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Dean didn't exactly do it on purpose, really. It's just so hard to look at the nerdy little math teacher with glasses that constantly slide off his nose and his dynamic enthusiasm about calculus and not wonder where all that raw carnal dominance is, and if he can get that part out of him during class. Exhibitionist kink aside, Dean also can't help but want to please Mr. Novak every time he sees him, wants to feel his swift punishment and gratifying praise for everything Dean can do. It would be a lie to say Dean hates being punished, but he also has a yearning to please.
And for that, Dean is laying naked on his teacher's bed set aside solely for sex, cuffed to the bed posts from his wrists and ankles being whipped by Mr. Novak's one and only belt. Dean can tell Castiel isn't using his complete strength; he wants to discipline the petulant boy, but not enough for him to safe word out.
"Tell me, boy, what have you done wrong?" Another provokingly light slap to his ass. "Do you mean today or since our last rodeo?" Dean wanted Castiel more angry, more aggressive. He needed the older man to lose control, like the first time they did this. Three more whips, just as gentle to his lower back and ass. "Don't test me, Mr. Winchester, you've already broken enough rules today alone." More hits becoming slightly more indignant, leaving Dean exhaling relief.
"Well, today I raised my hand in class and called you 'sir' in front of the whole room, then when I went up to the board, I brushed my hand against your hard on, which was likely from me calling you 'sir' without anyone knowing what it really means, or from me bending over to grab the chalk and then -" Dean's guileful words got lost in a combination of a moan and hiss from pain as Castiel let the belt down especially hard. Finally, there's the Mr. Novak only Dean's allowed to see. "Are you intentionally aggravating me, boy?" Castiel's words grumbled in his chest as he walked around the bed, dragging the leather of the belt along the outline of Dean's form. Dean knew he was about to get his way. "I was not aware I was dealing with a brat," a much firmer slap followed, "I'm going to have to use, alternative measures." Dean's never indulged this part of his persona to this degree- always the pleaser; but sometimes breaking the rules (on purpose) is a reprieve. The boy shivered with excitement as the older man fondled the welts on his exquisite ass, reverently tracing the rise and fall of abused skin.
Castiel dropped the belt beside Dean's hip, keeping it within grabbing range. "So, Mr. Winchester wants to play like this; does Mr. Winchester also want the cock ring?" His teacher smiled wickedly, spinning words of nefarious delights. "No sir! Please, sir, no cock ring!" Dean pulled on his restraints, moving his head side to side, looking for his teacher. "That, is not for you to decide, slut. You've been so naughty, and if my bad boy wants to play this way, he must live with the consequences." Without the belt, Castiel allowed his hands to roam over Dean as if he was simply furniture, a part of the room, sometimes being handled too roughly.
With every caress over the swell of the boy's ass, Castiel would raise his hand to strike, causing his student to shiver in anticipation, but instead suck a possessive mark onto the boy's ass. The student would jerk at the surprise every time, but relax into the act as soon as the older man pulled away and continued his ministrations with his hands. Castiel smirked into a blossoming mark and bit the inflamed area softly. The last time Dean was made to wear the cock ring was for masturbating in math class; it wasn't a fun experience, but Dean needed to be punished and Castiel was keeping him in a constant state of denial: he was and wasn't being scolded. The mind games were driving him mad, and all the older man would do is continue to suck and bite marks across the boy's flesh, no longer spanking his pettish student.
Dean squirmed, unable to direct the warm heat of Castiel's mouth anywhere, or reciprocate the touches. Once the teacher was done branding the boy with his mouth, he moved his mouth further down the slit of Dean's ass, licking a trail to the boy's perineum while his agile fingers worked over the tight ring of muscles, never digging in. Gently grazing his teeth over the sensitive area behind the boy's balls, Castiel began biting with increasing vigor, relentlessly pressing his prostate. "You young, petulant, spoiled brat, you can never make up your mind if you want to break all the rules, or if you want to worship them." Dean moaned in foggy confusion from the pleasure while the older man assailed his prostate.
Stepping away from the boy, Castiel grinned at the wreck he'd created; Dean writhed from the loss of contact, wantonly pleading for satisfaction, forgiveness. The older man reached under the (sex) bed for his chest of treasures and pulled out an oval vibrator primarily marketed to women and the infamous cock ring.
"Ok brat, here is your punishment: I'm going to put the cock ring on and use your beautiful ass, if you can answer the question you got wrong on the quiz before I come, I'll let come too. Understand?" Castiel is a devilish bastard, and it only makes the sex better. Dean nodded before asking for permission to speak, "how am I supposed to answer a calculus question without at least a pencil and paper, sir?" The baleful grin on his teacher's face only grew. "You are my brilliant little whore, I'm sure you will figure something out. If not, it's no different to me, I'm still going to come in your ass."
Castiel reached down under his student to secure the cock ring, fingers playing with the purpling cock as he withdrew his hand. Dean puled at the glorious and brief contact. Next came the pink oval vibrator placed on the boy's perineum, "close your thighs and keep this in place. If I find that it's moved, there will be no masturbating for a week." Mr. Novak was a hard dom, but that made pleasing him so much more worthwhile. The vibrator shook against the poor boy's over-sensitive balls and tirelessly stimulated his prostate from the outside. Dean had been achingly hard since class, being tormented all the way thereafter for his indiscretions, the constant stimulation made the tight coil of heat pool under his navel, yet no relief came. The boy groaned in near agony, cursing and begging.
