We have essentials for your crossdresser makeup and feminization transformation. Any cis woman goes through lots of different styles. A trans woman, girly girl, sissy or crossdresser will also experiment with various styles and fashions. Don’t be afraid to experiment! It’s part of being feminine — yes even if you buy something that you end up hating — it’s all part of your feminine journey.
Welcome to The Weekly Hot Spot: kink conversation, BDSM advice, insight from he worlds of Distance Domination and phone sex. We are your hosts: Mistress Delia and Ms Olivia.
Today’s topic: Crossdresser Makeup – feminization, transformation, sissy style and so much more!
Delia, I’m so excited to do this — we’ve been talking about doing a specific podcast on feminization makeup for some time.
Delia: We really, really have and I think that both of us absolutely the feminization and makeup and I personally like makeup. For me, I’m a makeup fan and I love it for my callers too because it makes a statement and we’ll just get into so, so much about everything that has to do with pretty makeup and feminization. I even have written blog posts about creating a crossdresser makeup kit, so we’ll get into everything. Makeup and makeup kits in this podcast.
Olivia: We are both obviously cis women, we’ve been wearing makeup for ever. I used to be a professional photographer and makeup artist. And so we’ve got all kinds of tips for all of the femme girls.
But first, now this is super, super important. Before you get to your crossdresser makeup application, let’s lay the foundation for the foundation.
Getting the perfect shave for male to female transformation
Okay, so let’s talk about the cross-dresser guide to getting the perfect shave. And I love this particular one because it has step-by-step instructions. What do you think of this one?
Ms Delia: I think that the article that we read is absolutely perfect. The tips were from like what one to 12. I think there were so many good things and, and I love them because a smooth shave in my opinion is just so important. With your skin smooth, you can experience all the tactile sensations that you just don’t get if you have hair. There’s nothing, nothing, nothing like freshly shaved skin to make you feel pretty.
Olivia: Now I was originally talking about just the face, like eliminating the beard, smoothing out your facial skin. But listening to you, you made me think of smooth skin all over. So I want to suggest for all of the girly girls out there, why don’t you get nice and smooth all over? Think of shaving as making your entire body very smooth and feminine girly skin, right?
Delia: Girly skin is the best.
Primer starts your crossdresser makeup
Olivia: So once you have that beautiful smooth girly skin, let’s talk about primer and beard cover.
Any feminine makeup tutorial starts with foundation. I don’t care if you’re a crossdresser doing makeup or if you’re a cis woman or a drag queen or even a cis male who is an actor wearing makeup. It always starts with foundation.
And that can be especially important depending on beard growth, acne scars, any little cuts, any imperfections. So Delia, do you recommend primer? And if so, what kind?
Delia: I actually do recommend primer. I have, I think it’s Laura Mercer, a makeup primer. It’s a very nice one. It has SPF in it, so no sunburns, no sun damage. And I like to use that for my day looks. I tend to use a heavier like concealer and foundation for night looks, but I think for day primer makes my makeup just look really smooth and soft and and and polished. It gives me kind of that flawless skin that I think anyone who puts on makeup wants. So I do like primer very much.
Olivia: You bring up a really good point about the difference between day makeup and evening makeup. I think when people hear something like a primer or concealer, they’ll think, Oh my God, you’ve got a Kabuki mask going, you know, we’re going to look like this caricature of a woman. And that’s not the case at all. It’s more to get a smooth pallet on which to actually do the painting.
Delia: Exactly. Perfect.
Olivia: So some crossdresser makeup advice recommends beard cover and one of the most popular things, is tattoo concealer. Do you recommend a beard cover or is it just enough to shave, get super smooth skin use the primer then the foundation on top of it?
Delia: I think it really depends on the person’s individual beard and hair growth. I think if you’re going to be out a lot that day and you tend to get really fast, fast hair growth, like you know, the five o’clock shadow, then a beard cover is really good for kind of hiding that discoloration or that that shadow.
And I think it’s easy to use to just cover those imperfections where maybe the jaw line where you know you’re going to have a little stubble popping up it, it can be great to use just before applying foundation and, and give you that feeling of very feminine skin. So I would recommend a beard cover if the cross-dresser knows that she’s going to need it.
