Hustling a Hustler

Hustling a Hustler

By Stephen Scott

Note: If you enjoyed this story, please contact me at Joe_Gillis_2000@yahoo.com

And a no-prize if you recognize the name.

I had just left the bar, bored and horny, when the boy spoke, asking me if I could light his cigarette.

I had never paid for sex before, but when I looked up and saw the kid, I knew I was about to.

He was small, slender, blond, with a cute young face and a humpy little bod. I doubted he was much older than 18. He didn't have that hardened look they get when they've been on the street a while.

I produced my lighter and struck the flint. He took my hand in his and brought it to his unlit Winston. As he pulled in the flame he looked up; his long lashes framed his blue eyes as they bored into my own. After the butt started burning he held onto my hand a fraction longer than he needed to.

I was hooked.

"How much?" I murmured softly. I knew there were vice cops in the area.

"Depends," he smiled, blowing smoke from his nostrils.

I glanced around furtively. There was no one on the street but us.

"Forty for the whole works," he declared flatly. "Hurry up an' decide, man. We're gonna get smacked by John Law standin' here like this."

I spoke without thinking. I was already hard.

"Forty then."

He nodded and moved away.

"Follow, but not too close."

As he moved away down the street my eyes were glued to his ass. Clad in worn jeans, it was just about the roundest, most delectable butt I'd ever seen.

I wanted it.

There was a cheap hotel near the bar, and I figured that was where he was taking me. So, glancing around one last time, I followed him, keeping a good three-quarters of a block between us. As I expected, he turned into the seedy lobby of the hotel, and I watched as he nodded to the bored-looking woman at the register and moved up the stairs, his pert little ass moving slowly from side to side, all but daring me not to follow.

The woman at the front didn't even glance at me as I ascended the stairs after the boy, who was waiting at the top landing. He jerked his head to one side, indicating a door, and I went past him and into the room. He followed, closing the door behind us.

The room was about what you'd expect. Dingy, dark, the only furniture a sad, badly used old bed. I was just about to turn around and speak to the kid when my eye caught the flash of his shadow behind me, moving fast. I spun around and caught his arm as the hand holding the blackjack descended toward my head.

He looked shocked. I don't think he expected me to catch on so quickly.

"You little bastard," I grunted as I pried the weapon from his fingers. He didn't put up much of a fight. I don't think he was used to violence, because I managed to subdue him pretty fast.

Once I got the blackjack from his hand I pushed him and he fell to the floor, landing hard on that cute little ass. He looked up, scared, and I tried to regain my breath.

"I guess the laugh's on me, isn't it?" I mused, feeling like an idiot. "That's what I get for letting my little head do the thinking."

I was idly slapping the blackjack against my palm as I tried to think of what to do next, but he must have thought I was going to use it on him, because he started pleading.

"Please, mister! Don't! I'm sorry! I really am! I--I've never done anything like that before!"

"Then why'd you try it on me? How'd I get the honor of being your first?"

"I--I'm desperate, man! I only been on the street a few days and I'm flat broke. I thought--you seemed like you might have some money, maybe, and I--"

"If you're really broke and you've never done this before," I sneered, waving the weapon close to his face and watching him flinch, "then how come you've got this little beauty?"

"I--I brought it with me when I left home. My dad used to use it."

"Like father, like son, huh?"

"No! He was a real mean bastard. Petty thief. I swear, man, he even used the damn thing on me a couple times. When he threw me out I came back to the house while he was gone and took it. I--I didn't know how tough things might be, an' I thought I might hafta use it to--to defend myself."

He was probably telling me the truth--or something pretty close to it anyway. I felt a tinge of regret for the parental abuse, but that didn't excuse his trying to mug me.

"Well, I can't just let you get away with this. What's to stop you trying to rob some other poor asshole?"

That got him. He sat up, fast, and was on his knees, his hands reaching for my trouser leg.

