Under His Wing.... (closed for Mayu)

Steve5511

And nothing else matters
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Dec 20, 2007
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Bobby Heart was his real name. Though it sounded like a name made up for his business, it was his true family name. And his true family business. His mother, the famous Cherri Heart, started out as a 19 year old dancer and after some wise investments, owned the club she worked in. Bobby grew up in the club, in every way possible. All the other girls would take care of him when his mom was on stage. when he was 10 he would run onto the stage to collect the clothes the previous act would leave out there. After returning from college with a business degree, Bobby would bring the club to heights few had seen. It was no longer the strip/bar it started out as. It was now among the top clubs in the country. Many dancers went on from here to star in the exotic shows of Vegas and Paris. And Bobby knew all the secrets and had the connections to get them there.

At 6ft 2 and about 210 lbs, his looks weren't that bad. But it was his eye for talent that drew the women to him. He could tell right away if a woman had what it takes to be a star in the exotic dancing world. There was a difference between a star attraction and a whore. Bobby knew how to make both.

By now the club almost ran itself. Bobby's mother had retired and due to the success of the club she could travel and enjoy her life. Business school had taught him to surround yourself with good people and he did just that. His books were handled by a Columbia grad and the club manager had worked at the top hotels in Vegas. All was being taken care of but Bobby was still the boss. His word was law and he was respected by all. Most nights before it got busy, Bobby would spend some quiet time in the diner acrossed the street. Sitting in his booth sipping his coffee and reading the paper. The quiet before the storm.
 
Lisa was the kind of girl no one wanted, she had the body to be sexy. But she always wore the wrong things, only thing she couldn't screw up was her eyes. They were almost cat like and they were very gray and it was a rather beautiful look, she was always the friend never the girlfriend. And even then she didn't have any true friends, she had a habit of letting people walk all over her. And she would even admit she lets it happen, she graduated high school two years early. She was a very bright girl as well.

She went to college and left there when she was almost nineteen, she had a taste for fashion. Or to at least work in it as something, she got a job working as a secretary to a highly respected woman. Her name was Sarah Dutch. Though Sarah pretty much loved to tare people down, spit in there face in a matter of speaking. She was pretty much using Lisa for some fashion ideas that she had, but the girl never put up a fight.

But her life was about to change, she wore a pair of blue jeans and a black shirt. She came into the cafe and moved passed a man reading his paper and drinking his coffee. Lisa sat down and ordered the house breakfast, which was a simple dish of eggs, bacon and toast. The classic, and she had a black coffee as well, she sighed sadly looking out the window. Lisa knew she had to grow up, stop letting people walk all over her. She was rather lonely as well, by looking at her you would never believe that she is actually a musician.
 
As he read the news of the local town, his "Sixth Sence" started to go off. It was a feeling he had deep inside of him. He couldn't explain it but he knew when it was getting his attention. He looked up from his paper to see a very sexy ass covered in jeans pass him. Though they were baggie he could see what was hidden. As she turned to be seated Bobby noticed a large but not overly large set of breasts again hidden under a shirt. But when he got up to her eyes, that special thing inside of him clicked! Those eyes had the potential to be something special.

She was a very pretty girl but didn't know it. She didn't move gracefully at all, more like she shlept along. Bobby thought of her a s a new piece of clay. He could mold her into a star. If she put in the work, she could own the stage plus any room she walked into. Hiding agin behind his paper his mind whirled at all the possibilities.
 
She felt like eyes were on her, but she just shrugged away the feeling. Putting one leg over the other, making sure to relax against the back of the seat and sighed a bit. After about ten minutes she noticed the waitress coming over with her food. She did have manners thankfully, she cut her food before eating it. And she did eat with her mouth closed, and never spoke with her mouth full. Sighing a bit as she thought about many things, she took out pride and prejudice from her bag and got lost reading it.

Getting so lost in the book she didn't realized she had finished her meal till she tried to take another bite. She chuckled to herself seeing no more food and put it up, drinking her coffee and sighed a bit. She looked up seeing the man again, something about him she grew curious about. But since it wasn't her business, she put her book up and waited for the check. Looking outside again she could see rain slowly hit the glass of the window, she smiled realizing that it was going to be a rather wet day.
 
