindy looked over her shoulder and thanked James. She didn't move as she wasn't sure if the inspection was over. The two men now talked to each other, rather as if Cindy were not there. Ed explained that Cindy had found it challenging to choose the right outfits for the office. He noted she was very young and needed a lot of direction. Cindy flushed a little at this but remained turned away from the two men. Ed went on to suggest that it might be best if the men in the office chose Cindy's outfits for her. They agreed that this was worth trying and asked Cindy to draw up a schedule for the office. 

Cindy reached over to the desk for a piece of paper and took a pen out of her purse. The men were waiting for her to take notes and with nowhere to sit, she placed the paper on James's desk and indicated she was ready. 

"Put me down first for tomorrow, then James, then Tony. Danny can go next week."

Cindy bent down to make the notes and as she did so, she felt the air conditioned air blow against the bottom of her ass cheeks. She realized that she was showing a little of her ass to the two managers, but there was really nothing she could do about it. 

The men were quiet as she wrote making Cindy feel even more awkward as she imagined they were both noting her exposed bottom. Finally Ed asked her to make a note that the person responsible for Cindy's outfit must buy it for her and have it to her the day before she is to wear it to the office. 

As Cindy wrote this she felt a little ashamed that she was not able to dress herself to their liking, but also felt relief that she could be confident that she would please them. It also made her feel special that they took such an interest in her. 

Cindy showed Ed the schedule she had written and Ed complimented her on the job. He asked her to title it 'Cindy's Work Attire' and to pin it on the wall by her desk. When Cindy pinned it later she felt a little silly having to sit beside a note that outlined which men would be dressing her when, but she told herself this was all part of starting her career.

The rest of the morning was rather uneventful. Cindy answered a few calls. The FedEx guy stayed a while to chat Cindy up and stare at her tits. Cindy tried to be polite without encouraging him.

Tony asked Cindy to get a button on his jacket repaired. As always Tony was brusque with her, giving the jacket and some money with a few words of instruction, telling her the dry cleaner to take it to and asking her to have it back by 3pm. The dry cleaner clearly took note of Cindy's cleavage, even with his wife being a few feet away.

At noon, Ed told Cindy he wanted her to pick up and serve lunch. There was an important client about to arrive and Ed was going to talk business with him over lunch in the Boardroom. Cindy was of course happy to do so, and rushed down to pick up Ed's order at an Italian restaurant down the street. The elevator coming back up was rather crowded, and Cindy felt a man behind pushing against her. She might have minded more if she hadn't been so distracted by the delicious smell of the food she was holding. Cindy had been eating ramen and fast food salads for so long she had forgotten what a real meal was like. 

When Cindy arrived with the food, the guest was already in the Boardroom. Ed introduced her as the "little doll" he had just hired. The guest, Lou Peters, who looked to be over 50 years old. He was in good shape and wore the suit of a wealthy man. Ed explained that he was looking to rent two floors of an office building on the Upper East side. The man took Cindy in slowly and told her she was quite lovely. Cindy blushed a little and began setting out the food and two place settings. The two men watched her, and she was again embarrassed that they could see her ass whenever she bent over the table. She blushed, imagining what this man must think seeing a girl at a professional workplace showing off her bottom like this. When everything was set she thanked them and excused herself, but Lou encouraged her to stay.

"Cindy, don't leave us now, keep me company while Ed blathers on about this building I'm looking at!"

Lou patted the chair beside him. Cindy gave a look to Ed who nodded and gestured for Cindy to sit. Cindy awkwardly sat herself in the big chair beside Lou, which seemed to please him greatly. Cindy was very aware that her bare legs were almost completely presented to the man, who sat less than a foot away. It was clear he was aware as well. Ed and Mr. Peters chatted a while as they ate the meal, when suddenly Lou noted that Cindy didn't have any food. 

"You must try some of this veal Cindy." Lou said, proffered fork in his hand. 

Cindy hesitated for a moment, but she knew it would be impolite to refuse. Besides the veal looked so good. "Thank you Mr. Peters" Cindy said.

She bent forward to bite the veal off his fork, showing him a lot of cleavage while she did so. 

Lou smiled at Cindy knowingly and murmured "That's a good girl." 

Lou proceeded to have Cindy take several bites off his fork. Cindy felt silly at first, but saw that the two men were pleased. She was happy to get such a nice lunch. Cindy was now sitting very close to Lou, her leg touching his as she took a little dessert off his spoon. She listened to the men talk about details around rent and office space, trying to learn about the business, but unable to grasp much. Lou offered her more of his tiramisu and as Cindy bent forward to get it, she felt Mr. Peter's hand slide up her bare leg, resting just below her skirt. 

Cindy's eyes widened as she swallowed the dessert. She knew she shouldn't make a scene, but she thought she should at least move his hand away. The two men carried on their conversation in a jovial way and Lou squeezed Cindy's leg playfully. Cindy was happy to see her boss and his client in such a good mood and decided to just allow Mr. Peters to feel her leg.

As Ed tried to close the deal Cindy felt Mr. Peter's fingers playfully brushing her inner thigh. Cindy felt hot from his touch, and could feel herself moisten. She didn't think she wanted this much older man, but she did enjoy making him happy, which he clearly was. Cindy could see an erection forming a tent in the man's suit pants. 

Suddenly Cindy was jolted from her thoughts. Apparently a deal had been made and the two men rose to shake hands. Ed was clearly excited and Lou had a big smile as he offered his hand to help Cindy out of her chair. When she rose he pulled her into his arms and have her a big hug, thanking her for keeping him company. Cindy could smell a nice cologne on the man as his cock pushed against her. Lou kissed her cheek, then Cindy felt his hand go up the back of her skirt and aggressively squeeze her ass cheek. 

Cindy's first concern was not that a stranger was groping her ass in the office, or even that Ed could clearly see her exposed ass being squeezed by his client. Cindy worried that Mr. Peters might notice the dampness in her panties if he moved his hand ever so slightly. Fortunately Lou moved on, slapped Ed on the back and left the office, promising to sign the papers when they were sent to him. 

Ed was elated . He high-fived Cindy and told her how good she was with Lou. 

"We make a great team darling...I can tell you're going to fit in just fine here!"

Cindy now shared his excitement. She had been determined to make a great impression here and on Day Two is was clear she had. 

"Let's celebrate...we can go shopping the outfit you'll wear tomorrow." Ed suggested with enthusiasm. 

When Ed put his hand on Cindy's ass to guide her to the door, it somehow felt familiar. Cindy was pretty sure this wasn't normal in offices, but she had already established a strong relationship with her boss and certainly didn't want to change that. 

Ed was buzzing as they went down the elevator, which made Cindy glad. When they got to the street, however, Cindy's heart beat a little faster. She realized Ed intended to take her to the same Forever 21 where she had flashed the salesman earlier today. 

Cindy started to suggest somewhere else but Ed was brimming with enthusiasm and didn't seem to be listening. The two of them walked in and of course the same salesman saw Cindy and walked over to greet them. Cindy cringed when she saw he was looking right at her tits.

"Hi guys, what are you up to today? the salesman asked, seemingly genuinely intrigued.

"Well, we need to buy this young lady an outfit." Ed said, still sounding very chipper from his sale. 

The salesman smirked at Cindy and turned to Ed. "Certainly sir. And what kind of outfit were you thinking of?"

Ed explained that he wanted he to look very attractive for the office. The salesman noted that the outfit she had on looked very nice and the two men looked her up and down.

"Agreed" Ed smiled, "perhaps a bit more sophisticated, but still showing those lovely legs!"

"She does have very lovely legs sir." the salesman agreed. I'm not sure we can have her show much more than she is?" 

Cindy shuffled a little while the two men studied her legs. She felt silly listening to the two men talk about her body while she stood there silently, but she understood that she had proven to be incapable of dressing herself properly. 

