Teddy leaned against the lamppost and reached down to his groin, adjusting his meat. Goddam jeans were too tight; he made a mental note not to wear them again. Displaying the goods on sale was one thing; highlighting them to the point of damage was something else. Last thing he needed was to cut off the circulation to his dick so bad he couldn’t get it up for a john.
He hoped someone would come along soon. This part of the park was known for its boywhores and Teddy usually did a good trade here, but it was a slow night and he was jonesing for a bump. He needed money.
Plus, he didn’t want to be hanging out here all night. It was unusually cool for this time of the year, and he hadn’t thought to bring a jacket. His clothing wasn’t well-suited to the chill in the air either; his thin cotton t-shirt offered nothing but a chart of Pokémon characters across its front as protection against the cold. And while his feet were fine in his black Reebok hightops, the skillfully-done slashes above the knees of his jeans reveal his smooth, firm thighs—and also let in the night air.
In short, Teddy wasn’t in the mood to be picky. Coming from a broken, dysfunctional home, he’d been whoring himself out for years, quickly learning how to take dick from and give it to all sorts of men. If they had the cash, he’d do what they wanted—and sometimes, he didn’t demand much cash.
Tonight was different. Charlie had a big batch of the good stuff and Teddy was amped. Someone had to come along soon, preferably some fat old fuck who’d cum in forty-five seconds and hand him a wad of cash out of guilt.
When Teddy first saw the dude approaching him, he briskly rubbed his eyes. The man was a fucking stud; he damn sure didn’t look like the type who needed to pay for sex—which meant he probably wanted something beyond the realm of normal sex. Well, that was fine—as long as he could pay for it.
He was an older man, perhaps mid to late thirties. He was on the far side of the next streetlight, just inside the circle of light, and Teddy could see the guy was wearing a black leather aviator’s jacket that hung open and showed he wasn’t wearing a shirt underneath. Even at this distance, the young slut could make out the stud’s washboard abs and huge pecs, dusted with dark, virile hair.
The man’s face was shadowed with scruff that faded back from a dark goatee around his full, yet somehow harsh mouth. He sported a black ball cap worn backwards; a hank of dark hair had escaped from under the brim and lay across his forehead. His faded denim jeans were so tight that Teddy see that the dude was circumcised from nearly fifty yards away. But the denim ended at the knee; below that, it was tucked into a pair of 20-hole Grinder Cs Derby leather boots, also in black leather.
Despite himself, Teddy found his dick getting hard. That was a bad sign; this was business, not pleasure. He’d charge the guy out the ass—literally—but damn, he hoped the john wouldn’t be into anything too weird. He wanted to enjoy this.
The man kept coming. He didn’t smile—in fact, his handsome face seemed hard and emotionless—but Teddy knew the dude was coming for him, wanted him. Not that there was anyone else working this stretch of the street, but Teddy was pleased anyway. Still, though, he better have money.
He paused four feet from Teddy; the slut had the chance to check him out and confirm his first impressions; the man was a serious stud, muscled and hairy. This close, Teddy could pick up the heady odor of the john’s leather and the acrider scent of the dude’s testosterone, literally oozing form his skin.
“I wanna drain my load,” the guy growled abruptly, “You any good?”
“Make ya cum so hard you scream,” Teddy shot back, grinning insolently.
Teddy looked him over carefully, not from an erotic point a view but a mercenary one. That jacket and those boots weren’t cheap. “You c’n put it up my ass for two hundred.”
“You got the cash?”
The older man reached in his pocket and pulled out a wallet—also in black leather, of course—and gave Teddy a quick peek at the wad of twenties tucked inside. “You gotta place?”
Teddy nodded his head to the right.
“What, up the alley?”
“Yeah, unless you wanna pop for a hotel room.”
Teddy turned and led the way into the dark alley, ignoring the dude’s muttered “Fuckin’ street whore…” comment. He didn’t need to turn and see if the john was following him; the stud’s booted footfalls easily drowned out the faint sound made by his Reeboks on the filthy alley pavement.
About a third of the way down, behind a restaurant, was a dumpster. Teddy had been here often. Redolent of chicken scraps and rotting greens, it formed a perfect screen; the area on the far side got just enough light for johns to be able to find his asshole.
