Technically, I took out women, as friends, in 2002, so if I were going to really look at it, I started dealing with a couple of girls that way when I was 26 years old and had some limited interactions as a tutor, working as a telemarketer (there was a black girl who was sending clear buying signals but I didn't respond with her), and just feel I was just out of synch. This was after I went to University (1995-2000) where I ended up after University without a girlfriend, or without any experience. It was tempting at the time to have used an escort as I had the drive and allot of credit card money (ie for a 20 year old), but I wasted the money in the stock-market instead.
When I was 30 years old, I had a nasty infatuation with a girl I met from the internet. To make a long story short she was the gal who went with the 'chad-player' and then cried about being pumped and dump while I got in such a jealous rage after reading that that I just lost my mind and killed that friendship. I felt too friendzoned by her while she did that with me (April - September 2006) I met a black lady off an incel-site (April - November, 2006/ back in 2006 incel was more co-ed than a male-only club) and she while we watched movies together, I didn't pursue or respond with her sexually because of religious reasons. She eventually got a male escort and I lost interest with her after I found out she went there. I had my first kissing experience with an 18 year old black girl (December, 2006 & November 2008)) and I met a collage age Nigerian girl (December, 2006 - September 2007) off the internet who was a virgin and into the choir. We dated a bit here and there but she wanted me to be more with it with fashion, etc... We had some french kissing make-out sessions and she encouraged me to grab her hips while french kissing her. So I felt that this experience with her made up for the crushing infatuation and betrayal of trust from the previous girl I was infatuated about and felt sore for a bit of time afterwards (ie it wasn't until 2012 that I met someone else that that was finally flushed out of my system).
At the end of that, I didn't feel like a loser as my ego was saved by the black women I subsequently met who were more patient and understanding with me and where I had my first type of intimate experience with. So this is a span between 2002-2008. Not sure if, or how that could help you. I did try out an adult site to meet women for casual sex, but I chickened out at the last minute of a planned "hook-up" and I wasted about a month to get there (had a profile crying virgin at the time), and felt I wasted a month to have killed a few hook-up opportunities, etc....