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


by ScottR <playwright2@juno.com>

BOBBY I really got into this spanking _s_h_i_t_! Man! I mean, the guy was cute anyway, and when I pulled him over my knee and saw that hot butt waiting for me, I got a boner that wouldn't quit. As soon as I felt my hand hit that ass, and heard the CRACK! it made, I went wild! I got so carried away I even forgot about the signal he gave me to stop. All I could concentrate on was watching that _s_e_x_y butt of his turn red until he yelled at me to stop. And when it was over and I touched his ass, I was amazed by how warm his butt-cheeks were. And then I felt somethin' weird -- somethin' I never ever feel.

See, I know the game. They pay. You cum. Then they cum. Game over. I like it when it's happenin', but once I've shot I don't give a _d_a_m_n_. It's almost like drivin' a car with cruise control, you know? It' _s_e_x_, but it isn't. I mean, I don't put myself into it. I just get it up and empty it out.

When I first started husltin', I didn't like the feeling at all. It was like I was a machine or somethin'. It got so bad I even went with some of the pussy-boys. They thought I was hot, so they gave it up for nothin'. (Stupid, like I said before.) But when I _f_u_c_k_ed them, I still didn't feel like it was me. It was just my _c_o_c_k_ gettin' off, that's all.

Even with Officer Blake, that cop who's sweet on me. He's pretty cute, so the first couple of times I blew him, I tried to make it real special. You know, heavy on the _d_i_c_k_kissing, play with his balls. Stuff like that. But it didn't make me feel anything more than I usually feel. After a while, I just gave up tryin'. I figured it was part of the life, you know? To stop wanting to feel something more. I guess you could say I have no desire left. Maybe you can't have that if you make a living off other guys' desires.

But this was different. This was like -- I don't know, like it was somethin' I wanted. Except it wasn't complete. I don't just mean because neither one of us came, either. It was like I wanted somethin' more out of it. I couldn't figure out why, at first. But then ...

CARL I pulled up my briefs and reached for my pants.

"Thanks for the good time, kid."

"That's it? You're gonna get me all excited and then stop?"

"You did very well, Bobby," I smiled, putting my right leg into my trousers. "You earned your fifty."

The boy's face looked stunned.

"But --"

I was in the process of putting the other leg into my trousers, and I stopped, smiling enigmatically at the confused teenager before me.

"But what, baby? I got what I paid for."

"But you didn't cum, man."

Bobby's voice was taking on a slight whine which pleased me no end.

"I didn't say I had to. Was that part of the deal?"

I was putting my shirt back on now, and was tickled to see that the boy's face looked almost frantic.

"But I -- I didn't cum!"

I stared at him, still smiling in what I knew was a maddening way. I noticed that his _c_o_c_k_ was still hard inside his pants.

"Bobby, for fifty dollars of my money, I don't give a _d_a_m_n_ if you cum or not."

"But I thought -- I mean -- you --"

"Is there something you wanted, Bobby?"

He blushed. This tough little hustler was embarrassed by his own desires. He lowered his eyes and spoke as softly as he could.

"I didn't catch that, son."

The crimson deepened. Finally, he looked me in the eye and blurted it out.

"I thought you were gonna spank me back!"

BOBBY I only figured it out when I said it. It wasn't just that I wanted to cum. I did -- I mean, I had this woody that just kept gettin' harder and harder. But this little game Carl was playin' made me want what I gave him.

Like I said before, usually if a guy holds my butt-cheeks, I'll let him, you know, unless he gets a finger close to my hole. But this was somethin' different. I didn't want Carl to fondle my butt. I wanted him to spank it. Spank it hard like I'd just spanked his. Make my ass-cheeks red and warm the way his were. I'd been wantin' it since my hand first smacked his butt. All the time I was spankin' him, I kept wonderin' what it felt like. And wonderin' made my _d_i_c_k_ even harder. And the harder I got, the more I wanted to know.

But soon as I said it out loud, I started wantin' it like nothin' I ever wanted before. Maybe I needed it. Maybe somewhere along the line I wished my asshole dad had done it to me. I don't know. But I wasn't about to let this guy leave the room without tannin' my butt. I had to have it.

CARL This was going to be even better than I'd thought. I sat down on the bed next to him and looked thoughtfully into his eyes.

"Why, kid? Do you need it?"

He looked away. "I -- I dunno."

I put my hand around his shoulders.

