This experience starts with a guy named Greg.
If you knew him well enough to give him shit, he was "Gorilla Greg" or "Gorilla" or "Kong". This is mostly because he was over 6.5 feet tall and one of the hairiest people you would ever see.
But it was also, for those of us "in the know" because he was hung like a gorilla.
For those of you thinking this means he had a big cock, let me dispel that. See, for their sheer size and weight, gorillas aren't hung. Pound for pound, humans are the primates with the biggest dicks.
I'd seen Greg's cock. I'd sucked it. One drunken night I tried fucking it.
***Note: I am not disparaging guys who aren't hung like Gods or even average. Truth be told I have enjoyed myself around guys with average and smaller much more frequently than porn cock guys. I'm only bringing it up because of his uniqueness, which will become apparent***
Greg had just a hair over 3.5". On the surface, not an issue. I've had tremendous fun with guys with less in the equipment area. The problem wasn't the barely three and a half. It was the 2.75" across. Not around, across. Around he was just over 8.
The night we'd tried to fuck was etched into my mind. I'd sucked him a half dozen times before then. I'd marveled at how he could fill your mouth without gagging you, because he wasn't far enough for the reflex. His bigger than average loads would fill whatever extra room you had in your mouth or drip out in an unreal hot visual.
Early one evening, quite a few years ago, we'd been drinking at the bookstore we hung out at (real books, not porn shop) and one of the other guys, Alexander, had pulled me off to the side and proceeded to tear me a new one. Just over 5", Alex had a prick that looked punished, gnarled. His circumcision hadn't gone as planned, leaving him with some significant scar tissue and an extreme downward aim.
If he took you from behind he would light your prostate up like a firework.
He was done after ten minutes. Four of those we were being watched by Greg.
When he'd finished blowing his load inside me, Greg asked if he could try.
He was already hard. I had small packets of lube I kept around. I figured Alex had just banged me, we could do this.
Doggie style my bit of a bubble butt and his bit of a gut stopped things from happening just as soon as he hit my rectum. I tried laying on my back on a table with my legs pulled up. He could just start pushing in.
We had an audience of about three, including Alex when we found the one position that somewhat worked.
I lay down on my right side. I pulled my left leg clear up to my chest. He straddled my right leg on his knees and pushed in towards me.
At first, he felt like he was going to tear me. I'd played with dildos close to his size so I knew there was a chance.
Then the thing happened. We were both mostly drunk so coordination was not in the recipe. He felt like he needed to readjust himself closer to me. He took a half-shuffle on his knees towards me, still holding himself at my sphincter.
He lost his balance. I felt like someone punched me in the asshole. Angrily. I bellowed,"JESUS FUCK CHRIST!!" as I clearly felt his entire head past my ring. Maybe more.
Sylvia, standing closest to us with a drink in hand said, "welp, that's as in as it's gonna get." She chuckled.
As for me, for the next four minutes I practically hyperventilated, gritted my teeth, bore down as much as I possibly could as Greg pushed his enormous cock head in and out of me. Sometimes a little more, sometimes barely the glans.
It never got easier. I'd need way, way more practice.
Finally his already ragged breath got choppy. He coughed once and pulled completely out only to jam back inside as far as he'd been yet. "Oh (breath) fuck me (breath) gonna c.. (breath)..cum!"
Problem was, again, coordination. The second he started ejaculating he twitched and the entirety of him came loose, spitting his regularly enormous load over my ass, perineum and balls, only to shove it back in to finish a few more pulses.
"Yay." Sophie said humorlessly, "gorilla fucks man. Makes huge mess. I ain't cleaning it up." She "toodled" us with her fingers and walked away.
Greg pulled away and the ache started almost immediately. I hadn't been ready. You had to be absolutely ready.
"I gotta get back to the house." He said, pulling on his pants, "the dogs are probably pissed."
I was still lying there, huge gobs of semen all over my groin and taint, more dripping out of my loose rectum, "dude! A towel maybe?"
He looked at the store owner, Thomas, the only one of us that didn't screw around with the others, "can you give him a hand?" Turned and walked away.
Thomas, in his normal sarcastic manner, began a slow clap. "When you get up, try not to get it all over, ok?"
I wrapped my hoodie around my ass like a diaper.
And that was the one and only time Greg got into my ass. I haven't had anything near his girth in over ten years.
***I wrote that entire bit to write this***
Four years ago was an entertaining period. My wife had several fuckbuddies of different gender persuasions. I had about five regular buddies myself, including two married couples.
My wife and I had moved down to Atlanta five years prior. We'd just moved into the house we built. Things were going well.
So when I got the call from back in Milwaukee, I was curious. I answered with the ancient method, "uhhh... This is Joe?"
"Hey fucker! It's Greg! How the fuck are ya?" His voice was chipper as always.
We talked for the next thirty minutes. Life, times all that shit. Right at the end he got to the point. "So dude, Anthony and I are coming down to Atlanta this coming weekend. Wanna hook up?"
I laughed, "hook up or 'hook up' here dude?"
He laughed back, "could be both, you never know."
"Yeah, the last time we didn't know I sprained my asshole." My voice was still sarcastic.
He fired back,"bullshit! You sucked me off like...a dozen more times after that night!" He wasn't wrong.