Another Step Forward for Amy, her first Makeover!

If you have not yet read my earlier articles about my (Amy’s) forays into the outside world, I would invite you to do so, perhaps after you finish reading this one.

Over the 6 months or so, I have learned to take on the world outside of my closeted home and have grown immensely from those experiences. Though due to other conflicts, I had not been able to attend the last few pub night dinners. As a result, I was particularly anxious to get to the upcoming one. It is such a wonderful experience just to be out at all, as Amy, but was missing some of the CD girls I’d become friends with during my other times with them.

However, this time I wanted to improve my look quite a bit.
I had been experimenting with makeup for some months, and my application of foundation and blush was becoming better, but anything to do with my eyes was still a pretty hopeless case. So, when I am planning on going out, I wore foundation, blush and lipstick, and left my eyes alone. I felt that no makeup was better than badly applied make up, and it was time to change this.

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A couple of months prior, I had dropped into two cosmetic’s stores in a major mall, at one place I seemed to get a very cool reception, the other, though busy, were happy to answer questions. So, when the time came, I booked an hour’s makeover appointment with the latter store, and scheduled it just a few hours before my night out was due to begin.
When I called them to book my appointment, I explained that I would be appearing en femme as Amy, but likely paying by card in another, male name, and they were quite alright with that.

For this outing, I had several new things to wear. A nice new black dress that came to a couple of inches above my knees, sheer black tights with a polka dot pattern, silver necklace, bracelet, anklet, with my silver black stiletto pumps. Though, for going into the mall, I wore black shoes with only a modest heel on them. For my hands I used some new super sparkly silver nail polish, clear coated, a silver ring with two pieces of turquoise set intertwined, and a couple of other rings rounded out my hand jewelry.

This wasn’t the first time I’d worn rings, as I’d bought cheap ones at a store which caters to girls and young women. When I wore them, I felt like they looked a bit too cheap, plus two of the five broke in short order. These particular rings were better quality and they looked it as well. I wanted to present myself as a well-dressed, professional woman and cheap looking jewelry doesn’t really cut it. Also, the turquoise ring was a “couples” ring, and since I’m not single, I thought it would be more appropriate.

The other interesting and exciting thing was the fact that this would be the longest time I’d ever been en femme! I was so wound up I had trouble sleeping! Which is not good, as it was going to be a long day with a two hour plus drive home late at night.


After a shower, I started getting ready with a full shave and then dressing. Panties, padded panty, pantyhose, latex waist cincher, (the boned one I thought would be too much for the long period of time I was going to be dressed), black bra, breast forms, lovely black satin camisole, some basic make up, then jewelry were all a part of my preparation. Being busy has its advantages since I was just concerned about getting dressed but then, wow, by the time I was done, I was starting to run late! Then I started getting a serious case of nerves like it seems I always do, the “Am I really doing this?” worrying and thought about chickening out, but fortunately didn’t.

I had an hour’s drive to get to the mall but didn’t want to drive too fast as to attract any official attention from the police. Fortunately there were no delays on the road and after I parked, I started getting really, really nervous again, but swallowed, and walked in 5 minutes late with my head held high, smiling, and hoping that I looked a lot less nervous than I felt.

The young woman who greeted me was the one whom I booked the make over with and she immediately made me feel very comfortable. This location has a private room which they offered to me when I booked so I took it. This made me feel rather less exposed, as this location’s makeover chairs are very visible by anyone walking past in the mall. One of the first things she said was how nice I looked which also helped to make me feel a bit more relaxed.

Then she gets down to business, and she asks what kind of look do I want? After much thought beforehand I had decided that I wanted a natural look, so that’s what I told her.

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She did take the hour or just over what I’d booked and started from my skin up with moisturizer, foundation, powder, primer for my lipstick and eyes, etc. I could not believe the number of cosmetics that she used on me! All the while she chatted nicely with me, so we got to know each other during the time.

Lastly, she applied the red lipstick I usually use with a matching lip liner pencil to sharpen and extend the perimeter of my lips a bit. When I looked in the mirror, my reaction was one of WOW! I could not believe how nice I looked and felt. That was the best part, I think. Partly knowing that I looked nice, and the interaction with the makeup artist herself gave me a lot of confidence. I think that is a big part of the makeover itself – the way the person doing it treats you, though ultimately you need to look good. Whatever look is right for you.

I know this is simply their job but like with everyone who is in the sales or service industry, there are times when the frustration of the job, or the company, or your last customer must get to one. However, with work like this it is so important to have a positive attitude towards the customer. When leaving, I felt like I was on cloud 9!

With still nearly an hour before I had to leave for the dinner, I realized with all this excitement I didn’t have any lunch, so I went into a coffee bar and ordered a snack and coffee for myself. After which I went and did some window shopping. If there was a downside to the afternoon, this was it. My shoes started really hurting after walking a little while. These were flats by the way and my feet were still hurting, I’d left my heels in the car for later, not wanting to look too “over the top” for the mall, though this is a higher end one so there are some very well- dressed folks in there too. But high heels in the mall isn’t my idea of blending in!

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So, I just hobbled back to my car and drove to the pub! Then I changed into my heels before getting out of the car and went to the local Starbucks for a coffee and snack to keep me going till supper. Then a gent, who was perhaps about my age, started chatting me up a bit while we were in line, by complimenting me on my food choices! After a bit of light banter, I did my best to respond politely, he got his items and said “bye, see you later” and left. Much to my relief, I must add, as I didn’t want him to follow me over to a table to continue chatting with me.

When I got to the pub itself, it was almost anti-climactic, though it was supposed to be the main event of the day. I received several compliments on my “look”, so I got to relive the experience by telling the other girls about my makeover experience!

All too soon it was time to leave for the late-night drive home, with my usual stop at the Tim’s coffee shop for a bit of refreshment to keep myself perked up for the rest of the drive home. A nice gentleman also held the door for me as I went in which just helped boost my euphoria a bit again. These drives are very pleasant as I’m so completely wrapped in being feminine and so much at peace with myself and everyone else.

By the way, how did your first professional makeup go, and did you look and feel like a million bucks when the makeup artist completed his or her makeup artwork on you?

Thanks for taking the time to read my article and feel free to share your first professional makeover with the rest of our CDH readers.

Sincerely, Amy



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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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Melissa Davis
4 years ago

As Amy discovered, a professional makeover does wonders for your confidence. My experience may be of some help to others. I made the appointment by phone with a Sephora store in an upscale mall near Boston, saying that I was older than many clients and gender nonconforming. When I arrived en femme, I had on a bit of lipstick and a hint of eyebrows. I explained to the 40-ish expert that this was simply to avoid attention and should be removed before we started. I received the full hour promised for $60. She explained what she was doing and helped… Read more »

Rozalyne Richards
Rozalyne Richards
4 years ago

Hi Amy thanks for sharing your story with us x I myself have yet to have a professional makeover, it’s something that I hope on having sometime in 2020, along with attending a venue en femme as Rozalyne, it’s something I’ve been thinking about for ages letting Rozalyne out of the closet and show her to the world, well that’s for the future something to look forward to xxxxx

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