Flipped - Part 3

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Jake and Troy had been fun, I couldn't deny it. Two straight guys, both with their own reasons, and both agreeing to come to a stranger's hotel room and have some element of gay sex. My mission was undoubtedly going well, but something was still missing.

I'd spent time deciding on both of them. I'd researched them, like some type of weird, perverted scientist. I'd practically stalked them to ensure that they were exactly what I was looking for, and even though they both ended the way I wanted them to, there was something almost rehearsed about the whole thing. I needed something pure. I needed something real.

The strip was an easy target, but I wanted to find someone raw. What good was it to stand there and pick out the qualities that I liked best in someone? It was no different than pulling up Grindr and taking my pick from there. If I really wanted to test my theory, I'd have to change tactics, so that's exactly what I did.

I'd been to Oakland exactly zero times in my entire life. It was a place I'd heard about only through second hand accounts and occasionally on the news. I'd be foolish to go, yet I was certain that if there was anywhere in the world that would prove more of a challenge, it was there.

I'd heard about the gang crime, I knew it was a dangerous adventure, and I was ready and willing to take it. Was I stupid? Quite possibly, but I was eager, too, and so that's exactly where I went.

There would be no pruning this time. I wasn't going to pick out a guy for his attractiveness or his age. I wasn't going to pick the most handsome or the biggest guy, I was simply going to park my car and the first man to walk by it would get a proposition, and I'd either get my head blown off or I'd prove to myself that any guy can be flipped.

It was dark which added another element of worry to the entire thing. The street I'd parked on was covered on one side by a footpath and a wall, and on the other side by a long row of dilapidated looking houses in a complex.

In the distance I could hear raised voices; an argument perhaps, or maybe just the chorus of a normal night here. I wasn't judgemental by any means, but it was possible that I was more naïve than I would have liked to admit.

I did consider abandoning my plans when a group of four or five men sauntered down the middle of the street wearing mostly blue clothing and looking very intimidating indeed, though they turned around before reaching me, so I decided to stay a little longer.

There he was. A figure in the distance, strolling along the footpath toward me in the shadows. There was no way of telling who he was or anything about him, but I was determined to take my chances. The warm hue from the orange street lamp overhead broke through the trees and illuminated him long enough for me to tell that he'd been with the gang of men a few minutes prior. It would be foolish of me to pursue this, but then again, I was feeling pretty foolish.

"Hey, can I talk to you for a minute?" The words left my mouth before I had a chance to think about them, and instantly I regretted it.

The guy was young, early twenties maybe, but he became immediately defensive, which I guess I understood given the circumstances.

"Who the fuck are you?" He quizzed, and now that I could see him more clearly, I could tell that he was Hispanic.

His skin reminded me of caramel, only probably even darker again. He wore a white wife beater shirt, with another blue shirt wrapped around his waist. As much as I would have liked to believe that the bulge in his pants was his cock, I could see the grip of the handgun sticking from the waistband.

"Sorry" I half laughed, "I'm nobody important, I just wondered if I could ask you a question".

He peered into the darkness of the car but maintained his distance. I kept my eye on the gun, and hoped that it wouldn't come to that.

"What question?" He asked, and I guessed that it was a Mexican twang I heard from his accent.

"You've got a killer physique, man" I told him, and it wasn't actually a lie. He didn't have that 'I hit the gym six days a week' body, but he was pretty fit. "Do you mind me asking how often you workout?"

He cocked a brow and then his lip curled into a beaming grin. He rubbed it away with his hand and spat from the gap in his white teeth onto the pavement.

"You've got to be fuckin' with me, man" he smirked, "who the fuck are you?"

I had no doubt that this was going to be more difficult than Jake and Troy combined, but what I did have, was money.

"Honestly, bro" I pressed, "I'm just curious".

The young man looked around the street and then back into the car.

"Are you a homo?" He asked, and I wasn't sure how to answer it.

"Does it make a difference?"

He scoffed again and shook his head.

"I ain't fuckin' with that shit, man" he told me, "now I'ma suggest you get the fuck up outta' here".

"I'll give you one hundred dollars to answer my question" I said to him, and he glared at me again.

"I don't workout" he told me, keeping his eyes on me as he extended his hand. I handed him the note and he checked it before laughing. "Man, you're crazy".

