The Bear and the Jock

"Look at that tight little boy pussy. Fuck, I can't wait to slam my cock in there. But first I gotta get you ready for me," Bear murmured to himself, his voice full of desire and need.

And I was filled with terror as I watched his dilated eyes staring at my tight asshole with a ravenous hunger burning from deep within.

He gripped my thigh with his left hand and his hand was so big it nearly covered my whole thigh making me feel even smaller. I had always been a confident - some might say cocky - guy. I had always felt like a man; strong, untouchable, and now I was reduced to this pathetic little boy crying and pleading, snotting on myself as if I was a kid again. Any other time this degradation would make me furious, but the feeling of fear and vulnerability overpowered any other feeling within me. Bear had total control of me, he could and would do anything to my body and I would be helpless, I was helpless.

I no longer felt like a man, I didn't think I ever would again. All of that, including my life, was in Bear's hands.

I lifted my head and looked down my body in horror as Bear's thick shiny fingers brushed my puckered asshole making me whimper. I looked up into his dark eyes as he massaged my taint and hole, and I gulped in fear. "Please, please Bear please." All I could do was beg and pray he would feel bad and let me go but his response dashed my hopes completely.

He looked into my wide eyes as I pleaded and he circled my tight asshole before growling deeply, "Christ boy, you keep pleading with me like that you're gonna get fucked sooner. I didn't expect you crying and begging to be such a turn on, guess I'm more depraved than you or I thought." He smiled cruelly before pushing his thick fingers into my tight opening.

"Fuck, stop man. Fuck it hurts!" I cried and tried to squeeze my hole to keep him out.

"Easy there, relax baby, it won't hurt so much. Gotta let Daddy into your little boy pussy," Bear cooed as he pushed his fingers deeper inside me making more tears pour from my eyes as I shook my head in denial that this was happening.

Please make this be a nightmare that I'll soon wake up from.

It burned as he stretched my asshole around his thick fingers making me sob and sniffle in shock and despair. "Stop, oh God please stop Bear, your hurting me."

"That's what you get for mouthing off across town about me." Bear glared into my wide pain filled eyes as he repeatedly pulled his fingers out and then pushed them in deeper than the last stroke. "You should thank me boy, I could have just slammed my big cock into your dry virgin ass. It would've ripped you open. But no, look how gentle I'm being with you, I want you to enjoy it. That'll be your punishment; the shame of knowing I had you begging me to make you come while my cock pounded your ass."

He continued to ready me for his cock, which I noticed had grown even bigger and the head was red and leaking pre-cum profusely, it would also twitch and jerk in anticipation of penetrating me. The pain lessened and the glide of Bear's digits became faster, smoother, before he removed them completely making me relax, but then he poured lube onto his monster cock making it jerk excitedly before squeezing more onto my now opened asshole.

My heart began to gallop as he stroked the lube up and down his thick shaft, the bulbous head now turning purple showing his desperate need to explode a flood of his cum deep inside me.

"Fuck boy, I ain't gonna last long. You've gone and gotten me all riled up." Bear chuckled and shifted forward on his spread knees, his cock now bobbing right in front of my hole and I watched as a string of pre-cum dripped from his engorged head to land on the crack of my ass. I immediately began to struggle against my bonds, causing the ropes to bite into my skin and tighten painfully.

"No, no, no, no, please no! I don't want it, please don't put it in my ass, Bear please!" I cried and struggled, and my whole body flinched when the tip of Bear's shiny cock brushed against my ass cheek. "Help! Please someone help me! Oh god no, please no. This can't be happening, this can't be happening!"

"Oh it's happening alright. My cock is gonna fuck the shit outta your tight little virgin ass." Bear chuckled deeply.

"Please Bear, I'll suck you off instead. Please just don't put it in my ass, please. I'll suck your cock better than anyone ever has before, I swear!" I cried, completely telling the truth, I'd much rather choke down that cock than take it up the ass, I'd gladly do so enthusiastically.

"You're gonna suck my cock later anyway, little boy. You think I'm gonna fuck your ass and that'll be it?" Bear laughed as he circled the leaking tip around the rim of my hole. "I told ya boy, by the end of the night I'm gonna have you begging me to fuck you again and again. I'll have you on your knees worshipping my cock by eagerly swallowing all my cum into your belly."

