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Extramarital affair goes to Hawaii.

You are so beautiful."

She released by hair and looked me into the eye. "None of that matters now. I told you to do something and you didn't do it. Do you understand?"

I nodded.

"Then ask for your punishment David. So I know you understand."

My stomach filled with butterflies as the words escaped my lips. "Please Miss. Please punish me."

Her gaze left me and searched the room as I watched her collect objects and items, including office supplies from the desk. Binder clamps, the ruler, rubber bands, thumbtacks and scotch tape.

"Scooch forward," she instructed. "I want your butt right on the edge of the chair." I repositioned myself as requested.

She reached into her knapsack and pulled out a roll of duct tape. She positioned my arms on the arms of the chair and slowly and tightly wrapped the tape around them, securing my arms to the chair.

She slipped off her shoes and slowly peeled off her socks, wadding them up and then telling me to "open wide" before stuffing them in my mouth. She wrapped the tape around my head, sealing my lips and making anything more than a muffled moan impossible.

My cock was still hard, but now throbbing and desperate. She took the scotch tape and wrapped a band of it at the base of my cock, tight enough to be painful. I tried to complain but it was impossible to make anything more than grunting sounds.

My cock was twitching now.

Hannah took the box of binder clips and one by one, added them to my cock, pinching fiercely. No matter how much it hurt, the tape band kept the blood trapped in my cock, forcing it to stay hard.

I tried screaming as she added more and more of the clips, feeling like dozens of bee stings on my cock.

The only exposed space was the head, now leaking copious amounts of pre-cum, which she started poking and scratching with thumbtacks.

"Still want to kiss me, David?" she teased?

I could feel tears welling up in my eyes. "I nodded," which made her laugh.

"That's a good boy," she said, in a patronizing tone that made me squirm even more.

She looked around the room and smiled. Picking up a framed certificate for "Teacher of the Year," she chuckled and placed it on my lap, behind my tortured cock.

She took out her phone and began snapping pictures as I squirmed frantically to try to hide myself.

She walked around behind me, placed her head on my shoulder and took a selfie of the two of us.

"Now I can really hurt you," she whispered in my ear.

One by one, she removed the binder clips, each one bringing a sharp, intense pain back into my cock as they were removed.

She she unwound the tape from the base of my cock, it quickly went limp, shrivelling up to a size even smaller than normal.

"See, there we are," she taunted, pressing the ruler against my abused cock.

"That isn't even two inches, David!" she said pretending to be shocked.

I groaned into my gag.

She picked up my journal and began to flip through it.

"You really did do a lot of writing, didn't you?"

I nodded.

"You know I am going to use everything you wrote against you, don't you?"

I nodded again.

"You knew that when you wrote it. I bet that was all you could think about, wasn't it? What dirty little secrets can I reveal? What embarrassing little fetishes? What things will make her laugh at me and humiliate me more? Didn't you?"

My mind raced back trying to remember the things I had written. The times when I was sure it was just a game and that I would never see her again.

The truth was, it had become something of a game to me, I would try to imagine my most embarrassing fantasy and then write it all down, imagining her reading it, trying to guess how she would respond. Over the weeks, it became more and more extreme, more and more revealing.

It had become unreal to me, a secret place for my most humiliating confessions. A silly pink notebook, covered in hearts that no one would ever see.

Until now.

She smiled more as she read and began reciting my words.

"When I think of Hannah, it takes me back to when I was in school and it makes me think of the all popular girls who w

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