If you asked me a year ago if I'd be spending most of my free time playing visual novels (a.k.a. eroge if you wish to be anal over it), I might have seriously considered laughing at you for asking such a ridiculous question.
But then for some reason or another either through sheer boredom or a simple whim (I can't remember which) I decided to play one so I could see what was so special about them, and the rest is history (except on TheTF.net where it's usually regarded as Nemmy going off on one about some bloody obscure Japanese thing again).
Thinking back, I believe the first one I played was Tsukihime. And I guess the reason for choosing it as my introductory VN was that I had already seen its anime adaptation, but never quite understood the whole 'there is no Tsukihime anime' standpoint from the fans.
After roughly a week or so, I had completed all of Tsukihime (which was incredibly awesome by the way) and got the Easter eggs too. I then advanced onto the Tsukihime PLUS+DISC and Kagetsu Tohya before I set my sights on another TYPE-MOON classic. That being Fate/stay night, a VN I'd been contemplating on trying ever since I watched the anime, and took a keen interest in the umpteen figures of Saber (notably Saber Alter) I've seen online.
Well, if we skip forward a bit from there, that'll take us to about the end of April and my completion of the Unlimited Blade Works route. At that time I was kinda vexed that I couldn't continue into the final route called Heavens Feel, as it was still in the early translation stages I think.
So, with nothing worthwhile to occupy my boredom (besides watching anime and toku) till mirror moon released their patch for Heavens Feel. I patiently passed the time by playing Melty Blood: Act Cadenza, and other VNs like ChaoS;HEAd, CLANNAD, Narcissu, One, planetarian and True Remembrance.
Although it should be shamefully noted that when the patch came out in November; I enjoyed so much, that I finished the entire route in less than a week! It also changed my opinion of Sakura Matou, who I always wrote off as annoying.
Nevertheless, once that epic piece of awesomeness was finished. I began seeking out other VNs for me to enjoy. And that's where Bible Black, Crescendo, Da Capo, Ever17, Kana ~Little Sister~, Princess Waltz, Saya no Uta, Snow Sakura, Wanko to Kurasou and Yumi Miru Kusuri come in.
I also attempted to play Fate/hollow ataraxia, Kanon, School Days and Tomoyo After. But I gave up cos they haven't been fully translated into English, and I'm not too fond of using the AGTH and ATLAS translation method.
Which finally brings us to where we are now, as I still need to finish off Utawarerumono, Discipline and Brass Restoration. However, I've gotten somewhat sidetracked recently in playing Umineko and Edelweiss.