Anon Experiences Despair

	Anon tugged at his collar irritably; damn shirt must have shrunk in the wash or something. He drummed his fingers on the table, furtively looking around the quiet restaurant. Why was it so dead tonight? Even the waiters were slacking off! He sighed, running a hand across his bald, green head; he knew this blind date crap was going to fail spectacularly. He’d dusted off his nicest suit, picked out the reddest, most official looking tie he could… he’d even polished his dome. And here he was being stood up. Served him right for trusting the other guys, he supposed. He knew better than to trust /a/ and /v/ when it came to women. He gnawed idly at a breadstick and dropped his gaze to the faux-Rolex strapped to his wrist. She was thirty minutes late. If she even was a she; after last time, he wouldn’t put it past his buddies to set him up with yet another neckbeard. Like he didn’t have enough of them in his life. Another cursory glance across the restaurants deceptively fancy art-deco interior reminded him that he had, indeed, come to the right place. Had she skimped out because of how cheap it was? He wasn’t made of money. He sighed and stuffed the remains of the breadstick into his mouth. No way was he going to wait up for some stuck-up, ugly bitch to-

	The door opened, accompanied by a little bell-chime, and in walked the most beautiful woman Anon had ever seen. She was tall, with two plumes of rose-gold hair wafting from either side of her head, tied by a cute bunny and a red and white bow. The leopard-print coat hugged her hourglass figure tightly, causing her ample bosom to almost explode out of a neckline that plunged far beyond what was decent; a fur collar accentuating a long neck of flawless, pale skin decorated by a black lace choker. Her long legs were bare, save for a garter of similar lace to her choker wrapped about her right thigh, with her modesty kept intact by the jacket’s hem barely extending beyond her hips. Her heels clicked as she sauntered over to Anon’s table, chest and hair bouncing in steady unison.

	“Hey.” She said. “Anon, right?” Anon could only nod as his mouth turned dry and beads of sweat began dripping down his forehead. She slowly pulled the rose-tinted sunglasses from her face. Anon almost squeaked as the brilliant blue eyes looked him up and down; a small smile creeping into the corner of her mouth. “The name’s Junko Enoshima; it’s nice to meet you!” She offered him a slender hand with blood-red nails and he shook it immediately.

	The evening was going smoothly. Impossibly so; Anon pinched himself every time Junko looked away from the table. There had to have been a mistake, there was no way someone like him could possibly be on a date with a literal supermodel! She’d even shown him a magazine containing one of her photoshoots; an exceedingly racy one to boot. The images of her posing erotically in that black and white swimsuit were permanently seared into his mind, and made eye-contact almost completely impossible. He wiped his palms on his trousers for the umpteenth time and poorly delivered another joke. Junko giggled and he had to struggle to keep the memetic spaghetti from tumbling out of his pockets. She took another bite of her meal, a faint moan of delight escaping. Anon’s eyes flicked around, looking for a sanctuary but finding none; he was torn between an angelic face with a devilish expression, the deep canyon of her cleavage on full display, or the delicate fingers that slowly drew patterns on the tablecloth. Something smooth and warm brushed up his calf and he started, deep red rising to his featureless cheeks. She bit the end of a breadstick, the faintest hint of tongue curling out from her lip. The only thing separating her from a succubus was the lack of horns.

	“Tonight has been really, really fun.” She said as they finished their desserts. She wiped the last remaining speck of chocolate from her lips and sucked it from her finger, taking just a little longer than necessary.

	“Y-yeah, it’s been great.” Anon stammered. He adjusted his tie and tried to clear the lump in his throat nonchalantly.

	“It’d be shame for the fun to end so soon, right?” She cooed. Leaning forward, she reached out and rubbed his hand with her own; her smile growing alongside his blush.

	“What did you, um, have in mind?” A waft of her perfume brought the lump back to his throat.

	“Oh… Just a silly game to start with.” Junko pulled back, giggling whilst Anon’s heart sank slightly. “If you can guess what I’m wearing under this coat, I’ll give you a little reward.”

	“What… kind of reward?” He asked. She smiled, pressed a finger to her lips and winked. Anon’s heart rose again, alongside something else. “Okay, um…” He swallowed. “A cocktail dress?”

	“Nope.” She said. Slowly she stood, her hand tracing along the edge of the table as she sauntered towards him. “I’ll give you a second chance, since you’re so cute.”

	“A-ah, um…” It was getting hard to think; the strawberry perfume was intoxicating. She was behind him now, her hands gently brushing along his shoulders and down his torso. “A… S-shirt and shorts?” He mumbled, breath catching as he felt her chest press into his back. Her hands were already on his thighs, fingers tracing invisible patterns as they got closer and closer…

	“Sorry… you lose.” She said.

