I've had this friend for many years now who likes to cross dress, he has been doing it since he was a teen and not many people know about it. We have been friends for ages and he told me about his crossdressing right off the bat so it's never been a problem for me to deal with, it's his life, his choice and I have supported him over the years even when his partners at the time didn't.
Of late our relationship has developed and we have started seeing each other in a more intimate way and here inlies my problem, I have spoken so much about his crossdressing to him and I have never been phased by it and I have even seen photographs of him before but now that our relationship has developed and he has asked me to see him in person dressed I am a little concerned.
I falling in love with this guy and I am scared I am going to react in a bad way to his dressing, even though I have been so accepting of it before hand. He is a great guy with awesome sense of humour and I love our friendship/relationship. I know he must trust the hell out of me cause no-one else has ever seen him cross dress and only a 3 people beside me know about this, 1 being his ex who dumped him for doing it.
When he showed me the photographs I was kind of nervous and a little bit hhhmmm but then thought well he is still the same person under the clothes so whats the big deal, but I am just scared Im not going to be as good in person.
He wants me to see him this way and I want to see him too so I can register how or if it is going to affect us. He has suggested that he (in his words) transform infront of me rather than just dissappear into a room a guy and then come out a chick but I am not sure if this is the best way. He also suggested I help him transform, Is this a good thing?
I have always been a firm believer of people should do what feels right for them and not suit their lives to everyone else's standards and this is probably why I have accepted his crossdressing, even encouraged it but I feel a tad weird now and I dont know why.
I dont want to limit him as to when or how often he should dress and I dont want him to stop cause I see it as it being a part of who he is, like another part of who he is, is a motorbike rider. I see it as a small part of what makes him him and now I think there is something wrong with me for being so accepting before but now nervous about it now. I am hoping its just cause our relationship is changing so my perception of things is adapting and I am having to look at it in a new light.
I am just so confused as to how to go about talking to him about this, I dont know how I am going to go when I do see him and I dont want him to think I cant handle this until I know for sure I can or can not.
Is there anyone out there in this community who can give me what their experiences where like and what they felt and did the first time they saw their partners cross dress or anyone here who can calm my nerves and give me some advice on how to deal with a first time seeing their partners dress.