Bobby looked at his watch and new it was time to head to the club. He had a few things to talk about with one of his lead dancers before she went on and a few other bits of business to take care of. He downed the rest of his coffee and left money for his check. He was in there often enough that they didn't even really charge him, but he always wanted the waitress to get a good tip. He knew they worked hard and some of them even tried to work for him.

The door was the other way but he just had to do something first. He walked to her booth and said "Excuse me, I just wanted to tell you that I think you have an amazing pair of eyes." He dropped a $20 on the table along with one of his cards. "Please let me buy you breakfast. If you want to get the full potential from those eyes, and the rest of you for that fact, give me a call." He then turned and walked out after saying goodbye to the wait staff and hostess. Bobby pulled his coat over his head and sprinted in the rain to his club.
 
She looked up seeing a man and he was rather cute, she blushed when he said what she did. Buying her breakfast to?" She saw the card that he put down, and the comment about her eyes. And watched him leave, she had no idea who the hell he was. She looked out the window watching him, it was incredible. Watching him take of in the cab she sighed a bit, and got up and took the card and walked out. She headed for her job during the day, which was of course boring as hell. All through the first half of the day she kept seeing his eyes.

Going into her purse during lunch she looked at the card that he left for her. Looking at the words, she decided to give him a call. It was her lunch break any way, so she dialed the number and it rang a few times. But then a voice mail kicked on, thinking about how smooth his voice was. Closing her eyes she didn't know if she should leave a message or not. Was this meant to be? Why her what did he see in her? No one gave a crap about her. But hearing his compliment again in her head she smiled.

"Hi this is Lisa Wolf, we met at the diner I would like to take you up on that offer. My number is 555-2030 thanks" Then she hung up figuring she would never get a call back.
 
Believe it or not, Strip clubs have a very busy lunch time crowd. Many of them even have a free buffett so you can get a bit to eat after a lap dance. Heartbreakers wasn't like that. They didn't need to go that route to get a crowd. This club was known for the hottest girl in any town. Business men and women would come in to have a drink and watch the girls, getting lap dances and other "private room" services.

On his way to his office Bobby had a little meeting with Crystal, the star attraction for the lunch crowd. He wasn't happy with the way she was stripping off her bra. "You're just opening it up and letting the girls fly out. You need to make the crowd want to see them" he told her. Bobby has seen hundreds of girls come and go. So when he gave them advice, it was only in their best intrest to listen to him.

Up staris from the club was where the offices were.This was no 2 bit operation run out of a cigar box. From the looks of these offices you would think that you were anywhere else but a strip club. Bobby's office was at the end of the hall, away from the front door and the rest of the club. He had the walls sound proofed to keep the loud music downstairs out and to keep and of his "private" conversations in. He sat at his big dest looking through his mail and pressing the button on his answering machine. The useual messages and mail were there as well as a message that got his attention. Lisa Wolf..... now he knew her name. Bobby sat back in his chair after taking down her number. With his eyes closed he saw her before him and in a split second, he ran through her career all the way to the top.

He called her number a little while later and told her to come by the club so they could talk. He said that the staff would be told that she was expected and that she would be brought right to him. Bobby hung up the phone, had a quick drink and went down stairs to talk to one of the dancers about shaving her bush. Ahhh the life in showbiz!
 
She was working busy and in the middle of her work got a call, she smiled and agreed to go of course. Hanging up she finished off her work, and then got her office situated for tomorrow. Standing up she looked at the mirror she had in her small office, looking at herself she sighed a bit. She wanted to be beautiful, to have everything. But she was so afraid, but she had actually been a very over weight child. She had insecurities so much she did what she could to loose the two hundred and thirty pounds.

Hearing all the names that hurt her, she had stopped eating. All she did was drink water, to make it so she would get full. The stretch marks and marks of being overweight did fade, she had a perfect body now. She had a crush in school ask her to the prom once, and of course it was a joke and she felt like Carrie in that moment. Being made fun of, the kids were just lucky she didn't have the powers Carrie did. But now in the real world, who you were in high school didn't matter any more.