Unfastening his jeans, Teddy let them drop to his ankles, then turned to face the wall. He bent forward slightly, placing his hands up against the rough bricks. There was a pause as he waited for the fumbling at his buttcheeks that invariably occurred at this stage.
Except it didn’t.
“Take off your shirt,” the john growled.
Teddy sighed; he’d been afraid of something like this. He reached down and pulled the t-shirt up over his head, then balled it up and stuck it down into the denim hammock formed by his jeans at his ankles; he didn’t want it on the disgusting alley concrete. “Weird shit’s gonna cost ya extra,” he warned.
Sudden a pair of hand clamped Teddy’s hips tightly. Without a word of warning or a sign of any kind, the john was suddenly deep in the whore’s ass, his enormous engorged head grinding relentlessly into the punk’s colon, tearing at its tender lining as it plowed its way into his guts.
Teddy had been fucked rough; he’d been fucked dry, too. But it had never been by someone this incredibly well-hung. The dude had a dick like a horse and the slut had been totally unprepared for it; the pain was shattering.
It took all his effort to keep from screaming. He bit his tongue, savagely and deliberately, but he would not let himself cry out. Part of it was professional; it was a bad idea to make enough noise to draw attention to yourself when a john was fucking you. But for Teddy, there was also a matter of pride. He was gonna show this stud he could take it, no matter what. Even though he could feel blood trickling from his torn asshole, he wasn’t gonna let the fucker know he’d hurt him.
He could feel the hardbodied stud’s hot breath on the nape of his neck and hear the dude’s grunting as he pounded Teddy’s ass. The teen’s toes curled inside his Reeboks as the thick spongy head of the john’s hog plowed roughly over his prostate, forcing his already-hard dick to stretch and throb until it ached.
To accommodate the massive shaft impaling him, Teddy shifted his legs out, as best he could with his jeans shackling his ankles. But he could only go so far, his sneakers penned between the dude’s boots. Try as he might, the teen whore wasn’t able to find a position that made taking the dick any less painful; he’d just have to ride it out. But even though it hurt, it hurt good.
Teddy was surprised at the dude’s silence; he’d looked like he could get real verbal, but he hadn’t uttered a word since he’d started fucking. That was ok; a little abuse would have been fun, but the way he was reaming teddy’s fuckhole was amazing. The deeper he went, the less pain and more pleasure there seemed to be.
The teenaged boy might have been an experienced street whore, but he was still an adolescent whose lithe lean body had been pumped full of testosterone and other hormones by his over-revved nads with little way to control the reaction. He could feel his orgasm building as he got fucked up against a wall in a dark, dirty alley and he knew he wouldn’t be able to stop it.
As the swift slapping sound of flesh on flesh echoed off the grimy brickwork, Teddy could feel his balls begin to contract. Each plunge of the older man’s tackle into his anus forced a squirt of hot precum from the youth’s jutting, quivering shaft.
“Fuck, man,” he moaned as the john clutched his sweaty, heaving flanks in a vise-like grip, “I’m gonna blow…”
The muscled stud switched into overdrive; it was like a jackhammer had been jammed up Teddy’s ass. The pain was phenomenal; he’d never had such a vicious, brutal assfuck—and he loved it. He was surprised by his own reaction; the sheer agony of being violently used was getting him off. Part of him wondered what it meant, but rational thought faded was fading.
“I’m cumming—fuck, aw fuck—”
And for the next forty seconds, there was no coherent Teddy, just a shuddering teenaged boy, inarticulate and helpless as it spasmed in the grip of an overwhelming orgasm. As the boy grunted and jerked, a steady stream of hot boyseed splashed against the wall, spattering back down onto the kid’s hightops and the john’s boots.
“Aw, goddam,” Teddy moaned, gasping for air, “Fuckin-A, man—”
Suddenly, the dick was gone. He’d pulled out, quickly and quietly, with no warning. The trickling sensation he could feel wasn’t the john’s load, it was his own blood.
“What—” he began, and then he was on the ground. He had no clue that the sharp pain he’d felt had been a kick from a steel-toed boot to the back of his knee.
