The Cross-Dressing Navy Pilot

I met this guy on OKCupid and we had a long email exchange about Switzerland. Turns out we were there about the same time and just a yodel or two away across a valley in the Alps. It felt like a really strong connection. So we set up a lunch date and it was a fantastic first date!  He looked better in person than his photos. We ended the 5-hour date with a plan for me to drive up to his place from my home in southern Virginia. He lived near Dulles Airport outside D.C.  It was my suggestion.  My modus operandi is to see the guy's place first.  If he's a slob, doesn't have a dog, or has to many mementos of an ex around, I make a hasty exit.

(continued below)

The Second "First" Date

I arrived at his place to some great wine chilling and a couple of lovely salmon fillets marinating in the kitchen. He didn't have a dog but he also didn't have a shelf full of wedding photos of his ex-wife, either. He had video of his trips and hikes around the Murren/Wengen area of Switzerland which were fantastic and brought us even closer.

Then the bottom dropped out of my dream date.

We were cozy, maybe too cozy on the couch, which moved into the bedroom.  It was late but it was a given that I was staying, the buzz from the fine wine and great sex made us both mellow and very relaxed.  Then he said, "Do you know the difference between your public life, your private life and your secret life?"

I said I didn't think I had a secret life.

"We all do, just think about it for a few minutes.  I'll be right back." he said, getting out of bed and heading for what I thought was the kitchen.

Ten minutes went by and he still hadn't returned.  I "yodeled" out to him and then, like Dame Edna or maybe a taller, more masculine version of Tootsie, he swept into the bedroom, dressed up like a Sydney drag queen.   Everything except 3" false eyelashes and a Marie Antoinette wig.

"This is my secret life", he said.

I know my eyebrows shot somewhere up around my hairline.

"Can you handle a boyfriend who does this just for fun?  I'm not gay."

I told him I wasn't sure because I don't know why he did it, where he did this or when. was just weird.

He told me it just felt good. He loved the feel of expensive hosiery and stiletto heels. And it was fun to experiment with different kinds of makeup and wigs and see all the new kinds of looks he could create. I was blinking a lot trying to take all this in when he added, "And then sometimes I get all dressed up for the parties..."

"What parties?"

"The ones in Georgetown. There's usually a lot of politicians and other high-profile people there, doing the same thing. Would you be uncomfortable at one of those?"

I asked him what people did at these parties. Couldn't be straight up.

"Well, there's sometimes sex, too. I don't get into that, though."

"How do you go to these parties dressed in drag? Uber? Aren't you worried about someone outing you?"

"A woman friend and I go together, she's into male drag. No one recognizes us except the host. We have to check our cell phones at the door. She's also very, very high profile in D.C. so I can't tell you her name. She once suggested that I have a threesome with her and, um, ...her German Shepherd."

OK, enough. I rolled over on my side and stared out the window into the night, waiting for morning. And thinking I'd give it a few days, maybe a week or so before I logged back into OKCupid.

Richmond, VA