	“Then… what are you wearing…?” Anon replied, trying not to make the mistake of craning his head around. A shiver ran down him as she brought her mouth to his ear; her hair tickling his bald head. She seemed to pull herself closer to him, hands inching just a little further.

	“Nothing.” Junko whispered.

***

	Anon couldn’t remember what happened after that; everything just jumped from that one impossibly arousing word to her pressing him against a wooden door, lips locked with his as they fumbled with locks and handles and light-switches.  He barely registered the interior; clean, peppered with pots and pans and other cooking implements. Flashes of white and rustic wood. A cabinet full of trophies of brass and frosted glass. They found the bedroom through some miracle and slammed the door behind them, alone in the moderately small space. His hands slid up her thighs and under her coat, confirming her story as he freely groped the soft flesh of her plump arse. Somewhere enroute he lost his jacket and shirt, her lips and fingertips dancing across the exposed flesh. His heart pounded in his chest as the two of them threw themselves onto the soft bed; her warm weight pressed tightly against his body. He felt his tie slip from his neck and his hands slowly ascend, shivering as she licked and pecked along his collarbone. Something tightened around his wrists and he flashed a glance upwards.

	“Kinky.” He mouthed, gasping as she flicked her tongue into the hollow of his neck.

	“You haven’t seen anything yet.” She purred, kissing down his torso and sliding off the bed. He whimpered in protest and she giggled back, standing before him and slowly undoing each of the buttons on her coat. She glanced down at the bulge in his pants, biting her lip as another button went. Anon swallowed, twitching in anticipation as the last one was undone and, with a teasingly long pause, she threw open her only garment. His heart stopped in a mixture of amazement and horror: her enormous breasts jiggled as they were finally freed from the tight constriction of the jacket, dark nipples standing proudly against pale skin; her stomach was flat and perfectly toned, the flawless skin of her shapely hips and thighs catching a gentle shine in the dim light; her cock bobbed freely in the air as it grew to its full girth…

	Her what!?

	“Like what you see, Anon?” Junko said, letting the coat drop to the floor. She slipped out of her heels and crawled across the bed, making sure to let her body press and drag along his. “Why don’t we see what we’re working with, hmm?” She cooed. Before he could even begin to form a coherent response, his brain racing to process the genital revelation, she was already tugging away his trousers. The smile on her face turned cruel as he flinched away from her touch; her hands sliding up his naked thighs to grope and rub the bulge in his boxers. She dragged a nail along his stomach, leaving a painful red line and, with a soft giggle, she pulled away his underwear in one swift motion.

	“You really thought you could… could please me with that?” She managed to say through fits of laughter. She dropped back onto her knees, arms hugging her chest as she tried to steady herself. “I’m not even hard and I’m twice as big! I bet if you fucked me I’d still be a virgin!” Anon’s cheeks burnt with shame, her cackling continuing as a tear ran down her cheek, and he tugged at the improvised restraints she’d used his tie for. He shrunk back into the covers as Junko slid suddenly back over him; her cock resting atop and dwarfing his own. It felt so… warm. He could feel it harden as she stroked both cocks with one hand, her thumb brushing along his tip as she kept him rock hard despite his disgust. Fuck, it reached almost up to his navel; his barely went halfway. A bead of pre from her tip was quickly spread across both shafts, the hot stickiness causing Anon’s cock to twitch curiously.

	“Having fun, Anon?” Junko giggled, crawling up the bed. She leant over towards a bedside table, her cock dangling in front of Anon’s face as she rummaged and hummed. God, he could smell the musky pre she’d slathered over it. She shifted her hips and the tip wafted an inch from his mouth. He pursed his lips and turned his head as far away as he could; yelping as she sat back down on his hips. Junko continued to hum as she turned a small bottle of viscous liquid in her hands, grinding her slick cunt against Anon’s shaft. He futilely tried to buck her off him, but she just ground harder. “Careful, loverboy. My sister is very protective of me… what would she think if she found me crying on the floor, with an unknown man standing naked over me?” She sniffled, her voice turning obscenely adorable as she looked down at him with big puppy-dog eyes. The threat settled in very quickly, and Anon ceased his motions.

	“What’s in that bottle…?” He asked tentatively, wincing as her hips ground down just a little harder. He tried to focus on her miraculously perky breasts as they swayed from side to side, failing each time the tip of her cock lightly tapped on his stomach.

	“Just a little something to make things go smoother. For me, of course; I doubt someone your size would ever need it for anything.” She said. Slipping back off his hips she began to squeeze a generous dollop onto her fingers. “Don’t get me wrong; I couldn’t care less about whether or not it hurts for you. In fact, hearing you scream as I push myself inside… your expression turning to one of agony and despair as I ravage your body… Oh, it would feel so wonderfully awful!” Her face twisted into a bizarre mix of orgasmic pleasure and absolute horror as she shook in place, her cock twitching eagerly at the mention of his pain. Who the fuck had set him up with this crazy bitch?

