Quick Encounter with a Prostitute

This is the story of an older man's quick encounter with a young prostitute.

Millie Dynamite

Copyright© 2013/22 by Millie Dynamite

This is a work of fiction and not intended to be historically accurate, but merely a representation of the times. The names, characters, places, and incidents are products of the author's imagination or used fictitiously. Any similarity to any person, living or dead, is merely coincidental and unintentional. Historical characters used are strictly for dramatic purposes.

The driver slowed the car, eyeballing the women walking down the dark street. With his nerves on end, he had trouble finding this part of town, and worried he might mistake an undercover cop for a whore. Four or five women strolled casually on each block. These fallen doves gazed back at him, inviting him to pull around the corner. Most were less than attractive.

Several had bloated bellies, not pregnant but fat. Several were older ladies and appeared worn. Others were somewhat attractive, and their bodies were at least fit with pleasing shapes. Their faces, while cute, painted with thick layers of makeup. They would stare at him and mouthed words with their ruby-red lips. Some pointed for him to turn on the side streets.

This didn't influence him; he just drove on searching for someone who'd catch his eye sufficiently to make him want to pick them up. There were several women he would not mind fucking, but none he saw he believed he needed to fuck. Then he saw her and wanted her, but he did not know if she was a hooker, not for sure anyway. She was young, 18 to 20, well-proportioned, cute face, and dressed like an ordinary young woman, not a whore. However, she bordered the verge of stunning with an athletic body.

Oh, yes, he yearned to fuck her hot body.

She wore a peach-colored top with some anima character which seemed contorted by her medium-sized breasts, and she sported shorts matching her top. Painted on pink form-fitting shorts, which showed a camel's toe in front and a round, perfect hand full of matching ass cheeks behind. Athletic shoes with knee-high socks completed her outfit. A pack of cigarettes was stuffed in the left sock.

Shoulder-length blonde hair, which this woman wore in a ponytail. She appeared younger than her twenty-three years and played the dumb blonde bimbo to perfection. Then she glanced at him, lifting a cigarette to her mouth. The girl took a long, deep drag from the smoke. Coughing and hacking like she had never smoked added to her youthful game.

"She's trying to look tough," he said.

At this point, her eyes locked on his. The girl turned to the side street, pointing. Without hesitation, she walked down the side road, stopped a short distance past the first building, moving to the curb. Her head turned back toward the street he was driving down, and he spun the car down the side street, tires squealing. Pulling up to the curb where the girl stood, he pushed the button, and the passenger side window slid down. The girl rocked on her toes with her hands behind her back.

"What you doing?" The girl leaned into the car, standing on her tiptoes on the curb. Sticking her head inside the window, resting her arms on the opening, "Hi ya, I'm Sandy," she said. And repeated, "What you doing tonight, Mister Cadillac?"

"Oh," he said, "looking around, Sandy. My name is Thomas. Do you need a ride?"

"No, sir, Mr. Cadillac, sir, I need a date. Um, do you need a date?" She asked in her breathy voice, imitating to perfection an actress she'd seen in a movie. She was chewing some gum. After she asked him about the date, she blew a giant bubble, it popped, and the gum spread over her face. She giggled as she cleaned it off her face and put all the gum back in her mouth.

"Well, yes, actually, I need a date." Thomas said, smiling at her.

"Coolioso to the maximums. Cause I need to make money to get a new formal dress to wear to the prom. Do you want to help me out with that Mr. Thomas Cadillac?" The breathy, silken she spoke and her tight outfit combined to rev him up. His cock throbbed from the ache for her.

"Just Thomas, Sandy, no need for you to say, Mister, and my name isn't Cadillac. I can help with your dress. Can you help me with my problem?" He asked, not sure exactly how to phrase it.

"Um, I think I can." Sandy said as she opened the door. She hopped into the passenger seat and shut the door. "Pull down the street a couple of blocks, and there are these two old buildings with a parking lot between them." He drove down the street until he saw the two abandoned buildings. "Turn in," she instructed him, and he did.

"Drive down further," she said, and he kept going further back in the lot. He saw a small opening in the building to the right. "Pull in the space, and your car will be hidden." The waif told him, and he pulled in and inched forward till the car was well inside the opening.

"COOL! We can be alone here!" she told him as she turned to him. "Put some music on." The hooker said, and then she added, "Thomas, Daddy." His head jerked to her. "You look like a daddy to me. You're about my dad's age and more handsome than him."

Of course, Sandy lied through her teeth. She'd never known her father.

The young woman slid over the seat toward him.

