I thought I should start a separate thread on this issue. We have just started talking about taking a 3-5 day trip in the next 6 months where entire time is en fem. This is both exciting and extremely scary at the same time. There are just so many things to consider and learn that I'm worried I'll stumble and I/we will be embarrassed.

Any ideas on how to cope would be appreciated.

Background: Dress three to five nights a week for two to three hours, but it's miad. No makeup and no wig.

Items I need to check out asap and then get comfortable with

-- dressing all day instead of a few hours
-- wearing a wig, after I find one we like
-- walking in heels/wedges for all day without wearing tennies
-- using ladies restroom (big first)
-- changing out earrings, from studs
-- learning eye makeup for droopy eyelids
-- adding time for makeup

My list of items to check off:
-- get fem reading &/or sunglasses. Easy to do, just have to do.
-- get wig and learn how to wear all day. A challenge since I don't even like wearing baseball hats for long.
-- pick out three best footwear and then narrow to two. One for daily and one for evening. Evening heels/wedges are easy, the problem is how to know ahead of time if 2" fat heels or wedges would be better for all day.
-- Learn how to apply eyeliner, eyeshadow and mascara in a way that looks both nice and not totally the same as no makeup. Currently, if I just add mascara, I don't see any real difference after I put the glasses on.
-- do I need a unisex/fem coat/throw as it will be in the upper 40's at night.
-- is there anything that will work for tops with leggings and a mini skirt, or is that too much.

Do not need to be at all concerned with: nail polish, lipstick, finding skirts/tops/dresses/shoes or walking in heels/wedges.


And the big one: how do I make sure all this prep and time and focus does not upset the applecart with wife.

Yes, I know this is a long, long post, but hopefully at least someone here has faced a situation similar and can share lessons learned.