"Can you pull your skirt up a bit darling?" Ed asked.

Cindy looked down at her skirt. Did he really want her to lift it up. She looked at Ed blankly and saw him looking down at her legs expectantly. She could feel the eyes of the salesman on her as well, but couldn't bring herself to look at him. 

Cindy lifted her skirt just a little and the salesman jumped in "maybe just a little higher?"

Cindy breathed out and lifted her skirt up just a little more. She saw a boy shopping with his girlfriend nearby look over at her as she now had her skirt just barely covering her panties. 

"Turn for us darling." Ed instructed. Cindy felt a familiar mix of humiliation and excitement as she turned slowly. The two men looked at her legs in silent appreciation as Cindy modeled for them. Ed reached over and gently pushed on the top of Cindy's back for her to bend forward. As Cindy did so she felt the air conditioning in the store on her ass cheeks and knew she was showing the two men, and anyone else looking on, much of her bum. 

"That seems about right." Ed said, still talking to the salesman. 

The salesman agreed joyfully, and said he'd be right back. Ed patted Cindy softly on the bottom of her bare ass cheek, an indication that she could stand upright again. Ed's touch felt like a jolt of electricity to Cindy, and she was flushed as she turned back around to face him. 

Ed looked into Cindy's eyes "A pretty girl like you is meant to be shown off and celebrated Cindy. Great to have you on the team."

"Thank you, I'm excited to be here." Cindy said reflectively. She had never thought about part of her job being 'shown off', but if that's where she could add the most value, she wanted to do it well. 

The salesman came back, holding a tiny white skirt. It looked to be a 'youth' sized skirt, and Cindy could see that it was too small for a woman to wear. Before she could object Ed told her to try it on for them. In the changing room, Cindy looked at herself in the mirror, and she could see that the skirt did not fully cover her bottom. Cindy knew this was not appropriate for the office and she started to take it off when she heard Ed's voice calling for her to come out and show them. 

Cindy did not want to disappoint Ed, even though it meant showing him and the little salesman her ass hanging out. She was sure Ed would agree they needed to find another option. Cindy tentatively opened the door and walked over to the two waiting gentleman. Cindy heard the salesman's appreciative whistle and without being told turned to show the two men the back of the dress that did not fully cover her bottom. 

She thought to herself that this salesman had seen her bra, groped her tits, and now seen most of her ass, covered only by her little red panties. She also thought of her boss, who was now enjoying yet another look at her ass, after having seen and handled it several times today. She felt a tingle rush through her body. 




Cindy's Adventures in NYC Ch. 03



"We'll take it." Ed stated happily. He then stage whispered to Cindy, "You may want to just change into that one when you arrive tomorrow."

Cindy knew she should object, but she accepted that she was not the one making the rules. Her boss enjoyed seeing her body and she very much wanted to please him. If that meant she had to prance around the office with her ass half exposed...well, at least she would be successful in launching here career here in the big city. 

Ed bought the dress from the salesman, who winked crudely at Cindy before they left. Ed placed his hand on Cindy's ass to guide her out of the store, but unlike the other times he did not remove it when she took his lead. Instead he kept his big hand on her bottom as they walked down the street back to the office. Cindy felt very secure in his acceptance, but also self-conscious. What must people think seeing a man well over twice Cindy's age with his hand stroking her bottom through her tight skirt?

It was almost 3:30 when they got back. Ed told Cindy she had been such a good office girl that she should leave at 4pm and enjoy the rest of the day. He gave Cindy's ass a big squeeze then finally removed it. 

Cindy sat alone at her receptionist deck with a sigh of wonder. It really is funny how things can work out, she thought. Just a week ago she was thinking of going back home, and now she was on her way to making it in New York City.

At 3:50 Cindy was sitting alone, wondering how to spend the rest of the afternoon, when Tony came by. Tony never talked to her so she was a little startled when he spoke. 

"Cindy, where's my jacket?!"

Cindy's heart leapt, as she realized she had forgotten to pick it up from the dry cleaner. She started to explain that she had been called into a meeting, Ed had made a sale and... Ed cut her off before she could finish the story.

"Come into my office Cindy."

Cindy followed Tony down the hall, having to hurry in her heels and tight skirt to keep up with him.

"Shut the door" he said simply as she entered his office behind him. 

Tony sat on the edge of his desk and Cindy stood in front of him, head hung slightly. 

"What time did I tell you to have the jacket back to me?"

"Ummm...3pm...sorry, I can get it..."

"Cindy, it's just your second day and you have already shown I can't count on you. You know I can't accept this right?"

Cindy's eyes widened and her heart beat fast. Was she going to lose this job? She had already done so much to please everyone. 

"I know you have everyone panting after you with your ripe tits and your little skirts," Tony continued, "but I expect you to do your job."

Cindy was taken aback by how direct Tony was. Tony moved over to the couch in his office and sat down, motioning for Cindy to follow.

"Bend over my lap Cindy."

Cindy couldn't believe what she was hearing. Tony wanted to spank her, right here in the office? "Sir, I..."

"Now Cindy." Tony said firmly, pointing at his lap. 

Cindy put a hand on the couch and awkwardly lay over Tony's lap. To her further shame Cindy felt herself moisten as she felt her body press against Tony and submitted herself to him. 

"Good girl." Tony said as he stroked her bare leg lightly. "Now lower your panties for me."

Cindy felt like she was having an out of body experience. Surely this couldn't be happening? She felt her hands reach up and grab the band of her red panties. She slowly lowered them for Tony. Cindy made no effort to maintain modesty, her ass now fully exposed for her boss, her panties lowered to her knees. Cindy wriggled a little as she felt wetness dripping down her inner thigh. She realized she might stain Tony's nice pants and wondered what he would do.

Tony stroked her ass slowly, making Cindy feel comforted. "Now Cindy, I know you won't be perfect, but I expect you to accept that there are repercussions for errors. Our last receptionist couldn't handle that"

Cindy could barely follow what Tony was saying, she was so focused on his hand running along her ass cheek, a finger slowly following her ass crack. 

Suddenly Tony raised his hand and landed it hard on Cindy's left ass cheek. The noise and the pain startled Cindy, but she felt herself raise her bottom is response. Tony landed another on the same cheek the another. Cindy squirmed but kept her bottom raised. She had not been so wet since she had been with her boyfriend...or maybe never?

Tony's hand now slapped her right ass cheek. Cindy momentarily thought about the Ed and James in the office who must be able to hear her being punished. The thought quickly passed as Tony landed several more swats. She felt heat emanating from the stings on her ass and knew she must be very red. She wriggled again and felt how hard Tony was underneath her. This somehow relieved her, and she raised her ass ever higher for her boss, despite the pain.

Tony did not spank Cindy again, but instead inserted two fingers into her pussy. Cindy pushed back into his fingers eagerly. Cindy thought about what a slut she was for so desperately wanting his fingers deeper in her, but she couldn't seem to help herself. She knew she was dripping all over Tony. 

"Mmm...that's what I like Cindy." 

Those words somehow overcame Cindy and she started to cum. She felt herself tighten around Tony's fingers, and whimpered like a little girl as he stroked inside her. Cindy rode Tony's fingers until her orgasm stopped, then she slumped over Tony exhausted. 

Tony removed his fingers and gave Cindy's bottom a final smack. He told he hoped she had learnt her lesson and told her she had better have his jacket hanging on his door before he came in tomorrow morning. 

When Cindy stood up she was unsteady, feeling like she was in a daze. Tony told her to leave her panties off and she let them fall to the floor without even thinking. Cindy smoothed her skirt, apologized again to Tony and left his office. She proceeded to the elevator and as she went down she could not believe what had just happened. Had she really been bent over her boss' lap, her bare ass raised to receive his spankings? Had he really brought her to orgasm with only two fingers? Had the others in the office heard it all? With every thought she felt a new wave of shame, but also waves of excitement. She knew this had gone too far, that this was not at all appropriate for the office...and yet...