Then to my horror he pushed the engorged tip into my asshole, stretching me painfully and I squealed like a pig as my eyes widened in shock. He gripped the back of my thighs roughly, and when the whole engorged tip was inside me he pushed in a bit more before pulling back a little and then pushing in a little deeper, and I watched Bears face slacken in pleasure as he gazed at his cock slowly penetrating me.

"Fuck, you're so goddamn tight baby," he groaned deeply, and his eyes trailed up my toned body admiringly.

He was so big, the pain was unbelievable, I felt like I was being ripped in two. I shook my head and pulled at my bonds desperately. Snot and tears covered my face as I sobbed in pain, terror and shame.

"Oh god, please Bear stop. It hurts, please!" I pleaded, my eyes imploring him to have mercy but it only seemed to make him harder. He continued to repeatedly pull from and push into me, loosening my tight ass a little, while I continued to uselessly struggle and cry.

"That's it, take Daddy's big cock like a good little boy," Bear growled as his hips began to pump faster, deeper, his huge balls repeatedly smacking my ass crack. He eventually bottomed out inside me, his hips snug with mine. I felt too full, like I would burst from the pressure of his pulsing cock fucking me.

He shifted angles by planting his hands on the bed either side of me and leaning forward. He was hovering over me now, his hair falling forward and his broad shoulders a canopy of tattooed muscle above me.

"Please Bear," I sobbed, but he just looked down at me with pleasure filled eyes as he rode my ass deeply. I sniffled and had to catch my breath before speaking again. "Your too deep, too big. It hurts," I sobbed and watched Bear's nostrils flare as he stared down at my messy pleading face.

"I need it boy," he gasped and his eyelids fluttered as I squeezed my ass around his pumping cock. "Daddy needs to be in your little pussy. You feel amazing wrapped so tightly around me. Best ass I've ever fucked and I only just got started," he gasped.

Something about how he looked at me, praised me, like he couldn't get enough of me made my dick twitch. The pain wasn't so bad anymore, I thought I was going numb, but then the glide of his cock along my channel began to feel nice. I felt dread fill me then, fear that he would make my cock hard, hard enough to cum like he predicted.

"You motherfucker," I grunted through my sobbing.

His pace quickened, his big cock repeatedly jabbing up into me, his hips pistoning. "Fuck boy, I'm gonna come deep in you," he growled and then he wrapped a big hand around my throat, cutting off my air, his eyes boring into mine, dominating me as he began furiously pounding that monster cock deep making my whole body jerk. The sound his balls made slapping against my ass was lewd and made me feel even more humiliated as I choked.

"Fuck, fuck, fuck, take it boy, take your Daddy's big cock!"

I watched with bulging eyes as Bear pounded my ass before his thrusting became jerky and I knew the signs of a man about to come and come hard. His face turned almost feral as his hips slammed into me, teeth bared, nostrils flared as this beast of a man roared his pleasure and I could feel him empty his huge cum sac deep in my bowels with each powerful slam of his hips against mine, bruising me.

He released my throat causing me to gasp in a breath as he slumped above me, his chest heaving, cock still pulsing and leaking inside me.

"Jesus Christ boy, I ain't cum that hard in years," he gasped, his eyes opening to stare down at me. One big arm was holding him up off me, while the other which had been tight around my throat palmed the side of my face, his thumb brushing across my parted lips tenderly.

"You're a good boy," he whispered before gripping my jaw and lowering his face to mine.

My eyes widened just before his lips crashed against mine, and then his tongue was licking me, but he didn't dare let go of my jaw in caution of me biting him, which I would have.

I groaned in disgust and struggled uselessly which only made him chuckle before he pulled away from me to sit back on his heels, his cock slipping from my abused asshole.

He watched it leak a load of his cum, and I could feel it trickle down my crack. This man had just taken me, had claimed me his bitch, making me fill with embarrassment and shame, at least he hadn't made me cum, I felt I had some dignity left because of that.

"Your dicks half hard boy, guess you were beginning to enjoy me fucking you." Bear laughed and slapped my ass cheek making me redden in shame and my cock soften once again.

Bear stood from the bed and began rooting around in the night stand next to the bed making me wonder what he had in store for me next. Surely he would leave my ass alone, it was throbbing in pain from his rough pounding. He extracted some kind of sex toy from the drawer, it had a small silver handle where a black rubber looking thing curved out from. It looked like a small dildo that curved up at the end. Bear pressed a button on the handle and the rubber end began vibrating, he watched me as my eyes widened when he upped the vibration before lowering it and turning it off.

