Heh, I've actually pondered the 'drag' question. Drag for me would definitely be wearing a big masculine outfit... and I'd probably still be 50/50 nowadays. But I don't *want* to dress like a man. And I don't want to go to a drag show as female because it's *not drag* - and I don't want to be seen as a drag queen if somebody clocks me.
#1 is a great shot, you might consider replacing your avatar. Your brows and the curly hair are detriments, I think - but usually guys with curly hair like that are 'softer' men anyway.
For the dudes here, what do you see as the most feminine glasses? Not to hijack, but since it came up. I've put off getting a new pair for a long time because I cannot find the right frame at all.