Cindy felt the elevator stopping and realized with horror that she had a finger inside herself. She yanked it away as the doors opened. Yes, that had really happened. Her ass was sore from the hard slaps she had received. As she walked out to the street Cindy felt like she was naked to all onlookers. She felt a breeze up her skirt, cooling her burning ass and making her very conscious that she still had her own wetness on her leg. Cindy could not bring herself to look any passerby in the eye as she waited for her bus, anxious to get home and have some alone time in her little room. She didn't know how she would bring herself to go in the office tomorrow after what had happened...but she was already looking forward to Day 3. 



Cindy's Adventures in NYC Ch. 04



The day after one of her bosses had spanked and penetrated her with his fingers, Cindy got ready for work with an intense mix of fear and excitement. She showered herself thoroughly, having learnt that she may find herself in rather intimate situations in the office. When she finished and opened the bathroom door she found her roommate Stephanie was a little pissed about how long she had taken in the bathroom. 

Cindy got herself dressed behind the curtain of her little 'bedroom'. She put on a tight top that had a generous amount of cleavage. Her boss Ed had not chosen a top for her, just a far too small skirt which Cindy packed into her purse. She would have to change into it at the office as if she wore it to work she might be arrested before she completed the trip there. Cindy chose a pair of white panties with a bit of frill on them. It struck her as strange that she was worried about what panties to wear, but she knew that pretty much everyone in the office would see them given how short her skirt was. The panties were sexy, but covered at least half her ass. A good compromise she thought to herself, as she knew a key part of her job was the be 'shown off'. Cindy put on a pair of jeans, then chose heels that would go with the skirt later. 

As usual Cindy was a bit tight on time so she rushed out and caught the bus. She was lucky to get a seat and on the way in Cindy smirked to herself a little, wondering what the others on the bus would think if they knew the sexy outfit she would soon be wearing at her work. Cindy then frowned as she imagined what her old boyfriend back home would think. He would not approve at all. 

Cindy thought more and realized that when Tony had put two fingers inside her yesterday he was only the second man to have done so. Well, perhaps the only real man, her boyfriend had been the other. Cindy remembered how she had ridden Tony's fingers and made herself cum. She felt her face redden as she sat on the bus feeling aroused and ashamed. What would Tony say or do now that he knew Cindy would not protest when he told her to bend over his lap? Now that he knew she was a slutty office worker who might let him do whatever he pleased? Would she really let him do anything?

Cindy broke away from her reverie when she realized the bus was approaching her stop. She squeezed through the crowd and made her way off. Cindy walked into the lobby and as she got on the elevator she checked her watch and saw that she was good on time. She rode up the elevator alone and felt her heart beat a little faster with the anticipation of the unknown. 

When the elevator got to her floor, Cindy was grateful she didn't see anyone, and ducked into the restroom. Cindy didn't bother going to a stall. She knew that there were only men in the office, so she simply peeled off her jeans and put on her skirt. She struggled to put on the small white skirt, then looked in the mirror and was shocked anew at just how short it was. Could she really spend the day walking around in this little outfit? She was showing so much bare leg it looked like she was dressed for the beach. Cindy turned around, knowing what she would see but she still gasped as she saw the bottom of both her ass cheeks just peeking out under the skirt. Cindy bent forward just a little and confirmed that she would basically be mooning if at any time she had to bend forward for anything. 

Cindy folded her jeans and put them in her bag. It was time for work and she knew she couldn't be late. When Cindy walked out of the bathroom she saw Danny and Eddie (the boss' son) standing at the reception desk, looking as though they had been waiting for her. 

"Oh!", Cindy started, "I thought I was..."

"Cindy!" Danny broke in happily. "Look at you our eager sales girl! I heard you helped to land Old Man Peters!"

Cindy's thoughts flashed to Mr. Peters fingers running along her inner thigh but she saw Danny approaching her with a big smile, his hands stretched wide.

Danny put his arms around Cindy. A small man, his face just reached above her breasts as he squeezed her close. Danny's hand brushed against Cindy's ass then he gave Cindy's left ass cheek a firm squeeze. 

"Well done Cindy." he send as he took a step back. "And look at you! Dressed for success! Turn around?"

Danny had asked it as a friendly question, but Cindy knew it was expected of her. She turned slowly and knew she was already showing two colleagues some of her ass, only minutes into the day. 

Danny whistled and told Eddie to come closer for a look. Cindy started to turn but Danny put a hand on her back indicating she should stay. At that moment Ed walked in to see Cindy facing the entrance, while his son and Danny both admired her backside. 

"Good morning doll!" Ed boomed with his drawl. "I see you wore the little outfit for me. Very nice! Junior, Danny what do you think?"

The two men murmured their approval as Ed came over to give Cindy a hug. Ed lifted her a little as he squeezed her, his hand familiarly squeezing her bottom. Cindy was used to Ed's hand on her ass by now but she did wonder what message this might send to Danny and Eddie about how to treat her. Still, they all sure seemed to appreciate her which made Cindy feel special.

Cindy could tell that Ed's grope had caused her panties to ride up on one and expose one ass cheek, but she didn't want to draw more attention by reaching back and fixing it. The three men all gave Cindy another look up and down, as Cindy shifted from heel to heel. Finally Ed took Danny into his office for a meeting.

Now alone with the hot new receptionist, Eddie seemed rather unsure of himself and stuttered a little "You...you do look very nice today Cindy."

"Thank you Eddie." Cindy replied as she settled into her desk, but Eddie was already walking away down the hall. 

The rest of the morning went by rather uneventfully. Cindy made a quick change into her jeans when she ran down to the dry cleaner's to get Tony's jacket. She hurried back, hung the jacket up in Tony's office, then made a quick change back into her tiny skirt. Cindy realized that she was disappointed that nobody seemed to take notice of her coming or going. She wondered why she was so anxious for the attention.

Tony came off the elevator and walked into the office. Cindy felt herself flush. What must he think of her after the incident in his office? Tony did not even acknowledge her when he hurried by to his office, which somehow made Cindy feel hurt. Even later when he walked by on his way to Ed's office he didn't so much as glance at Cindy. Had she disappointed him somehow? She had taken her punishment without protest.

Cindy fidgeted at her desk, wondering what everyone was meeting about. She wished that she was part of the meetings. She had been feeling very good about her contributions, but started to feel insecure sitting alone now, the phone not ringing. 

When the Fedex guy came by, Cindy found that she enjoyed how attentive he was with her. She even got up from her desk to sort through the delivery and when she did she couldn't help but enjoy hearing the man gasp aloud upon seeing Cindy's little skirt. Cindy could feel his eyes on her legs as she placed a package in Ed's mailbox slot. 

Danny came out of Ed's office and asked her to go fetch some sandwiches for them. He handed her $30 and told her to choose what she though they'd like. Danny then reached over and gave her ass a generous squeeze. Cindy was glad to be needed, but realized that the Fedex guy now knew that the men in the office had no hesitation to fondle her as they pleased. The delivery man gave Cindy a wink as he left and took the elevator down. Cindy wanted to change into her jeans but Danny looked at her rather impatiently and she decided she best get going for the food run. Cindy took the next elevator down and felt lucky when the elevator arrived with nobody on it. 

When Cindy arrived at lobby level, she knew the eyes of the security guards she passed every day were locked in on her ass cheeks as they swayed on her way to the street. One had complimented her earlier with a leer. Cindy ran across to the sandwich shop and lined up with the crowd. She could hear the whispers behind her, but she closed her eyes and tried to shut them out. It was almost like a nightmare of being naked in public, which of course she was very close to living out.

