X
Hey, lovelies.
I think it’s really important to be honest about where I’m at with makeup. I’m not a pro. I’m not trying to be some beauty influencer. I’m just a regular person trying to learn how to look a little more like the woman I feel like inside. Makeup can be overwhelming, especially when you’re new to it, but that’s okay. We all start somewhere—and this is me, starting out loud.
Note from Michelle:
This post originally appeared on my old blog, Crossdresser Chronicles. I’ve moved it here because it still reflects an important part of my journey. Some details may be out of date, or lightly updated to fit where I am now.
👉 Read more about why I brought these posts over.
Where I’m At
Right now, I’d still call myself a beginner. I’ve only done full makeup a handful of times, and honestly? Most of the progress I’ve made has been thanks to AI pointing out what I’m doing wrong. I feel like I kind of understand the basics—enough to tell when something isn’t working—but not always enough to know why.
What I’m Working Toward
I’m not trying to look dolled up or like I’m heading to some fancy dinner. That’s not the goal. I’m not even trying to look sexy—truthfully, I don’t think I can pull off sexy. I just want to look normal. Casual. Like any other woman out running errands. I want to learn the kind of everyday makeup most women wear without thinking twice. Something simple, soft, and effective enough to hide the parts of me that still read “male.”
My Current Challenges
My two biggest struggles right now are figuring out which products actually work for me, and learning how to apply them properly. My foundation and concealer are both a bit off—they don’t quite match my skin tone, and it throws everything off. And don’t even get me started on eyeliner. That’s a mess. I want to be able to do it right, but it’s definitely still a learning curve.
What I Am Good At
It’s not all bad, though! I actually think I’m pretty decent at blending. My mascara game is solid, too. And most importantly? I feel like I do manage to make myself look more like a woman. It’s not seamless yet—but it’s getting there. And every time I do my makeup, I feel good. That’s what matters most.
Final Thoughts
Makeup isn’t about perfection. It’s about expression, and learning, and finding what makes you feel good in your skin. I’m still figuring all of that out. And if you are too? You’re in good company, babe. We’ll learn together.
3 Comments
Amanda · July 17, 2025 at 8:32 am
Ahhhh, the dark art of makeup application! I’m very long sighted so everything close by, in particular my reflection in the mirror, is just a blur without my glasses on and, of course, eye makeup requires removal of glasses.
One trick I learned with eyeliner is to use a pencil and close your eyes over it so that it is sandwiched between the upper and lower lids, then move the pencil backwards and forwards to apply it. Any overspill onto the lower lid can be carefully blended with a small brush and, with a bit of luck, the waterlines will have a nice coating of eyeliner without it looking like it was applied by a five year old.
More than that, though, and I’m nowhere. I’d love to be able to get a nice winged eyeliner effect but I don’t think I have enough life expectancy left to get to grips with that.
Michelle · July 17, 2025 at 11:58 am
This is such a clever trick! I’ve got some extra time to myself this weekend. Definitely going to be giving this some practice. I swear, eyeliner feels like it should come with a warning label. I’m still in the “take a deep breath and pray” stage.
And yeah… winged liner? I’m convinced that’s some kind of witchcraft. It seriously makes me feel less alone knowing I’m not the only one wrestling with this stuff. 💖
Amanda · July 17, 2025 at 1:37 pm
Just be careful with the pencil sharpener and make sure you pick up the right pencil – the point gets dangerously close to the eyeball!