I had just gambled and lost more than I had to spend in a dimly lit underground casino. I had been on a winning streak and then when my luck turned I couldn’t stop even when I had lost all the money I had. Strangely the illegal casino owner offered to lend me more without having to offer any collateral, “Just on your good looks,” he said and gave my knee a gentle squeeze before slowly running his hand up my thigh. This wasn’t the first time a man had come on to me. I have a big dick and it shows. I wear thin boxers as any other kind of underwear strangles my balls. As my cock swings back and forth, I enjoy the looks I get from women and men alike as they notice the predominant ridge of my cock head pressing against my pants a couple inches lower than most men. I work out and exercise regularly so even at 40, though I’m not as trim as I was in my 20s, I have a solid hairy dad-bod, and I’m not too bad to look at. So I’ve gotten used to my looks and physique opening doors for me. This was that, I told myself, just another door. I didn’t consider what it was I was gambling with and accepted quickly. The owners hand leaving it’s journey up my inner thigh just before he arrived at my crotch to offer his hand. We shook hands sealing the deal. I was desperate to get back to the game, confident that I would soon be back on a winning streak. I did win the first few hands, and then I lost the next, then the next, and the next. For hours this is how It went, a small victory followed by many losses until it was I was again broke.
When I stood up from the table, two men placed their hands on my shoulders, guiding me away from the table, through the crowd and into a darkly lit back room. Once inside, one man took my phone from my pocket, held it to my face until it unlocked. He handed it to the other, who took it and then left through a door on the right. The other guided me in front of a leather padded chair with metal cuffs attached to its back legs and another set of cuffs dangled from short chains at the back rest. It sat facing a leather bench with it’s own sets of cuffs and other metal and leather parts that I couldn’t imagine what uses they held. The only other thing in the room was a large white surveillance camera screwed to the wall with a red light lit below it. That’s when I realized the door that my looks had opened for me this time was not one I ever wanted to enter.
“Can I talk to…,” The man interrupted me before I could finish.
“Strip down to your underwear please, fold your clothes and set them on the bench,” He said while lifting his jacket slightly to reveal a gun in it’s holster.
I removed my blazer and began to unbutton my shirt with shaky hands. The man didn’t look at me as I undressed. He looked almost bored. I wondered how often this happens. How many times has this man taken other men to this room to do this? What were we doing exactly? I asked myself. What was about to happen to me?
“Quickly,” the man said as he reached into his jacket, resting his hand on the gun reminding me who was in charge. I quickly shed the rest of my clothes, placing them in a messy pile on the bench. The man sighed loudly, annoyed that I hadn’t folded them as asked. He grabbed the pile and put them in a black velvet bag by the door.
“Sit,” He said, pressing me into the chair. He then locked my ankles in the cuffs on the back legs. My feet locked under and behind me, forcing my legs wide. My boxers bunched up around my crotch, the shaft of my long, soft cock showed in the gaping hole of my boxers while my cock head was tucked against my large balls, clearly outlined against the thin white fabric of my underwear. My hands were then also cuffed behind and below to each ankle. Locking me back and upright.
“Open wide.” Behind me, I heard the man unzip a zipper. The sound filled the room and seemed to go on forever. In the past, I had stolen to feed my gambling addiction, lied to my wife and son, made some truly despicable choices but I had never thought I would find myself here, about to suck my first cock. Resigned to accept my impending oral rape, I swallowed hard and opened my mouth. The man forcefully inserted a ball gag into my mouth. Relieved, I watched him place an unzipped leather duffle bag on the bench.
“Oh,” he said to himself, “almost forgot,” as he bent to retrieve a blindfold from the bag before securing it around my head, blocking my view from what awful things were coming next.
“Wait here,” He said. Then steps leading away, a door open, the loud music of the casino floor, and then nothing as the door closed behind the man.
It must have been over an hour, maybe two before I heard the same noises in reverse.
"Tom, right? You owe Mr. Trenton a considerable amount of money."
I could only nod in the direction of the man’s voice.
“Do you have those funds readily available to pay us back?”
