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.