Mistress recommends foundation
Olivia: So speaking of foundation, personally, I love Mac cosmetics studio fix powder foundation. Although most people use cream or liquid, whether or not you’re using a powder foundation like Mac cosmetics studio fix, it still needs to be done with kind of stippling. So that’s dots or smudges all over your face. It looks weird when you put it on, but you smooth it with a stippling brush to smooth from one dot into the other rather than putting a blob of foundation and then dragging it over the skin.
Most advice that I’ve seen recommends using full coverage foundation.
You know what I was saying, that there’s a difference between that mask look that looks great in photos versus going about your business day or going outside during the day. It’s the day look versus going to clubs. What is your favorite foundation for yourself and then for the ladies?
Delia: Hmm. Well I think it can be one and the same. My favorite foundation for myself and for the ladies is by Bare Minerals. I love them too. And I really love the bare pro line. I like it because for me, and say for a cross dresser, it has really truly 24 hour coverage. I’ve done like putting it on in the morning and I’ll wash off all that makeup at night. It just doesn’t go anywhere. Even if I work out lightly, you know, go run around, do errands, walk the dog, something like that. It’s made of minerals, so it’s really good for the skin, it keeps your skin healthy and they have great tone matching. So I think it’s a simple healthy line that can be used by anyone.
Olivia: One of the things that I love about Bare Minerals is you can do it very, very light or you can go a little bit darker with it. That’s the same thing with the studio fix powder foundation. You can put it on very light or you can put on a layer, then another layer, then another layer. So you kind of layer the foundation on top of each other still without it looking all glommed up and mask like.
Delia: I think that’s always pretty when you look and just say, Oh, I have a little blemish here. I got a little extra sun on my cheeks and you just do a little swipe or take your stippling brush and just kind of go over it. Again, I love when foundation can do that and you can stack it on top of itself.
Contouring for male to female transformation
Olivia: There’s a fair amount of controversy over contouring. When you see somebody like Kim Kardashian’s makeup, you look at her with unmade up skin or someone like Jennifer Lopez or really any movie star or model. They all use contouring in order to kind of change the shape of the face. But for just everyday women, there’s some controversy about whether or not you want to use contouring.
What contouring is: you get something a couple shades darker and then you stipple it around the edges of your face, the sides of your nose. I personally like contouring because I like that more finished and polished and defined sort of look. But a bunch of people say do not play with contouring unless you really know what you’re doing or don’t use it all. What do you think?
Delia: What you just said I think is the main thing. Contouring basically works with a person’s individual face. So I understand why it’s done, why contouring is done and I have seen online, anyone can look at the contouring maps that different people post up where they use the lighter contours and where they put the darker bits in and how they blend it, but that is to their own face, to their own face shape to their own neck shape.
I personally am one who dislikes contouring because I think most people just don’t know how to contour correctly. So it ends up looking overdone unless you’re a drag queen on stage doing the contouring for a show. I personally like a much more natural look for crossdressers. So what I would recommend is instead of doing all the contouring, highlight all your important features, your pretty eyes, your soft lips, and maybe just do a little cheek contour, do less. For me, less contouring is more.
Olivia: That is such a great point. And as a photographer, here’s like the purpose of contouring, the darker shades deemphasize that particular area. Then if you put a lighter shade or white or a glimmer say underneath the eyebrow or right on the bridge of the nose or right above the cheekbone, you get those bursts of a little bit of lightness. And so the eye is drawn to that.
You are absolutely right. Just go for the eyes, go for the lips. I mean, let’s face it. That’s what you want the eye to focus on.
Sexy eyes: what you need in your crossdresser makeup kit
Olivia: Let’s talk about my favorite, let’s talk about sexy eyes.
Delia: I love sexy eyes, windows to the soul
Olivia: Lots of people have dark circles under their eyes. And this is for cis women, cross-dressers or sissies. It’s totally gender nonspecific. So if somebody has dark circles, do you use or recommend concealer for the dark circles?
Delia: If it’s just dark circles under the eyes? Absolutely, yes,1 million times yes.
