I had dug myself into a hole, I knew if I picked the right games to bet on I could dig myself out. I am sure this is what every degenerate gambler thinks, but that doesn't stop us.
My gambling addiction was getting worse; I was in the hole for $5,000 to Angela Castardo or Angry Angie. All I needed was the Bronco to beat the Steelers on Monday night football and cover the spread, and I could repay half the $5,000. Broncos were up by two and to seal the game they were going to kick a field goal breaking the 4 point spread. Then it happened, “Dink!” the ball hit the post and goes far right, I thought I was going to throw up. With that, I ducked out of the bar as quickly as I could and tried to hide from Angie.
A week later, I was at a card game trying to make up for the hole I was in and was down $2,500 to Rocco; things were not going my way. The door opened, “You mother fucker!” I knew I was dead; Angie looked ready to kill me on the spot. Rocco talked to her a little bit, two guys grabbed me and brought me into the bathroom. I pleaded with them. Angie told me, “You have until the end of the week to get me my $7,500, you have until the end of next week to get Rocco the $2,500 and your going to pay interest of $250 to Rocco and me for putting us in this position.” I thought I caught a break until one of the guys grabbed the back of my head and smashed it onto the toilet seat, I blacked out and then came too.
I quietly left the card game. I was panicked. I tried to call everyone that might lend me the money. It was Friday morning; I had come up with $5,000. I was calling around when I heard a loud knock at the door. I panicked and checked to see who it was; it was just the FedEx guy delivering a package. I went to open the door, bent down to grab the package when without warning, I was pushed back into my house. Two guys pushed me back like a bulldozer into my home. I got the money I shouted. Angie walked in behind them, “Glad you got the money because I’m dressed far to nice for what I’d have to do with you.”
I grabbed the envelope, my heart was racing, she looked at me, “it feels a little light?” “Count it,” She said to one of the guys. “Listen here you little prick, Angie doesn’t fuck around, I do the fucking, but I don’t get fucked, you understand?” I nodded my head. The guy looked at her, “$5,000, Angie.” She nodded her head, and the two guys started to beat the shit out of me. She made a few phone calls.
“It's your lucky day; I got someone willing to settle your debt.” With that, the two guys grabbed me and threw me into the car. We arrived at a warehouse. It was empty; no one was around. I pleaded not to kill me. She laughed, “If it’s too much to handle, I can kill you if you ask nicely.” What the heck did that mean? I heard a few cars pull up.
A few old guys wearing suits pulled up, another car pulled in with some women dressed nicely, they talked to her. Two tall Spanish women were there too, they spoke with her as well and exchanged some money, the old guys gave an envelope to Angie. “Strip down you prick, let’s see that little cock of yours, get on all fours!” She exclaimed. Oh god, I was going to have to do sexual favors for these old guys, I was nauseous. One of the Spanish women walked up to me and told me not to move. She reached under me, I felt a cold metal slide over my cock and balls, followed by cold metal sliding over my dick. There was some contraption on my cock, squeezing and restricting my cock.
The two Spanish ladies started to undress, Angie held in her hand a giant dildo with a harness. The Spanish women have big fake tits, and they slowly lowered their pants. I realized they were not women. In broken English, one of them said, “Chu like.” She giggled, Angie spoke up, “My god John look at this, size of those dangling cocks, they ain’t even hard, and they got to be two to three times as big as yours.” The two girls approach me, “Stroke the ladies.” Angie said. I took a gulp and reached forward. I had never held another man's cock before; it was spongy and soft; the skin slid up and down. I looked up, the two Spanish transsexuals looking down with a smile.
The one to the right of me was thick and soft; my hand couldn’t quite wrap around its girth. The one to the left was narrower, my hand gripped it, but it was longer than the other one and curved upward. Mesmerized by these large members and the predicament I was in I just kept jerking and looking up for instruction. “Open wide for Mariana and Julia, the quicker you get this done, the easier it will be for you,” Angie instructed. I opened my mouth and stuck my tongue out, the two girls giggled and slapped my face and tongue with.
Their cocks were now hard, Mariana had the medium-sized thick cock, it must have been about 7 inches, about two inches longer than mine but thick, about the size of Redbull can, her head was even thicker like a fat mushroom. Julia’s cock was at least 9 inches, narrow head, a wide midpoint that curved upward. I focused on getting Julia’s in my mouth, I had never sucked a dick before, but I knew I couldn’t get Mariana’s cock in my mouth. I started off bobbing up and down may two to three inches on her cock, I firmly grabbed Mariana’s cock and stroked it. This continued for a few minutes before I felt a hand on the back of my head push down further than I imaged I could go. “Suck that fucking cock you degenerate bitch!” Angie shouted.
