Dinah Fyre's Erotica Wonderland

Dinah Fyre's Erotica Wonderland

Blackmailed By Her Student - The final instalment!

Part Three: Miss Fenwick learns the true meaning of "pussy-whipped" đŸ–€

Dinah Fyre: Erotica Wonderland's avatar
Dinah Fyre: Erotica Wonderland
May 05, 2026
∙ Paid

Parts One and Two are here


Blackmailed By Her Student - Miss Fenwick is back!

Blackmailed By Her Student - Miss Fenwick is back!

Dinah Fyre: Erotica Wonderland
·
Apr 21
Read full story
Blackmailed By Her Student - Bound to the bed and punished

Blackmailed By Her Student - Bound to the bed and punished

Dinah Fyre: Erotica Wonderland
·
Apr 28
Read full story

When I recovered my senses, Sebastian was still watching me with that same superior, amused look that he’d had since he’d turned up on my doorstep earlier that evening. He was also entirely naked and slowly stroking his massive erect cock with one immaculately-manicured hand.

“Well, Miss Fenwick, didn’t you just have a lovely time?”

Having learned by now that a response was expected, I replied, “Yes, Sir. Thank you, Sir. Your little whore is so grateful, Sir.”

“Very good, Miss Fenwick. I must say, even having witnessed you cumming hundreds of times, it was far more gratifying in person. Although I was a little worried that your screams might wake the dead. This ancient dump is almost certainly haunted.

Now, I’m sure you’re just longing to feel this cock inside you, but let’s have a little fun first.”

For the first time, I realised that he held a riding crop in his other hand. Mr Chapel had left a variety of accessories in my room during his many nights here and this little whip could be used to devastating effect.

Inspecting the tip of the crop, he said, “I remember this little bastard. It’s got quite the sting in the tail, doesn’t it, Miss Fenwick?” And he flicked it briskly across one of my nipples as I gulped and cried at the sudden, sharp pain.

“Yep. Just as I thought. Right, Miss Fenwick, we’re just going to rearrange you a little bit.” He nimbly untied my legs and just as quickly refastened them so that they were spread widely and tethered to the headboard, my bound wrists still restrained between them.

I was incredibly exposed like this, the pillow under my bum pushing me up obscenely, my entire pussy and tight rosebud arsehole on display for Sebastian’s imperious and inexorable scrutiny.

“Beautiful,” he said. “Now, Miss Fenwick. I know you are inclined to squeal when having your pussy whipped, but I also know that you’ve cum all over this crop countless times. You can’t expect me to show mercy, but I will kiss you better on any areas that I punish. Of that, you have my word. Shall we proceed?”

“Yes Sir, please Sir. Please whip my greedy little pussy.”

“Very good, Miss Fenwick. I can’t wait to see you bounce for me.”

And with that, he flicked the crop ruthlessly, squarely at the entrance of my still trembling pussy. The sound it made slapping against my sticky hole was still mortifyingly audible, even above my squeak of pain. Restrained as I was, I jumped, just as Sebastian had predicted, when the blow hit. My whole pussy clenched, sending the familiar waves of pleasure along its length, even as I bit my lip to distract from the smarting ache that was bursting across my sex.

“And that’s one. Shall we make it ten in total, Miss Fenwick? As fun as this already is, my cock is in distracting need of satisfaction.”

“Yes Sir. Ten please, Sir.”

“You are a good girl, Miss Fenwick. This school is terribly lucky to have you.” And with that, he aimed another devastating snap of the whip, this time against the handprint that had formed on my thigh from his earlier assault. I jerked against the ropes again, thrashing helplessly as the heat coursed through me.

“Seems a shame to leave the other side out, doesn’t it?” he said, before delivering a lightning-fast strike to my other thigh as I shook and cried. My pussy was soaked and I felt my juices trickling across the recently tormented skin of my thighs as the warmth of the blow radiated through my legs.

Before I knew it, Sebastian aimed another strike that landed directly on my still throbbing clit. My entire bottom half exploded in fiery pain, the sensations rippling across the three other areas that he’d whipped so far. I screamed out, no longer even aware of the sound, only of the pain, the exquisite pain, and the steady hum of my pussy that somehow still wanted more.

“One more here, I think,” I heard him say, before the crop struck my exposed pink arsehole. My hands and feet fought against their bindings, but the ropes and leather held fast as I let out a harsh, guttural moan. I had been very thoroughly sodomised by Mr Chapel last night and my poor puckered entrance hadn’t yet had time to recover.

“Oooh, that was a good one, wasn’t it, Miss Fenwick,” Sebastian said, gleefully.

“Yes, Sir. Thank you, Sir. Your whore is grateful, Sir.” I somehow managed this without sobbing.

He trailed the tip of the crop from my arsehole, up along my pussy, smearing my juices around before manipulating it across my clit.

“You’d like to cum very badly, wouldn’t you, Miss Fenwick?” he asked.

“Yes, Sir. Oh yes Sir!”


The rest of this story is free for paid subscribers only.

If you’d like to read the rest, it’s available here.

More Headmaster stories here and here 💋🎓


This post is for paid subscribers

Already a paid subscriber? Sign in
© 2026 Dinah Fyre · Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture