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Hannah shivered as she walked down the hallway to the Headmaster's office. She was a horny little slut and she often got in trouble... ever since the very first day that she'd arrived at the all girl's school at the tender age of 18. That day she'd gotten into a fight with a girl who thought she was snobby... and she'd gotten her very first spanking.
It had shocked her how much she'd enjoyed the spanking... it had turned her on, something that the Headmaster had seen almost immediately. By the end of her punishment she'd been moaning and pushing her pink ass out for more... the Headmaster had pulled down her panties and seen her wet pussy. Telling her that she was a dirty slut who needed to learn her lesson, he'd pulled out his dick and taken her virginity then and there, spanking her throughout the entire thing. She'd cum incredibly hard and even played with herself some more as she'd sucked his dick afterwards. The very next day she was back in his office, in trouble again.
Now, at the age of 22, it was her last year there and things had escalated quite a lot over the past four years. She was addicted to her spankings, usually getting into trouble at least once every couple of days... on days when she was particularly horny it was several times a day. The Headmaster and her had become quite accustomed to each other's fetish's... Hannah got her tender ass spanked raw and red, and then he fucked it, spraying his cum inside her ass and on its red cheeks. He preferred anal sex to any other kind of sex, although she'd cried and fought the first time... now she loved it almost as much as she loved being spanked. Regular sex just didn't totally do it for her anymore, she was addicted to her anal pleasures.
Nothing satisfied her quite like that, and she didn't know what she was going to do when she left school... but while she still could she was gonna get it while the getting was good.
Headmaster Charles welcomed her with a stern frown, giving her a lecture on behaving herself that was made totally inept by the huge bulge in the front of his pants. Mostly it just made her even more horny, and she wriggled in her seat, waiting for him to tan her bottom. He kept talking, knowing how much it turned her on to be made to wait, he could see her nipples poking through her shirt in anticipation. However, it wasn't her breasts that he was interested in.
Finally he had her stand next to his desk, bending over to grip the sides of it. Lifting her skirt, he pulled her panties down and off, instructing her to spread her legs. Holding the paddle that he always used, the Headmaster loosened his tie as he stared at her exposed, crinkled asshole.
"Oh God Headmaster," Hannah moaned, "Would you just spank me, PLEASE!"
She shrieked as the heavy wooden paddle came down, squarely smacking her ass.
Hannah began counting out the hard strokes in a broken voice, unable to explain to herself in her head why she was getting so wet from the beating. It hurt horribly, it was humiliating, but her nipples were now hard and rubbing against the desk through her blouse because she was leaning over so far, and her pussy was actually starting to drip down her thighs... even her voice was getting more and more excited with every sharp jolt of pain that wracked her body.
She knew that behind her the Headmaster's bulge was growing as he abused her. They both had some unexplainable desire for this, the beating and the violation... a kind of obsession with her ass. It was growing cherry red, almost glowing as he hit her harder and harder, in a kind of sexual frenzy that gripped them both.
"FIFTY... FIFTY-ONE!" She cried out, sobbing it as she squirmed beneath the hard paddle... oh God she was so close to cumming, and her ass was so sore, it hurt so much...
The Headmaster was panting behind her, looking at her swollen pussy and red ass, her tiny asshole that seemed to be begging for penetration. Hannah was obviously excited, her ass swaying as though begging for more punishment. She wanted it... she loved it.
At sixty, her eyes were practically glazed from the painful pleasure, her closeness to completion.
Headmaster Charles couldn't stand it any longer, not her cracked voice or her reddened cheeks, or the way she thrust her buttocks out for more... scrambling with his pants, he dropped them. Pushing into her vagina just once, he wetted his dick in her sopping juices and then pulled out and shoved into her tight schoolgirl ass.
Rutting her roughly, his hands dug into her tender ass cheeks and she howled at the indignity, writhing beneath him. His groin slapping into her red, swollen ass was another kind of spanking, and as he fucked her harder and harder. The young woman moaned in pleasured pain, her ass cheeks burning and the inside of her ass cramping and spasming. It felt so good, so wonderfully complete to have his swollen dick ravaging her ass.
The Headmaster wasn't paying attention to her pleasure at all, he was just intent on spearing her tender asshole with his lance, his hands roughly squeezing her red buttocks, making her writhe in pain before him. They both knew that the pain only helped her on her way to pleasure. The discomfort and red jolts of hot pain would mingle inside her body, wrapping around a hidden pleasure, her own little dirty secret fetish, and bring her to heights of ecstacy that she couldn't otherwise achieve. As his hands squeezed hard, his dick shoving deep into her rectum, Hannah gasped and humped and started to cum.
Howling and thrashing beneath him, she humped against him in her pleasure, rubbing her ravaged ass against his body as he sodomized her. Headmaster Charles couldn't take much of her slutty ways, or her tight gripping ass, and he grunted as he buried his cock into her tightest hole, feeling it ripple around him and clench hard in her orgasm... He began to fill her ass with his own cum. They howled together in mutual orgasm, her ass clenched so hard around his pulsing dick that they might as well have been attached there.
Panting heavily, Hannah lay on his desk as he collapsed on top of her, eliciting a moan of pain as his body fell onto her poor abused buttocks and his dick lodged itself even more firmly into her ass. A few last spurts of cum twitched inside of her and then everything was still....
The Headmaster pulled out and dismissed her. The young woman left his office with cum dripping out of her violated asshole, ignoring the smirking secretary's expression as she observed Hannah's peculiar walk. She couldn't sit down for the rest of the day... really, that made it a VERY good day.
She was so sore that she wasn't sure she'd be able to make it back the next day... but since this was her last year there was very limited time. Besides, she mused, if she did come back tomorrow, her ass already tender, it would probably just be even better than before...