I want to do it so bad! >.< Been quite the femboi for 15 years. :3 I'm so embarassed to go buy some clothes though. I was thinking of shopping way out of town or buying online. Perhaps rent a PO box or ship it to a center and pick it up there.
Buy them and if anyody asks say it's for *insert femal name of a person who doesn't really exist*'s birthday, but this may not work in a small town. Don't he hesitant or nervous about it.
May I add I'm 6'2". =p I guess guys have tall girlfriends though. Is that what you've done? There is also a bit of internal shame I have about it...like I would feel perverted or creepy while shopping for feminine attire. >.>
I borrow clothes off my girlfriend. I felt shameful just before I tried them on. It felt urprisingly nice once I actually put them on. Also I went window shopping with my girlfriend and it isn't that bad.
Don't just come out and ask them for clothes! Make sure it is somebody who would definitly be ok with it.