Every once in a while, a guy I’m with comes out to me and tells me he wants to try cross dressing or he does it in secret, and I understand he feels safe with me, a trans women. I feel good that he feels safe and in many cases he has never told anybody else-it’s a huge event for him.

But I’m not into dating guys who want to dress with me or have me dress them. It doesn’t bother me, I just tell them I’m not into that in the relationship. I encourage them and even give them tips. But what does bother me is when they keep insisting that I help dress them or go out as girls or help them go deeper into being a girl. Some I have to keep saying no, and they won’t stop. I’ve had to break up our relationship over this.

There are so many possible reasons for this as well described in the post and the chat. In most cases I got the sense that they genuinely enjoyed being with me as a man, but then this dressing desire started taking over. I’m not looking for romance so it doesn’t bother me because I enjoy having easy options to find somebody else.( I live in San Francisco). What bothers me more is that most guys are short timers and see hooking up with a trans women as something they just do a few times. I wonder what is driving this fear, lack of interest in an ongoing thing, treating it as a fetish. But I suppose as acceptance increases, this will hopefully improve for everybody over time. By putting ourselves out there, in a positive way as best as we can, is the best we can probably do.