"What the hell is that?" I breathed.

"It's a prostate massager, it hits your g-spot and makes you orgasm without even touching your cock." Bear smiled at seeing my wide wary eyes.

"Please don't put that thing inside me man, my ass is killing me," I begged him but he just smirked at me before climbing back on the bed into the spot he had left.

"This little device is gonna make you see stars boy," he chuckled as he poured a bit of lube on the end, although I could still feel some of Bears cum in my ass. He slid the toy into me, making me wince at the burning pain it caused me to feel.

"Please Bear don't, I can't take anym- oh god fuck!" I shouted when he switched on the vibration and angled the curved end about two inches inside my ass, pushing it against something that sent a shiver of pleasure dancing across my skin. I looked down my sweaty, sticky body and watched my dick grow and harden. When Bear upped the vibration my eyes shot to his and widened while my jaw dropped from the amazing feeling it caused to sing along my nerves.

"Oh fuck, no, I don't wanna cum, please don't make me cum!" I exclaimed, pre-cum trickling from my now heavy cock.

Bear just chuckled and upped the vibration again and my eyes literally rolled into the back of my head and I moaned in ecstasy as my leg twitched. I was going to cum any second and it was going to feel amazing. Part of me wanted nothing more while another part didn't want to give Bear the satisfaction. My toes curled and my hips rolled while I moaned like a bitch in heat. I was about to tip over into pure bliss when suddenly the device was removed and a hand had a tight painful grip on my balls, instantly pulling me back from the edge.

"Whaa? Oh God. What are you doing?" I sobbed in disappointment and relief.

"You ain't cumin' until I hear you begging me for it," Bear replied making me sigh.

"That's not happening," I gasped confidently.

"Is that so? I guess we'll see, but I'm guessing a few more times of me bringing you to the edge before pulling you back is gonna change your song right quick boy," Bear chuckled and pushed the device back inside me and turned it on low vibration.

"Oh God," I moaned as he upped the vibration, quickly bringing me back to the edge.

"Gotta beg for it boy. Say 'please Daddy let me cum."

"No!" Again, I was just about to experience a bone deep full body orgasm when he pulled the device from my ass and painfully gripped my balls, ruining my pleasure.

I groaned in frustration while Bear chuckled deeply. "I got all night long to do this, you ain't cumin' until you beg your Daddy for it."

He brought me back to the edge again, my hips jerking, cock leaking before tightly squeezing my ball sac and ruining everything. He did this again and again and again. I eventually lost count, he had turned me into a sobbing mess. My whole body was a wound up needy twitching jumble of firing nerves. My cock was throbbing painfully against my stomach, completely untouched and weeping. My balls felt so tight against my body, they desperately needed a release. My limbs jerked, twitched and shivered while I sobbed in frustration.

"Your holding out longer than I expected, but it won't be much longer now. Your practically drooling for it boy, you're a mess. Fuck, but it's hot," Bear growled.

I looked down to see his cock once again purple and leaking, and I knew this orgasm denial he was inflicting upon me was frustrating for him too. He inserted the vibrator again and I sobbed and shook my head because all I wanted was to cum, it was all I could think of. I knew I was about to crack but by this point I could hardly remember why I was holding back in the first place.

"Come on, beg me for it like the dirty needy little boy you are, beg Daddy to let you cum and he will. He'll make you come so hard baby," Bear encouraged as bliss sang across my jerking body.

"Oh God, please I..." My hips rolled, wanting it harder, deeper inside me. I needed that blissful release more than anything I've ever needed in my life.

"Yes, say it. Say 'please Daddy let me cum'." He instructed me eagerly.

"Fuck! Please Daddy, please let me cum!" I cried causing Bear's face to glow with triumph but I didn't care, I just desperately wanted to cum, but then he removed the device and I sobbed in absolute frustration, tears pouring from my eyes into my hair.

"Agghhh! Fuck! You promised, please Bear, please let me cum! I can't take it anymore, I fucking need it!" My hips still rolled in search of stimulation and I didn't care how much of a horny needy mess I looked.

