I Dressed Up Like a Girl On Halloween

Well this time it's not me, it's my grandson. I had to share this picture of him, he looks so cute.
I'm so jealous that at his age I didn't tell my mom I wanted to dress like a girl for Halloween. I think I was afraid my mom and dad would see how much I enjoyed it and I don't think I would ever have wanted to take it off. Then again that may have been a good thing to get it out in the open how much I wanted to be a girl.
I'm so excited about my grandsons interest in at least having a curiosity about what it feels like to dress as a girl. I haven't talked to him yet about why he wanted to dress as a girl and find out if he had fun doing it.
It would be exciting to know if he was just like his grandpa.

gilliian

I can't say I live a very masculine life now actually, except having to use the gents toilet or carry the occasional heavy object. But I would like to do it in a dress personally. Also, I don't know if I really understood what I was doing at the time. I just know I felt more comfortable as a girl. I've just recently come to terms with it even though I've been doing it for 30 years. I'd always been insecure or thought it was wrong. Well...it was right for me, but wrong in everybody else's eyes. I don't know if I would come out even now though. But I'm happy living my gender-fluid/effeminate life, albeit in the closet.

gilliian

Oh, when I'm dressed, I am completely female. That's the thing about me. I'm very effeminate to begin with. So when I do dress up, it's not too much of a shift or mission to be feminine.

funtime51

he looks such a cutie dressed like a girl. hope he enjoys it and goes on to be a bit more adventurous :) maybe if he knew you dressed up you could help him choose some nice outfits and ideas