Tom Mollenkoff owned The Bootlegger, a bar that was on the border of the middle class area of town and the more dangerous slums. Even though he was a big ugly nasty son of a bitch, everyone seemed to get along with the guy; probably because he owned the closest bar. And sometimes he would even buy a round for the house, but only if the house was less than half full of patrons.
His clientele was a mixture of blacks, whites and Hispanics from varying backgrounds and income levels. His two waitresses had been with him since he opened the bar 18 years ago after he got out of the army. Brenda was a divorced 41 year old that had graduated from high school with Tom, and Cindy was a 200 pound 28 year old that was still living with her parents.
During the week, Tom and one of the waitresses would work each evening, and then he would have both of them work Friday and Saturday nights. When he needed help behind the bar or wanted to take a day off, he would use his nephew Jack a couple evenings a week.
Tom's business was quite good and he was floored when Brenda told him that she would be quitting in two weeks so she could get married. Tom tried everything to get her to stay, but she had already decided to quit. She agreed to ask her daughter if she knew of anyone who might be interested in working at The Bootlegger and Tom sadly agreed.
Two days later while Tom was behind the bar in the afternoon with only two customers at the bar, a young black girl walked in. Tom saw that she was wearing a tight pair of jeans and a button up top with the top two buttons open. She looked to be about 5'6" tall and was quite pretty.
"Can I help you?" He asked.
"I hope so," she said. "My name is Nicole. My friend's mother is Brenda and she said you're looking for a waitress, and I would like to apply."
Even though he had a large group of black customers, Tom had never employed a black person before. After they had talked for a while, both of them agreed to give it a shot and see how it worked out. As she left the bar, Tom admired her walk and her shapely ass.
The first night, Nicole wore jeans and a loose fitting top and impressed Tom with her hustle. Friday night Cindy and Nicole both worked and they were both kept hopping all night, but they both did pretty well with their tips.
After they closed and Tom was counting the register, Cindy and Nicole sat at one of the tables drinking a beer. Cindy said, "You're a cute little thing, Nicole. Do you have a boyfriend?"
"No. I'm just trying to save some money to get a car and I don't need a boyfriend getting in the way."
Cindy asked, "Well how did you get to work without a car?"
"I just live three blocks away so I walked. I might ride my bike sometimes," Nicole answered. Cindy nodded, stood up and told Tom and Nicole she would see them tomorrow.
Tom came over to the table and sat with Nicole. She was excited that she had done pretty well with tips on her first night on the job. Tom smiled and said, "Well, let me clue you in sweetie. If you wear a short skirt or tight top, you'll get bigger tips and will be able to buy that car sooner Did you notice that Cindy had on a very low cut blouse tonight?." Nicole nodded. "Her tips were probably double yours because she flaunts those big 42DD titties of hers. But you guys can wear whatever you want. Your tips are your business."
Nicole thought about it and said, "Thanks Tom. I appreciate that."
The next night Cindy wore a tank top that was extremely tight over her 42DD breasts. She had even made a tear between her breasts showing more cleavage. Nicole wore a thigh length skirt and a tight tee shirt. When she walked in, Tom felt a stirring between his legs and thought, "Holy crap. This little bitch is something else. I may make a run at fucking this bitch."
The bar was packed and both girls worked harder than the previous night, but they both more than doubled their tips. As soon as they closed, Cindy hurried out the door on her way to an after hours party. Nicole sat at the table nursing a beer and counting and recounting her tips. Tom walked over and she said, "Wow! I never knew I could make this much in tips working in a bar."
Tom smiled and said, "A lot of it comes down to what you wear, Nicole."
She said, "I can see that, Tom. Wow, thanks for the advice."
They got up and Tom put his arm around her and walked her to the door. "Well, see you Tuesday, Nicole."
She smiled, gave him a hug and said, "See you then." As she turned to go, Tom patted her ass. She turned and grinned at him and gave it a shake before walking out the door.
Tuesday night Nicole wore another short skirt and tee shirt. Although the crowd was no where near as large as the weekend crowd, Nicole still made a respectable amount of tips. At the end of the night, she and Tom had another beer together and as he walked her to the door, he had his hand resting on her ass. When they reached the door, she turned and said, "Tom I'm doing really well on my tips. Are you sure I don't have to share them with you?"
Tom laughed and pulled her close in a hug putting both hands on her ass and said, "No baby. It's all yours." He leaned down and kissed her before she realized what was happening. She tried to pull away, but he was too strong. He broke the kiss and spun her around putting one hand across her breasts and the other on her pussy outside her skirt. She attempted to get away, but his hand began squeezing her breasts and moving under her skirt.
"N-no Tom," she begged. "D-don't."
His hand slid under her panties and he pushed a finger into her damp pussy. She moaned quietly. Her nipples were hard and Tom twisted one of them. Nicole stopped fighting. "P-p-please. N-no. Sto-stop Tom>"
He had an evil grin on his face as he slid another finger into her pussy and continued twisting her nipple. "Oh! Ple-please d-don . . . "
"What?" He smirked at her while continuing his machinations of her body.
"Please . . . Oh. Aaaah! Uuunngh!" She moaned.
He said, "Take off your top."
"I don't't th-think I . . . Oh Tom," She said. She reached down and slowly lifted her tee shirt over her head and dropped it on the floor. Tom unfastened her bra and dropped it on the floor. He put his hand back on her breast. He now had three fingers in her soaked pussy. "Aaarrgh! Tom. Oh."
He whispered in her ear, "Take off your skirt and panties. Now." Nicole reached down and unfastened her skirt and it fell to the floor. She bent over and slid her panties over her hips and down her sexy legs. She stepped out of her panties and skirt and Tom turned her around. He leered at her and said, "You will be the first black woman I have ever fucked." She looked up into his big ugly face and just nodded.
Tom picked her up and carried her to the back room where had had an old stained couch. He put her on the couch and unzipped his pants and pulled out his hard nine inch cock. He waved it in Nicole's face and said, "Suck it." She wrapped her lips around his sweaty cock and began sucking. She was only able to get about seven inches into her mouth but she kept trying until he said, "That's enough. Now tell me you want me to fuck you, bitch."
She looked at him in confusion. "What?"
"Look bitch. At this point, you're not worth me taking off my pants for. You have to prove to me that you're a worthy fuck. So tell me you want me to fuck you."
