Day Six – Weirdest Fantasy

January 6th, 2011

Describe your weirdest/most interesting sexual fantasy.

I had a lot of trouble with the words “weird” and “most interesting” while considering this question. Thought about a variety of angles and scenes and potential fantasies. Discarded some for not being all that weird after all. Discarded others for having been written about before. Wondered what would be “most” interesting of all the thoughts in my head. Then I remembered my Monday post. It seems these first few are building on each other.

My best friends and I used to look at each other randomly and pose the question “Jack or Spot?” In fact, a few weeks back, I got that in a text from one of them for no apparent reason. My answer was always Spot. Spot Conlon, head of the Brooklyn newsies, in Disney’s live action musical about the newsboys strike of 1899. Shorter than Jack, more wiry, but tougher and more feared than any other newsie in the city. And those eyes, clear and sharp.

So, my weirdest fantasy that still persists to this day? Being Spot Conlon’s girlfriend come submissive. I didn’t know the latter term when I was young, but all the fantasies hinted at that type of interaction. A look from him and I would immediately still, unable to move under his gaze. A pointed finger and I would stand where he directed. Any order, I would immediately follow. If I did something wrong, he’d put me over his knee right there on the docks in front of everyone. Spanking me by hand, with a belt or with his cane until I sobbed. As I grew up, the fantasies turned more sexual. He’d take me off the dock, to a private room in the back of a warehouse to put me over his knee, so he could toss me down and fuck me afterward. Even then, we tended to have an audience, a few newsies would follow to listen and make sure I was being punished.

Perhaps the weirdest part of the fantasy when I was younger, I’d incorporate Star Trek, the newsies either being a holodeck program, or a favor from Q, taking me back in time.

My 30 Days of Kink

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