My Best Dress-up Day Ever

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.

Crossdresser Heaven - Find Your Tribe

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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  1. Jamies time 2 years ago

    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.

  2. cdmelissalaquinta 2 years ago

    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

    • Author
      Diana Stockton 2 years ago

      I actually am spending at least 1 week every month now traveling. And during those trips spend every non-working hour en femme. I have never been called out though I am sure I am read often. I go out to dinner, shop and just try to get out. It takes a lot of confidence and each time I find it that much easier.

      My breaking point was going to Sephora to get my make-over. That is the break that made my look more realistic. I realized that the quality of the makeup makes a big difference especially when you are trying to cover that beard bluing.

      After that my next break was getting a quality wig. I had found a costume one that looked okay. But going to a wig shop, en femme, while very scary was great. I found the wig that made my look.

      After that it was just practice, practice and more practice. I got my makeover about a year ago and before that had been out maybe once or twice a year but always at night and scurrying around. Now I do not hesitate to go out during the day. I now even wear dresses as I have found dance hosiery that will cover my leg hair.

      Good luck all….

  3. Janine 2 years ago

    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 enjoyable
    Thanks for your post.
    It was a nice reminder of what it felt like on my first time out dressed en-femme.

  4. Cynthia Elaine 2 years ago

    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.

  5. Diane Stockton 3 years ago

    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.

  6. Cissy D 3 years ago

    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.

  7. terri m 3 years ago

    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.

  8. Michelle michaels 3 years ago

    Sounds absolutely wonderful. Have fun be safe.

  9. Jessica Hiver 3 years ago

    Good for you, Diana. It sounds like a very positive day en femme. Driving while dressed is a particularly pleasant experience for me. Thanks for sharing.

  10. Rosaliy Lynne 3 years ago

    You have learned one of the most basic things about being confident when you are out en femme. In general, MOST people will see what they expect to see and won’t look past that.

    Success breads confidence which, in turn, breeds more success and still greater confidence.

  11. Author
    Diana Stockton 3 years ago

    Next week I am going to make another trip south in drag. The big issue this time is the temperature. It is going to be warmer and I am not sure if it will be to hot to wear my cardigan that covers up my hairy arms. Wish me luck.

    By the way the picture above is not me. They evidently choose random photos. I wish I looked that good though.

  12. Sallysim 3 years ago

    That’s fantastic Diane, and it is true , if you blend in and be confident in who you are you do not get a second glance. I’ve gone shopping and walking around town totally en femme many times and not once did I encounter any problems.
    Sally xxx

  13. *skippy1965(Cynthia) 3 years ago

    What a great adventure Diana! I am hoping to get out in public like that soon! Thank you for sharing your delightful experience. It gives e hope that my first outing such as yours may go as well!

  14. KerryMichelle 3 years ago

    It sounds like you had a fantastic day en femme. I had the opportunity to dress en femme on my last business trip. It was fun but I didn’t do all the things you did. I did get to go out in public this morning in a pretty blue dress. It was fun, and I felt so feminine that I had a hard time forcing myself back in to drab clothes. Wishing you many more fabulous outings.

  15. sierra 3 years ago

    FANTASTIC! Hope you have more!

  16. Diana, that sounds a lot like my last two days as April. It really is a high isn’t it! Hope you have many more fantastic days to come!

  17. Tiffany Anne 3 years ago

    It does sound like a fantastic day!

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