Frisk Gets Pimped

Frisk had begun to have second thoughts about this whole affair.

He barely remembered how it had happened, but according to Chara’s hidden-camera documentation, the pair of humans had gotten very, very drunk and played poker. The loser would be obligated to be the winner’s servant, no matter how ridiculous or degrading their demands were, for a full week. Of course Frisk had lost, as the game of choice had not been Mahjong, his ancestral pastime, but Texas Holdem, some gwai lo invention made for the sole purpose of stealing victory from foreigners. One day he would have his revenge. However, as a proud descendant of ancient Chinese lineage, Frisk would never back down from this most recent challenge. To do so would insult his ancestors.

But as Chara led Frisk into her room he began to feel pangs of apprehension work their way through his guts like a cold nest of snakes.

There, laid across Chara’s bed in a doll’s accessory set were several articles of his adopted sister’s most ludicrous and lewd clothing articles. Panties in a rainbow arrangement of colors and designs, from logos etched into the front, hearts on the rear, to open-crotched and backside strips of cloth barely constituting underwear. Lacy thongs that hugged tight and concealed nothing at all. Stockings striped and solid and spotted with color, thick sock-like fabric and sheer translusent nylon. Collars of leather and latex, endless circles in a pile that was itself circular. A cornucopia of sexual toys; buttplugs, cockrings, nipple clamps, vibrating eggs, ballgags and more.

Frisk adopted his poker face, but a single petulant droplet of sweat slid down the side of his face regardless.
Chara grinned madly, knowing she’d affected Frisk’s unstoppable DETERMINATION.

“Is the “Hero of the Underground” not up to fulfilling his end of the bet?”

The attack on Frisk’s pride caused a flush of oriental outrage to flow through his being, and he clenched his fists, turning to the mischevious young woman at his side. Chara recoiled at the display, her adoptive brother’s face a mask of pure unbridled DETERMINATION. The same kind he showed through so many trials in the underground. But she didn’t recoil, and instead leaned forward and kissed him lightly on the forehead.

“I know that look, Frisk. That’s why I love your gook ass. Now…”

Her hands slid down and lightly gripped Frisk’s boyish hips, her fingers pinching the fabric of his sweater.

“Git naked.”

And suddenly she yanked Frisk’s sweater over his head, tearing away at his clothes like a demon, stripping him down to his bare ass in seconds, his supple chink skin exposed to the cool air of the room, his hands unconsciously covering his naughty bits.

“Here’s the deal Frisk. You lost that game, with TWO conditions, not just the one in video. I know you gooks love gambling, and I used that to my advantage, getting you not only to do whatever I want tonight, but ALSO you owe me a lot of money.”

She squatted down slav-style and grinned ferociously at Frisk.

“And I’m not gonna let you just use the Dreemurr’s money to pay me off. You’re gonna sweat and toil to pay me off. And these-“

She swung her open hand towards the display of degeneracy on her bed.

“Will be your tools.”

About half an hour later they left the house. Together they’d snuck through the back door down a few blocks to the alley just behind Grillby’s. That’s where they stopped and Chara appraised Frisk. She’d chosen to dress him as scantily as possible, and it clearly affected the former hero, his face flushed bright red from embarrassment and lust. She’d picked out a pair of old dark stilletos for him, and he struggled to stay balanced, his muscles shaking from the stress of it. His legs themselves were covered in pink and black holliday nylon stockings that contrasted his skin beautifully and ended about mid-thigh.  A dark red miniskirt barely covered his ass, and tented slightly from his throbbing erection.  His midrift was completely bare, a sheer pink tank-top cut well above the navel tightly hanging loosely against his chest, his bare shoulders exposed.  His lips were painted a lurid red, his blush almost overwhelming the makeup on his face, the slight purple shade of eyeliner not really helping his slit-like gaze become attractive.

He wore no panties, but adorned a tight cockring around the base of his junk, keeping him hard. A slick of pre was already oozing down his cock and dripping off his exposed scrotum.

“N-now what?”

“Now we wait.”

They didn’t have to wait long. The door opening into their alley swung open and a monster came through. A hulking and muscular wolf-man, bent at the waist to duck through the human-sized door. It was Icewolf, and he bore Underarmor compression shorts that clung to his lower half tightly, leaving absolutely nothing to the imagination, his balls and sheath bulging nicely.

Frisk gulped at the sight of it.

“So here’s the deal Frisk. You owe me a lot of money, and you’re gonna get it back. No monster could resist fucking the Hero of the Underground, and I intend to milk every fuckin’ cent I can from that. Starting with our big friend here.”
Frisk’s gaze locked back to Icewolf’s groin, which had now tented hugely, at least 8 or 9 inches outward, the fabric straining as his hot red cock emerged.  Frisk shuddered, his skirt shifting against his skin as he thought of taking that huge slab of meat. Icewolf stepped forward and spun Frisk like a top and pressed him against the brick alley wall. Suddenly Chara stopped him.