"No! Please, mister! Don't turn me in! Oh, fuck! I can't hack bein' put in jail. Oh, Jesus! I--I'll do anything you say. I promise. Anything! I'll let you fuck it out of me. You can take me home an' chain me up an' make me your sex-slave!"

"Okay, kid, okay. I get the picture." I stood thinking for a moment. I had this kid by the long and curlies. Now, what did I want to do with him?

I saw some relief pour into his panicked face. He knew I wasn't going to haul his cute little ass off to jail. And let some felon get a crack at that sweet butt before I did? Not likely! Besides, what was I going to say to the cops? "Um, excuse me, sir. I paid this punk for sex and he tried to rob me with a blackjack?" Fortunately for me the kid hadn't thought that one out yet.

"Anything, huh?"

Color washed back into the beautiful, scared face.

"Anything! I mean it! I'll--"

"I heard you the first time, kid."

He shut up and I smiled to myself. I could make this situation very interesting. Interesting and rewarding.

I sat on the bed, carefully placing the blackjack into my shoe and sliding my foot back on top of it.

"Stand up." He did so, shakily. "Now come over here."

He moved slowly, relieved but frightened. When he stood close enough I reached for the snap of his jeans and undid it, then slid his zipper down.

"Take `em off."

He stepped out of his pants and stood before me, shyly (and rather ridiculously, given the circumstances) shielding his crotch from my view with his hands.

I pushed his hands away and pulled him towards me. I reached for the elastic band of his tightie-whities and slipped it down in back, revealing that scrumptious round butt of his.

"W-what're you gonna do, mister?"

I stared into his eyes.

"Look. You dad was a total asshole. Beating up on kids makes me sick. But you need someone to teach you right from wrong. I think it's time someone put his hand to the seat of the problem."

With that, I threw him over my lap.

When I looked down at the naked butt lifted up on my knee I wished things had been different, because I would have preferred to strip it slowly. Bared it was everything it had seemed to be clothed, and more. This was an ass made for fucking--firm, boyishly rounded, dusted with blonde wisps so light it seemed hairless.

But I hadn't put it in this position to stare at it, and I didn't. I raised my arm and let my open palm fall across the half-melons, hard. There was a satisfying Smackkkk!! as my hand made contact, followed by a cry of shock and pain from the young hustler.

"Owwwwwwww!!!"

Smack!

"Ooooooooooo!!!"

Smack!

"No!"

Smack!

"Oh!"

Smack!

"Mister!"

Smack!

There was a sharp intake of breath through clenched teeth but I didn't give the kid any rest. My hand continued to whack at his bare flesh in an intense, but controlled, flurry of blows. First I spanked the right cheek, then the left, before varying the blows. I'd concentrate on the right cheek for a bit, aiming blow after blow, then abruptly switch to the left, then back and forth, finally returning to the left cheek again and applying a steady stream of spanks as the boy writhed on my lap, squirming and protesting.

Smack!

"OH!"

Smack!

"OW!"

Smack!

"Unnggghhhh!!"

Smack! Smack! Smack! Smack! Smack!

"AAAAAHHHHHHHHHHH!!!"

When the kid's hand flew back to protect his vulnerable ass I grabbed it and held it up near his shoulder and applied a new set of stinging blows across both cheeks at once.

Smack! Smack! Smack! Smack! Smack!

"AAAAAAAAAAAAAAAAaahhhhhhhhhhhhhhh!!"

By this time my arm was tiring, his ass was a glowing, rosy pink, and my cock was so hard under my trousers it hurt. When I stopped spanking him my hand slowly caressed his smarting buns and I became aware of the hard tent of flesh encased in the pouch of his briefs, poking against my leg.

He was breathing hard, and his ass was distinctly warm to my touch.

He moaned softly.

"Shhhh," I murmured, tenderly stroking his gorgeous butt. "It's okay. It's over now."

"Ohhhh, man," he whispered huskily. "Please fuck me! Fuck me now!"

