Madam and the homeless – Pt. 1

Mike was freezing. He was rummaging through a dumpster, stretching uncomfortably, which caused his worn-out jacket to ride up, letting the cold seep in. It was a truly damp and chilly morning. Winter was already making its presence known. What would Mike’s first winter on the streets be like? He didn’t know, but he had done everything he could to survive it in good health. He had bought plenty of blankets, a few self-heating pads, and secondhand warm clothing—anything his meager finances allowed.

Mike wasn’t your typical homeless person. Just six months ago, he had been a real estate entrepreneur. But a few bad decisions and a handful of loans had broken him. Banks refused to lend to him anymore, and he made what was perhaps the biggest mistake of his life—borrowing from a loan shark. After that, it was literally a matter of life and death, and he had no choice but to sell everything he owned: his car, his house, everything.

It was enough to pay off the loan shark, but he still had massive debts to the banks. Fortunately, he found a job—poorly paid and miserable, but unlike his colleagues, at least he had some income. He was what they called a “secret homeless” person. He had to give his employer a fake residential address; otherwise, he wouldn’t have gotten the job.

He even managed to find decent “accommodation” under a bridge, where he lived with an older friend Henry, who gradually initiated him into the life of the homeless. It was Henry who told Mike about the promising dumpsters near a Prague supermarket—but also warned him that the competition there would be fierce.

And he was right. The moment Mike arrived early that morning, the local veterans tried to chase him away. One even wanted to fight him, but years of homelessness and drinking cheap boxed wine had taken their toll. After a single punch from Mike sent him sprawling to the ground, the man slunk away and left the newcomer alone. This small victory pleased Mike. And so, he now searched the dumpsters for treasures alongside the others.

He watched the cars and the satisfied shoppers pushing their full carts. Yeah, there had been a time when Mike shopped like that too. Once a month, he used to drive to a similar supermarket with his younger girlfriend (who, of course, left him immediately after his bankruptcy) to fill a cart with food, treats, and wine. Nostalgically, he remembered paying at the checkout with $100 bills, proud of himself as others gazed admiringly at the sheer amount of stuff he could afford—and at his petite, fair-haired girlfriend hanging off his arm. And now? He stank and fought with other poor souls over garbage. Hardship teaches you humility.

He had to admit that Henry, his seasoned friend, had been right. The dumpsters were full of expired food that was still perfectly good. There was even vacuum-sealed fruit. Fruit—and therefore vitamins—was a jackpot on the streets. Many homeless people lost their teeth due to vitamin C deficiency. Never mind that some of the fruit was a little bruised; Mike took everything, stuffing it into two large canvas bags. He and Henry would feast tonight! Maybe there’d even be leftovers for the other residents of their bridge.

If only security didn’t chase them off. Once, when Mike was still new to dumpster diving, guards had jumped him and beaten him so badly he couldn’t go to work the next day. For those young security thugs, it had been great fun—they didn’t just beat him with batons; they even pissed on him.

Luckily, he didn’t see any cameras here behind the supermarket, and it was quiet. Occasionally, a supply truck drove by. Still, he scoped out an escape route just in case. Security probably wouldn’t bother chasing him—they’d go after his slower, less agile colleagues instead.

Mike’s peaceful scavenging was interrupted by the faint sound of an approaching car. “Cops,” flashed through his mind. His pulse quickened. He lifted his head from the dumpster and warily looked around. But it wasn’t the police. At the far end of their “homeless dining hall,” about 60 meters from Mike, a luxurious wine-red BMW came to a stop. “Who’s looking for what here? And why would anyone stop?” Mike wondered. A small crowd of homeless people gathered around one side of the car.

Mike couldn’t see much, but it seemed like a hand from inside the car was alternately shooing some away and beckoning others closer. He was about to grab his bags and slip away via his escape route, but curiosity got the better of him. So he watched.

Now, only two chosen individuals remained by the car; the rest returned to the dumpsters. The two stood about two meters from the rear window, and—would you believe it—they started hugging and kissing! Yes, two old, grimy homeless men pressed their bearded faces together and kissed.

