2 min

Two virginities in one night

Like trying to insert a water balloon into a wine bottle

Escorts know that there is good money to be made in government towns.

So a couple of years ago, when I took a trip down to Victoria to visit with some friends, I decided to rent a hotel room and turn some tricks while I was there.

It seems the professional callboy is somewhat of a novelty to British Columbia’s capital city.

I put an ad up on Craigslist and, within a day, I had booked four clients over the two days that I had put aside to work. Of the four guys, three had never been with an escort before.

What’s more, it was the first time that two of them had ever been with a guy.

It’s pretty damn exhausting taking two virginities in one night. I’ve never worked so hard in a weekend, but I made a nice chunk of change, enough to cover my expenses for the trip and pay my rent.

All of this time later, though, I still think about one of the guys from that working holiday. He left unsatisfied, and my conscience isn’t letting it rest.

He was in his mid-20s and fairly cute, enough so that I wouldn’t have resisted his flirtations had I met him under different circumstances.

He was a recent university graduate, in the arts, and struggling to make ends meet. I got the sense that he’d be eating Kraft Dinner for a week after throwing down his $200 for his time with me, but as he said, it was his Christmas gift to himself — “a dream come true.”

Flattering to me, for sure, but the pressure was on to perform. He was my fourth client in two days, and I was really nervous about meeting his high expectations.

When we met that night, we had a definite rapport. I offered him a beer and had one myself to take the edge off our mutual anxiety.

His naivety was cute. He asked me if I was a cop. I’m pretty sure that only works in the States, but it only made me like him more.

He had probably the tightest asshole I’ve ever encountered. I wasn’t 100 percent, and so it was like trying to insert a water balloon into a wine bottle.

I wish I’d dealt with his disappointment better. As he departed, he took a last look at his stack of twenties left on the hotel table and, crestfallen, let out a sigh before he shut the door behind him.

That weekend I stretched myself too thin, and it became all about the money. Maybe I’m too much of a bleeding heart to be in business but, mate, if you’re reading this, I owe you a freebie.