I lifted his body up and placed him, belly-down, on the bed. Normally I like to fuck a guy on his back, but I knew the kid's ass was smarting and I didn't want him rubbing it against the bed's harsh sheets.

He lay there, moaning softly and pushing his hard cock back between his thighs as I all but tore off my pants and shorts. My cock ached as I unfurled one of the condoms from my back pocket over the shaft and greased it with a pack of lube.

I climbed onto the bed and placed a greasy finger against his hairless boy-hole. He relaxed his sphincter and I slid inside him, lubing him quickly before straddling him and aiming my dick at his entrance. When the tip kissed his asshole he pushed the rosebud open and, with astonishing swiftness, the head slipped inside.

He clamped down on me and I groaned. Then he relaxed again and I fed him the shaft, gasping as the head moved past the ribbed sphincter and my cock settled deep inside him.

"Is this what you wanted, baby?" I whispered.

"Yes!" he moaned. "Oh, yes. Fuck me. Fuck me hard!"

So I did.

Bracing myself with my hands near his shoulders, I used my hips and abdominal muscles, starting slowly and building greater momentum, depth and intensity as I went along. I arched my back and withdrew almost completely, just the head of my cock inside his hole, then slammed back in, deep, grazing his prostate, which caused him to gasp and groan beneath me. I did this a couple of times before I felt confident I could maintain contact easily. Now I began to fuck him with greater speed, breaking contact briefly as I pulled back, the head of my dick briefly withdrawing from his asshole just before I rammed it back in. I did this over and over, the upward movement growing faster and the penetration deeper yet, until I reached the base of what proved to be a stunning, powerful orgasm, the pulsations seemingly going on forever as wave after wave of spunk shot out the tip of my cock.

I fell on him, exhausted and still embedded deeply within his clenching hole. He rose up with his hips and I could feel the frantic motion of his palm sliding up and down the length of his cock until he cried out and the delicious, rapid spasms of his asshole against my spent dick told me he was cumming. The squeezing down on my super-sensitive organ made me dizzy.

His body sank to the mattress again and we lay connected, cock to ass, for a long time. Finally our breathing assumed normal respiration and I pulled out, rolling over onto my back and bringing him with me. I took his wet head in my hands and kissed him. He responded hungrily and we lay a long time, kissing deeply, our sweat-drenched bodies moving together on the dingy hotel bed.

I broke the kiss and smiled.

"So, are we even?"

He grinned.

"Yeah."

His face clouded over.

"What is it?"

"I hate goin' back out onto the street, that's all."

"Who says you have to?"

He sighed.

"Gotta make a living somehow."

"Not that way, you don't."

"You got a better offer?"

"I might. I need an assistant. You interested?"

His face lit up again.

"Am I!"

"I'll give you a place to live--"

"With you?"

I nodded.

"Three squares, and you do whatever little jobs I need. Okay?"

"Well--"

"Well, what?"

"Will we, like ... sleep together?"

"Would you like that?"

"You know I would."

"Then, yeah, we'll sleep together."

"Cool!"

"But that's not what you'll be paid for. Understand? That's for pleasure only."

"I get it."

"And will you--um--I mean, if I'm bad or somethin' ..."

I knew what he was getting at.

"You'll get spanked if you need it. Or if you just want it."

"I never knew I wanted it `til tonight. But I'll try not to need it. Seriously. I want you to trust me."

"I do, for some reason. Now go pay that ugly bitch downstairs her rent and meet me back on the street."

He kissed me passionately, then jumped up and got dressed quickly. I followed suit, but with less urgency.

"You won't regret this, mister--" He broke off, then grinned sheepishly. "Shit. I don't even know your name!"

I laughed, suddenly aware of the absurdity of the situation.

"I don't know yours either! I'm Stephen."

"Johnny."

"Don't make me wait long, Johnny."

He grinned again and sped out the door.

I shook my head in disbelief. What the hell was I doing?

Making my future a hell of a lot more interesting.