My journey is similar to yours, except during the days of print I found in Screw Magazine that were usually for NYC / NJ based Mistresses and actually spoke to a couple on the phone. Like you I was always drawn to powerful women, usually my age or older. I was 20 when I had my first session with legendary Belle De Jour who got me aroused just speaking to her on the phone. Belle ruined me too, in ways I won't explain here. I was so in lust that for a week or two so after the first session I'd call in between college classes just to hear her voice or talk with her for a minute or two. Eventually she said, "Get your ass over here and help me train a new Mistress!" I could hardly afford the first session with Belle, but she allowed me to serve as a discounted rate just for her. Soon after I was a "Roman bath slave" (house slave) once at her apartment and years later was used a couple more times to help "train" new Mistresses. I left and entered the scene over the years, but during the '80s and '90s whenever I came back I always contacted Belle. She was at least 25 years older than me, but she seemed to like and trust this lucky sub and I felt the same about her. I wouldn't say she considered me a friend, maybe a trusted friendly client.
I made the mistake of having a relationship from someone I served, and for awhile the highs were tremendous, but it ended badly. In recent years I reconnected with a now under-the-radar Mistress who knows me very well, we are friendly and confide in each other. Not a relationship, but at this point of my life if she completely retires I will too.