Delia dishes on under eye concealer
I have a wonderful concealer; it’s a basic cover girl stick concealer. When I have just been running around, I haven’t slept well, and I look at myself in the morning if I’ve got some dark circles under my eyes I just grab that stick, brush a little concealer over them.
I have a brush for my concealer. It’s a little harder than my foundation brush and I just kind of feather out and soften the look. And then I add my makeup and I don’t have any dark circles. It’s wonderful.
But I will say this, if you have puffy eyes that are dark underneath the eyes, like bags under the eyes, don’t use a concealer on them because concealers tend to be lighter to lighten the skin. What you’ll end up doing is actually highlighting the fact that you have bags under your eyes.
What you can do instead is put a cool cloth, some cool cucumbers on your eyes. I have even seen people use things like preparation H hemorrhoid cream. Use just a little dab on the bags under the eyes and they go away. Then you can use your concealer.
Delia converted Olivia to concealer
Olivia: What a great point. I hadn’t even thought about the bags under the eyes, but you remember that very first fetish convention that we went to? We met the next morning for breakfast and I’m like, “Fuck, you look great! I didn’t get any goddamn sleep!” I knew you were in there playing with me and I was like what the hell!?
I was kind of mad. I was a little jealous and kind of mad. You whipped that little concealer tube out of your purse and said, “This is what I use!”
I never used under eye concealer until then except when I did makeup shoots or something, but just for normal day where I’d never used it until you whipped it out of your person and said, “Use it. This is my secret weapon.”
Delia: Happy to help. ~laughter~
Olivia: I got microblading on my eyebrows. Microblading is like really delicate tattooing, it’s like tattooing individual lines. So the arch of my eye is already set, but before I got the microblading done, it was really hard to learn. Where is the arch? Where do I want to put it, what style?
Eyebrows are a huge topic. Huge topic.
We talked to Yvonne in our interview with a cross-dresser. She asked me what I thought about arch patterns. Drag Queens cover up their natural eyebrows and draw it on. But that’s very stylized.
Talk to me about eyebrows. What do you do? What do you like? What do you recommend?
Delia: As I’ve said before, I love a very natural makeup look for most day to day things. So I don’t really like to change the shape or arch of the brow too much.
I like natural. I know people have to pluck their eyebrows and cis women do it. Cross-dressers do it.
I want everyone to pluck a little bit just to get rid of the stray hairs. Pluck the little hairs that give you the unibrow on the bridge of the nose.
I think for eyebrows, using a brow pencil can do a lot to give an optical illusion that shows a defined or or more arched brow. And I love a good brow brush because you can smooth out your brows. You can see any straggling little hairs that may curl up and you can just snip those like with a nail clipper or something.
As far as the arch patterns, again I go to a more natural look. I like kind of a straighter or softly curved, softly arched brow that looks very natural for everyday wear. For events, you can have fun kind of highlighting or plucking. I love using those to create a higher, more defined arch like for events or something like that.
Olivia: That’s a really good point. I was watching NXT wrestling. Okay. I’m not this huge wrestling fan, but occasionally I like to kind of tune into the beginning of stuff because I like to watch, like the storylines and the smack talk and that kind of stuff.
There was this woman who was on the set, a dark haired woman, I don’t know what her name is cause I don’t follow it that much, but she had on like these eyebrows that were drawn on that were obviously from a pattern. From a distance. It looked kind of interesting. But when the camera came in for a closeup, it looked awful. I mean it was way too extreme.
So I think your point is well taken. It depends on where you’re going to be going and less is probably more, especially if you’re going out.
Delia: I agree.
Sexy eyes and luscious lips
Olivia: So you’ve got all of the foundation done ladies. Let’s talk about your actual eyes and lips.
Some simple ideas for feminizing makeup is … wait, let’s also just pause for a second and acknowledge that there are huge variations in transgender expression.
Yvonne in the interview with a crossdresser, said she personally doesn’t like the labels and doesn’t want somebody else’s definition to put her in a box. So we’re going to use gender identity terms pretty much interchangeably and let you say who you are.
That said, as we talk about makeup for your eyes and stuff, you get to experiment with and define how intense you want to go and what your style is.
