So, He Wears Feminine Things: Navigating a Different Relationship


I am writing this specifically for the wife/girlfriend/partner who has discovered that the man in your life secretly wears feminine things or has expressed to you the desire to wear feminine things. I won’t go into the details of exactly how you discovered his secret. What is more important is both how you react to the revelation and how you process your emotions following this discovery.

Most cross-dressing men do so as an outward expression of the feminine energy that exists within them. This is the same energy that makes them kind, compassionate, and empathetic. Instead of being blinded by the shock of discovery, decide if these personality traits are important to you.

Let’s discuss what it means when the man in your life wears feminine things. We’ll also look at the options available to both of you and how these will affect your relationship going forward.

Coping With The Initial Emotional Shock

Finding out that the man in your life crossdresses will always be an emotional shock. The severity of the shock and resulting emotional turmoil will depend on a number of variables. These include your upbringing, your faith, your education, and the expectations you’ve had about your relationship.

The majority of wives and girlfriends that I have counselled in this situation have expressed the following 3 questions though not necessarily in the same order: Is he gay? Is he having an affair? Does he not love me?

I’ll address each of these questions in turn, but first, we need to help you process the emotional shock and turmoil that you are feeling.

The first thing to do is take a few deep breaths and do your best to calm down. I implore you to not make any reactive decisions that could jeopardize your relationship further than you feel it already is. Realize that it is unlikely to be the end of your world or the end of your relationship unless you choose to make it so.

Your man cross-dresses, which is a way of outwardly expressing a deep-seated feminine side of him.  The reason you did not know about because he has endeavored to keep it a secret from you for one reason. He fears damaging a relationship he holds dear and is very important to him.

That inner feminine part of his personality is what makes him the kind, compassionate, and supportive man that you got to know originally. Even though he has been trying to suppress this part of who he is for most of his life, it is part of who he is and will find a way to the surface eventually.

I know that this is all about you and your emotions, but there is something that I need you to do before we go any further.

The mere fact that you have discovered his secret will likely have him feel that the relationship is already lost and his inner dialogue can easily spin out of control. I have seen instances where this has led to self-harm and worse.

I need you to tell him that you need some time to process the shock of the discovery and not to do anything irrational.

How Common Is Cross-Dressing In Men

Even though you’ve never realized it, men who cross-dress to some degree are way more common than you might think. This is not a perversion even though you might think so in the shock when you first discover it. Cross-dressing is an outward expression of something that is a part of him. It is something that likely started as a teen or young man and has been a source of much inner turmoil as he cycled through guilt and reluctant acceptance several times over.

Interestingly, men who cross-dress have become increasingly more common in recent decades than before. There have been a number of studies done and a number of factors have been isolated that contributed to this increase. Before I get into those factors, I want to point out that these factors don’t change a man to make him more feminine. They are factors that make it easier for him to be more in touch with his feminine side that already exists and make it possible to express that in an outward manner.

When looking at gender there is in fact a wide sliding scale between what culture has historically tended to simplify into a binary system of ‘male’ and ‘female’. Your man is a little way along that scale, and truth be told you are too from the opposite direction. He is to all intents and purposes a male and very likely to be comfortable in that role, but with an added feminine component to his personality which our culture provides very little way for him to express.

By way of comparison, ironically, all women in our modern culture can dress either in frilly feminine clothes or in a very masculine way without comment. This same latitude is not given to men, and should they publicly wear anything that is presumed to be in the slightest way feminine, they are usually ridiculed and called any one of a slew of insulting names. In a cruel twist of fate, our culture has decided to define ‘men’ in a very narrow and confining way with very little leeway for creative expression.

When we look at the sliding scale of the two genders in terms of personality traits, there is a greater overlap of the genders than they are separate. For instance, when we look at the personality trait of agreeableness, the overlap of the 2 bell curves for the 2 genders accounts for 90% of all men and women – so only 10% of men are completely on the male end of the agreeableness scale. Many of those 10% are in prison for some sort of violent crime or have given rise to the term toxic masculinity which has become more prevalent in recent years.

What I have found very interesting is that many native, indigenous cultures have long recognized the existence of ‘Two Spirit’ people. Not only recognizing that such people exist, but that they have value within the culture. These are the wise people among them who have empathy for, respect for, and understanding of both primary genders. Such people were and are respected within the tribe, not reviled. They were not seen as less of a man, but rather more of a person as they had the addition of another gender within them.

Factors That Have Contributed To The Increase in Cross-Dressing Among Men

As I mentioned earlier, studies have isolated three contributing factors that have led to the increase in the prevalence of crossdressing among men in recent decades. Please note that these factors are not causative. They don’t cause a man to cross-dress. They are factors that have made it easier to express that feminine side of him that has existed since the day he was born. Let’s look at each of these factors in isolation.

