Wearing Makeup: The First Time and Now

Gabrielle Hermosa (Dec. 2009)

I’ve been crossdressing since the age of 3 or 4, but it wasn’t until December of 2008 that Gabrielle finally got her face. The picture above was taken a couple of weeks ago, on the one year anniversary of my first time in full makeup. It’s not my best head shot, but certainly displays a vast improvement from a year prior in terms of looking more feminine up close.

After a lifetime of keeping this aspect of my life a carefully guarded secret, it was around this time last year (add a couple of weeks) that I was finally (fully) out to my wife. It was that same time, after months of planning, that my first ever feminine makeup transformation took place. The fabulous Mrs. H. agreed to take care of business for me. With years of experience doing her own makeup, and very well, I was sure to look gorgeous when all was complete… or so I initially thought.

I remember sitting in the bathroom while my wife carefully applied the makeup. She had me positioned so that I could not watch the process in the mirror – wanting it to be a surprise until finished. For decades I had waited for this moment and it was finally happening. This kind of anticipation is something that only another crossdresser (who also happened to wait far too long) can truly understand.

Mrs. H. smiled and giggled at times while applying my makeup. The process was pretty amusing to her, and she rather enjoyed it. Foundation, eye shadow, eye liner, blush, lipstick… and the wait was over. After a lifetime of self-denial, it was time to face my feminine side in the mirror – the woman within that had been unfairly locked away all my life.

It is hard to find the proper words to describe how I felt after coming face to face with “Gabrielle” for the first time in the mirror. To quote the fictional, but wise character of Spock, “…having is not so pleasing a thing, after all, as wanting. It is not logical, but it is often true.” The context in which I use this quote differs from how it was used in the Star Trek episode “Amok Time”, but seems fitting in light of the great disappointment experienced that moment.

Although it felt good to finally be in full makeup as Gabrielle, I clearly looked like a man wearing makeup and not at all like the beautiful, feminine face that I mentally envisioned for so long. Most of the photos taken that day looked awful. My desire was to look as female as possible and not like a man wearing makeup. It was quite a let-down. I couldn’t help but wonder how much better I might have looked had this moment arrived many years sooner on a much younger face.

Gabrielle #4The following day, we gave it another try. Some lessons were learned and a slightly different approach was taken this time. It fell short of what I hoped for, but was a welcome improvement. My face looked more feminine and less rugged. Click the thumbnail to the right to see the first-ever photo as Gabrielle I shared online (originally published on January 1, 2009).

Unfortunately, I’ll never know how beautiful I might have looked as Gabrielle in my teens or twenties. Being genetically male, my face is aging as such. Thought it does not look terribly old by any means, it does look fairly rugged and quite male. If you’re a young crossdresser, closeted or not, I suggest you begin experimenting with makeup if you haven’t already. Younger faces have the potential to look more feminine, and of course that much more attractive.

The silver lining is that I’ve gotten better at doing my makeup over the past year. Like many before me, I discovered that sticking with it and refining technique can greatly improve the end result. My preferred style isn’t exactly a modern, trendy approach. I love thick, black eyeliner, darker eye shadows (applied in an 80’s-ish fashion), bold lipstick, and sometimes a little too much blush (thought it is unintentional with the occasional excess blush).

Coming up
In my next post, I’ll be revisiting my first-ever published photos as Gabrielle. It was just over one year ago that I first ventured online as my feminine-self. A couple of then and now comparison photos were taken to celebrate. I hope you’ll join me while I reminisce and look back at my first baby steps into the world as Gabrielle… if only via the internet in the beginning.

Share your experience
At what age did you first start wearing makeup? How did it turn out your first time? Did you have any help (from a friend, girlfriend, or wife) getting started? Do you follow the latest makeup trends or do your own thing? If you’re the mother, sister, wife or signicant other of a crossdresser, have you helped someone get started or perhaps still do their makeup for them? Please take a moment and share.

9 thoughts on “Wearing Makeup: The First Time and Now”

  1. Lucky you eh? :D

    See also: “it is better to travel in hope than to arrive.” :) I think it’s difficult for something you’ve been yearning for, to live up to the level you might build it up to.

