The First Ten Yards: Starting Your Journey

crossdressing decisions

The First Ten Yards

In the past, deciding to do the “first ten yards” could take me up to an hour.

And sometimes, I’d simply have to accept that I just could not do it. Sadly, I’d have to give up and either close my front door or simply start my car engine and head back from whence I came.

Can you guess what I am talking about?

Well, if you reflect on your own crossdressing experiences, your own concerns, and your own innermost doubts, then I'm pretty sure you know what I mean!

Decisions, Decisions

In fact, almost every T girl has been through the same sort of dilemma of indecision sometime during her journey towards womanhood: Do I or don’t I? Shall I or shan’t I?

"Phew,” you think, gently dabbing your forehead with a paper tissue, as sweat trickles down your neck, your hands all clammy and stomach churning, “What shall I do?”

“Now or in a few minutes? In a few more minutes or maybe I’ll wait ten… or fifteen more. Is there anyone around? Can anyone see me? Oh, is that someone coming? Hm, I’d better not.”

“Is my make up okay? Is my wig looking good? My dress nice and my outfit smart enough?”

Time to Own Up

Hands up if you have had similar thoughts while crossdressed in one of your smartest En Femme outfits. You surreptitiously peek out from behind the curtains of your living room, looking up and down your driveway, checking out both ways along your road.

Own up if you have had similar thoughts while sitting crossdressed in your car in a quiet location—maybe a supermarket or department store parking lot, or maybe the vastness of the parking areas of an empty sports stadium.

You sit debating, contemplating; thinking and thinking again; considering, agonising; wondering, trying to find some certainty to make that decision; trying to find something within you to dispel all of your fears and concerns, and propel you forwards, upwards and onwards.

You need something to propel you forward to take that first ten yards. It’s the first ten yards of the rest of your life.

Can I Really Do It?

Out you go into the all-embracing darkness of the night (it’s almost certainly likely to be the night as few, if any, crossdressers I know take their first steps out en femme in broad daylight—certainly not without some extenuating reason to do so).

So you’ve looked out of your living room window nearly one hundred times. Or you’ve sat in your car for nearly an hour watching a few passers-by come and go, watching the headlights of cars pull into and out of the parking lot. Nervously, you observe anything that moves.

"Can I do this? Can I really go out? I so want to, but yet I don't want to. To be honest I have no choice. I am going to do it. It’s just a question of when."

Doubts resurfacing: "If not tonight, then for sure next time, next week."

Doubts being dispelled: "Right! Right, let’s go for it!" The front door of your house or car door is partially open. "I’m going to do it. I am. Nobody will recognize me…"

Mental contortions. Psychiatric torment.

"But… but…"

I’m Out and Free!

But it’s too late now—and you are out of your house or your car. All that psyching yourself up seems to have paid off.

The exhilaration; the wonder; the beauty of the feelings; the incredible indescribable feeling of being out in the open air, in a public place, crossdressed.

The wind whispers around your legs, flutters your En Femme skirt. It tickles your nylon clad legs and brushes your cheeks, making a wisp of your hair come free. The air comforts you, gives you strength. It’s more exhilaration.

Don’t forget your demeanor and don't forget to walk like a “lady”. Control your shaking limbs, step carefully on your En Femme high heels—oh, and don’t over exaggerate the wiggle!

Try and keep your emotions in check; try and control the amazing sensations which dance around your torso—making you feel like you’re walking on air. What a buzz, what a feeling of ecstasy…

"I’ve done it, I’ve done it! I'm out and about dressed like a woman."

Worth It?

All that fear, all the trepidation has melted away and I’m out. I’m free! I’ve walked the first ten yards!

For those T girls who have achieved this milestone, heartiest congratulations. For those who aspire to do so, it’s just a question of time. And it’s well worth the wait!


  • Bob

    I'm totally new at this phase as it was
    Unfortunately not available when I was younger. So now at my older age I'm starting all over. It is so exciting all the new choices out there. I ordered a few items yesterday and look forward to building my wardrobe. Thank you!

  • Patricia Kay

    This article brings back so many memories and feelings that I currently feel any time I go out en femme, especially if I am going out alone. Be it the first time I went out in public or now.

    Unlike so many others, the only time I can get out is during the week in the daytime. As such I try to take care doing my makeup and selecting what to wear and being care of where I go. Once dressed it takes me forever to leave the security of my motel room and venture out. As your article states I delay going out as I’m not sure if I can pass and if I do get read, how will I react?

    However, once I leave my secure surroundings I enjoy the feeling of being out in public and presenting as a woman. I enjoy the shopping or eating at a restaurant and being referred to as ‘Miss’. There is little to compare to this feeling of being out and free to express myself as a female.

  • George

    Great material here. I'm miles away from what you're describing, Kathy; but I still take it and I'll not just sit on it. It's not exactly a path that's easy to move through, so your terrific encouragement is most timely and appropriate. Thanks!

  • Elena

    Congratulation Kahty for your piece of writing. I'm very shy and so I cannot do it. However I did it, in the night, walking along my neighborhood. Only I can do it on Friday night. I can't drive the car because the police controls every roundabouts in my village and it could be very shameful that they check my identification items while I wear women's clothes. Only I walk no far from my house if I have to run faster. However it's a rewarding experience. I see the world as a woman who is self.confident and elegant. Honesty, few people saw me as a woman: a boy who is sending the dairy news papers in the houses, some people who go to work o go to hunting, but they don't pay me attention. Finally, I feel that going out wearing female dresses is very dangerous, because gangs of young people, who are returning home after a long party night, can attack me. Consequently, I prefer to avoid this kind of situations.

  • mary

    it is the greatest feeling to be in public dressed But to be in SF clothes? is like heaven! it's is because you are sexy and stylus You will not be anonymous
    I love the attention I get when I'm out wearing SF merchandise :-)

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