I’m Theo Calhoun. Ask me anything.

Note: These “Ask me anything” posts (inspired by Reddit) are created when I post as a character and invite other group members to ask questions.


Q: Hey, Theo. What’s the stupidest way you’ve ever gotten a spanking?

A: Um… wow, there’s so many I could pick. I think, though, it was probably the time I was being really difficult, and he said, “Young man, would you like a spanking?” and like an idiot, I said, “Oh, yes, please!”  …Yeah, that was pretty stupid.

Q: Theo, where is the strangest place you’ve ever been spanked?

A: Depends on if you mean properly spanked, I guess, with the pants down and everything. That really only ever happens at home, usually on the couch. But Quint’s not afraid to give me a few swats in public if there’s no one looking, and the strangest place that’s ever happened was probably a subway platform. There actually were other people around, but he pulled me behind a staircase, and the sound of a train passing drowned it out enough that I don’t think anyone noticed. Didn’t stop me from blushing like a fire hydrant, mind you.

Q: Theo, have you ever felt you were unfairly disciplined?

A: At the beginning? Plenty of times. That’s why I get sent to the corner beforehand a lot. Usually I come around to Quint’s way of thinking pretty quickly though, haha. I can’t remember a time that seems unfair looking back on it.

Q: What is your most memorable moment with Quint?

A: It’s going to sound sappy, but our first official night together, which was New Year’s Eve. I still remember every second of it, but the kiss at midnight in particular. Pure magic.

Q:  Hi, Theo, where was the strangest place you had sex?

A: I’m tempted to cheat on this one, because I’m assuming you meant sex with Quint, but he’s not all that adventurous in terms of location. Well, we’ve had pretty intense make-out sessions in the kitchen on occasion….

Before Quint, though, there was this one time really late at night in the dorm laundry room at NYU, with one of my RAs. I’ve never told Quint that story, now that I think about it. Hmm.

Q: Hey, Theo. Where was the strangest place in public you got a spanking?

A: Stranger than a subway platform? Hmm…. Actually… I can’t believe I forgot this one! It was the first time Quint ever swatted me in public.

Okay, we were at Coney Island, like, a month after we started the discipline? And I was still testing the boundaries a lot, so I kept pushing him on stuff. I think I was being worse than usual that day because on some level I wanted to see what he’d do in public, which seems awful, looking back on it. Ugh, what a brat I was.

But anyway, he wanted us to go eat something, and I wanted to swim longer. I whined and pleaded, and yet I still found myself in the changing rooms. He was trying to distract me, I think, by asking if I wanted to get a Nathan’s hot dog, and I made some remark about ‘what does it matter, you’re probably going to follow that stupid old-wives tale and keep me out of the water for thirty minutes after anyway!’

Yeah, I was… ugh again.

So he pulled me into one of the changing stalls, put my nose in a corner, and very quietly said, “Stand there until you’ve curbed the attitude, young man.”

And I turned around.

I think he was kind of surprised, because he let me get most of the way through a sentence about how I couldn’t possibly be expected to do this in a changing room. He’d be a lot quicker than that now.

He spun me back to the corner, swatted me four times, and then planted himself right behind me, so I could feel him breathing on my neck. Did I mention I was wearing wet swim trunks? It fricking STUNG.

So yeah, changing room on Coney Island. I think that beats the subway platform.

Q: Do you have a special room where the spanking takes place?

A: The living room on the couch, if it’s something where we need to have a discussion beforehand. If it’s more of a “stop that now” thing, wherever we happen to be.

Q:  What is your favorite way to make love?

A: I like to be on my stomach, so I can feel him pressed against me from head to toe. It makes me feel safe. Also, sometimes he bites my shoulder, which is always fun. 😉

Q: Have you ever asked for a spanking?  To relieve guilt or for atonement or because you were stressed out?

A: Not directly? There’s been a few times where I knew confessing something would likely lead there, and I went ahead and told him because the guilt was so bad, but I didn’t suggest what Quint should do.

And on a few other occasions, he decided I didn’t need a spanking, and I thought I did, so I kind of did other stuff to provoke it without really meaning to.

Q: What was the worst spanking you’ve ever received?

A: It was after the one and only time I broke a pretty serious promise to him. He used his belt, but that’s not why it was the worst. It was because I felt so horrible about it. I might tell that story someday.

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