"Do you know what this is, Jack?"

It was getting late, and the sun was little more than a sliver of simmering heat over the horizon, beating the last of its mid-summer heat across the lush lawns of the college campus. Annie Tillweather stood in the opening to Jack's room, holding a tiny item aloft between two fingers. Slowly, the young man glanced over at her and shrugged.

"I dunno-- looks like an SD card from here. Or a SIM card? Something like that."

"This," crowed Annie, and walked in to strike a fierce pose in the middle of his cramped dorm room, "is a copy of your browser history going six months back. This is proof that you are an incorrigible pervert who should never have been accepted into this university, let alone be let out among the general public. This, Jack, is your one-way ticket to getting expelled and shamed for life. What do you think of that?!"

Jack glanced up at the tall girl, whose pale face and slightly-too-large teeth gave her the impression of a feverish horse when she was smirking as she did now. It was a pity, really, because she had a nice body, and thanks to her being the president of the runner's club, she had an ass that was out of this world. Of course, she was also an incarnate over-achiever, and had a bad tendency to throw fits over any grade that was less than perfect. This put her sharply at odds with Jack, whose lackadaisical slacker nature had put him instantly on the top of her shit-list. The feud had subsequently been very one-sided, but it had lasted for close to two years now, and today, it seemed that Annie was intent on ending it once and for all. Jack spun around in his chair and leaned back with a neutral expression.

"Okay. And how did you manage to lift my browser history, exactly? I don't recall letting you near my computer at any point."

"I have my ways..!" The lanky girl smirked and wagged the chip in Jack's face. "And you really ought to be kissing my boots and begging me to have mercy, unless you want to be expelled and have to take the walk of shame back to whatever hick town you're from!"

Jack crossed his arms. "I'm from Chicago. But sure, okay; would you mind not spreading my private data anywhere? I mean, I guess you aren't going to, or you would have done it already, not to mention that it would be illegal, but..."

"Pfah!" Annie scoffed at his disinterested demeanor and sauntered over to sit on the edge of his bed, giving him a look of pure pity, as if he were a dog who couldn't understand how it was unable to catch its own tail. "What are you going to do, sue me? We both know who people will stand by; between the good student, who is an asset to the college and the community at large, and the isolated slacker with a hentai fetish? Please! Besides, whatever the case you are still going to be forced to drop out and move back into your parents basement, or wherever-- that is, unless you get down on your knees and beg me like a good boy to spare you that indignity."

For a long moment, Jack stared at her. Then he licked his lips, shrugged and gestured aimlessly with his hands. "Alright," he said. "Fine. What do you want from me? You already know I don't have money... and it's not like you'd trust me to do your assignments for you. So, what?"

Annie grinned like a wolf. It wasn't the complete surrender she had hoped for, but it was a start. Elegantly, she crossed her legs and played the SD card between her fingers.

"I want you to..." She looked as if she was trying to think of the most degrading thing she could, something that he would find totally and utterly humiliating. Something that no self-respecting man would do, a submissive chore to break his resistance to her. Slowly, her grin widened. "I want you to lick my asshole."

Jack stared at her. "Really?"

Annie nodded triumphantly, and held up the SD card pointedly to remind him of her leverage. Jack continued to stare, incredulously."

"Seriously? That's it?"

Annie blinked. "Wh-- what? That's not a small ask! That's, like... totally humiliating!"

Jack shook his head and laughed incredulously. "Are you kidding me? Jesus Christ, girl, if that's what you wanted, all you had to do was ask! No need for this cloak-and-dagger bullshit!"

He rose, but so did she, and stared him down with a cold fury. "No," she exclaimed, and he sensed her frustration as she advanced on him, SD card held up like a weapon to rub it in his face. "No! This, Jack, is my bargaining chip, and that means that you have to do what I say, or-- or it's simply not fair!"

