Well In my case, I lost mine to a WG a few years back, mind you, I was 27 at that point of time and never had a girlfriend, simply because I was too involved with school/work/army to even bother with a girlfriend.
Not to mention i was terrified of ending up like several of my close friends who had been dating/married to the same girl for 10+ years by the time they were 27.
I was simply just curious to find out how I would perform with a real woman and just went into a brothel and picked a girl I liked and got started.
Unlike most of the guys here, I did plenty of research over the net for a reputable brothel, with a selection of WGs to my tastes.
I went over sober, but was quite worried I would explode the moment she touched me.... turns out it was quite the opposite.... all the years of wanking had desensitised my tool, and it took a good 3 hour session to get me off LOL.
Now that i'm older, but still single I still do not regret losing my virginity to a WG, it help built the courage I had to get laid over the past years.
I still do visit WGs on occasion, kinda tired of the chase and the game.... might end up buying a czech bride in future