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February 16, 2011
Posted at 3:36 pm
Updated: February 16, 2011 - 4:48 pm

Here's the plan, Sam

I said yes to the date. But before I get into the particulars, I want to thank everyone who sent me emails with advice and encouragement. Interesting how they were all men but whatever.

Him: He's Jewish, which is good. I'm not religious but at least we'll have our culture in common. Handsome, athletic, pre-med, father is a surgeon. Nice personality. Manners. Cultured. I've sized him up as someone who'll keep his mouth shut if we do anything. Not overly aggressive, yet confident but a little shy, which is endearing. I think I can trust him to the point that I may have to be the aggressor, if I'm feeling it.

The Plans: Saturday evening. I'm going to meet him at his club for tennis. He's better than me and it'll be interesting to see if he takes it easy on me in order to curry favor. We're both competitive and I'll have more respect for him if he "brings it". I don't mind losing to a superior opponent.

We'll shower and change and go to Coral Gables for sushi. Says he knows a good place. We'll see. I'm particular about my sushi. I'm not going to trade shots with him and while I may have some sake, I'm going to stay sober. After that, we're going to Coconut Grove for the art show.

Now....the sex. I have no specific agenda. I'm not looking for a boyfriend or a relationship or marriage or anything at all beyond Saturday night. I don't know what the dating rules are and I don't care. I'm going to go with what feels good and right. If I freeze up, I freeze up. If I'm not sure about this and I don't have a particularly good time, I'll thank him, kiss him on the cheek and say goodnight. If I want to fuck him, I'm going to fuck him. Or something in between. I'm bringing a condom, just in case.

Remember: Outside of Frederick and those times with my father and my uncle, I've never had any physical sexual contact with any male in my entire life. This is a fucking experiment and only you and my shrink know what's going on here. And no, I'm not going to tell him anything about the incest, the pickups, Freddie and Bev or SOL. That would be nuts. "Oh by the way...I write porn on an international website." Not! LOL.

What am I getting myself into?

PS to Tom Land: I never left Tom, but if you want to talk about it, you have my email.