Forced backwards, he dropped back into his chair and stared up at Annie with a curious expression on his face. He made to say something, but then decided against it, and instead adopted a mildly shameful expression, which seemed to mollify Annie slightly. Her skirt swayed slightly as she towered over him, chest rising and falling with her irate excitement, and then she turned and marched over to the door, which she shut and locked with a few decisive movements. All the while, Jack allowed his gaze to creep down to her waist and that picture-perfect backside, and only now did he notice that what he had taken to be tights beneath her skirt were actually thigh-high socks, and he caught the slightest glimpse of deliciously tanned skin before Annie turned back to him and fixed him with a assertive glare.

"You are going to shut up now. And then you are going to do what I say, and you are going to feel humiliated by it. Got it? Or this--" she brandished the SD card menacingly, "gets passed around to every fucking person on campus. So which will it be?"

Jack waited for what he felt was an appropriately long pause, and then nodded as if the decision was gut-wrenchingly difficult. Then he glanced at the bed. "So, uh.. how d'you--"

"Shut up," she spat, and stomped over to the bed. With a last, harsh glance at him, she knelt down on the edge of it and got on all fours, sticking out her ass at him in an indignant manner as if he had somehow greatly offended her. Jack hesitated slightly, and then got up and walked over to her, tentatively kneeling down and placing himself between her spread legs. It was a bizarre turn of events, but then, things always seemed to veer into the bizarre whenever Annie got involved. Something about her particular blend of mania, assertiveness and crippling self-doubt just made her a magnet for strange shenanigans... or possibly a catalyst. Jack shrugged to himself. Potato-potato; here he was, and here she was, and the offer - or rather, the demand - of giving the girl's perky backside a decisive tongue-lashing was not at all abhorrent to him. Even if he had to pretend that it was humiliating. Whatever got her off, he figured. Certainly, he was already throbbing painfully against the confines of his jeans, and the sight of her round ass underneath that skirt only made the pulse-beat in his cock all the more pressing.

Slowly, Jack placed his hands against Annie's thick thighs and let the fingers run up until he found the edges of her socks, savoring the heat of her skin beneath the soft cotton fabric. He lingered momentarily against the subtle bulge of skin against the hem of her socks, glorying in the sensation of her body beneath his fingers, and then he flipped up her skirt and unveiled her ass, the firm cheeks perfectly round and gloriously naked mere inches from his face. For a split-second, Jack paused to process the fact that she had come to him with this hare-brained scheme and no underwear, evidently expecting him to be much more easily cowed than he really was... but the thought quickly faded, replaced by the gleeful sensation of cupping her cheeks in his hands, parting them with his thumbs and leaning forward to bury his face against her pinkish-brown pucker.

If Annie had expected him to hold back, she was sorely disappointed. Squishing his face between her taut cheeks, he darted out his tongue and immediately found the wrinkled knot of muscle, which he began to slather with his spit as he ground the tip of his tongue in tight circles against it. As he worked, a huge grin began to spread across his face, and his tongue began to drill harder and more insistently against her opening as he explored her; it was evident that she had showered not ten minutes before showing up at his door, and the taste of her fresh asshole told him everything he needed to know. With his fingers groping and massaging her cheeks, Jack forced his lips up to her pucker and wiggled the first half inch of his tongue into her, which drew a gasping moan from the tall girl's throat. Then, with a wet slurp, he withdrew and placed a hard spank across her right cheek.

"Jesus fuck, girl!" His voice was chipper, but each word held a tinge of lustful teasing that he was certain would grate on her. "You have a great ass! If I'd've known that all you needed to calm down was someone to tongue-fuck your asshole--"

Annie swatted a hand half-heartedly back at him, but missed. She mewled softly. "Sh-- shut up! And keep going..!"