The Progressive Increase Of Oestrogen In Drinking Water Affecting Gender Expression

In 1988 it was estimated that London drinking water had passed through 7 other people before it got to you. A more recent study in 2022 has adjusted that estimate from 7 to 10 people. It was also noted that the Oestrogen from oral contraceptives does not get removed from the water during the recycling/filtration process.

Although estrogen levels are deemed safe for human consumption, there has not yet been any study published on the effects of this existing estrogen level on the psychological development of pre-pubescent males. The report went on to say that until there is additional data to disprove the theory, it is entirely possible that young boys in major cities have become progressively more feminine (psychologically) as a result of the water that they have been drinking while growing up.

It is quite feasible that there are similar estrogen levels in drinking water in other major cities internationally.

The Effect Of Single Parent Households On the Social Development Of Young Boys

The vast majority of single-parent households are those where the child’s mother either has majority custody or full custody of the child/children. I’m not going to get into the reasons why the family court system appears to favour majority custody for mothers as I am not an expert in the matters of family law.

Young children model themselves on those around them when it comes to social development. As a result, a young boy growing up with a single mother will find it far easier to express the feminine energy within his personality as that is the energy he is surrounded with on a daily basis.

If, in addition to the single mother, there is an older sister in the household, the development of the feminine aspects of the young boy’s personality will be even stronger.

As he grows up he will begin to seek ways in which to more fully express the feminine side of who he is as he will have an increasing feeling that there is an aspect of who he is that is missing.

The Increasing Social Acceptance Of Feminine-Expressing Men in Society

Modern society is becoming progressively more accepting of men expressing the feminine aspect of their personality outwardly. Therefore it is highly likely that the man in your life has been wearing more feminine clothing and/or fragrances long before he met or got together with you.

This has left your man with an internal struggle between parts of who he is and will have been trying to suppress his feminine side for the sake of the relationship. The problem with suppressing emotions is that it is like trying to hold an inflated ball under the water. Not only is it exhausting, but eventually the ball will find a way back to the surface.

The same parts of his personality that compel him to dress in a feminine way are likely the same parts of who he is that you fell in love with… the parts that make him kind, loving, and empathetic. Suppressing is feminine will be suppressing the parts that you love about him and making him different from the guys you dated in the past that broke your heart.

The 3 Most Common Questions Asked My Wives/Girlfriends about Crossdressers

I completely understand your feelings of shock as this revelation has caught you completely by surprise no matter how you found out. Every wife/girlfriend that I have worked with has asked me the same three questions, so I include them here as I am sure that they are the questions swirling around in your mind at the moment.

Is He Having An Affair?

Easily the most common question when finding lingerie that clearly does not belong to you is to suspect him of having an affair. I can understand how easy it is to jump to that conclusion when you are looking at lingerie that is in his possession but is not yours. Most women will suspect that it is some sort of keepsake from an affair.

 No, those feminine items are not souvenirs of some sordid affair. Think back to when you were dating him. Did he ever go home with any of your underwear in his pocket as a keepsake? He did not do that then, and he is not doing so now.

He very likely bought each of these things, one by one, on those rare occasions that the opportunity arose. He has been keeping these things carefully hidden somewhere, in constant fear of your reaction and rejection if discovered.

He very likely discarded all of his feminine things when you first got together, believing that this time everything would be different from all the other times in his life that he purged his feminine wardrobe. As a result, the underwear that you have discovered is very likely to have been bought after getting together with you as the expression of his feminine energy is an intricate part of who he is as a person.

Is He Gay?

A surprisingly low percentage of crossdressers are gay, although some are. If you think that he is dressing up to attract gay men, it is estimated that less than 2% of gay men are attracted to crossdressers.

The vast majority of cross-dressers are not gay. They are attracted to women. I am willing to bet that he is attracted to you.

However, there is a larger portion of cross-dressers are often attracted to other men who cross-dress, when they are dressed, though not when they are dressed as men. Most of the time this attraction resembles women with their girlfriends – an opportunity to connect with kindred spirits.

I won’t lie and say that the mutual attraction between crossdressers never becomes sexual. The truth is that more often these are friendships where he is able to freely express that aspect of his personality that he feels he needs to keep suppressed everywhere else.

Twice a year makeover specialist/artist Dafni Coco hosts a “Pass the Wig” party in Madrid. It has all the features of a typical girls’ night out with dinner and dancing but with one difference. All the attendees other than Dafni and her team of stylists and makeup artists are crossdressers – most of whom only have these singular opportunities to let their hair down in the proverbial sense.

Does He Still Love You?

The short answer is YES, even though that might be difficult for you to hear right now. Ironically, statistics show that the vast majority of cross-dressers in a steady relationship greatly value their relationship with their partner.

As a result of this, it massively increases their fear of damaging their relationship. Nearly all of the crossdressers who I have spoken to who are in a relationship yearn to be better understood by their partners. Not because they want to be fully femme 24/7, but rather that they no longer have to suffer the stress of suppressing such a big part of who they are.

What Are Your Options Moving Forward?

