Archive of Our Own ^beta

It was game night and my buddy Tim and I were hanging out, drinking beers, and playing some poker. Just two friends, enjoying a casual night in, though he had to keep an ear out for his 3 year old son, Danny. Tim's wife died a few years back, leaving him a single dad.

Tim and I were hanging out at his place for our usual weekly game night, drinking way too much beer and playing poker well into the early hours of the morning. As the empty bottles piled up, our inhibitions lowered and the stupid bets started flying.

"I bet you can't shotgun a beer in under 5 seconds," Tim slurred, sliding a fresh bottle across the table to me. I eagerly accepted the challenge and impressed him by crushing it in only 4.

The ridiculous dares and wagers continued to escalate from there. "Okay, okay, I've got a good one," I announced, swaying slightly in my chair. "If I win this next hand, you have to run outside and streak around the block totally naked."

Tim threw his head back, guffawing loudly. "You're on, dude! And if I win, you have to call your ex-girlfriend and confess that you still love her."

We both laughed hysterically and revealed our cards. Tim won that round, so I drunkenly dialed my ex's number and left a rambling, heartfelt voicemail.

By 3am, we were both completely hammered and our bets had reached peak stupidity. "Dude, I'll bet you a hundred bucks that I can fit my whole fist in my mouth," I declared, contorting my jaw in a drunken attempt to prove it.

Tim howled with laughter, doubling over as tears of mirth streamed down his face. "Alright, I raise you this, if I win this hand, you have to let me slap you straight across the face as hard as I possibly can. And no blocking or flinching allowed!"

I scoffed confidently, glancing down at my cards. "Fine by me. Then if I win, I get to fuck Danny."

Instantly, Tim froze, the color draining from his face as he stared at me in shock and appalled discomfort. "What the actual fuck, dude?! He's my son! I can't believe you'd even say something that twisted!"

I rolled my eyes, waving off his outraged reaction. "Relax man, I'm just messing with you. It's not gonna happen anyway. You're obviously going to win with that famous poker face of yours," I joked, trying to diffuse the sudden tension and awkwardness now hanging heavy in the air between us.

Tim still looked extremely uncomfortable but after a moment's hesitation, he reluctantly agreed to the outrageous terms. "Okay fine, it's a deal. But there's no way in hell you're gonna win, so it doesn't matter."

We revealed our hands. To my surprise, I had a flush while Tim only had a straight. "Well, looks like I won after all," I said, leaning back in my chair with a smug grin. "Guess I'll be collecting on that bet now."

Tim paled even further, looking queasy and on the verge of passing out. "You can't be serious, man. I was only joking around. Don't make me go through with this, I'm begging you. It's sick. He's fucking 3 years old, he still has to wear a diaper!"

I shrugged nonchalantly, polishing off the last of my beer. "A bet's a bet, dude. You agreed to the terms and I won fair and square. Don't worry though, I promise I'll take it easy on the kid and be gentle with him." I stood up from the table and started heading upstairs towards Danny's bedroom.

"Wait!" Tim called out, jogging after me with a panicked look. "If you're really gonna go through with this, then I'm coming with you." I raised an eyebrow, shooting him a curious look. "Oh really now? And why's that?" Tim blushed furiously, his drunken state wasn't helping, unable to meet my gaze. "He's my son, okay? The least I can do is be there to supervise and make sure you don't hurt him too badly."

"Alright, fine, I can live with that," I agreed with a shrug. "Though I have to admit, I am rather curious to see how you'll react to all of this."

"Deal," I said. "Though between you and me, I'm curious to see how you'll react too."

----

We entered Danny's darkened bedroom, lit only by a small nightlight, where the 3 year old was fast asleep on his toddler bed, snoring quietly with his thumb in his mouth. I approached the bed, gently easing the soft blanket off of him while Tim hovered anxiously at my side, wringing his hands.

After a moment's hesitation, Tim unzipped his jeans, pulling out his stiffening cock. "I still can't believe I'm letting this happen," he said, slowly stroking himself to full hardness. "This is so wrong on so many levels."

"But it feels so right," I purred, running a hand up Danny's pj-clad leg, caressing his soft baby skin. "You want me to do this, on some level. You wouldn't be getting hard otherwise."

I looked down at little Danny, fast asleep and drooling on the pillow, completely oblivious to what was about to transpire. Carefully, I eased off his cute dinosaur pajama pants and diaper, exposing his tiny, hairless cock and little balls. The cold air made him fidget and fuss a little in his sleep, his small hands seeking his missing blanket. Both Tim and I stood looking in awe at the sight of the naked toddler splayed out before us, ready and waiting.