Cindy was excited to bring the sandwiches up to the guys and was pleased when they all looked up at her as she walked into the office. Tony was there and Cindy brought him a sandwich and drink first, but he barely looked her way. She moved on to Ed, and as she bent over to serve him his lunch, realized that she was exposing pretty much all of her panty covered ass to Danny. As she felt his hand pat her ass cheek she guiltily wondered if she had known exactly what she was doing when she bent over with her back turned to him. Almost out of obligation she offered Ed the same view as she bent forward to serve Danny. As she had come to expect she felt Ed's hand pat her ass cheek reassuringly. She took a little extra time arranging Danny's plate as she looked over to see if Tony was also admiring her. He was not, instead he was writing something into his phone. 

Cindy asked if there was anything else she could do for them and Ed suggested that they should all go out to celebrate her help in landing the Peters business after work, especially since Cindy was all dressed up. Cindy was over the moon with excitement. She could barely focus on her work as she sat alone at her receptionist desk, eating the salad she had got for herself. 

Suddenly she choked a little, realizing that Ed expected her to wear her tiny skirt to a bar as the team went out on the town. She knew Ed would be extremely disappointed if she changed into her jeans. Part of her wanted to run away and avoid the humiliation of having everyone stare at the slutty girl who was drinking with all the men, but part of her imagined how important she would feel to be the center of attention like that. She had to remember that just a week ago she had no career at all. 

Shortly after 5pm, Ed gathered the troops and said it was time to head out. Ed held out his arm for Cindy to take and they led the way to the elevator where Eddie and Danny joined them. Cindy was disappointed that Tony did not seem to be coming, but she did not ask about him. 

As the elevator descended Ed and Danny exchanged ideas about where to go. Ed's hand stroked Cindy's ass almost absent mindedly but with the sustained touching Cindy did feel her panties moisten a little. 

They agreed to make the easy choice and start at the swank pub next to the office. It was already crowded with office workers enjoying happy hour. Cindy squeezed past the crowd following Ed and noticed the men near the bar made little effort to give her room. Ed found a table and the four colleagues sat down, sinking into the plush chairs. They quickly hailed a waitress and placed orders. Cindy couldn't help but feel a little jealous when Ed called the waitress 'doll' and when she saw Danny check the server out while she walked away. 

When the drinks were served, however, Ed immediately made a toast to their new 'rainmaker' and all the men cheered for Cindy's early contribution. Ed bent forward and gave Cindy a congratulatory kiss on her lips, then Danny quickly followed with a slightly longer kiss. Eddie hesitated but followed suit with a kiss on her cheek. Cindy felt a little disdain for Eddie's awkwardness and wished he could be more of a man. 

Eddie's father then seemed to 'claim' Cindy as his hand stroked her bare leg while he drank his whiskey. Cindy made no attempt to resist this, but did try to keep her legs closed so as not to show Danny and anyone else looking too much of her white panties. She quickly realized that despite her efforts there she could not help but expose herself given such a short skirt and told herself not to be too uptight as she quickly finished her drink. 

Everyone seemed in very good spirits as Ed ordered a round of tequilas shots for the group. Danny suggested they make them body shots when the drinks arrived. Cindy didn't know what these were but Danny explained that it involved licking salt off of another person's body, drinking the shot, then taking a lime from their mouth. 

Danny told Cindy she could go first, then put salt on his forearm, and a lime slice in his mouth. Cindy hesitated, but saw Ed watching her expectantly. She didn't want to make Ed happy, and certainly didn't want to make Danny look foolish so she gingerly ran her tongue along his arm to get some salt, drank down the tequila, then bent across to take the lime from Danny's mouth. She found it took some doing to get the lime. As she fumbled with her mouth on Danny's Cindy knew she was showing much of the bar her ass. She was not surprised to feel Ed's hand on one cheek of her bottom as she did this, but was a little alarmed when she could feel he had pushed her panties up on one side so that they were riding up her ass crack. She almost had the lime when Eddie surprised her by giving her other ass cheek a big squeeze. Cindy could hear the lecherous cheers from the group of men behind them and flushed brightly from the alcohol, exertion and embarrassment. 

Cindy managed to pry the lime from Danny and quickly sat down. She wondered if they might get kicked out for the show they had put on, and felt nervous that she was too young to be at the bar. When she looked around, however, she just saw her colleagues laughing and cheering her dramatic body shot. Cindy smiled and relaxed a bit. She had not often had alcohol and could already feel the effects of the two drinks in just half an hour. She also felt aroused from the pseudo kiss, the hands on her body and all the attention, but tried to push those feelings back inside.

Danny said he was going next and Cindy then realized that the remaining body shots would all be off of her body. Danny dabbed some water on Cindy's neck the salted it generously. He placed a lime in her mouth then quickly dove in to get the salt. Danny greedily lapped up the salt while Ed laughed and Eddie stared, then Danny downed the tequila in a gulp and bent forward for the lime. Danny spent more time than he needed getting the lime which Cindy made it easily available, then finally sat down, content.

Eddie was next. He salted Cindy's knee clumsily as Cindy put another lime in her mouth. Eddie licked Cindy's knee, looking right up her skirt while doing so, then struggled with his drink, leaving half of it. Eddie choked back the remaining tequila, then finally he went for the lime. Cindy tried to pass it to him but Eddie fumbled it from his mouth. Eddie picked the lime off of Cindy's leg and put it in his mouth. 

Ed was last to go and Cindy felt a tingle of anticipation. She looked at Ed and saw the 45 year old man that he was, but somehow...she felt attracted to him? Ed looked Cindy in the eye as he salted high on her leg. He then held a lime slice for Cindy to take, and she found herself bending forward to take it from his hand. Ed then bent down into Cindy's lap and licked the salt from her leg. Cindy felt hot all over as she looked down at her boss licking her thigh.

Ed got up and in one motion downed his shot, turning the empty glass over on the table. He then leaned in to Cindy who sat motionless beside him. Ed put his arm around Cindy, grabbed her hair a little and pulled her towards him. To anyone looking on it seemed that Cindy was making out with her boss as he slowly received the lime from her lips. 

The group cheered again, and Cindy found herself panting a little. She saw that Danny had ordered another round. Cindy felt caught between the desire to slow everything down and to completely give herself to the excitement of the night. She really felt like she was part of the team now.

Cindy's colleagues continued to shower her with attention. Soon Cindy found herself in Ed's lap, his big arm wrapped around her holding her close. Ed nuzzled into Cindy and kissed her ear while his hand brushed her tit. 

Cindy's feet were bare, in Danny's lap while he was giving her a foot rub. She realized her white panties were pretty much fully exposed to Danny and anyone behind him. Cindy squirmed and felt that Ed's firm erection poking into her. She was worried where this was all leading when she felt the phone in Ed's lap vibrating. 

Ed took the call with a few grunts then informed the group that the old lady needed him at home. He lifted Cindy off his lap, threw some money on the table and told Eddie to come with him. Ed gave Cindy a kiss goodnight thanking her again. He started to leave with his done, then looked back, paused, and told Danny he had better head out as well. Danny looked miffed but he finished his drink and got up. Danny also kissed Cindy good night, kneading her bum aggressively while he did so. He looked over at Ed and realized that Ed was waiting for him, so he followed him out of the bar with a lingering look back at Cindy. 

Cindy stood alone, her head spinning a little. She wondered what might have happened if not for that phone call. She didn't want to earn a reputation in the office, but it seemed it might be too late to avoid that. Cindy decided to go the restroom and collect herself before she left. As she approached the ladies room, a little unsteady in her heels, Cindy was suddenly stopped by a dainty hand around her waist.

"Cindy!" she heard as she turned and Cindy saw her roommate Stephanie looking rather pretty in a red dress. 

