Sleeping Ruff
#17 of Quickies
One of a few stories I've been working on since I started my break. WEREWOLF ANAL SEX with a creepy stranger, so don't say you haven't been warned!
On a more serious note: If you enjoyed this story, I'd really appreciate it if you donated some money/clothing/whatever to help out the real life homeless shelters or food banks in your local area. Being blackmailed into sex with creepy strangers because you're desperate in real life not nearly as enjoyable as described, so giving people the option to say no and maybe see them through a rough patch would be nice (I think) at this time of year.
The cold, rainy nights were the worst. That was one of the early things he'd learned in the couple of weeks since he became homeless. It felt like months, but the Christmas decorations were still up. Just thinking about Christmas made his stomach rumble. He had some money - just a few pounds in change - but he'd been saving up to try to get a room somewhere. It was always a gamble: eat now and freeze later, or starve now but maybe get somewhere warm to sleep.
While it wasn't raining tonight, the icy wind was cutting through all the clothing, which he wore almost constantly except when he'd splurged on a small room with a communal shower. It was also Friday, meaning drunken idiots wandering around, making getting to sleep even harder with their noise. He curled up under the bits of cardboard he'd collected earlier, waiting for either death or sleep to claim him.
"Hey buddy, need some help?" a heavy voice growled.
He waited motionlessly. Most of the time it was just people talking on the phone. Sure, tonight he was in a dark alley, but again: Fridays brought out the worst in people. He was only sure he was being addressed when he felt the end of a wide, heavy book gently push up against his back.
"Hey, hey," the voice badgered.
Exhaling nervously, he turned over from where he'd been facing the wall, wincing as the lights from the street bounced around the corner. The owner of the voice was a large, looming mass of black. His first thought was "Who the hell still wears a hat and a trenchcoat?" His second lingered on what kind of person might do that kind of thing.
"I gotta place you can stay," the figure offered, only barely swaying as though he was impatient.
His heart pounded excitedly, but he sat up cautiously. The figure was leaning over him, a massive arm pressed against the wall, the thick fist bristling overhead. His other arm disappeared into the wide blackness of his body. It didn't look like he had a weapon, but this guy probably didn't need one. Then again, he might have been homeless too: since he'd sat up, his head was closer and there was no escape from the heavy, wild musk that poured down on to him. "R-really?" he stammered, just waiting for laughter from the figure's drunk friends to roll down the alley and for them to go enjoy their lives, leaving him feeling even more shitty. "Ah, thanks," he added.
"It ain't free," the figure said, "can't bring every guy I see sleeping rough, even those young and cute like you." By now, he was used to the disappointment, so it didn't faze him. Before he could turn away, the figure added, "Wanna show me how much it's worth to ya?"
His heart was still pounding, but now it was nerves rather than joy. A slick, pointed fleshy tip jabbed him in the forehead. Apparently the price for a roof over your head was - at least - a blow job. Normally, he wouldn't have thought twice about doing so; but that was before giving head would provide him with a pillow. Discomfort swept through him: he thought of all the diseases this guy might have, maybe even some fatal ones. It might not stop at oral, or even normal sex acts.
But he was cold, and those were tomorrows problems.
"I've, uh, I've never, uh..." he explained.
"That a no, then?" asked the figure confessed.
There it was: the out. He could - maybe should - have taken it, but there was still a long time before it got quiet enough for him to drop off. "N-no, I just don't know what to do," he confessed.
The figure chuckled, "Just open ya mouth, you'll figure it out."
He sighed, hating himself even more than he did. Closing his eyes, he steeled himself, then relaxed his jaw.
His lips had barely parted when the figure's slick cock pushed into his mouth. He quickly knew this had been a mistake: aside from being big enough that the first couple of thrusts were already hurting his jaw, there was something definitely wrong with this guy's dick. Not that he was an expert, but he had one himself. He knew the skin on them wasn't this smooth for several inches: maybe the head, but nobody's cock had this long and thick of a tip. Nobody normal, anyway. The shape was wrong, too; it was like the tip of a tongue was scraping along the roof of his mouth, only it was drooling salty, thick fluids down his throat. At least he understood the warmth, and this guy's weird cock was definitely warm as it pushed inside.
