Pimp Daddy

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Note: this is a fantasy – in real life, please treat people with respect.


Angela Dario was 22 and in college, although she rather be working for her dad’s company. She was ambitious and loved business. Her father, Pablo, and his family came to the US when he was two years old. He took some classes at the community college, but never graduated. He worked two jobs at a time to support his family.

After working several years for other financiers, he recently started his own investment firm. Although she promised her father she would graduate and get her masters, she spent most of her time outside of class working for her father’s firm.

Angela was the jewel of Pablo’s eye. Unlike his son, Eric, who although only 18 and still in high school had no ambition to do anything but chase girls and play video games.

The firm, Dario Investments, was making good money, but an investment firm is only as good as the number of investors willing to part with their cash. They needed to reach some of the big players and over dinner one night Pablo mentioned a construction executive he was courting. He told Angela that the guy wanted a date, not a cheap hooker but someone hot, Pablo had no clue where to look.

Angela had someone in mind, one of her classmates just moved out into her own place because she took up a job at a strip club. Cheryl was good looking and pretty much a slut, best of all she really needed money. At first Pablo was against the idea. Prostitution was for low lives and once you get into this, who knows where it will lead. Eventually Angela convinced her dad and he reluctantly agreed.

When Angela told Cheryl she was at first offended, but when she found out she could make $500 just to meet with the client, her mind changed. Angela didn’t tell Cheryl that Pablo was her father; she said told her it was her boss at the firm. Pablo called Cheryl and told her that her date Mr. Jones was at the Park Hotel and that he would arrange a car and driver to pick her up and act as her body guard should she feel unsafe.

The next night Angela asked Cheryl how the “date” was.

“Well” Cheryl said. “He was old, in his forties, but kinda handsome and funny. I think he was more nervous than me. We sat and had a glass of champagne; eventually I made the first move and leaned in to kiss him on the lips. You know what? He was a great kisser. I got really hot.”

“Yeah…and then?” Asked Angela.

“And then? Well girl, he rocked my boat. These old dudes may not have the stamina of my last boyfriend, but he knew his way around a girl. In fact, I might just stick with old dudes from now on, they treat a girl like a woman.”

“really?” Asked a surprised Angela.

“Oh yeah. Not only did I have the big O, but he was so concerned about me staying in college, he gave me another $500. So anytime your boss Pablo wants me to go out on another one, just say when.”

Pablo called Cheryl for another date that Friday and another on Saturday. Cheryl quit her stripping job and made more money. She wasn’t the only one making money. Dario Investments was landing more and more clients. Word spread on how hospitable their customer service was.

A few weeks later, Cheryl called Angela.

“Hey girlfriend, I got a proposition for you.” Cheryl said in sing song voice.

“Oh hey Cheryl, how’s my favorite Ho?” She teased.

“Whatcha doin Saturday night?”

“Probably working late at the office as usual, why?”

“Forget that shit. I need you to come to my place, am gonna dress you in something sexy and your coming with me to meet a client.”

“Whaat? No way girl…I’m not…no way.”

“Your not what? A whore, like me?”

“No I errr..” Angela stumpled. It was her idea and as much as she hated to admit it, Cheryl has brought in more clients into the firm than she ever did. Upsetting her now would not be smart.

“Come on Angie, your boss has two big time clients, I can’t take them both and he asked me to find another girl. I don’t trust anyone enough. Do you want to ruin this for your boss?”

Angela thought about it. What was she going to do? Then Cheryl asked “besides, when was the last time you got laid?”

“Me? Well, ummm.”

“Yeah, I thought so. Look, for your own sanity, you gotta take a break from working and school and blow off some steam… and some cock.” She giggled.

Cheryl sensed her hesitation. “Look, you come here, I’ll do your makeup, I got some wigs, and some sexy clothes…God knows you don’t have any, and BAM. You are ready for action. Hell, I’ll even take the new guy and you can have Stan, he is an awesome fuck.”

Angela finally relented, it made complete sense. She couldn’t find another good looking girl that she could trust to keep this quiet. A scandal good ruin the company. Besides, Cheryl was right, she hadn’t been laid in a while. She was always so busy with school work and then running to the office.