    Make-up is tricky at the best of times and I think we’ve all had those days when it just doesn’t sit or feel right.

    I remember trying on lipstick when I was quite young – probably 8 or so – but I didn’t try a full face of make-up until I was in my mid to late teens. With two sisters in the house, there was never a shortage of magazines to learn from :) Not that it meant I was any good at it :D

    You can read all you like, but there’s no subtitution for actually doing it :D

    1. @ Lynn – Another fitting metaphor, Lynn. :) You’re absolutely right with calling makeup “tricky”. I have good makeup days, and I have had plenty of bad makeup days. :(

      I’m envious – you got to see yourself in full makeup in your teens. How I wish I could travel back in time and see myself in makeup at that age! Bet I wouldn’t have had to cake it on so thick back then, either.

      @ Gina – I was in several plays during my (grade) school years. I never played a female character, but the stage makeup that they used on me did give my face a bit of a feminine look (up close). Oddly enough, I didn’t care to look feminine back then – I was too busy hating this aspect of my life at the time and wishing I could just be “normal” (note the quotes). You also got into female at a much younger age than I. I waited far too long to allow myself the experience. Better late than never, right? :) There are those who deny who they are their entire lives and that is very sad.

  2. Gabrielle, While I did quite a bit of experimenting with Mom’s lipstick as a youngster, it wasn’t until college while performing in plays that I got experience with a wide variety of “looks,” beginning with a “blank canvas.” It was those experiences that I saw the potential for a more feminine face. If only I had the nerve to pluck my eyebrows back then! Now, in my dotage, it’s more or less a “warts and all” approach; lining plucked brows, a little eyeliner and bright red lipstick.


  3. I’m envious – you got to see yourself in full makeup in your teens

    Please don’t be :) Younger doesn’t mean better and with age, comes experience… and credit cards :D

    1. You make a good point with the credit card thing, Lynn. lol Speaking of which… my wife surprised me today with a new pair of stylish winter boots. :D Wear and enjoy now… pay later. It’s like magic… until that bill arrives in the mail! :o

  4. Though I am still not good at putting on makeup; I did put on makeup as a child, preteen, a couple times as a teenager, and my tweens (early 20s). My issue then was my body. I guess there might be truth to younger face being easier, I don’t remember rightly… maybe I focused on the negative then. However the older body… my older body has more curves. And I do enjoy that more. I guess it is a trade off in a sense.

    1. I’m not all that skilled with makeup either, Erin P. I do ok when I take my time, but the problem is that it does take a good deal of time to do a good job. Much faster than I was back in the spring (when I started doing my own makeup as opposed to my wife doing it for me) but still very slow in comparison to a genetic woman.

      I think my teens and early 20’s body would have been excellent for Gabrielle… much better than today because I didn’t have bulky muscles (bulky for a female, anyway) to try and hide back then. My legs look better today, but my body as a whole, looked more feminine in my teens and early 20’s.

  5. My first “real” makeup experience took place on a Halloween with the help of a former GF. I thank her for the help then, but my thought was “this will never work”. I don’t blame her for a bad job though, what happened was A: a slight reluctance on her part, B: never having dealt with making up a male face before, and C: using her colors on me. Long story short, I pretty much gave up on “passability”.

    Since that time, I have learned quite a lot. My wonderful GF was not only accepting of me, but basically put me on the path to venturing out. She helped teach me the basics by applying makeup (my colors this time) on herself and coaching me side by side at the mirror. This helped to teach me not only the “how” but also the “why”. I have since tried to practice as much as possible (that means nowhere nearly enough) and can confidently do it myself and drive over to pick her up and go out for the evening. That does NOT mean that I am good at it, just good enough for starters.

    I like your makeup G, you do a good job and your lips look fantastic in the new pic. Keep up the good work and thank you for this post.

    1. Thank you for your kind words and sharing your experience, Erin K. :) It was very cool of your girlfriend to help you get started and offer side by side lessons like that. There’s nothing easy about getting started and those early results can really be discouraging. I think that’s an important point to share, though.

      I don’t have the opportunity to practice as much as I’d like to, either. That’s why it takes as long as it does to complete the job and the results, although far better than when I firt started, are still hit or miss.

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