Dear Ms. CD Manners,

I have a very dear friend I've known for more than 10 years. Because we live several hundred miles apart we only see each other at a festival we both enjoy, once a year or less. Because of our busy lives, we only get to talk on the phone every couple of months, but when we do talk, it's for hours at a time and feels as though only days have passed.

My friend, let's call her V, is TG. I have only ever known her as female, but she is forced to live as male. Unfortunately, she can't transition and, due to her profession and her DADT roommate, V rarely gets to be her true self. Even when we talk on the phone, she has to choose her words carefully or drive miles from home to talk freely. We've talked for years about getting together some weekend halfway between us and spend the entire weekend just visiting, shopping, walking & talking, and doing whatever we decide, with her as her true self.

I live mostly male, but am occasionally gender-fluid. I've told V this, but she has only ever seen me and spoken to me as male. I dress at home and have very few select friends who have seen me dressed. I keep this part of myself quite closeted, mostly due to my profession. I have never been out in public as female and would never do so anywhere I might expect to find someone I know, personally or professionally.

The rub is... I have wanted to venture out of my house as that fluid part of me, to experience more of the world as the part of me that stays so carefully hidden. Because of our comfort with each other, and her experiences in both male and female worlds, I think I would be more comfortable exploring that part of myself with V. It's okay with me if she would rather know me purely as male, but I don't know if she would be okay seeing me as female unless I ask.

Would it be gauche to ask V for her guidance in blending with society as female, even to assist and join me on my first foray into this world, or would it be crude and offensive? If you lived in her world, would you be offended if a good friend were to ask for your help in this venture? I have considered how I would feel, but I would like to know how someone else would feel being asked such a question, and whether it would be offensive to even ask.