Work Text:
Her asshole was opening up beautifully for him. He was two fingers deep, stroking hard over the girl’s velvet walls as she shook around him.
A blue plaid skirt was pushed up slim hips, white lace panties framing a pale, heart shaped ass, and her flushed pink anus was dripping with lube as he finger fucked the young girl.
James had had an eye on Ava for months. She was the kind of girl who hated to fail, and was cursed with anxiety and a nearly unflinching need to please her superiors. All he had to do was find excuses to keep her grade at a ‘B’ and the girl almost quite literally came begging for an opportunity to improve her scores. She barely resisted as he stripped her of her blazer, shirt and bra, only trembling faintly with tightly shut eyes as he cupped her breasts in his hands and ran calloused thumbs over puffy pink nipples.
She was only fourteen, but her ass was plump and her breasts were full, and her pouty pink lips, flawless ivory skin, and long strawberry blonde hair made her irresistible.
She hadn’t fought him as he bent her over his desk, pressing his clothed erection into the crack of her ass, his rather large stomach hanging over her lower back. The only moment of resistance so far had been after he had pushed up her skirt and pulled down her underwear, when he slicked up his fingers with the lube he had hidden in his desk, and swept cold, wet fingers over the pucker of her asshole.
Ava had jerked forward, hitting the desk with a dull thumping sound, a whine caught in her throat as she protested, “Please, Mr. Jackson, not there.”
He had paused, fingers pressing lightly into the ring of muscles. The girl shivered hard, her hole contracting against the pressure. “Do you want your “A” or not?”
She had started to cry at that point, but hadn’t put up a fight when he pet over her hole again, waiting for the muscle to soften up before he pushed a long, thick finger into her body.
Even now, there were small whines and cries that she tried to hide in her folded arms, and she was pressed tight against the desk, trying her hardest to get away from him, but she was allowing the slow and steady thrusts of his fingers into her hole.
He was going to hell for this. Here he was, a nearly fifty year old teacher anal fingering his fourteen year old student. But he didn’t care. It was so fucking hot. He was balding, with thick rimmed glasses and a large beer gut, a direct contrast to the gorgeous young girl shaking underneath him.
James withdrew his fingers with a squelch of lube, grabbing the tube and pouring more, over three digits this time. Swirling the rough pads over the tender puckered muscle, he slotted all three into the panting girl in one smooth thrust.
Ava let out a squeal, her hips bucking as her body tried to pull away from the stretch. She looked back at him, green eyes full of tears. “It hurts!”
Running his free hand over her flank, trying to calm the panting girl, he replied, “It’s going to hurt a little. You’re not used to having something up there.” He gave a rough thrust followed by a pressured stroke against her front wall, smirking when the girl gasped and subtly pushed back against his hand. “You’ll grow to like it soon enough.”
He drizzled more lube over his fingers, fucking them back into her with a loud wet sucking sound. Ava seemed embarrassed by her sloppy ass, attempting to hide her red face in the curtain of her hair.
Withdrawing his fingers, James unbuckled and unzipped his pants, pulling out his large dick. It was the one part about him he was proud of. He might not have much in the looks department, but his dick was huge. Too bad Ava was too small to appreciate it. His shaft dwarfed her bottom, and he wondered if he would cause tearing.
Slathering himself in more lube, half the bottle gone, he lined himself up with the red ring of her anus. He held the girl’s hips still as the head of his cock pushed just inside her. Almost immediately he had to pin her to the desk as she started to scream. One hand left her hip as he slammed a hand over her mouth, her tongue slicking uselessly over his palm as he steadily pushed further up the young girl’s bottom.
It was a long way to go, her rectum fluttering around him, her heartbeat surrounding his dick as he pushed inside the blood hot heat of her. Looking down, he tried not to come too early at the sight of her anus stretched too wide around him. He didn’t see any blood, but took his remaining hand off her hip to trace around the slick stretch of her. Ava had collapsed in shock against the desk, and only twitched as he pet at her asshole.
His hand came up to fist in her hair, his dick buried halfway up her ass, several inches left to go. He pulled back on her, lifting her upper body off the desk, her whine of protest buried in his palm. James leaned forward to whisper in her ear, “If I take my hand away, do you promise not to scream?”
