Dinah Fyre's Erotica Wonderland

Dinah Fyre's Erotica Wonderland

Blackmailed By The Headmaster 2: Another Hard Lesson - Final Instalment!

Part Three: The Headmaster claims another teenage pupil's ass 🍑

Dinah Fyre: Erotica Wonderland's avatar
Dinah Fyre: Erotica Wonderland
Apr 14, 2026
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Parts One and Two are here 💋

Blackmailed By The Headmaster 2 - Another Hard Lesson

Blackmailed By The Headmaster 2 - Another Hard Lesson

Dinah Fyre: Erotica Wonderland
·
Mar 31
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Blackmailed By The Headmaster 2 - Another Hard Lesson - the story continues!

Blackmailed By The Headmaster 2 - Another Hard Lesson - the story continues!

Dinah Fyre: Erotica Wonderland
·
Apr 7
Read full story

Courtney dropped to her knees, quite overwhelmed by the morning’s events so far.

I decided I could wait no longer to plunder her delightful arse for myself. We had many months together for me to act out any perversion of my choosing upon her willing, ripe body. Every hole would be mine to savour at my leisure. For now, though, my cock was in urgent need of satisfaction.

Unbuttoning my trousers and removing them and my briefs, I walked over to Courtney’s prone form, my academic robes billowing around me. I very much enjoyed the visual effect of them on camera as I buggered a student on their knees like this.

Standing over Courtney, I fisted my cock authoritatively as I surveyed her naked curves. Her and Chapel’s cum still gleamed on the floor, as well as on her beautiful face.

“What a mess you’ve made, Courtney,” I said, ominously. “Why don’t you go ahead and lick that up?” I continued, helpfully pointing at the spots on the rug where their juices glistened.

She stared at me for a long second and I saw her wrestling with the last of her self-respect. I revelled in the inevitable moment of capitulation as she bowed her head and tentatively started to tongue her cunt juice from my study floor.

“I think you have more gumption than that, Courtney. If a job’s worth doing, it’s worth doing properly, don’t you agree?”

After another long stare, she started to lap her and Chapel’s emissions up enthusiastically, even making smacking noises with her lips. Oh yes, this latest Bailey Girl and I were going to have a lot of fun together.

My balls tightened in response to this thought and I positioned myself directly in front of Courtney so that my cock was level with her mouth when she lifted her head.

Pointing at my cockhead, I said “This is going directly up that snug little arsehole of yours in about sixty seconds’ time, Courtney, so I suggest you get it as wet as possible, to spare yourself any unnecessary discomfort.”

She gaped at me and I seized the opportunity to stuff my cock into her mouth, grabbing the back of her head and forcing my rampaging prick down her throat. She moaned in protest, the vibrations tremoring delightfully along my thick length.

My thrusts along her gullet caused her to start choking and I felt those delicious streams of her spit finally bathing my cock. I grew ever harder as I watched her dutifully swallowing my prick, her lips perfectly encircling my thick meat. Such promise awaited!

“You’re doing very well, Courtney. My one hundred predecessors have done a most adequate job of preparing you for me.” Winking again at Mr Chapel, I said, “And it’ll be at least one hundred and two cocks you’ve sucked before the day is out.” Chapel’s cock had already been at half-mast again but stiffened entirely at the prospect of fucking Courtney’s mouth himself.

Her eyes streamed with tears as her mouth slid up and down my hard shaft, wetly coating it, her lips sucking and smacking at my impatient prick.

I felt the first spasm of an impending orgasm surging through my cock and balls. It was so very tempting to cum in this lovely young girl’s mouth, but I had other plans for the copious load that was waiting to be unleashed from my heavy ballsack.

Withdrawing my cock, I pulled away from Courtney as she slumped back on the floor to recover, rolling around, her tits bouncing merrily as she tried to get her breath back.

I was now really quite uncharacteristically mad with desire. My prick was rock hard, gleaming all over with her saliva, my mind aflame with lust for my latest Bailey girl. I was struggling to maintain my usual detachment in my desire to thoroughly sodomise and defile this gorgeous creature before me.

Shaking my head in an attempt to clear it, I ordered Courtney back on her knees, checking that Chapel had arranged the cameras appropriately to capture the session from this angle. I already knew that I would be re-watching this footage for many years to come.

Getting into position behind Courtney’s upthrust backside, I briefly caressed her silken arse cheeks with the palms of my hands, enjoying her shiver as their roughness contrasted with the smooth delicacy of her buttocks.

“Reach back and spread these for me, like a good girl,” I commanded, tapping her arse briefly with my retreating fingers.

She immediately reached back and did as I asked, her beautifully manicured nails lightly digging into her cheeks.

I ran a finger along the cleft of her magnificent arse, enjoying watching her winking little arsehole twitch when I touched it. I lightly traced slow gentle circles around the small ridges of her anal bud and she tremored and moaned under my touch.

“Have you been arse fucked before, Courtney?” I asked.

She hesitated a moment, then said, “Yes, Sir.”

What a pity. She would pay for this. But I no longer felt any guilt about plundering her arse exactly as I pleased.

“I see. Did you like it?” I asked.

“Sometimes, Sir.”

“Do you think you’ll like it today?” I asked, slowly starting to insert my finger into her spread arsehole, making lazy circles in her tight sphincter, the tip of my finger just barely spearing her anal ring.

Gasping, she said, “I think so, Headmaster.”

I removed my finger and gripped my cock tightly. “Ask me nicely to fuck your tight little arse, Courtney. Tell me exactly how badly you want my fat cock inside your filthy little hole.”


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