Hustling a Hustler (or Spanking & _f_u_c_k_ing), Part One


by ScottR <playwright2@juno.com>

CARL "Hey, kid."

The boy, feigning disinterest, rolled an eye at me. He continued to lean nonchalantly against the alley wall, hip thrust out, one leg _c_o_c_k_ed and the too-tight jeans hugging his basket.

"What, mister?"

He lit a cigarette and tossed his head, causing the long blond hair to slip away from his eyes. It was a studied gesture, like the way he thrust his left hand into his trouser pocket and "casually" rubbed his balls.

I saw something that looked like a pager stuck on his belt, and it struck me as weird until I realized he probably had police connections. I'd heard that sometimes a hustler gave it up for a cop, and if the policeman liked the kid especially well, he'd give the boy an emergency device. You know, those Medic Alert-type things. The kid would activate it and instead of calling the Rescue Squad, it alerted the cop and you'd have some heavy explaining to do in about a minute and a half.

"Want to make fifty bucks?"

I could see the teenager's lips tasting the money as his eyes, bored until now, focused sharply on mine. I knew his mind was buzzing. This was a kid who, if he was lucky, might get twenty every now and then but who probably made do with a fast fiver from guys who just wanted to suck him off. His eyes shone, but he held himself in check. A practiced sneer played on his lips.

"What's the hitch?"

"No hitch."

"Fifty bucks and no strings? Don't bull_s_h_i_t_ me, mister."

"No bull_s_h_i_t_."

"I don't catch. I'll pitch if you want, but I won't catch."

He had a defiant look, but I wasn't sure I bought it.

"You gay?"

"I don't catch, I said. If that's what you're after, you can just --"

"Okay, okay. Fine. You can pitch. Look, make up your mind, we're going to attract a cop here in a minute."

The kid paused.

"Okay," he shrugged. "As long as it's safe, it's your money."

"It's safe. You got a place we can go to?"

He tossed the cigarette butt into the alley and shrugged his shoulders.

"Come on," he muttered, moving out of the alleyway. "Follow me, but don't look obvious. I been busted once already this month."

The kid walked away. I followed at a discrete distance, enjoying the up and down movements of his slender hips and the roll of his tight little bottom. He certainly wore the right pants for his profession; the seat was worn deliciously thin and cupped his buttocks closely, accentuating their twin half-melon look. I could tell he wasn't wearing underpants.

I was already half-hard.

BOBBY I was standin' at my usual spot, just off an alley near the hotel. Sometimes the johns like to pull a quickie in the alleyway. It's dark and no one goes in there, and I guess they like the thrill of sucking a kid like me off where they might get caught. Actually, it's kind of kicky for me too.

I was leanin' against the brick wall of the old abandoned warehouse. It's my corner. A corner is a pretty important thing to have for a hustler. As long as you show up there regular and keep to your place, the other hustlers respect that. Every once in a while some greenie tries to muscle in, but they're usually just scared kids and if you handle them right they leave you alone. Hell, sometimes if they're cute enough and scared enough and you're strong enough, you can get 'em to bend over a trash can for you as an apology for trespassing.

The cops on the street all know me, and so long as I give 'em a blow-job every once in a while for nothin', they don't harass me. I don't usually suck a guy off, but when John Law wants you to go down on him, you do it. It's worth it in the long run, and anyway, some of the younger cops are pretty _d_a_m_n_ cute.

The way I work it is, I stand there against the wall and wait, like I'm just passin' the time. I wear real tight denims, faded and worn pretty thin in the butt that hug my _d_i_c_k_ and balls so the johns can see what they're buyin'. Then we negotiate. Five dollars and I get a hand-job. Seven-fifty and I jerk them off. Ten and the guy can blow me. If he wants me to _f_u_c_k_ him, that's fifteen. I always tell 'em I won't blow them and they can't _f_u_c_k_ me. Pisses some of 'em off, but I'm not gettin' into that routine. They'll think I'm some kind of fag, and I don't play that game.

