Crossdressing Men: Breaking Through the Boundaries of Gender

It takes a lot of courage for a man to be a crossdresser. It takes even more courage to wear those clothes out of the closet! There are so many myths and labels and prejudiced ideas towards crossdressing men out there today, that it is sometimes hard for these men to feel the freedom to really be themselves. So what makes a man want to wear women’s clothing? There are many different reasons that men enjoy dressing in female clothes, and not all of them have to do with sex.

Are All Crossdressing Men Gay?


Absolutely not. I have known a lot of men who crossdress, who are not interested in other men at all. They are often married men who are completely heterosexual, only they enjoy the feel of silky satin panties or sexy nylons on their skin. While it is the exception and not the norm, in some instances their wives are aware of their crossdressing needs and fully embrace this… and why not? After all, a crossdressing man is the most fun to go shopping with!

No worries about them whining that they want to go home, or that they’d rather go to Home Depot than Victoria’s Secret, and if you are really lucky and wear a similar size, then you can borrow clothes from each other, thereby doubling your wardrobe! However, just because the wife or girlfriend is comfortable with her crossdressing male partner does not necessarily mean that they are comfortable with the rest of the free world knowing about it.

This often times means that crossdressing escapades are kept behind bedroom doors or in the privacy of their own home, or that the taboo items are worn in secret under ‘normal’ male clothing. Just because the wife or girlfriend is accepting of it unfortunately doesn’t mean the employer necessarily will be.

For many crossdressing men, they feel uneasy telling their wives or girlfriends about their desires to dress in female clothing. They are concerned about the reaction they may get from their partner if they reveal these deepest of desires. Most times it does not go over well and all do not live happily ever after. This is usually because the partner doesn’t take the time to ask questions about her crossdressing man’s reasons for wanting to dress this way. They worry that this means he is gay, or at the very least, bisexual.

For some, knowing that a man enjoys wearing panties or bras seems to totally strip away any sense of masculinity in their eyes. Even if he only wears these items in the bedroom or during his private time, they can no longer look at him as the provider, the protector, the man they thought he was. This causes most crossdressing men to keep their hobby a secret, and sometimes can put a strain on relationships.

It’s often a double edged sword… the crossdressing man sometimes resents his partner for not being able to reveal this part of himself to her. But on the other hand, if he does reveal it, then he often times will lose her as a part of his life. This is why I say that crossdressers have a lot of courage… it takes guts to wear panties.

Ok Then, Do Men Who Crossdressers Actually Want To Be Women?


Not necessarily. Wearing women’s clothing is not always an indication of a man’s sexuality. Some men just like the feel of the clothing on their skin. They feel somehow comforted when the slip on a nice pair of pantyhose or a satin bra. It could be that they are missing something from their childhood and these items bring back a sense of security or comfort.

Perhaps they have high stress jobs with a lot of responsibility, and the feel of a silky slip reminds them of being comforted by their mother when they were young and had no responsibility. Or it could just be that they like pantyhose! Many men are perfectly happy with their male bodies and their male sexuality. The clothing they put on over that body has no effect on their sexual preference or the desire to change their gender.

On the other hand, some males who crossdress do so because they truly do want to become women. They may feel that although they were born with male bodies, that their personality is female, and they may have had these instincts and desires for as long as they can remember… including the earliest memories of being yong.

These men should most often be refered to as ‘transgendered’ and not just ‘crossdressers’, although many times they are grouped together by the general public due to lack of knowledge and understanding. Which is unfortunate, because one of the main things a transgender or crossdresser needs is a little understanding from those around him.

So What Kind Of A Guy Would Crossdress?


All kinds. There are crossdressers in every walk of life… I have had the privilege of speaking to crossdressing men of all types throughout the years, and in every profession, including doctors, lawyers, bankers, politicians, professional sports players, CEO’s of big corporations, fast-food restaurant managers, garbage collectors, school teachers, you name it!

And they are always comforted when I let them know that they are not alone in their secrets. You may be shocked if you were given x-ray glasses for just one day and discovered how many men in your daily life are wearing panties and/or bras underneath those business suits.

I Just Found Out My Friend/Boyfriend/Husband Is a Crossdresser… What Now?


The most important thing is… don’t freak out. Your crossdressing male is still the same person he was before you found out he liked to wear women’s clothing. Try to be non-judgmental, open, and willing to listen. Don’t get angry or upset with him, give him a chance to tell you how he’s feeling and what this part of his life means to him. If you want to know something, don’t be afraid to ask him questions.

Be honest and up front with him… are you worried he might be gay or bisexual? Ask him! Do you want to know how long he’s been doing this? He may be relieved to tell you! Want to know what size panties he wears so you can share with him? Ok, I know, that may be rushing it a bit… but why not? He may love it if you show your acceptance of him and offer to help him with his crossdressing hobby. On the other hand, he may say although he’s glad you’re okay with it, he would rather keep as a private and personal thing.

This is okay too, and whatever he decides to do, you should try and understand and give him his own space. He may be uncertain of how you will react after you’ve had time to think about it and is nervous for what the future holds. Just give him time, patience and love, and you may just find that you not only have all the qualities you loved in your male friend, but also all the qualities you love in a good girl friend.

I’m A Crossdresser And I Just Got Busted! What Now?


The most important thing is… don’t freak out. I know what you’re thinking… wait, didn’t you already say that to everyone else? Yes, I did, but it’s just as important for you to stay calm. The person who found you out may be feeling a lot of different and confused emotions right now and may be afraid of what it means that you are a crossdresser. The best thing to do is give them some time to come to terms with what they’ve learned, and let it sink in a little bit.

They may want to talk… if they do, let them ask you any questions they may have, and try to explain yourself the best way you know how. Be honest… if you don’t really know why you like to crossdress, then tell them so. Don’t make something up because you think that’s what they want to hear. They will eventually find out if you don’t lay the cards on the line. And be prepared for rejection… not everyone has it in them to accept the unknown or the unfamiliar.

If this happens, dust yourself off and keep on plugging away. It is better to be true to yourself and be who you are, then to smother that part of you and resent someone else for it! You will find that there are people who will accept and love you for who you are, just don’t give up.

The Final Thought on Crossdressing


Crossdressing has been going on for hundreds or thousands of years and by many powerful men throughout history. In some countries, men still wear skits and dresses and it’s just another part of their tradition.

Don’t let the clothing someone is wearing influence your thought of them as a person, and don’t let your choice of clothing make you feel like less of a person, either. We are all beautifully unique on the inside and out, so let’s embrace that with open arms.

Give one of our Feminization Mistresses a call, today!

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