Femdom story: Headmistress from hell

Disclaimer

This story contains Femdom, non-consensual torture, older woman/young boy, whipping, pegging.
If you’re not into Femdom and non-consensual torture don’t go further with the reading.
(Femdom, F/m, young, NC)

 

Headmistress from hell

The crop hissed.

“… mmmfff…”

The boy tied on the bed screamed but only a muffled moan could be heard through the ball-gag that was forcing his mouth painfully opened. His arms and legs pulled uselessly against the ropes that were taking his wrists and ankles tied to the bed. A woman was standing at his side hitting him with all her strength. She was moaning too, not for pain, but for both effort and pleasure.

“… 128 … 129 … 130!”

The woman put down the crop and bent down. As she did before every ten lashes, she grabbed the boy balls that were hanging between his spread legs and pulled, squeezed and twisted as hard as she could. She did it so hard that the boy were pulled few inches off the bed. His muffled screams of pain matched his expression of pure agony while the woman expression was of pure delight. After a minute of wrings and tugs, the woman took the crop and started the count again.

“… 131 … 132 … 133 …”

Every leash marked the boy’s soft skin. His pale ass cheeks were became deep red and were bleeding.

“… 139 … 140!”

This time the woman took her shoe from the tip and started hammering his cock and balls with the sharp metal heel. Despite the moans of the boy that made very clear how much pain the boy was suffering there were no trace of pity in that woman, just pure ecstasy for causing as much pain as it was possible. When the minute of “pause” was over cock and balls were bleeding. That made the woman satisfied and even more turned on. She started the whipping again.

“… 149 … 150!! Finished! Are you happy?”

The woman asked laughing for her own irony. Then she took her shoe and gave the boy’s genitals another violent and wicked series of hits. He was struggling while trying to escape his genitals destruction. The woman went on hitting until the thin metal heel had opened many wounds on his cock and ball-sack. Then she stopped and looked for a moment to her work result with satisfaction and then she put the shoe back on her foot. She went to the near dresser and took out a huge strap-on. She let her skirt fell on the floor and wore the strap-on over the pantyhose so that it would reduce the pleasure of the strap rubbing on her cunt and would made the fucking go on for a longer time. She went back to the sobbing boy and pulled his head up by his hair so that her huge black rubber cock was just a few inches from his face. She said nothing but just took him there to stare at the scaring cock while she lubricated it imitating a masturbation gesture. She then moved as if she was fucking her own hand with increasing speed, enjoying the terrified gaze of the boy that was already imaging the pain that thing was going to cause to his asshole. The woman wanted to increase his terror so she explained what she was going to do to him.

“Can you see it? Can you see how huge it is? Do you see how long it is? I cannot take it all in my hand. But despite its dimensions and despite your little butt is virgin… I’m going make it enter your asshole all the way in! Better… I’m going to hammer it inside you. It will be so nice to rip your asshole apart! I’m going to make you scream! I’m going to fuck you so hard, deep and fast that you will shit blood for a week!” she whispered aroused.

The boy knew he had no escape and stared to the giant cock that was moving to and fro just in front of his eyes knowing that thing was going to destroy his asshole. Then the woman climbed the bed and was over his back on all four with the huge cock dangling from her crotch. It was so long that the tip were touching the bed between the boy legs. She grabbed and bent it and pushed it between the boy ass cheeks so that the tip was on his sphincter. While she took it there, she bent down and whispered:

“Are you ready, little whore? I’m not going to give your hole the time to dilate; it’s going to be painful, veeery painful.”

With an evil grin, the woman started pushing the strap-on inside the virgin asshole with all her strength and her weight combined. As she said, she was not holding back to that helpless virgin hole. She pushed as hard as she could and when the wide rubber cock tip was in she started ramming it with all her might forcing the monster all the way in. The boy screamed his lungs against the gag. His eyes were bulging out in a pure agony expression. When the cock was full in she started a really wild ride. She was not just pumping it savagely in and out; she was also swinging her hips trying deliberately to break that asshole more than what the giant dildo had had already did. After about twenty minutes of brutal torture, the woman felt her orgasm coming and, for the last minute, she speeded up the rhythm to the max. When the orgasm faded, she lied over the boy that had drenched the pillow with his tears and the sheet with his blood. She remained for a couple of minutes to recover before got back up. When the giant cock exited from the boy anus, it was followed by a spurt of blood. The woman sat on the pillow in front of the boy, she took out the gag from his mouth, raised his head by the hair and put the dirty cock covered in blood and shit in front of his lips.

“Clean it!” she ordered.

“Clean it all or I’m going to start it again from the very beginning.”

The boy did it gagging on it because revulsion. When he finished the woman stood up, removed the strap-on and then she threw it on the floor and exited the room. After half an hour, she came back naked and relaxed by a regenerating shower. The woman went to the bed and sat on the pillow spreading her legs and putting her cunt against the boy nose.

“Sniff my cunt, feel the strong scent. I just peed, feel the aroma.”

She extended her legs on the boy shoulders enveloping his head between her soft flesh. She crossed her ankles and closed her legs just enough to trap his head and avoid for him to turn it away and so she forced him to inhale by her dark bush. This was one of her way to show her superiority and the subjection of who fell into her clutches. While the boy inhaled piss and pussy juices smell the woman instructed him about what would happen after their very first meeting.

“Now you will go home. Not a single word about this will exit from your mouth. Remember that your parents works in my school and I can fire them both. I did some investigation and I’ve discovered that they had a mortgage to pay and they barely can afford it. So, from now on, it will be not necessary for me to drug you and tie you while you’re unconscious like I did today. You’ll say to your parents that you come to my home to have private lessons twice a week. Lessons that you will pay with all the money your parents give you for your expenses. Here you will be my slave and you will obey to my every order, even if there will be few as I mostly will have fun in torture you like today and even worst. If you don’t submit yourself to me your whole family will be in abject poverty. Your little brothers will be taken in an institute because your parents will not have money to maintain them. Oh, did I told you that beside be your high school headmistress I’m also the manager of the only one institute that can accept your little brothers? And you don’t want that your brothers could be in my hands forever, would you?”

The boy started crying and between his sobs he said

“No, madame.”

“Very good. So I’ll see you here in three days from now for your, now usual, private lesson. This night try to study hard because tomorrow you will have an oral exam with me and I’ll be very strict with you from now on. Obviously a grade lower than an A will mean more tortures when you will come here.”

The sadist headmistress rubbed her cunt on the boy nose while she was talking, enjoying his distress.

“Saturday I want you to come with me for little shopping. I saw a pair of very nice shoes in a shop window. Long pointed toes and very sharp metal heels. Can’t wait for use them on you. Take all your money with you. If it will be more than enough to pay them, I’ll take the change. If it will be not enough you’ll have ten extra lashes for each dollar that I’ll have to pay.”

The headmistress stood up.

“You’re dismissed. Don’t complain too much because next time will be lot worse.”

An evil laugh filled the room. While the boy stood up with difficulty and dressed, the headmistress went to check written exams of the boys of her class without look at the last of a long series of young boys she have had in her wicked claws. A satisfied smile appear on her lips while she put an F on the exam of the same boy she just finished torturing. An F that he didn’t deserve. If that little worm hoped in passing and escape from her like this he was totally wrong. An evil laugh came from the headmistress from hell.

 

End.

8 thoughts on “Femdom story: Headmistress from hell

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