See, every hustler has his own identity. Mine is acting like straight trade. I'll jack 'em off if they want, but that's as far as I go. There are plenty of kids on the streets who'll bend over, and that's fine. Sometimes I'll even send a john to one of them. But they've get reps as pussy-boys, and a rep like that follows you. Once the johns hear you put out, your price goes down. For one thing, it spoils their fantasy. The guys I service like to think I'm a straight boy, and don't want to imagine a stud takes it up the ass. For another, they figure you're desperate -- like you'd stick your butt up in the air for a fiver. Give 'em some head and they think they own you.

Of course, it's different when a cop wants it. That's my protection. But when they come to me, they know my limits, and for some guys the frustration can be a real turn-on. They all think they're the one who's gonna get me to give over. I let 'em touch my butt if they want, or even squeeze my cheeks, but if I feel a finger goin' anywhere near my asshole, the transaction is over. I mean like that! They get their money back and I send 'em to one of the pussy-boys around the block.

Anyway, the guy came strolling up to me, and I checked him out, casual-like. He was pretty hot lookin', but you don't ever let 'em know you think that. You act like you couldn't give a flying _f_u_c_k_, and that turns 'em on. When the john starts talkin' I usually stick my hand in my pants pocket and stroke my _c_o_c_k_. When it starts gettin' hard, they're pretty much hooked.

So the john offers me fifty but won't say for what. Now I gotta tell ya, fifty bucks is a big deal to me. A big _f_u_c_k_in' deal. I mean, that's ten blow-jobs! I'm 19, and even though I can get it up three of four times a night if I have to, no hustler can shoot ten in a row. And this guy's offerin' me three nights' worth of suck-offs for one hour!

I tried not to let him see how interested I was, but I wasn't sure if I pulled it off. I did warn him I wouldn't put out, even for fifty. He seemed cool with that, and he didn't look like a maniac, so I figured what the _f_u_c_k_? See, a hustler's gotta be pretty good at sizin' up a john. If they seem hinky, or act too nervous, or I can see a knife in their coat pocket or somethin', I'm outta there.

One of the advantages of givin' head to the cops is, one of 'em's bound to sorta fall for you. There's this one cop, Officer Blake, who's sweet on me. He gave me this "I've fallen down and I can't get up" thing I've got pager hooked to my belt. I press it and he's there inside of three minutes. Never had to use it, but it makes a good threat.

I hadn't really been busted like I told the john, but I wanted him to know it could happen. We have to look pretty casual goin' to the hotel, because you never know who's on duty. It might be some hard-ass who likes to push hustlers around. Better to be safe than sorry.

Like I said, fifty bucks is life for a couple of days. See, I'm savin' up my cash. I work free-lance, so I don't have to give anybody a cut except the night manager of the hotel where I take my tricks. He gets a percentage of my wages, and the rest I keep. I sleep wherever I can. Sometimes if a john is real sweet to me when we get to the hotel, I'll let him stay the night as long as he pays the night manager for it. But that's pretty rare.

Most of the time when the weather's warm I sleep in the warehouse on my corner. It's not run-down enough to be dangerous, and I've got a sleeping bag I keep hidden there. I hide in an old storage closet, and I've got a nice little combination lock for the hinge so the winos can't bug me. If it's cold, I pony up the cash for a room at the "Y".

I've got my money stashed away in a safety deposit box. I've only been hustling for two years, since my old man kicked me out of the house when I was 17, but I've got two thousand now and when I hit three, I'm gettin' a part-time job and a cheap apartment and goin' to trade school. I'm real close to my goal, and I figure one more summer of this and I can start a new life. So if this guy wants to give me fifty for an hour, I'll take it. Just as long as it's safe and he doesn't expect to pop my cherry.

I knew I should have made the guy state his terms up-front, but there was somethin' about him I liked. He felt safe. I know how stupid it sounds, 'cause one thing a hustler's gotta know at the beginning are the conditions. I mean, here this guy was askin' me to take fifty bucks and I didn't have a clue for what. I should have stopped the whole thing right there, and I'm usually _d_a_m_n_ cautious. But part of me really wanted to see what he had in mind. The mystery of it was kinda kicky.

Partly this john convinced me he wasn't some loony or psycho because he acted like the whole thing was as normal as a walk in the park. Maybe that's a chancy attitude on my part, but I've been lucky so far. Then he wanted to know if I was gay. I always tell 'em the same thing. Pitch, yes. Catch, no. If they want a pussy-boy, let 'em go around the block.

