The psychology of crossdressing: Why do you dress like a woman?

Marie Claire October 16, 2023 Hodgepodge 26

You’ve probably considered seeking psychological help. “I’m a man but I like feminine things. Why? Is this normal? Do I have to accept myself or “cure” this?”

We tend to naturally like some things and dislike others. Environmental aspects can also develop preferences or strongly influence us – like a trigger.

In childhood, a boy who lives with his mother and sisters and does not have a father figure present may have a greater tendency to be attracted to the feminine side. For example: having more feminine behaviors or being more curious to try something of the opposite sex.

Another boy might notice a stray pair of panties is more attractive—whether it’s the fabric or the pattern than his drab underwear. He may try on such panties and simply enjoy the experience. Another example is finding a princess dress to be much more attractive than a male superhero costume.

Another boy may might be pushed into crossdressing out of his will—like an older sister who dresses him as a girl for fun or his mother who puts him in a dress for a costume party or other event. Once they have contact with this experience, they may come to enjoy doing it and feel the desire to repeat it.

In adolescence, the process of growth and puberty, from hormones to the appearance of hair and breasts, enhances the difference between boys and girls.

A boy who notices girls at school starting to wear bras might be curious and want to try one on.

The boy tries on the bra and likes the feeling of wearing one. Perhaps, too, he feels a sexual stimulus – remember that in adolescence hormones skyrocket.

If he likes the experience, he will tend to repeat it. He will want to have his own bras and adopt them in his daily life.

In adult life, a man who is not satisfied with his masculine personality – such as having little muscle or not being successful with women – may try to compensate for this in other ways.

He will be able to develop a feminine personality by dressing like a woman.

Aside from a possible sexual pleasure, he may enjoy the feeling of wearing lingerie, a dress, makeup, and a wig. He can look in the mirror and feel that his female presentation is truer than his male self. This could raise his self-esteem and help to overcome his need to compensate for the frustration caused by the failures on the male side.

If you are – or are thinking of becoming – an artist, you might develop an opposite-sex persona through crossdressing. If you like Womanless, you can become a reference in this segment. The internet can help you become an influencer through crossdressing: something that can be very productive, interesting, fun… and profitable.

There is a downside to this bias: Unless you identify as a transgender person, your feminine side will never replace your masculine one. You can explore your feminine persona, but that doesn’t stop you from developing as a man. You will not be able to be a woman 24 hours a day, nor will you be able to escape your masculine obligations at home and at work. Balance is the secret.

Many crossdressers reject the sexual component of this practice as others find sexual pleasure in crossdressing; it is essential to understand this. In some instances, you may develop a harmful compulsion, not having control over your desires, and even potentially expose yourself to dangerous situations. This could become unhealthy and require professional help.

Another positive point is learning skills that may become useful. Learning more about women’s clothing can help you in a loving relationship. Situations such as choosing clothes as a gift for a girlfriend or learning about makeup could allow you to work as a makeup artist. Crossdressing can develop your empathy with the opposite sex: perhaps the time your wife takes to get ready is not as time-consuming as you once thought.

Crossdressing can also combat stress: if you enjoy doing it, it can relax and give you pleasure – I don’t mean sexual pleasure, but the pleasure of doing something you enjoy. It may even serve as an escape when practiced in a healthy way

If you still don’t know why you like to dress as a woman, look for those elements in your life that could justify or support this preference. Therapy – or even self-therapy and self-knowledge – can be key.

Some questions you can ask yourself: 1) Have I always liked women’s clothing? 2) I was influenced by the environment or other people. 3) Do I think women’s clothes are more beautiful than men’s? 4) Do I feel sexual pleasure when dressing like a woman? Only that? 5) Do I use crossdressing to compensate for social, physical, and other failures on my male side? 6) What have I learned, or can I learn from crossdressing? 7) Can I be successful by dressing like a woman? 8) Is my crossdressing healthy? 9) Do I feel shame, guilt, or remorse when I crossdress? 10) Did the lack of a male figure in childhood influence me?

Having answers to these and other questions is essential for the healthy practice of crossdressing. Unhealthy crossdressing will lead to impulses, guilt, regrets, regrets, and other social, physical, emotional, and financial losses.

– Have you ever wondered why you like to dress like a woman?

– Do you believe you were influenced in childhood or adolescence?

– Have you ever had any kind of therapy to find out more about it?