So taking a deep breath she walked on out and went over to the strip club, going in she saw some of the woman dancing already. They were rather beautiful, and stopped to watch one dance. She was wanting what they had, and that was self esteem. What no one knew was that she could dance and she could sing. She shook her head and walked up to the bar and told them, one of the strippers that was waiting to go on. Took her hand gently and showed her to the back. The woman was rather pretty. But soon she looked over at the man again.

"Mr. Heart" She said kindly.
 
Her voice rang right through the noisy club like a bell. Bobby was watching the girl on stage who just wasn't getting it. Sure all of the guys in the audience were going wild for her big tits and hot ass, but she could be so much more. Not taking his eyes off of the dancer he said "Hello Miss Wolf... Glad you made it." He shook his head from side to side as he watched "Candi" finish her act. "She can get a crowd going but she can't close the deal in a one-on-one with anyone over 26."
Turning to see Lisa, he smiled as he shook her hand "I'm Bobby Heart, welcome to Heartbreakers. Shall we go up to my office and talk?" He led her up the stairs and down the hall to his office. As they made their way, they passed some of the "private" rooms where alot was taking place. Bobby turned to Lisa and said "some big money in there tonight"..

They got to his office and Bobby pointed to a chair for Lisa to sit. He offered her a drink as he poured himself a seltzer and sat behind his desk. Bobby got right to business and asked her point blank "So Miss Wolf, what can I do for you?".
 
She smiled following him, when he offered her a drink she took one some whiskey since she was pretty damn nervous. But didn't hide it, the drink helped her to talk like she wasn't a babbling idiot. She had known about this place, she smiled a bit as she watched him move. And paid attention to his question, what could he do for her? Thinking about the girl that she had watched dance when she came in, her name was Sky. Least that was her stage name, she had heard someone calling her name. Looking down at her drink she sighed.

"I know about this place, my father use to be a bartender here back in the day. This place isn't like any other strip club, I know the history of the joint. Though I know I do not know you personally Mr Heart. But I think this isn't just another place for guys to watch women strip, best of the best. Having a nice body can only get you so far, but it's also skill I think. What I want is to be like one of your girls, perhaps not be a stripper. Don't think guys would like my breasts, but to be able to do something wild."

She said looking up into his eyes "To not be afraid of the body I have, I have never had self esteem because I had been a big girl all my life, till I hit Junior year in high school. The kids there was like walking into a lions den every day, but now I am afraid of what I have become. I don't know anything for fashion, I know there is a sexy me banging into me begging to be let out. But I don't know how to do it, you seem like someone who cares for his girls. I need a chance to be something special." She said looking back down.
 
Bobby played with the ice cubes in his seltzer as she talked. He watched her open up to him and could tell that she was sincere. In his mind he already had her out of her clothes and she wasn't too bad! When she stopped talking he let the silence fill the air. Just looking at her as he swivled in his chair. He put his drink down and cleared his throat.
"Well first things first, if I'm going to work with you then you will be stripping. I'm not running a YWCA here, this is a business. Your story, while touching, isn't the only story out there. I have heard them all before. But the only thing that story is good for is inner drive. It will be useful."
Bobby now got up and walked to the front of his desk before Lisa. "If I agree to take you on, you will do what I tell you and to the best of your ability at that time. There is no negotiating, I'm the boss and my word is the law. That said, while you are in this establishment, you will be safe from harm. I have eyes and ears all over the place and a security staff that could take on any team in the NFL. If you decide to leave on your own then thats it. You are out. Is all of this clear?"
 
She heard what he said and was taken back by how he took his job, he was passionate about it. Slowly looking out the door to see one of the woman, she started to fantasize it was actually her. Proud of her body and not afraid to let it all hang out, she got a feeling in the pit of her stomach. Looking at her drink as she finished it. Again there was a silence as she heard his terms, she agreed with them. It seemed fair that he was willing to open up his place for her, so a smile formed on her lips. Putting her drink down in front of her on the table on the coaster.

