Rough times in the alley

Story by Fluffy Daemon on SoFurry

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Bad things happen to everyone.

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It was a cold, dark night in autumn...

Fluffy Daemon stood with his back against the alley wall, his paws in his pockets, in an almost casual way, barely visible in the unlit passage, with his black coat, a brown T-shirt visible through the middle part of the jacket that was open, and black jeans. The demon fox could see well in the dark with his dashing, purple eyes though, he was a creature of the night after all.

Not a single sound, not even the wind, was heard, apart from soft hindpaw steps coming his way.

Fluffy's ears perked up, although he retained his semi-casual demeanor while closely listening to the approaching person in the alleyway.

After a few more seconds passed, the other came into his sight, it looked like a young, slender, male dragon, not any older than eighteen.

As the dragon got closer and closer, the demonic vulpine could discern more of his features.

The dragon was a few inches shorter than him, and just smaller and sleeker in general, no prominent muscle mass visible, with the clothing looking baggy. A green coat with a red T-shirt underneath, blue jeans, and paws in the pockets as well.

The dragon's eyes were turned to the ground as he walked on.

Easy catch... the demon fox thought to himself with a smile. "Hey, what are you doing on the street, so late at night?" Fluffy, still in the same stance, asked the dragon, now only a few feet away. No malicious intent was hearable in his voice.

The slender dragon looked up, his light purple eyes now meeting the demon fox' "I-I'm just getting some food at the nearby gas station." he said with a light stutter.

Getting food, at a gas station, this late? Quite curious, Fluffy thought, but well, it meant the dragon had more money in his wallet. The red vulpine gripped the switchblade in his right pocket with his right paw, the dragon was now within striking range.

With an agile move, the demon fox was right behind the small dragon, holding the folded out knife directly against the little dragon's bare throat, putting some pressure on it, but not hard enough to cut through the scales.

"What's your name?" the demonic vulpine asked in a neutral tone.

"A-ah, L-Leon, p-plea-please don't hurt me." the dragon quickly stammered out.

"Leon." Fluffy slowly said.

"Get on all fours on the ground, slowly." the demon fox commanded.

Leon softly whimpered as he did as told.

"Good boy." the red vulpine said in a neutral tone, now on top of the small dragon, still holding the blade against Leon's throat. With his left paw he searched through the dragon's trouser pockets, left first; only some keys, probably of the dragon's house, nothing that really looked useful. Then he tried the right one, he grabbed onto something leathery, and fished it out; a wallet, yes.

Fluffy opened the wallet, finding €50,- in five bills of €10,- each, along with an ID card with the dragon's picture, probably when he was still 16 judging from the even younger look, and a credit card.

"Let me go, please." Leon pathetically whimpered.

Hmm... Not very much physical money, barely enough to live for a week, the demon fox thought to himself, ignoring the dragon's pleas for now as he grabbed both the €50,- and the credit card, and stuffed them in his own left pocket.

Let's hope the credit card contains a decent amount, Fluffy continued thinking to himself.

"What's your PIN code, little dragon?" the demon fox curiously asked.

"...4769" Leon said after a short silence. The dragon started softly struggling to get free.

"Hold still, bitch." Fluffy said quite harshly, putting the knife tighter against Leon's throat, making him let out a soft, pleading yelp and hold still once again.

The dragon didn't really look rich, but there was no harm (no harm for me), to search a bit further, the red vulpine continued his train of thought. He put the wallet down on the ground and searched further in the dragon's right pocket; a black cellphone, the kind that could be folded.

He could probably sell it for some money... But it was too risky.

With a hard smack, the cellphone ricocheted off the alley wall, partially broken, making the dragon under him let out another pathetic yelp.

"I-I don't have anything else, please, let me go." the little dragon pleaded again.

Fluffy sighed and continued, ignoring the dragon again, the right pocket was empty now. He tried both back pockets, earning another yelp from the dragon as his white furred paw slid in the left rump pocket of Leon's pants, and then the right, both empty.

