Guy #20 marked the first time I ever had sex in Canada. Toronto, to be precise.
All of my previous sexual experiences had taken place either in the closet or in a small country with only one gay club. Now I had arrived in a city big enough to have its very own gay village.
I spent the summer of 2009 in and around Downtown T.O., enjoying the thought of constantly being surrounded by millions, many of whom were gay guys.
It was a time of many firsts. Sexually speaking, I went supernova that summer.
For starters, the summer of 2009 introduced me to the world of Craigslist, where gay men gathered before the rise of Grindr:
“Looking for chubby bottoms”
“Reward for your dirt”
“Fun in your hotel room”
“Dad, I need a punishment”
Those were the kind of advertisements I shifted through in search of my Guy #20, who I first came to know as “Athletic Hot Bi Guy”.
Athletic Hot Bi Guy and I got in touch through Craigslist. We exchanged a few pictures, decided we were both doable and then set up a date at his place, a beautiful penthouse in Downtown Toronto overlooking the city skyline. The scenery might actually have been prettier than Guy #20 himself.
My first ever Craigslist date went like clockwork up until the moment I suddenly had to puke. And again. And again. And then once more. And a few more times after that. I lost count eventually.
I had never heard of roofies, or that people sometimes put roofies in other people’s drinks. I do remember thinking my wine had tasted funny that night.
It wasn’t until years after my date with Guy #20 that I finally realized he had pimped up my drink. At the time I figured I had drunk too much, even though one glass of alcohol had never made me sick before.
Apart from feeling unbelievably dizzy, weak and sick, I was very much ashamed of myself. No one likes to puke on a sex date. I was so busy being ashamed of constantly hovering my head above a toilet, I neglected to fully realize how calmly Guy #20 was taking all of it. He didn’t comfort me, nor did he get in any way upset or worried. He just kept sitting on his bed, athletic and hot, waiting for me to feel better.
Of course Guy #20 knew exactly what was going on. He was probably counting himself lucky I didn’t realize I had been such a good bottom because of a roofie.
Naturally, I wish it upon Guy #20 to end up in the Emergency Room with a vacuum cleaner stuck to his parts. The sad thing is he never even needed drugs to get me. Athletic Hot Bi Guy summed him up nicely. He was athletic and hot. That’s usually enough to get me high.
To my surprise, Guy #20 later contacted me to invite me a second time. At the time it highly surprised me all my puking hadn’t been a turn-off, but I guess in his mind it was a fair price for such a good bottom.
I however didn’t feel like being reminded of my shame, so I kindly ignored Guy #20’s invitation.
So, my first sexual experience in a big city ended in a modest drug overdose. Yet at the time I wasn’t aware of that. What impressed me most was how unworldly easy it was to obtain sex in a populated area. To me, Guy #20 marked the beginning of a new era: I had definitively left behind this shy, insecure and dorky figure who couldn’t get a girlfriend. That had been me, barely two years before.
After spending the night at Guy #20’s house, recuperating from what I still thought was bad alcohol, I walked down the streets of Toronto, feeling content and satisfied.
I knew I had a busy summer ahead of me.
LENGTH: One night
FORMAT: Sex date
SEX SCORE (0 = Windows Vista <–> 10 = The best sex ever): 6.5