The figure was enjoying himself at least, growling, "Oh yeah, that's good. Open ya mouth a little wider, though, and breathe through ya nose."
Not wanting to risk pissing off a big, horny and possibly crazy guy, he went along with the request, keeping his eyes closed as he was fucked in the mouth. It felt slow, like the figure enjoyed taking his time, sliding his thick, smooth, throbbing cock into his mouth. He felt a gloved hand slide in between the back of his head and the brick wall he'd been trying to sleep against.
Then realised it wasn't a glove.
His eyes snapped open, scanning the shadowy figures body to confirm the stupid, impossible thought that had popped into his head. He didn't like the answers he found: even with the weak light, he could see the figure was covered with a mass of fur. The homeless scent he'd been smelling was just the creature's musk: heavy masculine, and cut with tones of wet dog.
The figure was a werewolf. Maybe something close enough to one to not matter enough, but in his experience, it was the best word for the creature grabbing the back of his head, growling encouragement and excitement as it pushed a monster cock - in more ways than one - into the stupid mouth he'd offered.
Screaming didn't help; he gagged as the werewolf, presuming he'd been opening his mouth, pushed in deeper. The trickling ooze of pre-cum into his throat should have made it worse, but instead it just sent tingles through his tongue, lips and mouth. Whatever it touched seemed to quiver with energy, before becoming pleasantly numb.
That didn't calm him down though. He tried to squirm away, but the werewolf was strong, thrusting in. His mouth filled with the monster's strange cock, deep enough to give him a good sniff of his furry crotch. Unsure of what to do, he raised up his arms, grabbing the hairy, thick legs of the beast.
"Guess ya finally noticed, huh?" the werewolf declared, "Don't matter, ya'll get used to it."
He wasn't sure what the werewolf meant. Nervous sweat poured out of him, his grip slipping down the thick, though surprisingly smooth, fur of the werewolf's legs. He put it down to the werewolf being so close, giving off a lot of heat, because he didn't quite feel the icy teeth of the night air piercing into him. The sounds of the street were muffled too, now that his head sat between two thick, furry thighs. If it weren't for his head being shoved down the werewolf's thick, drooling cock, it would have been almost nice.
His fingers slipped through the fur on the werewolf's legs, having stumbled into touching him accidentally. He didn't want to touch him - he didn't want to make it seem like he was enjoying himself - but he also didn't want to piss off the guy holding claws to the back of his head, so he had to be sly about it. The fur was surprisingly smooth, not as gnarled as he'd have guessed. From what he felt, the legs were shaped like those of dogs; his nervous mind briefly distracted itself, wondering if he had paws under his boots. He couldn't imagine that would be very comfortable.
The werewolf's cock squelched inside his mouth. Saliva and pre-cum were sliding down his chin, oozing down his skin under the several layers of clothing he wore to ward off the cold. He wished he could spit, or even swallow. It wasn't hurting any more, chalking that up to getting used to it, but fluids were pooling in his mouth with nowhere else to go but out, and he couldn't do anything about it. It didn't help that the werewolf's salty, hot cock seemed to be aggravating his saliva glands into working overtime.
Even the werewolf seemed to notice this, slowly sliding his dick out. He finally got a look at it: the slick pointed shaft glistened in the lights, thrusting out of the werewolf's dark, massive body. It twitched a bit, squeezing out a drop that the werewolf's thick, padded thumb pulled off. Now both of the werewolf's paws were on his head: one still clinging to the back of his head, slightly tugging off his woollen hat, the other tracing a line down his perspiring forehead.
"Gotta mark ya," the werewolf informed him, "so everyone knows yer mine." The paw continued to trace the line down his nose, the thumb sliding into his mouth to rub slowly on his tongue. He had no clue what the werewolf was trying to accomplish, but the first thing that came to mind was beheading.
