Alice obeyed, leaving almost sadly her "Yes Daddy?" crop top behind and pulling down her panties. Her skirt was so short that her buttplug was now visible. The shining jewel at its base made her old professor smile. He pulled on her leash to make her stand up and grabbed her asscheek in his firm hand.
Alice squealed a bit, but didn't retort. She had accepted what was to come. She had agreed to Mr. Thompson's contract and to surrender her body to him, she intended to stay true to her word. In all honesty, she was a bit curious to discover what he had in store for her...
"That's a nice little anal plug you got here, Miss Thornwood," said the evil old man. "Did you enjoy wearing it this afternoon? Did you enjoy walking in the street or talking with your classmate Samantha with that thing buried inside you?"
"I... I did, master. It was a very thoughtful gift," she replied, knowing it would please him.
The professor was delighted to hear the teen stripper reply so submissively. He lifted her skirt and seized her fishnet, before ripping it apart unceremoniously. Alice found it too bad to wreck a perfectly good piece of clothing bought only a few hours ago, before she realized that she had also just been bought by Mr. Thompson... And that he was definitely planning on wrecking her too.
"Fuck me... you really have a perfect ass, girl!" he said, while slapping one of her buttcheeks playfully. "I'm so glad I'll get to ruin that hole in a moment."
"M... My ass, sir?" the 19-year-old girl asked, having a hard time gulping down. "You don't want to start with my... You know?"
"With your cunt? All in due time, Miss Thornwood. I know a fair share of boys have visited it, am I wrong? Your ass, on the other hand..."
"What?" she replied, surprised. "How can you know I'm an anal virgin?"
"It wasn't difficult to guess, considering how tight it was when I probed it in the elevator. I want to experience a fresh and unused hole, not one that's been visited by half of Fowland High's football team. How many guys have fucked you anyway, Alice?"
"Three, sir. Only three..." she replied, shyly.
Mr. Thompson slapped her butt again, this time not so playfully, which made the poor blonde cry out in surprise.
"Stop it with this nun nonsense. I know you're as much a whore as my daughter Stacey. You wouldn't want to lie to your Daddy now, would you?"
The overweight teacher spanked her again, like a misbehaving child. Alice squealed, but not out of surprise this time, nor pain. The feeling she had experienced in Aphrodite's private room was back. The obscure pleasure of being disciplined by an older male...
"I promise you sir, it was only three!" the young stripper replied, feebly.
"Bullshit!" Mr. Thompson roared, as he spanked her again. "You show your body on stage for dozens of old pervs, and you accepted to go on a date with your middle-aged high school teacher knowing full well how the night would end. You're a horny little slut desperate for hard cocks, Miss Thornwood, it's clear to see! Be honest with me, how many stupid high schoolers have railed that pussy? Was it fifteen? Twenty? Thirty?"
"Only three, Daddy!" Alice sobbed. "I promise! I promise on my life! And it's already too much, I should've preserved myself for you like a good girl!"
Those final words seemed to calm Mr. Thompson. His smacks on her red butt became softer, before stopping altogether. Then, he slowly caressed her burning skin.
"You're not lying, are you?" he said, pensively. "All those times you pretended to be pure and innocent despite how indecently you strip on stage in Aphrodite or how hungrily you devour my dick when I visit you, it wasn't just an act."
"No, it wasn't, sir..." said the teen blonde, pleadingly. "I keep telling you, I'm not that kind of girl."
"So you're telling me after having only three teenage flings, you're okay submitting to a man your father's age, and let him insult you and fuck you raw for a single cent?" the depraved professor laughed. "On the contrary, Miss Thornwood, you're exactly that kind of girl! I'm just the first one who gets to enjoy it."
He spanked Alice once again and she moaned in a mix of pain and pleasure, but Mr. Thompson didn't care. Now that he had discovered what a bargain he had just made, he was way past the point of caring. The only thing on his mind was the so many sinful ways he intended to defile the almost untouched young body he had bought dirt-cheap.
The 55-year-old man grabbed her and dragged her toward the window. There, he made her stand against the glass, showing her nude body to the whole town.
"How does it feel, Miss Thornwood?" he growled. "How does it feel to be on full display for every single person in this city? To finally show the whole town you're a sex-crazed hussy, not even worth a cent? That you're ready to submit to an old bastard like me and to get all your little holes filled to the brim with my cum?"
