Crossdressing for Beginners
Putting on a dress is the easy part. I can teach you the makeup, clothes, nails, posture and movement it takes to present like a proper lady.

Learning the Art of Feminine Presentation

Putting on a dress does not automatically mean you know how to present feminine. That is something beginners learn pretty quickly.

There is clothing but then there is makeup, wig, shoes, stockings, nails, jewelry, how you walk, how you sit. All these little details that bring the whole presentation together. Even something that looks simple like walking in heels or putting on false eyelashes takes practice.

Crossdressing does not discriminate against age, race, income, or walk of life. I have had people who have thought about it or fantasized about it for years before they finally decide OK, I want to explore this.

Some want to dress like a lady. Some want to look slutty. Some within a BDSM setting want to be a sissy. Everybody is different which is why when someone shows interest in crossdressing I ask a lot of questions first, so I can understand exactly what they are looking for.

Crossdressing for Beginners: Where Do You Start?

I start with what do you actually want?

Seems like a simple question but it isn’t always. Some people have had this fantasy for years and know exactly what they picture. Others know they want to crossdress but beyond that, they really have no idea.

What kind of clothing are you looking to wear? Day-to-day women’s clothing, something slutty, or sissy wear? Do you want a wig? Do you want makeup? Have you thought about having your nails done?

If you want stockings are we talking fishnets or nylons? Have you thought about breast forms, jewelry, and have you thought about a female name you wish to be called?

Then another big question. Are you looking to explore this in public or just in private?

All of those answers tell me something about what you are actually looking for.

When you are new I don’t think you need to run out and buy everything and think you have to know everything right away. First figure out what interests you. Then start learning how to put it all together.

Feminine Presentation Is More Than Clothing

Clothing is only part of crossdressing. It is not the complete presentation.

This is one of the things I think people underestimate when they’re new. You can put on a feminine outfit but then what about the wig? What about makeup, nails, jewelry, hosiery and shoes?

And then you have to stand up and walk. (Watching a woman walk in heels looks easy, but doing it is another thing.) All of it changes the presentation.

One thing I really enjoy is seeing the finished look. When someone has the full outfit on, makeup is done, wig is on and the high heels, and then they walk toward that full-length mirror.

That moment can be very powerful.

I have seen them look at themselves and feel beautiful, sexy and empowered. Now they’re not just looking at a dress or a wig or makeup separately. They are seeing the whole look together.

Choosing Your Crossdressing Clothes

One of the first conversations is what type of clothing are you actually looking to wear.

There is a big difference between somebody who wants a day-to-day feminine look and somebody who wants to look very slutty. Someone who wants sissy wear in a BDSM setting is looking for something different again.

Not everybody wants the same thing and I don’t treat them like they do.

I want to understand what look they are trying to create and then work from there. The person, their body, what they’re comfortable wearing and what they want to see when they look in the mirror all matters.

Shoes are another thing people don’t always think through!

Someone might love the idea of a very high heel but I have to consider their health and physical fitness level. That will help decide the height of the heel and style of shoe.

The fantasy may be a certain shoe. That doesn’t always mean it is the right shoe for you to actually walk around in.

Crossdressing Makeup for Beginners

Makeup is probably one of the harder practical skills for somebody new to crossdressing.

Usually we are dealing with skin that hasn’t had a lot of moisturizer on it, plus we may be trying to cover facial hair. These are things that somebody putting makeup on for the first time probably hasn’t thought much about.

People think sometimes you just slap a little makeup on your face and there you go. Not exactly.

There is a lot more that goes into it. Especially when you’re trying to create a complete look and not just play around with one thing in the bathroom mirror.

And you need patience. Nobody sits down with makeup for the first time and knows exactly what they’re doing. I didn’t learn overnight either. I’ve had years of practice.

You will get better each time you do it.

The Details Matter

People can get very focused on the dress and forget about all the other things. I don’t.

The wig changes the appearance. Some people envision themselves as blonde, but I use their skin tone to match the wig color. They might actually look better as a brunette but their fantasy is blonde, so I give them the opportunity to try on the blonde wig and then show them the difference and they are always impressed. Skin tone ladies….skin tone.