Once he got it that I wouldn't roll over and play dead for him, I said yes and we walked the block to the hotel. I knew he was starin' at my ass the whole way. I'm always careful to wear jeans that look like they're about to pop the seat so the trick stays good and turned-on. And I always go up ahead. When I'm walkin' upstairs in front of the john, I swing my butt as much as I can. Keep him interested -- let him get a good look at what's waitin' for him. Every once in a while a john chickens out, and I know if you're in front of him he can duck back down the stairs without bein' too embarrassed.

CARL After a block, the boy strolled into a cheap hotel. As he went by the front desk, the night manager passed him a key and the boy walked nonchalantly up the stairs, remembering to swing his hips as he went so that his bubble butt swayed enticingly. I followed, not daring to look in the desk manager's direction, but I don't think he gave me a look.

The kid stopped on the third floor and unlocked the door to one of the rooms. The paint was peeling and the hall smelled of stale smoke and spilled beer. I glanced around. No one in the dim hallway. The kid left the door open behind him, and I went in and closed it.

"Turn the lock, mister," the kid's voice called out from behind me. "To the right."

I clicked the door.

"Put the chain on, too. This place is full of scum-bags."

I did. When I turned around, I saw the boy was already stripping. His shirt was off and the nipples on his muscled little hairless chest were hard. I could see the outline of his _c_o_c_k_, already stiff in the tight jeans, and as I admired him, I also wondered, for the second time, about his defiant attitude.

"Don't take off anything else."

He looked at me, puzzled.

"Why? You wanna jerk off on my chest or somethin'?"

"No. Nothing that freaky."

"Hey, man -- I don't make judgements on what gets a guy off."

"Just stay as you are, okay?"

The boy looked at me quizzically, then shrugged.

"Whatever you say, man. It's your money. Speaking of which ..." He held out his hand, palm up, open. "Pay up, mister."

I opened my wallet and showed him the five ten dollar bills before taking them out and putting them in his palm. I made sure he saw that the wallet was conspicuously empty.

"You see this, right? That's all I've got. No credit cards, no ATM card, no ID, no hidden pockets, nothing. Just the fifty. So don't get rough or try to roll me later, okay?"

He nodded, arms folded across his naked chest.

"And you don't want me to take my clothes off?"

"Not yet."

"Okay, I'm cool. I see this one guy pretty regular, all he wants me to do is rub his crotch with the bottom of my foot through his underpants 'til he cums. Never even seen his _d_i_c_k_."

I took off my shoes, saying nothing.

"So, what is it you want, mister?"

"Call me Carl."

"For fifty bucks, I'll call you Tom Cruise if that's what you want."

"Carl will be fine. Let's not be ridiculous."

"Okay, Carl. So, what the _f_u_c_k_ you want me to do? Play Solitaire with you or something?"

"Sit down on the bed, okay?"

He looked at me guardedly, but sat.

"So. What do I call you?"

"Bobby."

"That your real name?"

"For fifty bucks you want my life story?"

"All right, don't get uptight."

I looked closely at the blond teenager beside me, admiring his face. He had a button nose that turned up adorably, thick eyelashes and large lips that made him look almost pretty. But the slender body attached to that face was anything but feminine. His belly was tight, his thin arms muscled. I figured he was eighteen, maybe nineteen, but I wasn't sure.

I could tell he was nervous. He was used to calling the shots, and I was threatening his power. I had a longing to take this boy in hand and teach him a few things. And if what I had in mind worked out, I would, soon enough.

"Look, Bobby. I'm your younger brother. You catch me jacking off on your bed. What do you do?"

He grinned.

"Shuck down my pants and join you, man! You're cute!"

He placed a warm palm on my thigh. I took it away.

"Uh-uh." I shook my head. He looked puzzled. "You have to punish me."

It sunk in. He looked up and grinned even more broadly.

"You want me to use my belt?" He placed his hand on the buckle.

"No, just your hand. Pull me over your knee, take down my briefs and spank my ass."

"Sure, man." His face was flushed with anticipation. "For how long?"