"And here we thought you were a good girl from the Mid-West", Stephanie mocked lightly as she looked down at Cindy's tiny skirt. "That was quite a show you were putting on."

Cindy's heart sank and her mind raced. Had Stephanie seen everything? Even if she just saw Cindy sitting in a much older man's lap, her panties exposed for the bar to see it was rather mortifying. 

"I want you to meet Keshon, he's an old boyfriend in town from school." Cindy looked away from Stephanie and up at the man beside her. He was tall, black, and well dressed with grey eyes behind his glasses. Keshon had a smile that drew Cindy in as he looked down at her. 

"I was going to be Keshon's wing man tonight, but it looks like you need help getting home!"

Cindy realized that she was indeed a little dizzy from the drinking and tried to clear her mind. 

"Let's get a cab. Keshon can drop us on his way." 

Keshon led Cindy out of the bar, holding her hand. Stephanie followed and took Cindy's arm. Cindy was grateful to have friends in New York, especially since Stephanie and her other roommate had not seemed all that friendly since she had moved in. Keshon hailed a cab with one hand while keeping Cindy's hand in his other. He seemed quite gallant as he opened the cab door. Stephanie slid in then Keshon helped Cindy in the taxi before joining them. Stephanie was telling Keshon about Cindy and how she was new to the city and had this new job and how she apparently had to wear these super-sexy outfits to work every day. It seemed to Cindy that Stephanie was talking a bit too fast to follow everything so Cindy let the words roll over her a little. 

She felt Stephanie's hand run along her left leg as she told Keshon how Cindy was only 18 and had only had one boyfriend. Keshon then ran his hand oalong Cindy's right leg. Cindy was very aroused but also a little sleepy as she looked into Keshon's eyes, then out at the passing lights of the city. Stephanie was telling Cindy that she was just Keshon's type and told Keshon to show Cindy how sexy he thought she was. Cindy turned to Keshon and saw he had pulled his cock out. It was larger than the very few cocks she had seen in her life, and it was hard as a rock. 

Cindy instinctively moved away a little but Stephanie pushed her gently back towards Keshon. Cindy heard Stephanie telling her how nice Keshon had been to take her home and pay for the cab and didn't she want to help him out? She promised she would not tell the anyone else what a slutty girl Cindy had been at the bar with her co-workers. Keshon took Cindy's hand and wrapped it around his cock. Cindy could feel it throbbing in her little fingers. She then felt Stephanie guiding her head down towards Keshon's lap and realized that Stephanie expected her to give Keshon a blow job. Cindy flashed back to the only man she had ever given blow jobs to, her journalism teacher in her final year of high school. Her boyfriend never knew about that...nobody did. 




Cindy's Adventures in NYC Ch. 04



Cindy didn't feel like she decided to do it, but she found her mouth wrapped around Keshon's cock, his hand on her neck as he moaned. She bobbed hear head up and down and wondered what the taxi driver must be thinking. After less than a minute she realized that Keshon was already going to cum. Cindy knew she would have to swallow it to prevent a mess in the taxi, just as her teacher had taught her to do in the back of his car. Suddenly she felt Keshon's warm, salty liquid explode in her mouth. She choked a little as she tried to swallow it all, and could feel a little dribble down her chin. Stephanie stroked her back reassuringly. When Keshon was finished, Cindy sat up and let Stephanie clean her up a little. Cindy realized her skirt was hiked up such that it appeared she was sitting in her panties, but she was too dazed to do anything about it. Soon the taxi pulled up to the apartment and Stephanie and Cindy both thanked Keshon for the ride with a kiss. 

Stephanie helped Cindy up to their apartment, and after a quick shower, Cindy flopped on the bed in her little room. She could barely absorb everything that had happened on her third day of work. Cindy dozed off remembering the outfit she had to wear for the next day. Danny had picked a sexy maid outfit for her which he had left for her at the office.



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.




Cindy's Adventures in NYC Ch. 05



"Cindy, you must have done a helluva cleaning job. Wei Chuan just called and confirmed the deal."

Cindy felt elated as she walked into James big arms.

"Come on little one" James said patting her bottom tenderly, "we're going out to celebrate!"



Cindy's Adventures in NYC Ch. 06



Cindy was about to walk into a room of strangers wearing just a thong and high heels. Before she arrived in NYC Cindy had had only one boyfriend and was quite naive. So much had changed in such a short time. Cindy's thoughts continued to drift back to her first week at the office. It was a week when she took a big leap forward in her career, a week that had changed her life forever.

When Cindy woke up for her 5th day of work, she was a bit overwhelmed by all that had happened over the previous four days. Her mind raced as she remembered how nervous she was on her first day, how she learned she would have to dress in very sexy outfits at work. She thought about how the men at the office had all seen so much of her body, how at various times had their hands all over her, and how she had kissed most of them. She thought of Tony, one of her bosses, who was very strict with her, and who had penetrated Cindy with his fingers on two occasions. Cindy was very wet as she lay in bed with these thoughts and she shuddered with anticipation at the thought of having to see Tony again that morning before the others arrived.

Finally Cindy thought of the previous day, when she had landed a new account by pleasing a new client in his office. Cindy felt a bit of shame as she remembered having the man's small cock in her mouth, but quickly brightened as she remembered how pleased her colleague James was with her. The two of them had such a great time at dinner when James had taken her out to celebrate at a very nice steakhouse. The restaurant, where James dined often, had served her lots of wine even though she was not old enough to drink. The waiter had been very impressed with her little maid outfit. Finally, after dinner James had driven her to a quiet spot so they could be alone. He had her remove her outfit in the car, then fucked her from behind while she knelt on all fours for him. 

Until last night, Cindy had only fucked one other man, her boyfriend back home. Although she had loved her boyfriend, she knew now he was an inferior lover. James had known just what to do to make her feel good. She loved feeling his big hands firmly on her hips as he thrust in and out of her. Before he left to return home to his wife, James had told her how beautiful she was. Cindy agreed that this should be their secret. 

Cindy realized she had been daydreaming too long, and jumped out of bed and ran towards the bathroom for a shower. Her roommate Stephanie had seen her run out of her room and catcalled with questions abut where she had been last night. Cindy was embarrassed. She told Stephanie she was in a hurry, but Stephanie pushed for details. Cindy suggested she could buy Stephanie lunch since it was a half day (summer Friday) at the office. They agreed Stephanie would come by and they would head out then.

Cindy sprinted from the bus to work and arrived just before 8am. She knew Tony would not tolerate her being late. Cindy grabbed the outfit that had been chosen for her today. When Cindy had been told she would have to dress like a Hooters waitress on Friday she had almost protested, especially since the outfit did not include the stockings that all the Hooters girls wore. She had thought better of it, however, when she remembered that a key part of her role was to brighten the office. Cindy knew such an outfit was not normally appropriate for an office, but she had to follow the rules of this office while she got her career going. 

Presently Cindy rushed into Tony's office. He was sitting at his desk, wearing a blue suit. Tony was the only person at the office who insisted on wearing suits. Tony gave Cindy a condescending look. 

"Perhaps you should knock first Cindy?"

Cindy laughed nervously, then saw that Tony was serious. She meekly went back to the door and knocked. 

"Come in Cindy." Tony said seriously. 

Cindy walked over to the desk.

"So...tell me what you came here for Cindy." Tony said looking her in the eyes.

"I...ummm...well you told me I should...to change her in the morning?" Cindy was genuinely confused.

Tony said nothing and Cindy nervously filled the silence. "So...I came here to change for you? I mean...into this outfit?"

Tony continued to look at her and Cindy felt even more awkward. "...or...whatever you tell me?"

Tony smiled a bit at that. "Good girl. You may change for me."

