A lost bet in the gloryhole (part 2)

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Dejected, I look over at Tony, who doesn’t reciprocate, staring coldly at me as if I was a criminal. I had fucked up in his eyes, and I could tell he wasn’t going to let me out of this.

“Alright, pop your head through here and it’ll hold you still…”

His words were so mechanical, like he was finalizing a trade deal for his stock, and in my catatonic state, he manhandled me much like it as well, moving me around roughly so that I’m standing in front of the hole. Now closer to them, I can hear the squeals much more defined, and I realize that one of the girls is enjoying her place here, and after looking over, I can spy a plaque with her name on it, and even a little drawing of her face, sticky with cum…

“Her? She was like you a few months ago, but she begged me to let her stay here.”

The emphasis on his words sent a shiver down my spine, actually suggesting that someone could enjoy being held like this, it had to be a lie, but with each smack of the thoughtless stranger into her petite backside, her moans seem ever-more genuine.

Not left with any more time to think, I felt a rough hand push against my back, forcing me to bend over and face my new role head-on, seeing onto the other side and noticing a lot of foot-traffic between the squealing girls already in place. Terror once again shook across my body, though I couldn’t deny a slight glistening between my legs as I’m forced to listen to the other girls service their customers, whimpering and moaning with each thrust. It left me with conflicting thoughts, both how I wanted to try my chances, push away the man behind me and make a break for anywhere else, but also that it may be best to succumb to my evening here…

Given no time to think, I feel the man’s rough hand spread a fiery pain across my cheek, smacking my ass with enough force that it caused me to lurch forwards, sending me through the hole and out the other side. In an instant, my body was clamped into place, my exposed rear on full display as I instinctively tried to wriggle out, effectively putting on a show for whoever may be behind me. 

My worries were quickly answered, a familiar smack cracking across my ass again, only this time it was followed by a warm, wet sensation spreading across my pussy. His grip was unmistakable, the man I had lost to only minutes before was holding onto my cheeks, gripping them so tightly that the intense pain caused me to squeal, attracting the attention of onlookers who began to stare.

From the other side of the wall, I can hear his voice shouting out to me.

“I wish I could see your face, bitch! But we’ll see how long a ‘man my age’ can last!”

Without any more warning, I feel his warm, wet tip push inside of me, instantly stretching me out painfully as I struggle to accept him. The numerous faces in front of me watch as my face twists in a mix of pain and pleasure, and I notice the woman next to me, the live-in slut getting her throat pounded. Looking up, I meet the gaze of the man fucking her face, staring down at me as his pace increases, and I realize why. He’s getting off to watching me get fucked out of view!

“Fuck off, you perv! Pay up or look somewhere els- Ah!

My objections were cut off when I felt the man behind me finally bottom out, thrusting every inch into my quivering hole, leaving my breath caught in my throat. Looking to my left, I watch as his cock rapidly pounds into her poor throat, looking at the slobber dripping onto the ground, I watch as he suddenly pushes into her gullet, looking up and staring at him once again. I could hear it, his load being pumped down her throat as he used my suffering to get himself off, the perverse pleasure I took from this was only amplified by the man’s rough thrusts starting.

It was as if he was trying to shove me through the wall with each thrust, painfully fucking me, pounding my hole with what felt like every drop of frustration he had built up during our game, and deep down, I felt like I deserved it…

That’s when I spied them, the familiar faces from the crowd who had watched my downfall began pouring into the room, pointing me out as they adjusted their pants to reveal their cocks, stiff and ready to assault me. All at once, they began surrounding me, jerking off to the sight of me rocking back and forth in my prison, knowing what was happening behind me, the first man took his step in front of me, smearing his cock across my lips as I feel the clink of coins hit the bottom of the bucket beside me.

It was as if a hidden switch was flipped in my brain, the notion that I was getting paid for this, another step toward my freedom, I readily parted my lips and let him slip into my mouth, feeling the taste of his cock spread across my tongue as he began thrusting his hips forward.

Each thrust made the next easier, my body settling into the rhythm of being used like this, but the man behind me was making sure to break me in properly, painfully stretching me with each thrust, feeling my arousal building quickly, I try to deny it from myself, but it’s impossible to hold back. As I look up at the numerous eyes staring down at me, I feel my eyes roll up, losing control as my body begins spasming in my prison, cumming as the man who beat me down also tensed up, gripping to me tighter as his cock began pulsing his load into my once-tight hole.

“Fuck, look at her face!”

They watched every moment of it eagerly, the smug demeanor I held only minutes ago had been shattered so easily, even I felt it, and sighed around the stranger’s cock when I felt the man’s shaft pull back from my pussy, leaving me feeling empty, yet relieved. That is, until it’s quickly replaced, the next person seeing how roughly he treated me and deciding to follow suit, opting to skip straight to the frantic pounding, my twitching body still struggling to recover, I can’t stop myself from moaning lewdly around his cock.

It was then that I felt the first of many loads explode in my mouth, filling it to the point that I had to gulp his cum down to avoid it spurting from my nose, leaving me feeling full. His friends were only too happy to take his place, grabbing a fistful of my hair and lifting my face up, making me feel ever-more like a cheap whore they had bought. The clink of coins is the only thing I can focus on as their motions blend together, my body and mind succumbing to the pleasure.

At the end of the day, my body is aching, my mind is exhausted, and any pride I held onto had long-since slipped away. As cum trickled out of my over-fucked holes, I could hear a set of footsteps come to my hole again. My tired head cranes up to see the familiar, Tony’s smug face sending a chill down my spine, smiling down at me and what I had become, sending a perverted shiver of arousal across my body as I took pleasure in it. I had become used to the disgusted gaze people cast down at me, it felt as if I could cum just from that alone, and I instinctively parted my lips, ready for him.

“I’m not here for that, whore.”

His words cut deep, not as an insult, but because I knew it was the truth, it was what I had become…

“I’m here to collect your tips and subtract them from your debt.”

My eyes lit up, a glint of hope that reminded me that I wouldn’t stay here until I broke, it wouldn’t take long to pay everything back, especially after how much I made! He kneels down with a separate bucket, tipping the coins into it before standing up again, shaking his head.

“Damn, you didn’t get a single tip… You must not be very good at this, hm?”

His nonchalant tone betrayed his words, blatantly lying, I object as he begins to walk away.

“Don’t talk shit, you can see how much I’ve made right there!”

He turns around, walking back toward me slowly before peering down at my bucket.

“Looks empty to me…”

My body went cold, my face growing pale when he turned around again, silently walking to the girl next to me, doing the same to her bucket, only not having to speak with her. An overwhelming sense of dread spreads across my chest when the realization hits. She never wanted to stay here… he kept her here… she was just like me…

My restraints began feeling exactly like that, restraints. I struggled desperately to break free, but there wasn’t even an inch to budge! Tony’s home grew quiet, Tony having likely retired to bed, we were left there together, her having long-since passed out from exhaustion, I followed suit soon after, stifling back a few tears as I dread the next morning, one that many more would follow.

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