I remember I have posted once here, but hell, I'll say it again.
My first VN was Tsukihime, and my favorite VN ever, now and forever.
Mystic Eyes of Death Perception, the most powerful ability ever, given how you would use it.
Didn't realize it at the time, but I sure picked a fine one to start with. I still consider it head and shoulders above all the others I've read thus far. (Excluding Fate/Stay Night anyway. Those two are about equal)
In fact, I just got done playing through it again a few days back, and I can't stop praising it. There is a reason quite a few people place that one in their top five.
I think mine was The Sagara Family as well. At least one that I played all the routes. I know around the same time I was playing Do You Like Horny Bunnies? 1 and 2, but I didn't really get too into those.
I sorta went in the perfect fashion, and I'll never forget my experiences.
I started with Katawa Shoujo, where it was only filled with simple indie style drawings and a simple backing track for situations. The H-scenes were more romantic than erotic most of the time. Then I got into FSN with the full voicing of non-H-scenes followed by spectacular story telling and extremely in depth routes compared to the anime.
Then came G-senjou no Maou. I felt like I was stepping towards heaven. It started out simple and got so much more crazy along the way. I'll never forget the experience and journey I made to love VNs.
My First Eroge was Bible Black.
Needless to say, it kinda scarred me ha ha ha.
It wasn't bad, but there is some hardcore stuff in there and I was still a teenager at the time.
Well..scrathing from my memory i think it was Monster Girl Quest!(a bad way to start it i guess).Dont get me wrong im friggin fuckin love MGQ but as a first experience it just doesnt seem a good one since its monsters raping and or eating you alive but i regret evry single second that i loathed MGQ but since i dont like letting things half-assed when i keept playing it thorugh the end and now its one of my favs=)