Teddy found himself lying on his back in a nasty puddle, looking up at the john. Something was very wrong. The man leaned over him, his knee-high boots shiny and glinting in the dim light. Above the massive cock, dangling over Teddy’s prone body, the stud’s huge chest and ripped abs could be seen under their haze of dark fur as the leather jacket swung open. But the light faded at the neck; the hard, scruff covered face was hidden in the shadows. Only a faint cold gleam hinted at the location of the john’s eyes.
“What the fuck?” Teddy demanded, his pleasure at getting reamed fading before his anger. “What are you fuckin’ doin’? Dude, you still owe me even if ya didn’t cum—”
“Goddam faggot,” the voice came out of the darkness, deep and icy in a way that chilled Teddy’s blood, “That wasn’t worth shit.”
Despite his fear, Teddy wasn’t about to give in. It had felt fuckin’ great, but this was business, after all. “You fuckin’ owe me. You better fuckin’ pay!” He tried to sound menacing; it came out as a whine.
The john took a step closer; the light bisected his face, leaving the top half dark but illuminating his strong, fur-covered chin and contemptuous smirk. He raised his leg and suddenly Teddy found himself looking at the series of X’s that made up the tread of the heavy black boot.
“Oh, you’ll get paid, all right, cocksucker,” the dude said quietly, his manner still coldly composed, “I’m gonna make damn sure you get everything a fag whore like you deserves.”
With that, he slammed his boot down onto Teddy’s chest. It hit the kid at the bottom edge of his ribcage like a piledriver, snapping two ribs and ripping his diaphragm muscle. “HORG!!” the teen slut cried inarticulately as air was forced violently from his lungs. The john ground his boot into the flesh, putting his entire body weight onto that foot.
Teddy, his eyes bulging in pain and disbelief, reached up and desperately clutched at the john’s ankle, feeling the smooth leather and tight laces under his hands as he tried to lessen the intense, grinding pressure on his midsection. The sadistic stud stood on the boy with that foot instead, using the other foot to kick the boy’s flank, hard, snapping another rib. With a choking cry, Teddy let go of the alpha’s boot.
“You fuckin’ piece a’ shit,” the john snarled, spitting on Teddy. The confused boywhore tried to wrap his mind around what was happening when suddenly the stud began kicking him brutally, driving his steel toed boots into the boy’s prone body. Squealing like a piglet in his fear and pain, Teddy curled into a fetal position to protect his more vulnerable areas.
It didn’t slow the vicious alpha down. Teddy’s exposed back offered plenty of flesh for the sick top to aim for. He wasn’t able to break all the homo’s ribs, although he tried. He scored a good shot on the cunt’s scrote, though; as Teddy brought his knees up to his chest, his balls dangled between his legs and were exposed on their back side when he rolled away from his attacker.
The impact between the hardbodied john’s Digger boots and the soft, pulpy tissue of Teddy’s gonads was so severe that Teddy’s left testicle was crushed like an overripe grape, blood and cum spurting over the whore’s taint and the alpha’s boot. The pain was more traumatic than anything the teen slut had ever experienced—he literally shot up in the air, coming back down onto his back again, splashing the oil-scummed water pooling in the alley.
His scream was piercing but brief. “Shaddup, cocksucker,” the top jeered, then kicked him again—this time in the face. Teddy shut up. He was too busy trying to maintain consciousness after having his jaw broken and three teeth kicked down his throat.
“Just another worthless faggot cunt,” the alpha growled, “Fuckin’ garbage that can’t even work the load outta my hog. Ain’t no one gonna miss ya, pansy!” He slammed his foot down on Teddy’s smooth bare chest and once again was rewarded with the splintering sound of breaking bones.
This time was different, as least for the teen slut. This time, in addition to the breaking ribs, Teddy felt a horrible pain as something tore deep in his torso, a terrifying ripping sensation—and then he couldn’t breathe.
He tried to inhale and found that he could, but just barely. It took all his effort to suck in air, and the pain was excruciating. He had no idea that his right lung had been torn open by the jagged end of a broken rib and was slowly collapsing; he only knew that he was dying.
The john saw it too, and didn’t stop. He kept applying his steel-toed boots to the mortally injured whoreboy, kicking him in the legs and hips, stomping on his arms. As he pinned Teddy’s right hand to the pavement and ground it to a useless wad of flesh and bone shards, the adolescent cunt felt drops of hot liquid spattering his face.
