Key West Vacation—Day 1

My alarm went off at 4:45, and I pulled into Joe’s at a little after 5:30. There was just a very short line at U.S. Airways, and after check-in, we walked down to the Southwest end to go through security.

Our short flight to Charlotte was uneventful. We had about an hour layover there, and while we were sitting at the gate waiting for the flight to Key West, I read Joe a passage out of the book I’m reading, Made to Stick, while he held his Blackberry in his hand. At the end of it, he started laughing and said, pointing to the couple sitting across from us, “That’s us in a mirror.”


One reading, the other on the PDA.


Our dream was to be enjoying a Bloody Mary by noon, but it wasn’t to be. We hopped into an “over-sized” taxi, by which I mean a van—one that we not so much chose as it chose us, being the next available one in the line. The driver pulled away, and then said, “There’s a lot of people waiting, I’m going to circle around and pick up another party. It’ll be quick guys, and I’ll let you off first. We were annoyed that he didn’t mention this little tidbit before taking us in.

We did indeed circle around and picked up not one, but two more couples, straight people—they’re everywhere down here, but they seemed nice enough. After dropping off both of those couples first—at different hotels—missy dropped us off. Annoying as fuck, and made us ten minutes late for our Bloody Marys poolside.


I actually lay out on the deck for about 40 minutes, 20 minutes at a time with a break between them, being careful not to get burned. Later in the afternoon, we met David from Pittsburgh Philadelphia, and the three of us enjoyed the Happy Hour here at the guest house, which runs from 5:30-7:00.

It’s a killer Happy Hour, because all of the well drinks (house booze, not top shelf) and all of the domestic beer is free. They keep a tab for you, and just zero out the total at the end, so you can leave an appropriate tip. I love that about this place.

Also sweet, is that the bar is poolside, and since it’s a clothing-optional place, there usually an ample (double-entendre intended) amount of eye candy about.


Later in the evening, David joined us to our standard two bars, first stopping at Bourbon Street Pub, where we got sucked into the drama of Heather and John and a couple with them. At first we thought John was with Heather, and that he was straight, but within minutes, it was obvious there was nothing straight about John. We think that other two people were a straight couple.

Their little group was pretty shit-faced, and Heather went into a long story of their drive down here to Key West, which involved them being robbed on the way. Someone mentioned blowjobs (the drink, a.k.a. cowboy cums and buttery nipples), and the next thing you know Heather was buying a round of 7 blowjobs.

Drunk. Drunk. Drunk. Who else buys a round of shots for strangers after being robbed earlier in the day?

She turned around with the drinks to start handing them out, and frowning and slurring said, “Who the hell are all these people?” as if we had all just appeared for free liquor. Uhm, we would be the people you’ve been talking to for the last 20 minutes, none of whom asked you to buy us drinks.


Shortly after that, we stumbled across the street to 801 Bourbon Bar, where we saw a drag show that wasn’t very good, and where we consumed an inordinate amount of alcohol.

On the way home we stopped for a slice of pizza at Pizza Joe’s—”Everybody goes to Pizza Joe’s,” where I had a slice of pineapple and ham, David had a plain slice, and Joe had the meat lovers.

We stumbled our all our asses back the Island House.

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