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.