“Whoa there, hold up! You’re not going in dry! Frisk has a long night ahead of him, don’t want him completely ruined this early.”

Frisk’s face was pressed against the cool brick so he didn’t see what she did, but he sure felt that cool slick lube that Chara drizzled out of a small bottle across his rear end. Her hands rubbing the thick slick mass across his bare ass with a lewd schlicking sound, her slick fingers probing his most intimate parts. Suddenly she thrusts two cool slick digits inside of Frisk, forcing a muffled gasp that echoes off the bricks. Her lubed fingers stretched and massaged his insides, the lube spreading across his insides and oozing down to drip off his bare nuts. She inserts a third finger, stretching him wider and Frisk begins to pants as she works him looser and looser, teasing his prostate, circling it with her fingertips until spurts of pre splash from his cock against the bare alley.

“C-Chara I-I’m gonna-“

Immediately she pulled her fingers out of her whore’s hole, leaving it slightly agape and twitching, glistening with lube in the dull alleyway light, Frisk’s breath puffing hot clouds against the cold brick, his heart pounding in his ears. Chara stepped back and patted Icewolf on his massive shoulder and held out a hand. He produced from somewhere a few gold coins and dumped them into her palm and she leaned back against the wall, giving him the go ahead.

Frisk tried to relax as best as he could. This hadn’t been his first time at the anal rodeo, but he was so worked up he was worried he’d cum immediately. He didn’t want to be worn out so early. It would bring dishonor to his ancestors!
So he better braced himself against the wall and took a deep breath, spreading his stance and pushing out his ass. The impending penetration and booty blitzkrieg filled him with DETERMINATION. The huge lupine’s claws grasped his hips and lined up his throbbing cock, the tapered tip prodding at Frisk’s entrance. The human shuddered as inch after hot inch of meat was forced inside him, the going made easier by the lube, but still the sheer girth of it made Frisk pant and squeak like a schoolgirl. Every vein dragged against his most sensitive spots, and the human started to shake as the thick knot pressed against his hole, stopping suddenly, Frisk’s asshole twitching against the hot bulb of flesh.

Then Icewolf drew his cock out all at once, an affectionate growl rumbling from his chest as he drew completely out of Frisk, his poor asshole agape slightly, before plunging back in again, his knot battering against Frisk’s hole. Each thrust rocking Frisk against the brick wall, his legs threatening to give out beneath him, the high-heels not aiding his ruined balance. For what felt like an hour the enormous wolf fucked Frisk against that brick wall, his cock pistoning in and out, squeezing down on the human’s battered prostate, a perpetual stream of pre dribbling onto the cold ground, the thick knot popping in and out of Frisk with little effort.

At last the knot caught, swelling like a balloon inside Frisk, forcing the air from his lungs as spurt after spurt of hot thick LOVE flooded his bowels. Panting, the two of them stood a moment, then Icewolf gripped Frisk by the throat and pulled him against his enormous chest, bending slightly to lap his tongue tenderly against the human’s face as he tugged and shifted his hips. The huge knot shifted inside of Frisk as his client lavished his affections, and the human’s mouth fell open in a silent moan as his cock twitched, rope after rope of spunk spattering against the brick wall. Icewolf gave a contented growl and reached down a huge hand to gently stroke Frisk to completion, kissing him as he made sure every drop was milked out of his human companion.

“Wow you monsters sure are affectionate.”

Chara’s voice snapped Frisk out of his afterglow and back to the cool reality and he tried to steady himself mentally while still tied to Icewolf’s huge groin. A futile attempt to look “business as usual” with a huge cock churning spunk inside him. Icewolf, too, raised a hand and scratched his head in an embarrassed manner at their intimacy. Chara was grinning like an idiot, her previously rosy cheeks scarlet with lust, her eyes lecherous.

“But your time’s up Mr. Wolf. Gotta pull out and move on, Frisk’s got some more work to do.”

Frisk looked back as best he could and indeed a number of monsters were now watching, many of them openly stroking their variety of cocks. Even a few human men and women had emerged from Grillby’s to watch. Icewolf gripped the human’s hips and tugged sharply, forcing a groan of pain and pleasure from the human’s mouth as his knot stretched him to capacity and beyond, popping free in a deluge of spunk. The sudden emptiness dropping Frisk to his knees, panting as his cock bobbed with his heartbeat, trickling a pathetic stream of seed into the growing puddle beneath him, his balls soaking in their mixed spunk.

He heard the clink of coins and got shakily to his feet, kicking off those atrocious shoes.

It was gonna be a long night.