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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 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 – everything. PLEASE!
One piece of advice I was given years ago was to dress appropriately for a lady about ten years younger than my chronological age. It think it’s good advice as being en femme tends to make us look younger than our male selves.
I wonder what is behind your sister’s challenge, if she really expects you to do it.
Do as much or as little as you feel comfortable but don’t put yourself in any dangerous situations.
Best wishes,
Go for it Linda. Why not? Have fun. Dress appropriately. Nothing extreme. The first time I went out fully dressed was for a Halloween party long ago and I was really nervous about it. Unlike you I knew many people at that party.
No doubt people will see you but unless you are dressed extreme you will be just another face in the crowd. Also not being in your home town where you may be known, you will be where probably no one knows you. Even if someone notices you are a cross dresser, it really doesn’t matter because you will be leaving them behind. Don’t do more than you are comfortable with.
Get used to the wig, don’t go extreme with the makeup and get used to the heels. Your flats would probably be OK but for age appropriateness, a short heel I think would be the way to go. Sexy heels are great. I love them and wear them often but when going out, walking around and being on my feet a lot I even go with a shorter heel. Good luck.
Skippy is so right about that. You must be comfortable and behave naturally. If you look nervous or behave strangely you will definitely get noticed and more than likely it won’t be for how you are dressed but it might look like you are up to something.
If you find yourself getting real nervous in a place or situation it probably is best to avoid it. You could always just go out and walk around. Get around people. Go in stores, walk around. If you are nervous or uncomfortable with where you are keep moving.
I’ve found that the more I went out the more natural, relaxed and comfortable I felt. I also found that going out with other dressers is a lot of fun. I really love and enjoy the lifestyle. I hope you will too,
This town is next to a U.S. Marine base. Red-blooded and total macho. Walk here. Just is never going to happen. Suicide. There are no malls. No shops. A small town, military orientated. Perhaps good advice where a large cross section of society exists. Go out with others? This is small town, not San Francisco. If there is another she is as fearful as I am.
It sounds like an awesome challenge with a very nice reward. It also sounds like you are very brave.
One thing, I would be sure to dress comfortably. Ladies on long car trips are not likely to wear a dress, heels and hose – at least not anymore. The older women I know mostly wear simple tops and slacks, and then flats or trainers. Maybe a knee-length skirt.
That’s not as exciting, but we really don’t live in the age of Aunt Bea and Miss Daisy anymore. And since you will be dressed as a woman and using the women’s restrooms, well, I think being dressed more or less as the other people using the restroom will attract less unpleasant attention.
Please don’t think I’m raining on your parade. It is a wonderful thing to do and I think your sister, by challenging you this way, is helping you achieve the dream so many of us have – of dressing and going out in public and being ourselves. I wish you all the luck in the world and hope you have a wonderful time.
I know in my male mind that you are correct. My girl mind still wants to be in a dress. Rather than observe ladies at a mall, I think now I should quietly observe at an interstate rest stop. A shopping mall would be more of dressing to impress. A highway rest stop would be how ladies my age dress to travel. Thank you for a critical, but realistic observation of realistic attire.
I travel often en femme and have found as long as to you try to blend and do not act scared you will often blend. I really started going out more in the last year. My two biggest breakthroughs were makeup and wig. I went to a Sephora in Indianapolis, ( I live in southern Indiana) and had my makeup professionally done. It really helped my apperance. I also found a wig store in Alabama while traveling and had a personal fitting. I found that these two things really gave me confidence. Now I travel at least once per month on business and each way and evening I dress and shop and eat at restaurants en femme. I am read occasionally but no one has ever said anything to me.
2016_personal stories: Linda H. original post:
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 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 – everything. PLEASE!
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