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I think he's a cross-dresser, I'm okay with that but how do I discuss it with him?

Tagged as: Big Questions, Dating<< Previous question   Next question >>
Question - (22 April 2012) 2 Answers - (Newest, 23 April 2012)
A female Canada age 51-59, *plashdown writes:

My Boyfriend and I have been living together for 5 yrs now . I discovered about 1 yr ago that he is a crossdresser , I'm almost sure he knows that I know and I think he is feeling guilty about this , I'm ok with him doing this and want him to be comfortable about expermenting , but am struggling with the question . Do I talk to him about this and tell him I'm alright about it or do I remain silent ??? , my feeling have not changed for him and I relly want us to continue to be together .

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A male reader, anonymous, writes (23 April 2012):

Simply be truthful! Being a cross-dresser myself, if you tell him you are ok with it, and would love to participate (help with make-up wardrobe)... he'll love you even more!

I wouldn’t recommend you just pull something you’ve found out, you’ll scare the hell out of him. It really depends on his demeanor. You could go shopping, and joke that a dress would look so cute on you…. Or cuter on him.

Hangout at home and watch “The Bird Cage”, or you could simply tell him the idea of a Cross dresser is really a turn on… and then admit you found such and such.

You will be better for telling him… but be sure you are ok with it!

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A female reader, Thisiscrazy Australia +, writes (23 April 2012):

Thisiscrazy agony auntIf your happy for him to express himself then let him know dont be someone he feels he has to hide from tell him your feelings havnt. Changed tell him you support him make him realize he can be free to be himself around you. Your relationship will be stronger for it and he will admire you so much for helping him be free to be himself.. Now to start this conversation don't tip toe be normal and say Hun are these your. I'd love to see them on you and take it from there if your nervous he will sense it and feel ashamed ...

Hope this helps

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