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How to Overcome Obstacles as a Crossdresser


So, you want to let your family and friends know that you are a transgender or a cross-dresser? Should you come out at all?

Well, the decision to come out and let your family and friends know that you are a transgender, transsexual, or cross-dresser is entirely yours. If you are planning to change your physical body by going through hormone therapy and gender assignment procedures, you will need to inform your parents and friends. But whether you actually want to come out if you are a cross-dresser is something that you will have to think carefully about. Once you are out, you are out. There is no going back.

Coming out is definitely one of the biggest obstacles you are going to face. If you are a cross-dresser and are perfectly happy being in the closet, you can easily do it. But you surely owe a disclosure to your life partner.

Self-confidence is the key here. To be confident, you need to accept who you are. You like to dress up like women, but that doesn’t make you a bad person. You are fine being a man, you are not gay, you are probably not going to go for medical interventions for changing your gender…or maybe you are.

The idea is to understand what you are, what you would like to do, and are you ready to accept yourself the way you are. If you don’t accept yourself as you are, how are your parents going to understand it? If you can’t explain things to yourself, how are you going to explain it to your wife?

Even for cross-dressers who are not transsexuals, letting their wives or parents know about it is sometimes important. If you are married, are about to tie the knot, or in a committed relationship, you need to be honest with your partner. Deceit can never do anything good for your relationship. The best thing to do is to sit your wife down and let her know about how you sometimes like to get dressed as a woman. It will probably come as a shock to her at first.

Let her know that you don’t want to become a woman, but you just like to dress up like one occasionally. Let her know you really do love her and your relationship will be as normal as any other couple, except for that one thing. Tell her that you are not a homosexual or transsexual, that is, you are not at all interested in men and neither do you want to be a woman for life. You are a man who just likes to dress up like a woman to stay in touch with your feminine side.

Being prepared with some form of literature on cross-dressers or transgenders will be quite helpful. Give your partner space. Let her think about it. Explore the answers to all her questions. If you have a few cross-dresser friends, it may be worthwhile to introduce her to them. Wives of your cross-dresser friends can be really helpful at this stage.

Let her know that you would like to live your life with her. It would not make any difference to your sexual or emotional relationships. Many cross-dressers have a successful relationship simply because they choose to come out to their partners.

As far as parents and friends and co-workers are concerned, think about it carefully. If you are a cross-dresser interested in women, you may never have to do it. If you want to go for changing your gender, you will definitely have to do it before going for all the medical interventions. You especially owe this to your parents and close friends.

Letting your close ones know that you are a cross-dresser or transgender is not the only obstacle. If you do decide to come out, society is going to present the biggest obstacles. Your parents or wife may want you to get treatment… “You can be cured if you just consult a good doctor”…this is quite a common sentence most of you would hear.

Many people are going to target you. You don’t know how your neighbors would react. Is your landlord going to be okay with it, is your boss going to accept it, will your co-workers make fun of you, etc, etc, etc. Simply, you just need to be prepared.

You may be an easy target for bullies, people who think cross-dressers or transgenders deserve to die. Even your preacher may preach against this practice and tell you that you are indulging in a sin and God is never going to forgive you. Again, you need to be prepared for this.

Dating is another thing you should think about. If you are a cross-dresser and not a transgender, you would be dating regular women. Nothing wrong with it, you are a normal man interested in regular women. You like dating and going out and having a great time with regular women. So, nothing should stop you.

But there will come a point in your relationship where you may want to take the next step. Maybe this is the time to let her know you are a cross-dresser. You don’t want to get too deeply involved with a woman and then be dumped by her for hiding this, right? So, pick a good time in your relationship and share your “secret”.

Now, I am going to come back to same point here. Accept yourself. If you accept yourself the way you are, no one can convince you to go for “treatment”. You will be prepared to answer the barbed comments of your co-workers.

You also need to learn as much as possible. Read, learn about yourself, interact with other cross-dressers, and then you will feel more confident. There are many celebrities who are cross-dressers or transgenders and have opened up about it. The lead singer of Nirvana, Kurt Cobain, was often seen in women’s clothes on stage and he acknowledged that he dressed up as a woman at home, too.

But we are not celebrities. It is always more difficult for people like you and me to open up in public than for celebrities. But it is definitely worth a try. Coming out opens you up and then you can take the next step at living your life the way you want.

Always involve your wife or girlfriend in your cross-dressing efforts. It will help make your relationships strong. Whether you should tell your children or not is another thing. Talk about it with your wife and do what you think is the best for them. Also, it is not assured that if you are a cross-dresser, your children are going to be one, too.

You should also know about your legal rights. Quite a few restaurants and clubs do not allow cross-dressers and transgenders to enter. Your boss may fire you just because of it. But no one has the right to stop you from living your life the way you want. So, you should know your legal rights in case anything like this were to happen with you or your other crossdressing friends. Check out the resource page for links on information to your legal rights and help you can get.

So, now let me just summarize here.

Read and learn as much as possible. There are a lot of resources available online about crossdressing. 

Interact with other gals. There are community sites and forums where you can discuss your fears and obstacles with other cross-dressers.

Accept yourself the way you are. There is nothing wrong with you. Be confident and believe in yourself. You don’t need “treatment”, you are fine the way you are.

Prepare for coming out, at least to your wife or girlfriend. She could turn out to be your best friend when cross-dressing.

Learn about how to be a great looker. If you look terrible in your first few efforts, don’t despair. It will surely get better. All you need is practice, practice, and more practice.


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