The blonde stripper gazed at the city below, to these streets that had seen her grow from birth, blistering with lights and memories, then turned to her former professor. Mr. Thompson's face was deformed by lust and savagery, he looked even uglier than usual.
And, in all conscience, she was about to let that foul and revolting man do whatever he wanted to her...
"It feels like I've finally found my place in this world, Daddy," Alice answered, believing every single word.
He smacked her ass harder than he had ever done before, again and again. The teen blonde didn't move, she didn't flee. She just screamed louder and louder, feeling the excitement overcome her.
Fuck, how good it felt to be put in her place like this! She would've never imagined a good spanking could feel this amazing. When Mr. Thompson finally stopped, he inspected the small jewel that guarded her asshole. Then, without a shred of gentleness, he removed it in one pull, making her squeal pitifully.
"Is that so? Then show it, whore. Show to the whole the city the ass you're about to offer to a man you've always despised."
Without haste, Alice turned her back toward the window. They were on top of a tower, meaning it would be hard for anyone to notice them, but there was still a risk. Yet, she put her bottom against the bay window, shivering with relief once the cold glass came in contact with the burning skin that Mr. Thompson had just been spanking.
She jerked her hips left and right, wondering how the view was, from the other side... How outrageous and sexy it must look, to see her curvy ass and her lady parts glued to the window!
"You really are a deviant, Miss Thornwood," said the professor, bewildered to see his former student act like this. "I can't believe I didn't notice earlier. And it's not like you hadn't caught my eye! You can't fathom how many times I dreamt of fucking you. Every time you entered my class, I watched you wiggle that delicious little ass, thinking of how hard and relentlessly I would pound it, if given the chance. Wanna know why I so often ordered you to come before the whole class to ask you questions you were too dumb to answer? It was to get to admire this fantastic butt up close, and see it tense every time I scolded you."
Alice remembered that her professor interrogated her more often than her peers. It was one of the reasons she hated coming to Mr. Thompson's course, she never knew if she was going to suffer one of his tantrums or be humiliated in front of the whole classroom. She remembered how stupid he made her feel every time he asked her questions, and how long he enjoyed prolonging this ordeal.
And it had been because, all along, her old teacher had a lustful and sadistic fixation on her. That he enjoyed belittling one of his daughter's friends in front of an audience. What a freak!
Yet, this traumatic memory didn't anger Alice, it only made her hornier. It meant Mr. Thompson had taken a fancy to her earlier than she had thought. That he had coveted her when all this was extremely dubious and illegal!
Well, it wasn't anymore. Now that she was 19, no one could prevent them from engaging in this depraved and taboo relationship, and Mr. Thompson was finally about to get what he wanted. Alice felt oddly excited to be this forbidden fruit the older man would get to savor at long last.
"Oh, Daddy, I didn't know," she whispered, while caressing her ass playfully. "If I had, I'd have deliberately gotten detention to let you rail me on your desk after class. Would you have liked to end each work day like that, before getting home to your wife and daughter?"
"Naughty girl. Let's make up for lost time then, shall we?"
The old man lowered his pants and took his penis out. It was rock hard, he had been eagerly waiting for this moment all afternoon.
"See this, Miss Thornwood? It's the cock you've blown for money several times now. But this time, it won't settle for so little. This time, it will penetrate your most intimate areas. Are you glad?"
"Very much, master," she replied, with a warm breath. "I'm glad yours is the first cock that'll get to access my ass."
"Oh, you do?" he laughed. "Prove it, then. Give it a little kiss before it makes your tiny virgin asshole gape wide open..."
The 55-year-old man presented her with his penis. Alice was familiar with its shape at this point, but seeing it from up-close, especially knowing what would follow, made her shiver...
That thing was gross! It was girthy and veiny, its aspect was almost aggressive. And it was reaaally frigging big! The blonde stripper felt her insides contract only from thinking she had put something this repulsive inside her mouth, and that it would soon penetrate an even more intimate part of her body.
That monstruous piece of meat wasn't meant to make love, but to sully and desecrate anything it touched. Which is precisely why the 19-year-old girl felt her pussy melt at this prospect. She wanted to be soiled, to feel stained... And what better way to do so than with that ugly middle-aged man's phallus?