Mike heard a faint woman’s laugh from the car. It was clear the two men weren’t exactly kissing voluntarily. After a moment, the woman said something else, but it was too far for Mike to make out. The two men, however, understood. Mike’s eyes widened as they began pulling down their pants in the cold.

One leaned against a low brick transformer box and presented his hairy backside to the other, who—already furiously stroking himself—approached from behind and, to Mike’s simultaneous disgust, shock, and horror, began fucking him!

Mike stared in disbelief. And the reactions of the others? Some ignored it; others glanced occasionally but didn’t seem surprised.

The “bitch” homeless man hung his head, resignedly enduring his companion’s thrusts. The active one, however, was clearly enjoying himself, his moans reaching Mike’s ears. After about three minutes, a loud groan announced that the top had finished inside the bottom. “This is insane,” Mike thought, bewildered.

When the involuntary gay lovers separated, a hand from the car tossed two bills ($10 total) onto the ground in front of them. The BMW immediately drove off. The two poor men each picked up their share, and as if nothing had happened, the active one returned to the dumpsters. The disheveled one wandered off to the grass and began cleaning the unwanted seed from his rectum.

The BMW was now approaching Mike. He didn’t know what to expect. Part of him wanted to see who was inside, but fear won out, and he turned to face the supermarket wall. He heard the car slowly rolling past. The moment stretched unbearably. Then it stopped.

Mike’s pulse spiked again. He could hear his own pounding heart, heat flooding his body. What now? Should he turn around? The sound of a window rolling down. Then a woman’s voice:

“Hey, you. Want to earn ten bucks?”

Mike turned and looked at the architect of this proposal. She was a well-dressed woman in her thirties with short blond hair.

“What do I have to do?” Mike asked. Mentally, he slapped himself the moment the words left his mouth. Was he some kind of servant? Was he really this desperate? Why didn’t he just tell her to fuck off?!

“You’ll jerk off in front of me. You’ve got one minute,” came the uncompromising reply from the car.

Mike was too shocked to think. His inaction was broken when the woman pulled a $10 bill from a magazine on the seat beside her and waved it pointedly.

“Well? Are you in?” she pressed.

“Uh… well…” Mike stammered, nervous and flustered.

Ten bucks wasn’t nothing in his situation, but he wasn’t that desperate yet. Plus, he had two bags full of food—he was set for a few days.

“Fine, I’ll give you… twenty bucks. Hmm?” she countered, flipping through Vogue magazine. As she did, Mike noticed what looked like banknotes tucked between nearly every page.

“Alright,” Mike said, surprising even himself. “I’ll jerk off in front of you… in how long did you say?”

“One minute,” she replied, then added maliciously, “But I’ll time you. If you don’t finish in time, you get nothing.”

That was a challenge. Ejaculating in one minute, in this cold, in this nervous state? But easy money was easy money.

Mike unbuttoned his pants and pulled out his shriveled member. The woman lit a long, thin cigarette with a gold lighter.

“Now!” she announced, starting the race against time. She alternated between watching Mike’s frantic stroking and the dial of her luxury watch.

Mike struggled just to get hard. He kneaded his balls while counting the seconds in his head.

“You’re new here, aren’t you? Haven’t seen you before,” she remarked casually, as if trying to distract him. He ignored her and kept jerking.

A glance into the car: she exhaled a stream of smoke, checked her watch, and announced, “Twenty seconds left, stroker.” She smirked slightly. The sight oddly spurred him on.

“Ten… nine… eight…” she began counting down.

Mike knew he’d make it. At “four…” he triumphantly ejaculated onto the asphalt. And since he’d saved up, the amount was impressively large.

The woman leaned out slightly to inspect the splatter. She flicked her half-smoked cigarette out the window, then smiled at Mike, who was still squeezing out the last drops.

She handed him twenty bucks. “Hope I’ll find you here again tomorrow,” she said in farewell, then signaled the driver to leave.

Mike watched the car drive off for a long time. Then he tucked himself back in and looked at the mess on the ground. Nearby lay the unfinished cigarette. He used to smoke, but after ending up on the streets, the habit had faded. Still, he picked it up now—not for the nicotine, but because he was overcome by a strange sadness, or something like it.

He grabbed his heavy bags and headed for the bridge. He wanted to tell Henry what had happened.

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