So here is goes. I do a lot of accounting/computer work for my boss on his home computer, and while searching for a file I downloaded I came across some gay porn. This peaked my interest, so I looked though his computer history (shady I know, but I need to know what I was getting into) and I'm glad I did. He had a couple searches in the m4m section of craigslist, and he has been meeting with an escort which he pays, although I'm not sure how far they go or how often. He is closeted as far as I know, as well as myself.
Here's the deal. I am 21 and have never been with another guy, but I really want to and I feel like this is the perfect opportunity. He is 53, bear type which I am attracted to. I am not really attracted to guys my own age, and have always been to afraid to meet a random hook up from a4a or craigslist. The positives are that I'm sure he is discreet, which I would like as well because alot of people I know know him as well, and I am not ready to come out. This is actually like the first time I have actually been about to do something with another guy. However, some of my concerns are how safe he plays with his other hook ups (from what I saw, it was only the one guy for the past few months) and how it will affect my job. I am not looking for a relationship, I would really just like to try stuff with a guy and see where it goes. Fwb would be what I;m looking for if I do enjoy it, if I go through with it.
Anyone have any advice whether or not I should try something? How should I go about it? Any advice is greatly appreciated!