The demon fox decided to move on to Leon's jacket, thinking something of value might be in the pockets there. He first checked all the outer pockets, then reached around and did the inner pockets, touching the dragon's quivering, slender chest all over in the process. Nothing there either. He could see the small dragon wasn't wearing any jewelry or a watch either. A bit of a disappointment, Fluffy thought.

Because of all the movement with his left paw, the baggy coat and T-shirt of the dragon had bunched up a bit around his chest, revealing Leon's green scaled midriff, and at the same time revealing that the dragon's baggy pants had slid down a bit from all the pocket rummaging there, the waistband of the lime green boxers sticking out at the top.

The little dragon looked quite hot as far as Fluffy could tell from the exposed scales; why not rob him of something a bit more than just his money?

The demon fox felt a stirring in his loins, his black furred sheath thickening beneath his boxers and jeans. He pushed the dragon's upper clothing further up, Leon's lower back now fully exposed. He felt the green dragon was shivering even more now, although he couldn't tell if it was from fear, cold, or a mix of the two.

Fluffy's foxhood started slowly rising out of his sheath, getting more aroused by the second as he slid down the baggy pants to the dragon's knees with his left paw, still keeping the switchblade pressed against Leon's throat with his right paw at all times.

"W-what are you doing?" Leon asked, sounding scared.

"Undressing you, so I can yiff you." the red vulpine bluntly answered, the full size of his shaft now straining against the front of his boxers and pants.

"What?! No! Please, don't." the small dragon blurted out in shock. The dragon started softly struggling again, despite the blade pressed against his throat.

Fluffy ignored Leon, and pulled down the dragon's boxers as well, causing the little dragon to immediately tuck his tail between his legs.

The demon fox grabbed the base of the dragon's tail with his left paw and roughly yanked it up.

"Hold that tail up unless you want your throat cut open." the demonic vulpine menacingly said.

Leon let out a soft, powerless whimper, and was still again.

"That's better." Fluffy spoke in a neutral tone, before he took a good look at the exposed and vulnerable dragon. Leon's lime green scaled rump looked tender, and definitely yiffable.

"Cute, same color boxers and rump." the demon fox said in an amused tone with a chuckle. Then he looked further, noticing the lime green, marble sized balls, and barely visible, 1.5 inch, lime green sheath, hanging between Leon's legs.

"Wow, you're the smallest dragon I've ever seen." Fluffy continued in an amused and teasing tone.

"I-I'm not small..." the dragon replied defiantly.

"Yes, you are, I've seen felines bigger than you, tiny dragon." the demonic vulpine answered dominantly and teasingly.

Another whimper was heard from the dragon, "I'm just a virgin, just let me go." Leon tried reasoning.

"Oh, that makes it even more fun, although I expected as much." Fluffy said in an amused tone. "Well, just be happy your virginity will be taken by a real man then." the red vulpine dominantly said with a smile as he let go of Leon's tail, unbuttoned and unzipped his own pants and lowered it, along with his dark red boxers, just enough to let his menacing looking, light purple, 7.5 inch foxhood with a tapered tip, and his golfball sized, black furred balls dangle freely in the air.

He removed the knife from Leon's throat, letting it fold back and putting it in his right pocket, before pinning down the dragon with his body, his own legs holding the dragon's legs down, with the same going for his arms, and forcing the little dragon close to the ground with his torso. He didn't want to accidentally shoot out with the blade during climax, so this was a better way to hold the dragon still. The demonic vulpine's big shaft was under the dragon's belly in this position, pressing against Leon's comparatively tiny balls and sheath.

This caused the slender dragon to squirm even more than before, letting out more protesting whimpers.

"Stop that." Fluffy commanded, momentarily letting his left paw wander under the dragon's belly, until he found Leon's scaly, small balls, and painfully squeezed them as a warning.