Cindy thanked Tony, and as she did so she realized she was thanking her boss for being allowed to strip for him. She pulled off her shirt and pulled down her pants quickly so that she was standing in front of Tony in just a bra and panties. Cindy watched Tony carefully as he took her body in, trying hard to ensure she was doing as he wished.

Tony nodded slightly and Cindy took her Hooters shirt and pulled it over her head. It was extremely tight and she had a little difficulty getting it over her tits. When she did Tony spoke quietly, "The bra doesn't work with that, you'll have to do without."

Cindy almost let out a sigh as she realized he was telling her she'd have to go bra-less at the office all day in this tight white shirt. She did as she was told though, lifting the shirt and removing the bra. Her pink nipples, currently very erect, were clearly visible through the shirt now, and Cindy shivered with the idea that she would be exposing them to all her colleagues throughout the day. 

Cindy started to put the shorts on but even before she pulled them up she realized there was a problem. The shorts were so tiny that he panties were going to bunch up or show through them. Cindy chastised herself for not wearing a thong. She had meant to buy thongs given the office attire she was expected to wear, but she had been so darn busy. 

Cindy pulled the shorts up and tried to make it work, but she knew it wasn't going to.

"I...ummm...don't think I can wear the panties under these" Cindy said softly. 

Tony nodded the slightest encouragement for Cindy's proactivity, and then watched as Cindy struggled to keep her balance while taking the shorts back off. Cindy took a breath in before removing her panties as well. She wasn't sure she would ever get used to being naked in front of her fully clothed boss like this. 

"You look so good like that Cindy. Perhaps one day they will decide you don't need an outfit at all." 

Cindy blushed on top of her existing blush. She paused before putting the shorts on as she could see Tony was enjoying taking her in. Finally she decided it would be ok to put the shorts on. She could feel how wet she was and knew Tony could see her pussy lips part as she put them over one leg, then the other. Cindy wondered if Tony would finger her again today. So far he had barely moved, he just watched her intently and impassively. 

"Turn around for me." Tony said calmly after Cindy had managed to put the shorts on. They were so tiny Cindy wondered if her cameltoe would be visible for everyone. She knew her ass was mostly exposed as she presented it to her boss.

"Oh, they are going to love you today in this Cindy." Tony said as he stroked her ass cheek. Cindy shook with anticipation as she felt her boss' hand on her. 

"Why don't you..." Tony was interrupted by a quick knock on the office door, then the door swung open.

"Tony!" a well dressed man Cindy have never seen exclaimed. "Nobody was her so I let myself in. I see you have your hands full."

Tony's hands were still on Cindy's bottom. Cindy reflexively pulled away and crossed her arms over her chest.

"Ben, you're early." Tony said. "This is Cindy."

Ben put his hand out and Cindy shook it awkwardly. 

"Nice to meet you doll. Bit early for wings." 

Cindy stared blankly at Ben. He was older than Tony but tall, fit and attractive. He smirked at her with confidence. Cindy noticed Ben was looking at her tits and finally realized he was referring to her Hooters outfit. She laughed nervously at his joke.

"Cindy, I'll need you to step out so Ben and I can meet, but first why don't you give him a proper hug. I heard you can be quite affectionate."

Cindy wasn't sure what exactly Tony had 'heard', but she saw Ben smiling and waiting for a hug and obediently fell into his arms. The man who had known her for all of 60 seconds proceeded to pull her close and help himself to grope the same ass cheeks he saw Tony stroking moments ago. Cindy could feel Ben's hardness push against her, and impulsively pushed herself against him. She which was already very wet and felt confused by how fast things were happening. Cindy buried her face in the man's chest as she tried to shake the thoughts in her head. 

Ben seemed to take Cindy's reactions as an invitation. He roughly put one big hand down her shorts and took all of one ass cheek in it. Cindy yelped involuntarily. She wanted to pull away immediately, but a small part of her was anxious to see what would happen next so she stayed pushed against him. Suddenly they all heard Ed whistling in the hallway. The door was shut but Cindy's heart beat fast, as if she might be caught doing something wrong. 

"Ben, I think that's enough affection for you!" Tony said, more animated than usual. 

Ben released Cindy reluctantly and Tony told her she should get to work. Cindy scrambled to gather her clothes and picked up her shoes. She realized her shorts were still lowered and awkwardly reached back to pull them off before she thanked Tony and Ben and left. 

Cindy walked barefoot towards her cubicle, but Ed saw her before she got there. 

"Good morning darling, you're in a bit early!"

Cindy stammered a little and could feel her face flush. 

"Wow, you look very pretty in that Cindy!" Ed said while eyeing her up and down. Aren't we lucky to have a girl like you working for us?"

"Thank you Ed", Cindy said gratefully. She added hesitantly, "I...ummm...still have to get used to these outfits." 

"Aww, you look great in it darling. You might want to wear shoes though!"

Cindy blushed brighter as Ed continued. "You really are a doll. Cindy, would you mind helping out Junior when he gets in?"

"Of course" Cindy answered, eager as always to please. "What does he need?"

"He needs to learn about how to treat a woman!" Ed exclaimed. "Why don't both of you drop by my office when he gets in?"

Ed didn't wait for an answer, he simply patted Cindy on her bum and walked away to his office. 

Cindy finally got to her cubicle and caught her breath. The day was off to another adventurous start she thought to herself. Although she has dressed in some pretty revealing outfits since joining the company Monday, Cindy felt even more naked today as she looked down and saw her nipples protruding through her tight t shirt and her bare legs. Cindy closed her eyes and enjoyed the silence, and tried to remember the meditation she had once learned in yoga class. Some minutes passed but she could not focus. Cindy realized she was still barefoot so she put her sneakers on, then bent over to put her clothes away in a drawer.

Cindy heard a whistle, then a "Wow!"

She turned her head and saw Danny walking in, looking right at her ass, taking a picture with his phone. Cindy realized she was exposing most of her ass cheeks in the tiny orange shorts as she bent over. She wondered if he could see she wasn't wearing panties. God, she was wet. She would have to be more careful today.

"Give me a hug little one." Danny said as Cindy stood up. 

Cindy didn't hesitate. In her fifth day she had a pretty good idea of the expectations in the office. She walked over and embraced Danny. Although he had called her little, she was actually taller than his five feet of height and Danny's head rested on the top of her tits when she held him. Cindy allowed him to grope both her ass cheeks as he told her how sexy she looked. 

"Cindy, you're so sweet, I wish..."

Danny was interrupted by Ed Jr. arriving. Ed looked rather disheveled in a sports jacket too big for him. 

"Morning Danny, morning Cindy."

He looked at Cindy and began to stammer as he checked out her legs and saw Danny's hand on her bottom.

"I...ummm..."

"Oh, Ed, your father wants to see you. Us actually."

Ed looked concerned, Danny looked disappointed. Ed followed Cindy down the hall to his father's office rather like a child going to see the principal. 

"Junior! Glad you could make it in boy!"

Ed Junior mumbled something Cindy couldn't understand and shook his father's hand. Ed tousled his 18 year old son's hair. 

"This boy Cindy...he is all his mama's!"

Cindy was quiet, unsure what to say. 

"He hasn't had a date for months, he has no way with the ladies" Ed said with some derision in his voice. He brightened, "Junior, Cindy has agreed to help you out. Lucky you, right?"

Father and son both eyed Cindy up and down. Cindy shuffled her feet as she stood before him in her tiny shorts and tight t shirt. The boy nodded as he stared at Cindy's tits longingly. 

Cindy felt herself getting wet again. She didn't want either of these men...but there was something about the way they were looking that excited her. She knew that all the men in the office enjoyed seeing her in the little outfits, but it occurred to her that they all...wanted her. They were experienced businessmen, but she realized that they were probably fantasizing about her. Cindy was glad she had something that would help her boost her career. Her thoughts went to last night in James' car, but she felt herself getting wetter and tried to stop the thoughts. She realized that while she had been daydreaming she had been asked a question by Ed and tried to replay it in her head. She knew he was waiting for an answer so she smiled and nodded.

