I don't like my chances

[Bareslut-66]

I like the start of this story, very promising 

[flakker]

"Wanna see something else" he asked as I gently stroked this monster cock. I'd never felt anything like it, so hard yet soft in my hand. I glanced up.

"Uh, like what?" I asked.

"C'mon, I'll show you. You'll love it I'm sure." he said. He turned away and my hand fell away from his cock. I stood up and followed him like a lost puppy. He opened another door and waved me in to what seemed like a spare room. Inside was a padded bench facing a rack of various toys. The bench was made of dark wood with leather pads where you could rest your arms and legs.

"Cool isn't it? And it's actually pretty comfy. Wanna try it?" He asked me. His grin was positively predatory now.

"Yeah, it's pretty cool, but I dunno, I'm not..."

"Tell you what, flip a coin. You lose, you lie down on it for me and tell me how it is" he suggested. Something about this whole chance going was turning me on. I shrugged and he flipped the coin. I called heads.

"Tails. So hop on, boy" he said. I could feel my heart racing as I lay down on the fuck bench.

"So this is a whole day of firsts isn't it, boy. Let's flip for the cuffs and gag. Get the whole experience." I heard him flip the coin and catch it before I could object. This was getting out of hand.

"I...uh.... Heads?" I said instead of arguing.

"Ooh, tails it is." He put the chin down without even showing it to me. For some reason I just meekly opened my mouth as he jammed a rubber gag in. I felt the click of cold steel round my wrists. He rested his hand on my head. I could feel his cock resting between my arse cheeks through my shorts.

" So let's flip for clothes, eh?" he flipped the coin. Wait, what? How was this meant to work? I couldn't talk round this gag forcing my jaw open. I tried to argue.

"Man, you sure can pick em. Nope, tails you lose, let's lose the shorts." I could feel the cold steel against my arse this time as he cut my shorts off with some shears. I started to cry a little as my situation sunk in. What the fuck had I got myself into?

He gently ran his hands down my back as I felt the head of his cock start to rub between my cheeks. I could feel the slick precum start to leak onto my tight arsehole.

 

[pozpopperpig]

Love this dirty game he is playing like a carnival barker.  This boy doesn't stand a chance....HOT!

[austin_submale]

Nice so far!!!

 

[kitpig]

I wish I had a neighbour like that!!

[flakker]

His cock head felt hot as it slipped between my sweaty arse cheeks. It was so hot in this room that my crack was already slippery with sweat, and it got slicker as his precum mixed with my sweat. I closed my eyes and my heart was pounding like a drum in my chest. I was so incredibly turned on but also terrified about the massive poz cock poised at my hole.

"My my, you do like to live...dangerously don't you? I wonder what the odds of you converting in one fuck would be?" he spoke as he slowly  rubbed his cock between my cheeks. His cockhead brushed my tight virgin hole and I flinched, but at the same time a jolt ran up my spine, I was so turned on.

"How dangerously, I wonder? Hmmm......maybe you'd like to flip for lube? Or condoms?"

Wait, what? Was that one flip? Or two? I couldn't quite figure out what he meant, I tried to nod and shake my head while asking in muffled moans round the gag for him to please use a condom. I heard the flick and slap of him flipping another coin behind my back again.

"Ooh, bad choice I'm afraid. No condoms or lube it is. I do hope your not the type to welch on a bet." John lined his massive cock up with my virgin hole. I'd never inserted anything bigger than a curious finger up there and now there was a bare poz cock beginning to press against it. It was somewhat slippery from the sweat and precum that had slicked my crack, but not enough for this! I clenched my jaw and bit hard into the rubber ball gag as my hole burned and stung, straining to accommodate the invading cockhead. The pain abated very slightly as the head popped in and John eased back from pushing in.

"Oh, that is a lovely, tight arsehole you've got there. Can't believe your so happy to just risk that lovely neg hole getting ruined on a silly bet." He slowly started to slip the first little part of his cock in and out of my poor hole. The burning increased again, but I could feel it starting to become a bit slicker. How much precum was that poz cock leaking into my unprotected arse? And why was my cock so hard, even through the pain radiating from my arse.

"Whoops, think I might have torn you up a little getting in there. Little bit of bloods nothing to worry about though." John chuckled as he worked more of his cock into my hole. I continued to bite the gag and tried to breathe as my hole was slowly stretched and I began to feel the red hot length of his cock slide slowly further and further into my rectum. After some minutes, as John thrusted in I felt his balls slap my arse as he finally bottomed out. My arse was on fire and it felt like his cock was trying to take up some serious space in my abdomen. As he fully penetrated me, he leaned forward and rested his hands on the small of my back, pushing me down. I felt a drip of sweat fall from him and hit me between the shoulder blades.

"Well, don't you fit like the perfect cock sleeve! With a little persuasion. Now, how about a real bet?" I tried to catch my breath. I shuddered and writhed slightly on the iron bar piercing me. What the fuck else? What did this guy have in mind for me!

 

[RotzBBengel]

Fuckin love it! This is getting better and better and better...🔥🔥🔥

[Bayareabbcub]

I can’t wait to read on! This is so good! 

[Mvillebottom]

Very hot writing and the coin toss is a awesome idea that would be fun to do

[sfvalley79]

You just know that the top has a trick coin with tails on both sides... Can't leave it to luck if there's a sweet hole to use...