Time, Money, and Patience

If I have a philosophy, it’s “crossdressing takes time, money, and patience”.


This side of us takes time because we learn over time.  We get better at makeup the more often we put makeup on.  None of us are born with a steady hand and are able to do a perfect cat-eye every time we wear eyeliner.  Time is also essential when it comes to embracing this side of us.  I fully believe we are born this way, even if this side of us doesn’t “wake up” until later in life.  I was always this way but when I was very young and I saw the mannequins at JC Penney wearing beautiful lingerie… well, something just clicked.  Like a butterfly pushing its way out of a cocoon.  It took time to acknowledge this side of me, to accept it wasn’t a phase, and to embrace who I was.  Each stage took time, it took a long time to get to where I am today.


Crossdressing or presenting en femme isn’t cheap, at least it isn’t for me.  Sure, I can put panties or a nightgown on and I am crossdressing.  It’s about as inexpensive as crossdressing gets.  But being en femme is another story altogether.  Before I even get dressed or put on makeup, I am wearing my breast forms, thigh pads, and corset.  All of these things give me the figure I want when I am en femme and these things are not cheap.  For me, they’re worth the cost as I look at them as an investment and I see the return on my investment every time I am dressed up.  It sounds silly but when I see a curvy figure in my shadow I get a little thrill.  Clothes aren’t cheap, makeup isn’t cheap.  I had a makeup lesson a few years ago which wasn’t free but again, it was an investment.  Photo shoots, which I acknowledge are not something every t-girl does, take a lot of work and money from booking the studio, getting outfits, paying my photographer, and a professional makeover.  We learn a lot when we build our wardrobe and buy makeup.  If we don’t know how to find our measurements we likely will waste a lot of money on clothes that don’t fit.  You (for the most part) get what you pay for when it comes to makeup.  Sure, foundation from Walgreens might be 5-6 dollars, but that won’t work when it comes to what I need foundation to do.  I need my foundation to mix well with color correcting and to cover my facial hair and to act as a good base for more foundation for contouring.  The foundation I need runs about $40.  


And finally, patience.  This is the hardest part for me.  It was very disheartening to see how I looked the first time I did my own makeup.  The first time I wore a wig.  I expected to be totally transformed but I looked like the boy me in bad makeup and a cheap wig.  I mean, that’s not unfair to say.  The wig was cheap (there’s the money part again), and my makeup was rushed (oh, and here’s the time thing again).  I expected to look AMAZING the first time I did my own makeup but I was… well, I didn’t look amazing.  It was a little discouraging and I COULD have given up on all of this (I mean, not really, I can’t quit being trans no more than I can quit being tall or being right-handed) but I tried again the next weekend after my wife showed me a little more technique when it came to my foundation and reading more about color correcting.  I looked a little better, at at least, a little less terrible.  Patience was also key when it came to wearing a proper corset.  Corsets require seasoning (essentially breaking them in) and the first time I wore my current corset I thought I would DIE after a half hour.  It was painful and I couldn’t see how on earth I could get used to it.  But I kept at it followed the instructions and took my training seriously.  These days I can wear my corset for ten hours without even noticing it.  Thank god I invested my time and was patient with it.


I got to thinking about all of this a couple weeks ago when I was getting dressed.  In the early days my wife and I would have a girls night on Saturdays and I would get dolled up.  It took about thirty minutes to get dressed and do my makeup.  These days it takes that same amount of time to just put on my corset, stockings, pads, and forms.  Being en femme takes more prep work and planning than it used to.  For example, for the longest time I wore nylons or tights and I could wear a short dress or skirt without thinking about it.  These days I prefer stockings held up by garters attached to my corset.  A short skirt can show my garters and stocking tops and I don’t want to do that.  I mean, it’s kind of sexy to do that (if that’s the effect I am going for) but it’s not appropriate for a day at the mall.  So my outfit is planned around my corset, in a way but usually my outfits are built around the heels I am wearing that day, and my heels are planned on what I am doing.  If there’s a lot of walking or standing I’ll wear certain heels compared to my six inch platform stilettos.  Once I have my heels chosen then my outfit comes next.  My makeup is usually done to watch my outfit, not only in terms of colors and shades, but also in terms of, well, intensity and drama.  If I am wearing a bright flowery dress than my makeup is more colorful and cute.  Leather or a little black dress?  Vamp me up.


I have come a long way, even in the last five years, and it’s all due to these three things.  I get asked a lot about how does one crossdress and yes, I can be bitchy and tell them to wear panties or lipstick and ta-da, you’re crossdressing.  But that’s not helpful.  Crossdressing requires a wardrobe of course, no matter how big or small it is.  I mean, you can’t crossdress without SOMETHING, but once you start thinking about this other than about clothes, you need to know that this is a side of yourself that you need to invest your time in, spend your money on, and be kind to yourself while you are being patient.

Love, Hannah

2 thoughts on “Time, Money, and Patience

  1. There’s no doubt that cross dressing gets pricier the more we indulge in our feminine side. I wouldn’t say the cost of things has never been a concern but it has always been easier to justify buying yet another bra or a skirt and blouse than trying to decide whether I really need something new for my male side. When it comes to male clothing I look for things on sale but not so for my girly things, if it catches my eye I almost have to have it and tend to ignore the price and tell myself it’s a known fact women pay more more for fashion than men so there is no guilt in forking over more than I feel something is worth.

    And lets face it, how many bras do we really need? My closet and lingerie drawers have become collections of colourful eye candy and as as supportive as my wife is there is a limit I am careful not to cross. It would be simpler if we were the same size and could share things but we also have different fashion tastes so closet space is another issue I must be mindful of. Still it’s a wonderful dilemma to have.

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  2. I’ve been through a couple of purges and the one thing that stings (besides the forms foundations, wigs, and cute clothes donated to goodwill) has been the expense of replacing all that I gave away. I tell myself I will never again give up what I’ve worked so long to acquire – and that applies to the skills as well as the physical artifacts.

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