I could only shake my head no.
“Luckily, Mr. Trenton is a generous man and wants to find a solution to this problem.” I vigorously nodded in agreement. “Tom, I’m afraid what is about to happen here is going to be unpleasant for you but you don’t have any other choice.” I began to panic, twitching against my bonds, breathing heavy and drooling around the gag, my body began to heave. “Tom, calm down, if you vomit you with the gag in you will choke on it and die. That would leave your debt unpaid.” While I tried to calm down, an impossible task, I heard some plastic crinkle then felt a sting in my bicep, then a pleasurable warmth spread through my body. My breath started to slow and I found myself to be somewhat detached from my current situation as if I were watching myself. Oddly I felt my cock give a little throbbing jump in my boxers. Was I into this?
“Much better Tom.” I nodded stupidly in agreement. “It’ll just be a few more minutes.” Then I heard the now familiar sounds of someone leaving through the door I had come in through.
Whatever I had been given left me heady, sinking in and out of consciousness. Visions and images drifted in and out of my mind. I saw my wife on our wedding night, her naked on the bed, breasts bouncing as I thrust into her planting my seed in her tight pussy. That dissolved into her holding our son, Jake in the delivery room, all slimy, new and vulnerable. Then him riding his bike, my hands letting go as he strode forward. I saw my son as he is now, as he was the last time I saw him, sleepily coming down the steps for breakfast in just a pair of short gym shorts. Just 18, innocent and naive but quickly becoming a man. He had no idea about the darkness of the world.The visions so vivid I heard Jake’s voice as if he were right there in the room with me. My brain, foggy and confused imagined Jake coming to my rescue. I imagined Jake whimpering at the difficulty of untying the knots that held the blindfold in place, the first step to freeing me.
Light flooded my dilated eyes, bringing me back to reality. It wasn’t Jake’s fingers removing the blindfold. It was a large man about my age, his naked, hairy body filled my visual frame. Not wanting to look at his face, I looked forward, my eyes taking in the curly body hair that covered his muscled chest and firm but slight paunch. The hair thicker under his navel, it circled his cock which was hard and wet. The tip flushed with color and drooling a stream of pre-cum on my belly and crotch as he leaned in to remove the blindfold. “Wakey, Wakey,” He chuckled and then stepped aside. Behind him, my nude son was hog tied, atop the bench on his stomach, with a gag in mouth, his red eyes, bulging in terror locked with mine. His head was rested on the hairy thigh of another naked man in his mid-fifties. His cock also hard just inches from my son’s face, he stroked my son’s hair.
The man who removed my blindfold, sat down on the other side of my son and gently patted Jake’s smooth, naked butt, making it jiggle slightly. "There he is," he said, gesturing to me. His eyes roaming over Jake’s naked, trussed up body, “Just as promised.”
“Ready?,” The man who had Jake’s head in his lap asked the other man as he held a remote towards the camera.
“Ready!” The man said and the light below the camera turned from red to green.
“Tom, your son is here to help you pay back some of your debt,” The man explained as he untied jakes feet, only to bring them down and cuff them to either side of the bench. Jake’s legs now spread out to accommodate his binds. “He’s going to be doing most of the work but don’t worry, you’ll be chipping in too.” The man ruffled Jake’s hair before cuffing his wrists behind him. The two men worked together to secure Jake’s wrists to a leather belt that snaked through the bench and around Jake’s thighs so his upper body was held in deep arch, his pelvis smashed into the bench, his butthole easily accessible.
“We’re here to help too, so you’re welcome for that,” The other man said as he squatted down, his large ball sack swinging between his legs, his hairy ass spread enough for Tom to see his hairy pink asshole briefly while he removed a part of the bench seat below Jake. Tom felt his cock shift in his underpants. The man reached under the bench and pulled Jake’s cock and balls down through the opening he had just made. “There, wouldn’t want that getting crushed, it’s a beauty,” The man said as he began to slowly stroke Jake’s cock down from the base. It quickly hardened under the man’s touch. Seeing this, the man chuckled and looked at Tom, “Seen your boy’s cock hard before?,” He asked. “Not as big as yours but nothing to sneeze at.” Jake let out an involuntary moan as the man played with his never before touched cock.