Jack grinned, placed another teasing slap across her ass and then dove back in, his tongue swirling thick spit against her balloon knot before wiggling against the muscle like a worm trying to bury itself back into the earth. Gradually, he began to alternate his motions, switching from the hard, drilling tip to a slow and languid drag of the flat of his tongue across the hole, giving every inch of her smooth, athletic ass a luscious tongue-bath. When he once again came back up for air, he leaned in and dug his teeth gently into her taut cheek, feeling the sweltering heat where he had spanked her, before planting a kiss on the flawless skin and reaching in to stroke a thumb against her spit-glazed asshole.

"Boy, I sure am humiliated by this..!" Jack could barely contain his own laughter as he gently rubbed his digit against Annie's hole and felt her squirm beneath his touch. Surreptitiously, he reached down with his other hand and began to undo his pants. "To think that you would force me to do something like this, completely against my will! Oh, the humanity!"

Pulling down his pants, Jack grabbed a firm hold of his painfully hard cock and began to pump it slowly with his right hand, while his left thumb slowly pressed into Annie's hole, causing an errant moan to disrupt whatever scathing retort she was about to throw his way. Before she could recover, Jack withdrew his thumb and spread her ass to allow his tongue to resume its attack on her puckered sin-hole, and to his satisfaction, the next sound from her lips was another moan, and then another. Swirling his tongue and lapping at the haughty girl's emergency exit, Jack stroked himself slowly and gave a soft, lowing moan of unadulterated pleasure.

"I guess I always figured you were a freak," Jack murmured, face buried between Annie's cheeks. He dragged his tongue across her knot again and grinned at her moaning response. "I just hadn't guessed it would be this..."

He wiggled the tip of his tongue against her hole and dragged a trail of spit across the tight sphincter. At her insistent wiggle, he did it again, and listened to the deep, breathy moans coming from the other side of the bed. Gingerly, Jack let go of Annie's ass and shifted his left hand down to find her clit, keeping his tongue drawing tight circles against her back door while smoothly sliding his thumb across the tiny, slick nub at the crown of her sex. The reaction was immediate, and as he began to slowly match the movements of his tongue on her clit, Jack stroked himself to the sounds that she was making, each gasp and moan another piece of fuel for the fire of his lust. Idly, he considered standing up, pushing her forward and sliding inside her, but her perfect peach ass around his nose and mouth was too good of a treat to give up on, and a small part of him figured that this might not be his last time doing this, so long as he played it right this time. So, he simply settled in to rub her clit and the inner lips of her cunt with his thumb, while his tongue wiggled and pushed against her second hole with dogged determination. And for every moan he coaxed from her lips, he felt a throbbing surge of pride and pleasure course through his cock, its tip leaking pre-cum at a rate that heralded an imminent eruption. Jack moaned, face-deep between Annie's cheeks, and ground his thumb against her pussy as fast as he could. It was not skillful, but right now, it was all he could muster.

And it was enough. With a sudden gasp, Annie's entire body rose in an arc and bucked against him as she cried out an orgasm, her runner's body trembling beneath his touch as she climaxed against him. Over and over, her hips jerked and seized , and each movement served to grind her harder against Jack's thumb, until she finally fell silent and collapsed, her upper body going slack while her ass remained thrust senselessly into the air. Gently, Jack drew a tiny circle against Annie's clit, and felt her cheeks flex and tighten against his face, and with a grin, he gave her asshole a final peck before withdrawing and slowly getting to his feet. His knees were sore, and his cock ached in his hand as he stood over Annie's prone form, her ass glistening and trembling like a winking treasure-trove of pleasure. The sight was too much. In seconds, with his hand stroking rhythmically over his engorged shaft, Jack felt the burning pleasure of release surge up through him, and he barely had time to reach down and steady himself against Annie's ass before he unleashed a torrent of warm, creamy cum all over her. With a groan that approached pain, Jack painted his rival's cheeks and the canyon between them with every drop of spunk left in him, and in the aftermath, he gazed down and watched the tiny, spit-shined pucker now flooded with hot cream, sopping and running in thick drops down across her inner thighs. With a sigh, Jack teased the last few drops of cum from his cock, and then waddled over to fetch a towel from his threadbare closed. He cleaned himself, and then handed it to Annie, whose face had turned to follow him, oddly quiet for her normal behavior.

