When [M] living with a [F]emale roommate turns into an affair

*****Warning.. Long.. bit of backstory, skip to the asterisks for the fun stuff****

I have read a lot of the stories on here, and enjoy most of them. The roommate ones always take me back and have me thinking about, ….We’ll call her Bri. This story dates back to several years ago back when I was a junior in college.

I was a shy guy in college, and pretty terrible at hitting on women. I grew up with brothers, so conversations with lady folks wasn’t exactly my forte. Usually the only female friends I had were girlfriends or acquaintances of my guy friends. These were also the only women I was able to completely be myself around, and that was an entirely different person from the guy that was first meeting a woman. It’s not that I’m unattractive. I was just a late bloomer, and getting over the insecurities that come with that, take a bit. Over time, I’d finally get comfortable and start coming out my shell, and I often found these girls becoming attracted to me. Me being a horny 19-20 year old shit head, I sometimes took advantage of those situations. What can I say… It was hard not to be a terrible person back then, and I often found myself reciprocating the attraction. One such girl was the aforementioned Bri. Bri and I met through a buddy of mine freshman year of college. My buddy was much better at first impressions, and had made close friends with some stoner girls on his dorm room floor. 3 cuties. I being the shy kid probably said all of about 3 words to them the first several times meeting them. We’d get high together and I’d sit on the couch giggling. Those initial days turned into months as I slowly came out of my shell. Those months turned to years, and I still keep in relatively close contact with all of them 20 years later.