Jennifer and the Headmaster - Sex Stories

Jennifer and the Headmaster

... he had ever set eyes on kept playing over and over in his mind. All night the erections would not subside as he kept stroking his cock and ejaculating thinking of this woman that had captivated his mind and heart. He had waited years for such a hypnotic amazing creature to enter his life and he needed to seize the day. I nervously drive into the parking lot and hurry into the school looking back to make sure no one noticed. The halls and classrooms were empty like he said as everyone was away on a field trip. I enter the secretary’s office and knocked on his door, I hear a commanding voice say enter and as I did I suddenly felt like a genuine naughty school girl being sent for punishment. Mike is sitting behind his desk doing some paper work and he motions for me to sit in the chair in front of his desk. I sit anxiously waiting for him to address me when I notice three school canes and a leather paddle resting on the side of his desk. My heart starts to race knowing these are intended for me, as I sit staring at them I fail to notice Mike looking at me. He clears his throat and makes me jump, He asks me if I thought about my life style and behaviour and how it could be corrected. Yes I reply but before I can say anything else, Mike begins to inform me how we would proceed this morning. Mike says, the way I see it you need a good old fashioned caning on your bare bottom, normally a young girl would get six but since you are a mature woman I am inclined to give you twenty four ...

... strokes with the senior cane. I sit quietly hanging on his every word as he continues I expect you to take your punishment like a big girl and I hope I do not have to restrain you. My mind is flooded with images of him tying me down to whip me and my pussy is responding by getting wetter with every word. Mike looks and me and asks if I understand and agree with him, I just nod yes. Mike rises from behind his desk and walks around to the front, he takes my hand and directs me to the front of his desk. He puts his hand into the small of my back and lowers me face down onto the desk. I feel him start to gather the hem of my skirt and raise it up my thighs to rest on my back. Jennifer! He exclaims, you are not wearing any panties, you naughty, naughty girl, just for that I am going to add another dozen to the count and you will now get thirty six strokes with the senior cane. I was beginning to regret this decision but it was too late now. I see Mike reach for the cane and after a few practice swings in the air he places it against my trembling flawless white globes. He takes a few seconds to admire the creamy flesh of the most perfect spank-able bottom he had ever seen but he had a mission to accomplish and must stay the course. The only thing I hear is my heavy aroused breathing then swoosh, WHACK, oh shit I say out loud, then another WHACK, damn I grit my teeth. Two more hard fast ones that cause me to bolt upright, Mike pushes me back down saying he will restrain me if he has ...