Denim-on-Denim

Mission 1. Hook up with someone as old as my mom (54) and as young as my sister (20) in a month.
Mission 2. Live a completely gay lifestyle (without the gay sex) for a month.
Mission Three: Live without an apartment for a month.
Mission Four: Reconnect.

I was ill-prepared for the date. I was having a hard time with the word itself, "date." I am such a fucking cynic in this department, and I couldn’t even breathe the word without feeling like I was on the Brady Bunch. I knew I was going to fuck this up with the 19-year-old. I just knew it.

I had spoken to her on the phone, last week or so. It was one of those conversations where all I was trying to do was not forget her name. It was Samantha (I love setting attainable goals). She had a sweet phone voice, and from Jamie’s picture she looked good. I only saw her face in the shot, so I had to take the leap of faith that her body would suffice. Since she was a 19-year old dancer, I felt comfortable with my odds.

We originally set the date for Saturday. But, as the day encroached, I was starting to feel like this would be weird. I have nothing against young girls, but given our introduction through Val’s daughter, it felt a bit off. Saturday is such a traditional date night too, and carries a vibe of popcorn, movies and making out. I felt I was setting an unreal expectation, wrapping my thirty-year-old need for sex in a sugar-coated, date-night wrapper. I didn’t want romantic comedy and cuddling. I wanted decadent bathroom sex. The symbolic choice of Saturday night created disconnect in my head.

But I was being honest with myself. By virtue of her birthdate, just-legal girls like Samantha are sex dolls to guys 11 years their senior. They are a feather in our cap. A madcap moment of self-made lust, amplified only by our perception of their relative youth. Yea we are scum, but we inherited the world like that. And there’s a lot more that needs fixing than the medievel view of a hot, young piece of ass.

The more I thought about her, the more red flags I raised in my neurotic inner being. Why would this girl even want to date me, sight unseen. Perhaps Jamie gave her a report she approved of, but I’m 11 years older. I thought we were invisible to any girls under 27. I needed perspective. I needed to find out her motives, for my own were id-driven and sinister.

I’m not an expert on sex without strings. Being with only a handful of women has never allowed me to develop that side of my brain. But, luckily I have a few friends who have. Jim was the first that came to mind, by his mere numbers alone, but he’s an actor. Those guys don’t even have to work at it. Even Buscemi can probably get a Perfect 10 Model to rusty trombone him after stepping off a treadmill.

So I chose gay Daniel, not merely to help him manipulate more air time, but to find out the subtle nuances of the one-night stand, of which he has had a ton. I explained my questions, and he was more than happy to help, especially since he knew it would make it to the blog.

“Seriously, no more jokes, why would a hot 19-year old be interested in someone as old as me?” I asked.

“Maybe guys her age can’t make her cum,” he said.

“C’mon dude?”

“Seriously, some girls have a daddy thing. It’s a bit disturbing.”

“So, you think I’m her daddy?”

“No, Rob, God. But maybe there is some truth. Feel her out.”

“I don’t care if she thinks I’m her dad as long as she doesn’t tell me. I just need to know if I’m being a heel for making it a one-night stand? Should I be honest?”

“Rob, you can’t be a bad boy and a good boy in the same breath. If you want to fuck her, do it. But don’t expect her to be your friend. If you want a friend, don’t expect a handjob out of the deal.”

“I hate those anyway. They seem worthless. Anyway, why would I want this girl as a friend. Seriously. I just want someone to screw.”

“Now your talking my language. So what are you going to wear?”

“You know, I haven't even thought of it. Plus, I’m having second thoughts about going in the first place.”

"You bitch, you have to go. You can’t take someone’s Saturday night and then cancel. It’s a total dick move.”

“Yea, but I really think this could turn out bad. Maybe I’m overthinking it. But I don’t need shit from Shelfie and Tracy.”

“Euull, can you please stop talking about him?”

“Yea, you’ve got that thing...”

“…with the hair,” he said, disgustedly.

“Sorry."

“Anyhoots, back to the fashion. Hmmmm, you should wear the Kenneth Cole gunmetal shirt and the denim Varvatos blazer we got you.”

I have no pants to got with that. I haven’t worn it since. I can't even remember the last time I wore it. Anyway, like I said, I don't have any pants."

“Wear the black ones.”

“They’re dirty and I don’t feel like going in to the dry cleaner and having to talk to the short guy. It’s the counter thing.”

Yea, I know all about your counter thing. How about…Duh, fashion staple. Jeans. Just wear jeans. That would be so cute. Wear the ones that make your ass look good. But I would wear a white shirt, something contrasty.”

“I have no idea which pants make my ass look good. Anyway, it doesn’t matter, I’m still a bit leery about throwing down the denim-on-denim look. It seems too fucking boy band. I’m not comfortable with it."

“Oh, God Rob. Everyone’s doing it. Check out the fall lines for God’s sake and stay the fuck away from Old Navy. It’s ruining your fashion sense.”

“Listen, we’ve got a few days left. Maybe we can go find some pants. That blazer is the most expensive piece of fucking clothing I own and I only wore it twice. I fucking hate you for making me buy it.”

“Rob, if I had a dollar for every Gap shirt I gave to Goodwill with the tags still on, I’d be a millionaire. Fashion is fleeting. You need to let it go. But that blazer is super cute and it still is in season. We’ll find you some pants you’re comfortable with.”

“All right,” I said, "maybe tomorrow. I’ll call you. Let me get my other line."