I would like to crossdress, where do I start?
Like anything, you start small and you start gradually. Learn by doing. Don’t cannonball into this (or anything) and max out your credit card only to learn that this (or anything) isn’t as much fun as you thought it would be.
You also need to think about what crossdressing means to you. Does it mean head to toe femme presentation? Does it mean wearing a nightgown to bed? Panties under your boy clothes?
If you want to go head to toe, then this might be a good place to start. But again, ease yourself into this. Don’t go out and drop $1300 on a wig and hundreds of dollars on makeup and clothes. If you aim for the stars on your first attempt, so to speak, you will not get there. No one paints the Mona Lisa the first time they pick up a brush.
If your expectations are too high (usually by aiming too high), then you may feel discouraged and disheartened when your mirror doesn’t reflect the gorgeous girl you want to be.
Practice makes progress. Your first time doing makeup will likely not be what you hoped. There’s a reason why many supermodels employ professional makeup artists and there’s a reason why a makeup artist studied cosmetology for years.
If crossdressing means wearing clothes that are usually thought of as “girl clothes”, then perhaps start with the item that fascinates you the most. Some of us are in love with panties or nail polish or gloves or skirts or heels. For almost all of us, there is SOMETHING that awoken this aspect of ourselves. That SOMETHING for me was lingerie. So, I started with that.
However you start your journey, keep two things in mind:
Crossdressing takes time, money, and patience.
Be kind to yourself.
Love, Hannah
Have a question for me? Oh yes you do. Ask me here!
Hannah McKnight 
I can’t imagine starting from a place where crossdressing is something someone would “like to try”. I never chose to be a crossdresser, it was a desire that arose within me which I couldn’t control. It’s caused me to question my sexuality and my identity. It’s caused me confusion and feelings of shame and embarrassment. I’ve tried to resist it. I’ve tried to not want to do it, but ultimately I could never stop the urge to dress up in girl’s clothes. Like Hannah, I began with lingerie. Then I gradually experimented with other clothes and then makeup. Taking small steps is great advice. I’d also advise trying a professional crossdressing makeover. This will help you to appreciate your full potential and be something to aim for and learn when you try transforming yourself.
Good luck
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