How to dress a girl to look like a boy?

So I'm bi and my girlfriend offered to let me dress her up as a total guy and take her out somewhere. What should I make her wear? My main concern is hiding the hips because she's close to flat already.


Most Helpful Girl

  • Try military cap (she can hide her hair if she's got long hair), baggy pair of jeans and a hoodie. That's pretty boyish.

    But if you are gay though, yeah, I agree with gravy girl, do what she said or you'll hurt the girl.

    • ^_^ Thanks! I sometimes dress kinda boyish (black punk hoodie with skinny jeans + cap) but then I am mostly a fashionista. ie. cute purse, hair all done up lol....^_^ *,*)>

Have an opinion?

What Girls Said 2

  • So you're actually gay, right? And you're just trying to turn your girlfriend into something closer to what you really want? If so, cut her loose and go for guys. Don't be cruel to the girl.

    • I didn't suggest the idea at all actually. she brought it up and thought it would be fun. I love the open mindedness of this site. tolerant of everyone as long as you're fine with being called gay in every question.

    • Show All
    • Eh I'm pretty sure I'm attracted to women. if anything it's weird. I'm not attracted to guys themselves oddly enough. I'm attracted to their dicks if that makes sense. I can't tell if a guy is attractive but I love the idea of giving head. If that makes sense...

    • That's a pretty common theme... sexually intrigued by the idea of a penis, but yet not wanting a gay relationship. There's a lot of conversation about that in the forums at Literotica.

      As long as you are up-front with her about this it should be fine... as long as you don't cheat on her to go after one of those penises! Get her a realistic strap on instead ;)

  • Boyfriend jeans. They are actually women's jeans but cut in a guy-ish way



What Guys Said 1

  • Oh... and they sell these things that you put in your underwear to look like a flaccid penis. They are very realistic.. but not cheap, and you're talking about one night out, so I guess a rolled up sock will do it for less.

    And this was nearly a year ago, so I guess you already had that special date!