	“But if I don’t do this, then it’ll hurt for me as well. Being big makes it so hard to fit anywhere… not like you’d know, of course.” She continued, switching back to her old self and absentmindedly pressing her fingers against his anus. The cold lubricant forced a surprised yelp from him. “Besides, a short burst of despair is nothing compared to what I have in store for you.” Her finger pressed harder, his hole tightening instinctively. The tip stroked around the ring, slowly teasing him with strange sensations and painful scratches before finally he relented. His legs kicked back and his bucked as the slender digit dove further, rubbing his inner walls and testing him until something stopped him; a new sensation, like his cock was being stroked from the inside. He gasped as it repeated, her digit rubbing and prodding the curious button. He grimaced, trying to push the sensations from his mind as her middle finger joined the index.

	“You’re a sick fucking bitch, you know that?” Anon said.

	“This is what you wanted, isn’t it? To get fucked by a hottie like me?” She shot back, pulling her fingers from him. He tried to ignore the fact he almost missed the sensation. “It’s not like either of us was ever going to be satisfied with your little prick, anyway. I doubt I’d even be able to feel you in me, let alone enjoy fucking you.” Her slick fingers coated themselves in cool lube again, before slowly stroking up and down her monstrously long shaft. Anon blinked, tearing his eyes away from the sight of her tip glistening. He bit his lip as he felt it press against him, his arse clenching. Junko sneered. “Go ahead… the more you tense, the tighter you’ll be.”

	He turned back to her, sharp retort on the tip of his tongue, before he had to bite his lip to hide the pain of her entry. Fuck, it was like his arsehole was burning! She took her time, slowly pumping the first few inches of her cock in and out of his tight hole as he winced and held back whimpers. He could taste blood as his body screamed, the pain forcing his eyes closed. He kicked out and tried to push her from him, but her hands held his hips tight enough to make him acutely aware of how sharp her nails could be. One of said hands moved away, a long finger sliding up his cock as another inch of her descended into him. The fingertip pressed its sharp nail against the underside of his shaft, lightly pinning his cock to his stomach as she forced his hips upwards. He could feel himself twitch under the scarlet nail as her tip rubbed along the secret spot; confused feelings of pain and pleasure warping his thoughts.

	“Ooh, you’re starting to loosen up already! I should have known I wasn’t your first.” Junko said, pushing just a little further. Anon tensed, trying to tighten himself around her or at the very least make her less comfortable. But the thought kept gnawing at his mind; it was getting easier for her. The pain was fading. It was almost starting to feel… good. No, not almost; it was getting harder and harder to deny that every thrust sent shivers up his spine, or forced a sharp gasp from his lungs. His pre-cum was beginning to pool on his stomach, and his hips bucked and tried to slide further down her shaft as she continued to lazily piston away at him. He barely withheld a scream as she slowly dragged four of her talon-esque nails down his torso: beads of blood rising from his rent (?) skin. A sharp metallic tang filled his mouth as he bit harder to hide his whimpers and moans. Junko’s speed increased and she rolled her hips, the tip of her cock pressing harder against his sensitive bulb. Her finger traced up and down the underside of his cock, causing his legs to twitch and buckle.

	“Fuck!” He cried, back arching and hands tugging desperately at his bonds.

	“Aw, is that all it takes to break you? I haven’t even gotten to the really kinky stuff yet.” She replied. “I suppose I shouldn’t have expected much from a limp-dicked wimp like you.” With a sigh and a soft “pop” she pulled herself from him. Before he could protest or question her actions he was already face-down on the bed; ass in the air and wrists hurting slightly from the now twisted bindings. A firm hand pressed his face into the pillow, which he bit as the thick member slid itself back inside him. It was less painful than it had been at the start, but still he quivered and braced. Every time he thought she was done, another inch of cock would slip inside, the fullness becoming almost unbearable. Her heavy chest pressed against his back, her warm weight pinning him to the bed and surrounding him with the smell of sweat and sex. Her claws dug into his shoulder, drawing fresh beads of painful blood. “Mmm… do you feel that?” She purred. “That’s the very last inch sliding into you… what’s it like, being filled to the brim with a real cock?”

