A Late Starter

Misgivings shot through me as I folded helplessly over the couch, Aron's hand effortlessly holding me in place. My own body weight worked against me in this position- basically he could keep me from shifting as was necessary to get up off the couch with his one hand. His other hand was on his well lubed cock, spiraling it against my slick, virgin ass. He wasn't shoving, but each rotation it went a little deeper, wallowing the outside of my asshole but not straining the tight ring of muscle that would be the cause of any pain I'd feel.

I started believing in his gentleness again, that flash of surrender I'd felt when I'd wanted to accept him wholly; allow him to take me for his own pleasure while easing me into this new experience in easy stages I could handle. His words were an echo to my thoughts. Never ceasing his massage of my tight hole, he leaned forward a bit (Not removing that controlling hand on my back, the still terrified part of my mind reported), and asked if I was still sure that I wanted to do this.

Against the couch's back my cock was harder than I could ever remember- the skin stretched so tight it hurt- and I was feeling things from my asshole I never had before. I heard my voice, shaky and a little scared, saying, "Yeah... just...take it easy at first, OK?". The pressure from his prick on my ass ring increased a bit- not enough to force itself in but enough so that my muscles were forced to tighten to keep the invader out. "Alright, I need you to try to relax for me then. This is going to hurt at first, and you might want me to stop. Will you give me 10 minutes, and if you want me to stop then, I will...?". I now know what he was saying, but at that moment I was just overcome with gratitude over his understanding. "Sure".

The tip of Aron's cock started pushing hard against my rear hole. One hand, no longer needed to guide his tool, came down to grip my hipbone while that unnerving other hand on my back kept me from standing up. With all the lubricant and my current position, I was no match for THIS assault, and that purple strawberry I'd so lovingly sucked started to stretch me open. I'm pretty sure the pain started when I was stretched just past 2 fingers worth- a hard and bright circle of agony that burned white hot. I couldn't take this- I was convinced no one could. I made some kind of noise and tried to get away... and of course I couldn't.

Agonizingly I was stretched wider, and I finally remembered how to make words. "STOP! YOU'RE KILLING ME!". Even as more and more of that damned ever widening head split me open, I heard Aron say "uh...You promised me 10 minutes...uh... are you welching?" I tried to catch my breath, to say fuck yes, You win, I can't take anymore, and the pain hit a new level as my screaming rectal ring snapped over the head of his cock. It wasn't much release, but the pain dropped a bit, allowing some part of my mind to remember my promise.

Aron stopped pushing once the head was lodged in, to give me adjustment time, and probably time for him to enjoy my twitching anus, milking him. Had my calves, holding me on tiptoe, not decided to give out right then, I don't know what would of happened. Give out they did, however, and I sank back a full 2 inches, which meant I took 2 inches of his manhood beyond the head right up my ass.

I was shocked to discover it didn't increase the pain too much, beyond a slight burning at my asshole from the friction. I started to feel a wonderful feeling of fullness, or completion, or something, just above the pain. I desperately tried to get more, but the damned position I was in- or blessed position as it forced me to get to this point- wouldn't let me. Aron, as usual, was ahead of me and started a slow yet unstoppable push that ceased only when his balls made him stop. The pain was still there, but now I was willing to take it for the fullness I felt, and I groaned something like "God yessss ".

He had me and he knew it, and started pulling that incredible cock out of me like a King pulling a sword from a stone, leaving me incomplete and empty. He stopped mercifully at the crown of the head, and sawed that slickened saber back in with an easy strong stroke that snapped my head back. It's a blur after that- the quickening pace, the mix of pain and pleasure. I'm sure it was Aron that changed the tableau, as I found myself on my back on the couch with my legs wrapped around his waist as he pounded out the end of our night. The pain never really stopped, but drifted into the background as he tattooed something in my ass, making my cock throb in time to his thrusts. I finally couldn't take it and reached down for my cock, and after two quick strokes exploded all over my stomach. My asshole cinched tight as I came, and it was too much for Aron. He went up on his arms and went stiff, and though I didn't think it possible, that miracle cock swelled larger inside me as he shot the load my mouth had looked forward to earlier up my aching but eager ass.... I didn't mind a bit.

I have this fantasy frequently, and will soon make it come true. Your comments and suggestions are certainly welcome.