Here’s a little story about my very first trip to a make-up store as a male.

I slowly walked past the store I wanted to enter. It was a high-end makeup store full of people, so I kept going to the food court and had a coffee and relaxed for a little bit hoping the place would be much less crowded on my next attempt to enter the shop. After finishing my coffee, I went back to the store. It was still full of people. Just because it’s a Saturday afternoon and the mall was packed full of shoppers, doesn’t mean the store I wanted to enter had to be busy! This time, I made a quick pass by the shop and turned around and headed back to the coffee shop for another coffee. Fortunately, I like coffee.

There I sat with coffee in hand again. Well not really in hand but rather in a paper cup. I was feeling sorry for myself for not having the backbone to go into the store, be it busy or not. I started thinking about what I could say to one of the salesgirls when old chicken little me finally got the balls up to enter the store. “Hi,” I could say to the salesperson. “I’m here to pick up some stuff for my wife.” Wrong. The salesgirl would see through that fabrication in an instant. So I thought, “Hi, I’m here to pick up some makeup for my girlfriend. Her birthday is coming up next week.” Double wrong. I’m sure they’ve heard that one at least a million times and I’d blow that cover story the instant they asked me what type and color makeup she wore. “I know,” I said to myself. “I’ll tell her the truth and hope she doesn’t laugh me out of the store.” Ha-ha, like I’m going to say that. Yeah, like I’m going to tell here right from the get to that I’m a cross dresser and I’m in there to get some help purchasing makeup for myself! Then, in the middle of a brainstorm, the little idea light flashed on, and I had it. “My wife’s birthday is coming up,” which is not stretching that little fabrication too much, “and I would like to look around.” An oldy but a goody but still not sure if I was going to use that line either.

By this time, my coffee was cold, but I finished it anyway. Inspired by the power of my last thought, I got up and made my way to the store for the third and final time. Heaven forbid someone I know would be in that makeup store or see me entering the makeup store from the main hallway of the mall!

En Femme Style

There I was, standing a few feet away from the store, looking in and seeing a crowd of people still in there. “It’s now or never,” I said to myself, adding, “You can do this,” so I finally got my courage up and just walked right in and immediately froze in my tracks.

Talk about a different environment! There had to be at least a gazillion different products on display. The store must have been extra warm as my face felt like it was on fire. I felt embarrassed to be in that store by myself without my wife. Especially while in there shopping for makeup for myself instead of makeup for my cross dressing self!  I’d wager my face was so red that it would have made a firetruck look pale! Then the nightmare hit me. One of the salesgirls, early ’20s I would guess, walked right up to me and said, “Hi there I’m April, can I help you find something you’re looking for?” I am embarrassed to say I must have looked like the proverbial deer in headlights and was still a shade or two of red as I said absolutely nothing! After I started to breathe again, I realized that a vocal exchange of information was required at this point, so I replied in a shakingly timid voice, “Hi.” I’m sure a glass broke somewhere as I said that single word in such a high voice.

April, who was just as sweet as she could be started asking me a few questions, most of which I could not answer as this makeup stuff was all so new to me. I think she realized rather quickly who I was in the store shopping for. April had a warm, friendly smile on her face and said to follow her and let’s get started with some foundation makeup for you. Within a matter of minutes, she had me so relaxed that I was sitting up in one of their chairs as she was applying some samples of makeup to my face! People were passing by in the mall corridor right by the window and plenty of shoppers were still in the store. But by this point in time, I didn’t care. It was just full speed ahead with my makeup artist named April who really knew what she was talking about and doing!

    Nobody paid the slightest bit of attention to a guy sitting in a chair having makeup applied! Absolutely nobody! It was just as if a girl was sitting in that chair having makeup applied!

Crossdresser Superstore

And that is just the message I’m trying to drive home today in this article. Nobody cares in today’s world if a guy is in a makeup shop shopping for makeup! And if somebody does look at you funny or says something a little weird or inconsiderate, don’t be angry or embarrassed. Just be relaxed and comfortable in your own skin. We are living our lives to the fullest, while anyone that would comment negatively or rudely is living a sheltered and most likely dull life. Perhaps that’s the way they want to live. We want to be free and explore our feminine sides and feelings and be open to express ourselves freely these days!