Without warning I gagged, the curve in her cock slammed into the back of my throat, I choked and gasped. The hand released. I teared up, choking, and then the cock was forced back into my mouth. I released Mariana and tried to concentrate on not choking. My head was now being forced up and down; loud gargling sounds were emitting from my mouth, saliva ran down my face. “I got this,” Julia exclaimed. Grabbing the sides of my head, I looked up; she smiled, “Ready?” With that, she started thrusting, holding my head in place tight, I choked repeatedly. I was only about halfway down initially before she picked up the pace. Finally, I felt it; her cock was moving into my throat, forcing its way further and further, I was holding onto her for dear life as she face fucked me hard.
I heard the sound of rubber gloves slapping on, I continued to try and survive the assault Julia was giving me. “Pick that fucking ass up, arch your fucking back,” Angie instructed as I felt my cheeks being spread, the cool gel was circling my hole. I bucked forward as Angie drove a finger without warning into my virgin ass. Julia finally let up, I choked and caught my breath, Angies finger was drilling in and out of my ass. “Open wide,” Mariana exclaimed as she firmly gripped my head and pulled me toward her cock. I looked up, tears streaming down. I struggled to get her bulbous head into my mouth.
She forced it in as Angie forced a second finger up my ass. The uncomfortable feeling of pain from my ass and the size of Mariana’s cock was too much, as I jolted forward her cock slammed into my throat. I gagged and pushed off, before her cock could even leave my mouth I threw up, the small amount of space between my lips and her cock shot whatever was in me out. Everyone laughed, I just sat there throwing up to the side. “Choo big?” Mariana asked, I looked up defeated as she firmly grabbed my head and guided her cock back inside. Every thrust was followed by gagging; her dick would not fit in my throat, which was now sorer than ever. A third finger went in; three fingers were now finger fucking my virgin hole.
With a hard-ass slap, Angie exclaimed, “Let’s see how his ass holds up?” Julia positioned herself behind me. I shook my head; I couldn’t take that. I tried to say no, but I gagged harder. Lube liberally poured down my ass, and Julia pushed her fingers into my ass and slathered her cock-up. Julia was now circling my virgin rosebud with something other than fingers as she knelt behind me. She spits right on my hold before making her mark with her cock, her head now pushing against my defenseless ass.
“I’m going to make him mine,” Julia said, Angie laughed, “Open that virgin little boy pussy.” Julia applied more pressure, grabbing firmly onto my ass cheeks. Then it happened, a few inches forced it’s way into my virgin hole. I jolted forward choking on Mariana cock, the two girls spit roasting me laughed. She held her cock in place, waves of pain shot through me. Mariana picked up the assault on my face. Julia repositioned herself, pulled her cock out and forced it back in. Now she was picking up the rhythm, her cock pushing further and further into my bowels rearranging my insides.
I was being fucked on both ends, Julia was drilling my ass, Mariana was choking me with her cock. With a hard thrust I teared up, Julia’s pelvis slammed into my ass cheeks having fully claimed my ass. From virgin, to taking a 9-inch cock, I was ravaged. The two of them created a rhythm, one cock would pump in while the other with pull out, and the motions would continue. I was on my hands and knees trying to hang on. Mariana pulled out, “My turn on that ass!” She said to Julia, I protested, “too thick.” Angie slapped my face, “Don’t you fucking tell my girls what to do, now clean Julia’s cock off for being a disobedient cum slut.”
The two girls swapped, I could hear Mariana slathering lube over her ass. “Flip over.” I laid down and rolled over; no energy was left in me to flip. Mariana grabbed my legs and lifted them, I looked down at my caged little cock as she laid her thick cock on top of mine. “See how pathetic and small your fucking limp clit is?” Angie exclaimed. Mariana held one leg up and slid her cock up and down my ass crack; she spits down my crack before positioning her head against my swollen hole. I immediately scream in pain as her mushroom head forced its way passed the initial entry, she grabbed my other leg up before applying her weight. I looked down, her soda can size cock was slowly disappearing, I squirmed feeling like I was going to rip apart. “stop, stop, it hurts, stop!” I shouted. Everyone ignored me, her cock forcing it’s way further in, she pulled out before pushing back in.
Sharp waves of pain shot through me; I blacked out briefly from the pain before coming to. I looked down her hips were now against my cheeks. That’s when her assault started, picking up her body and slamming her cock back inside me. She positioned on top of me, her weight bearing down on me, she worked her hips drilling my wreck hole. Julia now positioned herself next to me, I looked up at her she presented her cock to me, I could smell fecal matter and almost gagged. She pushed into my mouth, a foul sour taste at first before she pushed her cock into my throat.
