Dom and I were discussing once again our experiences when we first explored being gay. It was interesting how our experiences contrasted. Dom always reported auditioning a cast of 1000's before we finally crossed paths. My casting number was much lower. If I think about it, I may have had a cast of 100's if I was lucky. I did blog over the years about some of that cast.
Part of it of course has to do with physicality. Dom was a taller, beefier guy at that time with an incredible body. He has old pics of himself wearing tight leather clothes with his bare chest and abs open. When he lived in San Francisco, he talked about walking down Castro and being picked up by other guys.
I was a "skinny-fat" gay guy when I was first exploring my attraction. I rarely socialized and relied more on social sites like Adam4Adam, Bear411, SilverDaddy, and Craigslist to try and meet guys. And because of my physicality, I had a more challenging time trying to find guys that were into me.
Race no doubt played a part in it as well. Even though Dom disagrees with me (which when you never had any challenges with meeting guys, how would you know), his being white made it easier to find other guys when that itch hit. Being black I feel made it harder for me to find connections. There are a lot of discussions from other gay black men about their experiences in trying to hook up as well as the racism received from white gays.
What didn't help me as well was when I started exploring my gay side way back in 2002, I found myself living in a townhouse in the Chicago suburbs. I moved in the Chicago burb of Des Plaines, IL in 1997 and found myself working in another burb of Chicago. My former work colleague Stan was very much into real estate. He was always touting about the importance of home ownership in building equity. He owned several small apartment buildings and homes that he was collecting rent from.
He encouraged me to buy a home since I was planning to stay in the area for at least 5 years. Of course I wanted to live somewhere that was near my job. What I didn't consider was that Stan himself was married with a young child at the time and another on the way a few years later. I was single and prior to 2002, never had sex with anyone, man or woman. I was in my mid-20's when it probably made since to live in the city proper and in an apartment so I could have the flexibility to move when better opportunities came along.
Instead I wound up buying a townhouse in 2000. Ironically I wound up living in the same burb that Stan and his family lived at. I found myself being the only black and later gay guy on the block. My nearest neighbors were relatively nice but I couldn't help but feel out of place there. I was never really happy.
So I first decided to explore my gay side in 2002. I had broken up with the one and only girlfriend I had. I was getting used to the social sites. I decided for some reason that my first time would need to be with an escort. I found a muscular Hungarian guy living in the Lakeview neighborhood of Chicago. I believe we agreed on $150 for our sexual liaison. The plan was to meet on Halloween 2002.
So I found myself leaving my suburban townhome sometime at 11pm and making the 40 minute or so trek to Lakeview. Along the way I drove down Irving Park street and couldn't help but notice random folks parading the street in various costumes.
I remember having a hard time finding parking (that's anytime driving in Chicago). I ended up parking in a small lot around Lake Shore Drive and walking the few blocks to HG's apartment. To say I was nervous was an understatement. I was also excited as I anticipated finally losing my virginity.
I vaguely remember HG and I conversing and him expressing disbelief that I was using him as my first experience. I remember he offered me orange juice. That may not have been wise but thankfully I wasn't drugged...LOL. Then he led me to his lair. I remember us making out and him later using his body to pin me on the bed as he inserted his manhood and fucked me proper. After we got off, he made it a point to say that we weren't done. We briefly rested before he started fucking me again.
I remember being very satisfied. We talked for a bit but I could tell that the time to leave was getting near. But nonetheless that was my introduction to the gay experience. I knew then and there, I would not be going back to women. Not that I really was with any women.
I remember I had a few other escorts over the years that came to my home. But aside from escorts, trying to meet guys to date was especially challenging. If they lived in Chicago, you could forget about it. One thing about being in Chicago, there are a lot more options out there. The majority of the guys in the burbs I found were married or partnered which given the cookie cutter homes that were designed for families, made sense.
It wouldn't be until 2006 when I would finally have my first boyfriend in Rock. I've blogged about him a lot in my old blogger. He lived in Rockford, IL (hence his nickname Rock) and we managed to last almost two years before I called it quits. It wasn't the perfect relationship (what is) but it was nice to experience having an actual boyfriend. I definitely appreciate that time in my life looking back.
So I was completely out of place in my suburban townhome. I can say I was never really comfortable or happy there. I was happy when I finally moved out of there after living there 16 years. I barely broke even when I sold the house. I had refinanced in the mid 2000's and took out about $20000 in cash that I was hoping to make a good investment on. I wasted it on stupid penny stocks which wound up going south. Thankfully my selling price was $37000 higher than my purchase price and covered the loan as well as the cost of fixing the home to put on the market. I will say I felt like I left there just in the nick of time before Orange started his first term in 2017.
But yeah life is so interesting. There were some crazy as well as good times. Everything I went through led me to where I am today so I wouldn't trade a thing.
