Why Should This Still Bother Me?

I am considering an affair because of regrets I have had all my life.

I was a virgin well into my twenties; shy and poor and having few social skills, but was working to turn that around. At my first real job out of school there was a cute redhead and I just did not know how to approach her for a date. To try and build confidence I had asked out a couple of girls I met but had been (kindly) rejected. That drove me back into my shell but I was still trying to get the courage to ask her.

Well, about that time a couple of buds, one from work, a long time friend, and I took a road trip to Toronto in my car. The guy from work was OK to hang out with but unreliable and not very good at his craft. Anyway on the way back this guy mentions to me that he took out the redhead and that she was a really good **** and went on about how good she was. That somebody who I was infatuated with would go out with and **** a weaselly player just left me crestfallen. Were we alone I felt that I would have beat him senseless and left him in a ditch. I did not, just kept going and never thought about asking out the redhead again. This still (even as I write) fills me with an incoherent bitterness.

A year later, I fell hard for the woman who is now my wife. She had more experience than I when she was young and that didn't matter to me anymore by that time. I have been faithful to her. Now, as her sex drive wanes I regret not trying out other women like other guys have done.  I feel deeply bitter about that, stemming from the incident I mentioned.  Companionship alone just does not cut it and an affair at my age is probably not in the cards, though I am thinking about actively seeking one. The alternative would be that as I feel sexually lonely why not just cut all strings and be really alone?

I dunno - any hope?
GTR1400 GTR1400
61-65, M
May 20, 2012