My first makeover

Next month will be the 3rd anniversary of my first professional makeover.

I have never written about the experience, how it felt to sit in that chair and come out with a full made up face. So here goes,

I worked for a travel company up to August 2020. In my department, I supervised after sales and all things air. Apart from the work, the best thing about it was the people. All of them accepted me working dressed at least once a week, normally in my favorite office wear. There was always a joke that I was the smartest looking woman in the office.


One quiet week in May, my colleague who supervised the sales team asked me about going to have a makeover. I jumped at the idea initially not knowing too much. Thoughts and expectations ran through my mind until work got in the way. Just before we finished for the day, she had booked an appointment for 8am next Friday which gave me a whole week to wait.

As Fridays were dress down, I decided for the skinniest jeans I had, a floral top, blonde wig, pink ballerina shoes, a blue long coat and minimal makeup. Well, I just didn’t want to delay the experience. Side by side with my colleague, we left grabbing a pair of sunglasses to wear on the walk. Looking back, I’m not sure why but perhaps it was a result of “stepping out” nerves.

The store had just opened, a few shoppers were doing their pre work browsing, a few spraying a generous amount of perfume from the tester bottles available, something I am very guilty of, especially the expensive stuff, thank you Dior and Armani! I had 45 minutes before we had to go back to the office so making the most of every second was crucial.

We went to the counter and their high chair was waiting for my arrival. Karen, the assistant, was there already with brushes in hand. My colleague told her what we had booked and I made myself comfortable. Then, we were all set and ready to go.

Karen asked me several questions, her face showing surprise with my replies, since the voice didn’t match the appearance. Regardless of this, Karen was brilliant! She first applied concealer, then foundation all the while telling me the best brush to use with each product. The technique being revealed with each dab and stroke to my face. Next came highlighter, blush and the swish of the brushes running effortlessly around my cheeks.

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Now for the eyes, a dark shade of eyeshadow was chosen. The blending brush moving effortlessly over my closed eyes. On to the eyeliner, knowing that I’ve never been brave enough to apply myself, so this was the moment to get it done.

Holding on a little tighter to the seat I looked up while the liquid black eyeliner was applied with ease, mascara to finish the eyes and with lipstick on the makeover was complete. For that 45 minutes, time stood still. Me being in that chair not conscious of looks, stares, or other shoppers at all.

The moment finally came to look in the mirror. Stunned would be an understatement! I saw Samantha staring back at me with a fully made up face ready to step out into the world.

I thanked Karen for her time, patience, tips and tricks but most of all her understanding. We said our goodbyes and her parting words were, “You look just as good as a woman as you do a man!” As we walked out the door, I put my sunglasses in my jeans – won’t be needing those for a while!

Thank you girls for taking the time to read this article pertaining to my very first makeover. Please take the time to either leave a comment in response to my article or to one or more of the three questions I’ve posed to you below:

1) Did you know that when you smile, not only do you show the world how happy you are to be a woman, but you also make yourself look younger?

2) How many different types of smiles are you aware of? Tell me your favorite (mine is more of a nice reserved smile, like Jackie Kennedy used to give).

3) If someone came up to you and told you how pretty you looked, wouldn’t that make you smile? Well, before you go out, or take pictures, or do anything en femme, look in a mirror and tell yourself how pretty and feminine you look! Doesn’t that make you feel better? Then show it with a smile!

Thanks again girls,

Sincerely, Samantha



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Samantha Joan

My crossdressing journey started at the age of 13, although upon reflection, it started a little earlier, like most, it was a ball of confusion, feelings and questions I honestly couldn’t answer nor could tell anyone. Growing up and trying to dress was difficult. There was no internet, so my access to fully understanding and knowledge was almost zero. My parents knew, talking was tough as instead of confronting my crossdressing I ran away from the conversation, sadly never to be talked about again. Like my favourite sci-fi saga, there was an awakening in the force, Samantha came into being, thanks to some very supportive people who were and still are invested in my journey. I am here to be part of this wonderful community, support others and share my experiences, plus if anyone knows the secret to a perfect, flawless makeup look, please let me know. Thanks for reading! Hugs, Samantha x x x

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Inga Roberts
1 year ago

Thanks for sharing this experience with us all. I have tried makeup a couple of times but failed miserably, looked like a blokectryingvto look femme. I will one day do what yiu have experienced and think I will orobsbly cry if I get to see a beautiful woman looking back at me. Sharing you first time is very encouraging and I am hoping my wife will take me to an expert in makeup for a birthday or Xmas gift, it would make me so happy.

Thanks again for sdaring your soecial moment. Inga

Melissa Tandry
1 year ago

Sounds like a great experience and good that you are confident enough and comfortable with going out dressed. I expect it helps with the support you have. Hopefully one day I will find the courage to go for a dressing experience to get help with my look and how to use make up.
Thank you for sharing your experience.

Angela Booth
Trusted Member
1 year ago

Thank you Samantha. My one and only makeover was at home some years ago when I booked a make up artist. It was a revelation and the tips I received served me well. I am so happy that you had the chance to have one done. What wonderful co workers you have.

Cassie Jayson
Trusted Member
1 year ago

This afternoon as I was walking in the park with a fried we met one of her friends who lold me my dress looked really pretty. I was so happy and thanked her so much. When I told my friend how worried I was about being found out. I was told to just own it and be myself!!


Active Member
1 year ago

Yes I do love a makeover! It gives one new drive to push on and hit all the goals you wanna score. Although it’s not my 1st makeover I’m heading for one next month and it’s very exciting. I can remember my 1st makeover it must of been 1985? I was very nervous as I hadn’t ever dressed outside of my house, but the ladies that were running it made me feel very comfortable, like they took their time as I wasn’t sure how far I wantEd to go? Whether I should go full femininizaton or something a little lighter?… Read more »

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