Advanced Makeup Guide for Sissies


If you have not read our basic makeup guide for sissies, we strongly suggest that you do so before reading this guide. This tutorial is meant for those sissies who are already comfortable with doing basic, everyday makeup. If you’re not yet proficient in the basics, please learn those first. We don’t want to confuse you and cause you to give up the whole endeavor in frustration!


However, if you have read our basic guide and feel reasonably certain that you’re ready to progress a little farther in your feminization, then this is the place for you.


If you’ve made it this far, we assume that you already have your basic makeup: concealer, foundation, powder, mascara, and lip gloss. Now, we’re about to add some color to your collection. But first, we’re going to discuss your skin tone, hair color, and eye color. These things must be considered before you go to buy more makeup. Just like assessing your body type before you purchase sissy clothes, remember to be gentle with yourself as you evaluate your look!


The first thing you’ll need to know is if you have “warm” or “cool” skin. People with “warm” skin have yellowish or olive undertones in their skin. People with “cool” skin have pinkish undertones. Sometimes, you can tell just by looking at yourself which you have. But if you’re unsure, here’s an easy test: Look at the skin on the inside of your forearm. If the veins in your wrist and the bend of your elbow appear to be greenish, then you have a warm skin tone. If your veins appear to be bluish, then you have a cool skin tone.


As a general rule, colors like brown, yellow, coral, green, and warmer shades of red look best on people with warm skin tones. Colors like pink, purple, gray, blue, and cooler shades of red look best on people with cool skin tones. Which of these colors will suit you best depends on other factors, like hair and eye color.


Feminization Based on Hair and Eye Color


For example, a blonde, particularly one with light eyes, usually shouldn’t use colors that are too dark. They tend to look too harsh. Brunettes should generally stay away from colors that are too light to avoid looking “washed-out.” And redheads should avoid pink or colors with pinkish undertones because they tend to clash with red hair. These are merely guidelines, of course, not rules that are set in stone.


When it comes to eye makeup, here are some tips to keep in mind. Brown eyes look best with bronze, green, and certain shades of blue. Be very careful with blue, however! Light blue can look nice; electric blue can make you look like a refugee from the 80s! Green eyes look best with brown, peach, and certain shades of purple. Likewise, blue or gray eyes look best with blue (for gray eyes), gray (for blue eyes), pink, and purple.


With these things in mind, it’s time to go shopping again, this time for blush, eyeliner, eyeshadow, lipstick, and some more makeup brushes! If the thought of matching up all these colors makes your head spin, remember that you can always fall back on neutral colors like black, chocolate brown, camel, amber, white, ivory, and beige. They might not be quite as exciting as other colors, but neutral shades look good on everyone. You will also need a blush brush and eye shadow brushes at the bare minimum.


Sissy Makeup Enhances the Crossdressing Experience


Once you’ve got your colors all picked out, you can make your experience as a crossdresser even more intense with well-applied makeup. Begin by washing your face and applying your moisturizer, if needed, and your concealer and foundation, as described in the basic makeup guide for sissies. The next thing you’re going to do is put on your blush. Take your blush brush–which is similar to a powder brush, only a little smaller–and gather up some blush on it.


Where you put your blush is very important. You don’t want to look like an old lady! Start next to your nasolabial folds at the hollow directly beneath your cheekbones. Sweep your blush upwards at a shallow angle. Your blush should cross your cheekbones about halfway between where you started and your hairline. You should stop at your hairline and blend the edges a little.


When you’re satisfied with the way your blush looks, let’s work on your eye makeup. Brush a little powder across your eyelids and underneath your eyes to create a sort of primer for your liner and shadow. Close one eye and carefully draw a line on one of your top lids from the inner corner of your eye to the outer corner. Pencil eyeliner works best for this until you get used to applying liner to your eyes. Keep the line as close to the base of your lashes as possible. You may find it helpful to make several small strokes with your eyeliner pencil, rather than trying to draw one continuous line. Do this with your other eyelid, too. You can also line your lower lid if you feel up to the task, though many people prefer to wait until they’re good at lining the upper lid before trying the lower one! If you make any mistakes, they can be easily fixed with a damp cotton swab.


This Sissy Girl Is Looking Good!


Once your eyeliner is in place, you can begin working on your eyeshadow. You will need three colors of eyeshadow. Gently brush the medium shade across the bottom part of your lid, from the inner corner of your eye to the outer corner of your eye. Bring the color up almost to the crease of your eyelid. Next, brush the lightest color of eyeshadow all the way across your lid from the crease up to the line of your eyebrows. Finally, brush the darkest shade across the crease of your lid. Be sure to blend this well, so you don’t have three distinct lines of color across your eyelids. Each color should flow seamlessly into the next.


When your eyeshadow is finished, apply your mascara as you normally do. Now you’re almost finished! Go ahead and powder your face; you’ll also want to brush a light coat of powder across your eyelids as well, to “set” your eye makeup into place.


This leaves only your lipstick to put on to complete your fully made-up face. If your lips are chapped or unusually dry, you might want to apply some sort of lip balm to soften them before you put on the lipstick. Allow a few minutes for your lips to soak up the balm. Then, begin by applying a light coat of lipstick along your bottom lip. Try not to go outside the natural line of your lips, but if you do, you can always come back and fix it later. When your bottom lip is coated in lipstick, do the same with your top lip. You may put a very light coat of lip gloss on top if you want extra-shiny lips. Be careful not to put too much and smudge your lipstick!


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