I’ve recently started a new relationship with a woman I really like. I want to be honest with her and tell her about my secret cross-dressing.
I’ve always enjoyed wearing women’s underwear and clothes, and my last girlfriend was supportive and even bought me things.
I went out dressed up on a few occasions as I’m quite convincing and confident.
I don’t want to dress up all the time, but I do prefer to wear women’s underwear on a daily basis.
My girlfriend and I don’t live together so I can still indulge in this and change before seeing her.
I would really like to tell her and dress up for her, but I’m not sure how she’d react.
A couple of my close friends know and think I should tell her. What do you think?
If you think the relationship could evolve into something more serious and you might move in together one day, then I believe your friends are right.
It’s good to be honest from the outset.
No matter how much you like this person, if you think you will be dressing up for the rest of your life, then you have to ask yourself if it’s something you can do in secret.
And if your new partner says it’s not for her, then maybe she’s not the right person.
Or perhaps, as with all relationships, it might be a case of coming to some kind of compromise.
She might not want to see you dressed up or accompany you outside while you’re dressed, but at least you won’t feel like you’re having to live a lie.
I think honesty is the best policy – it’s also fairer for her to know before she gets in too deep.
* More of our agony aunt Coleen Nolan’s advice on your sex, family, health and relationship problems