I'm never stealth when it comes to my "Lovers"...
When I first meet a man that I find interesting and feel that a relationship may develop I plan for the eventuality that I will have to come out to them a some time or other, but I will always come out to the person if there is a strong possibility that we will become intimate, and we are well under in our relationship.
While I would love to be stealth it just isn't realistically possible and the consequences of being found out later can be devastating. Consider this; you pass completely, you have developed a wonderful relationship with the guy, you are intimate, you start living together, you decide to get hitched, and you feel as though you are going to live happily ever after... Until... you are discovered. Far fetched? I don't think so, there is always that chance, that someone from his or your past will come onto the scene and wham, you've got some splaining to do Lucy...
How do you think the person would feel. Shocked may be putting it mildly, devastated would be more like it, and there is the risk of violence to boot. What if you had shared property, what if there were children involved, what about his family, his friends, how will he feel? How would fare in a divorce?
A true relationship must be based on truth and honesty (Amongst others) and I would propose that anything short of this is not a relationship, and I think that one may be a little naive to believe that they can hide their past.
Steph