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7 Steps to Prepare for Your First Time Out

Overcoming Your Fear of Venturing Out in Public: 7 Steps to Prepare for Your First Time Out

One of the most frightening and yet exhilarating experiences for a CD is to take those first steps into the public eye. We all think about it, fantasize about it and crave the experience, but to actually do it is such a daunting move that many of us never take the step. I’m here to tell you that your fears, while understandable, are completely unfounded if you take precautions to protect yourself, your image and your identity. Your reward for taking those first steps will be unmitigated joy and exhilaration.

Like a lot of you, I’m a CD in my “second life” and a full alpha man in my real life, so taking my first steps out had to be done with complete discretion and anonymity. The good news is, that’s an easy thing to do with proper planning, good makeup and a great outfit. The more difficult part is convincing yourself that (i) you deserve to be seen, and (ii) you look so good that nobody will notice. But, even if they do, girl, just be assured that they won’t say anything and may even be secretly wishing they were you.

I’m going to assume that crossdressing is something you currently do in private and that because of a relationship, job, living conditions, or other reason you can never let anybody become aware of your desire to dress like a sexy woman. I was married when I took my first leap into the rabbit hole of crossdressing. My wife did not approve and I was in a highly visible position, so needless to say, I could never “come out” as a CD. Becca had to stay anonymous. Like many of you, I yearned to be out in public, but I wasn’t sure if I’d ever be able to take the steps. So, I started to make a plan that would allow me to systematically overcome my fears and to get into a position where I could set my feminine self free.

Many of you have already taken at least some these steps, or could add steps of your own. After all, the journey out is unique to all of us, as we all have different living conditions and/or insecurities about how we look. So, here’s the plan I developed and followed all the way down the rabbit hole till I finally strapped on the heels and introduced my girl side to the world.

1. Talk to others who've done it.

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I combed the Internet and chat rooms to find people who had experienced what I was going through. There weren’t many online places available when I started, but I would search and talk to as many people as I could to get their perspective. This is one of the biggest reasons we created Circle of Q, so you can come to talk to gurls like me who have already taken the leap and can help you overcome your fears.

The best advice I heard was, “be confident and act like you belong there.” That sounds easy, doesn’t it? Yeah, right! Lol. I heard that advice and my mind immediately produced a list of reasons why that might work for others, but not for me: I’m too tall, my jawline is too pronounced, my walk is still too manly, etc. So as I came up with my own excuses, I looked for ways to eliminate them. I began to practice walking in heels as often as I could…I kept practicing with my makeup (it’s amazing how contouring can change the shape of your face)…and I started to imagine that even with all of my manly flaws, I might be able to get away with it.

2. Sissify the walk.

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The walk is all-important, gurl. There is nothing quite like the feeling of knowing that your walk is getting attention—and the right attention. When you’re in heels and your hips are swaying with the walk, you will feel like a sexy Goddess on a catwalk. But it takes practice and discipline. The most important discipline you’ll need is to fight the adrenaline that’s rushing through your veins and making you want to walk fast to get it over with. That is the worst thing you can do. Slow it down. Nobody can look good walking fast in heels, no matter how much practice they’ve had (unless you’re Giselle, of course). Force yourself to slow down and focus on how your heels are connected to your hips and how sexy it feels to feel the swish of your dress as you take each step. Practice walking slow in private…maybe set it to a slow count in your head, so that when you are in public and your brain is screaming at you to hurry, you can rely on that count to keep a sexy pace.

3. Find a mentor.

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You might find a mentor as you begin talking to others on Circle of Q. You’ll find that experienced CDs love one thing almost as much as wearing feminine clothes…and that’s talking about wearing feminine clothes. 😊  We all love to talk about our first experience. The crossdressing journey is filled with firsts: first panties, first shoes, first time in makeup, first time in public, first time you’re hit on by a guy, etc. Take advantage of these stories to learn how others dealt with it. You might even find a friend who’d enjoy going with you for your first public outing. It’s always easier when you’re with somebody and having a gurl next to you that has experienced exactly what you’re experiencing is a godsend.

