A lost bet in the gloryhole (part 1)

The new job was good for me, giving me a chance to finally find my feet and secure myself. I dutifully tried my best to adhere to my boss’ strict regime. Things continued like this for a short time, the giddiness wearing off for me, but Tony became more aggressive with each passing day, until he announced a party he would be holding.

“I expect you to help keep the guests entertained, show them a little skin whilst you serve them drinks.”

It’d be an easy task, and I went to practice my sultry walk as the day turned to evening, his friends pouring into his home by the number. The party was a hit, everyone having an amazing time, and despite a few idle gropes and sharp spanks, I found the hem of my skirt brimming with tips before the night was over. 

“Well, well. Someone’s got a purse that doesn’t fit their pants…”

His gruff voice tore me away from my duties, forcing me to crane my head up to meet him in the eye. Even after sitting down, I can tell he’s much taller than me.

“Why don’t we test your luck a little?”

They were playing a simple game of cards, but his smirk tore into my pride, as if challenging my character completely, I couldn’t help but accept. I saw Tony step out over here from behind the counter, so I can assume he’s the one who is most interested in the outcome, and my thoughts instantly swim to how much I can wring out of his friend’s pockets.

“You’re on, old man. Just don’t cry when you pass over your wallet to me.”

I can tell he bit back on those words, and I held my smirk as he left to collect some cards, a crowd gathering at the show. He slammed the deck down onto the table and began dealing them out, the two of us began a flurry of bets, tossing down our money one after the other, each hand having our collective pots growing and shrinking in a stalemate.

A few hands in and my luck begins to turn, a decisive wager paying off, I clean out almost half of his money, and I savour seeing him visibly wince as I pull it over to my side.

“It’s not too late to give up, I know men your age can’t last very long anyway~”

The crowd appreciates my taunts, egging him on to continue, I can see visible anger across his face, and revel in having riled him up to this point. Things continue to sway one side or the other, me staying in complete dominance after my previous win however, and leaving me wanting to take care of things quickly. Even Tony seemed pleased with me, flashing me a smile.

“Alright, old man. I’m matching your remaining pool. Pay up or fold!”

This would likely clean him out, I only had to put up a third of my winnings to clean him out, it was a sure thing! As the cards got dealt down, my heart sank and I felt the reassuring pats against my back turn into mocking slaps, both of us now on equal footing.

“Alright, fuck it. All in, you bitch.”

I was fed up by this point, clutching to a card I had hidden away, I was going to clean this bitch out for everything he had, I was tired of the demeaning looks he keeps giving me. As we toss our cards down, revealing our hands, my heart sinks again, even the crowd grew silent when they looked down at how he had cleaned me out.

The laughs returned however, and I watched him slowly wrap his arms around my money, pulling it over to his side as I began standing up to step away, shivering in anguish of having my tips pinched from me so easily…

“Wait a minute.”

The cold, firm tone of his voice sounded much like an order, and I stopped quickly, returning to my seat.

“How about we put things up for your money, hm? Your outfit, your tips. Deal?”

It was such a bold move that I could barely respond at first, suddenly aware of the lustful gazes people were casting at me, I felt no other option than to agree, the outfit not worth much compared to my earnings anyway.

Things were over in a flash, a single hand and I was forced to strip in front of the whole house, a smack against my ass when I bent over to remove my underwear, looking back, I saw the entire crowd and gave up on finding the culprit, tossing my outfit onto the table before slumping back onto my chair, struggling to hide myself.

“Well, I didn’t expect things to go over that quickly… How about this.”

He continued, a sly grin on his face, but hoped in my heart that perhaps I could still pull things back. I wanted a chance to make these smug fuckers behind me eat their words.

“You put yourself up in one of our walls until you pay your debt back. Get fucked and get paid, easy, right?”

There’s no way I could back away now, I wanted my hard-earned money back, and by the way he described things, I may even make some extra money whilst I’m here~

The crowd had grown silent for a moment, and looking across their faces, it seemed they were all awaiting my answer with anticipation, staring openly at my naked body, and upon glancing down, I could tell that these people would likely be the first to show up behind me…

It was odd, staring at the people who may be using me only moments from now, but there’s no helping what I need from this, and I look up confidently, still holding my smile.

“Deal.”

We were dealt the final hand, the man taking his time with each decision until the climax soon came, the reveal. Already sunk so deep, I barely felt the cut to my pride as he thoroughly trounced me, revealing his winning hand and looking smugly over me as I struggled to hold my smile, stifling back my despair. Not wanting to give in to their jeers, I then turn around at the men staring at me, still covering my body subconsciously, I boast toward them.

“Just bring your money to my stall and be very generous with me~”

However, as the crowd jeered at me struggling to hide my naked body, a few smacks against my ass and lecherous hands groping my tits quickly eroded away at my confidence. I tried my best to hold a proud face as I took my walk of shame, though one particularly hard smack shattered it, eliciting a squeal from my lips that the crowd very much enjoyed.

Even though I knew the stakes from the start, as he coaxes me to follow him to a different part of the house, I can’t help but feel each step becoming more and more difficult. Descending into Tony’s basement, the music and frivolity slowly died down as we made our way over, lights dimming and the sound quickly replaced with…something else. It was as if my mind was screaming at my body to run, to escape my debt and somehow try to make it outside without having my naked body violated in some secluded alley. Weighing up my options, I focus on how badly my luck has served me today, and can’t help but picture myself grabbed from the shadows and pushed up against a cold stone wall, my holes taken by some stranger…

“Here you are.”

His gruff voice snapped me out of my waking terror, my body trembling from the residual thoughts of what would happen if I tried to escape. Casting my glance over to where he was motioning, I realized now what he meant by a ‘wall’. Tony had apparently designated his basement as a sort of brothel…

In front of me were a row of holes, most of which were covered by a tarp on the inside, but a few were already in-use… The wet smacking sounds caused my body to quiver each time they hit my ears, picturing myself there in their place. I listened closer and could hear the muffled squeals from the other side, remembering that they were girls just like me, who had just a little spat of bad luck, and have now ended up like this.

To be continued… Read part 2!