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Dean's parents had been delighted when Mr Novak had volunteered to tutor him after school - they'd been concerned about his grades for some time now. What they didn't know, and that Dean would never tell them unless he wanted the video recordings of his time with Mr Novak to find their way onto the internet, was that the only tutoring he was getting was in sex education.
He waved goodbye to his father, who dropped him off outside Mr Novak's house three nights a week, before walking up the front path and letting himself in. As soon as he'd shut and locked the door behind him, he stripped off his clothing - including the pair of pink, satin panties Castiel had chosen for him - and made his way upstairs into his teacher's home office.
Mr Novak sat at his desk, quietly marking his students' work. As usual, he didn't look up at Dean's entrance. As he'd been trained to do, Dean knelt in front of him with his head bowed, wrists crossed behind his back, and legs spread. Dean felt exposed like this but, as he waited for his teacher to acknowledge his presence, his cock started to harden at his vulnerability. Holding his arms behind his back for so long, a dull ache grew in his shoulders. But he knelt there in silence, unmoving, only the scritch scratch of Castiel's pen on paper and the rustle of pages telling him that time hadn't stopped.
Finally he heard the pen being laid down and the shuffle of papers as Castiel gathered them into a neat pile.
"Take a seat, Dean."
Crawling over to the smaller desk in the corner - for Dean knew better than to stand - he removed the plug in his ass before lowering himself carefully onto the dildo in the middle of the chair. Without further prep the extra stretch burned, but he'd used enough lube inserting the plug that he could push himself down on it without too much difficulty. The chair had no arms, but had cuffs down the side, keeping his arms straight, that Mr Novak fastened his wrists into. Cuffs on the front chair legs were fastened around his ankles, and finally his teacher fastened one last strap around his neck.
"I thought we'd have a movie night," Mr Novak grinned, and Dean's stomach flipped because nothing good ever came from that look. "Doesn't that sound like fun?"
"Yes, Sir," Dean lied.
A laptop was placed on the desk in front of him, on which his teacher played a video file. On the screen a young male, cock confined in a metal cage and nipples stretched by the weighted clamps hanging from them, knelt over a thick dildo.
It took him a few seconds to realise he was looking at himself.
"You were late."
"Sorry, sir," Dean apologised. "There were roadworks. Dad had to take a detour."
"Rule Two?"
Dean bowed his head. "No excuses."
"You are required to be here on time. If you are not..?"
"I'll be punished," Dean finished quietly.
"So hot," Mr Novak said from behind him, leaning over to squeeze Dean's thighs. "I've jerked off to this every night since I made you do this last week."
The camera tilted up and Dean's face came into view, face flushed as red as the ballgag now between his lips, eyes wet with unshed tears.
The memory was still vivid in his mind, and Dean knew the tears he'd held back in the beginning were nothing compared to the ones he'd been crying by the time Mr Novak was done with him.
As he remembered, it wasn't long before a sharp crack was followed by his agonised wail.
He'd thought the flogger was an incentive to fuck the dildo harder, faster, deeper - and Mr Novak hadn't been eager to dissuade him of that notion.
Dean's thighs burned as he moved up and down, up and down, up and down. His ass had stopped burning by the time the flogger had first landed across his chest, catching the weights and causing fresh pain to erupt through his nipples.
He tried to avoid his prostate with each downwards movement, because the pleasure was cut off by the frustration of not being able to get fully hard.
The flogger landed again, across his back. The pain of the flogger against his skin was mild, merely reddening his skin without leaving marks. The colour would fade within hours. He tried to ignore the way his thighs were turning to jelly and fuck faster, crying out when the flogger was aimed at his chest once again. The pain in his nipples would last much longer.
Again and again and again, the flogger struck him - chest, stomach, back, thighs - until Dean was sniffling and sobbing and didn't think he could fuck any harder.
Dean was humiliated watching himself, hearing his teacher's breathing getting heavier as his hands stroked over Dean's chest, pinching and tugging at his nipples; stroked down his stomach and along his thighs - never touching his cock, that was painfully, embarrassingly hard. Mr Novak was right - the video was hot - because Dean could remember the pleasure and relief he'd experienced when it was all over and was ashamed to admit he wanted to experience again.
Gradually Dean slowed, slouching forward as he fought to find the strength to continue. He screams had been reduced to whimpers as his nipples were now in constant pain.
"You don't look like you want to come," Mr Novak goaded him.
Dean fucked down harder once, twice, three times, before slowing again.
His teacher laughed. "Maybe I won't let you."
Dean forced his head up to look at him, hair damp and sticking to his forehead, eyes wide and green and pleading. "Please," he croaked when his teacher removed the gag. He licked his lips. "Please..."
"'Please' what?"
"Please let me come. Sir."
"Do you think you deserve to come?"
Dean whined. "Yes?" he asked hopefully.
"No."
Dean's head dropped as he continued to halfheartedly fuck the dildo. His teacher's fingers wrapped around the weights and held them.
"Pull them off and I'll let you come."
Dean could see it on his face on the screen as he worked up to pulling them off, and he arched into his teacher's fingers as they pinched his nipples.
"Fu-uck," he sobbed as more pain exploded in his nipples.
"Language," his teacher chided.
Immediately Dean opened his mouth and poked out his tongue, allowing his teacher to pinch a clothespin to it as punishment.
"Good boy. Can you make it to the bed?"
Dean struggled to get to his feet, gone numb with the loss of blood flow as he'd knelt.
He disappeared from view as Mr Novak carried him to the bed and removed the cage, before repositioning the camera so they could get a clear shot of his dick filling Dean's ass.
Mr Novak easily manhandled Dean's legs onto his shoulders. "You took your punishment so well," he praised Dean before pushing into him.
He didn't move - couldn't move - as his teacher pinned him down and pounded his hole, fucking him into the mattress. His limbs were like jelly, his mind floating as pleasure built up inside him. He moaned wantonly, mumbling incoherently.
Occasionally Dean could make out the words 'please' and 'more' and 'thank you, Sir' as he found himself unable to tears his eyes from the screen, wanting to see what it looked like when his teacher came in his ass.
"You're so close," Mr Novak whispered in his ear.
Dean wasn't sure if he was talking about the video or real life, but he agreed anyway. Then fingers were curling along his hard length and jacking him off frantically, and Dean tried to fuck into his teacher's hand as he kept watching, seeing the way his teacher's balls drew up into his body, seeing the stutter of his hips as he filled Dean's ass with his come, seeing the way his thick cock softened and slipped out of him.
Dean blushed at the trickle of white that seeped out of his gaping, twitching hole, then his own hips were stuttering and white coated Mr Novak's fingers.
He licked his teacher's fingers clean without being told when they were held up to his mouth, then kept his mouth open to catch Mr Novak's come as he jerked off in front of his face.
"Thank you, Sir," he said breathlessly.
"Perhaps you'll be sure to be on time to our lessons in the future."
"Yes, Sir," Dean mumbled as his plug was pushed back inside him, trapping his teacher's come.