I Want To Talk With People About Crossdressing

Update: Sorry I havent commented for so long. With my work hours I feel like I never have time to do anything. But yes, I did get to go out on halloween! And I had to talk to my girlfriend but she ended up consenting to helping me. Apparently this isnt the first time she's helped a guy go out on Halloween. The only difference we had was that she wanted to put me in a costume and I wanted to go as a real girl. I made sure I scheduled that day off and then I started preparing. I started by looking online for clothes that I would like to wear and checking with my girlfriend to get her advice. Then, on the next day we had off, we did our trip to the mall. I couldnt have been more nervous, but I was so excited to go. We went to the mall with me underdressed and we had the best day. I went home with all I needed to go out on halloween.
On halloween, I ended up dressing in a green long sleeve dress about knee length with black hose and black 4 inch heel boots. It took almost two hours for me and her to get ready. My legs chest and arms were all shaved just like I wanted. My girlfriend finished by doing our makeup and we headed out. We didnt really go to any clubs or anything we just walked around in our neighboorhood (plenty of kids and parents around) and then she had me drive to the store and go in with her. I was so nervous during the whole thing. But I only got a few looks every now and again so I guess the night could be counted as a success!

I would like to go out as well on Halloween. I think I need a whole new crowd to do so as my present costume enthusiasts are growing wise to my gender defying decisions. How wonderful it would be to go about town with a small group of people with a the single idea of just being en-femme.

I hope it did go well for you. And I would have even joined you both, just as a chaperone or give advice about what looked good.

You shouldn't care if people you don't know think your a crossdresser. For people you do know it may be a future problem as once you tell someone you cant untell them if they disapprove.

All your plans are achievable and exciting take it a bit slowly and carefully until you find stores that are acceptable unless you are completely passable in that case the sky's the limit.

Drop hints to your girlfriend to gauge her reaction instead of dropping all this on her at once. If she is agreeable that would be a heaven trip but she may not continue to support your crossdressing even though she may initially.

If she is not agreeable just do it without her knowledge, good luck and have some girly fun.

So what happened? Did you go out?

I wanted to last halloween but didn't know a girl to do it to make me sexy and passible