. I'd take him shopping for his own things, in his own size, before he ruins all of my stuff. Then, I'd complete hi transformation with a full outfit, make-up, wig and heels and then take him out to the clubs with me.
i don't even know. i'd just ask what the hell he's doing, and i'd try to be understanding. but i would ask that he buy his own underwear if he wants to do that shit hahaha. i mean it wouldn't be a dealbreaker or anything. i wouldn't dump him. i'd just be confused.
Question life, and quite possibly his orientation, then go lesbian. If my boyfriend wants to wear women's clothing, then I minus well be dating an actual woman anyway. Ok now, lets be real though I'd be slightly disturbed and back away slowly. We could talk about it and try to work things out and if he's that determined to wear women's underwear we could go get him some in his size. Yes, deep down I'd still be shit loads of disturbed, but I can't let that get in the way with my relationship with him because he likes what he likes, and if you want things to work you have to set aside your differences and accept each others freaky flaws and all.
honestly its a deal breaker for me id question his sexuality even if its nothing to do with that for him. its just too much of a crossover and feminine thing to me and i wouldn't feel comfortable around him as a girlfriend. everyones allowed their boundaries right?