"I'll tell you when to stop. When I've had enough, I'll grab your knee."

"Okay."

"Now go outside and wait until I cough once. Then come in."

He shook his head, grinning, and got up. When he'd gone into the hall outside the room I unzipped my pants and stepped out of them. I'd decided to keep the fantasy simple for now, since I wasn't sure how far the kid would go -- or how agile his imagination was.

BOBBY: Even though this john didn't want me to get naked for him I'd gotten to feel fairly safe with the guy. Whatever yanks your chain, man. But it bugged me that he wanted to be in charge. That's not somethin' I'm keen on. I like to let my tricks know that whatever their fantasy is, they gotta let me take the lead. Still, for some reason I let him. Maybe it was his eyes. They were real kind looking. Deep brown, y'know?

I have to admit, he caught me by surprise when he suggested I spank him. Man, this was turnin' into one wild scene! I've done all sorts of kinky stuff for my tricks in the past. One guy gave me twenty-five just to watch me sit on the toilet and act like I was takin' a _s_h_i_t_, and another one had me call him every name in the _f_u_c_k_in' book while he beat off. But no one had ever asked me to spank him before. And _d_a_m_n_ if I didn't like the idea! My old man never laid a hand on me, so I wasn't scared of havin' my ass whipped. Hell, he was too doped up most of the time to even notice I was around. The only time he spoke to me in the last two years I lived with him was when he caught me and Jimmy Cole jerkin' each other off when I was 17. And then all he said was, "Get out of this house now and don't come back, or I'll kill you."

But this guy's fantasy was a total turn-on. It got me hard and kept me hard. I couldn't wait for his signal, so I could charge in there and blister his butt!

CARL

I pulled my underpants half-way down, releasing my already swollen _c_o_c_k_. Taking it in my hand, I lay back on the bed and took hold of it. I stoked the shaft, caressed the glans, tugged on my balls. Closing my eyes, I ran my fingers over the excited head, and imagined Bobby naked, which made me even harder. When I touched my piss-slit I felt a trace of pre-cum on my index finger. I didn't want to cum anywhere near this soon. I had to make this last ...

I coughed abruptly. I could hear the kid saunter into the room casually. There was a second or two of silence, and then:

"What the _f_u_c_k_??"

Bobby played his part well. My eyes flew open, and I stared at him, pretending to be startled. The bulge in his tight jeans was even more pronounced than before. No padding there. I also noted that his little nipples were erect.

"Didn't I tell you, Carl? Didn't I warn you? Didn't I tell you what I'd do next time I caught you jerkin' off on my bed?"

I reached down and tried to pull my underpants up, stammering. "But, Bobby, I -- "

"I don't wanna hear no horse_s_h_i_t_ outta you, you little prick! Shut up! I can see I'm gonna have to make myself clear to you."

Bobby flopped his little butt on the bed. God, but he was cute.

"Come here, you brat."

I whimpered.

He grabbed my arm, roughly.

"Come here, I said!"

I yielded, crawling on my knees on the mattress. Bobby yanked my arm and pulled me over his lap. Careful not to put too much weight on his young legs, I braced my body on the mattress with my hands and feet, so that only my crotch was tight against his body. He reached his left hand around my waist and held me down. I could feel the poke of his erection against my underpants.

"Boy, you just asked for an ass-whippin' you'll never forget!"

His practiced fingers pushed my shirt up in back, then reached for the elastic band of my shorts. Yanking them down in back to reveal my naked butt, he kept up a steady stream of invective laced with choice obscenities.

"Lousy little _s_h_i_t_. You think I like cleanin' up cum stains on my bed, you little _d_i_c_k_licker?"

I would have liked for him to start spanking me over my shorts, but I was willing to go with a bare-assed paddling if that's the way he wanted it. Bobby's dirty-talk was making his _d_i_c_k_ still harder; I could feel it rubbing against my crotch. My own _c_o_c_k_ was trapped in the pouch of my underpants, straining against the cotton. Warm air kissed my buttcheeks as the boy ran his hand along my flanks, softly tracing the rounded hills of my ass. Somehow, he had instinctively discovered the first phase of a good spanking: fondling the butt that's about to get beat. It raises the level of anticipation, extending the arousal and prolonging the moment when the spanking begins.

