New first trip help please

I just got a challenge from my sister.  She knows that I enjoy wearing dress and all that is proper under them.  She also knows that I want to feel a breeze under my skirt, I am strictly “In the closet”.   I have not been out in the public view, ever.

I plan to drive out to visit with her next May.  I live in California, she is in Indiana.

Her challenge is:  One day on that trip, you will check into a motel as Mike and the next day, check out as Linda.  You are to stay dressed all day.  This includes stopping at a proper restaurant for lunch.  Either take a picture, or get someone else to get a picture of you along the way as proof.  When I get fuel I am to use the Ladies room to relieve myself.  Snap a selfie of my face in the mirror so she knows I did that too.  I am to check in to the next motel as Linda.  I can leave the next day as Mike. Along the way, I am sure that I will not see anyone.  I am also sure that I will be scared out of my bra.  I also know that if I let the situation become embarrassing, it will.  Yes, they are going to talk.  So – if they are talking about me, they are leaving someone else alone.  As a reward for me finally doing what I have wanted to do for 40 years, she will make me a dress.  Not buy me a dress, but she will sew me a dress.  She has never seen me made up as Linda, so this will also be a major first.  My sister making her big brother a pretty dress and then I will be in a bra and panties while she adjusts it.  Should be quite a trip.

I have started by selecting a dress that a lady of my age would wear.  Mid-calf, maybe a bit more.  Floor length would be wrong for a trip.  Second, an older lady would wear heels, but subdued and with a shorter heel, perhaps 2 inches.  I bought a black leather purse with a shoulder strap, and I am putting over my shoulder every time I walk around.  I think that it should be second nature to have the bag.  Boys have pockets, ladies carry a purse.  And when I walk, it is in the heels.  I have to get used to them.  I normally wear flats.  About 2 months before I depart, I am going to wear the wig every time I am home.  I need to be accustomed to it on my head.  I think the same with make-up.  If I am not going anywhere, but on a full face.  Tone it down to age appropriate.  Then I am going to the food court at a mall.  Get something to eat and just people watch. Not the pretty young ladies that we wish we looked like, but ladies in my age bracket.  Watch how they walk, carry the purse, move their hands, hold their arms.

I know that a lot of you ladies out there are out all the time.  You are comfortable and feel with the city.  I am 70, 6 ft. tall and weigh, well, I wear an 18.  Please help a neophyte gurl out with suggestions on – well, everything.  PLEASE!

The hotel I start from: Probably Tucumcari, NM. Small independent operation or chain?  Day ending around Effingham, IL. Check into a major chain, i.e. Best Western, or a small independent?  The restaurant:  Chain like a Denny’s or Mom & Pop?  I know that everyone wears jeans, but I want to wear a dress.  I don’t think it would be that out of place.  Should I go with flats or the short heel?  I feel a dress gets heel.

HELP PLEASE!