Just remember that there isn’t some end goal to this. It’s more the act of learning. I think when learning to apply makeup, that’s part of the key thing. You’re learning and you’re growing and you’re playing with the makeup. Part of it is the journey.and learning your crossdresser makeup.
Delia: I agree so much with that. When you and I were talking about it doing this crossdresser makeup podcast that was one of the things that we really talked about so much.
We wanted to have a wonderful conversation about things that we love and give advice and tips and I think we always offer our support. So if, if anyone has questions about makeup after this podcast, remember it’s important to talk to us to reach out to us because we really want to help you navigate the various terms, the various pieces of cross dressing and feminization. And I know that we want to help support everyone’s journey.
Olivia: We can even do makeup tutorials on Skype. We can watch you as you’re putting on your makeup. Email us!
Olivia: We are obviously Femdoms. We are Dominant Women. So a lot of people listening to this podcast like to be dominated sexually while dressed as a woman. Many men who cross-dress don’t identify as trans.
How you’re doing your eyes and your lips, some of it depends on what you want to achieve and are you playing a sexual game? Is it for sexual pleasure? What do you want to emphasize? That sort of thing. Or you might be a transsexual and sort of growing into your femininity. We don’t care. We’ll take you either way. We like you!
Delia: That’s very true. I mean, obviously we specialize in being Femdoms, but both of us are super sex positive and gender positive. So we want to only, and always bring out the best in you.
Olivia: A word of caution though, if you go to a professional image consultant, this may or may not be right for you. You might end up with a ton of clothes that you don’t feel comfortable wearing. There are insane prices for a feminine makeover.
An in-person consultant for your feminine make-over is certainly an option. Make sure that you find one that specializes in cross-dresser makeup, cross-dress styling, that sort of thing.
Crossdresser makeup and full feminization
Olivia: Sometimes I think you and I should really start a crossdresser makeup salon.
Delia: We would be great. We would be amazing with that. The power ball lottery comes on and everybody has that daydream about what they would do if they won. I seriously would create like a cross dresser village and we would have our makeover salon because we would be amazing and we would give just the best, most caring, most wonderful crossdresser makeup and styles.
I mean I love that stores like Bare Minerals and Sephora. They offer the free makeup tutorials from Sephora in person right there in the store. And I’ve talked to people and they can be either private like in a back room or they can be public say at the makeup counter right there in the store. And it depends on your comfort level, but it’s great because you buy some makeup that you really want and you can do this before or after you get the free makeup advice and learn how to use what you are thinking of buying or just bought. I love that that can happen.
Olivia: You mentioned Sephora. I also love the free makeup tutorials at Sephora.
One word of caution with Mac cosmetics, you can walk out of there with fabulous sable brushes and eye shadow and all of this for contouring and smokey eyes, all of that kind of stuff. You can easily drop five to $600 on your first Mac cosmetics excursion.
So go for the training and then get with your Mistress about what to buy from Mac cosmetics and how to kind of lower your, your makeup bill.
YouTube, by the way, also has some great videos. I still like to think of the girls working with the Mistress because we know you. We know what works, we know what’s best, don’t you?
Delia: I completely agree. That’s the way it should be. Get pretty with your Mistress.
Olivia: One fantastic resource is the wealth of instructional audios and sexy audios on our site GET GIRLY.
We are celebrating the 16th anniversary of that feminization audio site. Part of the celebration includes a sort of treasure hunt for all the words in a paragraph.
This is the phrase that pays. Make a note of this. You’re going to need it for the party. This is the phrase that pays. I love wearing makeup and hearing Mistress say pucker up sissy.
Again, the phrase that pays is: I love wearing makeup and hearing Mistress say pucker up sissy.
Come to the party and GET GIRLIE!
The party will be held live on cock radio and in our community kink chat room on February 22nd from eight to 10:00 PM Eastern. Ms. Harper will be the main hostess and a few others will be joining her live during the party, so we hope to see all of you there.
Crossdresser makeup essentials for sexy eyes
Olivia: What are some of your essentials for very sexy eyes?
Delia: Ooh, that is a great question. You know that I love to highlight my eyes and lips. So I’ll talk about eyes.
