As a guy, female friend of mine liked my nails and wanted to paint them because she had a whole bag of nail polishes, she kept persisting until I let her on one hand to humor her but I actually liked it when she was done. Hid my hand in my pocket the whole way home though.
More embarrassing to think about is the next time we were riding, not remembering how I asked or how it led to it, I let her do it again with the same hand. Not again after that though because, well, you can see how it would be strange or how she might question if I liked it.
And it gets more embarrassing to mention, I’ve semi-cross-dressed before. With water-balloon boobs and a makeshift bra. Saying this gives me chills :s
(Strangely… Not the first time a girl has said they liked/wanted nails like mine, because it’s happened before in class from a different female classmate, but a stranger. She said she liked them and the other girl sitting across from us in our group of three tables just waited to see how I’d reply. When she saw I was trying to figure out how to reply to that without a plain “thanks!”, she told the girl how awkward that was to say hah.)