So just a quick note, then a little about me. I was advised to put something in here to make it clear that I'm not interested in guys, just to keep the thirsty men at bay. I'm fine with talking, but I don't really role play, and I'm probably not going to be a good resource if you're looking for someone to talk you off.
Okay, that being said, here's some of my background:
I've wanted to be female since I was 7 or 8. I have a sister who is 5 years older than me, and I was always jealous of her clothes, makeup, and toys. I felt a lot of pressure from my parents to get married and have a son to pass on our family name, and so I have always tried to do my best to do male things, but I've never felt truly comfortable. I remember trying on some of my sister's things when I was 13-14. My sister had moved out, but left behind some things. I was also left home alone quite a bit, and so I would also mess with my mother's makeup at that time. Of course, I didn't know what I was doing, and this was before youtube. As I hit puberty I stopped sneaking clothes and just tried to be "a man." I lacked the confidence needed to date much in school. I didn't have my first real girlfriend until my Jr. year. That didn't last long. Pretty much everyone I've dated has been someone that I was set up with, or someone I met online. It wasn't until part way into my first marriage that the idea of crossdressing came back up. I suggested it to my wife, and she did try it, but it wasn't for her. She said I could do that if I wanted, but she didn't want to know about it. Our marriage eventually fell apart, for a lot of reasons, and I started dating again.
The second time I made it a point to find someone who was okay with my crossdressing before getting too serious. When dating, my wife and I would get all dressed up and do each other's makeup, paint our nails, etc. Eventually, we had kids, and a lot of this had to go back into the closet. Fast forward to two years ago, I'm starting to realize that it's more than just wanting to wear women's clothes. I really felt that I wanted to be a woman. Therapy went well, and I finally had the discussion with my wife. She was very understanding, and was willing to be supportive of the transition, however she doesn’t identify as lesbian, and felt like staying married would not true to who she is. It was a hard decision. As strongly as I felt about transitioning, I love my wife and kids more. I wouldn’t want to do anything to destroy what we’ve built together. I have made it many years as a man, and I’m surprisingly good at it, so at least for now I’m just going to stay the course. If I get the chance to dress and be pretty I’m still appreciative, as I know there are others who don’t even have that sort of freedom.