"I've another hundred if you show me your abs" I pressed, waiting to slam my foot on the gas if he reached for anything other than his shirt.

"Damn, you are a homo" he said, and looked around the street again, "you know you could get fucked up around here with that gay shit?"

"I'm not trying to offend anyone" I told him, "I just appreciate a good looking guy when I see one".

"Hey, hey, I already told you man, I ain't down with that shit".

The two of us went silent until finally he held out his hand again. It was certainly possible that he was going to run off with the two hundred bucks, but something told me that he wouldn't, so I handed over the second note.

"Are you rich or something?" He asked, standing up and pulling his shirt up to reveal a heavily tattooed mid section with some slight abs forming. He held it there as I gazed.

"I do alright" I said, "how about you drop those pants a bit so I can get a better look".

The young man dropped only his shirt, and made a noise with his mouth.

"Get outta here, man" he said, and began walking away.

I was too close to let this go. I slammed the car into reverse and followed alongside him, doing my best to stay straight. Good one, huh?

"Are you worried?" I asked, and he waved his hand toward me.

"I ain't no fag" he said loudly, as though he wanted other people to hear, "and you're starting to get on my nerves, man".

"Two hundred then" I said, "to show me everything".

He stopped dead and slowly turned back to me.

"You'd give me two hundred bucks to show you my junk?" He asked in a tone that made me think he didn't believe me.

"I gave you two hundred already, didn't I?"

He considered it.

"I could just take your money" he said, lifting his shirt to show the gun again.

"You could, but then it's only a one time thing. What's your name?"

Once again, the young man wiped a smile off his face and shook his head in disbelief. He bit down on his bottom lip, and now I could really see how handsome he was under all the ink.

"Diego" he said, "and make it three hundred".

I nodded and Diego walked closer to the car than he'd been so far. His eyes scanned up and down the empty street, searching in the darkness for anybody who might see him do this terrible thing, and a moment later he lifted his shirt once more, pinned it with his chin, and yanked down the front of his shorts. I watched eagerly as he pulled the blue shirt out of the way, until finally my eyes landed on it.

It was bigger than I had expected given the somewhat small size of the owner. Just like the rest of him, it was dark, and hanging from a bush of curly black pubic hair. His balls were also hidden under a layer of the stuff, but they looked long and heavy. He let me enjoy it for a moment before holding out his hand.

I passed over the cash, but Diego didn't seem to be in a hurry anymore. He put his hands on the top of the open window and leaned slightly toward me.

"So you do this shit often?" He asked, looking around the car.

"No, not often".

"You know this place ain't no shit that a posh boy like you would be used to, right?"

"And why is that?"

"Well" he shrugged, "I'm just saying, you lucky you got me and not one of my boys, because you wouldn't be sitting here now if you asked them that shit".

"And you're different to them, are you?"

Diego clenched his jaw, and spat onto the sidewalk again.

"I just don't believe in shooting motherfuckers for no reason, so don't give me a reason, understand?"

"How much for you to let me suck your dick?" I asked frankly. I think we'd gotten past the niceties.

Diego didn't seem shocked. I guess we both knew where the conversation was going, and it was only a matter of time before it got there.

"More than you have in that wallet" he smirked.

"You'd be surprised what I can fit in my... Wallet" I smirked back.

"Damn, you guys are freaks" he sighed, shaking his head, "five hundred, and another two because I'ma need you to give me a ride home after".

"I pay you to give you a ride home?" I asked, somewhat entertained by him.

"Yeah" he shrugged, "consider it protection money".

"What am I being protected from?"

"That" he said, pointing back up the street where a much larger gang of men were now walking toward us.

Before I had a chance to say anything, Diego was already in the passenger seat. I glanced at him, and he glanced back.

"You should drive" he said, and I agreed.

The journey was relatively short and relatively silent, until finally I pulled into an old, empty parking lot. Diego seemed more paranoid than I did, which was funny because he was the one with a gun.

"Why are you doing this?" I asked him, more to create some dialogue in order to speed things up a bit.

The young man wouldn't look at me. He continued to stare out the window before eventually answering.

"I have bills" he shrugged, "same as everyone, and I have a daughter to feed".

"Do you have a job?"

He laughed, and glanced at me side eyed.