Instead, the werewolf slipped his thumb out, his clawed fingers slowly closing his still-open mouth to rub his throat. "We ain't done yet," the werewolf informed him, "but ya got ta pace yaself." The rubbing made him want to swallow. He coughed - it started going down the wrong pipe - and the werewolf seemed to laugh at that. It was a little hard to tell what the werewolf's mood was, other than his erection, he only had his words to go on, and they all sounded gruff and dangerous.
"Yeah, breathe this in," the werewolf suggested, the hand on the back of his head pushing him forward. The werewolf's cock slid over one side of his face, threatening to jab him in the eye. Suddenly his nose was right amidst the base of the werewolf's shaft and where the prickly, large orbs dangled in. He breathed in, his body forced to absorb the hot musk pouring out of the horny werewolf's body. The scent was almost liquid, pouring down his nose, and then his mouth when he opened to try to catch his breath. He splattered the crotch in a spray of saliva, as he moaned.
His body twitched uncomfortably; he fought to try to gather his thoughts, which scattered around, flashes of the werewolf in front of him bursting in to kick everything around in a flurry of fur, fangs and fucking.
His hands dug into the werewolf's legs; he'd not had the chance to let them go, and now he needed something to grip onto that was real. He felt envy: the werewolf was strong and muscular, and although he wasn't exactly a weakling himself, he didn't feel the self-confidence that was almost literally pouring out of the creature in front of him. He started to stroke the muscular legs absent-mindedly; the werewolf in turn started to stroke his hair, knocking off his hat.
"Feels good when ya give it a chance, eh?" the werewolf muttered, slightly distracted by a sound from the street. He'd barely noticed anything, though slowly caught on to the fact there was an uncomfortable silence. Finally, there was a rushed, laughing apology, and things went back to normal.
Or what passed for one when you'd offered to suck off a werewolf.
The werewolf legitimately growled this time, "Fuckin' drunks. Wish we coulda taken this somewhere more private, but it's a bit late for that now. Kinda hard to keep yaself contained when ya just need ta fuck, am I right?"
He grunted in response. The musk seemed to have corrupted the air - all he could smell was werewolf scent - and had opened his mouth to get oxygen. He'd started to pant, which led to him inadvertently licking the werewolf sack.
The werewolf took this as a sign of approval, "Yeah, I can see ya feel the same. Betcha feeling really hot, too. Why don't we getcha outta all those clothes ya wearin'?"
"N-no!" he stammered, "Someone might see..." The words froze in his mouth. That wasn't his biggest worry.
"Nobody's gonna notice," the werewolf assured him.
Paws reached down to grope at his outer layers; he froze up, hands still running over the werewolf's legs, at least until the werewolf crouched in front of him. Two emeralds gleamed, dark pupils shifting over their surface. Large, white fangs gleamed as a broad grin broke out. He could almost feel the creature's fat cock dangling somewhere in the air between them, exuding heat like a raging fire.
"Boy," said the werewolf, "ya gonna want to get out of them clothes in a few minutes, but it'll be easier for ya if we get started right away."
"What the fuck is he talking about?" he thought. There was no way for the werewolf to know how oddly warm he felt, as though it was some balmy summer evening in a more hospitable climate than this. He was actually sweating, or had been sweating; he couldn't really tell, since the werewolf had been pawing at his face, and whatever dampness was coming off of him had been absorbed into the dirty shirt and underwear clinging to his body since the last time he rotated clothes.
The werewolf's clawed fingers grabbed the collar of his outer jacket, pulling it off. He'd been lucky to find it: it was leather, and aside from a few holes it kept him mostly dry and warm. He didn't want to lose it. Then he remembered - the werewolf had offered him a place to sleep, so he wouldn't need the jacket - so stopped struggling while it was removed.
Besides, there was too many distractions. His head was still swimming from the werewolf's musk, and now that he no longer felt cold, scared and tired, his body was relaxing. Even though he wasn't feeling aroused - although he did admire the fact that, if he had to blow a monster man, it had been a rather handsome and well-built one with some wicked green eyes - his cock did start to thicken as his blood started to flow more freely.
His jacket was off now, the werewolf careful to fold it up and put it on some of the cardboard he'd been sleeping under, and not on the dirty ground. "How nice," he thought, "just like a dad folding laundry. A big, hairy, smelly, strong, hot dad."
