Tag Archives: makeup

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.
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The Cost of a Bad Makeup Day

bad day

Getting all done up in full makeup is a pretty big investment on two fronts, or so it is for me. Makeup isn’t cheap, and it takes a lot of makeup to transform Gabe’s rugged man-face into the soft and feminine face of Gabrielle. It also requires significant time to get all that makeup properly spackled on and detailed just right. Therefore I have to plan ahead, making sure that I have enough makeup on hand and a window of opportunity available in my busy life.

Unlike many genetic women, applying makeup isn’t something I get to practice on a daily basis. Sometimes it doesn’t quite turn out right and there’s a price to pay.
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The Battle Scars of Crossdressing

Homer Simpson mowing the lawn in a dress

While examining my face closely in the mirror last night, I took a good look at all my new scars. They weren’t there a year ago, but now I have several of them scattered about. Some are more noticeable than others but they all stand out like a sore thumb to me. What caused these battle scars and why the picture of Homer Simpson mowing his lawn in Marge’s Sunday dress?
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Who’s That Desktop Wallpaper Girl?

Gabrielle desktop wallpaper at work

I often tell other crossdressers that I look so different en femme, fully made up, that no one (who knows my man-side) would ever recognize me if they saw. To test this a little, I changed my work-place desktop wallpaper to a close-up of Gabrielle’s face. The photo above is of my dual wide screen 22″ monitors at work. Guess what people are saying…
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