"Good...thank you Cindy. OK Junior, show her how you would kiss her."

Cindy was a little surprised, but she let Junior clumsily and tentatively take her in his arms and push his lips against hers. Ed Junior did not grope her ass, but he was a poor kisser. He kept his mouth mostly closed and pushed too hard. When he pulled away Cindy rolled her eyes slightly without thinking about it. 

"Ok, no need to even ask her. Junior, that was a terrible kiss. Cindy, do you mind if I show him how it's done?"

Cindy could hardly refuse now, so she nodded sweetly. The older man held out his hand and when Cindy took it he pulled her against him. Ed was very confident, and when he leaned in to make out with Cindy it was immediately obvious he knew what he was doing. Cindy closed her eyes and imagined James kissing her again. Ed took the opportunity to run his hands over Cindy's much handled ass cheeks. Finally he broke the kiss.

"Were you watching Junior? I can tell you Cindy knows how to kiss...maybe let her lead."

Junior walked over to Cindy who was still a little disoriented by the first swap in partners. He looked down at her, and she realized he did indeed want her to lead. Cindy again imagined the boy was James as she put her hands on his cheeks and kissed him. Cindy gave him a little tongue and he opened his mouth obligingly. Cindy imagined she was James and the boy was her and she kissed him a bit more aggressively. She felt his hard cock now pressing into her and reflectively stopped the kiss and stepped away.

"Wow," the older man remarked as Cindy looked at the boy's wide eyes. "Didn't we get you a good teacher Junior?"

Junior stammered ascent and the man noted the tent in the boy's pants with a laugh. "Ah, Cindy, you might have to take care of that for the poor kid."

Cindy froze, wondering if she understood the man correctly. 

"Oh, and I should have said, this is not company business, just a personal favor. I'll give you a little extra for your help."

Cindy thanked him, but she was wondering if he meant for the kissing lesson or something more. 

"Well, take it out for her boy. Cindy's a good girl she's not going to help you out if you just stand there waiting."

Cindy noticed the Eddie's hands were shaking a little as he unzipped his ill-fitting pants and took out a fairly impressive sized cock. Cindy felt bad for him, and didn't want to humiliate him in front of his father. She sighed a small sigh and reached down to grab the boy's cock. 

Cindy felt confident giving a hand-job. She had given her boyfriend almost twenty before she finally let him fuck her. Cindy felt wistful for a moment remembering her old boyfriend, and she wondered what he was doing back in Eureka. She decided that she would imagine jacking off her boyfriend rather than Eddie, and that she would imagine they were back in his car, rather than an office with a father watching. 

Cindy pumped from the shaft the way she knew her boyfriend liked it. She spit on her hand to make it slide easier just like she had back home. Gosh, was it really wasn't that long ago. She was just getting into a nice, slow rhythm when she realized Junior was about to spurt. Cindy instinctively pointed the cock away from her, and the boy came in spasms on to the floor. 

Despite not having to overly exert herself, Cindy was a little out of breath as she released Junior's cock and stood up. Junior thanked Cindy sincerely, then scrambled to clean up his mess with some kleenex from his father's desk. 

"My Cindy, you are much better at this than I imagined. Watching you in that little outfit has got me rather excited as well. Would you mind?"

Cindy was taken aback. She wondered for a moment what would happen if she refused. She was doing so well with her career at this company and she certainly didn't want to lose the opportunity. But she couldn't give out handjobs all day. She convinced herself that this was a special occasion. She should probably understand that Ed would get worked up after kissing her then watching her bend over in the tiny shorts to give a handjob. Perhaps as she was at the company longer they would allow her to wear more sophisticated outfits.

Cindy told Ed that she would be glad to help if he needed and Ed quickly took his cock out of his pants. Cindy noted how it was similar to his son's. Not as hard though. Cindy walked over and when she squeezed it she saw it harden a little immediately. Ed's cock was thicker than his son's, more like James'. Cindy spit on her hand and stroked the way she had taught herself to. Ed reinforced her actions with moans. Cindy stroked it back and forth. She was not imagining she was somewhere else, she was very aware that she was bent over in a tiny outfit, with her boss' cock in her hands. Ed seemed to be enjoying, but she could feel him softening when she slowed. Cindy sped up but after a while that also failed and he began to soften in her little hand. Cindy remembered this had happened with her teacher in high school and realized what she had to do. She knelt before her boss and took his cock into her mouth. Ed became fully hard immediately. Cindy closed her eyes to remember what it was like when she gave her first blow job to her teacher after class one late afternoon. He had been very patient with her, teaching her exactly how he wanted it. Cindy remembered hearing her classmates outside while she had been on her knees with their teacher. She tried to remember how many times she had done this. She had never told anybody, especially her boyfriend. It had been a secret, just like with James, she thought. 

Suddenly she realized Ed was about to cum. Cindy knew from her teacher that she should swallow it all, and she tried her best as her boss grabbed her hair and began shooting into her mouth. She choked a little but managed to get it all. Ed finally pulled out and Cindy stayed on her knees a moment, trying to ground herself. 

Cindy, you are the best." Ed said. "We are so lucky to have you here."

Ed reached down and helped her up. He was always a gentleman Cindy thought. Her boyfriend was much less sophisticated than the men in New York, and never even held the door for her. 




Cindy's Adventures in NYC Ch. 06



Ed fished into his wallet and handed Cindy a wad of cash. "Thanks for helping out the boy Cindy." Ed said quietly, as if his son, just a few feet away couldn't hear. "Thank for everything."

Cindy took this as a dismissal, thanked Ed and then walked out of his office in her little Hooters outfit with the cash in her hand. She was grateful there was nobody in the lobby when she hurried back to her desk. It had been such an eventful morning. Cindy took out an Altoids, looked around and then counted the money she had been given. There was over $200 there. Cindy smiled and took out her phone. She opened the calculator to see if she might have enough to pay her bills off but as she did so she received a text from James. He had entered his name as 'Grande' on her phone and she smiled when she saw the nickname appear. 

The text read, "saw a pic of you in that outfit. not supposed to be in office, but can you meet in stairwell in 10?"

Cindy quickly texted back "yes. will be there."

Cindy smiled. She had wanted to see James again, but she knew he was very worried about anyone finding out about them. Cindy took another Altoids and tried to arrange her outfit before realizing there was not a lot she could do with it. Cindy quietly went to the staircase. She went down half a flight, unsure of where he would want to meet. She looked at her phone and realized it had only been a few minutes since he called. Cindy felt a little silly alone in the staircase, nearly naked. She didn't think anyone used the stairwell, but what if someone came? 

Cindy tried not to think of that, instead she filled her head with thoughts of last night. She got wet again as she remembered, and looking down she saw that the wetness showed through if someone looked. She worried the men might do so. 

Suddenly she heard a door slam, and steps coming. She hoped it was James, but she crouched down, as if that would hide her if someone came by. She looked down and saw James coming up from a couple of floors below. Her heart leapt. She had missed him.

James was a little out of breath but told her how sexy she looked before he pulled her into his arms. Cindy loved the feeling of being smothered in his big chest. She could feel he was already hard.

"We don't have a lot of time Bonita." He had given her this nickname and she giggled when he used it. 

"God, I want you." he said as he tilted her head up and kissed her hard. He dry humped Cindy a little while he did this and she worried he might get her juices on his dress slacks. 

