You can buy it here: Blackmailed By The Headmaster
Moving around so he was standing directly behind me, he placed one of his palms on each of my ass cheeks and started slowly spreading them apart. His hands were warm, but I shivered from the shame of having myself so thoroughly exposed.
“Yes, Miss Fenwick. Thank you for demonstrating my point so efficaciously. The anus,” I jerked involuntarily as he ran a finger across my anal entrance, “provides many opportunities to humiliate and subdue the most combative of students. So humbling to have this most private place exposed and violated.” As he said this, his finger wormed around my asshole, slowly stroking its puckered opening.
“First of all, this area is highly sensitive, so the student is likely to display signs of arousal. Let me show you how to check for those, Miss Fenwick.”
Never stopping his methodical strokes of my anal crease, he reached his other hand down and cupped my whole pussy with his hand. Once again, I jumped reflexively at his unexpected touch. “Do try to contain yourself, Miss Fenwick. You are here to learn.”
“I’m very sorry, Headmaster.”
“Oh, you will be, Miss Fenick. Believe me.”
Mr Chapel laughed at loud at the headmaster’s menacing tone. The headmaster increased the pressure of his grip on my pussy, the heat of his hands radiating through my core.”
“Now, Miss Fenwick, in the female, arousal can be detected through the presence of vaginal lubrication. Let’s see what we find here, shall we?”
I felt his middle and index fingers slide between my folds and begin burrowing purposefully through the slick wetness that I was resigned to him finding there. He found his way to the entrance of my pussy and pushed his fingers in roughly, the force jolting me across the desk. The only sounds in the room were the noise of my juices slapping against his hand as he probed the depths of my pussy and the occasional spit of logs from the fire.
“Are you getting this, Mr Chapel? Is the sound of Miss Fenwick’s continued degeneracy being captured for posterity?”
“Yes, Headmaster. Clear as a bell.”
My face flushed at the casual way that the men were referring to my defilement at the headmaster’s hands.
“Good man.” Fingers still deeply embedded in my throbbing core, the headmaster continued his lesson. “So, Miss Fenwick, as you are so ably demonstrating, a subject can become highly excited by the manipulation of their anus. You really are getting quite carried away, aren’t you?” He withdrew his fingers with a final sticky pop and briefly rubbed at my tingling clit as I moaned against his hand, before removing himself entirely from me.
He walked over to his desk and wiped his hands off with an antiseptic gel, the action so clinical and jarring after his intimate exploration of my most intimate areas.
Walking back towards me, he said, “Now, if your subject is also showing signs of arousal in their nipples, as you most certainly are here, draw attention to it, further increasing their discomfiture. Like this, for example.”
Reaching a hand under my body, he started to tug on each of my nipples in turn. “Why are your nipples hard, Miss Fenwick?”
Flustered, I had no idea what to say. My confusion was rewarded with a vicious tweak to the nipple closest to him. I howled out in pain.
“Answer the question, Miss Fenwick.”
“I… I don’t know, Headmaster.”
Another brutal tweak, worse than the last. “That is a wrong answer, Miss Fenwick. Let’s try again. Why are your nipples hard?”
I paused, another tweak, another yelp of anguish from me. I rallied and heard myself say, “My nipples are hard because I’m aroused, Headmaster.”
The Headmaster gave a sigh of satisfaction. “Very good, Miss Fenwick. What fast progress you’re making, given the proper persuasion.” Plucking at my nipples more gently now, strumming at them in a way that was hypnotic and incredibly sensuous, he continued, “Why are you aroused, Miss Fenwick?”
Oh fuck. The man was obscenely good at this. Fearing another agonising twist if I hesitated, I forced myself to say, “Because your finger felt good on my bum, Headmaster.”
“Your bum? We have no room for such playground language here, Miss Fenwick. Did you mean to tell me that my finger felt good in your arsehole, Miss Fenwick?”
“Yes, Headmaster. I’m sorry. Your finger felt good in my arsehole.”
“Much better, Miss Fenwick. In my office, we refer to arseholes, cocks and tits, do you understand? My hand is on your tits right now. Nasty little sluts being punished have tits, not breasts, Miss Fenwick. And it was your filthy little cunt that discharged so copiously onto my fingers.”
“I understand Headmaster. Thank you very much for the lesson.”
How’s Miss Fenwick’s arse going to get used next?
Find out here: Blackmailed By The Headmaster