So, when it comes time to starting your journey into the wide world of makeup, don’t be nervous or scared on your first visit to a makeup shop dressed as a male shopping for your own makeup. Walk right in like there like you own the place and enjoy the pampering you’re going to receive from the salesgirls. After today, I’m absolutely positive there are friendly, helpful, and extremely polite salespeople like April working in all these makeup stores who help cross dressers out on a more than regular basis. So just relax! Trust me, you’re not the first cross dresser they’ve helped find just the right makeup for you and you’re definitely not going to be the last as well!

There is one thing to remember. Have lots of money or a credit card or two if you’re going into a high-end makeup store as this one because you’re probably going to need it! I came out with a pre-makeup moisturizer, a foundation, and a filler for my lines and ended up spending over a hundred bucks!

Was it worth it? Absolutely. Was the product top quality? Yes. Will I go there again? You bet I will thanks to the way I was welcomed and treated by April!

So next time you’re about to enter a makeup store such as Sephora or Ulta dressed as a guy and shopping for makeup for yourself as a cross dresser, just walk right in like you own the joint and look forward to being attended to and pampered by the salesgirls in that store. And don’t be shy about telling them you’re a cross dresser! Those girls help several cross dressers each week. Some admit to being a cross dresser and some don’t. I suggest you go right ahead and tell them up front what the truth is about yourself and you’ll feel much more comfortable right after that very first sentence of truth! Trust me on this one!


  • Have you ever gone into a makeup store dressed as a guy looking for makeup for yourself and if so, how did you feel the very first time you did just that?
  • How did the salesgirl treat you after you broke the news to her about you being a cross dresser and you were looking for help finding specific types of makeup you needed for yourself?
  • Were you as anxious and worried as I was on your first time entering a makeup store dressed as a male looking for assistance for makeup advice and products for yourself as a cross dresser?

Thanks for taking the time to read my article and please take the time if you’d like to respond in any of my questions posed above!

Sincerely, Kendra Carter





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    Kendra Carter

    Hi everyone! After too many years it's time to explore my feminine side, only this time seriously. I tried before but without a gentle helping and guiding hand I gave up, but the interest was never buried. So I'm collecting a wardrobe, (clothes and shoes are so expensive,) and will have to check out how to do my own makeup. I'm looking forward to chatting with you all and should you have suggestions for me, please don't hesitate to pass them along. I'll update this a bit later on. Thanks, Kendra!

    Latest posts by Kendra Carter (see all)

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    Bianca Everdene
    Trusted Member
    4 years ago

    Hi Kendra Thanks for sharing your story, and well done for overcoming that enormous psychological barrier, and just going for it. I still vividly remember my first time. I heard on this site that Estée Lauder doublewear foundation was good to cover any signs of facial hair after shaving, so hatched a cunning plan!!! It’s expensive, and I wanted to get the right shade. There are Estee beauty counters in a chain of large stores here in the UK, I decided not the local one (may be seen and recognised), so decided to make a day of it and went… Read more »

    Daisy Marie
    Active Member
    4 years ago

    Thank you for sharing your makeup adventures, Kendra! Two weeks ago, I took the same steps as you and finally entered into a Sephora store in São Paulo, Brazil. Surprisingly, nobody asked me whether I needed some help. I didn’t purchase anything exactly because of the price tag, however I took some great ideas and knew better some brands like MAC and Lancôme. Last Friday I went to another Sephora store, close to the office where I work. In that store, at least three girls offered help, but I was there just taking a deeper look. Perhaps the next time… Read more »

    Kathy LaDonna
    Trusted Member
    4 years ago

    Love the article. What courage over fear and what a reward. Some day. I’m older and fear friends and family. Thank you.

    skippy1965 Cynthia
    Trusted Member
    4 years ago

    Great story Kendra -thanks for sharing. As with most situations, confidence and a smile will carry the day most times!

    Deborah Sullivan
    Trusted Member
    4 years ago

    Oh I remember so well my first visit to Ultra and the butterflies I had as you described. Was a thrill though even with the store half full. Walked out spending more than I planned to but have been back several times.

    Alice Black
    Active Member
    4 months ago

    I have not had the nerve to go in Ultra or Sephora. But reading your article does inspire me – so one of these days I will do that.

    Darcy Grigsby
    4 months ago

    Another way to handle this is (at least for Sephora) the have a personal shopper program that you can book on their site. During the booking you have the ability to type notes and that is the chance where you can introduce yourself as a CD. That way they know what to expect when you show up and there is much less awkwardness.

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