She nodded, tears and mascara running down her face.
“Good girl.” He took his hand away, planted his feet, and shoved the rest of himself up into the fourteen year old’s asshole. He didn’t stop until the very root of him was pressed up against her anus, his public hair scratching between them, his stomach coming to rest on her ass.
Ava’s mouth opened in a silent scream, her eyes wide in her pale face, breath coming shallow and panicked.
He didn’t give her time to adjust, pulling back until only the head of his cock was still lodged in her, then slamming back in, sending her crashing back into the desk. The girl bit back a high pitched squeal, her legs kicking out and feet scrabbling on the floor. Her back arched from the pain.
James groaned, not slowing as he stroked through her hair and down her back. “Tell me how much you like it. Tell me how much it hurts.”
Ava’s voice was shaky and breathless, “It hurts so bad, it’s too big!” She turned to look at him, her voice an embarrassed whisper, “I feel like I’m going to have an accident.”
James leaned forward to pet over her cheek. Ava leaned into the touch, desperate for any sort of comfort to distract from the pain running through her. “You’re not going to, you’re just not used to having something going in instead of out.” He punctuated his words with a rough thrust, the head of his dick scraping against a sweet spot. Ava gasped, her eyelashes fluttering as she unconsciously pushed back into the movement.
James paused, then slowly pulled his cock out with a small whine from the girl below him. Her asshole didn’t close, contracting around nothing, her rectum bright red and her anus puffy and inflamed.
“Get up.”
He had her strip off her skirt and panties, but keep the small black heels. Getting down on the floor, he leaned back against the wall, patting his lap and gesturing to his hard dick. “Sit on it.”
Ava blushed hard, refusing to meet his eyes as she settled in his lap, looking at the wall behind his shoulder as he positioned her and helped her ease down. She flinched and winced the whole way, but James watched her pussy glisten and start to drip down her thighs, her asshole contract around his shaft as he reached up to tweak at her puffy nipples.
She gasped when she reached the root of him, her hands coming to rest on his shoulders as her thighs shook around his waist. James met her eyes, settled his hands on her hips, and started to move her up and down.
Her breath whistled through her clenched teeth as her asshole clung to his dick on the outstroke, and James got a slight thrill that she felt like she was shitting herself, and from the way her eyes were starting to roll back into her head, she was starting to like the feeling.
Soon she was lifting herself up, savoring the slick withdrawal, and gasping on the downstroke as she slammed her asshole onto his cock. She was gasping and whining, pushing into his hands as he played with her tits.
He pulled her into his with a gasp, her flat, heaving stomach resting against his beer gut, “You like this.”
Her eyes were glazed over, mouth open and lips bitten red as she looked at him. There was a pause, and then she nodded.
“Is it that full, thick feeling inside you, like you’re going to shit yourself, the fact that you’re getting fucked in the asshole by your old teacher, or both?”
Ava moaned, her hips stuttering against his, lifting herself back off and pushing herself back down with a wet squelch as her asshole opened up for him. “Both.”
Her eyelashes fluttered as he reached down to trace over the stretch of her with one hand, the other finding her clit and pushing down hard.
“Oh god, Mr. Jackson-“ Ava bit her lip, took him to the root, and came. She spawned around him, her legs kicking out and her hands catching at his shirt.
His hands went back to her hips, and he pulled her up and slammed her back down on his dick as she whined above him. It took less than a dozen thrusts before he came inside her, the white fluid immediately slicking the way as he pulled out of her with a small popping sound.
Her hand went right to her fucked out asshole as she leaned back against his thighs, her anus cherry red and puffy, leaking his come down her asscheeks.
James stroked over the girl’s still twitching thighs. “Well, I think that earned you a ‘B+’.”
Ava looked up at him, her eyes questioning. “That’s it? After all this?”
He smirked at her. “If you want an ‘A’,” he reached up and slotted two fingers up into her sore asshole, Ava sitting down on his hand with a sharp inhale, “You’ll have to earn it.”
Ava closed her eyes, took his wrist in her hand, and shoved him deeper.