Alice gave his glans a small and chaste kiss, as if she was sharing her first passionate kiss with a lover. God... She couldn't wait to feel it inside!
"Oh, aren't you just the cutest..." joked Mr. Thompson. "I remember seeing you kissing one of your male schoolmates the same way during recess. What was his name again?"
"Nate. We dated for a while," Alice replied, shyly.
"Ah, yes, Nathan Abbott, one of the shool's jocks. You kissed him so passionately, back in the day! How happy I am to see you use those same lips on my dick."
The old man positioned himself behind her and started to slowly insert his penis inside her anus. Even though she had spent most of her afternoon wearing a buttplug, the tip alone was already difficult to take in. It was going to be a difficult process, an excruciating and painstaking one. And Alice planned to enjoy every second of it!
"You're really new to this, it's gonna be a tight fit," grunted Mr. Thompson, as he tried over and over to penetrate her. "But you'll take me whole, won't you Miss Thornwood?"
"O... of course, Daddy," she replied, gritting her teeth. "As you said, it's brand new, you'll have to work it a bit. But I'm glad it's you who'll get to break it in. I want to make you feel good."
"That you will, Miss Thornwood. And very soon..."
The teacher pushed his thick rod again, and Alice felt the tip starting to get in. He smacked her butt a few times to encourage her. The more he went back and forth, the more the teen blonde felt her anus unclench and dilate itself to welcome him. And, oh, how welcome his erect cock was inside her pristine ass!
When the old man's glans finally reached inside her, the rest slid right in. It's as if he had finally forced his way through a castle's gate, the rest was easily conquered afterward.
"Hoooooooooolly shit..." Alice moaned.
"Didn't think your old high school teacher's cock would fit so well in your little butt now, did you?" he laughed.
He pulled his remote control and put it on its maximum speed. The egg Alice had inside her pussy started shacking uncontrollably. It felt like she had two dicks instead of one inside her! Well, Mr. Thompson's already counted as one-and-a-half, to be fair...
Despite her best efforts, it was too much for her to handle. The young stripper was about to fall to her knees, but the fat older man was having none of it. He put his hairy hands around her waist and kept her in place while he moved back and forth in her defenseless butt.
It was a strange feeling to experience anal sex for the first time. One of Alice's ex-boyfriends had asked that of her once, but she had turned him down. It seemed filthy, messy, even painful. But what she had refused to a respectful college student a year ago, she was now willing to accept from a man her father's age who treated her like trash.
And how wrong she had been! The fierce movements in her anus, the unforgiving way the old bastard was drilling as far inside her as his cock could reach… It was heavenly! Only Mr. Thompson was able to make her feel this way.
"Yes, Daddy! Yes, yes, YES!" she cried, feeling more and more fired up. "Fuck my tight asshole, fuck it good!"
"Look at you, Miss Thornwood. Finished high school not two years ago and already taking a middle-aged man's cock up your ass! Kids these days sure grow up fast."
Her boobs were being compressed against the window, on full display if any neighbors turned their heads towards the skyscraper. What would they think if they saw her like this? A gorgeous student-looking girl receiving a severe ass-pummeling from a bald wrinkly sleazebag with a beer belly.
They would think Alice was a whore, that she had been paid to perform such a debasing act. No one would guess she had, in fact, fully agreed to it and was having the time of her life!
"Fuck, you're tight," said Mr. Thompson. "Your asshole needs some training."
The 55-year-old professor suddenly removed his cock, leaving Alice feeling all empty inside. She felt her butthole start to tighten again, and he ticked his tongue with irritation.
"See, that's where the problem is. You have to unclench your anus and be more relaxed, Miss Thornwood, otherwise you're going to make this experience more painful for the both of us."
"I'm sorry, master," she said, panting. "It's my first time doing anal, I don't know what to do."
"You just need the right guiding hand, little girl, and I didn't become a teacher for nothing. Today's class is in session!"
Mr. Thompson suddenly pushed himself back inside her, making her squeal, then got out just as fast. Before her butthole could understand what just happened and close itself, he penetrated her again, and again, and again. Alice felt her body completely lose track of what was happening!