I have two things that I am absolutely never without. I love the Bare Minerals nonstop navy eyeliner. It doesn’t smudge like all day long. It doesn’t fade all day long. I mean, I look at myself in the mirror throughout the day and I always kind of check, you know, my eyeliner, how my eyes look, do I need to add a little extra note? It looks great.
I really love a natural look, but I’m not against some shimmer or some glimmer. So my go to is the urban decay naked palette eye shadows. They have three of them. And in my makeup bag I have one of the three, no matter what, they’re these pretty nudes, tans, and taupes. They’re just the naked colors. They’re soft and pretty. You can do darker or lighter and you can even add a little bit of shimmer. And I think they can make any skin tone, any eye color look just fabulous because they are so neutral. I love that.
Olivia: One of the great things about that neutral palette is you use the lightest color. Say if you have a pallet of three, you went the lightest color right in the corner of your eyelid closest to your nose. So put the light color there, put the medium color on the middle of the eyelid, out to the ends of the eyelid, and then put the darkest color in the crease of the eyelid and then put the lightest color back up under the arch of your eye.
Now this is super important. Whenever you’re doing anything with makeup and especially with your eyes blend, blend, blend, blend, blend, and then blend some more.
You don’t want to have a line on your eyes.
Oh and another thing. You talk about your eyeliner, not smudging. You want a smudged eyeliner if you’re going for that smokey, sexy look that, yes, it looks fabulous.
What you don’t want is if you’re going out and if you’re going clubbing and say you get a little bit hot because you’re dancing or you’re aroused, you don’t want your eyeliner to kind of melt.
Delia: That smudge run that looks like you’ve been crying or something. It just bleeds onto the skin of the under eye and it just looks so, so, so, so horrible.
I think it’s good to look for really good quality products. You might spend a little more money on a product, but if it’s great quality, it is so worth the extra pennies just in how you’re going to look and feel.
Sissy and drag queen makeup is more extreme
Olivia: Now, if you want a stylized Drag Queen look or sissification of a sissy, you actually might want your eyeliner to kind of run. That’s because sissies are more extreme. Maybe for cock sucking and your eyes tear up and your makeup runs.
If you want that and make sure it’s intentional rather by accident.
Delia: Very good point. Very good point.
Olivia: Speaking of sissies, false eyelashes, when and how to wear them.
Delia: I absolutely love false eyelashes if they are done right and there are so many kinds. Now I say look for quality false eyelashes.
I will tell you something that I absolutely love. I freak out a little bit if I have to put right glue right next to my eyes.
Recently I have found something amazing. Um, it’s magnetic lashes. So the part that sits on your eyelid is magnetic and it pairs with a specific eyeliner. So it’s a magnetic liner and you just brush it on your upper eye with the little and then you hold the lashes out and it’s automatically just like drawn to that liner and it pops on and you can blink and you can look around and you’ve got beautiful false eyelashes. And if you don’t want them, they just pull right off, like right off. So this is perfect. If you’re experimenting with them and you know someone comes to the door and you’ve got to get them off quick, it doesn’t take 20 minutes. Like with glue.
Olivia: I’m so glad that you mentioned the magnetic eyelashes because here’s the thing, I’ve never been able to make them work. Yvonne bought a pair and she was like, “Oh, this sucks. This does not work at all.” So I know for sure that we’re both going to be experimenting with the magnetic ones.
I’ve always liked big long, extreme stylized eye lashes. Sometimes I will do the false eyelashes or I will go and get the individual application of each one glued on and threaded into my natural eyelashes. That’s expensive. And what you said, if you have to yank off your lashes quickly, that won’t work and I can’t even do that during the winter when my primary exercise is swimming because I’m wearing swim goggles and stuff like that. So make sure that whatever you get fits your life and your lifestyle.
Lips! Soft, moisturized lips help you stay in touch with your femme side. Even when you are not dressed.
Soft, feminine lips
Here’s a comment from Yvonne. I told her to go get Burt’s bees and get the chapstick in a flavor like vanilla. So there’s no shimmer, there’s no color, but it tastes feminine so she could be in touch with their feminine side when she went to work.
