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'