It was strange when she called him, "Daddy," the word turned him on more. However, the young woman reminded him of his daughter, which should've freaked him out. The effect was quite the reverse. She moved up next to him.

"You are so big and strong, Daddy," the woman purred as she moved her hands over his shoulders and biceps. He flexed, so his muscle hardened for her. "Wow, Daddy-O, you are strong." With practiced skill, she jacked his ego as her hands roamed his chest, unbuttoning his shirt. With her tiny hands, she caressed the bare flesh of his chest while his tool stiffened inside his pants.

Crawling up his body, her tiny mouth moved to his ear, her tongue ran around his ear, tracing it, and then she darted her tongue all over his ear. Her hands moved to his face, and she turned his face to her.

Now, most whores never, ever, kiss the john, but she did. She pressed her lips to his in a sweet, long, loving kiss that slowly changed to a deep, passionate French kiss, with their tongues moving in and out of each other's mouths.

When they broke from the kiss, his breath was shorter and heavy. He seemed to suck in the air as though no amount of air might fill his lungs. With his chest heaving, the young woman's small hand came to rest on the crotch of his pants. The touch made his dong leap up even harder.

"Daddy is so huge there. OH, my Gosh, it is so COOLIO! Wow, Daddy, you are muscular and strong!" she told him. "Daddy," Sandy said flirtatiously, "Can you help me with some money, please? I mean, before we go any further."

"How much do you think you need, sweetie?" He asked her.

"At least $400 for the outfit I want for my senior prom. It is so cool, and I know Daddy wants me to have the best, right?" She cooed at him.

"Well, $400 is a bit high. I'm not sure Daddy can afford that much." Thomas told her; his eyes appeared as if he was in slight pain.

"Oh phooey, Daddy, I guess takes me back to the street then. I thought you were a wonderful Daddy, not a cheap Daddy." She said. "I mean, I don't want to do bad things with anyone but you, but if you can't help me, I guess I'll have to find someone else."

"No, wait, I can give you $100, Sandy. Sure I can." He said as he pulled his wallet out of his hip pocket and opened it. He pulled out a 50, then a 10, and at last two twenties, handed it to the girl. She quickly put the money in her sock. She could see lots of other bills in his billfold.

"But Daddy-kens, I need $400," the woman said, sulking.

Removing his wallet, holding it to his face, he pulled another one hundred-dollar bill and handed the money to her.

"Well, it'll be a start. Daddy, you're so generous, strong, and sweet." The prostitute's small hands ran over his belly and down to the crotch of his pants. She unbuckled his belt, unbuttoned the pants, unzipped them, and reached into the boxers, finding his rigid member. "Wow, Daddy's huge." She said breathlessly. She bent her head and moved toward his crotch as she worked his small, erect cock-let out of the boxers.

"I've never seen such a giant meat stick," her hot breath moved over his tiny dick.

The idiot believed her when she told him she'd never seen such a giant dork.

He felt her elfin, wet mouth on his schlong and her tongue as it explored his cock. Her head went up and down on his knob and grew even stiffer. She would stop every few minutes or two and tell him something in her breathy way. The young woman told him how strong he was and how enormous his weenie was and told him what a terrific daddy he was. All this fed his lust as she gave him a blow.

"Oh, lordy, baby girl, I really wanted to, umm."

"Daddy wants to stick his dick in me, right?" She burst out in an even more excited manner. "COOL, Daddy, but I'd need more for fucking!" her coy breathiness bored into his ear, enticing him to continue.

He looked down and started to argue, but her sweet young face seemed so innocent he couldn't. He reached into his back pocket again, pulled the wallet out, and removed a $100.00 bill, handing it to her.

Gazing at the bill, "Not very much. And I thought you were generous."

Adding another $100, he held the two bills to her.

The prostitute's lower lip quivered, and her expression changed to disappointment and sadness.

Pulling two more hundred from the wallet, he held the $400 to her.

At once, Sandy's demeanor changed. Snatching the cash from his fingers, the whore put it with the other money as she moved back to the passenger side. With her back to the door, she pulled the shorts off one leg, doing the same with her pink thong.

"Stick me, Daddy, stick me with your ginormous ole daddy dick!" She held a condom in one hand, and as he moved to her, she stopped him and his covered penis. Positioning themselves, he put his johnson at her pussy. The woman was tight, causing him difficulty working his pecker inside her. The experience was terrific. "Oh, Daddy-kins, you're so massive you're hurting me. Only a little." She told him as he thrust inside her.

