Cindy's Adventures in Nyc

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.