“Tom, what is about to happen,” began the other man as he moved himself to kneel in front of Jake’s face, rubbing his leaking cock against the boy’s drooling lips as they stretched into a frightened grimace around the ball gag “is that we, Rob and I, that’s Rob,” he nodded to the other man who gave a little wave with his hand that wasn’t pulling on the boy’s balls, “I’m Glen. What we are going to do here today, is that we’re going to break your boy in,” he said dragging his cock head all over Jake’s face mixing his tears with a slippery trail of pre-cum, “and you’re going to watch.” Pointing to the camera on the wall, “In fact, quite a few people will be watching. That’s how your debt is getting paid.”
I screamed against the gag helplessly as I watched the men molest my son. Glen humped Jake’s face and I couldn’t help but watch. Was this really happening to me? I asked as I noticed, below my anger, was another feeling I wasn’t ready to admit. It must be the drug they gave me I tried to tell myself as I took inventory of the man. He must have been a few years older than me. His body, gleaming with sweat and covered in wiry brown hair was solid and strong. His muscular ass dimpled, his balls the size of eggs swayed with his movements, gently slapping Jake’s chin as his cock, uncut, veiny and thick was left it’s slime all over my son’s face. I felt my own cock swelling, betraying me. My gaze traveled from the leaky cock to Jakes face, hie eyes locked on mine, silently pleading for me to intervene. Glen followed my son’s gaze, looked over at me, noting my thickening cock, gave me a wink. He turned Jake’s face towards me, squeezing the base of his cock, then slowly drew his hand up his shaft to express a large bead of liquid that oozed onto my boy’s cheek. It clung there for a moment before rolling down, looking like a thick tear. My breath hitched in disgust, fear, arousal.
Glen released the gag, freeing jakes mouth. "No, please," he begged, his voice shaking. “Don’t…,” Turning the boys face back to his crotch, Glen pushed his cock past the boys lips and then deeper cutting him off mid sentence. Jake gagged around the intrusion. Glen moaned as he began a slow steady rhythm in and out of my son’s mouth, each time pushing in a little further.
“Enjoying the show?,” Rob asked me as he stood and turned my way. His thick cut cock must have been 10 inches. The weight of it was visible as it slowly swung as the man moved around the bench. Jake’s squirming, young, smooth, captive body bound helplessly between the two dominant older, hairy men was turning me on no matter how much I tried to fight it. Rob let out a low whistle as he looked at me, his hands roamed over Jake's body, exploring. Jake made efforts to move away but was firmly held in place choking on Glen’s cock. The man slowly, but deeply, fucking Jake’s mouth now. Rob took hold of Jake’s head by his hair, pushing his mouth on Glen’s cock until his lips were brushing against the man’s pubes.
“Fuck, that feels really good boy.” Jake’s face quickly turning red as his airway was plugged by the man’s cock. Rob held the boy’s head there for a moment, Jake heaving and struggling for air, before he slowly pulled Jake’s mouth off his partner’s cock. Jake sputtered, gagged, pleaded.
"Please," Jake sobbed, his tears falling freely. Again looking over at me, "Please, Dad, make them stop.” But I couldn’t. I couldn't move. I couldn’t speak. I was forced to be a spectator to the horror unfolding before my eyes. With horror I became aware of my own cock, harder than it had ever been. It didn’t take long before Rob and Glen noticed as well. Glen pushed his cock back into Jakes mouth as he turned to me, a cruel smile on his face. "Watch, Tom. Watch as we break your precious little boy.”
I was watching, I couldn’t look away. I was forced to watch as Glen withdrew his cock from Jake’s mouth, covered with my son’s spit and phlegm it bounced and throbbed as he moved behind Jake. Spreading Jake’s ass, he spat on the boy’s hole and pushed into my son’s virgin hole slowly. Jake screamed in pain. Rob took the opportunity to take Glen’s place, filling the boy’s mouth with his thick cock. My heavy breathing and their groans of pleasure echoed through the room. Jake’s cries turned to sobs, his body shaking with each thrust.
