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!


  • Gail

    The first to yards are, for me, in the rear view mirror, and rapidly receding.
    The final 10 yards, on the other hand, are rapidly approaching, and for me, at least, are bittersweet.
    I've been dressing for the better part of fifty years, but outside of a handful of trips to Las Vegas, and Seattle for some weekend highly enjoyable public excursions, and some hometown trips to the mall, my crossdressing has been a private, secret adventure unknown to family, friends or co workers.

    This secrecy, perhaps cowardice is a more apt descriptor, came with a price, In my 50s I flirted with transitioning and went so far to begin hormone therapy, but just when the hormones were starting to have a noticeable effect I discontinued therapy. In short, I was afraid.
    This fear, in part, was a product of keeping my love of all things feminine secret.

    My recommendation for young crossdressers, especially those who are favorably disposed to transitioning, be open and public about your desires.
    Don't shroud them in a veil of secrecy.

    The first 10 yards, and the final 10 yards are both worthy of discussion.

  • Ryan

    I'm so grateful for this website and all of it's wonderful advice. I'm 36 years old, and for pretty much all of my life, I've thought about becoming a woman. I was raised by my mom, so right there is the feminine influence. But I've always felt more feminine than masculine. When I was a teenager I started trying on my mom's lingerie, and I like it, I enjoyed it. Then I started "creating" women's clothing, and experimenting with designs. Cutting up old jeans, sweats, t-shirts, etc. Because I couldnt buy lingerie.

    I've gone back and forth with these feelings, "should I?" or "shouldn't I?". And again I'm back to, "I should", and I'd like to stay here. A full M to F transition would mean more surgeries, and I've had my share. so I've decided to really experiment with crossdressing, but with actual women's clothes, lingerie, etc. Life is short and we only get one go around, and I want to be happy.

    I'm amazed at all of the support that people have shown me as well. I've told some friends how I feel, a few family members. And like one section here says "Not everyone needs to know. I found a crossdressers boutique near me and I've already been there once, and I hope to go back very very soon to make a few purchases. All due respect to SF. Ive just had trouble buying items online. I'd like to be able to see, in person what I'm buying. I even bought a prepaid credit card, so I keep things private.

    Im excited and a little nervous, but more excited to take this journey. And maybe make that full transition.

    Thank you En Femme!!

  • Thomas

    thank you for this article, it completely describes my first time out. Dressing and the make-up. was doing that for a few weeks. Ordered my purse and then made up my mind to go out. I was so scared and yet excited!!! As your article suggests I went out at night afraid my neighbors would see me and how I would react if they did. But I made it down the stairs and to my car, the air between my legs was invigorating!!! I just drove around the block, but it was the most exciting drive I have ever taken. I have since gone to a drive through and ordered a meal using my bank debit card which was an adrenaline rush. I guess my question would be using my credit cards at retailers, since they suggest I am not who I appear to be. How does one work around that? Do I offer to take off my wig?

  • Kim

    Once again Kathy you have touched on so many of my experiences and feelings. It’s almost as if you were there with me writing down notes in a journal, your writings are so spot on to mine, it’s quite relieving to know someone else felt the same way about “The first 10 yards”. For me, the first 10 yards was alongside my house – literally. I described my first outing in an earlier post where I chronicled my trip to the mall – so exciting! But before I had the nerve to do that – I needed to be in a secure environment but I still wanted to be seen as a woman – a sexy and desirable woman. That’s what started me dressing in the first place, the beautiful Italian trapeze artist in that gorgeous thong bodysuit and nude back seam pantyhose I saw on TV – I needed the pleasure she felt as she performed freely knowing she was beautiful, sexy and desired by men. But how? How could I do that? So, I came up with a plan to dress the way I loved, the way that made me feel the pleasure of being a woman and yes, have the sexual satisfaction that I craved so much being a woman.
    The house I owned in my early 30’s had a side gate alongside the garage facing the street. My neighbor’s house on that side had no windows, the houses on the other side of the street could not see me in the area alongside my house. So, dressed in my favorite black, mock neck thong Nordstrom tactel nylon bodysuit a size too small so those leg openings were at the waistband of my Wolford High Heel STW back seam sheer 15 denier black pantyhose – I sashayed my lovely figure alongside my house with the gate open – OMG it was a huge step. I didn’t know it at the time but that was the day my water meter guy walked along the sidewalk checking the water meters – what a great time to test my courage. I hear his truck pull up, the excitement mounts. His truck door shuts, and I hear the sound of him opening the cement cover to the water meter at the sidewalk – that’s my cue. With my 5 inch black pumps, I strut outside my comfort zone, beyond the gate to get his attention. He sees me and stops dead in his tracks. I smile, turn and walk back beside my house pretending to be on my cell. I turn around and he’s still there! I walk a bit more, laugh on the phone, shaking a bit as I smooth up my nylons with my free hand, he eventually walks down the street. OMG – I did it! I actually did it! Then, to my amazement he returns, pretending to look at the meter again – he does this 5 times – each time stopping to check me out in my gorgeous bodysuit and Wolford pantyhose, what a beautiful tingling feeling I had!
    It was shortly after that I had the courage to don a skirt, grab a purse and drive to the mall. Whew! It took me a long time to get to this point but it was soooo worth it! Thanks again Kathy for allowing me to share. Girls, you are not alone! Hugs, Kim

  • M. J.

    Hi Kathy honey its good to see your article again as I said about a month ago honey how right you are dear getting you butt out of the car and getting started those first few steps depending on how long it's been since you wore heels without falling or stumbling naa women do it too we all need some of those high heeled sneakers that were out a few years ago okay maybe more than a few years ago you never know when you might need to make a mad dash for the car lol M.J.

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