Leon yelped again, before stopping his struggles.

"Now, spread your legs and raise your rump in the air." the demon fox continued in his commanding tone, unpinning the small dragon for a moment as Leon did as told, before resuming the pin. Good, it looked like he had broken the dragon's fighting spirit, things should be easier from now on. Things didn't always go well for him in the past, but, well, no point in dwelling on that.

Fluffy himself repositioned as well, lining up his throbbing foxhood with Leon's tailhole, the tapered tip already nudging against the pink ring, before pushing forward without much warning. The whimpers coming from the dragon sounded more submissive now, unlike the dominant moan coming from the demon fox as his cock pushed in inch by inch, until his foxhood was fully hilted inside the little dragon.

A few seconds elapsed before he started thrusting at a moderate speed, not being gentle at all with the green dragon under him. The demon fox kept up his thrusting, letting out moans and dominant growls as he claimed Leon's virginity, hitting his prostate hard over and over.

Soon enough the dragon was erect as well, the laughably small, red, 3 inch dragonhood with a tapered tip, bouncing up and down beneath Leon's lime green scaled belly with every smack of the demon fox' hips against his rump, although it still didn't sound like the dragon was enjoying it.

Fluffy sped up the pace, pounding the small dragon even faster now, his big, black furred balls touching the dragon's smaller, lime green scaled ones every time Leon completely bottomed out.

"A-ah, please stop being so rough." the dragon exclaimed.

"I'll be as rough as I want, little dragon." Fluffy dominantly replied with an extra hard thrust.

Leon was silent once more, well, except for the occasional whimper.

Fluffy continued roughly taking the smaller dragon, precum starting to flow from the tapered tip of his vulpine shaft now, making it at least a little bit easier for Leon. The demon fox' knot soon formed at the base of his long shaft and started growing, bumping against the dragon's rump and the base of the dragon's tail, which the slender dragon was still unwillingly holding up, with each deep thrust.

The demon fox started softly panting inbetween his moans and growls, he was getting close to orgasm now, his black furred orbs drawing up to his body, ready to shoot his load, which grew more and more apparent with his knot getting bigger and bigger with every passing second. Until finally, he roughly pushed it in Leon's tight, formerly virgin tailhole, causing the little dragon to let out a loud yelp.

Fluffy quickly jackhammered his shaft inside of the green dragon, before bringing his head down to the right side of Leon's neck, and biting down. He stopped jackhammering, his light purple cock now wildly twitching and pulsing instead, just before copious waves of demon fox seed erupted from the tapered tip of his long shaft, getting shot deep inside of the little dragon.

Leon silently came shortly after, although not quite as much as the demonic vulpine, just a few small spurts on the alley floor below, with barely any distance.

After around a minute had paused, and Fluffy's climax had been reduced to a steady dribble of sticky, white cum, he slowly let go of the dragon's neck, contently murring. He had bit quite hard, although not penetrating the scales, he had left a bite mark with his fangs.

A few moments after that, Leon started letting out sobbing sounds, bowing his head and letting it rest on the ground.

"Awww, what's that? Did I hurt your precious feelings?" the demon fox jestingly asked, hearing the pained and shamed dragon's sobs.

The dragon didn't respond, but just kept on sobbing. It didn't bother the demon fox very much, it was a natural reaction to what had just happened.

"Hey, look at the bright side. You can tell your friends you're not a virgin anymore now." the red vulpine cruelly remarked.

Fluffy's huge knot started shrinking after a few more minutes and more cruel remarks.

He pulled out with a wet 'pop' when the thick bulb was just halfway shrunk yet, making the sobbing dragon let out a whimper. The demon fox pulled his boxers and pants back up, zipping and buttoning his jeans up again.

"Well, it was fun. I might come back for a second round someday." the demon fox whispered right next to Leon's right ear in a dominant and amused tone, before standing up and walking away, leaving the molested, sobbing, little dragon alone in the dark and cold alley.