"Told ye boy, ye ain't cummin' unless my cock's buried deep in ya." Bear suddenly slammed his dripping pulsing cock into me in one stroke, making me squeal in pain and shock before he took my slim waist in his grip and began furiously pounding his cock deep inside me.

"Look at me boy!" Bear growled, his balls slapping wetly against my ass crack. The feeling of his monster cock penetrating me was different this time, the pain disappeared and was replaced by pleasure and I moaned like a chick getting her pussy pounded good.

"Your little pussy is takin' Daddy's cock so well, lettin' me go so deep in you boy." He pounded the shit out of my ass, staring down at me with glazed over eyes and a slack jaw. That this grisly ex-con was undone by my ass sent a powerful feeling to bloom within me.

"Say 'fuck me harder Daddy'." His sweat dripped from his hair onto my parted lips.

"Fuck me harder Daddy, make me cum," I moaned wantonly, staring up at him in near awe that he was able to make me feel like this, make me say these dirty things.

Suddenly Bear planted his forearms on either side of my head and began roughly kissing me, his beard scratching at my skin, and then I was groaning and kissing him back, completely lost in the pleasure filled moment. He stuck his tongue into my mouth and I moaned and sucked it as if it was his cock.

"Tell me how good my cock feels pounding your little boy pussy," he groaned against my lips making my cock jerk against his stomach.

"Feels so good Daddy, don't stop, please fuck my little boy pussy harder," I begged as I stared up into his intense eyes, and it drove him wild and I realized I had power over this huge man. "Oh God, I'm gonna cum so hard on your big cock!" I cried as he continued to pound my ass, his cock swelling inside me.

"Fuck yes baby, you're so good, so hot and tight. I'm gonna cum deep in your belly, this ass is mine now, ye hear? Tell me whose ass it is!"

"It's yours Bear, cum in me again, please!" And I knew if I had my arms and legs free they would be wrapped tight around his sweaty body, holding him close to me.

Bear sat up grabbed my hips and slammed into me roughly, he roared his release to the ceiling and with each powerful pound of his hips he spurted a load of cum deep in my belly. My back arched and finally I was cumming, I screamed as my cock exploded a flood of cum across my stomach and chest, some even hit my face. Pure bliss raced across my jerking body, curling my toes and rolling my eyes into the back of my head, I almost blacked out from the pleasure as I shook and gasped for the longest time. It was unlike anything I had ever experienced before and I knew this feeling could get addictive.

I could still feel Bear's cock pulsing inside me as I slumped back onto the bed, my body limp and spent. Although my cock still leaked, sending jolts of pleasure racing across my skin making me twitch. I felt Bear hovering over me and I opened my heavy lids to see him panting and staring at me with deeply satisfied eyes.

"Good boy," he murmured before kissing me tenderly. He parted my lips and caressed his tongue with mine as his soft cock slipped from inside me, followed by a rush of his cum making me groan deeply. "That feel good? Hmm?" He hummed into my mouth before kissing down my neck and chest, his beard tickling my sensitive sweaty skin as he lapped up my cum hungrily. "Look at all this cum baby, Daddy made you cum hard huh?" Bear licked into my belly button before taking the tip of my cock into his mouth and cleaning it of all my cum making me twitch and moan.

"You've been such a good boy for me Jason. If I let you go will you keep being a good boy?" Bear asked as he sat up and began untying the rope around my ankle. I could only nod my head yes; my body was still floating in a languid relief.

As Bear removed the ropes from my legs and arms before massaging my aching muscles with his calloused hands, all I could do was lay there and let him. Part of me still fought his handling of me as if I was a little boy needing looking after, while another just needed to be soothed after that traumatic and shamefully enlightening experience.

I found I didn't want to be alone with my thoughts, so I stayed in Bears bed as he tucked me under his blankets before curling up behind my back, spooning me as if I was some chick needing cuddles after a good fuck.

Again, I felt a base part of me rail against the assumption I was the 'little spoon' but then I had just been fucked in the ass by a man I had been pushed into calling 'Daddy'.

"Sleep Jason, you done well. Now I'll look after you, you'll never have to worry about anything ever again. You're mine now."

At hearing those words whispered hotly into my ear, a shiver of anticipation and terror swept over my sensitive skin.

I was Bear's bitch now, and even if I fought against it, there was nothing I could do to change that fact.

But then again, did I really want to?

~

Anyone interested in a chapter 2?