6 Helpful Crossdressing Tips for Your First Experience

Sunday, June 02, 2019 1:06 AM | Deleted user

6 Helpful Crossdressing Tips for Your First Experience

Have you been wondering about crossdressing for the first time? Fear and worry have held you back. But now you are going to take the big plunge and need crossdressing tips.

OMG, what if people point and stare, or worse say nasty things? Don't feel alone, we all have had our first crossdressing experience in public. Read on for 6 helpful crossdressing tips for your first experience. 

Break Through the Fear

You’re looking at your first step out in fem. Every crossdresser remembers his first time out—I remember mine. You will remember yours and be able to relate it to others who are struggling as you are now.

The truth is you are walking on a very well worn path where MILLIONS of men have walked before you. 

You are not weird. 

You are not perverted. 

You are not bad. 

You are just You. Just like I am still me in my dress. Many of us have had to get over all kinds of negative feelings.

Please remember that you are simply expressing who you are. Too many people let fear and the dark areas of their minds rule their life. Look beyond; it takes courage to go to the next level in most things in life.

It's Time to Use These Crossdressing Tips

Time to be you. Maybe you’ve worked most of your life, like me, and have always been there for others. It’s time to look in the mirror and say, “It’s my turn!” 

You, like me, want to dress like a woman when “she” knocks on your mental door. You don’t know why this comes to you, but it does. It also comes to millions of other men. 

You are not alone. 

You do belong. 

You are worthy.

I suggest you read some of my other articles. I don’t have all the answers, but I can relay my perspective and advice from my personal experiences. It is my genuine hope that it can help you in some way.

Now is the time to take action. Why are you waiting to have a complete, fulfilling life? Let's dive into those crossdressing tips to get you started in the right direction.

1) Prepare Before You Step Out the Door

The most important crossdressing tip for your first experience is to be prepared. The more you do to prepare, the less fear and anxiety you’ll have. 

  • Pick your venue. Visit it in male mode, we call it Drab, and get the lay of the land. 
  • Pick your outfit. Make sure it works in your planned venue.
  • Pick your timing. Don’t go when it’s too busy and hectic or vacant. You want time to converse with the wait staff.  

2) Be Confident

Keep a good posture. Stand up straight, think positive, and be as confident as you can. Don’t try to hide or shrink back. It’s better to be out there versus timid.

When you walk, don’t go for eye contact. If you do, you would wonder what she/he is thinking, and your mind will create all kinds of negative thoughts. If you do, just give a nice smile and look beyond at something more distant. 

As you walk, you may pass people who giggle or chuckle after you go by. Don't obsess over it. 

What I do is tell myself that they just shared a joke. Then I quickly dismiss them. By the way, this rarely happens to me.

Something else I tell myself when I'm being stared at is that the person lives such a boring life and I just gave him the gift of a great conversation piece. He came across a guy in a dress, but that person was nice, kind, respectful and gracious. 

That takes away their concept that a man in a dress is bad or wrong. Your positive actions negate their negative perceptions.

3) Build Relationships With the Staff 

This is one of the most important crossdressing tips. Build good if not great relationships with the staff at what will become your regular crossdressing destination. 

At first, it’s more about you building those relationships versus your being out dressed. Once you’ve built the relationship, it can become about you being there in fem. They will have accepted you and now they will be very supportive and protective of you.

Learn the staff's names and use them. When you return, use their names and always be kind and respectful. Everyone likes to be recognized. 

The more you do the easier being in fem becomes and your fem self will love it more. Never make a big deal about you in a dress. Just be one of the women there. 

Also, never talk about your rights as a woman. Don’t be pushy. Go with their flow.

If you have a bar or food tab, make sure to tip well. Then, come back dressed a few days later and repeat it. You’re becoming a regular who is nice, kind, fun, and a decent tipper. 

Never get into an argument or raise your voice. Don't try to hide. Instead, be pro-active and accept the fact that you will not pass. 

People in the Hospitality Industry will treat you as a woman. That is how they are trained, and most of society follows this norm now. 

4) Restroom Issues

Make sure that you leave your home on empty, so you don’t have to use a restroom. Eat light and drink light. Don’t stay too long that you may have to go to the restroom.

After you have become a regular, bring it up to the manager whom you have gotten to know. Do it in a quiet, gentle, and supportive of the establishment way. 

If you are talking with an employee, they are paid to be nice and not give you any problems. You are safe with them. Mirror it back.

If you find a server you like you may want to ask when they work, or mention that you’ll be back again on a certain day. This helps to start building that rapport.

This is how my crossdressing friend and I did it with our local redneck watering hole. We are now welcomed with open arms. We also use the lady’s room—still with caution. 

If you want more crossdressing tips on using the restroom please check out my other article “Where to Go When You Need to Go.” This is one of my commonly asked crossdressing tips that always seems to be a major concern for new crossdressers.

5) Managing Your Femme Self

You probably don’t have a perfect female voice, so don’t try to hide your male voice. At the same time let your feminine gentle and kind side of you be reflected in the tone of your voice, what you say and how you act.

When I go from drab to dress, I always find myself taking on a beautiful, gentle, kind radiance that I express to others. Also, my male stress, worry, and heaviness of life melt away to let a happier me shine through.

It is the extreme few who pass as a gendered woman and that is with years of dedicated work. 

Be nice. Nice always begets nice. At the same time, a woman may give you a compliment like: “you are doing a nice job” or “that is a nice outfit,” or “I like your shoes.” 

Give the gift back. How about, “This is all new to me. What I’ve learned is that it’s not easy being a girl,” or “Now I know what women mean when they say, ‘men are clueless’."

Connect with the person’s humanity. It usually works. 

6) The Best Place to Come Out is a Cruise

If you could find a place that has an encouraging environment that supported you celebrating your fem self would you go? Think of a place that totally accepts your crossdressing 24/7/365. Imagine a place where you can meet thousands of open-minded people. 

Visualize being dressed as the woman you want to be at dinner, shopping, or on an adventure in the jungle. There is only one situation that brings it all together for you. 

That is on a cruise with us.

On a cruise with CrossdressTravel.com, you can dress as much or as little as you wish. You can go in "boy mode" for a few days and see how we are treated.  If you decide you are not ready and spend the entire cruise in boy mode, then that’s ok too. 

When you are ready, we will be there. 

Even if you never dress on the cruise, you will still learn a lot, meet good people, and have a great cruise. Regardless, it’s a win-win.

When you do step out dressed, join us in our “She Pack”. You may want to stay in the middle of it and that’s OK. I can tell you from experience that you won’t be there long because you will want to step out and shine.


Well, you read this entire article, so you must be giving your first crossdressing experience some serious thought. Check out our future travel plans and the blog for more great crossdressing tips


Dream Vacations

We support traveling in femme and general crossdressing.  

Contact us for more information. 


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