If you imagine cross-dressing as a swimming pool, there really are two approaches to soak in the experience: Dive in headfirst, drench yourself, and the heck with the consequences, or dip a toe, dangle a leg, splash lightly, and ease your way in. Both methods can serve to achieve your ultimate goal if that is to present as the opposite of your traditional gender with comfort and acceptance. And yes, there are 50 shades of in-between to experience that perfect day of thrilling experience. Your own personality will help dictate the path you choose, and both are a means to your end game. However, any path needs a map and a plan. Remember the old adage: The lack of a plan is a plan to fail.
I was a secret MtF crossdresser from the time I discovered mama’s heels at six-years-old. My mom was a clothes horse. Mom in heels and hose, makeup, and hair was a very happy person, very pretty, and popular. I started with the high heels. They were the easiest to access and the least complicated, and yes, they made me really happy!
Growing up in the ’60s and ’70s was not conducive to being a CD. I was caught more than once. It was traumatic and made to be humiliating. My inner-girl never gave up, but over the years I lost two marriages over it and had no allies. I felt very alone, and in the short story, I never shared my angst, causing me to purge my gear often only to rebuild it back up. I tried to suppress it, and I was afraid of even mentioning it.
When I turned 40, I met an amazing woman who quickly discerned there was another person lurking inside me. She was the one who coaxed Marla into the light, teaching her makeup skills, helping her with clothing choices, and slowly building up her confidence. There were some Halloweens that provided a safe backdrop for Marla to burst out of her prison, painted and bejeweled, to jump into the deep end of the pool. Sadly, it took more years and many steps to take her from a costumed shell to a genuine everyday presence. Marla and I now co-exist every day, traveling together, and choosing whether to look like a guy, girl, or usually somewhere in between.
Some of the preparation occurred over years in forming who I am today. Getting healthy meant eating better food, losing weight, and stopping smoking. The result? I have more energy, better skin, have gone from 360 pounds to a size 18 thus far. Marla insists that we never stop improving, and stem the tide in hopes of reversing the process of looking old. I reward her with more of the girly adornments she likes as she successfully drives us into a better physique. Anything she buys goes on her credit card. (I set up a user account in her name on one of my credit cards).
I began to under-dress years back. I own but one pair of men’s underwear used rarely. Days that require jackets routinely mean it is a bra day (yay!) and a long-legged high-waisted, shaping garment that hugs me tight but comfortably, and holds up my thigh highs day.
Over time, all the jeans and casual slacks are in women’s sizes now. I do not own a male pair. Tops, sweatshirts, jackets are all women’s wear, and the only compromise to men’s wear I have to make for a normal day is shoes. (I wear a size 15 women’s shoe, and the choices are limited).
My hair and nails have been a gradual thing as well. My nails are done, most of the time on that border in their shape of male or female, and modestly painted. I have let my hair grow to shoulder length, I color it tastefully, and have learned how to curl and comb to emphasize how much Marla wants to be seen.
I started doing daily makeup a little at a time. It began with a touch of gloss and a little concealer, maybe a smidgen of a liner. I built my confidence to daily false lashes and doubtless color, foundations, and concealers, and I now adjust the intensity as my mood dictates. My ears are pierced. There is always a bracelet or two of either gender paired with a necklace that changes style/gender by my present mood.
In short, I found it easier to gain my inner-joy by adding one aspect at a time, seeing for myself that no one was going to throw me in weirdo prison, and in taking the next step when comfortable. I gained daily skills with makeup, daily comfort in crowds, and overall, when I do choose to do the full out Marla in all her finery, I can without anxiety and with confidence. For me, it is the way to quietly immerse myself without the big splash.
I have found that without the anxiety, I can objectively perceive from reactions around me what works, and what might not or doesn’t. The secret I have found is staying tasteful in my choices and keeping mindful of where I go. Most people are too busy in their own affairs to worry about you. Most men don’t appear to notice. Women might, but rarely have I seen negativity. More often than not I see approval in their gaze and even get compliments, and on occasion even constructive advice.
Doing a little at a time will build confidence. Step-by-step, get comfortable in your own skin and you will be beautiful. There is a thrill to me as a 6 foot tall, 360-pound bearded 65-year-old couch-potato morphed into a much happier (and attractive) me. Enjoy your journey and find your joy. My only regret is not following my desires while younger. My daily joy is that I finally did. You don’t have to be perfect, but you can strive to be perfectly happy. I certainly don’t claim to be perfect, but I am getting better.
Whatever happens, be the best you, be the you that you want to be, and in all sincerity, you must love yourself before you can truly love another.