I'll write some memories from my very 1st RP-playthrough which was in 2007. I haven't played the game afterwards since 2008 until January 2012 when I returned to Oblivion.
I wasn't aware of these forums at that time...my first character which I consider to be roleplayed was a Breton mage / warrior Amadee although he mostly developed as a warrior instead of mage. Anyway, some memories:
-how I read The Immortal blood for the very 1st time outside the Vilverin and got very scared - not only it was a book about vampires, there was also a garlic outisde a tent and I was afraid to sleep outside. Still I couldn't resist and spent a night there. When suddenly something woke me up, I was sure these must be vampires (mind at that time I didn't know if vampires even exist in a game or no!). Luckily I was in a sneak mode, so a man in blue robe didn't notice me. As it turned out, it was a simple conjurer.
-a message that my deeds were observed by forces unknown...
...I looked around everywhere but couldn't find any witnesses but then I went to sleep and you know the story from here...
-I found a Mythic dawn robe and hood really cool and it was Amadee's favorite apparel for a very long time until he found out that he'll need some armor.
-wielding a cutlass in a computer game for the 1st time
probably the best memory because I collected cutlasses IRL for some time.
-OB was my 1st game where I could rent a room in an inn, so a feeling when I actually slept in an inn in a computer game was great.