Crossdressing is something that I have experienced ever since I started hitting puberty.
I have tried to embrace it, purge it, ignore it, but it still always lingers in my mind.
I have been to a couple counselors about it before, and tried to better understand myself. It's not going away.
The extent of my crossdressing comes and goes in waves. I have been fully dressed up as a woman, but other times in life I just crave to wear panties and pleasure myself sexually.
My biggest concern is how my new girlfriend would take it.
This girl is really promising and I could see myself marrying her.
I have had girlfriends despise it, love it, be indifferent to it etc.
When should I tell my new girlfriend about it, and how should I approach it?
I have tried many different approaches. The one that got the worst response was starting out saying something like "I have something I really need to tell you..." and kinda playing it up like it was a big deal.
The problem is that crossdressing is kinda a big deal to me, but I don't wanna tell my girlfriend this and scare her off. Bringing it up too casually might not be fair and conceal the extent to which it is part of my life, but playing it up might cause her to think that there is reason for concern.
In the past I have shared some kinky fetishes with her and she has to me as well, so we are pretty open about talking about intimate stuff at this point.
What's different about crossdressing is that it's not only a fetish, but it plays a part of my identity. It is a way to express my feminine side in an extreme way.
Crossdressing also has a negative connotation with a large amount of people, so I'm scared what she would think.
I'm just curious if you guys have any advice or past experiences with girlfriends because I know I'm going to have to tell her eventually.