"Yessir, I'm gonna beat this bottom red! You won't be able to sit down for a week!"

I pretended to struggle, and he gripped my waist tightly. He ran his left palm across my buttocks lightly, rubbing the flesh and making me squirm in excitement.

"You got a nice ass," he said, cupping my right cheek.

"Keep your mind on the game, Bobby," I demanded.

"Oh -- right."

He'd dropped his role, and it took him a few beats to build up the character again. I helped him by wriggling as though I might escape. That did it. He gripped me tighter and brought his hand down, fast and hard across my rump.

WHACK!

His palm smacked my butt-cheek smartly, and a delicious painful tingling followed. I yelped and squirmed some more, pretending to escape.

"Try to get away from me, will you?," he barked.

WHACK! WHACK! WHACK!

The blows were falling all over my ass now, randomly, and hard. The first one had been a bit tentative, but the boy was really getting into it now, and his next series of spanks hit my ass like a series of bee stings. Pain exploded in my butt, and just as each new jolt receded, another one took its place. I was struggling now; part of the game for me was to make the paddling as close to a serious spanking as possible. And the harder he spanked, the more my _c_o_c_k_ throbbed. As the spanking picked up speed and intensity, I fell to pleading.

"No, Bobby --!"

WHACK! WHACK! WHACK! WHACK! WHACK! WHACK!

My butt was sweaty, and the spanks landed hard. It wasn't long before my ass was on fire from the boy's hearty slaps. The pain was greater now, the blows faster, and the sparks of stray tingling gave way to a full-out butt-burn. I wriggled on his lap, pushing my butt up, both dreading each new stinging assault, raising my bottom to meet it and falling back hard on his lap so that my hardened _c_o_c_k_ made maximum contact with his body.

"No! PLEASE --!"

"Shut up!"

WHACK! WHACK! WHACK!

The pain was more intense now, a steady, pulsing sting, and the blows fell into a rhythm. This boy was a natural! He's smack my right cheek, causing a fresh new blast of pain to erupt on my skin, then hit the left. He alternated for a while -- right, left, right, left -- then suddenly delivered a stunning blow square across both butt-cheeks.

My cries were growing more genuine by the minute.

"Oh, God --!"

WHACK!

"Ow!"

WHACK!

"Oh!!"

WHACK!

"OWWW!!!"

WHACK!

"Unhh!!"

WHACK!

"Oh! Ow! No!"

"You've had this coming, asshole."

WHACK!

"Ohhh!!"

WHACK! "Oh! OWW!!"

WHACK!

"UNNNNHHHH!!!!"

WHACK!

He was completely into the scene now. His hand was flying up and down, smacking butt at a furious rate. For a guy who'd never done this before, he instinctively knew how to vary the spanks; first my right cheek would feel the sting of his callused palm, maybe two or three times, then the left would absorb his smarting blows. Then he'd smack both cheeks once, twice. All the while he muttered obscenities at me, his rigid erection pressed tightly against my crotch. To make it more interesting for him (and for me), I threw my arm behind my back and tried to shield my reddening bottom. He jerked it up behind my back and whalloped me even harder. The air in the fetid room was alive with the wonderful sound of hard flesh striking soft.

My butt was in flames, and the constant wriggling against his knee was bringing me close to orgasm -- too close. I grabbed his leg, but he was so carried away with spanking me that he kept on raining hard smacks on my battered ass.

"Bobby!," I gasped, gripping his leg more tightly. "I'm telling you to stop! Remember!"

The punishment ceased. I lay panting over his knee and he muttered, "Sorry, man. I got carried away." His hand caressed my butt-cheeks gently. "Wow," he whispered. "Your ass is really warm. You should see how red it looks."

He let me up, and I lifted myself from his lap slowly, my butt burning from Bobby's agile hand. When I turned around, he was rubbing his palms over the hard column that poked against his jeans.

"God, that is SO hot. Oh, man, I've got such a hard-on!"

I couldn't tell if this was his usual line to get a john to suck him off or not, but I wasn't ready that in any case. I wanted to tease him as long as I possibly could. Then when I had him on the verge ...


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