Here’s what she said, I am loving this Burt’s Bees. My lips have not been this soft since I was caring for my mother in her last years and I was dressing and wearing lipstick every day. Whether it is the sheer vanilla flavor I wear to work or my lovely magenta I wear when I’m completely in female mode. It feels wonderful. Since discovering Burt’s Bees, I love that stuff.
Delia: I do too. And the flavors are nice, but there’s something that I love too. They are the shimmers that I really love. I don’t think they really shimmer, but I have the Burt’s Bees lip shimmers in the color of champagne and that’s basically nude. It just glosses up your lips a little bit. I also have it in guava and I wear it. It doesn’t even look like I’ve got lipstick, lip balm or really anything on it just gives like a definition to my lips. It’s hard to explain. It’s really good. It’s a good match to my lip color and I can just wear that all the time. It’s a really great product and I recommend Burt’s Bees to cross-dressers as well.
One thing that I want to give is a tip: use lip liner. I think lip liner is so important because it defines your lip and if you say have like a thin upper lip, you can actually draw with a lip liner just outside your natural lip and make your lip look fuller.
I have a trick after lining your lips, so there’s not such a stark line because I love a natural makeup look, take your lip liner and lightly fill in the lips with the liner and then put your lipstick, your shimmer, your gloss on top. What it does is it makes your lips look seamless, your lip color lasts longer because the lip liner acts as like a lip primer. So I love that.
Olivia: Oh, and I will add on to that.
Once you lined your lips, take your powder and just dot it on the lip liner just very, very lightly, and then go in and do the lip liner on your actual lips.
So is that further? You know you, you don’t want harsh lines. That’s the biggest thing with makeup.
Oh and everyone has to get Mac cosmetics, lip glass, it’s my favorite lip gloss. It is sticky, shiny. There is nothing discreet or natural about this, but for a stylized, Oh my God, that’s a pair of lips going on over there, that’s exactly what you want.
No matter what color you have on underneath it, we’ll make it pop like you wouldn’t believe.
But remember, ladies, your feminine style is way more than crossdresser makeup. It is about presenting your beautiful feminine look and personality. Your makeup should enhance your image and bring out your best. Don’t be afraid to experiment. God knows we do.
Delia: Oh, that’s very true. We experiment all the time and that’s why I think we’re great to support people.
Olivia: Whether as your Femdom or your Mistress, it’s fun to have a dominant woman feminizing you. I feel that feminization is important for any submissive girl.
Yvonne said, “I love taking instructions from you to make me feel more feminine and get me in touch with my femininity. I think it helps to keep the flow of my feminization going. I get less masculine interruptions. I love that.
Delia: I mean that was so well said because Yvonne knows that we know what we’re talking about. We help with that flow and we absolutely love more than anything to give support for feminization and support to each and every individual submissive who comes to us to share their kinks.
Olivia: Speaking of dominant women giving you orders, if you’re listening on Apple podcasts, we want you to go to The Weekly Hot Spot podcast, subscribe to the podcast, like it and then leave a review. Thank you.
And speaking of community support, this year we are celebrating the 16th anniversary of our site Get Girly. Eroic audios, tips about feminization, naughty sissy audios, and so much more.
Part of this celebration includes a treasure hunt for all the words in one paragraph. This is the phrase that pays. I love wearing makeup and hearing Mistress say pucker up sissy.
Delia: The party will be held live on Cock Radio and it will also be in our community kink chat room on February 22nd from eight to 10:00 PM Eastern time. Mistress Harper will be the main hostess and there will be a few others joining her live during the party. We hope to see you there.
Follow our blogs to hear just all the latest news and fun.
Delia: Beg for Mistress
Olivia: Experienced Mistress
Follow us on Twitter:
Send an email
Olivia: We would love to hear from you and we have some questions.
Mistress Questions about your crossdresser makeup
What are your favorite makeup tips? Do you have favorite brands in your crossdresser makeup kit? How has your feminine style changed over the years and how can Mistress support you, challenge you, and inspire you?
Delia: For now, thanks for joining us and listening to The Weekly Hot Spot.
Everyone have a great week and stay pretty!