"Huh?" he mumbled aloud.
The werewolf looked at him, equally confused. "I didn't say nothin'," assured the werewolf as he hooked his claws into the bottom of a stained woollen jumper.
He didn't know where his mental outburst had come from. He wasn't completely addled: the werewolf wanted him naked, probably because he wanted to fuck him like a dog. The confusion came because now he found the idea not just not unpleasant, but something to look forward to, to enjoy. He hadn't enjoyed sex, well, ever. He'd jerked off, to help him sleep and to pass the time, or because he was just a horny, dumb kid and it felt good. This felt like that: the same stupid buzz where you reached your hand down and grabbed a werewolf's cock because the hot shaft was just waggling about there, just waiting for you.
"Oi, hey," the werewolf yelped. Noticing what it was, the monster's green eyes seemed to glow with a nasty energy, "Heh heh. Well, boy, we gotta warm ya up proper first. Those hands are like icicles."
His hands went down to his own crotch instead, his fingers shaking and fumbling to undo the buttons of one of several pairs of jeans he was wearing. His erection was getting painful being contained as it was, squashed against his leg. He was intensely aware of how sweaty his crotch had been, with the sensitive exposed tip squirming around the inside of his hips in a struggle to escape.
Under the werewolf's instructions, his arms went up. The thick fuzz on his face crackled as his sweater was yanked up around his arms. Tilting his head up, he looked to the cloudy sky, wondering if it was a full moon tonight, or the werewolf turned every night. Maybe he was just like this all the time? Maybe he transformed when he wanted to, or when he got horny?
The sweater slipped over his head, the werewolf's cock bobbing in view. Suddenly, he didn't care what the werewolf thought of his cold hands. He grabbed on to the werewolf's firm, hairy rump and slid his open mouth over the throbbing red shaft.
"Oh, fuck me, boy," the werewolf growled.
He was sure the werewolf was telling him off for not getting undressed more, but he couldn't help it. "If you didn't want your cock sucked," he rationalised, "you wouldn't have come here and waggled it in front of me like that." The penis slid further in as he relaxed his face; now that he was into it, things were a lot more comfortable and definitely more enjoyable.
"Fuckin' shit!" the werewolf yelped. He wanted to grin: the big bad wolf was apparently a big hairy baby when it came to having someone squeeze his ass. Something hard scraped behind him, and bits of dust fell about, swirling in the air; the werewolf sneezed, involuntarily thrusting deeper into his waiting mouth.
"Urk!" he protested, pulling back to catch his breath, but not before breathing heavily. The werewolf's musk was heavenly. Pure manliness. Pure potent animal strength. Just thinking about it made his tongue lol over the end of his front teeth.
Pulling off of the werewolf, he noticed his face, bulging out further into his vision. The top of his nose had started to flatten, and streaks of black curled over the edge like grasping claws. Lifting his lolling tongue, he checked around his mouth, feeling along the curved sharp tips that hadn't been that way before. Prickles of grey dotted the bridge of his nose. His mouth stayed open, as he quickly checked his hands. Darkened fingernails. Thick pads of flesh swelling on the tips of his fingers. Patches of small fur racing up his sleeves.
"I tried to tell ya, boy," the werewolf seemed to chuckle, "we don't have a lotta time, and it's mighty uncomfortable to be wearin' too much clothes."
He felt stupid: how had he not noticed this earlier? Even though he was aware of what was happening, he wasn't scared. But he was torn: the werewolf's cock, freshly lubricated by his saliva, twitched and glistened needingly, while on the other hand he was starting to feel increasingly uncomfortable and confined in his clothing. Getting naked won out, if only because the hot werewolf had been the one to mention it.
Fumbling on his pants again, he mumbled, "Uh, can you rip through the rest?"
"I can try," the werewolf obliged, piercing the next layer of tops with his claws.
