She wears my stuff all the time but I'm concerned about her giving me weird looks or worse, dumping me for being 'gay' or whatever if I ask about wearing one of her dresses. So yeah, I could really use some help.
Most Helpful Girl
Are your sizes compatible? Would her things and dresses fit you? If so, talk with her about it and explain your desires. Tell her that you've always been "curious" about what it is like to wear a dress or other female things and see if she won't try and help you out. If you're a lot bigger than her, than the two of you need to go shopping together, so she can help you pick out things in your size. Cross dressing isn't gay, but it's a little different for some folks. I've known tons of "manly" types of hetero men that enjoy wearing one kind of feminine attire or another. Some enjoy the full transformation, with wigs and makeup. Kind of cute, if you ask me.3
Most Helpful Guy
HA GAYYYY! just kidding man, just ask, the worst she could do is laugh and say no. Or she might be all in, who knows. JUST ASK!2