Prying his eyes open reluctantly, Teddy looked up to see the john’s huge cock dangling directly over him, dripping precum. The dude was watching intently as he inflicted physical damage on the teenaged punk, and he was getting off on it.
He hadn’t cum while fucking Teddy, but he was gonna cum while kicking him to death.
It wasn’t real. He wasn’t lying here nearly nude in a puddle of filth in a back alley, being stomped to death by a rogue alpha john. The pain was so intense, so severe, that Teddy was as disoriented as if he’d taken a huge dose of hallucinogens. But the stud’s words penetrated his trauma-hazed mind, reinforcing the nightmarish reality.
“Fuckin’ scum—gonna hafta scrape what’s left of ya off my soles like dogshit, haw! Does it hurt, cunt? You deserve this shit, bitch. I’m gonna kick you to death like a nigger, motherfucker!”
He kept his voice in control; the tone of joyous rage didn’t travel far down the alley, but it reached Teddy clear enough. The alpha didn’t think so, though; he felt the need to drive his point home and punctuate it with his black leather footgear.
Teddy could see the muscled john raise his leg; cruelly, time seemed to slow down, extending his suffering and giving him a chance to see approaching agony that he was utterly unable to ward off or abate.
The black X’s on the dude’s heavy tread glistened darkly as the boot dangled over Teddy’s nude, shuddering body. It was blood, the boywhore realized dully, his own blood. He felt no surprise or shock at the discovery—he was far too full of pain and fear for there to be room for other sensations.
Then the john began pounding him.
“Fuckin’ [STOMP] piece a’ [STOMP] faggot trash [STOMP], die under my boots [STOMP STOMP]!!!”
The tearing feeling again, much worse. The john had crushed Teddy’s other testicle, then slammed his feet so hard into the teen’s chest and gut that the punk had suffered severe injuries to his liver, stomach, and spleen and had punctured his other lung. As he painfully coughed up a huge wad of blood, air was escaping from his torn lungs into his chest cavity. In five minutes, the pressure would be enough to collapse both lungs and he would suffocate.
He didn’t live that long.
As he gasped and choked, expending more and more effort just to breathe, some part of Teddy wished he’d managed to get that meth; it would have made this so much easier to deal with…
Then the alpha kicked him twice in the face, the steel toes shattering his cheekbones and knocking four teeth out of his upper jaw. Suddenly an acrid, sour stench filled the alley. To far gone to maintain control, Teddy pissed himself.
The alpha chuckled. Placing his boot on Teddy’s throat, he stood over the dying adolescent and started jerking his huge, oozing shaft.
“Guess yer finally gonna get my load, boy,” he said with a wicked grin, “Lights out, motherfucker.”
Slowly and intimately, he crushed Teddy’s trachea under his boot, increasing the pressure until it gave underfoot like a beer can. As it cracked and crunched beneath his sole, the alpha grunted, a deep basso rumble, and spewed his hot jizz on the teen’s face.
Teddy felt his esophagus give way; as the older man’s boot destroyed his windpipe, the anguished youth jerked, his arms flailing and beating on the pavement until his hands were bloody. His feet, trapped by his lowered jeans, were no help to him, and as his face darkened and his tongue protruded in choking agony, the alpha’s spunk spattered across his face.
The last sensation Teddy received as he died was the salty taste of his killer’s sperm on his tongue. His cock pulsed and twitched but his faggot balls had been too irreparably damaged for the boywhore to experience a deathload. He quivered and died in a puddle of oily water, blood, and piss in in the foul-smelling alleyway.
Smirking, the top stuffed his still-dripping tool back into his jeans. He was still zipping his fly as he turned and headed back down the alley, whistling “Turkey in the Straw”. Behind him, as the tune and the heavy booted footfalls faded away, the body of the teen boywhore, battered and bruised beyond recognition, continued to tremble.
As the night wore on and the corpse cooled and stiffened, rats began to gather.
3 thoughts on “Boot Blackened Bitch”
That’s how i want to go out.
Me too, man, this fag needs to be brutally snuffed to make a real man feel good.
I agree, that wouldn’t be a bad way to go. I just wonder how much damage the Man could do with his fists? One thing I found so proper, was the crushing of the hustler’s useless balls. Fags don’t deserve to keep them.
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