The buttons were incredibly stubborn, and with his added clumsiness from the changes to his hands and feeling too distracted to really concentrate on getting it right, it took one ripped shirt to finally get it off. Having the werewolf standing there, erect and with two pieces of thick fabric in between his hands gave him enough of a push: he wondered briefly if his dick finally got tired of being stuck that it pushed the button into the right place in his hands.
Breathing heavily, he moved on to the next; fortunately, he was only wearing a couple of layers of pants, and once he'd removed one his speed improved. The werewolf continued to tear off his shirts; he enjoyed the feeling of the claw running along his spine, his hot, pulsing body getting closer to being naked and free, and ready.
The shirts had trapped in his body odours; while he sped up on removing his pants, the werewolf seemed to slow, taking longer to plunge his snout into the clothing he'd just torn off.
He was finally down to his boxers, and he felt his heart starting to pound: only a couple of ratty layers left. They were barely containing anything: his tail - admittedly still short - sprang out of the back of his pants immediately, almost as stiff as the cock that thrust out. His manhood had swollen not just from arousal, but from the same thing that had changed the guy he wanted inside him. Foreskin had thickened into a heavy sheath, the tip of which had curled back. His erection was still mostly human, but it had lengthened considerably, and it was showing signs of deformation. Fur bristled out of his legs, which started to ache from having to constantly change balance as his bones and muscles went through short bursts of destruction and renewal.
What he wasn't prepared for was his own scent, wafting up free. To him it was incredibly relaxing, relieving him of what few inhibitions he still had left about getting naked with a strange werewolf in a dark alley.
On the werewolf, however, it was more pronounced: his forceful approach earlier seemed almost gentlemanly. The last shirt was quickly torn off - even though that was no longer necessary - and the monster had dropped to all fours, hind paws straining uncomfortably against the boots. A snout was brutally shoved into his crotch, only to have him tumble over onto his fur-peppered back.
His own nose continued to expand, his own lycanthropic muzzle slowly taking shape. It was surprisingly painless; in a way, it felt kind of good. The first analogy that came to mind was a cock: swelling into an erect state, growing and strengthening. That's what the transformation was like, like his human body was finally growing into its full erect state. Only it happened to involve growing a massive amounts of fur and fangs.
"Ooh," he moaned: thinking about penises caused a throb to slide down his own. Even though it was fully erect, it still seemed to be pulsing and expanding, and now twisting, as though the human shape he had wasn't big enough to contain the rampant beast of lust caged within.
He rose, but still crouched: now that he was naked he didn't want to be seen. The other werewolf - there wasn't hiding the fact he seemed to be becoming a werewolf himself - had disrobed, not caring about being seen. "Guess it helps if you're on all fours," he thought; nobody was going to take something large for a man and confuse it for a dog, but if you weren't looking too hard down a dark alleyway, and all you saw was a skulking four-legged furry creature, maybe it escaped notice.
Putting his hands onto the ground, he looked at the werewolf. The paved ground felt so odd beneath his hands. His claws bent up on the rough parts, pulling on the flesh of his mostly-furred fingers. The padding helped too, like the callouses he was sure to have on his feet if he'd not had boots. He wondered what his feet looked like. He could feel them changing: the claws piercing through the layers of socks he still had on his feet, the strain on the back of his footwear as his feet lengthened and widened. The odd contraction of his shins.
"Good boy," the werewolf growled approvingly, feet falling out of the boots almost as if to show off what he couldn't see of his own. Wide thick paw pads, truly the hind legs of a beast, but way too big to belong to a natural dog to offer just enough support to allow one to stand upright if one wished.
Right now, neither of them did. Their noses were drawn to sniffing each others scents, each feeding off of the musk of the other to maintain the rock-hard erections that jutted below. One thick and dripping, ready for action, the other growing, stretching, deforming into something belonging to a creature midway between man and beast.
The werewolf started to lick his hole, a natural extension of the butt-sniffing they'd been giving each other. He was tempted to do the same, but he quickly realised what was happening, and decided not to: the werewolf wanted to fuck him, after all. And he was okay with that. More than okay. He panted, tongue sliding out of his muzzle, trying to relax down there. Having someone tonguing him down there felt so weird. It wasn't bad, just not something he'd experienced before. The werewolf knew how to use his tongue, massaging the ring, then slowly working.
