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Write her a letter, give it to her at the end of a nice, relaxing evening.
In the letter you can explain everything clearly without getting all emotional, and she can read it in her own time. The benefit is also that she has time to figure it out for herself. That way it wont put her on the spot. Sometimes a person's initial reaction might be harsh or negative, just because it is unexpected and come as a shock.
I know I would've preferred to find out in such a manner.
Good luck
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Kaylyn,
To help you with your dilemma, I will quote my dear Dad whom passed away in 2006:
"Oh! what a tangled web we weave, When first we practice to deceive" - Dad & Sir Walter Scott, 1st Baronet.
Honesty is always the best policy.
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Sounds to me that kaylynn is ready or at least wants to tell but is looking for advice on how to. Ok, honesty, sure of course. But that is not saying much other than the obvious. So what I will add is that it be done in person. Pick a time when you have plenty of it. Try as best you can to pick a time when stress is at its least. Start off by explaining that you feel close enough to her that she is important enough to you that you feel she should know. Then simply tell her you cross dress. She will likely have many questions. Answer them and be patient. Don't get upset at questions like are you gay or do you want a sex change. Those are always natural questions that come up. Don't be upset if you have to answer some of the questions more than once. Be patient. She may simply need time to digest this before a Conversation begins. I wish you the best.
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i think you have to decide what you can live with and be prepared for a variety of responses...she probably isn't going to jump up and down and say "fun! lets go dress you up!"...in reality her response is probably going to be luke warm at best. I think it is important to discuss expectations and understand what you are willing to give up for this girl. But she also needs to be able to decide what she wants to put up with, that is only fair.