For the next few minutes, both of them were silent. Jack had gone back to his chair, his pants pulled up but still unbuttoned. Annie had wiped off the deluge of cum from between her cheeks, and now sat on the edge of his bed, a faint blush painting her face a vivid pink. For the first time, Jack felt a curious attraction to her. Not that her body had never inspired sensation in him, but something about her post-sex shame sent a soft warmth through his chest. She looked.. cute, despite herself, and as he looked at her, Jack imagined bending down and kissing her. No doubt she would resist, considering where his lips had just been, but the thought was not wholly off-putting. The revelation was slightly surprising to Jack. He cleared his throat.

"Hey.. are you okay?"

Annie jerked upright, and nodded mechanically. "Yes," she spat, without thinking. "Of course. Why wouln't I be?"

Jack shrugged. "Well, I mean... what we just did--"

"Is a secret." Annie shot him a piercing gaze. "Got it? This. Never. Happened."

Jack blinked, slightly taken aback. "Uh.. sure. Okay. I just.. I mean, it seemed like you enjoyed it, is all."

She looked away, her blush flaring into an intense scarlet. "Ah.. You wish..!"

"Oh, come on." Jack frowned. "It's okay.. I'm not judging you for it, you know? Fuck, I think it's hot as hell that you like having your ass eaten!"

"Sh-shut up!" Annie flailed a hand in his direction. "People are gonna hear--"

"Oh? Hear what?" Jack grinned. "That you like it when I lick your butt? That you enjoy it when I tongue-punch your fart-box?"

Annie jumped off the bed and thrust the SD card in Jack's face. "I swear to God, Jack..!"

He held up his hands and grinned disarmingly. "Relax, Ann! I promise I won't tell anyone..." He paused, and then raised his voice to a half-yell, "...that you enjoy it when I lick your shitter like an apple fritter!"

Mortified, the tall girl stalked over to the door and began to fumble with the lock. Jack followed her, giggling as he continued to tease her mercilessly:

"What's the matter? Nothing wrong with that; loads of girls love it when you give their turd-cutter a tongue bath! Just because that's what gets you off, doesn't mean I don't still respect you! Annie the Butt Slut. Who knew? But believe me, if anything it only makes me like you more. Somehow, you are a lot more relatable when you are letting me have a double scoop of that chocolate sundae--"

Suddenly, Annie turned around and pushed him up against the wall, and he could only grin amusedly as she got up in his face and stared him down, her large, solemn eyes daring him to say another word. She spoke quietly, but every word was punctuated by an unwavering intensity.

"Jack. Shut. Up!"

He obeyed her. For a long moment, they stared into each other's eyes. Then she let go of him, and put her hand on the door knob. She had finally managed to undo the lock, and Jack watched her prepare to leave with a mix of relief and disappointment. As her wrist twisted to open the door, she glanced at him, and the merest hint of a smile flickered across her lips.

"This isn't over," she murmured, and her brow cocked as she held up the SD card in front of his face. "Not as long as I have this. Blackmail, remember? So crow all you want. Just as long as you remember who's in charge."

Annie's face split in an impish smirk, and without warning, she reached in and planted a firm kiss on Jack's lips. Then she pushed out into the hallway, and Jack watched her stride away with a strange, churning sensation in his stomach, his gaze on her thigh-high socks and the perky butt beneath the skirt, which swayed tantalizingly with every stride. Desperately, he leaned out the door and called after her:

"There's not even anything on that damn card, is there?!"

But she was gone. Jack leaned against the door jamb with a faint smile on his lips, unsure of what or how to feel except confused. Slowly, he went back into his room, shut the door, and sat down on the bed. For a while, he simply sat there, a small, goofy smile adorning his face.

"Shit," he finally said. "I think I'm in love with her."