Crossdressing is still a big taboo, and it raises fears even in those who don’t practice it.

One of a crossdresser’s biggest fears is that of being “caught” doing it. It starts with the risk that the boy who is trying on his mother’s or sister’s bra will be caught by the real owner of the piece, or even by his father or someone else.

The boy realizes that he likes to wear a bra – or any other feminine clothing – and feels insecure:

“I’m a boy. I’m a man. But I like women’s clothes. Do I want to be a woman? Am I trans? What is my sexual orientation?”

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After a while, he decides to buy his own clothes.

“If I buy in a store, will anyone notice? What if I meet someone I know? If I buy online and someone opens my order and finds out everything?”

Then, unable to practice crossdressing explicitly, he has the idea of practicing underdressing outside the home.

“I’m wearing panties and a bra under my men’s clothes. What if someone notices? What if the panties show? What if the outline of the bra shows? What if I get sick and the doctors discover my ‘secret’?”

Then he starts a relationship – with a woman. More fears, more doubts.

“Do I tell her? What about the temptation to try on her clothes in secret? Would hiding my crossdressing or wearing her clothes in secret be cheating?”

The crossdresser experiences several fears throughout their experience. But whoever is next to him too.

Imagine the mother catching her son wearing her clothes.

“Is this normal? Should I take him to a psychologist? Is this an illness? Does he want to be a woman? Does he like men?”

Some parents are more violent and apply punishments and beatings to “correct” their child. Others try to talk to him. But still they are afraid. For them, their son is not “normal” now.

The situation is made worse by the fear of other people finding out. “What if my son is judged by others? Or even attacked for wearing women’s clothing?”

In the romantic field, the situation is no different. It would be a shock for a woman to hear from her husband that he likes to wear women’s clothes – even worse would be to catch him in that condition.

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“Does he want to be like me? Does he want to compete with me? Does he want to be a woman? Does he really like women? Does he really like me? What if he’s using me as a facade? What if he wants a man? What if he wants me? Exchange for a man?”

A woman in this condition may even have her self-esteem compromised: “Maybe I’m not a good woman, that’s why he’s acting like this?”

Furthermore, it is clear that women, sisters and mothers of crossdressers will not feel comfortable discovering that their husbands, boyfriends, brothers and children were secretly wearing their clothes – including their underwear. In addition to being an invasion of privacy, this may be unhygienic.

To better deal with taboos and fears, the first step is information. Understanding the difference between gender identity, gender expression, sexuality and other topics is very important.

It is also necessary to have dialogue. This resolves many doubts between the crossdresser and his mother, sister or wife. Dialogue must be respected by both sides. If the crossdresser wants to have the freedom to express his feminine side, he must do so with his own clothes – after all, it is not very hygienic to wear other people’s panties. Furthermore, most women expect to have a relationship with a certain profile of man, which often does not fit into a crossdresser. Many women even tolerate their husbands’ crossdressing, but prefer not to see it in practice. It’s their right. Be the man she wants to see and have by her side when you are with her.

Obviously there are exceptions: Women can benefit from their husbands/boyfriends’ crossdressing: from combining the practice with sexual games to even having a partner who understands them better as a woman and helps them with everyday issues.

Transparency is also important. Many women feel betrayed when they discover “by chance” that their husbands dress like her. Many men hide the practice for fear of losing their girlfriend or wife. On the other hand, when people talk about crossdressing they may walk away. It’s a big taboo.

It is very important that you evaluate your crossdressing if you enter into a relationship. If you realize that she would not support your hobby, consider not entering into the relationship or staying away from crossdressing. Life is made of choices, and each choice is a renunciation. Evaluate what is best for you in the long term. Crossdressing in secret while your wife is away is safe… until she arrives early!

Psychological help can be very positive for the crossdresser – and their family members. It helps to establish dialogue, clarify doubts and improve relationships. Consider couples or family therapy. Individually, therapy will show you paths and facilitate decision-making, reducing fear.

– What fears do you have regarding crossdressing?

– Do you think your mother, sister, girlfriend or wife has any fears about your crossdressing?

– How do you and those close to you deal with these fears?


Marie Claire


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Active Member
6 days ago

Thank you for a wonderful and well thought out article. I was impressed at how you captured pretty much all our fears or rather worries for many. In many instances, fear is too strong of a word. I do not fear many/most of the circumstances you mention, it is more that I worry that others will not understand and I do not really want to have to explain myself. I was never fearful of being “caught” by my wife but was rather worried she might not understand or would panic before thinking about it, so I simply have told her… Read more »

Julianne Mitchell
6 days ago

Thank you so much for the article, writings like these remind us all that we are not alone in how we feel and these fears / worries are real . I am sitting reading and writing this after a night for the first time in almost two years being able to fully dress and venture out . My wife is only partially supportive funny she was more supportive earlier in our marriage when she thought it was just a fetish . I came out to her fully about 7 or 8 years ago and it has been a struggle ever… Read more »

Julie Day
Trusted Member
1 day ago

Julianne, I think you would love a makeover. I just look for trans friendly salons and just email them. I tell them I am transgender and are just starting your transition. I am also planning on taking makeup lessons. Like you I LOVE going out and presenting myself as my feminine self. Best wishes, Julie

Erika Bell
Active Member
4 days ago

Spot on. Well said. And great questions to ask.

Jane Don
Active Member
3 days ago

For some of us it’s all about Money– I “”Literally”” have only One thing that stops me being more Public with dressing–I need to keep my Job–

Cassie Jayson
Trusted Member
2 days ago

Your story brought to mind a weekly conversation with my Ex. When I am dressed and ready to go out she says ‘I suppose you think you are prettier than I am ‘. I just look at her and think to myself that I only want to be as pretty as I can be. I have to be very careful to keep that statement in my head.


Julie Day
Trusted Member
1 day ago

Love the insight into the consequences of crossdressing, and why others do not see it as something positive. My wife does not support or accept my feminine side. She has made the ultimatum to leave if I continue to do it. I do love my wife, but I do this for me, I find it such an important part of who I am. I have had to modify when and where I dress, but these wonderful feminine feeling will never go away. Hopefully this will never be an issue with our relationship and love for one another. It is still… Read more »

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