I'll Take the Chance

I'll Take the Chance by AcrossTheRubicon©

Orignally published 08/19/07

Author's Note:

In 2007, I accidentally looked up Literotica on my iPhone while I was at work. I didn't have a VPN at the time (I wasn't terribly internet savvy), and I freaked out -- thinking that it would be flagged and not only would I get fired, but I'd be outed as well. I immediately contacted Literotica, and requested that my account be deleted, knowing all my stories would be nuked as well.

It was rough, because I'd poured my heart out in these stories, not to mention the fact that I'd salted little bits and pieces of my life all throughout them. I wanted people to read them, but I figured they were backed up somewhere and at some point I'd return. Well. You can guess where this is going.

Years passed by, and those stories were lost to time. Until... I accidentally entered "Literotica" into the Wayback Machine, and with a little digging... I found all of them. I've glanced at them. They're cringey. They're also full of self-loathing as I was only at a nascent stage of accepting my sexuality. (Which I still haven't achieved after about 40 years of fighting it.) So, I'm going to republish these stories just so anyone who's curious to see how I've developed as an amateur smut author and a human. I'm not even going to reread these before publishing them, because it just amps my anxiety through the roof.

We all make our choices folks. Anyways, enjoy this trip down memory lane.

This one, is one of my favorites. Everything that happened up to the part where the narrator gets in the car is true. Lol. (I should've gotten in the car.)

-Jack_Beastly (formerly AcrossTheRubicon, MonkeyWrench00, SweetCamilleCD, and probably a couple others.), member since 2004 (at least), reader since 1998.

___

"How're you doing tonight?"

The question came from a Ving Rhames look-a-like driving a sleek, expensive silver-grey sportscar. I was walking home through a collection of bars in a relatively upscale part of the city. It was late, and I was tired.

"I'm fine. Thanks."

I wasn't really in the mood for conversation.

"Where're you going now?"

His car had slowed to my pace and it was softly growling beside me.

"I think the night's over for me."

There was a little pause.

"It doesn't have to be."

I kept walking for a step or two, ignoring him. He was taking a chance here. This wasn't necessarily a "Gay" part of town, and I looked pretty straight. I didn't have any effeminate affectations. I didn't dress preppy- which in this town was kind of the dominant style of the majority of homosexual men.

But.

It takes one to know one, right? I stopped and gave him a slow appraisal. He was a big, thickset guy. A bit of a paunch, but strong. He had an expensive looking wristwatch sitting on a large, vein corded forearm. His polo shirt was stretched across a massive chest. I knew that if things went bad with this guy- they'd go real bad, real fast. He stopped his car, fixed his eyes on me and smiled. The lock on the passenger side popped up.

I took a deep breath. "What the fuck," I thought, "I'll take the chance."

I had an instant image of his large hands gripping my firm white ass cheeks in his palms and my asshole started to tingle.

I slid into the car. The seats were a kind of glossy leather. As I inhaled that "new car smell" I thought about my own shitty Chevy. This thing was sparkling.

"Your place or mine?" he asked.

"Yours."

The engine made a deep thrum and he started off around the corner.

My heart started to beat hard and it was a little hard to breathe. In for a penny, in for a pound."

He got on the highway and we started heading out toward one of the outer suburbs. I started rubbing my cock through my jeans, just like a girl would rub her clit- in a slow circular motion. With my face I affected that dreamy, pre-orgasmic look of so many porn actresses. I started to rub a nipple with my free hand. I made a soft moan.

He looked out of the corner of his eye, "Damn..."

I could see his cock twitch in his slacks. I reached over and gave it a lingering squeeze. He had to be seven or eight inches hard, and he was thick.

The car made an almost imperceptible swerve and I took my hand away. His forehead was beaded with sweat.

"Thinking about what you're going to do to me Daddy?" He grunted and bit his lip.

"You goddamn bet I am."

"Are you going to put that big thing in my little asshole?"

He let out a little expulsion of hot breath.

"Boy. You're going to make me crash this car."

Soon we were at his house. He lived in a gated community. The houses were large, and separated by large expanses of lawn and forest. Lots of privacy, and virtually every car in evidence was just as expensive as his.

He turned into a long winding driveway that curled behind a mini-mansion. I was tempted to ask what he did for a living, but I really didn't care. He pulled around to a garage in the rear of the house and parked.

"Let me get out first." I said.

I walked around to his side, opened his door for him and took a step back. I looked around. Nothing but trees. You couldn't even see anyone else's houselights.