Slowly locking her grey eyes on to him she nodded to him. "What ever it takes, I will do it" She said finally and smiled even more at him. Allowing her answer of yes back to him flood her heart, she didn't know how this would go. But she wasn't afraid, she had been through a lot in her life. Course so hasn't everyone else, she didn't tell him her story to make him feel sorry for her. "I just want you to know, I didn't tell you my story to be felt sorry for. I did it so you could understand me, because pity doesn't interest me. Respect and Freedom over ones body does"
 
Bobby smiled at her as she agreed to his terms. He knew he was stern, but he was also fair. He just hoped that she was ready for what she was about to step into. They shook hands and Bobby went back behind his desk. Looking up to her he said "OK, now it starts. I hope you enjoyed that breakfast you had today because you won't be eating that again for a while. Clean up your diet. Also there's a group of girls here that go running every morning at 7am. They meet here and go 5 miles. You should be here tomorrow morning."

Lisa's eyes opened wide like she had just been drafted into the Army. Bobby was like a drill instructer barking out do's and don'ts. He told her to prepare some kind of routine so he could see if she had any ability as a dancer. Then came the words that took Lisa by total suprise. She had to have known it was coming but didn't think it would be tonight. Bobby once again looked to her and said "OK, now stand up and take off your clothes."
 
She was surprised by all this but she wasn't to afraid of it, she was just glad she kept her body clean and perfect. Slowly standing up she removed her jacket, and began to remove her shirt which showed a silk black bra. She removed the jeans that she knew was way to baggy for her, and removed them as well. She surprised herself at what she wore since it was rather sexy things, her panties was actually a thong. She always kept up with the bikini waxing, she had since she got this body of hers.

She took a deep breath and reached behind behind and un clipped her bra and slowly removed it. She has a good pair of breasts, they were natural and was about a 32C cup. Looking up at Bobby she saw the way he looked at her, so she slid the thong down. Moving it to the side, she wasn't a ghost exactly but not the tannest either. Looking up at her chest, she noticed her hair was blocking his eye shot of them. She took a deep breath and silently let it out as she pulled her hair back looking back at him.
 
He was impressed that she didn't balk at his request. It's always the first time that they are naked that most of them run out. He was glad she stayed. If she only knew how much he was trying to keep his dick from getting hard right now. With the right mindset to go along with that body... He had a winner here. Snapping himself out of his daze he said "Are those about a 32C i'm guessing... very nice. Turn around and bend please."

After she turned away Bobby let out a deep breath, WOW she is HOT he thought. As she was standing there stark naked he figured he might as well push her limits a bit to see what would happen. He then asked her a bunch of questions that he knew would push the buttons of any woman. "So, Do you suck cock? Do you swollow? Do you do anal? Have you ever been with a woman?" Bobby sat back in his chair waiting for her replies as he his his hardening cock under the desk.
 
She was taken back when he wanted her to turn and bend, but she did it any way. Slowly standing up, she ran her fingers in her hair. And tried to show confidence in her eyes, but then he asked questions that made her want to run out and never come back. That was the problem, always the friend never the girlfriend. She looked down and figured that after she was open and honest, he wouldn't want her and would tell her to leave. But she couldn't lie either, if he had ever told her to have sex with him or to please him.

She would fail it horribly, taking a deep breath she sighed shaking her head to herself. "That's the problem when your always the friend, never the girlfriend. Only close to a cock I ever got is a banana if you want me to be honest and frank, my body was never wanted. I was never wanted in the way of sex, I know how to give a blow job because of a piece of fruit. And unfortunately I'm still a virgin" She sighed a bit figuring that this wasn't going to work for him, so she was preparing herself for the "Okay can't help you leave" moment, she was afraid would come.
 
Bobby fell silent when she spoke. He could see he blush a bit and almost start to shake. In a soft caring voice he said "put your clothes on and take a seat." He rubbed his temples and eyes as she did that and then got up to lean on the front of the desk again.

