Dear reader: please be warned that this is a story with BDSM, bisexuality, watersports, and other distateful activities. You have been warned!
I was a grade 12 math teacher in an upscale charter school. Thankfully math was not one of the subjects that required adherence to any quirks of the Charter curriculum; and it had the added bonus that most of the students assumed I was out of it and so usually didn't engage me in any of the hazing type stunts reserved for some of the teachers of more socially conservative subjects.
But Miss Priscilla Grace Compton, one of the school's archetypal rich bitches, had obviously decided to push me today. Or possibly she had taken a dare. No matter.
The parents may have been under the illusion that a conservative curriculum would isolate their little darlings from the corruptions of the modern age; but a combination of internet, movies, and peer pressure meant that these kids knew more and were more depraved than half the faculty. You know how kids used to throw a party in a house when the trusting parents left on a weekend? You know how they'd drink beer and pet, and even do reefer or X if somebody brought some in? That's old school. Kids today went in for full blown orgies. They didn't just hook up; they hooked up with everybody. I was jealous.
But I was also intrigued. Grace was the typical spoiled brat; prom queen type, arrogant, snotty, hot as hell and fully aware of it. I had seen her squashing mere mortals in her path, or even not in her path but just available to be squashed.
I had idly daydreamed about a comeuppance for this one, but I knew it had to be more than just a simple standard punishment, or it would do no more than add to her reputation. No, I had to get to her in some way that left her both marked by experience and changed permanently, hopefully for the better. Also, I just wanted to have a little sadistic fun.
But this day she foolishly gave me an opening.
She came in just at the end of the influx of students at the beginning of class, coming in the back door of the classroom and quickly sitting down in the back row, slouching to make herself inconspicuous if that were possible.
No matter; I had seen her, and I immediately saw the glistening evidence of what she had done. She was probably counting on the fact that a dork like me either wouldn't have a clue or would be too shy to say a word; but unfortunately for her I was somewhat more experienced in these things than she assumed. Probably it was on a dare; but for whatever reason she had come to class with quite visible globs of cum all over her pretty face. She hadn't tried to clean them off, and was probably hoping that if I noticed I would be too shocked and embarrassed to react coherently. Or maybe she just wanted to shock and embarrass me for the hell of it.
Actually, I found her quite beautiful at that moment. She was grinning foolishly with, I presume, a mixture of embarrassment, insecurity, and mischievous glee. I thought the globs of cum made her glow.
I waited almost until the last minute of class, giving the sperm a chance to dry on her face for the hour, so it would be harder for the other students who inevitably looked at her to see.
"Miss Compton, you are guilty of gross misconduct unbecoming a student of this school, and as a result you will stay after school and accept your punishment. Would you like to discuss the reason for your punishment?"
"Er, no." She was suddenly panicking, worried that word would get back to her parents. She could only hope that the other students wouldn't clue in to what was going on and blab to their parents, or that I myself would not send any official word to her parents directly.
I picked up the wooden pointer from its hook on the wall and slapped the palm of my hand vigorously. "Very well. You shall receive 50 hard strokes from my rod on your buttocks, and spend one half hour in detention."
Sometimes charter schools had their advantages. Ours allowed corporal punishment; or at least it was understood that the school turned a blind eye, an attitude almost demanded by the parents. In fact, many of the parents were paying the high fees in order to send their kids to a school where the whip would be applied surreptitiously but frequently.
At this she turned pale, whiter almost than the traces of sperm still barely visible on her skin. Nobody had ever received 50 of the painful blows before, and my vicious punishments were somewhat feared.
"Of course, there is an alternative that may save you. You obviously had a partner in crime, and if that accomplice volunteers to come forward they may receive the punishment in your place, instead of you. How about it? Anyone willing to make the noble gesture and confess?"
She briefly glanced across the room, and I knew the hook was set, deep.
"I did it, Sir." James Abernathy querulously raised his hand and spoke up to claim the right to take the burden from the shoulders, or rump, of his lady fair.
"Very well; I expect you both in my office in ten minutes. Yes, both of you. Grace at least should witness what you are going through for her sake, and witness the consequences of her actions."
Damn right she was going to be a witness. Let's just see if my little show can pierce through that shell of self-satisfaction once and for all.
Mercifully for the two of them, the bell rang just then as I had intended and the room emptied out at phenomenal speed, seemingly in defiance of the laws of physics, with the three of us retiring to my office in a cul-de-sac at the end of the third floor. As it was Friday afternoon the school would soon be completely deserted.
We went inside the office and I locked the door.
"All right sir Lance-a-lot, bend over that work table the long way, so you can grasp the table legs at the far end. I don't want any violent squirming or any yelling, so I am going to strap you in place and place a gag over your mouth."
He did and I did, using a ball gag and plastic tie strips to secure his wrists and keep him bound to the table.
I pointed at the other work table that was crossways to the first and gestured at her. "You too. Lie diagonally across that other table, so that you are facing him. I'm not going to have you yelling and attracting attention or interfering in any way. You are going to stare straight at him and watch him getting every single stroke. Get in position."
I of course had an ulterior motive in that I wanted to tie her down straddling the corner of the table. Specifically, I wanted her clit to be right up above and against the corner.
She meekly complied, and I tied her down and gagged her too. Fortunately they were both still in too much shock from being caught to be thinking too much about what was happening. I then fastened belts around their waists and the tables. They were in no position to object to the surprises I was about to inflict on them.
"I believe I failed to emphasize a further detail. When I said my rod was to be applied to your bottom, I meant directly. You will receive the strokes applied to your bare bottom, for maximum effect and maximum punishment."
If anything, this reduced them into more shock than before. She started yelling inside her gag, but he just looked desolate.
I removed his shoes, socks, pants, and underwear. Then before he reacted I fastened his ankles spread apart to the table legs with more straps, so that he was held open and helpless.
The table was short enough that he was hanging slightly over the edge, so that his cock and balls were clear of the top and hanging down between his legs. I reached under and caressed his balls for a while, then grasped his cock and started to stroke him. After masturbating him in front of his mute and immobilized girlfriend for a while I dropped his cock and proceeded to strip off my own clothes.
"I'm sorry if I gave you the wrong impression, but when I said that 50 strokes of my hard rod were going to be applied to your bottom, I was not talking about whipping you with the wooden pointer."
At this he started thrashing around frantically, and yelling into his gag. I didn't mind; it would just increase the pleasure on my cock as I fucked him. I squirted a large amount of lube at the top of his crack, and put another large amount on my cock. I reached for his cock with one hand and resumed slowly jerking him off while I greased up my cock with the other hand. I then started working lots and lots of lube into his ass with one, then two and then three fingers.
When he was as ready as he was going to be, I placed the tip of my cock against his asshole and started to gently thrust against him as though I were fucking him but not going all the way inside.
I knew he was getting hot as his cock was now almost harder than my wooden pointer had been. I understood that he was receiving sensory overload on many levels, and I was going to have to play him exquisitely. I slowed down the hand on his cock just as my cock started to slowly sink into his very slippery and warm asshole. I moved slowly and deliberately as I sensed that he was starting to respond with some pleasure, and I was now determined to make him feel good but without letting him cum.
Meanwhile, Grace's eyes were like saucers. She watched as he was getting initiated into sodomy, and she watched as he started to writhe with enjoyment. She was getting hot, and she had started to grind her crotch against the edge of her table.
.... There is more of this story ...