He stretched his legs, his feet finally slipping out of his footwear but still stuck in his socks. That was okay, he decided, they could be gotten rid of later. His cock was rock hard. He felt the juices dripping down it. His panting was heavy, clouding the air around him. Suddenly his past, his misery, didn't matter. He didn't care about when, or if, he turned back into his old self.
He just wanted the werewolf to stick it in him like two back-alley dogs going at it.
The werewolf obliged, the tongue disappearing from his hole and a massive weight bearing down on him. The werewolf's body was immensely hot: even through the fur on both their bodies, he could feel the massively powerful muscles flexing on top of him. The monstrous unsheathed cock jabbed at his behind, sliding up between his balls and leg. It poked about blindly. Above him, the werewolf grunted and growled - not at him, just out of his own frustration - and he instinctively growled too when it got really close to getting to the right spot. Even growling came natural, the thought causing a weird rush to pass through him.
Then the werewolf's cock got close enough that the pointed, dribbling tip slipped in just enough. There was a sudden thrust forward; he yelped - hoping it sounded enough like an animal to go uninvestigated by the passers-by - and it hurt a little as the insistent dick stretched his hole wider than he was comfortable with. But overall, it was satisfying: his own cock throbbed, and the werewolf dared to put one hand up to scratch his furry chest, which turned into a sliding motion that reached down the length of his body, sliding down towards his groin.
The first thrust into his ass happened; the werewolf on top of him grunting with the effort of forcing a large dick into a tiny, slightly lubricated, hole. The heavy breathing was contagious, and he found his own mouth staying open, drool spilling over the sides of his chest as their two bodies rocked together.
He panted, the werewolf cock creeping in. It kept trying to slide out; he guess that made sense. However, it meant the werewolf had to slowly, but continually, push forward, the cock oozing inside his hole at a snail's pace. Clenching his jaw, he breathed through his teeth as the fleshy shaft wriggled deeper into his body.
Suddenly they both shuddered forward as the erection slipped forward quickly. His eyes rolled up into the back of his head. Something triggered, the pointed tip of the cock impaling him touched his insides in some strangely attractive way. The werewolf backed off slightly, before pushing forward again, just a little bit more than last time.
This slow expansion of his hole took quite some time. The ring began to throb, slightly irritated from the rubbing. He could feel it opening wider. The werewolf's thrusts started going deeper, and pulling back further. Pounding on his ass, the werewolf started groping him, tugging on the exposed part of his cock, more of his lycanthropic shaft sliding out.
Starting slow, the werewolf sped up quickly: the thrusts became fervent slams that send his fuzzed sack swinging about, the strokes becoming hard and rough. He tried to dig his claws into the ground for traction; instead, he just hurt his fingers as his claws met stony pavement. Werewolf cock smashed into his tender, pliant insides, the fluids itching as it dripped quickly into a slick path aiming right into his hole.
Something weird started happening: his cock seemed to swell more as the stroking on it became more frenzied. It ached - burned, really - but he kind of liked it. His legs slipped wider apart, as he let out a grunt as the larger werewolf slammed another time into his rear.
"Ready, boy?" the werewolf rasped, tired and horny.
He barely had time to grunt with consent before the tight grip around his cock squeezed further, giving one slow thrust. He yelped, shocked as a huge bulge forced its way through his raw hole, which clamped around it, trapping the werewolf inside him. The same thing then happened to him, only his clamped jaws keeping him from howling loud enough to draw attention down on top of them, as the base of his cock popped out of his sheath, swelling in the werewolf's fist.
For moments he could barely breathe. Semen flowed out of him like a fountain as he kept his jaws clamped shut. More of the fluid poured into his guts, sloshing about under the weakening thrusts from the werewolf. Euphoria took over his head as he panted for air as his load gushed out onto the streets before.
"Wild, huh?" the werewolf panted. "Well, we're going ta be here a while, kid."
He quite believed it. "Th-then want," he panted.
"We go back ta my place," the werewolf promised, "for round two."