Coming out as a cross dresser
The 'when' to tell is as important to consider as the 'how' to tell. Whilst I acknowledge arguments for and against telling a prospective partner before things get 'serious' I think it is risky to set a blanket guideline. Actually getting to know the other person can be a big part in working out how and when to tell them.
In my own case I finally told my wife after 26 years of marriage, during which I'd had a couple of longer periods when I was able to refrain from cross dressing but about ten years before I told her the need resurfaced and I did so very much in secret.
As has been mentioned, I too felt I was living a lie but I also felt that I was being dishonest with my wife. As I later told her, it wasn't so much the nature of the secret that I was keeping from her that did the damage as the fact that I was keeping one at all. As the need to cross dress began to consume more and more of my life the toxicity of keeping that secret from the most important person in my life began to tell. On two separate occasions I approached suicide, only to back out at the last moment, not because I was afraid but because I actually thought about the impact my death would have on those who would find my body.
Not going ahead with suicide though created its own problems because I felt an even bigger failure so I began drinking, increasing gradually in frequency and amount. I eventually became a totally obnoxious and unpleasant person to live with. Once I realised that my wife was not going to leave me I knew I had to come clean and tell her. I was prepared to lose it all if she rejected me because, in truth, I didn't think I could feel any lower.
In order to tell her I chose a neutral location, a public park here in Canberra where there were no distractions but where we also had privacy. After some uncomfortable smalltalk, my wife being very much aware that I had something to say, I finally told her that I had been harbouring a secret since my childhood and then came out with it. "I am a cross dresser." She was stunned for a few seconds and then essentially said "Is that it?" It turned out that she thought I was going to ask for a divorce, so the news that what had been causing my problems, and led to my abominable behaviour, was 'only' that I liked to wear women's clothing was something of an anticlimax.
The road from there wasn't totally smooth of course. It took her some time to get her head around it a bit more but especially after I'd told her how close I'd come to suicide she knew that how she reacted overall and how she handled the situation was very much like having my life in her hands.
She went through all the same emotions and feeling other wives have. She felt betrayed, mostly because she thought I'd felt that I couldn't trust her. She felt confused and questioned my sexuality. She wanted to know if I wanted to "become a woman". She also needed to know if I wanted a divorce after all. I answered every question honestly and told her whatever she wanted to know but no more. Together over the next couple of years we slowly worked together to become comfortable with Jane's part in our lives, to the point now that we've no longer any fears and have told other family members, including our four children and relevant partners, and a number of trusted friends.
From all that though there is one small conversation that sticks in my mind. Early on after I told her, when it was all still quite raw, I told her that I probably should have told her before we married. She thought about it for a while and then told me that that might not have been a good idea because she was a very different person "26 years ago" and that had I told her then it's very likely that she would not have married me. When I replied that given I was perhaps not the man she thought she'd married maybe that would have been for the best her response was unequivocal. "Honey, look at our four amazing children, their partners and our two beautiful grandkids, and the life we've had together overall and then tell me you really believe that." She is a very wise woman. We've now been married over 33 years.
There is no right time to tell as far as a general rule goes. For some, before a relationship develops might be best. For others later in a relationship that has developed in love and harmony might be better. In the end, I believe only the cross dresser will know his/her circumstances and the other person involved. I would hate to advise telling someone early only for them to miss out on a relationship like I have but I am also aware that leaving it later might also provide the appropriate straw to break the camel's back.
I'm just happy that it has worked out for me.