You can also search out dominant women to help you with your journey. There are some dommes who truly enjoy helping men like you become the gurl or sissy you want to be. The good ones know how to encourage you to take those first steps out and to give you the confidence you need to do it.

I’ve met a number of dommes throughout the world and can tell you that Ms. Ava is the most genuine, compassionate and caring one that I’ve ever known. She’s made it her mission to help as many of us as possible embrace our feminine side and to find social support and connections through this site.

4. Build confidence through clothes and makeup.

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The most important thing to do is to feel sexy in your own skin. To do that, play with your look. We all have different shapes and look good in different clothes. Online shopping makes it easy to experiment and to find that look that makes your heart flutter when you look in a mirror. Once you find it, flaunt it in private. Practice being the best gurl you can be. Some people enjoy coming up with a mantra, a saying that you repeat yourself to give you that confidence you need. It could be “I’m a sexy, confident gurl” or “I have legs to die for and everybody wants to be me” or “I’m a hottie, men want me and women want to be me.” 😊 Use that mantra when you’re out to keep your mind on how you really feel.

Let’s talk about makeup. Choosing makeup was like trying to figure out quantum physics and putting it on was like building a nuclear reactor. Because of that, I had no confidence in how I looked. So, here’s some advice…hire a professional. There are crossdresser makeover artists in most major cities in the US.  I’ve been to seven or eight in the US and the UK. When I finally built up the courage to set my first appointment, I was close to hyperventilating, but the woman at the other end of the phone immediately sensed my nervousness and knew exactly what I was going through. She asked for my femme name and called me that throughout the call. She even used feminine pronouns to refer to me and her other clients. This will be the same experience you have with anybody you call in this profession. I was still nervous when the time came for my appointment, but she made me feel comfortable from the moment I walked in as a man till I walked out as a completely transformed, beautiful woman. Which makes me think of another first—the first time you see yourself after a true professional does your makeup. I simply can’t overstate the sheer joy I felt when she finally let me look in the mirror and a gorgeous redhead was looking back at me through my own eyes.  It is life changing.

5. Find places that are “trans friendly.”

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Even though we live in an age where all sexualities are more fully accepted, some places are better to go than others. Try shopping at a mall. The feeling of walking around will be amazing, and you won’t have to talk to anybody if you don’t want to. If you’re really feeling adventurous, stop in at a lingerie store and buy a pair or twelve of panties. 😊

For me, I wanted to dive right in. I was lucky to have my first real outing in Las Vegas and I was told that the Paris casino was the most accepting one on the strip. I parked in the parking garage and made the long walk through the casino to a bar near the back. I was scared to death during the walk, but the fear was mingled with the thrill of just being there. Once I got to the bar, I was relieved to find an empty seat with nobody around me. As I caught my breath and began to sip on my first drink out as a gurl, I finally relaxed a little and looked around. The exhilaration I felt was palpable—it felt so good to have overcome my fear and finally to let my girl out. As I began to feel better, the bartender brought me a drink even though I didn’t order one. When I gave him a questioning look, he pointed to a man at the end of the bar and told me he bought it for me. 😊 But that’s a story for another day.

6. Find a place where nobody knows your name.

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If you’re Norm, you probably shouldn’t go into Cheers, so find a place where you won’t run into anybody you’ll know. Even if you do, the odds of being recognized are slim to none. You’ll spot them long before they spot you. After all, you’re dolled up with an amazing dress and sexy makeup. No one would ever guess what lies beneath.

7. Have a couple drinks and just go do it!

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I can’t stress enough that all you really need is your own confidence to pull this off. For some, confidence comes in wearing the right clothes or the right makeup, or a shot of tequila, but the important thing is for you to know that you’re a bombshell. Beautiful women don’t care if men think they’re sexy; they exude confidence that makes men want them. You can be the same. Show an air of sexiness and indifference. You do that and you’ll be getting all the right kinds of looks…and maybe free drinks. 😊

After you’ve mastered all of these, it’s time to take the leap. Gather up your courage and take those first steps. This is an adventure that you’ll remember the rest of your life. Chances are you’ll end up like every other gurl who just loves to regale others about “her first time out.” It’s a seminal moment for all of us….enjoy yours.

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