Only able to contain himself, he feared he'd cum too soon on the edge of climax already. The woman's pussy clutched his boner. Counting in his mind, trying desperately to make the experience last, the man pounded away. Resisting touching her hot, sexy body, fearing he'd lose his load, he concentrated on nothing, thinking about only numbers and how he moved his body.

Niggling at the back of his brain, the thought of her being a virgin tickled his fancy. The worry was, even if he got balls deep, with only 3 and a half inches to work with, he might not break her cherry. Having never done so, he'd love to burst a cherry.

"Stop thinking about that," he thought, back to his numbers.

The woman was beautiful and so much younger than him. Driving hard, her pussy resisting him, he plugged his joystick harder and plunged deeper, going as deep as he might. But the woman's pussy always stopped him short of balls deep. With his heart racing, drawing ragged breaths, his skin alive with pleasure, ants crawling over and under his flesh, the man pushed up higher so he might drive in with more force.

The woman's legs locked around his waist as her hips thrust to meet him each time he lunged inside.

"Daddy, you're so wonderful, even though you're hurting me, but only a little." The fib practiced, and Sandy recited it with fine acting. "Oh, Daddy, you are such a wonderful lover."

With those words, the businessman almost lost his pud. Blocking her words from his mind, the man worked harder, counting back from 100, 99, and 98. Any trick, every trick, he could think of to hold his load inside.

With skill, Sandy pulled his billfold from his back pocket, expertly fished all the bills, and stuffed them in her socks with the other money. Rocking with him, she pressed the billfold back into his hip pocket as he smashed his prick into her.

In no time, he neared completion, and Sandy sensed the impending climax. Cooing into his ear what a fantastic lover he was.

The mark pumped harder and harder as he grew near the event.

She spoke in an almost incoherent breathless Meg Tilly-speak, rapidly saying things and moaning and groaning as she murmured to him. Sweat beads covered his forehead, and as his face turned red, he went over the edge, spewing his seaman into the condom.

Out of breath and spent, he collapsed on top of her.

"Daddy, can't breathe. You're too heavy." Sandy said as she tapped him on his shoulder. He pushed up off of her and adjusted his clothing quickly. Taking the condom off, he pushed the button, and his widow slid down. He tossed the condom out the window.

He redressed himself as the young woman pulled her clothes back on. She opened the door and stared at him as she got out of the car.

"I can take you back," Thomas said, hopeful for a few more minutes in her company.

"Umm, NO, I'll walk Daddy, thanks. Have a good night." And she seemingly vanished. He finished redressing and back out carefully from the cramped space. He then turned and went back toward the street.

Checking both ways, he didn't see the young whore anywhere. Turning, he drove back to the main road. As he drove away, he pondered if she was as young as she appeared. He thought of her tight pussy.

"Virgin pussy," he wondered. "No," he thought, "she fucked too well. Eighteen, nineteen years old? Might be older."

The girl peeked out the window of the old building and watched him leave. Staring at the black Cadillac, he turned north, back toward the better part of the city. Moving out of the building, she walked up the street, still careful. The young woman waited for as long as she could. She wondered how long before he realized she had stolen all his money. For a moment, Sandy pondered if he'd come after when he found his wallet empty. If not tonight, tomorrow night, or the night after that? More than likely, never.

"How much you got, Sandy!"

Sandy turned to face a small woman standing in the doorway.

"I got nearly $1,0000 so far, mom. Mostly from an old, rich perv," she said with a smile at her mother.

While her mother once was a beautiful woman, these days, she appears tired with sad, weary eyes. At one time, Sandy's mother had been happy and carefree. The mileage of fucking for money robbed her of happiness and made her old before her time. Life on the streets would soon steal her daughter's beauty, joy, and hope.

"Haven't had much luck tonight," her mother said. "I only earned about $150 so far. I'm going back out, honey. Don't worry, mommy will get us more. You did marvelous, sweetie." She told the girl as she counted the money, put the tidy sum with her cash, and locked the treasure in the box, safe and sound, placing the box inside their hidey-hole. The mom then twisted the top off the bottle she was holding and took a long drag on it. "Needed some encouragement. Been a fucking, long day, and second wind, don't you know? You want some baby?"

"Sure, mom, I love vodka," Sandy said as she took a swig of the clear liquid. She thought, "A few of these and then back to the street for me."

Sandy worried about her mother. How much longer could she fuck for money?

Blessed, Sandy kept a youthful appearance, while others her age, who'd begun, like her, at 18, already had faces of 30-year-olds. Yeah, for sure, Sandy, at 23 years old, looking like an 18-year-old, was one of the lucky ones.