"I asked you those questions not to be nosey or perverted. I need to know that if you are giving a lap dance and the customer says "show me how you go down on a guy" that you know what that is like. I need you to be able to dry hump the shit out of a guy so he thinks that he's really fucking you. This business isn't all about T&A, it's about the perceived possibility that they will get to fuck you. Thats why it's called a tease. You get them to think they are about to get the fuck of a lifetime, and then you dont."

Letting that all settle in for a bit, he then says "Well go get some sleep, have a HEALTHY breakfast and join the girls for the run. I presume you have a "real job" so I won't expect to see you here until 8 tomorrow night for your second lesson. You just had your first."
 
She listened to what he said and thought about what he said to her, and was actually taken back that he still wanted to help her out. She got dressed quickly and heard what he said about the jog and she nodded to him. Lisa was impressed by him and he seemed to still have high hopes for him, and thought about it for a moment. Looking back at him, he really did open up her eyes to the possibility of something here.

"You won't regret this Mr. Heart" She said and she left she headed on home and got a good night sleep, she woke up in the morning and ate some good foods. She had an Apple with some oat meal, with very little sugar and made sure it wasn't loaded with calories. Then she got into a shower, grabbed her woke cloths then put on a jogging outfit. Meeting the girls for a jog scared the shit out of her, they were the kind of girls that made her feel bad about herself. But after a while she realized the route so she actually got faster at running.

When that ended she headed to work, and was getting a bit more relaxed. She got dressed in the ladies room and made sure she wasn't sweaty and a disgusting mess. She went on with the day, unsure how tonight was going to go for them. She didn't talk to any of the girls, so she didn't open herself up for any kind of comment. Rather it be negative or even a good positive feedback from them. All through the day she thought about Heart, and couldn't stop thinking about him.
 
After Lisa left his office, Bobby had Sky come on up. Lisa had him so worked up that he needed a release. As Sky took him in her mouth, he pictured Lisa's lips around his cock with those sexy eyes looking up at him. Before long he was shooting his load down Sky's throat with Lisa in his mind sucking it all down. Sky went back to the stage and Bobby just sat back to enjoy the moment.

The next day Bobby was back at his booth at the diner. He got a text message from one of the girls letting him know that Lisa made it to the run. That pleased him. She was willing to put in the work so far, being that it's only day 2. Even when the waitresses flirted with him as they always do, he had Lisa on his mind. He looked at his watch and saw that it was time to get to the office. He had a management meeting at 4 but then his night was free, except for all the fires that only owners can put out. But before he crossed the street, he needed to make a stop. A stop at the grocery store.
 
Lisa had a good day at work, now that she was out she decided to go to a grocery store to fill up her fridge with some healthy foods. She walked passed Heart not knowing it was him, she had a cart filled up with all kinds of fruits. But she was thinking a lot about Bobby, was he out of her league? hell did he even have a league? She loved this store, she knew the owners and her mother had been co founder for a while, till she died. But right now everything was just so perfect, thinking of Bobby she heard the song playing over head.

It was "Hips Don't Lie" By Shakira. She always danced to this, just something reached in and did it. She looked around and didn't see anyone, unfortunately she didn't look to the left since Bobby was right there. She began to dance with the music, moving in time with the music. Her hips showing that she could shake them, she let herself loose not thinking people were there. She knew how to dance sexy, she just didn't do it in front of people. She was even mouthing the words to the song as well.
 
Bobby picked up the few items that he needed and started to head to the check out. As he walked passed one isle out of the corner of his eye he spotted a pair of hips moving to the music playing above. Bouncing a nice sexy ass, those hips sure didn't lie. He was even more stunned to see those hips belonged to Lisa! Quickly regaining himself, Bobby made it to the check out and out the door. DAMN he thought, this girl is full of suprises.

Back at the club the meeting was about to begin as Bobby got there. He put his stuff in his office and headed tpo the conference room. It was the kind of meeting that any business would have only this one included talks about boose, music and tits. Bobby's mother had always had a "lead dancer" when she was running things and now wasn't any different. If anything it made the girls feel like their voices were being heard. Crystal was the lead dancer now so there she was at the meeting. When it was all over Bobby held Crystal back a little bit to tell her he was working on a project and might need her help a little bit. Crystal figured that was what was going on when she saw Lisa at the morning run. She said she would be happy to help out and then went to get ready for her first show.

