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.

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.

Tags:
18 Comments
  1. 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.

  2. 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.

  3. 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.

  4. Cynthia Elaine 3 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. 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.

  6. melissa la quinta 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….

  7. 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.

Leave a reply

Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials

or    

Forgot your details?

Create Account