The One That I Let Get Away & Regret…

When I was living in Toronto, I wasn’t far from the movie theatre so one night, I decide to go on my own to the theatre. I didn’t have a car so I walked. Watched the movie then started making my way back home on foot. A bit into the walk home, there was this dude walking in front of me and I must have been walking faster than he was since I caught up to him so in no time, I was next to him walking. I say “hi, how are you” and he replies “fine how about you?”, the dude was pretty cute, younger than I was, scruffy beard, but looked hot to me anyway. We start talking and I happen to mention that I’m gay. He replied “I’ve always wanted to try that but never did” and we kind of left it at that. He was on his way to the Subway Station which was further than my place so I knew we would be walking together until I got home. When approaching home, he asked if he could come in and he said he was interested in having sex. I was living with a roommate at the time and was sleeping in the living room so I explained the situation to him and he was fine with that but I ended up not inviting him up because of the roommate thing and even today sometimes I think back and think “was I crazy… random hookup like that and I let it slide through my fingers”… needless to say when I got home that night I laid in my bed and I must have jerked off 3 times in a row just thinking about “what if…”