My Best Dress Up Day Ever

As part of my job I travel once a month to a southern state. It takes about 7-8 hours of driving time to get there and I take advantage of this time to go in drag. Last week I had my best day ever.

I started my day by going to a local motel that I had rented the night before to get dressed. I am married and while my wife is aware she is unsupportive. It took me about an hour and a half to get all dressed up. It takes a lot of time to make this old guy into this old gal. It helps a lot that I have twice now gone to Sephora for total makeovers. I have learned so much.

Anyways I was going to be daring and for the first time was going to wear a dress. All my previous outing in drag have been in slacks and a top. I had recently figured out how to best cover my hairy legs with two pairs of hose one was almost like tights in beige and a pair of suntan hose over them. Last month I had also gotten the courage to go wig shopping in Nashville TN and got a quality Raquel Welch wig. This would be my first outing wearing this wig. So once dressed I got on the road.

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I drove for about 2 hours and realized that the coffee I had been drinking needed to come out. Since I was on a high I decided to be daring and stopped at a rest area to use the ladies room. Fortunately there was no one in there when I went in but I did walk past someone on my way out and did not get a second glance. Wow what a feeling, I was really passing.

My next stop was a shopping mall to do some dress shopping. While I have shopped quite a few times before in drag I always tried to hide and walk away from others. This time I was determined to just be like everyone else. I guess it worked and I did not notice anyone giving me even a second glance. While in the formal gown section at Macy’s I even had a woman ask me if I saw any size 12’s in the rack I was looking at. So now it was a test of my voice skills. I had been practicing a lot but was unsure. I kept is short and said I do not see any. She started commenting about her daughter being in the dressing room looking for a size larger. Fortunately that was the end of the conversation as I was unsure how long I could keep up my presentation. I spend a couple of hours shopping and while I did not buy anything, a woman’s prerogative, right? However, I did try on a lot of things.

So back on the road and I repeated the shopping experience once more in the next big town I went through.

I finally got to my destination near dark and it was time to call home to my wife and tell her I got there okay. I did so from my cell in the car. Then I needed dinner. Normally I would have gotten undressed in the car checked in to the hotel and gone out in drab. However I was riding this high and decided to be daring. So off to Appleby’s I went still in my dress. I had a wonderful dinner with wine and while I am sure the waitress knew my gender she never said a thing.

What I learned about this wonderfull day is that if you are confident, dress to blend, most people will not give you a second look.

I do not have a feminine face and it took a lot of time and practice to get me to this point but I now feel confident in my ability to go out in fem.

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Diana Stockton

I started dressing about 45 years ago. I still remember that first dress of my mothers I put on in the closet for fear my brother would find me. It was a yellow sweater dress. I cannot remember my motivations to do so. Even today I still do not understand them. However my dressing seems to be taking a bigger part of my life as I age.

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Amy MyersJamies timeDiana Stocktoncdmelissalaquinta LaquintaJanine Recent comment authors
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terri m
Guest
terri m

Great story. My wife is like yours. I love going shopping enfemme. My favorite stores are Macys and Dress Barn. I have gotten a few makeovers at the Estee Lauder counter. I am lucky that I still have my hair (I’m 67) and have a great hairdresser who cuts my hair in a way I can wear it in both genders.

Cissy D
Lady

What a great day! I have discovered that passing is as much about confidence as it is about looking good. Hope you have many more femme times.

Diane Stockton
Lady

I guess there are more than one of us out there with the same name. Nice story. Mine is a bit different but was a success.

Cynthia Elaine
Duchess

That was a kewl story Diana. I hope some day that I can be just as confident when I go out en femme again. As it has been 40 years since I did.

Janine
Guest
Janine

Hi Diana I just read your post about going out en-femme and enjoyed reading it It made me remember the first time that I actually got up the courage to leave the security of a motel room and venture out in public. The first thing I noticed was that when you are outside wearing a skirt is the breeze blowing up under it. The next thing I noticed was the same breeze blowing through my hair I had never thought about it happening and these two things made me feel so feminine Sometimes just the simplest things are the most… Read more »

melissa la quinta
Duchess
Active Member

Diana, I am both proud of you and so envious! I hope that some day soon I’ll have it together enough to venture out and have a lovely adventure like yours. Thanks so much for sharing! XXOO Melissa

Jamies time
Guest
Jamies time

I love your story Diana it is a great time to be a woman who loves to shop and be treated as a lady I myself loves shopping for dresses and accessories it is such a rush.

Amy Myers
Baroness
Active Member

Nice to hear about your success!
Amy

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