His teacher's smile never faltered as he rubbed copious amounts of lube on his fingers and began working the boy open. "Oh pet, look at how your greedy hole swallows my fingers, as if that will bring you any relief. Just a reminder, pet, the question you got wrong was: 'air is being pumped into a spherical balloon at the rate of 7 cubic centimeters per second. What is the rate of change of the radius at the instant the volume is 36π? The volume of a sphere of radius r is 4π/3 r3" Dean mewled, pushing back as much as he could against his restraints without also losing the vibrator between his legs.
As Castiel's fingers opened up the pliant boy, Dean tried to get his mind to remember how related rates worked; if he didn't come, he very well may die, and for that, he can't think og anything about math that wouldn't generally give him a hard on.
The older man scissored him open, not delving deeper than needed, saving that for his cock to do. His teacher could see the gears shifting in the younger boy's head, trying to figure it out. Castiel openly loved math and found it very sensual in it's own way, but nothing was more sexy than Dean trying to work out a problem; the furrowed brow and curling lashes as his evergreen eyes saw imaginary numbers and letters, his plump lips pursing, occasionally being moistened by a delicate pink tongue while his mind worked through numbers. Nothing was more beautiful.
Dean's teacher began slicking up his own leaking dick, getting ready to mercilessly fuck into the younger boy. The pain in Dean's lower body throbbed and diluted his mind with nonsensical torment; he was his teacher's toy being wound up.
Castiel laid on top of the younger boy, lithe body pressing against muscle under a mutual filament of sweat, Castiel's legs wrapping around Dean's, lining up to bottom out. In one smooth thrust, the teacher was balls deep, reveling in the combination of tightness and reverberate from the vibrator. Before the older man began his truculent pace, Dean remembered his fellow student, Charlie Bradbury mentioning how she answered the question while comparing marks at the beginning of class.
Screaming the answer in a mix of pain and pleasure, Castiel sighed and muttered something about 'no fun' as he slid his hand under Dean to remove the cock ring.
"How?"
"What do you mean 'how'? Just undo the ring, please, sir!"
"Answer me, boy."
"Charlie told me at the beginning of today's class, sir!"
"Mhm, cheating, and much like real quizzes, you get the passing mark, however you miss something vital: the lesson. For that, the ring comes off, but I will evade your orgasm until I finish."
Mr. Novak's benevolent voice and I'm-The-Biggest-Assbutt-Ever voice are identical, Dean can contend to that right now. He often uses both in class. Dean let out a sigh of anguish, "please sir." Castiel leaned down and kissed behind the boy's ear and began fucking into him quickly and hard, never missing his prostate with his fist tight around the base of the student's cock, effectively replacing the cock ring. The angle was awkward with one hand under the boy, but this did nothing to stop Castiel from using his student's ass for his own pleasure. The tight coil of heat in Dean's belly only grew with every rough drag of Mr. Novak's cock stretching him from the inside-out.
Castiel leaned down to the body under him again and whispered, "does my naughty boy still like to break the rules?" For the third in ten minutes, Dean felt what should have been an orgasm just constrict within himself, cock throbbing in his teacher's hand. The boy was nearing tears when he felt his teacher's rhythm begin to become erratic, nearing his own orgasm, and the boy knew he could hold out just a little longer, prove he could take anything and everything for his teacher.
At last, Castiel groaned long and deep. Dean felt his ass fill and the hand around his dick let go. His teacher bit into his shoulder and fucked gentler through their orgasms; Dean was busy screaming, releasing what felt like the biggest load ever all over Castiel's black satin sheets and himself, feeling nirvana for finally being granted relief. The pleasure was beyond anything he had ever felt. The boy laid in his own wet spot while the thin body above him pulled out, minding the over-worked hole, and pulled the oval vibrator off and set it away.
Dean was panting and falling asleep when Castiel unlocked the cuffs and sat down on the double bed, petting his sated student. After allowing Dean a few minutes peace, Castiel picked up the boy and carried him like a child: Dean's arms and legs dangling behind his teacher, head snug against his neck, mumbling things that sounded like 'manly man' and 'don't need to be carried', though too tired to put any animus into the words, leaving Castiel to roll his eyes as he walked with his student in his arms back to the room he uses explicitly for sleep.
The older man dropped Dean on the soft duvet and began cleaning him up, the boy allowing Castiel to handle him. Once he was clean, Castiel pulled him under the duvet and pressed the boy's back to his chest.
"Was that too much, Dean?" Castiel asked meekly.
"No man, I was loving it."
"I'm glad... Dean, what are we doing?"
Dean turned in the bed to face his teacher. They've been sleeping together for only a little over two weeks, sharing kisses when they can, but mostly it was spent in Castiel's sex-room. They never spoke of what they were doing in terms of their relationship- generally, the conversation was about sex or other more commonly friendly topics: what Castiel was cooking Dean, TV shows, books and the likes. Dean smiled and kissed the older man, pressing their bodies together.
"We're doing whatever we want," Castiel stared reverently at the boy; he was thirty and Dean was seventeen, soon to be graduating, starting his life. Where would his high school math teacher fit in there? "I just... Dean, what is this? Am I just an outlet?" Both men hid their pained shock at the words, Dean snaked a between Castiel's. Though they did enjoy fucking, Dean loved to just stop by Castiel's place to hang out, sex or not. Dean wanted more with Castiel, but had no clue how to say it, how to explain he wanted to make everything work, no matter the obstacle.
"Of course not, Cas! You're... you're mine, and I'm your's... and I don't want to be anyone else's..."
Dean shied away while Castiel searched his face for any clues of calumny, but found none. Relaxing into the cuddle again, Castiel pulled Dean in closer, resting his head on top of the boy's before kissing his forehead and saying, "you've been mine since the beginning, and I guess that does make me your's."