Loud claps and gargling noises filled the room as the two girls were fucking me like there was no tomorrow. Mariana fully pulled out, “Look at that fucking gaping hole!” she exclaimed spitting deep into my bowls through my stretched ass. Without mercy, she immediately forced all seven inches into me, pounding me hard than before. Her hands now placed by my ankles spreading my ass and pushing my leg further over me. All I could do is take the pounding, Mariana was moaning and drilling.
“Oh, I am going to cum!” She exclaimed. Julia pulled out, Angie came over, “Tell her you to want her to breed you pathetic sissy ass, tell her you want her cum deep in your sissy boy pussy.” She slapped me, “Cum for me Mariana, fuck my sissy boy pussy full of your seed, breed my virgin hole!” Angie smiled, “That’s it cum slut, tell her to fill your little cum dumpster up, tell Julia you want her load deep inside you too, tell her you’ll never be a man again after they breed your new pussy.” I now was holding onto Mariana and looking her in the eyes as she pounded me like a woman. “Breed me, fill my me up like your little cum dumpster, I want both of you to shoot your load into my belly, I want to feel your warm hot cum deep inside me, turn me into a woman, make me your sissy bitch,” I said to her.
She let out a loud grunt and thrust me off the ground, I felt a shot of hot cum shoot deep inside me. It was a weird feeling, halfway up my ass a transexuals cock was exploding into me, what felt like a gallon of cum spewed inside me. Mariana collapsed onto of me, our bodies covered in sweat, she lifted up, Angie grabbed my cheeks, the cum started to flow out of me. It was abruptly plugged by Julia, who shoved her cock into my swollen cum filled pussy. She lifted my legs up and just fucked me like a woman, grunting loudly, her hips making a loud clapping noise against my ass.
Mariana circled and pushed her limp cum and ass juice covered cock into my mouth. I opened, it was easier this time as it wasn’t hard, I sucked whatever cum she had out of her. Julia was relentless, my cock was jumping, restricted by the cage as she kept hitting my spot, I was moaning and panting. Mariana pulled out, “Filled me cum dumpster pussy, breed me.” She grabbed my throat, choking me, “Take this fucking cock, I’m going to cum into jur ass, tell me chu want it, baby.” While coking I exclaimed, “I want your cum, breed me baby, my ass pussy a cum dump.” She grunted several times, pounding hard and harder, without stopping she shot her load deep inside me, I could feel the cum slide out through the sides as she kept pounding away.
She slowly lifted her self up, Angie came over, “Flip over, on your hands and knees, fart that cum out of you!” I slowly tried to get up, wabbling at first, then getting into the position. I pushed and felt all the cum slide out of my ass, cum bubbles formed as the cum slid down my legs. Angie grabbed my head and spun me around, “like all this shit up.” A mix of ass juice, cum, blood and fecal matter had pooled on the ground, I licked up as much of it as I could.
“See now you won’t be owning Angry Angie money again now, will you? To make sure get on your back.” I noticed Angie was wearing the big strapon I saw earlier, it was longer than Julia and thicker than Mariana. “Please, no?” She slapped me, poured lube on the big dildo and positioned it, without warning about half of it was inside me, I gasped out in pain, the hard rubber didn’t accommodate the same way the cocks did. She lifted herself up and just pounded me, forcing it inside me, relentlessly pounding away.
“Suck Julia’s cock clean again, slut!” She ordered as I took her pounding. Julia knelt again, I took her limp cock in my mouth and sucked her as best I could. This fucking hurt, she was destroying my ass with a monster dildo. She pulled out and slammed it back in, the rubber balls slamming into my ass, she repeated this over and over again, pushing my legs higher over me crushing me. She pulled out let go of one leg and shoved three fingers inside me effortlessly, then slipped a forth in. It felt like she was trying to pull my ass out, then she did it, she positioned her thumb, and with an excessive force, I felt like I got ripped in half. Her whole fist was now inside me, she pulled her whole hand out and started to punch fuck my ass. My ass was swollen and destroyed; it had no resistance now. She pushed her fist in slightly past her wrist pushing up against the front of my crotch.
A wave of pleasure shot through me, she just kept messaging that, Julia slide her cock out of me. “Oh, my god, Oh fuck,” I panted. “That’s it, I’m going to make you cum like the little sissy you are!” She exclaimed I felt pressure building all of a sudden it released. Waves shot through me as I spasmed, cum and fluid shot out of my cock through the cage, I bucked wildly, she didn’t ease up putting more pressure against me. I was speaking in gibberish, a wave of pleasure hit me. She pulled her fist out still clenched, leaving with a loud pop. I collapsed on the floor, covered in sweat, cum, vomit, and lube.
“Leave this bitch here, these guys paid off your debt, don’t ever be late again!” She shouted, pulling her gloves off. Everyone had been masturbating, I was finally able to see around the room. They were getting up and leaving. They left me there naked, without my clothes, I laid exhausted. My mind was racing; what the hell just happened.