Punishment/Lesson   added 2 years ago
  By: sexhopper69  Age: 30  Country: United States

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Categories: Masturbation, Anal Sex, Steady Partner
Tags: fingering humiliate Olderman dildo panties Training student/Headmaster
Location: Other
Roleplay: Student/Teacher
Fulfillment: Act on it
Nature: Humiliating
Enter your story here... The PE teacher had buzzed ahead telling him to expect me. She had not however, prepared him for exactly what I was to be punished for.

He could easily have lost his job for the punishment he chose for me.  I mean really should lose his job for the punishment he chose for me.

I knock at the door…

“Come! “he shouted.

I stepped inside. I was still wearing my gym clothes…a tight, powder blue top, showing-off those incredible, juicy tits to perfection. Below…I was wearing a tiny gymslip, displaying far too much of my smooth, naked thighs and on my feet, a simple pair of white training shoes.

God I looked good!

It could be incredibly difficult being the head of the school at times, particularly when he had to punish naughty girls like me. He was my headmaster and, from the moment the thought entered my mind,his truly knew he was in the wrong.

He could feel his cock twitching hard as he looked up at me standing still beforehim.

He always had a philosophy of punishing his students in a way somehow related to the crime that they had committed, but perhaps in this case he should have forgotten about that, but, as he well know, for right or wrong.

“So young lady! What have you been up to this time?” he asked.

I stared down at my feet, my cheeks flushing scarlet.

“Well come on girl, I don’t have all day!”

I looked up at you briefly, mumbling something quite inaudible.

“For goodness’ sake girl, speak up! I doubt anything you have done now can be any more shocking than the things you have got up to in the past now can it?”

How wrong could he be?

Finally, I looked up, my eyes piercing my own and said in a full, clear voice…

“I was caught playing with my sex toys in the changing room Sir.”

It was his turn to blush now. He stared down at his desk, pointlessly shuffling papers from one place to another and swallowing hard, but there was another more powerful emotion than embarrassment making itself known. His cock was hard and pulsing. He wanted me and as he took a deep, calming breath he decided…he might just have to take me.

HE looked up, a little more composed now.

“I see. Well…a young lady of your age should not know about such things, let alone be performing them during school hours. You do realize I will have to punish you don’t you?”

I nodded my head, more than a little nervously.

“As you know…I like to relate your punishment to the deed you have performed. Remember that time you were caught littering and I made you clean the entire school yard?”

Again, a wordless nod.

“Well…I am going to start by humiliating you. If you enjoy playing with toys yourself so much you can show me…”

“But sir…”I protested and really should have backed down.

“No buts young lady. My mind is quite made up. Now…pull over that chair, remove your underwear and sit down. I want to see what you find so stimulating about that body of yours.”

He watched me, secretly enjoying my discomfort, as he remained standing.

"would  like some advice on a better way of doing this," he said walking over to his big desk. "May I show you "

As I replied in the affirmative I moved until I was standing next to him and bent over giving him a good view of my breasts. I heard a sudden intake of breath. and I continued to prattle away mindlessly at my pussy I deliberately let my dildo slip to the floor.


"Silly me," I said as I turned away to bend over and pick it up, knowing that he would get a flash of my ass encased in white silk.

"Let me help," he said standing up as I did so that we bumped into each other.

I stumbled and he caught my arm to steady me, his fingers brushing my nipples as he did. I moved to the corner of the desk and sat on the edge, my gymslip riding high on my tanned brown thighs.


"It looks like I might need some extra tuition Sir and I wonder if you could help me?" I said gazing at his  bulging trousers.

"I am sure we could come to some arrangement that would suit us both," he said, "but you need to learn the rules. You've not been paying attention and that needs to be rectified."

I could now no longer keep my eyes from his bulging trousers. "I am prepared to do anything you tell me," I said.

"Well for starters I want you to unzip my trousers and release what you have caused since you walked in here."

My eager fingers quickly undid his belt and unzipped him and pushed his trousers and shorts down so he could step out of them. As I went to take him in my hand he said, "No! You need to be taught patience young lady. Everything will come to those who wait. Put your hands behind you on the desk and lean back so that I might admire what you have."

I did as he said and this made my little gymslip ride up so that my pussy showed.

"What have we here?" he asked as he ran a finger over my thigh, tantilisingly slowly. "And here?" as he flicked my right nipple. "I think I have a horny little student that needs a good fucking."

"Oh yes please sir," I replied, eager to do whatever he had in mind.

He slipped the straps of my top from my shoulders exposing long rigid nipples yearning to be tweaked and pinched. His fingers did just that much to my ecstasy as I felt tremors run all the way from my nipples to my cunt. Without a word he pulled me towards him and pushed his thick 8 inches into my pussy.. "Oh so lovely and wet," he murmured as he continued to fuck me, his dick now thrusting in and out of my fuck hole loosening me up. I felt his balls begin to harden and without any word he pulled himself from my pussy. "I want you to bend over my desk," he said, pulling me to my feet. "You deserve a spanking for poor behavior." He smacked my tight little ass making me even more excited. "Spread those legs for me."

I suddenly felt the head of his cock pressing against my asshole. I pressed back towards him and felt him slip in, deep, oh so deep. He fucked me hard, As I was about to climax he grab my dildo out and pressed it into my wet pussy. He kept on pounding me harder and harder.

I was so close to chumming he pulled the dildo out and  he had me sit down on his shaft, feeling him go in deep and ground my ass. He grabbed my nipples, pinching them as I rode him, my head flung back.

"Come with me he said. I want to fill your cunt like never before," he said as he twisted my nipples. I increased my speed, rising right up until he almost slipped out and then plunging back down again enveloping him in my tight, asshole. His one hand suddenly went to my clit and as he flicked it we both exploded in orgasm. My juices dripping onto his balls. "Now off you go and come back tomorrow morning early for another punishment/lesson. Only I want you to bring a other toy with you. Is that understood?"

"Yes, " I said wondering what tomorrow’s lesson would be!




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