Welcome to your first lesson in Crossdressing School!

I’ve asked for you guys to tell me what you’d like to learn about first, and, since I got a comment asking about perfect kissable, fuckable lips, that’s what our first lesson will be all about! Rod asked for help with lipstick, wondering how much was too much, and which brand I recommend to minimize smearing when sucking a nice big cock. Well Rod, I gave you a short answer already, but hold onto your garters, because here comes the in depth explanation of everything lipstick!

Let’s address the first concern with lipstick: how to put it on!

I’m going to assume that if you’re on the internet reading this, then you know exactly how to use google to look up youtube videos explaining the mechanics of putting on lipstick. If you haven’t looked that sort of thing up, do so! I’m a big fan of using all sorts of methods for learning, and reading a written explanation is just one — watching an expert is another. Imagine me giving you a stern look here.

So, you’ve decided you want to wear lipstick, congrats. There’s more to fantastic lips than just grabbing a tube at the drugstore and slathering it on, though. My recipe for fantastic lips? Lip balm, lip liner, lipstick, and if I want glossy wet looking lips, lip gloss. Yes, four different products for one part of your face!

• Lip balm helps keep your lips moisturized and soft. No you should not use lipstick as lip balm, they do different things and lip stick can actually dry your lips out.
• Lip liner helps keep the lipstick where you put it. If your skin care regimen isn’t as good as it should be, or you skip the lip balm, or you’re dehydrated (and lots of people go through life slightly dehydrated), when you wear only lipstick, you get tiny cracks and feathering at the edges of your lips, and the lipstick creeps into them, resulting in lipstick out of bounds.
• Lipstick, lip stain, lip dye… all used to add actual color to your lips. That’s what they’re for, and that’s all they’re for!
• Lip gloss can be either clear or tinted; tinted, it adds color and shine, clear just makes your lips shiny. It does not moisturize your lips! Sometimes lip gloss is flavored — I think of those as a clever trap to get you to buy more lip gloss, because you’ll wind up licking your lips and needing to reapply. If you can train yourself not to lick your own lips, then flavored lip gloss can help make kissing more fun, but otherwise, I prefer unflavored.

Lip liner and why it’s vital.

Not kidding here, it’s really vital. Lip liner keeps your lipstick in place and prevents it from going wandering around your mouth. It also helps lipstick, uh… stick. Think of it like priming a canvas or other surface before you paint on it. The paint (lipstick) sticks to a primed surface better than to an unprimed surface, you use less of it, it doesn’t seep in as deeply, it doesn’t run as much… lip liner is primer for lips. The best way to use it is to outline your lips, starting with the cupid’s bow on the top of your upper lip. Draw that in, then the wings out to the corners of your lips, then the middle of the lower lip and out to the edges. After that, prime the surface by coloring in the rest of your lips with the lip liner.

Remember the 80’s, and how everyone’s lips were darker on the outside edges and then pale in the middle? That’s what happens when you use a dark lip liner and don’t color in the rest of the lips. If that look comes back into fashion, you’ll know how to do it, but for now? Freaking color in! Oh, and I prefer a neutral shade for lip liner, so it doesn’t change the color of the lipstick.Clinique’s Quickliner in Neutrally is my go to lip liner, and if they ever stop making it I’ll cry.

Smeared lipstick can be really hot.

So, I like gender play, as you all know. If you didn’t know that, surprise! Anyway, part of what I really love to do is to make people over, make them pretty and perfect and gorgeous, and then fucking wreck them. I love smeared lipstick. I deliberately buy the cheap lipstick for my sissies, because I know it’ll smear. All around their lips, down their chins, all over the cock or strapon I’ve had them sucking. I like that trace of trashy red, like sissy sign… a sissy was sucking this cock, and you can tell, because of smeared lipstick. I know, it’s a kink of mine.

Not everyone shares that kink, and that’s perfectly fine!

If you want your lipstick to stay on while you’re sucking cock, or drinking coffee, or going through your day, then you’re going to need something other than the cheapest red lipstick from the bargain bin. You’re going to need lip stain. Now, fair warning, they mean it when they say ‘stain’. If you need to be back to manly masculine man the next day, do not go for a stain or dye! Read the packaging, and be aware that when they say ‘long wearing’, ‘long lasting’, ’24 hour color’, what they mean is ‘this stuff won’t come off even if you exfoliate your freaking lips, not kidding, you’re gonna have this color for a while.’ I like Revlon’s Just Bitten lip stain — and yes, it says lip balm on it too. You can use it like a balm, but again, it’ll stain your lips pink. Their Colorstay lipstick is another deceptive one. Really really, it’ll stay and stay.

Alright girls, that concludes our first lesson in Crossdressing School!

Your homework, should you decide to participate, is to practice putting on your lipstick! Once you’ve got your lips looking fantastic, take a quick picture and go share it on the Enchantrix Empire, which, by the way, is a fantastic resource for folks who want or need support in their explorations of all things girly. The Mistresses over at the Empire love helping folks reach their full girly potential!

And, if you have any questions or things you’re wondering about as far as being a girl go, drop me a comment or an email and I’ll cover them in our next lesson.

Kisses!