A first

When it comes to writing a sex blog I face two major challenges every day. Number one is common to any blog/column: coming up with column ideas.

The second challenge is unique to my blog. How much information do I share? The blog isn’t anonymous, people that read it/follow it are generally people I know, people who are in my life and know the people in my life, so when I write about what’s going on in my life, it’s far more personal and intimate than your average blog.

This second challenge has stunted many of the ideas that got past the first challenge – not that I’m using that as an excuse for the lack of posts. I’m busy and lazy. Plus my life is complicated.

Anyway, this is all to let you know that the following information I am about to share is very personal to me. Obviously anything about sex is, but this more so because it’s a first.

As some of you may know my virginity story is not so storybook/movie-like. Nor is it a common tale of teenage experimentation. I was 18. He was 25. Met him at Cherry Lounge (remember that place!?) when he was filming a performance/show for MTV Canada. Delta hotel. His DJ was banging a chick in the bed next to us. The best part of it was Conan O’Brien was on and Sylvester Stallone was the guest. I’ve always wanted to go on Conan’s show and tell him about that (not sure what I would be on the show for…). I lost my virginity to a Canadian one hit wonder while watching Conan O’Brien. Yay me.

My romanticized version of my first time involves being with someone who if I wasn’t in a long term relationship with or in love, it would be at least someone who I trusted and was comfortable with. Someone who I knew well enough that it wouldn’t be weird and awkward later.

I imagined it would be a build up. You know, we’ll talk about it first sort of thing, get used to the idea. When the time came, I would be okay with it because I’ve known this time was coming for awhile. There’d be alcohol involved to get past some nerves. Maybe a few jokes, you know. Fingers would be used to explore the way. And then slowly it would begin. There’d be sharp intakes of breath, the occasional “are you okay?”, “are you sure?” and the breathless reply “yes” even if there is some doubt, pain and hesitation. The time has finally come, you’re not going to back out now. And just like the build up to it actually happening the pace would increase, the sharp breaths would become moans, the questions would cease as it became apparent that yes it was okay and yes I was sure. At one point it would become a little too much and I’d say stop. We’d take a break, smoke, talk. But not content to leave it at that, we’d try again, this time with a bottle of Astroglide nearby. The second attempt would be better, pleasure would be discovered, new positions would be explored.

In the aftermath of such intimacy and alcohol the conversation would be open and honest, thoughts would be shared. Finally content, tired, we’d fall asleep next to each other.

And that is what my first time taking it in the ass was like.