James pulled Cindy away then turned her around. He bent her forward gently so her arms were resting on the stair railing, then pulled her little shorts down to her knees. James pulled out his cock and put on a condom. Cindy thought for a moment how this was the third cock she had seen in the last half hour but quickly forgot the concern when James rammed his into her, sliding in easily. He fucked her hard, with the urgency of a man who had been thinking of nothing but this moment for hours. Cindy gasped each time he pushed into her, slapping his body on her ass cheeks. She wished she could feel this forever, but she quickly felt James start to spasm inside her and she squeezed him the way he said he had liked last night. 

James pulled out and patted Cindy's ass affectionately. "I needed that." he said gently. James put his cock back in his pants and zipped up. He took young Cindy in his arms, her shorts still around her knees and thanked her for coming down. 

James explained that he had to run and reminded her to only text him if he texted first. Cindy agreed and he told her again how good she was. Cindy watched James head off down the stairs as she pulled up her shorts. She was feeling very horny, even more so now that she had been all worked up without reaching an orgasm. She had never felt like this until she got to New York. Sex had been much more for her boyfriend than for her.

Cindy tried to discretely come back to the office via the stairs and was grateful nobody saw her emerge. Some time after she settled back into her desk, Tony came out of his office in a huff. "Cindy, we looked everywhere for you, where were you earlier?"

Cindy stammered and started to say something about the bathroom but Tony wasn't really listening. 

"Ben wanted to say goodbye but he had to leave. We even checked the bathroom and you were nowhere to be found."

Cindy apologized but Tony did not seem like he was in a forgiving mood. He told her to follow him into his office, which Cindy did, her head hung down. Cindy shut the door as instructed and Tony lectured her like a little girl about the importance of taking work seriously. "You look sexy in those outfits, but that doesn't mean you can just come and go as you please without telling anyone."

Cindy tried to reassure that she would do better. Tony simply pointed to his lap and Cindy understood she would have to submit to another spanking. Without being asked, Cindy slowly pulled her own shorts down, very aware of how wet she was, then quickly bent over Tony's lap. 

Tony took his time and Cindy squirmed with anticipation in his lap. Cindy had stripped for many more men in the past week than she had ever stripped for in her life. She had been fondled by more men...pleased more men. Scores had seen her in various states of undress, but even after all of this the act of bending over her boss' lap with her bare ass raised for him made her feel intensely humiliated...and aroused.

"I think you actually like this Cindy." Tony remarked as he teased her by stroking ever so lightly around her asshole. "I think you behave badly because you actually enjoy being spanked by me. Isn't that right?"

Cindy didn't want to answer wrong, "I...yes...mmmm...I mean I...I do enjoy...if you think I deserve..."

Swaacckkk! Tony slapped her left ass cheek hard. "You do deserve it don't you?"

"Yes...I..." Swaaackkk! Swack! Two more slaps to the same place cheek turned Cindy's cheek bright red.

"Tell me you're a little slut."

Cindy spoke quickly, the words coming out faster than her thoughts, "I am. I'm a little slut who dresses up for everyone and does...what they tell me to..." Swaaaackkk!

"Good girl. That's right, you've probably fucked every man in the office or will soon." Swaaatttaackkk!

"I'm sorry...please...please tell me how to make you happy?"

Tony stopped his spanking for a moment and stroked Cindy's sore bottom. She was grateful. It felt so soothing to her.

"That's a good question Cindy. I promised my wife I would stop fucking sluts."

Tony continued to stroke absent mindedly, "I suppose...you do have a sexy ass...if I just ran my cock here along the crack...I wouldn't be breaking my promise."

Cindy agreed eagerly, assuring Tony that this would be fine. She actually begged her boss to rub his cock on her ass.

Tony slapped Cindy lightly on the ass and told her to get up, then told her to bend over his desk for him. Cindy never thought to resist. She very much wanted to please Tony, who was the most difficult of all the men in the office to make happy. Cindy bent over the desk so her face was lower than her bottom. She set her legs apart to try to spread her ass cheeks and make if more inviting to Tony. She was too intimidated to look back, instead she kept her face to the desk. 

Tony took his time. Cindy could hear him rustling around, and finally hear his zipper. She shook slightly in anticipation. Tony stepped forward and she could feel his presence behind her. She looked down and could see his well shined shoes just behind her sneakers. Finally Tony slapped his cock on to her ass. She could not see it, but he was very hard, and his cock felt hot against her skin. 

At first Tony glided his cock rather gently along her ass crack. Cindy surprised herself with a moan. It felt ticklish, and exciting to have a cock tease her skin like this. Tony started to increase his strokes and push a little harder. As he pushed more he went deeper into her crack, and his cock became lubricated with his sweat and hers. Cindy repeated after Tony on his instruction, "I am a dirty slut. Please fuck my ass crack!"

As Tony pushed even harder she could feel his balls push into her asshole, which made her tingle all over. With longer strokes Tony eventually was running the full length of his big cock along her asshole. Cindy never knew she had so much sensitivity there. Her eyes were closed as she pushed her ass back into him with every thrust. Suddenly Cindy felt the tip on Tony's cock push against her asshole. She let out a startled moan, half pleasure, half pain. A few more strokes and it happened again, but this time Tony did not stop. He pushed his cock inside Cindy's virgin ass. Cindy had to muffle herself in her arm so the whole office wouldn't hear her moans and whimpers. She felt so dirty and it turned her on incredibly. Cindy reached down and fingered herself. Tony continued to push into her ass. With each stroke Cindy felt herself getting more and more excited and she fingered herself faster. Finally she felt herself orgasm intensely, like she never had before.

Cindy closed her eyes and gave herself to the feeling. She wanted it to go on and on. She heard Tony grunt and felt his hands tighten around her hips as he shot into her asshole. Cindy pushed back into her boss until he finished and pulled out. 

Tony spoke slowly as he cleaned himself off with a Kleenex. "Well done Cindy. I think this will work out fine. You do whatever you want with the other men, but you save your ass crack for me."

Cindy was a little perplexed as she stood back up on whether Tony really thought he had just stroked along her ass crack, but she simply agreed that would be fine. As she started to clean herself she heard a voice in the lobby calling her name. Shit, she thought, that's Stephanie here early for lunch. 

Tony dismissed the teen so she could attend to whoever was shouting. Cindy pulled up her shorts and tried her best to look as presentable as a well fucked girl could in a tiny Hooters outfit. She opened the office door and scurried to the lobby where she found Stephanie still calling for her.

Stephanie's eyes went wide when she saw her roommate. "Cindy...there you are...wow...looooook at you!"

Cindy blushed as Stephanie looked her up and down, and blushed even brighter when she saw that her other roommate Anna and her boyfriend Brad were also in the lobby, staring at her.

Anna laughed "Wow...little Cindy has really grown up. What have you been up to here??!"

Cindy didn't say anything. She wanted to melt into the floor with embarrassment. 

"Give her your jacket, Brad," Anna said, "we won't get in the restaurant with her wearing that!"

Brad took off his jacket and placed it around Cindy's shoulders. Cindy was more than accustomed to men handling her and she stood still, with all eyes remaining on her.

"Come on Cindy, let's get going." Stephanie instructed" "Keshon is meeting us there. He has a big interview later and I promised you'd give him a little relief to free his mind before he goes." 

The three of them laughed and Cindy followed them to the elevator. When the elevator arrived it was rather crowded with people heading down for lunch. Cindy realized her erect tits were pushed up against Brad. She moved away to make sure Anna wouldn't think Cindy was making a move on her boyfriend. In doing so, Cindy pushed her bum against a suited man's crotch. She felt his hand brushing against her bare ass cheek. It was not nearly as aggressive as what she had grown accustomed to, but she was sure it was not by accident. She felt the man harden against her as the elevator stopped at another floor. 

Cindy heard her phone buzz in her purse and pulled it out to check it. It read 'Darling, know you left early for weekend but client in for dinner tonite. Would love you to help entertain. Be back at 7 and bring the maid costume. Ed'