My first cosplay was Limstella. It was a rather obscured cosplay as it was from Fire Emblem The Blazing Sword. I did my first crossdressing as Rhys from Fire Emblem Path of Radiance at my first summer UK convention at Ayacon Revolution in 2009. From there, I explored many anime and game characters, mainly tomboyish girls or teenage boys.
Falsetto from Eternal Sonata the most feminine outfit and broke my comfort zone. It was also the most difficult outfit so majority of the sewing the patterns together was from my mum. I thank her so much for helping me out for the past two years for making my outfits.
I prefer to go for characters who has short hair as long hair doesn't suit my face. Fact.
DeviantArt - http://bombomdubbie.deviantart.com/