"That's it," the ugly old man groaned. "You may not understand how to do it just yet, but your body is a fast learner. The more I fuck that little ass of yours, the less it resists. It has recognized we are quite compatible, beyond appearances. With a little effort, I'm sure I can make it gape."
"Is... Is that what you want me to do, sir?" the 19-year-old blonde asked submissively, while her nasty teacher played with her ass like a toy. "To make my butt gape for you?"
"More than anything in the world, Miss Thornwood..."
Hearing him say that made Alice feel hotter. The more she interacted with the vile old man, the more she understood she had strange and undisclosed kinks regarding humiliation and rough sex. But, above all, what made her go crazy was the way her stern and authoritative former teacher wanted her.
She was thrilled to know he saw her as the most desirable woman he had ever had the chance to have sex with, especially considering how forbidden their relationship was. That feeling was reason enough for the young blonde to accept to degrade herself even more to please him.
"Then do it," she moaned, biting her lower lip. "Don't hold back and push that fat dick as far and deep inside me as you can. I promise I'll do my best, sir!"
Enchanted by such a kind proposition, the dirty old man penetrated her ass in one stroke. When she felt he was finally completely inside her, down to the frigging hilt, Alice tried to relax her rectum to completely welcome her Daddy inside her.
"Damn, I can feel you moving all around me..." said the grizzled teacher, delighted. "You really are working magic here, little slut!"
"I... I think I can do it!" she mumbled. "Take your cock out, I think I can stay wide for you."
Mr. Thompson slowly took his manhood out, and Alice did her best to stay exactly in the same position, to make her anus believe it was still embracing a cock. The smile on the nasty professor's face indicated the result pleased him.
"Not bad, Miss Thornwood, not bad," he said, appraisingly. "You're a diamond in the rough, it will be very entertaining to train you!"
"Thank you for your kind word, Daddy. And thank you for taking the time to train a silly girl like me, I don't deserve your generosity."
"That, you certainly do not!" he sneered. "I can't believe I'm wasting my Friday night giving free anal lessons to my dumbest student. My good-heartedness will be the end of me. To make it worth my while, I intend to leave your asshole gaping and brimming with cum before dawn. Considering your new line of work as a stripper, I suppose you have no objections, Miss Thornwood?"
Mr. Thompson really enjoyed reminding her of her current occupation. He knew perfectly well Alice had been pushed to such extremes because of her mother's failings, and that she had never prostituted herself. But that was of no relevance to him.
What mattered was rubbing in as much as possible the fact she was a failure, and that he was glad she had ended in her rightful place. After all those years saying she was dense and slow-witted in his class, the middle-aged teacher made sure to remind her she had proven him right. Every single one of his thrusts in the young blonde's ass sounded like an "I told you so!" in her mind.
Selling her body would've felt been less humiliating than what he was subjecting her too. The disgrace and shame was agonizing... And it only added fuel to the fire.
"None whatsoever, master!" Alice moaned, exhilarated. "You were right all along. I've hit rock-bottom, I'm just a cheap stripper who sells her body for trinkets. Give me the pounding I deserve! Make me your bitch!"
Mr. Thompson pulled on her leash, choking her. She put her hand on her neck, panicking. He was out of control, she couldn't breathe at all!
"Making you my bitch?" he scoffed. "But you already are, Alice! I've marked you with my seed several times already, and I can't even count how many liters of my jizz you've happily drank. You even came back for more, it must taste delicious to you."
The young blonde was unable to answer, the collar on her neck prevented her from uttering a sound. But the evil geezer didn't care, he was too focused on fucking her ass. His movements were violent, unrelenting, as if he was trying to break her anus.
"What's happening, slut, cat got your tongue?" Mr. Thompson insisted. "Don't you want to tell me how surprisingly good your high school teacher's cum tastes? So much so that you've been drinking it every two nights for the past month?"
What the hell was wrong with him? Did he not understand that she couldn't reply?
Alice scratched her neck for a gasp of hair, but her efforts were futile. That was it. She was gonna die here! Almost naked in front of a bay window, wearing a whorish mini-skirt and fishnets, and with a 55-year-old man's cock buried deep inside her ass. That's what her life choices had led her to.
The suffocation made every sensations more intense, and her mind went almost blank from the mix of fear and pleasure that overwhelmed her. She had heard of erotic asphyxiation, but she had never guessed it could feel this intense!
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