“He’s so fucking tight. Fuuuck, his pussy feels so good. I’m going to dump in him soon.” His pace quickened sending Jake even deeper on Rob’s cock.
Rob moaned, “Hear that Dad?, your son is about to get his first load of cum up his hole.” Glen began pounding into Jake, Jake’s sobs turned into whimpers and then, surprising everyone in the room, moans.
“That’s it boy, take my cock,” Glen growled, holding the boy’s hips tightly, “You like that don’t you?” Rob pulled his cock out of his mouth, a string of saliva and pre-cum stretched out between them.
“Please stop,” Jake begged, his eyes now cast away from mine, his voice a hoarse whisper. “Please…please...”, his pleas turned into low moans as the man behind him punched into his guts harder. I felt my cock burp up a load of thick pre-cum. Glen began to huff and produce ragged moans.
“Before you get too carried away, let’s not forget about dear old Dad,” Rob said to Glen. The man shook his head continuing to thrust into the boy. Too lost in the pleasure of having the virgin cunt stretched around his thick invading cock. But eventually he was able to regain control and nodded in frustrated agreement. A wet squelch filled the room as he reluctantly withdrew from the tight hole. Jake let out a frustrated moan that made the men chuckle. “Don’t worry kid, the show’s not over yet.”
Working together, the men lifted Jake and the bench to bring it closer so that the end with Jake’s head was resting between my spread legs. Jake’s face now hovered just inches above my crotch. Jake and I both noticed that my cock was rock hard now, pushing up against the boxers, my large balls drawn up and halfway spilling out of the underwear’s opening. Wet with pre-cum the underwear had become slick and transparent letting everyone see my cock head throbbing and drooling in desperation at the sight that played out in front of me.
“Dad?,” his voice a hoarse whisper. I tried to look away but Rob standing behind me now, grabbed my chin, forced my head down so that I was staring into my son’s flushed wet face. So close I could feel his hot breath on my crotch. Then Glen released the boys wrists from the bench causing his upper body to fall forward, his face crashing into my lap. I could feel his wet mouth breathing hard against my balls.
“My turn,” said Rob as he moved behind Jake and began to slide his cock in the boy’s trench, making it wet with the spit, juice and pre-cum the other man had left there. Jake involuntarily moaned as the man pushed his giant cock into his violated hole sending vibrations up my balls and cock. The power of Rob’s thrusts as he began moving in and out of my son caused Jake’s face to rub against my cock and balls as he moaned either in pain or pleasure, it was hard to tell now, his wet breath soaked the thin white material, making it cling to my hard cock and balls obscenely. Looking down, his face was covered in the pre-cum steadily flowing out of my cock and through the thin shorts. Glen crouched down to watch the scene as Jake’s face and open mouth repeatedly traveled back and forth against my crotch getting his face wetter while also making my crotch wetter. He involuntarily moaned as Rob continued to stretch the boy’s pussy with his relentless pounding.
“Can you smell him Jake? Your dad’s cock and balls and all that pre-cum?,” Glen asked. Jake looked up at me, his face still rocking back and forth across my crotch. Glen and I watched the boy take a deep sniff of my musk causing another moan to escape, then another, then another. After he got his fill of my scent, he began actively rubbing his face around my crotch as he was repeatedly pushed into it by Rob’s thrusts.
“Looks like the boy likes it Dad,” Glen said as he ruffled Jakes hair. “Looks like you might too. That big cock of your looks like its going to shoot all over your boy’s face any second. Am I right Tom?” He then ran his hand from my lower stomach, just behind my engorged cock up to my hairy chest and across my pecs, pulling on one nipple then the next. I threw my head back trying to stifle my pleasure but ended up letting out a long growl against my gag that didn’t conceal anything. “Nice,” Glen chuckled as he began using both hands to tweak and pull on my nipples. It felt amazing. My whole body felt alive, one big nerve, one big cock.