Besides which, ever since she was 13, Angela dressed like a tom boy; she was embarrassed when her ataşehir escort tits started growing. She hated the way guys would drool over the scantily clad cheerleaders and the way girls would flaunt their bodies at them. She thought it was demeaning on women and she always wore baggy clothes that hid her beautiful 36-22-34 figure. Because of that most of her classmates thought she was a lesbian. After high school she dressed more business clothes, like pants suits. She had her long black hair cut short like an updated 1980’s Pat Banatar style and although she had glasses only for reading small print, she wore them all the time, thinking it made her look smart.

When Angela arrived at Cheryl’s she was going to talk her out of it, but Cheryl came at her so fast, stripping her and throwing clothes at her, she had no time to talk.

When Cheryl was through, Angela wore a long curly red wig, with green colored contact lens, a ton of makeup and a halter top that showed off her firm boobs, a bare midriff that showed off her ripped abs, and a short skirt that showed off her long slender legs.

“damn girl, you are HOT.” Exclaimed Cheryl.

“I feel like I am dressed for Halloween.” Although Angela couldn’t take her eyes off the mirror, she was hot and if she dressed like this more often, she would have a whole other career, she inwardly smirked.

The car Pablo sent drove up to Cheryl’s apartment building and the girls got in the back. Angela was stunned to see the driver was none other but her brother Eric. At first she felt panic that he would recognize her, but he just looked and smiled “hello ladies.”

Cheryl leaned to whisper to Angela, “Isn’t he cute? For helping me out I always give him a blow job on the way home, my way of tipping the help.” She giggled.

Angela rolled her eyes wondering what she got herself into now. She would die if Eric recognized her or if her father found out the she was the second girl. Luckily Cheryl told Angela that she never uses her real name, for the night Cheryl was Chrystal and Angela was Scarlett.

Still, Angela avoided eye contact with her brother even when they rode up the hotel elevator together. She didn’t have to see him, she felt his eyes roaming her body, even with her coat on. Eric, as part of his job would walk them to the door and make sure everything was fine before he returned to wait for them in the car.

Stan greeted them, “Chrystal you look beautiful as always, who is your stunning friend?”

Cheryl took off Angela’s coat and led her into the suite. “Well boys, this is my very very good friend Scarlett.” She said with a wink.

Stan and the other man were hardly boys. Both were in their late 40’s or early 50’s, slightly out of shape and balding. Although Stan stood a good 3 inches over the other man.

“Ah, Scarlett a pleasure for sure, this is my partner in crime, Bill.” Said Stan.

Scarlett shook their hands and it dawned on her, this was Stan Compton and his boss, multi millionaire Bill Wraces. Her father has been trying to sign them up for almost two years. No she had a chance to do it just by fucking.

The lights were down low and Cheryl put on some music. Both men were seated on the couch and she gave each one a lap dance. Scarlett downed a glass of scotch and started loosening up. She also started gyrating to the music, doing her best to match Cheryl.

Stan leaned over to Bill and said “she ain’t much of a dancer, but get a load of that body.” Both men chuckled.

Cheryl whispered to Angela “so which one you want?” Angela told her she would take Bill. He was after the boss and famous in the world of business, why should she settle.

Angela sat on Bill’s lap as Cheryl and Stan went off to one of the suites bedrooms. Bill slowly ran his hand up her arm, he could feel his erection straining against the layers of fabrics between him and her ass. Angela kissed his ear then slowly slid down to the floor, stopping to undo his belt, zipper and shoes.

Bill lifted his ass off the couch to pull down his trousers and briefs. Angela smiled at his average sized cock. She hadn’t had one in around a year, and she was longing to enjoy herself. She also knew she had to make sure Bill enjoyed himself; taking his cock in her hand she kissed the tip.

Bill watched this young beautiful red head engulf his cock and suck it hungrily; her head bobbing up and down over his entire length. Sometimes she would gently scrape their teeth against his sensitive had or stop moving entirely to suck on it,…not gently. The pleasure in Bill’s eyes was stronger as a low groan rumbled through him.

Angela removed her mouth from his cock, leaving behind a trace of red lipstick. She put her arms around his neck as she lowered her body and pressed herself into him, letting her warmth absorb his. Angela’s wet heat ground into his hardness, trapping it between their bodies. Angela pressed her lips to his and her tongue invaded his mouth to play with his.

