Conversations with a Cross-dresser

My biostats class is notorious for ridiculous problem sets and hard grading. The lab for the class gets out around 10 pm every week. Being the responsible student that I am, I stay the entire duration of lab, and consequently get out around 10pm. Whenever I do stay for lab, I get nervous about waiting at night for the bus to take me home. Luckily, there are usually students that wait for the same bus, so I have witnesses in case anything happens.

Unfortunately, I found myself completely alone at my bus stop around 10:30 last night. I'm not going to lie - I was a little scared. I then spotted what was either a prostitute or a man wearing a mini-skirt and heels walking towards the bus stop. I quickly realized that this woman was not a woman.

My first thought: "I hope this person doesn't rob me." Then I realized that there was no way someone wearing 4 inch heels he/she couldn't walk in would be able to run off with my wallet. Mr. Mini-Skirt sat at the stop and started smoking (thanks for polluting my air...). He then asked me if the bus was going to a particular stop, and explained his unique choice of clothing. Turns out, he was going to a early Halloween party and decided to dress as a woman. Or so he says.

The bus arrived, and the cross dresser sat down next to me. We vented about the pains of wearing heels, the annoyance of pantyhose, the difficulties of choosing the right color foundation, and how skirts do not provide any warmth in the cold. He asked what my name was, and I then asked for his name. He/she answered, "My name is Delicious. Or Candy Apple. I haven't decided yet."

While this man's inner woman was still choosing a name, his manly name was David.

Then David pulled out this pickup line: "I have to put on tons of make up to look even half as beautiful as you." And then he asked me to get drinks with him. Good thing I don't drink. And no, he did not get my number.

A few months ago, my friend Karen and I came up with (fake) lists for relationship "Deal Breakers"(think 30 Rock). Two of my "Deal Breakers" are that 1) the man was at one time a woman, or 2) that the man wants to be a woman (my list also included "Only exists on the internet site Second Life" and "Does not speak English" as Deal Breakers). When I came up with my list, I was completely kidding. I didn't think I would ever get hit on by a guy that fell into either of those categories.

What are the odds that, in a city as large as Boston, one of the few men to actually ask me on a date was wearing 4 inch heels and mascara?