Then jewelry adds something. Stockings change the look and there is a difference between fishnets and nylons. Some people want breast forms as part of their presentation, others might not.

Then we have the nails. Press-on nails sound pretty easy until you’re sitting there trying to put them on and suddenly you’re getting frustrated.

Same thing with false eyelashes. I have seen people get very frustrated because it takes a little time and practice getting used to them. I remind them, I didn’t learn overnight either.

These things take practice. Each time you do it you will get better and better at it. Eventually something that was a huge production the first time isn’t such a big deal anymore.

Learning to Walk in Heels

Another misconception is thinking walking in high heels is easy. Put the heels on and just walk. Well, not always.

The height of the heel needs to make sense for the person. Their health and physical fitness level is going to play a part in what shoe I choose.

Then you have to actually learn to move while wearing them.

This is one reason walking is part of what I teach. I am not saying every woman walks one particular way because obviously they don’t. I am teaching the particular feminine presentation I want someone to learn during my Crossdressing Sessions.

You might look great standing still in front of the mirror. Now walk across the room. Often your first steps in heels are a male strut and you are disappointed in how it looks. Once I demonstrate how to walk which for you is a new way, you will realize it is difficult but not impossible.

That’s where you find out there is more to it.

Learning How to Sit

Sitting matters too. Again putting the outfit on is only part of this. If you want to learn the feminine presentation I teach then you need to learn what to do after you’re dressed. How you carry yourself changes the overall look.

That is why I work with somebody on walking and sitting instead of just putting makeup and clothing on them and saying OK we’re done.

Watch how a male sits as opposed to a female. Then try sitting in another type of posture with your ankles crossed or your legs together. You will find muscles you did not know you had!

I want you to actually learn something from me.

What I Mean by a "Proper Lady"

When I say I teach someone to be a proper lady, I mean more than handing them women’s clothes and putting a wig on their head.
It is the complete presentation and learning how to carry it.

When you’re brand new there is a lot going on all at once. You’re thinking about the makeup. The false eyelashes are giving you trouble. One of your press-on nails doesn’t want to cooperate. You’re trying to walk in heels, thinking about the wig and outfit and probably wondering if you’re doing everything wrong.

That is normal. With practice all those separate pieces start coming together.

That is part of being a proper lady in my world. It isn’t just what I put on you, it is learning what to do once it is on.

Confidence Comes With Practice

Something I have noticed is once people start exploring crossdressing many find a level of self-confidence that carries over into their day-to-day life.

Some will wear something as simple as satin panties under their work clothes. Nobody at work knows. Nobody has to know. But for that person it makes them feel very empowered and sexy.

For others it gives them a break from everyday stress. They get to let themselves go for a little while and escape from regular day-to-day life. Put on something different, become somebody different for a while and just enjoy it.

And most don’t want to do it all the time. I wish more people understood that. A man can enjoy dressing like a woman sometimes and that is OK. It doesn’t automatically mean he wants to live that way every minute of his life.

Crossdressing, Submission and BDSM

Crossdressing by itself does not mean somebody is submissive. But in my professional practice they can definitely overlap.

Some people specifically want to be guided by a Dominatrix. They aren’t just looking for women’s clothing or a makeup tutorial. They want me to ask the questions, teach them, correct things and guide the presentation. That changes the experience.

Again I need to know what they actually want. Are you wanting to be a lady? Are you wanting a slutty presentation? Are you looking for a sissy role as part of your BDSM interests?

I don’t assume.

Every person is different and this is why I take the time to ask many questions before we get started.

Crossdressing Does Not Tell You Everything About Someone

People make a lot of assumptions about crossdressers. Crossdressing does not discriminate against age, race, income or walk of life. I have seen enough people over the years to know there is not one type of person who is interested in it.

And it is way more common than most people think.

That is one of the first things I would tell somebody who feels ashamed or embarrassed. You aren’t the only person thinking about this. Far from it. There is nothing to be embarrassed or ashamed about.  It is OK to explore.

It also does not mean I can look at somebody who crossdresses and suddenly tell you everything about their sexuality, identity, marriage or personal life. People crossdress for different reasons.

Let them decide what it means to them.