"You have to prep him first, use lots of lube," Tim said, his voice thick with lust as he continued jerking himself. "I don't want him to have any permanent damage."

Nodding, I took Danny's legs in one hand and scooped them up, holding him by the ankles. I grabbed the baby lotion from the nightstand, squirted out a generous amount onto my fingers, and began gently massaging it into his tight little virgin hole. "There you go," I said softly. "Nice and slippery."

Taking my pinky, I slowly circled his pucker before easing it inside, carefully stretching him open. The moment I penetrated him, Danny's eyes fluttered open and he started to cry, though his wails weren't too loud, more like a sleepy, confused whimpering. "Hey buddy! Uncle Rob is just gonna check you real quick, don't worry, Daddy's here too," I soothed. Tim came forward and took his son's face in his hands, wiping away the tears. "Shhh, baby boy, you're okay, Daddy's right here," he whispered in a choked voice. "It'll all be over soon."

I squeezed out some more baby lotion and coated my rock hard length, making myself slick and glistening, fully ready to violate the little boy. Tim's eyes widened, transfixed by the sight of me poised and prepared to take his son's innocence.

"Last chance to back out," I teased, rubbing the lubed-up tip of my cock up and down Danny's smooth crack. "Because once I start, I'm not stopping until I bust a nut deep inside him."

Tim gulped, his eyes glassy and pinned to the lewd scene, still frantically beating his meat. "I...I won't stop you," he finally said, voice hoarse and strained. "Just try to make it good for him."

I smirked, giving Tim a salacious wink, and lined the engorged head of my cock up to Danny's tiny, wrinkled hole, glistening with lube. "Don't worry, I'll make sure he enjoys every inch of this," I promised. And with that, I gripped his hips and shoved into him with all my strength, cleaving straight through Danny's virgin ass in one savage, brutal thrust. 

The toddler instantly came awake with a bloodcurdling scream, his cherubic face turning bright red and scrunching up in pain and shock as he flailed his limbs and sobbed brokenly. Tim rushed over, his fully erect cock bobbing obscenely.

"Ssh, it's okay baby," Tim soothed, petting Danny's fine golden hair tenderly as he pried open his son's flailing hand and interlaced their fingers. "Just breathe through it...such a good boy for Daddy... I'm so proud of you, such a brave boy."

Watching Tim's rock hard cock bob and bounce in time with his stroking, I snapped my hips savagely, plunging my full length into Danny's molten hot, chokingly tight heat over and over. His screeching wails gradually tapered off into hiccuping whimpers and stuttering breaths, his small hands shaking and clutching spasmodically at the bedsheets.

Sweat beaded on my brow and ran down my back and chest in rivulets as I reached down to grip Danny's hips even tighter, my fingers digging in bruisingly deep as I plundered that sweet, tender ass with ruthless, jackhammer force. Gasps and grunts escaped me with every brutal thrust. "Fuck, he was made for cock," I hissed through clenched teeth. "It's like his ass is vacuum sealed around me."

Tim let out a deep, guttural groan, still petting Danny's hair soothingly and squeezing his hand comfortingly. "He's never looked more beautiful than he does now, stuffed to the brim and absolutely wrecked by your filthy meat," he said in a voice choked with sick, depraved lust. Even as he roughly stroked his weeping, oozing cock, Tim never let go of Danny's hand, refusing to break that comforting contact.

Danny's cries shifted into broken screams, crying for help, crying in confusion, what were they doing, why is his body hurting like it never did before. 

I obliged, railing into him, relishing his broken wails and the wet slapping of flesh on flesh. I took my best friends hand and laid it on his little sons little tummy. "Feel what your best friend is doing to your little son" Tim felt his sons tummy bulging at each thrust. Tim was whacking off furiously, face twisted in a rictus of pleasure and shame.

"Fuck, gonna...I'm close," I warned, a tingling building up in my balls. "Gonna fill that sweet ass up with my cum!" And with a last snap of my hips, I buried myself deep and came, pumping the little boy's hole full of my jizz.

Tim followed soon after, coating Danny's face with his daddy's cum.  

I eased my cock from Danny's abused hole, watching contentedly as my cum leaked out around his stretched bloodied rim. 

"You've been such a good boy" I cooed to Danny. Tim took his son's face in his hands and kissed his forehead, put a new diaper on him and tucked him in. 

"Good night baby boy, see you next time" I said while we exit the boys bedroom.