Reply To: When to tell a woman you’re dating that you’re a Crossdresser?

[Cece X]

I got back to dating a woman a year ago after two men over the previous six years. I struggled to work up the courage to tell her that I was bisexual and a crossdresser.
Probably on the fourth date I told her that my previous partners had been men. That did not go so well but she accepted, although she continues to raise concerns.
Perhaps on the fifth date, with me now particularly nervous due to her discomfort over my previous confession, I told her about my crossdressing. Actually, that went over very well.
A year later, we are very happy together. I am so glad that we got past the choking secrets early on. I believe this woman is a keeper, but if Ii ever court again, i will reveal by the third to fifth date.

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