Placing her hands on his shoulders, her wet pussy kadıköy escort bayan just inches from his hardness, she lowered herself onto him. The first touch of his cock piercing into her was like being struck by a bold of lightning. For so long she ignored her own craving, but now feeling him slide into her body, she had found her lust.

Bills pelvis ground into hers slowly at first the she began to ride him with more furry, the couch creaked and popped. Tidal waves of pleasure and more washed through her, tossing her about like a rag doll in his grip. Sweat rolled down her body and fell from her breasts to run down the planes and valleys of his hairy chest.

At length, one wave larger than another crashed over her and she wailed in pure ecstasy. Her pussy squeezed down on his cock as it exploded pouring his seed into her. They embraced, entwined and gasping for air as she leaned over to the couch and Bills cock came out from the darkness into the cool air. He slumped back as Angela stretched out on the couch, a wicked smile on her face.

Angela grabbed her clothes went into the bathroom to change. Soon they were making their good-byes with Bill passing her a few hundred dollar bills along with his phone number. She returned the phone number to Bill saying “sorry love, I’m on a contract.” She giggled and grabbed Cheryl’s hand.

They laughed in the elevator down and swapped stories. Angela had to admit to Cheryl that she was right and totally happy she came, and came she did.

Outside Eric was waiting for them with the car, but this time he held both the front and backseat doors open. Cheryl squealed whispering to Angela “this is my favorite part, tipping the driver.”

Cheryl jumped in the front seat as Angela sat in the back. She could tell from Cheryl’s motions that she was probably unzipping her brother. She saw Cheryl head disappear into his lap and Angela pretended not to notice and looked out the window.

The darkness of the car played shadows by the flashing street lights going by and Angela looked back up front to see Cheryl still missing from her seat, then she looked at the driver’s rear view mirror, she could see the smile of Eric’s eyes and then they locked on to hers. She felt flushed and jerkily moved her head away back to the window.

Here she was in the back seat watching her brother get a blow job from her girlfriend and he didn’t even know it was his sister watching this. What would he think if he knew? Would he still be smiling and enjoying it. No, how could he, how could anyone? She thought.

It only took nine days for Pablo to call Cheryl and request that she and her girl friend return for another performance for Bill and Stan. It took only three days for Pablo to call Angela and tell him he just signed Compton & Wraces for a $2.3 million investment package.

Seeing nothing but upside, Scarlett and Cheryl went back for a repeat performance. But it took 18 days for the balance of the Universe to turn over.

Pablo had set up another potential investor and called Cheryl for a Thursday night hotel visit. Except Cheryl was sick with a cold and she called Angela to take her place. At first, Angela readily agreed. She knew this client was important. It wasn’t until she was at Cheryl’s place putting on her “Scarlett” outfit and makeup that she realized she was in a jam.

As Cheryl was applying the last of the make-up she said “and remember, don’t forget to tip the driver. Oh you will love it his cock is so big and wide.”

Angela’s eyes widened, what did she just get herself into? She was now going to give her brother a blow job? She couldn’t do that to her baby brother. It more than wrong, it was gross. But how could she get out of it.

“Perhaps”, she thought, “he only likes Cheryl. Maybe he won’t even want her”. She thought about it a bit longer. Who was she trying to kid, she thought, her brother went after any female with two tits.

Angela left Cheryl’s apartment and walked toward the car where Eric was holding the back door open. “Scarlett? Where’s Cheryl?” Asked Eric.

Angela got into the backseat mumbling the word “cold.” Hoping that her brother wouldn’t recognize her voice.

“So you and Cheryl roommates?” he asked.

“Ugh ugh” she grunted in the negative.

Eric tried to make chit chat but Angela played it cool with occasional sighs and hums. A few minutes later, which seemed like hours to Angela, they were at the Hotel.

Going up the elevator she put all that behind her. She had two things to concentrate on, making sure Mr. Lemur was happy and will sign with her dad and secondly, get some pleasure for herself.

One hour later. Mission accomplished, only partially. She was sure that Mr. Lemur would sign up, but her own pleasure was lacking, he was just a bit too quick on the draw and she was still on the edge of lustfulness.

Now on the elevator down she thought about the trip back. She had almost convinced herself that Eric had this arrangement only because of Cheryl, but escort maltepe as she crossed the hotel lobby, she could see Eric holding the front seat door open for her.

