Sissies & Makeup

For new or isolated sissies, it can be a challenge to learn how to put makeup on. Happily, I have a couple of tried and true ideas for you.

Online Tutorials

All over the Internet, but especially on YouTube, you can find tutorials about makeup placement. What is wonderful is you can find the “classes” given by transwomen, crossdressers, sissies, ciswomen… young, old and in-between. They teach everything from how to choose an eyeshadow color or the color of your foundation, to the minute details of putting on single eyelashes and the nuances between lip colors and lip liners.

If you do not find the person’s instructions clear, try someone else. It is not you, but the teacher… and thank goodness, there are endless teachers on YouTube!

Keep practicing in the privacy of your own home in your own mirror. It is exactly what we cisgirls did growing up.

And I promise garish mistakes will happen! Just laugh it off, use the makeup remover and start again. Do not judge yourself and your skills (or lack thereof). It can take years to learn to do an eye like the one above. Perfectly normal.

Makeup Counters

You might have read or heard of others going to major department stores or boutique makeup stores to learn how to wear the item of makeup you’re wanting to use. If you live in a small town, you might want to go to a larger city before being seen at the counter talking to the salesperson. But, if you are brave or are in a big city, going to either of those locations can be great for your education.

The salesperson doing your makeover will offer a slew of different colors and brands. In order to keep things straight (so to speak), take a picture of the item next to where it goes on you. For example: Take a picture of your blushed cheek with the label of blush next to your face… make sure you can see the brand and the color.

If the person is going too fast, ask them to please slow down. They should not have one iota of impatience or disdain for you. If you feel they are uncomfortable, ask to speak to the Manager. Transfolks are a significant portion of their customer base and deserve to be treated respectfully.


I learned a new word writing this! Maquillage – Mock-kee-yahzhe (like the sound in beige). It means “to put on makeup.”

There are places around the country where girls can go to get complete makeovers, often including hair, “breasts,” clothes and shoes. I talk to many of you who go to Las Vegas, Los Angeles, New York City or Atlanta for a day of dress up. Please remember to get pictures taken! Many salons offer professional photos, but if you do not want that, at least get a photo of yourself on your phone.

When looking for places for complete makeovers, Google variations of trans makeovers <city you are looking at>, transwoman makeover <city you want>, transgender makeover <city you want> and you should come up with some results. If, however, you are not having any luck, EMAIL ME: and I will help hone your search for you.

But even after that, learning how to be a lady is work. Remembering to sit cross-legged, gauging how much hairspray is too much, perfecting the art of painting the nails on your dominant hand, discovering (the hard way) what dress shapes fit best — gender-born women have their whole lives to develop these skills, their formative years filled with slumber party makeovers, glossy magazines, the unspoken cues from older colleagues about how to dress for the workplace.”

Because cisgirls do have these privileges behind us, I need you to promise not to judge yourself harshly. Be gentle with yourself if walking in heels is clumsy, even for years. Do not fret that you will never figure out how to put mascara on without poking yourself in the eyeball; you will… I promise. We ALL poked ourselves in the eye… hundreds of times.

Take Your Time

I know you want everything done now. You want to be perfect at everything now. If you are desiring to pass, you want to now. If passing isn’t remotely a goal (and it does not have to be at all!), but you have <fill in the blank> goal, you want it fulfilled now.

There is no race. No one is standing behind you tapping their foot with impatience.

Take your time.

Really, be very kind to your little girl. Let her play in “paints” (makeup) and make messes. It is how she/we learn.

Most of all, have fun!

Enjoy the process of learning. Put on your favorite music, have your favorite beverage sitting next to you (with a straw!!! Girls with lipstick sip through straws!), spread your “toys” on the bathroom counter… and enjoy your time with yourself.