	Even if Anon wanted to reply, he couldn’t; the feeling of her hips slowly bouncing against his arse and her body pressing his into the soft sheets rendered him utterly speechless. Her breath tickled his ear as she pumped her cock languidly in and out of his aching hole, the occasional moan drifting past. He twitched and bit harder, clenching uncontrollably with every brush against his prostate or rubbing of his tip against the sheets. Pressure bubbled at the base of his cock as he succumbed. Whimpers turned from pained to needy. Hands tugged his hips upwards and he complied without a second thought, kneeling prostrate before her. The bed creaked beneath them, their tempo increasing. Slender fingers moved from their tight grip on his waist to grasp his head, yanking it backwards and forcing him to scream aloud as the other hand sank its claws into his hips. Anon’s cock bumped against his stomach as Junko’s thrusts turned wild; a sharp smack on his reddened cheeks forcing the occasional yelp. The heat and pressure mounted inside him, begging to be released. He tugged and pulled against his bonds; all thoughts of escape replaced by the need to feel something or someone rub or stroke his throbbing cock. Every other second he was tensing and groaning and trying to throw himself over the edge but something about her rhythm just kept him there. He screwed his eyes shut and tried to break from her vice-like grip. To set his own pace and to take his pleasure from her monstrous organ.

	The grip tightened. Junko’s breath and pace faltered, a shrill laughter mingling with her moaning. Her rhythm reached a roaring crescendo, thrusting her full length inside him. Her hips slammed against his for the last time and she screamed; nails digging into soft flesh as her cock pulsed. Anon could feel the flood of heat fill him, quivering as he teetered on the edge of his own orgasm. Her hips gave a few slow thrusts, pumping out the last few drops of cum. He heard a soft chuckle behind him, and slowly, oh so slowly, her cock withdrew from him. Panicking, he pressed back, whining as hard shaft left him gaping, empty and wholly unsatisfied. The bed jumped half an inch as he viciously yanked at his tie. He turned his head, glaring daggers at Junko as she wiped her cock clean with his shirt.

	“Are you just going to leave me like this?!” He said.

	“Hmm…” She tapped her lips and dragged a nail down his back. “Yep!” Junko licked a drop of red from her vivid nails, her smile turning wholly sadistic. She pulled her coat back over her naked body; her slowly deflating cock leaving a distinct impression through the heavy fabric. He stared in disbelief as she casually set about neatening the loosened locks of hair, humming merrily to herself. “I had a wonderful time, Anon! Let’s do this again, okay?”

	“You… you bitch! I’ll fucking…” Anon pulled again at his seemingly indestructible tie. “They’ll find me, bitch! They know where you live! And when they find this place-“

	“Huh? This place?” Junko said. Her eyes once again widened to sickening cuteness. “But Mister Anon, this isn’t my house.” She made for the door, blowing him a kiss and flicking the lights off with a sadistic giggle as the blood drained from his face. Her silhouette flickered out the door, which closed with a soft thud and shut out the last remaining light. Anon cursed under his breath, buried his face into the pillow and screamed. Sweat and cum dripped down his arse; his cock twitching in a last attempt at orgasm before slowly deflating. He shuddered, grinding against the sweat soaked covers in brief, vain attempts to return himself to hardness. Lines of pain ached across his stomach and back, the occasional hot droplet smearing on his flushed skin. Another shudder wracked him, followed swiftly by another. Before he knew it, he was sobbing; tears tumbling down his generic face and soaking the pillows as the pain, frustration and sheer sense of violation crashed on his mind like waves. And she had loved it. Every goddamn fucking moment of it. Worst of all, she’d made him enjoy it too. Even as he wallowed in his despair the sick truth of his own pleasure haunted his thoughts and broke his resolve, spurring a fresh wave of tears. Slowly the sobs shifted. His face contorted as hysteric laughter shook him, until it resembled the peculiar expression that had dawned on Junko’s face mere minutes before; one of sadistic pleasure and absolute horror. The suffering almost felt… good. Something in his mind snapped back, returning him to tears. And so he lay there. Lay there and sobbed and shivered naked in the cold dark, waiting for some unlucky bastard to free him from hell. He didn’t know how long it would be, but it was more than enough for him to resolve to never, ever take dating advice from his friends.

	His ears pricked up at the sound of voices in the corridor outside. Heavy accents; Cajun, maybe? He had a hard time telling. Anon stopped himself from calling out to them as his brain relayed the worst case scenarios; he needed help, certainly, but what the hell would anyone say to finding a naked man tied to their bed? Would anyone even believe him if he told them what had happened? Who the fuck breaks into a house to bang a stranger anyway? He bit his lip, trying to find some way to make himself hidden, or at least decent, and quickly tried to rehearse a dozen suitable speeches. Before he could act on anything, however, the door opened and the light blinded him. Anon blinked, and soon noticed the portly figure standing in the doorway. He was short, with an enormous croissant shaped pompadour atop his head. He had a rounded face, with ruddy cheeks and a mildly friendly countenance to him. The chef’s eyes widened as he slowly turned to what must have been his own bed. The apron in his hands fell to the floor with a soft thud, and the two stared at one another. That one second felt like eternity. Anon opened his mouth to speak, shaking off the stupor, but the now thoroughly pale chef reacted first; screaming like he’d just seen a ghost.

	“Avril Lavigne!”