How to apply lipstick as a cross dresser

Last week I went to the big-market. I thought I looked cool, chic, feminine and trés sexy. In fact, I looked like a dog’s dinner. People laughed at me and called me ‘Miss Piggy’. I cried all that day.

My friend Oscar to the rescue. “Learning the art of dressing as a woman,” he said, “can make life much easier for a cross-dresser”

Let’s start with lipstick.

“Lipstick can transform your life,” says Oscar. “Without lipstick you may as well throw the rest of your make-up away.”

There’s one golden rule when it comes to applying lipstick – whether you apply it painstakingly with a brush or splodge it on straight from the bullet – practice makes perfect! Practice, practice, practice. There’s no substitute. There’s no need to go through lots of procedures –apply face powder – blotting – apply colour – blotting – not until you get really good at all this. Then you can develop your own techniques.




  1. Hydrate your lips. Pucker and blow them to get the blood flowing. Then apply the teeniest amount of something like Vaseline, (helps fill in the cracks as well as providing a smooth base). Spread it THINLY.
  2. Apply the lipstick straight from the tube. OK it’s a little wonky at first but after practice you can get really good at this.
  3. Use a lip-liner of the same (or similar) colour to straighten those wonky lines. (Oscar uses a home-made brush for this exercise – a small paint brush cut near the base at a 45-degree angle – makes the brush stiff and easier to negotiate the corners and cupid’s bow.)


Find a lipstick that is suitable for you – one that lasts on your lips all day – and practice. Take your time – find somewhere to apply it. Nothing looks worse than seeing someone smear an unsightly blob, straight from the tube, when they think no-one is looking,

Tip – from the voice of recent experience – if you want to wear eye catching (red) glossy lipstick make sure the rest of your make-up is light – otherwise you’ll end up like Miss Piggy.




If you have dark skin matte lipstick can be so much more appealing. Oscar likes his lips to look dark and vampy – so he prefers matte to gloss.

Same procedure as above but you need to apply translucent powder to your glossy lips and blot on layers of powder and colour (often using a tissue if the lips feel too heavy) until you reach the desired effect.


Remember – practice, practice, practice!  Practice eating without painting your teeth red. Practice speaking without licking your licks. Practice kissing grand-ma without leaving the mark of Jezebel. Try experimenting with different colours – find out what suits you.

Oscar says he’s not fond of red. Red means ‘stop!’


Please send me any lipstick tips or comments I can share.


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