Getting into the car she thought she would just play ignorant, after all, Eric wasn’t a rapist. Then again, her pussy was getting moist thinking how clueless he was. He had no idea that his straight laced homely sister was Scarlett, the sexy whore.

“So this job doesn’t really pay, you see I do it for the tips. Am sure Cheryl must have told you right baby?” Eric glanced from the road to look Scarlett up and down with a lecherous grin.

He saw Scarlett wasn’t taking the initiative, so Eric pulled sharply into an ally way and stopped the car. He unzipped his pants and took out his semi erect cock. Scarlett looked at it, it was just as Cheryl said big and wide.

“Come on honey, you know you want it… them old dudes ain’t got nothing like this.” He crackled.

He gently moved his fingers along her bare arms and shoulders and before she could even think about what was going on, his hand was behind her head and her luscious lips parting to allow his cock inside her mouth. She swallowed him deep then withdrew, her tongue washed over his shaft. She moved her mouth faster and faster, sucking and licking.

Angela was enjoying it as sticky saliva drooled from her mouth in torrents. She wondered what this amazing dick would feel like in her pussy. But then that thought confused her, ‘what am I doing?’ She thought. She instinctively started to pull off his cock but he pushed her head downward and immediately exploded a fluid of warmth into her mouth. Angela swallowed it all and could feel her wig shift slightly from his touch. She quickly sat up straight and fixed her hair and wiped her mouth.

“Okay driver…tip paid, lets go.” She whispered.

Eric pulled the car back onto the street and Angela stared out the window. At first disgusted with herself, but that feeling faded away like the paved road behind her. She felt amused. She had just had the most wonderful cock, and her brother had no idea it was from his sister. She felt like she pulled one over on him. That the joke was on him. Soon she felt better and when she arrived at Cheryl’s house, she ran in to see how she was feeling. She was tired and just pulled off the wig, placing it on the stand and didn’t bother change her clothes. She just wanted to get home and take a shower.

Eric had moved the car across the street and down half a block. He wondered if Scarlett and Cheryl were lovers. He sat wondering if he could get them in a threesome one night. Suddenly he saw Scarlett come out from the apartment. She was dressed like Scarlett but she didn’t have red hair and as she turned to get into a car the street lamp caught her face. Scarlett was Angela.

“Holy shit! My sister is Scarlett the whore. My sister gave me a blow job. Holy fuck!”

A thousand thoughts ran through his head while he was driving home. First off his sister was always the favorite, she was the smart one, she was the one that was going to take over the family business, she was always looking down at him calling him a goof off. But his main thought was that he had no idea his sister was so hot. She was always dressing in baggy clothes, he had no idea she was…hot, hell she was on fire. Had he known, he would have tried to bang her when she was still living at home.

Wait a minute he said to himself out loud in the car. I didn’t know she was my sister, but she knew it was me. She gave me a blow job only because she didn’t think I knew who she was.

Eric wasn’t the quickest thinker on the planet and as he arrived home all he could think about was how he was going to trick her into fucking him.

The a couple of days later, Angela went to her classes from morning till about 2 PM where she headed to the firm. She would take the elevator up to the offices; wave her hellos to the handful of secretaries and account executives on her way to her father’s office. Except this time his door opened and out walked Eric. He looked at her and grinned.

“Hey sis, how’s it going?”

“Oh hey Eric, what are you doing here?”

“Oh you didn’t know? Dad gave me a job.”

Angela was a little nervous but she didn’t want to show it. “A job? What kind of job?”

“Oh you know…driving, picking up VIPs and such…you know. After all you gotta know who your hiring these days.” Eric grinned.

“Well good for you, it’s about time you earned yourself some money.”

They chatted a little bit longer then Eric leaned in to give her a brush of his lips against her cheek and he was gone. Angela felt her face blush red. Eric had never done anything like that before. She wondered if he somehow knew, was he hinting when he answered ‘you know’? Impossible, so she gathered the papers in her hand and walked toward her father’s office she dismissed the thought.

Angela stacked the papers and files on the desk, telling her dad about the accounts and investment strategies; however he was a little distracted.

She asked him what was going on and he explained he had client that wanted to see Cheryl tonight but she was still sick. Angela told him to tell the client that and he will have to wait. But her father got up from the desk and paced the office.

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