Crossdressing Make-Up

Crossdressing Make-up

Crossdressing Make-up

Hi Charlotte

I am just starting out on the journey into femininity, would love to be able to wear make-up without anybody noticing that I have it on. Unfortunately I live in Scotland, would love to be able to come to your crossdressing make-up lessons. What would you recommend that I start with: maybe a clear lipstick, and/or clear nail polish?

Thank you in kindness. Alex


My dear Alex,

This is an important question that I know others will be asking as they make their way on their journeys to femininity. Crossdressing make-up can be such a puzzle.

Invisible make-up? Don’t believe it. Many women like me will nose out your secret with a sidelong glance of their eagle eyes, if you will forgive my mixed metaphor. Even the most ‘natural’ crossdressing make-up will leave tell-tale indications. A clear nail polish is designed to reflect light and those reflections will be seen. And neutral or clear lipstick will leave a feminine and, in my view, oh-so-desirable sheen upon your lips. Yes, it does make you feel fabulous. But, don’t worry too much about men: most won’t even notice any light application. Their minds and egos are typically elsewhere.

So let’s get right to the main point behind your question on crossdressing make-up. You want to move further ahead on your journey. Firstly, you are absolutely right to want to do so. In fact, you will find it incredibly difficult not to do so. Feeling feminine is not something that is an add-on in your life: it is a vital part of the person you really are. So there is no point in denial or self-deception. But I do understand the need for discretion.

Secondly, your intuition that you will need guidance and advice, and not just about crossdressing make-up, is spot-on too. But let’s put this in the context of the ‘bigger picture’ – namely your need to feel more feminine, and accepting that you wish to take this step by gentle step starting with the right approach to crossdressing make-up, building your self-confidence.

So here are my three rules for feeling feminine without revealing too much to others.

  1. Wear panties – the silkier the better – every day or whenever you can, if this is possible for you.
  2. When you go to the loo, if you are not doing so already, sit down as often as you can. You are a girl after all.
  3. Listen to one of JJ’s feminizing MP3s; and don’t be afraid of the tag ‘hypnosis’: JJ will help you develop your feminine self-image by allowing your conscious mind to interact more readily with the subconscious, from where all your feminine feelings are arising. Just listening to her soothing and ultra-feminine voice several times each week will allow you to access your feminine side much more easily.

So here is my Charlotte ‘basic’ crossdressing make-up lesson just for you.

Applying crossdressing make-up with guidance is trial and (mostly) error. It needs lots of practice. So you are quite right to start crossdressing make-up with modest ambitions; and to seek assistance. Ideally a trip to JJ will help to get you started, and, should you wish, this will have the added and wonderful bonus of allowing you to see yourself fully dressed and in professionally applied crossdressing make-up. That, as I hope you soon discover for yourself, is such a magical moment. But what if you can’t get to her easily? A bad makeover with crossdressing make-up may be worse than none at all, and sadly there are some real ‘cowgirls’ out there. And there are some who just cannot cope with the idea of a man wearing crossdressing make-up without creating variations on some overblown drag queen.

Some lipsticks and lip glosses can be close to invisible. Try neutral or brown shades. You need to see what’s available in crossdressing make-up for yourself. That moment when you first walk up to the makeup counter in the department store is pretty nerve-wracking, But most make-up girls are very sympathetic. They don’t even raise an expertly plucked eyebrow.

If you are at all nervous about using a ‘transparent’ base and top coat crossdressing make-up nail varnish because of its gloss (which it is meant to have), you can get hold of matte top coats. But you may prefer to use just a double base coat (which can have a slightly less glossy appearance) when you don’t want your crossdressing make-up to be too conspicuous. But you could decide instead to paint your toes instead of your finger nails. And depending on your home circumstances those crossdressing make-up nails could be as bright and bold or as discrete as you like.

Let JJ know how you get on with your crossdressing make-up. And remember: the girl within you will never be content until she is allowed to express herself.

Charlotte xx