"Do you want it?"

He started, as though I'd uncovered some secret he kept locked deeply within him.

"Yes," he whispered.

"Well," I said slowly, bringing my arm down around his waist. "Then maybe I'd better give it to you!"

With that, I slung the startled teenager over my lap. Without a second's pause, I gripped his naked waist tightly and ran my greedy hands along the curves of his adorable butt. I stroked his ass, cupping each cheek lightly. I laid my hand on its side and slide it up and down between his buttocks. Then I patted him gently. I teased him into a state of relaxation and then raised my arm up and brought my palm down fast across his butt.

WHACK!

"Oooofff!"

His lithe young body sprang up off my lap. I held him down and began to smack his ass over the thin seat of his jeans, paying special attention to the areas where the cloth was thinnest.

WHACK!

"Oww!"

WHACK! WHACK!

"Oooh -- OWW!!"

When the initial shock had passed, Bobby began to squirm and I held him more tightly. The jeans material bit into my palm as I spanked his bottom, and I felt his erection stabbing my leg. I paused in my labors just long enough to slip my fingers under him and unzip his pants. He didn't struggle, merely raised his hips up to allow the jeans to fall around his knees, revealing his tight little ass.

This is my favorite moment in the game: baring a boy's butt-cheeks while he's over my knee. I love the look of a young bottom that's about to get whalloped bare-assed -- especially if it's the very first time. Keeping a kid's jeans on, letting them slide down the legs behind him, makes the whole thing even more erotic somehow. My only regret is that he wasn't wearing underpants, which would have allowed me to warm him up some more, as well as giving me the pleasure of unveiling his hot butt a piece of clothing at a time. Those round buttocks lie there, quivering in anticipation, slightly reddened from spanking them beneath the boy's trousers, which lie in a rumpled pile around the knees.

Bobby's ass was everything I could have hoped for. Smooth and dusted lightly with blond wisps. The cheeks round and firm and waiting. I drank it in for a moment, my heart racing. Then I reached down to unzip myself. My _d_i_c_k_ was hard and straining to be free of my briefs. I lifted the boy in my arms and scootched my butt across the mattress to free it from my trousers, lifting up to allow the cloth to descend to the floor. Then I pushed my underpants down in front and repeated the procedure until they were gathered around my ankles. My _c_o_c_k_ sprang out and throbbed painfully. I was ready to begin.

I let my free hand travel slowly along the contours of the boy's perfect ass, cupping those delectable white cheeks and moving my knees wide so that they parted, giving me a fleeting glimpse of pink velvet before we began. Bobby's _c_o_c_k_, freed from his pants, poked against my thigh. I could feel a wetness at its head that coated my leg. We were both fully erect again, and the fun was just beginning.

As always, I lulled the boy by caressing his butt-flesh softly for a time, making him wonder just when the punishment would begin. Then, with a savage swiftness, I raised my hand suddenly and let it fall squarely across the dimpled left cheek.

SPLAT!

"God!!"

His butt was damp with perspiration, and the sweat made the sound of the blow on his ass-flesh resound with a sharp, satisfying sound. Now I really lit into him.

BOBBY I'd never, ever let a john take control like this before, and Carl didn't waste any time. He had me butt-up over his lap in a heart-beat, and the next thing I knew his hand was slappin' all over my ass. There was a sharp pain for every smack, but it wasn't the kind that makes you wince or cry. It was different. This pain made my whole butt feel like _s_e_x_. I've been sucked off by some experts before, and a few of those pussy-boys had assholes like a vise. But nothin' ever felt like this. It was like a shot of B-10, or a rocket goin' off up my ass. I felt like I could cum without bein' touch. It was like I'd been waitin' for this my whole life.

He pulled my jeans over my butt and then got himself naked from the waist down. When he started rubbing my ass, I felt a warmth that spread from his hand through my butt and out the head of my throbbing _d_i_c_k_. He kept playing with my butt, and just as I was startin' to wonder what the hell was goin' on, that hard palm of his smacked my naked butt and I _d_a_m_n_ near flew off his lap.

The sound of it in the room, the damp SMACK! his hand made when it spanked my sweaty ass-cheeks, the feel of my _c_o_c_k_ pressed up hard against his leg, the helplessness of bein' held down over the guy's knee -- it really turned me on.

