Basic Makeup for Sissies


For some sissies, simply wearing panties or lingerie or even a full outfit of women’s clothing is enough for them. They enjoy crossdressing as a fetish unto itself, and that’s plenty for them. There is absolutely nothing wrong with that preference. Many men never go any farther than wearing panties or other feminine articles of clothing. For those who want to go further, our basic makeup for sissies guide is required reading!


There are plenty of sissy boys out there who want to be turned into pretty little sissy girls! This guide is for all of them.


It’s easy to learn to do your own makeup, and it can be fairly inexpensive as well. You just need a few important things to start with: concealer, foundation, powder, mascara, lip gloss. The rest can be added later.


Basic Sissy Makeup for Beginners


We strongly recommend that when you first buy your makeup basics to try them on yourself if at all possible. The color of foundation or powder can look vastly different in the package than it looks on your skin, so in order to the get the best shade, it’s best to try it on.


These five items are the easiest to pick out because they require no particular expertise in choosing colors that complement your skin tone. You just have to pick concealer, foundation, and powder that matches your skin color as closely as possible. You’ll also need black mascara, clear lip gloss, a brush for applying powder (the bigger and fluffier, the better), and perhaps some makeup sponges, if you like. Those will be the basics that you’ll start with. Once you feel comfortable with those, you can move on to other things, things that require an eye for color and a steadier hand, in the advanced section of this sissy makeup tutorial.


Let’s Start Your Feminization with Makeup!


Once you’ve purchased your five basic makeup for sissies items, it’s time to try them out! The first thing you need to do before you apply your makeup is to wash your face really well. Get it nice and clean, then pat it dry with a towel. If you have dry skin, you might want to look into getting a moisturizer to make your face look and feel better. (You can wear this moisturizer under your makeup.) Now, have a seat in front of your mirror, and let’s begin.


Begin by looking for any blemishes or uneven patches of color on your skin. You’ll want to apply a tiny dab of concealer to each of these areas and blend it well. You may use your fingers or a makeup sponge to blend. Next, dab a little concealer underneath your eyes and on top of your eyelids. This helps to brighten them up a little and, once we get to the more advanced makeup techniques, will give your eye makeup something to adhere to, which will help it stay in place longer. Blend!


Now that you’ve gotten your concealer on, what next? It’s time for foundation! Some people prefer mineral foundation, which comes in the form of a loose powder, but here at sissy school, we advise our sissy boys to use liquid foundation, as it evens out men’s rougher skin tones better and helps them look more feminine.


Grab your foundation, shake it, and then dab it on all over your face–forehead, nose, cheeks, chin. Then, blend it, much like you did with your concealer. Make sure to sweep your fingers or your makeup sponge upwards as you blend, rather than downwards, to fight the pull of gravity on your face. You don’t want to look old before your time, do you?


A quick word of warning: You may have heard before that you should put foundation underneath your jaw and chin or even all the way down your neck. We’ve found that it’s best to avoid this if at all possible because it’s too easy to stain your clothes this way. Besides, if your foundation matches your skin tone well enough, there’s really no reason to do it, anyway.


You’re Looking Like a Pretty, Pretty Sissy Now


Since you’re going along well, there’s no reason to stop now. Get your mascara out! Shake the tube well before you use it. Then, move the brush up and down in the tube several times to gather up plenty of mascara on the brush. Scrape the excess on the end of the brush off on the rim of the tube. Now, lean in close to your mirror and apply your mascara by stroking the brush over your lashes several times, from the base of your lashes to the ends. Be sure to put on several coats on both your top and bottom lashes, but don’t put so much that you cause the lashes to stick together in clumps.


Give your mascara a few moments to dry before going any farther. You don’t want it to smear all over your perfectly made-up face!


When you’re sure your mascara is dry, open your powder up and get your powder brush. It doesn’t matter if you’ve gotten loose powder or pressed powder; you’ll still need the brush. If you have pressed powder in a compact, you can just throw away the applicator that’s inside. We won’t be using it. Dip your brush in the powder and gather some up. Don’t get too much on the brush because you don’t want your powder to be caked on your face. Be sure to err on the side of caution here.


Brush the powder very lightly all over your face, including over your eyelids. If you’ve accidentally gotten a bit heavy-handed with it, use a facial tissue to wipe some of it away.


Only one more step! Get your lip gloss out and shake it like you with did the mascara. If you have lip gloss that is applied with a brush, move the brush rapidly in and out of the tube like you did with the mascara brush to get plenty of lip gloss on the wand. If you have roll-on lip gloss, just unscrew the top. Then, carefully put just a little lip gloss on your lips, just enough to create a little shine. Don’t glop it on too thick!


We’re all finished now! Take a good look at yourself. You’ve successfully advanced your feminization along by applying basic makeup all by yourself. After you get used to your basic routine, you may want to take a look at our advanced makeup guide for sissies as well.


Need One On One Help With Basic Makeup For Sissies? Call the Sissy Training Mistresses 800.730.3507