Just when I thought I might regain control, I noticed my son’s tongue on my balls. He had stopped trying to hide his pleasure, his lust, and was trying to fish my balls out from the fly of my boxers with his mouth and tongue. I looked down and saw Jake watching me, both of us contorted in pleasure. He stuck his tongue out and began running it along the part of my shaft it could reach, still trapped in my underwear now soaked with pre-cum and Jake’s saliva. As his face traveled across my crotch he would suck one of my balls into his mouth, just lightly enough that it would gently plop out of his mouth as Rob pulled him back on his cock. When Rob’s assault pushed him forward he would extend his tongue, trying to curl it around my shaft, seemingly trying to pull it down to get at my cock head. He was openly whimpering now with the delicious frustration of being so close but not close enough. I too had given up and found myself humping up with each thrust, trying to push my cock closer to my boy’s panting mouth. I was going to cum. I knew that. I could hold it back for a while longer but it was going to happen. It was going to happen soon.
“Fuck that’s hot,” said Rob noticing my boy’s mouth desperately trying to catch the whole of my cock, his prize just out of reach. He changed his fucking to a slower rhythm, each thrust punctuated in a powerful deep punch into Jake’s bowels, holding it there for a few seconds then withdrawing slowly until just his cock head was held snug by Jake’s tight cunt. Then he would push in again powerfully. This new rhythm allowed Jake’s hot, wet mouth to spend more time connected to my crotch. Now, he was able to swab my engorged, drooling cock head with his tongue briefly before his face retreated as Rob’s cock retreated. “I’m getting close,” Rob growled.
“You want my cum boy?,” Rob asked as he continued to punch his cock into my son's hole.
“Yes. Give it to me. Give me your cum,” Jake moaned out as he looked at me, his tongue pressed against the sensitive underside of my cock head. I almost lost my load then. Rob’s movement began to become frantic, his breath ragged.
“Now hold up, Jake. We better ask dad’s permission first.” Glen teased as he jerked his cock, “Ask your dad if Rob can cum in you, if he can cum inside his son,” Glen commanded as he grunted and huffed, getting off on watching father and son share this delicious humiliation.
Jake looked up at me, his face a wet mess, his mouth open and panting, moaning, lost in pleasure and lust. All innocence fucked out of him, raped from him. Grunting with the impact of each of Rob’s thrusts, he asked, “Please Daddy, can he cum inside me?”
Moaning against my gag I nodded my head. Hearing and seeing this was all it took. Rob howled out as he pushed balls deep in my boy, filling him up with hot cum. I also lost my load. Cum bubbled up through the fabric of my shorts in large wet globs that Jake eagerly rubbed his face and mouth against as he moaned loudly. Trembling as he sprayed his own cum on to the floor below, splashing my legs and feet.
“Fuck!,” exclaimed Glen. Standing quickly, he aimed his cock at Jake’s face, shooting out five long ropes of cum that coated Jake’s face. Pearly globs of it settled into the corner’s of his eyes, sticky webs of cum hung from his eyelashes to his eyebrow. When Rob stumbled back, pulling himself from Jake’s hole, wet splats were heard as cum dripped out of my son’s gaping hole on to the cement floor. Sweating and panting, Glen found the remote and lifted it toward the camera. Its light went from green to red.
A door opened behind me. Mr. Trenton whistled softly as he walked around into my view. He, ran his hand across my chest, wet with sweat and drool. “Tom,” he began, moving from me to my son. He reached down with a finger to push some of my or Glen’s cum from my boy’s eyes before he began to run his hand down Jake’s bound and naked body until it came to rest on one of the boy’s butt cheeks. He winked at me as he gently pried the cheek away from the other enough to assess Jake’s ruined asshole before continuing, “You’re debt is now considered paid.” Then clapping Rob on the back as he sat panting from his efforts, “Rob and Glen here will take you upstairs to get cleaned up and get some food. How about a massage and a soak? You two have earned it. You can rest in one of our suites as long as you like before we get you back home safe whenever you’re ready. Unless, Tom, you would like some additional funds so you can return to the Black Jack table?”