Then the pain really started. I knew I'd smacked the guy's butt pretty hard, but I didn't know how much it would hurt! Oh, man! At first it was just a little sting, y'know? Then the sting turned into a hot fire. By the time the john had only spanked me a half-dozen times, my butt was burnin' up!

I started yellin', it hurt so much. But as much as it hurt, I wanted more. Before I knew it, I was squirmin' -- I couldn't help it! -- but he just held on tighter and kept on whallopin' my bare butt 'til the pain was like hot lava -- and my _c_o_c_k_ was so hard it hurt!

CARL Spanking young guys is nothin new for me, but paddling Bobby had a charge to it keener than any I'd ever felt. I didn't know why, I just knew I wanted it to last. So I slowed down to a crawl, letting the slaps get softer, putting more time between them.

I took the opportunity to admire my handiwork, and as usual I was quite pleased. The boy had fairly light skin, and it made the sharp declination of red on his bottom even sharper by contrast. Both buttocks had turned a deep rose color. And when I stopped and he was lying there panting, I reached under his belly and took hold of his _c_o_c_k_. It was a 7-inch steel rod, and I pushed it down until it was perpendicular to the floor.

The boy groaned and I brought his _c_o_c_k_ back to its normal position and began to stroke it, slowly and insistently. He wriggled beneath me, his flaming red butt-cheeks dancing and quivering deliciously as my palm caressed his throbbing prick, his hips pushing his ass up toward me as I stroked him. Then I curled my fingers around his balls, fingered his _d_i_c_k_ and, holding him in place by his genitals, raised my hand again and brought it down with stunning force on his left cheek.

SPLAT!!!

Bobby howled, and the force of his body's reaction sent his _c_o_c_k_ sliding up my palm and back down again when he lowered his hips. Satisfied, I smacked his right cheek. Again, the recoil sent his _d_i_c_k_ back and forth in my hand.

SPLAT!!! SPLAT!!! SPLAT!!!

With each new smack of my palm, the boy wriggled intensely and cried out in pain.

SPLAT!!!

"Oh, God!!"

SPLAT!!!

"OWW!! Ohh!!"

SPLAT!!!

"Oh, _s_h_i_t_! OWW!!"

SPLAT!!

"AARRRGGGHHH!!!"

Bobby squirmed all over my lap as I turned his bottom a fiery red. He was definitely hurting, I knew, but the whole time he kept shoving his hot little bottom up in the air to meet the next spank. And each time he did so his _c_o_c_k_ slid up and down in my palm. I could feel a more steady leaking of viscous fluid from the boy's _d_i_c_k_-head. If he wasn't close before, I knew it was only a matter of time now.

But rather than continuing, or allowing him release, I let go of his _c_o_c_k_ and balls and stroked his ravaged buttocks once more. As he began to relax again, the hot scarlet cheeks parted. I wet my index finger and pushed it between the crack, making direct contact with his puckered butthole. His body stiffened and his ass-cakes clenched tightly, trapping my hand between their erotic warmth.

To let him know I was still in charge, I spanked him sharply across both cheeks, one fast blow on each. He whimpered, but he relaxed. His spirit wasn't broken, but there was much more to come, and I smiled to myself, knowing that I had already won the biggest part of the battle. He had let me touch his anus.

BOBBY

What was happening to me? Here this john had me belly-down over his knees and not only had I let him spank my butt until it felt like it was gonna burst, I was even allowing him to poke his finger around near my asshole!

And I was loving it!

When his finger pressed in between my butt-cheeks, I tensed up automatically. But some part of me was thrilled at the feel of his wet finger-tip rubbing up against my pucker. Then he smacked me hard across my ass and I let my glutes relax. This wasn't the way things were supposed to happen, but I have to admit the whole scene had my _d_i_c_k_ rockhard. I couldn't believe I was letting the guy do this. Somehow, I had let him take charge. And somehow, I found myself not minding one _d_a_m_n_ little bit.

The next thing I knew, he'd got his finger all wet with spit again and was pushin' that sucker against my asshole. He kept it up, but it was slow and deliberate. I think if he'd just stuck his finger up my twat I'd have hollered bloody murder. But once I got used to the idea, I found myself bucking up with my hips, pressin' my ass back on his hand and sorta pushing out with my butthole.

