Ask Dan & Jennifer

This one's going to be iffy.

I would get a girl, then get her used to who you are.
Then slowly hint to her what you do.
She may enjoy it after she gets to know you she may not. It's going to depend on who the girl is.

I think it has a lot to do with how old she is, how much she knows about sex, and how much experience has. And of course how open-minded she is about something like that.

I've been on the other side of it, and I'm not proud of how I responded to my boyfriend (at the time). It would've been nice for him to have eased me into the idea. It was a big shock to me and I freaked out. I had a lot of questions but he couldn't answer them because he wasn't sure about it himself.

So it would have been helpful to ease me into the idea. But that's just for me, I don't know about other women. Other women may be fine with it from the start, maybe the relationship is strong and you're both comfortable with each other.

Hope some of this helps you :)

Its really going to depend on the woman and how open minded she is. Depending on how fast you get to know one another you will be able to tell how open minded she is about things. First thing is dont make it a big deal, tell them early in the relationship, not the first date but after you have gotten to know one another and feel comfortable with one another, and be honest. Dont think you have to tell her everything right away, be vague at first to feel her out. If she seems receptive than go forward with telling her or showing her more. If she wants to ask questions after that, then answer, be prepared to have a discussion. If she is ok with it dont make it the focus of your bedroom activities. If your into wearing during sex, you dont have to do it every single time. Mix things up. And most important of all, if you tell your partner, and she's ok with it, do what you can to keep her happy. Main thing is to keep it simple, and introduce her to it slowly. Approach her when she is in a good mood or turned on. Talk to her about it a little at a time. Don't throw your whole crossdressing history at her if she hasn't asked about it yet. The main thing also is don't be nervous about telling her, be confident and calm. Many woman do accept, understand and encourage there man to crossdress once they find out he likes to crossdress. My wife and I have talked with many other crossdressing couples and the woman all seem to agree that honestly, being upfront and answering all questions and concerns helped them to understand it and be ok with it. And once they were ok with it there relationship was much more healthy. Hiding that you crossdress is very stressful and can cause issues in your relationship and its such a huge weight lifted off your shoulders when your partner knows. Check out our profile for more about us.