Privacy Is Huge

Privacy is huge with crossdressing because the reality is most people still will not accept a man who dresses like a woman.

I don’t pretend that isn’t the case.

One of the biggest fears I hear is they don’t want to be found out. For somebody exploring privately that is one thing. Going out dressed in public is a very different decision.

If someone wants to take it into public then I discuss in great detail the pros and cons and the risks they may encounter. Their personal life can be affected and they need to think about that before doing it.

That isn’t me telling somebody they should hide. It is me being realistic with them.

You need to decide what level of privacy is right for your life.

What About Your Wife or Partner?

This is another area where reality isn’t always as easy as people would like.

If somebody tells their spouse or partner they enjoy crossdressing, the spouse or partner should listen.

But that’s not always the case. Many are not open to it. This is why somebody needs to consider their personal circumstances.

Crossdressing may be harmless but that doesn’t mean everybody around you is going to understand it or accept it.

I wish that was different, but I’m not going to tell somebody it is always going to go perfectly when they disclose it to a partner because sometimes it doesn’t.

On the other hand, many wives know their husbands crossdress, but only when they come to see me. These are wives who do not judge their husbands, but give them permission to come see me regularly so they can explore privately.

Common Beginner Crossdressing Mistakes

The biggest misconception is probably that being a lady is easy.
Put on high heels. Slap a little makeup on your face and there you go.

They learn pretty quickly there is a lot more that goes into a woman’s day-to-day preparation.

Makeup can be difficult. False eyelashes can make you want to throw them across the room. Press-on nails take practice. You might find the high heels you thought you wanted aren’t the shoes you can actually walk in.

There is a learning curve. That doesn’t mean you are bad at crossdressing. It means you’re new.

I always try to reassure you that I didn’t learn overnight either. I’ve had years of practice and each time you do these things you will get better.

Don’t expect yourself to know something you have never been taught.

What Happens During My Crossdressing Sessions?

I offer dedicated Crossdressing Sessions in Detroit for people who want guidance with makeup, nails, clothing, walking and sitting instead of trying to figure all of this out yourself.

And again, I start with questions.

What kind of clothing do you want? Slutty wear, day-to-day wear or sissy wear? Do you want makeup? A wig? Nails? Stockings? Jewelry? Breast forms? Have you thought about a female name you want me to call you? And are you wanting this just in private or are you considering going into public?

From there we can work on the practical side. Makeup, fake nails, choosing an outfit that accents their individual figure, walking, sitting and putting together the overall presentation.

Not everybody coming to me needs the same thing.

Somebody who has fantasized about crossdressing for 20 years but has never actually done it may need a very different lesson from somebody who has been dressing privately and just wants help getting better at it.

That’s why I don’t believe in one cookie cutter approach.

You Don't Have to Figure It Out Alone

If you’re going to take your first step into the crossdresser world, you don’t have to do everything by yourself.

Go to a crossdressing store. There is usually staff there who understand what you’re looking for and can help you. 

Janet’s Closet is one of the largest cross dressing stores in the United States. Even if you do not live in Michigan, they can help over the phone with clothing, shoes, make up, breast forms. In addition they have a forum you can join that will help you realize you are not alone.

If the submissive or BDSM side of crossdressing is part of what interests you, meet with a professional Dominatrix who truly understands it and can help guide you.

Research who you’re meeting with. Ask questions. Find somebody who actually understands what you are trying to explore.

And have some patience with yourself. Makeup, clothing, nails, shoes, walking, sitting and putting the whole look together are skills. You aren’t supposed to magically know how to do all of it because you decided today you want to crossdress.

For me one of the best parts is still that finished moment. Full makeup. Outfit. Wig. High heels. Then you walk toward that full-length mirror and see yourself. The excitement, confidence and the way you suddenly feel beautiful and sexy.

That is the part you can’t really understand from just looking at clothes online. Sometimes you need to actually see yourself.

If you want to learn how to put together the complete presentation and not just put on the clothes, my Crossdressing Sessions are designed to teach you.

Ready to explore?

Your Mistress,

Read More Posts

Newsletter

Join my mailing list

Join my mailing list for a special bonus time offer to serve your Domina. Good subs are rewarded. Sign up now!