I did it (/am doing it)

[dolovewell]

A lot better without the glasses!

Honestly you have a lot going for you.

I think your eyebrows could be in a more feminine shape, though. I know its a fine line to straddle to have feminine enough brows for when you dress and masculine enough for when you are in male mode, but its doable. I think your eyebrows here read androgynous at best. Your eyebrows actually frame your whole face, which is why I say if nothing else, eyebrows.

I wouldn't line the entire lower lash line. If you are going to line it, I'd stop halfway. You have big eyes, you don't want to close them off! I too have big eyes, and I used to line the lower lash line the whole way. Then I got advice from GGs saying don't, because I have big doe eyes and closing them off will ruin the feature. Check out the pics on my Flickr https://www.flickr.com/photos/thegirldownthehall/ and notice how I line my lower lash line. I generally dust a brown eyeshadow half way, blend it out, and apply a small smudge of brown eyeliner on the outer half of the lash line. It gives it a soft look that defines it without closing it off. Also since you have big eyes, tightlining your lower water line with a white(or light) eye pencil will bring it out and brighten it up even more. I do this, using the NYX Wonder Pencil in Light. Play up your best asset. I would only line your entire lower lash line if you are going with a really dramatic, sultry eye look.

As far as contouring, I wouldn't use a crayon personally, those have a higher learning curve and if you haven't contoured before, can be very unforgiving and heavy because of the blending needed. You need to be good at blending first. I'd go with a powder. I use NYX HD Blush in Taupe for contouring, its cheap and gets the job done. I first apply my bronzer/blush/highlighter, then apply the contour powder on areas I want to contour, generally the hollows of my cheeks, my jawline, my temples, and my nose. Nose is the big one. Your nose, like mine, is masculine and contouring it will make it slimmer and feminine. Contouring is something that takes practice, especially when it comes to blending, but I think its necessary as MTF crossdressers to slim up and demasculinize our faces. Lots of YouTube videos on contouring. Look up contouring for beginners.

[ElleStreet]

I'm not too fussed about my eyebrows in boy mode, But I'd be too scared to go and get them done, it's a big step y'know ?
I'll try the eyeliner thing next time I dress. I guess, being new, I just naively assumed more makeup = more feminine (within limits obviously)

I'm still awful at applying eyeliner and eyeshadow which is why I'm looking upset in that pic, I had just picked a fight with my eyeliner and lost.

Ermmm... I've never heard of bronzer or highlight before. are they important? Also is there anything else important I may not know about?

Since you said it's better without the glasses here's anothe pic I wasn't sure about putting up (it's a little embarrassing)
http://imgur.com/3Sz5lKX

[dolovewell]

Waxing eyebrows is a big step. I didn't do it until I was about 2 months in, but it was a great decision. I get mine waxed about once every 6 weeks, and maintain in between. I just show them a pic of what I want my brows to look like.

With eyeliner, the top lash line always gets lined for me. I, like you, would line off my lower lash line completely. I did this until I made a post to the MakeupAddiction subreddit on reddit, asking for general advice. I got about 1000 comments giving advice and I had to take a week off just to digest it all. The most common piece of advice I got was about my lower lash line, saying don't close it off! Yes more makeup looks more feminine, but makeup is about accentuating your features, especially your best ones.

Applying eyeliner and eyeshadow is not easy. It takes practice. For eyeliner, I use a gel eyeliner and a flat angled brush to make it easier. It's more forgiving with gel than liquid or a pencil. Brown gel eyeliner is ideal for beginners, as its very forgiving and good for more casual daytime looks. I also have a black gel eyeliner I use when I want a more dramatic look, but its less forgiving than brown. Eyeshadow is also something that takes practice. For eyeshadow I recommend investing in higher quality shadows. I use a LORAC Pro palette myself. It was $44 but the shadows are very pigmented and silky smooth. The drug store/cheaper shadows are more chalky and less pigmented, meaning they are much harder to apply and blend. Eyeshadow is all about blending. Your eyeshadow will only look as good as you can blend it.

Bronzing and highlighting is very important. I do not think its optional, especially for MTF crossdressers. I was certain you weren't using them in your pics. The thing is, with just foundation/concealer/powder, your face will look evened out skin tone wise, but flat. Bronzing/highlighting adds shape, color and dimension back into your face. I sweep bronzer in the hollows of my cheeks, my temples, and my jawline. I sweep blush on the apples of my cheeks and down toward the ear, and then highlight on the height of my cheekbones and the center of my forehead. Bronzing and contouring is not the same thing. Bronzing just adds a sun kissed bronze back to your complexion where it would naturally be without makeup. Contouring is meant to create definition and shadows as well as downplay areas you want to downplay. I contour the hollows of my cheeks on top of the bronzer for more definition. I contour the hell out of my jaw line, especially around the jaw muscle in the mouth, to downplay my masculine jaw and make that area look smoother. Finally, I contour my nose to downplay it and make it look slimmer.

This is pretty much my routine:

-Shave
-Moisturize
-Primer
-Orange Concealer on beard area
-Foundation
-Eyeliner
-Eyeshadow
-Mascara
-Undereye Concealer
-Pressed Powder
-Eyebrows
-Lips
-Bronze/Highlight/Blush
-Contour

Moisturizing is really important, as men we have dry skin so without moisturizing we will just soak up all the moisture from the makeup and our faces will look fake and cakey.

I do under eye concealer after mascara and eye makeup because if there is fallout from my eyes that falls onto my undereye area I am not messing anything up