"You rich people are all the same, man" he scoffed, "would you hire me?"

"Maybe" I said honestly, "I'm paying you now, aren't I?"

He shook his head and slid back his seat. "Well I guess we better get to work then, huh, boss?"

There was something in his voice that sounded almost like anger, but that was a job for a different kind of professional. He shimmied out of his shorts, untied the blue shirt and lay back in the chair.

"I ain't got all night" he sighed, and I guess I didn't either.

I unclipped the seatbelt and leaned over. He had a faint musk to him, but nothing too powerful. He tensed slightly when I took his soft, warm cock into my hand and peeled back the foreskin.

"Not a lot of guys around here are uncut" I said, but Diego ignored me so I did the only reasonable thing I could do, and sucked it into my mouth.

There was something different about Diego compared to the other two. Jake had been reluctant, Troy had been eager to get some sort of revenge on his father, but both of them had appeared to be somewhat into the whole thing. Diego however, remained completely soft and was busy biting the nail on his thumb when I looked back up at him.

"What?" He asked, "you want me to moan or some shit?"

I pulled his wet cock from my mouth and shook my head.

"Nah" I told him, "but at least let me make this enjoyable for you".

He stared at me.

"Let me lick your asshole" I said simply, and his eyebrows crawled up his face until they nearly got lost under his black hair.

"Another five" he said.

He propped his feet up on the edge of the chair, then pulled his legs back with his hands. It was surprising to see him agree so quickly, but I wasn't complaining.

His ass was pretty hot, and the trail of hair broke off slightly as it reached his dark hole. Somewhat awkwardly, I pulled his cheeks apart until the darkness became pink and I stared at his opening.

His balls hung limply above, his cock still flaccid and wet with my saliva, and as soon as my tongue ran across his sensitive ring, he gasped.

"Ain't nobody ever licked my ass, man" he half laughed, "that's all kinds of fucked up!".

I did it again, slurping along his soft hole and sliding my tongue through his sphincter. He gasped once more, his fingers squeezing the flesh of his legs, but he made no effort to stop me, so I continued.

It was dripping wet now. The slight taste of salty asshole covered my tongue, but it was a taste that I'd always enjoyed. I plunged it deeper into his ring, making him groan as it clenched around my tongue.

I continued rimming the young man, sucking and eating his hole as he shivered and moaned. Perhaps a man sucking his cock wasn't going to make him cum, but a man sucking his ring was certainly doing the trick.

"Holy shit, man" he grunted, and when I looked up, his cock had grown to a considerable size.

I took it in my hand, squeezing his shaft as a bulb of clear fluid trailed down the underside. With the taste of his hole in my mouth, I took his cock once more and swallowed the rigid member.

"Oh yeah" he mumbled, his hips thrusting gently, "that's it baby, suck that big cock".

His eyes were closed, and it was easy to tell that he was imagining me as some hot chick. I wasn't particularly bothered by that, and now all that mattered was finishing him off.

I licked his cock head, swirling my tongue across the slit and tasting more pre-cum ooze out. My hand worked the base, twisting and pumping as I swallowed him again. Each stroke made his sharp breaths break away, and now I could see the sweat patches under his arms.

His hand grabbed the back of my head, holding me down as his hips shook.

"Oh fuck yeah" he whimpered shakily, fucking my mouth, "eat that shit, baby, swallow that nut!"

He cried out, and as he did, my mouth exploded with sperm. It came in huge waves, filling me entirely until it burst from my lips. I gulped it down, but the young man was like a fucking hose. He was gasping and moaning louder than I'd ever heard anyone do it before, and each one sent another flood of cum down my throat.

It lasted nearly a minute, and I was sure that I'd never seen anybody cum so much in my life. He lay back, his chest rising and falling rapidly as his drenched cock slipped from my mouth. I couldn't let any of it go to waste, and immediately began lapping up the spillages from his pubes and groin.

"Alright that's enough" he said breathlessly, but there was still some left.

"That's enough" he said again, but I couldn't stop myself.

"HEY, THAT'S ENOUGH!" He roared, and I knew his hand was on the gun.

I sat back and Diego pulled his pants up quickly.

"Bring me home" he said, still trying to catch his breath, and I decided that that was probably a good idea.