Does My Makeup Make Me Pretty?


When I see the term passing, I wonder does this mean in public everyone thinks I am actually a biological woman or that they accept who I am without questioning “why is that man dressed like a woman?” Certainly we do have the desire to pass some sort of mythical test to blend in and to have everyone identify us as female. Not only is it about our mannerisms being feminine, dressing appropriately, and our perception of ourselves; makeup is a key factor in helping us achieve our confidence as well.

Something I picked up from my daughter-in-law that really made me think. She passes time – you know those bored moments when there’s nothing going on and nothing to do –by watching makeup YouTube videos and trying out the techniques and looks that she likes. Sometimes she will do 2 or 3 different looks in one sitting.

 So that got me to thinking, how do biological girls get to their signature look, or say their everyday look? I’ve discovered that it is all in practice and peer reviews. Most girls start at around 12 or 13 (some earlier), parent approved or not. They learn from one another, and critique one another. By the time they hit their 20s they’ve pretty much nailed down the signature look and by the time they hit their 30s their makeup style and technique are pretty much second nature. This phenomenon is not limited to the internet YouTube generation. This has been going on since the advent of the modern teenage girl. I remember my mother talking about when she was a teen in the 40s. So my guess? Since the popularity of girls wearing makeup.

 The difference for many of us in the transgender/CD world, is we don’t know where to start, we don’t know what might look good, and many of us start much later in life without that female influence. What we need is trial and error time, critiques from our peers and women who’ve been at it a while, with lots of practice to get to the point where it becomes second nature. It’s much like dressing, we find what fits, what styles look good, and discover that while heels make us look very sexy, they’re not practical for everyday use. Makeup is really no different; there’s the day look (you’re everyday look), out clubbing look, the sexy sultry look, the possibilities are endless. But like all girls we need to figure out what look is appropriate for the occasion, so you’re not sticking out like a sore thumb by looking sexy and sultry at the grocery store.

I’ve been trying my daughter-in-law’s technique for about a year now, granted not diligently. However, more recently I’ve been experimenting with eye shadow almost every night. The look I have on my profile picture took a lot of doing, but now I’m much faster and getting better at it. Still can’t do eye liner worth a dam, but it’s best to tackle one thing at a time.

 My daughter in-law came over to hang out the other day, so I decided I’d do some makeup and see what she thought. Before she got here I put on foundation, a little blush, and did a simple day makeup look I got from a Lancôme video. I had no wig, and was dressed in my male attire. Much to my joy she was very impressed with my look and said I look very nice.

 So there it is ladies, if you can impress the girls, you’ve got it down. The key to success like any art is practice, practice, practice. 

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Darcy Bainsley

I love expressing my femininity, everything from just the subtle things that only I know about, all the way to all dolled up and out on the town. I try to focus on enjoying small triumphs and the little things in life that make me happy and feel pretty.

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Ian Toddjulieta navaTalhia SweyCloughieDDwight Richardson Recent comment authors
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How very true Darcy, I was terrified of doing my makeup and still are to a certain degree, although I’m quite happy doing my everyday look and quite quick at it now. I struggle a bit with my special look especially my eye shadow and lips, just can’t seem to get them right, but I’ll keep on practicing and I’ll try watching YouTube lol.
Thanks for the advice Darcy


I’m still terrified of doing my make up seem to spend hours trying and not getting anywhere


Ru Paul has great tips to help you with your skin, makeup, and all things girl..

UTUBE yes sweetie UTUBE


Eyes….that is my focus for next few months…..i’ll worry about foundation later

Billy mcglathery
Billy mcglathery

It hard to good help with learning how to put on makeup I went to Ulta and they taught me a lot plus I think the technician was as thrilled as I was and I look totally hot when I leftand where I am today wearing full makeup all started when I was younger with the lipstick I still love lipstick to this day I said you never can put on too much lipstick and lipgloss but maybe that’s just his naughty girl side of mekeep on putting it on nice and thick good night Merry Christmas I love every… Read more »

Dwight Richardson
Dwight Richardson

Hello all you hottie , I am just 7 months of trying to accept and mold myself into a lovly crossdresser I have bought some nice c cup breast forms and like to go out to gay bars dressed up . but my makeup skills need work its fun trying new styles and I love going out shopping for high heels and dressed and different wigs. Well got to go its makeup time Love Dedi

Cloé (CC)

Love this topic and the comments all have made. The power of makeup was lost on me until I started to try it about a 8 momnths ago. Utoob is my advisor, but I find it overwhelming sometimes. My wife is uncomfortable helping, but did give me the best advice so far. “Use just a little and blend it in, you don’t want it to be too noticeable”. Well damn if she wasn’t right, but it took me a long time to figure that out. I had been so focused on covering up the naturally dark circles under my eyes… Read more »

Talhia Swey

Makeup is a great factor, for females and “males” as well, a process and is rules to it, and like most things it takes practice, tutorials and advice from peers will make this journey a bit easier, it may seem some times, most times, constructive criticism from others a bit harsh, but one must learn to know the difference between constructive and plain bullism, bottom line for me, practice, learn the dynamics and rules of the game, makeup is not the enemy, is an ally, have fun with it, my best friend and tutor said to me once, is no… Read more »

julieta nava

el maquillaje lo he realizado desde muy chiquita, lo que si he notado es que cuando no lo practicas pierdes mucha habilidad, como vivo rodeado de mujeres, he aprendido cuales son las tendencias de moda, y cosas si desde los 80 hasta la actualidad, y conforme pasa el tiempo se hace mas dificil, por que los maquillajes no se ven igual y ahora hay que aprender maquillaje para mujeres maduras y todo lo refernte a hidratacion y cuidados de la piel me encanto esta seccion y com dice aunque yo he aprendido de muchas mujeres aun asi cuensta mucho trabajo… Read more »

Ian Todd
Ian Todd

Hi I find the makeup is the most thing to get looking perfect. Otherwise you’ll look like a man in a dress with makeup on
I’m trying to master it and I will win in the end
It’s just learning how to do it properly.
Otherwise trying to be hairless

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