I wore women’s clothes over the next few weeks but found myself needing to get more out of this experiment after I took pictures in front of mirrors all over town. I wanted to probe how other people felt about me as a woman, especially men who were attracted to me. But I wasn’t as brave as Ben or as immune to rejection, so I figured the best way for me to find men to go out with as a woman was to look online. This was 2000, when there were no dating apps, not even social media, and I wasn’t aware of any chat rooms that catered to men looking to hook up with cross-dressers. But I’d heard that people connected through AOL, so I started an account. AOL ran an online bulletin board with a personals section, and there were other ads of the type I wanted to post.

I’d never placed an online ad before and didn’t know what to expect, but I figured there was no harm since my account was anonymous. I found myself typing a single line:

“Cute transvestite, 25, blond/blue, 5’6”, 120 lbs., looking for some fun.”

There was no way to include a picture with my ad, so I hit submit, turned off my computer, then took a cab home from my studio that night. I didn’t have a computer in my apartment, so the next time I checked AOL was when I got to work the following morning, hoping to have at least a few responses to choose from.

At first I thought there was a glitch, when the first set of messages downloaded and the subject lines filled the whole screen. But then another page downloaded, then another, then another. After my email finally stopped downloading, I counted nearly two hundred messages in all, and more kept coming as I began to read.

There were a bunch of single-line emails with a dick pic attached, but also earnest messages that launched into full descriptions of these men’s lives, often either prefaced or followed by something along the lines of “I’ve never done this before but I’ve been dreaming about it” or, for the veterans, a promise to “treat you like a lady.” Nearly all of them asked for a picture and either promised one of their own in exchange or apologized that they couldn’t send one out of discretion.