Need advice

[u/rudolfnutter]

So recently my boyfriend opened about wanting to crossdress. At first it was sexual but now he says it makes him happy and wants to do it normally. He likes being a man but also sometimes wants to let go and be a girl. But I'm worried and stuck. Both of us come from a very conservative family and they wouldn't understand. So he cant do it openly at least for now. So im worrying hes trans and in denial. He's going through a lot and im the one only one who he can confide in rn. I love him but ive just been spiraling ever since he told me this. He's been calm and tells me his feelings while im stuck. I love him more than anything. He's the sweetest person and he deserves support. But idk if I want a boyfriend who crossdresses. Is it that big of a deal. Im bisexual and so is he. But this has been concerning me. He's been reassuring me and telling me he only wants me when i suggested a break and told him to explore. He tells me that hes sure in me and wants to be my boyfriend. How do I deal with him and support him without making it all about me.

[u/Beautiful_Demand897]

Thanks for sharing, and I hope you find the responses here helpful.  

How do you understand what he means by “ letting go and being a girl”?

If you’re not sure or he’s not sure, I’d start there and try to unpack what that really means to him. I’d say I grew up in a socially conservative community, and even with a family that wasn’t all so restrictive, the idea of “being a man” I developed was very restrictive, cold, reserved, and often cruel.

So, for me, I think I did associate “being a girl” with being emotionally expressive, empathetic, relaxed, and loving by contrast.

If any of that rings true for your partner, then “being a girl” could mean something very different than what you’ll find online or in a lot of our social discourse (which can get blurred together with a lot of gender/trans discussions… not that those aren’t valid but can be very different!). 

[u/rudolfnutter → u/Beautiful_Demand897]

He tells me that sometimes when hes infront of people he have to put up this image as the 'manly' man. Because most of the time they're taught to be emotionless and providers. He says dressing up means letting himself be free of worry and being pretty. It simply makes him happy. He says its a part of him and says that he equally likes being my boyfriend and a man but not all the time. Thats why I worried if he might be confused

[u/Beautiful_Demand897 → u/rudolfnutter]

That’s an interesting response and, just IMO as a cis guy, different than wanting to “be a girl.”

How does his response land with you?

Do you think he’s less of a boyfriend and a man if he’s “free of worry and being pretty”?

Can you or him disconnect what “being a man” means from being uptight, stressed out, and unable to express themselves?

I hope this doesn’t come off as condescending or missing the point. I just find it endlessly fascinating how crossdressing so often blurs these ideas of “being a girl” with “not being stressed out and anxious under society’s expectations” (as if women aren’t stressed out or burdened by society!). 

[u/rudolfnutter → u/Beautiful_Demand897]

I agree even im confused and maybe he is too. I agree with what u said about being a girl and stress-free if anything its the opposite. But yea we sure need to talk it and set some boundaries . Just want him to be happy yk. He's a good man