A hands on kind of leader...

Saturday September 12, 2020

“Fuck you asshole!” Jenn shouted out as the car drove away, “Their loss…” she continued but in a soft voice as she reached down and re-jigged her top.

She turned back to the road, but there were no other cars coming at the moment. She could see Debbie standing a few hundred meters farther up the street was having the same kind of luck as she was.

After a few more minutes standing on the street, her phone rang. She opened her purse, rummaged around until she found it and scowled at the caller id. Even so, she quickly swiped to answer and put the phone to her ear.

“Yeah Boss, what’s up?” she said.

“How’s business? You paid for those tits yet?” the rough voice of her pimp filled her ear.

“Nah, these fuckers are really pussies today. None of them have even wanted a blowjob yet!” she said and finished with a huff.

“Bitch, I didn’t pay for those tits out of the goodness of my heart, you’d better get earning some cash today, or I’ll send a car to take you to Tom’s tonight.” his voice was low and purposeful.

“I will Boss! I will!” she replied quickly, too quickly and letting her fear come through in her tone.

“You’d better. I’ll send the car around at 7, if you haven’t met quota by then…” he left the threat linger for a moment and then hung up.

She stuffed her phone back in to her bag and quickly started to scan the street for anyone who might be a John.


“Come on slut, all the way down!” the man said as he placed his hand on the back of Jenn’s head and pushed her downward, his dick pushing deeper in to her throat and she gagged just a little.

“That’s more like it…” he said and held her there for a moment as the shifter of his car dug in to her stomach as she leaned over to give him the blowjob as he sat behind the wheel. His other hand was on her ass, giving it a good squeeze as she had her legs tucked up under herself in the passengers seat.

Then he let go and she bobbed up and down, fast and faster until he release in to her mouth and she swallowed his load until she could suck no more out of him.

She popped off his shaft and smiled, “Mmmmmm… thanks baby, that was great!”, she said as she repositioned herself to sit properly in the seat and folded the sunvisor down so she could fix her makeup.

While she did so he stuffed himself back in to his pants and then pulled out a wad of bills, taking three off of the outside of it, and then reached over and stuffed them in to her top between her tits.

“Awe, thanks baby! Can I maybe get a tip?” she asked in a sugary sweat voice.

“You got more than the tip, now get out and maybe I’ll come back next week.”

“Ok, ok baby, sure thing.” she replied and opened the door to the car and walked down the back ally towards the street once more. When she got there, David was waiting. She quickly wiggled her ass over to where he was leaning aganist the big black SUV that he drove for the Boss and did her best to smile.

“You make quota Jenn?” he asked.

“Awe, come on, that’s not important is it?” she asked as she once more rummaged through her bag and pulled out a wad of bills and handed it to David.

“You know it is, the Boss isn’t happy, and that means if you didn’t make quota, then you gotta get in the car and we’re going for a ride.”

Her shoulders slumped as David counted the bills, “I know, but maybe you could… make an exception, just this once?” she asked, giving her tits a shake as she did so. After all, David was a guy and guys liked her tits.

David finished counting the bills, then walked to the back door of the SUV and opened it, nodding towards it.

She gave out a huff and walked around him, taking a seat in the back as he closed the door behind her.


Jenn stood in front of Tom’s condo’s door, her hands behind her back, her tits pushed out, as she waited for him to open it. When he did he smiled, “Didn’t make quota again, eh Jenn?”

She shook her head and he then waved her in to his condo. As she walked by him he closed the door and then grabbed her ass and then guided her over to the couch but didn’t let her sit down.

Instead he guided her around to the arm, hooked his fingers in to the top of her pants and pulled them down to her ankles. A moment later his pants hit the floor and then with one hand he grabbed a mass of her hair and then pushed her forward over the arm of the couch.

With his free hand he gave her ass a good hard slap, “God, I’ve always loved this ass.” he said as he slapped it again.

She let out a gasp with each one, “Fuck, slap my ass hard!”

He landed several more slaps and then slipped his fingers under to her slippery lips, “You really do get off on it don’t you?”

“God yes Tom, I’m such a slut!”

She heard Tom chuckle softly, then slap her ass again, “I’m sorry, what was that?”

“I’m a slut!” she cried out.

He landed another slap, “A slut? What kind of slut?”

“I’m a whoring slut Tom! A fucking whoring anal slut!” she cried out as Tom repositioned himself behind her and pushed his hard shaft up against her tight asshole.

As soon as his tip touch her sphincter the words just started pouring out of her mouth, “Fuck my whore ass Tom! Use your whoring slut’s tight asshole! Use me like the cheap whore I am Tom!”

With each thrust she begged him to fuck her harder, faster, rougher, deeper. Until finally he pulled her upright by her hair, his cock still buried deep in her ass, and with his free hand reached around and ripper her top off and began slapping her tits as he bounced her up and down on his cock.

It was too much for her, all that came from between her lips was guttural moans and spittle as he released in to her ass and her body jerked from the orgasm that followed.


Tom looked down at the limp body of his ex-wife and smiled, his cum starting to run down her inner thigh and on to the arm of his couch.

Well, he guessed technically it was her couch, or had been at least. She’d been the one with all the money in the relationship and she’d held that over him from day one. He’d put up with it for 5 years, 2 married to her. Now, though, was a different story.

When the husband of one of her friends had pulled him aside before the marriage and suggested getting a pre-nup, he’d thought he was insane. After all, with a pre-nup he’d be left with the same as he’d come in to the marriage with, nothing. But he’d been insistent and even handed him a business card, it was plain and simple, a phone number and the name “The Perfect Divorce”.

He’d called the number and made an appointment, in which they explained everything they could provide in the way of services and he hadn’t believed them at first. But with nothing to lose, as their fees only kicked in if the divorce happened, and then they came out of her assets, he agreed.

The first year of marriage had gone well, at least he thought it had right up until he found her in bed with the building’s doorman. He’d been angry of course, and soon enough she’d filed for divorce.

A week later, he had all of her assets and The Perfect Divorce company was taking care of the rest. A month later they gave him all the details of where he could find her and he’d driven by the intersection several times before he’d seen her. He almost couldn’t believe his eyes, but there she was, looking and acting like a streetwalker in the middle of the day.

And, well, that’s exactly what she was. He’d pulled up and gotten a blowjob from her that first time, she hadn’t been as good as she was now of course, but her eagerness made up for it.

He hadn’t needed to pick her up off the street, as part of his divorce he got full access to her any time he wanted to, and he certainly hadn’t need to pay her. But the feeling of tossing a couple of twenties at her as she scrambled to pick them up, all the while looking like it was the most money she’d ever seen, was poetic justice.

Tom grabbed his cell phone and dialed a number, as soon as it picked up he said, “Hey David, she’ll be ready in 10, take her over to the club.”

“You got it Boss.” David replied and hung up.

He hadn’t been all that mad at David for banging his wife, after all, she had virtually blackmailed him in to it, but still there was a debt to be paid. So when Tom had given him the choice between being fired or “working” on the side as a driver for his ex-wife, well there wasn’t really much of a decision to be made. Especially since Tom let him keep the “Boss’s” cut of her earnings.

Tom pulled out his second cell phone and started typing out a message, “You’re not making enough, time you went blonde bitch.”, he pressed send and a second later he heard Jenn’s phone chirped as it received the message.

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