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The Importance of Setting Goals as a Crossdresser

transgender girl in a blouse and skirtIf there's one message that I want conveyed to my readers it's that in order to become a passable male to female crossdresser in public, you need to set reasonable yet specific goals and then fulfill them. For example, the very first time I ventured outside wearing a dress and pantyhose was at the age of 14. It was during summer vacation from school, and I stayed up until 2:30 AM before finally sneaking out of the back door of the house. I only wandered around our back yard and then walked to the side of the house and peeked into the front yard with my heart pounding, but still...I was outside wearing a dress and nylons, and for the first time ever I felt that sensation of having a gentle breeze blow against my legs while wearing pantyhose. It's a sensation that I'll never forget, and it's something that encouraged me to push myself even further.

Now, that's not exactly an adventure that will make the front page of my website, but the key is that I fulfilled one of my early goals in life, which was to wear a dress and pantyhose outside. Granted, it happened at 2:30 AM and no one was around, but I was as scared as I've ever been. I smile at that memory now and realize I had very little to worry about then, but the point is that we all have fears in regards to our crossdressing, and the key is to find ways to overcome those fears because that's how we become passable. And in order to overcome those fears, I'm a firm believer in setting what I'll refer to as crossdressing goals. Setting and achieving goals is what pushes us to become better no matter the subject or the field, and this applies to cross dressing as much as anything else.

So what was my next goal after wearing a dress and nylons outside during the summer? It was to wear pantyhose outside earlier in the day when people were still awake. I finally accomplished this goal during high school when I figured out a system of walking the dog around 9:30 PM up and down our street. I would dress in a t-shirt, pantyhose, and a half slip, and then I would pull on a pair of track pants over my slip and pantyhose. Next came socks to cover my ankles, and no one in my family could tell that I was wearing anything sexy a crossdresser with her slip showing beneath her skirtbeneath my track pants. I would put the leash on the dog, slip into my Reebok tennis shoes, and then announce that I was taking the dog for a walk. As soon as I was outside, I would slip behind a huge pine tree in our front yard and remove my track pants and socks leaving me wearing a long, lacey half-slip in white over suntan pantyhose with white Reebok tennis shoes.

My street was not a busy street at all since I grew up in a typical suburb, and the neighborhood was mature enough that we had plenty of tall trees and bushes where I could hide if needed. We also only had two street lamps between my house and the corner, which was about 400 meters away, and so I would carefully walk the dog down to the corner with my legs clad in nylons and my feet enjoying the slippery feel inside of my Reeboks. If a car did happen to drive by, I could easily hide or stand behind a big bush so my lower half was out of view from the passing car. I guess there was some risk in doing this, and my heart pounded every time, but in my mind it spelled improvement, and so now it was time to think of that next step that was a little bit braver and required taking a little more risk.

I won't bore you with my entire progression from that terrified 14 year-old up until this forty-something who finally achieved her goal of shopping at Victoria's Secret and purchasing a bra from a velvet hanger, but I will list certain phases that I believe one can go through in order to become passable in public as a male to female crossdresser. I would also encourage you to identify your current phase and then plan out in your mind how you can make it to the next step.

Underdress in public with and without socks
Underdressing is defined as wearing women's underwear or lingerie beneath men's clothing, and it's a critical step in my opinion in terms of getting used to being in public wearing a bra, panties, and pantyhose even if you look like a guy on the outside. I vividly remember my first year in college when I went to the supermarket for the first time underdressed. I was wearing normal jeans, boat shoes, and then No Nonsense pantyhose underneath because it's hard to see them even when wearing a skirt. There was maybe an inch of skin showing between my shoe and jeans; yet, I was as terrified as I've ever been avoiding people in the aisles and standing at weird angles in the checkout line. I laugh at that now because no one would have been looking at my feet anyway and just a miniscule strip of nylon covered flesh could have been seen, but at the time, it was a huge step for me. After getting used to showing an inch of nylon around the ankle, that soon expanded to two inches with shorter jeans and then four inches with my jeans rolled up and then six inches if I sat down at the library with the cuff of my jeans riding up. The advantage of underdressing in public is that it helps you to realize that nobody is watching you as closely as you think they are.


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