As he stepped out of the car, I sank to my knees on the asphalt.

I put both hands on one of his massive thighs and started to nuzzle my face into his crotch. I unzipped his slacks and stuck my nose in the fly. I inhaled his man-scent and started to kiss his pubes. His cock was starting to harden again, so I pulled it out, with some effort. It was perfect. Not too big. Just nice and long, and thick- but not terrifyingly so. I started to squeeze it in my hand and I put my lips on the head, giving him nice circular round licks. I slowly dragged my tongue over his piss slit, leaving it there for a moment. I took one hand up to his massive, beautiful balls and slightly massaged one of them.

"Ok. That's enough. In you go." I stood up and we went inside, his dick still throbbing out in the open through his fly.

He marched me quickly upstairs and into his bedroom. Once we got there we both started quickly taking off our clothes. He tore off the comforter and the top sheet and gave me a light shove onto the bed. He stood there looking at me for a second. The cotton was so soft, I started to wriggle around a little, then I spread my legs and gave him a sultry look. I put my middle finger all the way in my mouth and slowly sucked it out, placing the wet digit against my cockhead, twirling it around like a girl again.

His chest heaved. "Shit."

Guys love it when you act like a chick.

But I didn't want to start this thing on my back. I got up and before he could say anything I took his massive dick in my hands and my mouth. I started with those slow circuits of my tongue around his head, then I took as much as I could into my mouth. I bobbed up and down a little, then I loosened my jaw and went for the whole thing.

I didn't make it. I choked and gagged a little, and I hoped he was getting turned on by the saliva that I was coughing out around his cock and through my stretched out mouth. I took a deep breath again and went for it again. This time was more successful, but I wasn't nose to pubes yet.

I pulled my mouth off and gagged a little more. I needed to breath for a minute. My eyes were tearing up too. I rubbed his wet dick all over my face, catching it on my lips and I started stroking him.

One more time... I took it back into my mouth and made it this time. It felt like it was entirely down my throat.

"Fuck this. I need to fuck you."

He pulled out and I whimpered...

I stood up and he turned me around shoving me half over the bed.

From his nightstand he pulled out a bottle of lube which he quickly proceeded to pump into his palm. He started to slather it around my ass. First came one finger. Then another at the same time. It was painful. I'll tell you that. I felt myself tear a little. He started massaging me in there a little bit, then pulled out, added more lube and went back in. I spread my legs wide and pulled my cheeks apart. His fingering became faster and faster until he abruptly stopped.

"Are you ready for my cock, Boy?"

"Yessir."

I could hear a condom wrapper tearing. I could hear him slick his cock up with lube. I could feel the lube inside me seep out of my asshole and down my inner thigh.

Then. It was there.

His head felt enormous and I was wishing I had some poppers, or something.

I felt it push hard against my ring and then he gave up for a second. I pulled my cheeks apart again and it returned. He was circling it around my hole. It felt like a lemon. He stopped and started pushing it in. He was more determined this time. I let out a little cry as he entered me.

"Damn, you're fucking tight."

He was still slowly pushing in. I could feel some of his shaft now, and it felt like he was churning up my guts. And yet, he kept pushing and it kept coming. I was grunting and biting the sheets. And then, when it felt like I had a telephone pole up my ass he stopped. I could feel his big, pendulous nuts against mine.

"You feel ok?"

"Swell." I said, choking out the word.

"Good." He didn't care. He started to saw his big bone in and out with increasing speed. Occasionally he slapped my ass, gripping it and twisting. I was in heaven.

I loved being underneath such a huge and powerful man. I wish there'd been a mirror so I could see his dark brown skin contrast with mine.

But make no mistake, this was painful. I wasn't sure I was having a good time, or not. I let out a little laugh and he slapped my ass again.

Soon, I could tell he was going for broke. I had sufficiently loosened up and he was pounding in and out of me. It felt like hours, but suddenly it was over. He tightened his grip on my butt and I could feel his cock buck inside me. He roared as he came.

After he was done, that was it. He explained that he didn't suck dick or take it up the ass. That's what I figured anyways. While I was taking a quick shower, he called a car service to his house to pick me up. Before I left, he gave me his number.

"Call anytime."

I knew I would.

Comment by Crazy87875, posted on 01/07/12:

OH MY FUCKIN GOD!!!! I would give absolutely anything if that was my ass gettin fucked by that big black cock!!! Pain is pleasure!!"