After a walk around the floor of the club to make sure all was going smoothly, Bobby returned to his office to get ready for his "student". He had gotten a few things delivered while he was in his meeting so now he set up for when Lisa showed up. The image of her hips moving from before wouldn't get out of his head. He was also thinking about her with his "other" head!
 
She didn't realize that a lot of things was about to change, she stopped being an idiot and she paid for her things and headed home. When she got home she put her items in her refrigerator and ate an apple as she hopped into the shower, making sure that she didn't look terrible. She even re shaved her legs and underarms to make sure she was presentable. She had a bikini waxing two days ago so that was good. She was nervous and decided to try and look nice tonight, so after the shower she went to her closet.

Only thing she had nice was a simple black dress, it hugged her curves and it wasn't ugly or anything. Was the only thing form fitting she owned, so she slipped into a pair of black high heels and brushed her teeth. Then worked on her hair a bit, putting it into a bun where she had a few strands of hair hugging each side of her face. Smiling a bit as she put on a little makeup as well, some black eye liner and a little mascara. She didn't look to bad, she noticed the time and left her place with her keys. Locking up she flagged a cab down and went to the club.

Walking into that club was almost hard, she took a deep breath and entered it. It wasn't exactly busy in there, least not now. Her heart was beating out of her chest, as she smiled to herself how good she felt about taking the steps to do this. So she noticed someone flagging her down and she walked over to the woman and before her eyes she saw Bobby again. She smiled a bit as she looked over at him. "I hope you don't mind I am five minutes early?" She said to him.
 
Bobby was watching one of the dancers as he saw Lisa come to him.She looked great tonight, but in the going on a date kind of way. He did appreciate the effort though. Before she knew it, she'd be making guys cocks hard all over the place with that body.
"I hope you don't mind I am five minutes early?"

"No, not at all" he replied. His eyes running all over her body as she looked around still in a bit of amazment at the place. He wanted to see what she had on under that dress... and under that as well. "Why dont we go upstairs and get started shall we?"

They moved into his office where he closed the door behind them giving them thier privacy.
"Before we start, I have a little present for you." Bobby reached behind the desk and pulled out a box and handed it to Lisa. "I figured you were about a size 7 shoe. We can change it if you're not." The box contained Lisa's first pair of "Stripper Heels". 5 Inch platforms that all the girls were wearing now.
 
Lisa smiled at Bobby he had been watching a girl she could tell that rather easily, and nodded as she walked beside him. She was surprised when he got her something and when she opened up the box, she smiled at the shoes in there. And they were in her size as well, she smiled at him and was really happy and honored that he was willing to give her a chance, even though she knew this was going to be very hard. But she would bust her ass so she sat down looking over the heels, and it was very nice of him.

"No I am a size 7, and I am sorry for the dress. I know it's more of a going on a date, not going to work. But I just wanted to show that I am willing to do anything I have to, I actually enjoyed the run this morning as well. I get up early every morning any way, so I am just glad that I got off my ass and doing something" So she slipped out of her shoes and put on her heels and she slowly stood up walking around to get a feel for them. Smiling up at Bobby she was very grateful to him and nodded.

"Thank you for these heels to Mr. Heart" She said happily and looked at him. "So Boss what do you have planned for me tonight?" She said grinning.
 
Bobby watched her walking in the heels. A bit wobbley but pretty good so far. He did notice how they made her legs go on forever. He could see how her ass went up just a bit from the high angle of the shoe.
"You should practice walking in those around the house. Pretty soon they'll get mor comfortable. And while the dress is pretty, it's just not for here." Bobby reached down to the phone and dialed a #. "Hello Nancy? Bobby here. Listen, i'm sending you down a new girl that needs an outfit to practice in....OK great, thanks".

He hung up the phone and told Lisa "That was Nancy, she's in charge of costumes. Go downstairs and she'll fix you up with something. And while you are down there, I'll try and come up with your new name."
 
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