A few weeks ago, I had the most interesting Sunday. Like many others here, in my male life, I do masculine things, as well as my love in dressing up to be the best woman I can be.

Some know my love of cars, and I have a little red sports car which I spent quite a bit of time on in the past year. She runs as well as she looks. However, with all the lockdowns and other restrictions, there has been precious little opportunity to get out and enjoy my car with the company of like-minded people.

This is important too, though most think of car stuff as a guy thing, and mostly it is, but there are now quite a number of women who own these and other vintage cars, and some are very attractive, too. These days, most car groups that I’m involved with are more accepting of women.

However, if a trans woman were to be there that might still push the acceptance envelope a bit too far! Another few years for that I think, but I hope we will get there sooner rather than later.

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I got a notification that a car event I had been looking forward to was going to be held on a particular Sunday, so I quickly signed up! Then a week or so later, I got another notification from a group my feminine side is a member of about a shopping spree at a women’s clothing store, which was closing after many years.

A casualty of all these lockdowns I’m sure, with a few things happening that you need to get a special dress for. One of the girls arranged for an opening especially for us so that we wouldn’t be in the way of other customers.

My conflict was that not only were they the very same day, (though a bit later than the car show) and my route home would take me near the store. Sounds good, but that wasn’t the problem. Here’s the rub. My son was very keen to come along as he is quite the Motorhead too, so I had to give my regrets to my girlfriends, but still longed to go!

Later, by chance, a few things came together as my son’s older sister invited him to go to her place for the weekend. She would bring him to the show (wanting to see the cars too). I’d still have to bring him home, although he was a bit unhappy at having to stay till the bitter end like I had to.

Who else but Mom to the rescue. She said she’d come out to see the cars and take him home. What a family that young fellow has, with a doting sister and mother! (Dad too)

EnFemme Style

Wow, it was a dream come true! So, I quickly contacted my friend, and indeed there were a few spaces left, and she was also willing to let me drop off my Amy stuff with her a few days beforehand. I would get it at the store, as I didn’t want to chance to have my femme outfit in a small car and get some awkward questions if someone peered in the bag. Not very likely, but I didn’t want to take the chance.

The show was fabulous, the cars in attendance were as hot as the weather, which was pretty darn hot! So many beautiful cars and people to talk to about our shared passion. As the afternoon wore on, I’m thinking about my next stop, the boutique, but if this makes any sense to you, dear reader, I was so into the male car stuff I wasn’t sure I wanted to go dress shopping. Perhaps this is a kind of sacrilege to you as well. But this was how I felt at the time.

Though the show had been great it was wonderful to finally be able to rest my weary self on the comfy leather seat and be on the road again. When I finally made it to the boutique’s door, I was greeted warmly by my friends and handed what I call the “Amy in a bag” carry case. Then almost immediately a couple of dresses were chosen for me by the owner, and I was shown to a fitting room.

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Wow, the dresses were really beautiful, and that helped me to start changing genders a wee bit. In my carry bag, I had everything I needed.  As I’m sure many of you can attest to, there is something almost magical about changing into women’s clothes. As I slipped into the first dress, a dark grey and very sparkly item, I was starting to feel like Amy again at last.

I couldn’t do up the zipper of course but was quickly helped with that task when I came out. Oh my, the Oohs and Ahs were wonderful to hear, and I was asked to do a little spin so everyone could see it. I felt like a model on a runway! Then the owner got me a pair of heels to put on!

There were more dresses to try on, and the owner and her helper started saying Amy’s the girl who looks good in everything! Well, I’m not sure that was true, as they are trying to sell these dresses. It was the feedback from my friends which was the most important.

This was a very wonderful, and indeed a very magical experience. It was one that GG’s must have from time to time. No wonder they like to go dress shopping together! I tried on so many dresses, skirts, and tops that I lost count of them all. I actually had difficulty deciding what to buy as my budget isn’t unlimited, so some tough choices had to be made! In the end, I narrowed it down and bought three dresses, two skirts, and one pair of heels, the first dress and the first pair of heels she gave me to try on.

It was such an amazing day! Firstly, a guy solidly in car heaven, and then a girl in a paradise of beautiful dresses. One of my friends remarked that I made a total 180 turn from when I went into the change room to when I came out dressed as Amy. The truth is Amy went in and came out, only I looked and felt like Amy when I made my second entrance. This observation was borne out by another person. Honestly, I didn’t feel as different as they said I seemed.


Have you ever had the chance to go clothes shopping with either other CD’s/TG’s or some GG’s?

Do you feel you make a big shift in personality when you get dressed up?

What would be your fantasy dressing spree?


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Amy Myers

I'm 60+, hetro, married, and love dressing up! I keep saying and feeling like I'm new to this, but I have dressed from time to time since my pre teens, but just late 2018 it seems to have become of a bigger part of me, rather than just a role I played from time to time. I'm interested in music, cars, photography, and plus other interests.

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Jane Wherry
2 years ago

What a lovely day you had Amy. Combining both of your passions. Lovely that your shopping with freinds went well.
Never been out with anyone at all, just solo. Would love to one day.


Kimberly Ann Victoria
Active Member
2 years ago

I have never had that opportunity but would like too. I glad you had a great day shopping for clothes.

Vickie Steel
Vickie Steel
2 years ago

I’m a car/ truck guy
/ Gal I’d love to dress up and be both a skirt wearing panties wearing truck showing sissy fagget just me . I did here of a trans woman years back 5_6 year’s ago north stpaul mn she was at car show . I would have loved to meet her and talk to her . Brave trans woman

Kathy LaDonna
Trusted Member
2 years ago

What a wonderful turn out for you girl. Lovely outing. Especially the ending part.


Caty Ryan
Active Member
2 years ago

Well done to my lovely Canadian friend Amy!!


Gianna Bonita
Gianna Bonita
2 years ago

Such a wonderful outing Amy. I’m so glad you had a wonderful day. Thanks for sharing here on CDH.

Melissa Sue
Active Member
2 years ago

Great story, thank you.

Jane Don
Active Member
2 years ago

Sounds like a great outing–I’ve been to car show (out of my area) dressed fem & no problems-(my late wife was always with me)–never brought my old car to show while dressed–wife kept bugging me to do it though -I just didn’t have the nerve–Now the old girl (Car) has sat untouched in the garage for yrs & I want to get it going again but don’t have the extra money to put it in a shop– It would be great to make some Open minded folks to socialize & work on the car with–Anyone around London Ontario interested?

Marie Chandler
Trusted Member
2 years ago

What a lovely day and oppurtunity to combine two of your favorite interests.Thanks for sharing!

Noble Member
2 years ago

Thanks Amy. What a fun experience.

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