I’ve been seeing a new woman for about 4 months and things are going really well. The only thing is that I have a secret that I’m really afraid to tell her. The secret is that I’ve been a cross dresser for about 10 years. My marriage broke down 7 years ago and a lot of it was down to my cross dressing. My wife was against it and although I hid it for a while, I just wanted to be free to be myself. In the last 7 years I’ve dated a bit, but not ever felt like I do about this new woman. Should I tell her? If so, when would be a good time? I don’t want to scare her off.
Thank you for your email. I’m sorry to hear that your marriage didn’t survive, but it’s wonderful that you were true to yourself. It can be quite debilitating to have to hide our true selves from the world and especially from our loved ones.
It sounds to me like you’ve got the opportunity for a fresh start with this new woman you’re seeing. I would suggest you invite her round, share a meal and then talk to her about your cross dressing. No need to make a big deal out of it, you’re not doing anything wrong. Just tell her a bit about it, what you like about it and how it makes you feel. Help her to understand what it means to you and why it’s an important part of who you are.
If she responds well, that’s great! If she is unsure, wants more information or just some time to see how she feels, that’s fine too. Ask her if there’s anything you can do and give her plenty of time and space. Be available for her to ask you questions. If she has any kind of negative response, be as patient as you can. She might just not understand what it means for your relationship. Talk to her, be compassionate and see what happens. In the long run, you’ll feel much better and be able to develop a better, deeper relationship if you’re honest with her as early as possible.