The Enviable Dater

After the events of the small-town gay bar my life went back to normal mediocracy. Nothing really happened I saw the guy I had kissed in my lecture a few times but never really said anything. I think a part of me was scared of the realization I was coming to. One day however, the guy we referred to as 'The Chest' came up to me in the hallway after lecture  wearing his signature extra-deep V and said "I'm not going home for Thanksgiving, do you want to do something this weekend?". I agreed probably too quickly and too enthusiastically and we exchanged phone numbers planning to meet that Saturday. I had never done anything like this, I was bouncing with excitement as I met my friends and told them I was going on my first "real" date. The another realization came over me, What if he thought we were going to have sex? I then got nervous. I didn't know what I was doing, I hadn't really done anything with anyone, and by the look of the bulge in his j...

Usually, click-bait titles bother me but when it's for my own personal gain I've decided I don't mind it. Looking at the title of this post you probably think I am going to tell you about losing my virginity. But that’s just the tip (pun intended) of what I’m going to talk about. What I am going to talk about in this post is my first kiss, first relationship, the first time I truly committed to something and I guess my first time. But let’s start with my first kiss.  As I’ve said before I was a bit of a late bloomer. After growing up in a strictly religious family I found myself at the age of 21 having never kissed a guy and in the middle of a bit of a quarter-life crisis. I didn’t know who I was, or who I wanted to be and after 3 years living away from my parents, I had moved back home to finish university. This was frustrating, to say the least. So I did the logical thing anyone would do, I lived out my rebellious youth at an older age. A little less rebellious c...

I'm not sure if I've mentioned it but I live in a relatively small city (pop. 58, 220). With that 'small town' appeal comes a small community of gays which I call my dating pool. It's the kind of place where every gay knows everyone else and the six degrees of separation turns into two. Earlier this summer I experienced just how small my dating pool was. I'm usually the type of guy that when I really start to like someone I limit myself to only dating them. Earlier in the summer I was enjoying the life of a casual dater and I had narrowed my prospects down to two guys. These two guys were pretty much opposites, the only thing they had in common was they were both tall. One guy was Outdoorsy, he worked as a roofer was muscular bearded your dream Canadian Lumbersexual. The other guy was materialistic, stylish, metrosexual, worked in retail and always looked perfectly put together but also casual. I had been on a two dates with both of these guys and wasn...