When it was good and slick from his spit, he let the tip slip inside me. I panicked a little and squeezed shut on him, but he just smacked my ass again and I relaxed. I felt his finger pressing forward, slow but sure, and before I knew it he had it buried up to the knuckle. When I squeezed down this time, it wasn't to stop him -- it was just because it felt so _d_a_m_n_ good! My _c_o_c_k_ was throbbin' away and my butt was squirmin', and I heard little gasps and moans comin' outta my mouth, and I wanted him to keep goin'. Wanted to feel that finger slide all the way up my butthole.

Finally, I felt the whole thing inside me, and I sighed like a kid who's just eaten a big box of candy. But there was a lot more to come. He started movin' his finger around in my asshole, kind of teasin' it, and then he hit a little knot deep inside me, and my whole body went stiff. It was like he'd just shot volts of electricity up my ass! My _c_o_c_k_ jumped, my balls bounced, my butt-cheeks slammed shut and my muscles tensed from my head down to my toes. Man! Whatever he was doin', I wanted more of it!

CARL As soon as I touched his prostate, the boy went bananas. Didn't he know about his own prostate? I mean, here was a kid who gave his own body to make a living and his john was teaching him how to get pleasure out it!

That was all the encouragement I needed. I started finger-_f_u_c_k_ing his tight little boy-hole, starting slow and easy and working it up to full-fledged butt-rape. I pulled my finger almost all of the way out, so only the tip remained inside him, and his sphincter clamped down. I gently teased his rectum until it relaxed fully. Then I shoved back up his ass and glanced off his prostate. And each time I did so, his body lifted up off my lap and he gasped. Once I picked up the pace and started slamming it to him, he was gyrating all over my lap, moaning and crying out in ecstasy.

But he hadn't felt anything yet!

Now that I had him good and dilated, I moved to phase two, First I pulled the rumbled pants off his feet and tossed them aside. Then I lifted him up and carried him to the bed, laying him down on the cheap mattress on his hands and knees, with his hot red butt stuck up in the air. I cracked my palm across his left ass-cheek.

"Stay like that," I commanded. "Don't you dare move."

The boy complied, and I was gratified to see his _d_i_c_k_ was hard and throbbing. A drop of pre-cum glistened on the tip.

I got naked again and removed two items from my trouser pockets: a pack of condoms and a small tube of lubricant.

I approached the bed.

"Scoot up," I said.

He didn't even look back at me, just moved up toward the pillows without a word. I lay down and slid my body beneath him until my face was close to his butt. Then I reached up and gripped his cheeks.

"OW!!," he cried.

I lay another blow across his ass, the right cheek this time.

"Shut up, boy."

He whimpered slightly but kept quiet. I pulled his bottom down to my face and said, "Spread them."

He instantly did so, and I pulled the parted the cheeks toward me. His asshole winked teasingly, spasming. I squirted some goo on my index finger and stuck it against his anus. He moaned, flexing his cheeks. I smacked them, hard.

"Relax," I muttered.

Bobby's sphincter loosened and I slipped my fingertip inside, spreading the jelly around in his asshole. I slowly pushed upwards, making sure to massage his prostate a couple of times as I did so. His _c_o_c_k_ was thudding in the air between his up-raised thighs and I could see his balls roiling in their tight little hairless sac.

I added a second digit and worked his asshole like a gardener, softening him up and loosening the passage until there was no clutching at all. With my free hand, I petted his hot buttocks softly and reached between his thighs to stroke his wildly excited _c_o_c_k_. Finger-_f_u_c_k_ing his relaxed asshole rapidly, I pulled his butt-cheeks toward my face and kissed them. When he gasped, I sank my teeth into his bottom gently and began to nip those smarting red half-melons while gripping his ballsac tightly.

Bobby was moaning and sighing and pushing back with his hips the whole time, trying to get more of my fingers up his slick little boy-cunt. My own _d_i_c_k_ was throbbing wildly and leaking its own stream of pre-cum. It was time.

I slowly withdrew, swirling my index finger inside his rectum as I went. Then I stepped away from the bed and gazed at the boy. He was drenched in sweat, but he made no attempt to rise. He stayed where he was, his chest heaving and his perfect little naked body swaying on the mattress. I reached for a rubber, my heart thudding in my chest, and when I ripped open the package he tensed noticeably. He knew what was coming.

As quickly as I could I unfurled the rubber over my rigid sheath and squeezed out a large amount of lubricant, spreading it over my _d_i_c_k_-head and down the shaft. I felt like I could cum any second.

I patted his buttocks lovingly and mounted him from behind.


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