Now that you know what you know, you have choices to make regarding your relationship and how to move forward with your life.

The first and biggest decision to make is whether to continue the relationship at all. If your feelings are leaning toward ending the relationship, there is one important thing you need to know before making such a drastic decision. Your man’s cross-dressing is an outward expression of the feminine personality traits that are within him – those same personality traits that attracted you to him in the first place.

Therefore, if you do break things off with him and pursue a relationship with someone new that has the same personality traits there is an above-average chance that the new man in your life will be a crossdresser too.

If you choose to continue the relationship you have a few options that range from forcing him to throw everything away at the one extreme to being an active participant on the other extreme. Let’s look at these options in greater detail.

Forcing Him To Purge Everything

The most common response is to insist your man throw away his stash of feminine clothes and promise never to even think of doing such a thing ever again.

This is also the worst possible thing that you can do as it will erode the fabric of your relationship with him. He will promise. He values the relationship highly and he values you even more.

Every day he will try to keep this promise that he made to you. He will be wracked by guilt every time a feminine thought crosses his mind – and there will be many because of the feminine aspect of his personality.

The truth is that he will not be able to keep his promise in the long run. By making him promise, you will have set him up for guaranteed failure – which will put a new strain on the relationship because he broke a promise that was impossible for him to keep. All you have done is drive him further into the depths of the closet.

Accepting His Crossdressing With Boundaries

Instead of setting your man up for guaranteed failure, a wiser alternative is to accept the situation as a part of who he is as a person. Recognize that this will not go away even if he makes impossible promises. The vast majority of cross-dressers are ‘sometimes’ dressers, with no wish to live full-time as women.

A potential response could be to accept that your man needs to occasionally express his feminine side, and then give him specific opportunities to be able to do so, but state that you do not wish to be directly involved at all. This will very likely be a huge relief for him to be able to, at last, shed the cloak of secrecy he has carried all his life, no longer fearing your unexpected early return home and the trauma of discovery.

A variation on this theme is to connect with a professional makeover service like Dafni Girls in Madrid and Valencia, Spain. Dafni Coco mentioned to me that a number of her regular clients are married men who book a full makeover and a photo shoot involving several outfits. Their wives know the situation but give them the opportunity to express their feminine side safely, but away from home.

Be Actively Involved In His Crossdressing

There is some wisdom in the old expression: ‘If you can’t beat them, join them.’ This leads me to my third possible response, which is to take an active role in his dressing up. There are a number of ways that this can happen.

Some partners help their men when shopping for clothes, either in the store or online. This is always appreciated as most secretive crossdressers won’t know how to properly style an outfit and will often choose outfits that look terrible on their “inverted triangle” body shape. If this feels like something you want to try, be sure to read my article about How To Dress To Your Femme Body Shape when you are finished here so that you can give your man some pointers to look better when dressed up.

Some partners enjoy secretly knowing what their man is wearing under male outer clothes while at work, out visiting with friends, or on a dinner date. I had a friend in college who would insist that her boyfriends wear feminine underwear at all times (24/7) while they were dating. When I pressed her for a reason she said that it virtually eliminated the chance that her boyfriend would be shedding his clothes with any other girl…

There are couples that buy matching sets of underwear or nightwear and enjoy wearing them together. This often leads to incorporating crossdressing into their sex life, role-playing, and enjoying themselves while fully or partly dressed.

The range of options is wide. I’ll just repeat that outright rejection is not the optimal solution and is an unwise choice that will inevitably ruin your relationship.

Crossdressing Makes Him A More Complete Person

Many wives and girlfriends make the assumption that their man is somehow less of a person by being so in touch with their feminine side. Thinking that your man is less of a man than other men you know because of this is a false supposition.

Think of it this way, if you insist that he give up/remove the feminine part of who he is, you are effectively demanding that he cut a part of his personality away and discard it. How do you cut a part of something away and finish with more than you started? You can’t. Removing a part of who he is will make him less of a man. Plus, he will be removing the parts of his personality that make him kind, compassionate, and empathetic.

Rather, think of him as more than a man. Even though this might sound confusing to begin with, think of him as a man who has a female persona beneath the surface, perhaps well-hidden but has been yearning for a way to be expressed – perhaps for decades. That persona is one that will be able to understand and validate your emotional needs better than other men.

I am not going to be naïve and say that there is no risk when opening any door into your relationship. A very small proportion of crossdressing men ultimately cross a threshold and seek to live full-time as women, committing to surgical procedures that confirm their new gender identity. In these instances, forcing him to live full-time as a male if he is 100% female on the inside will nearly always lead to depressive episodes and increase the likelihood of self-harm.

However, the vast majority of men who crossdress only seek ‘sometimes’ to express a feminine side of themselves, and have been doing so while wracked by guilt, shame, and humiliation because these are feelings that have been suppressed by our Western culture.

I understand that this all feels very unsettling and you may even begin to second-guess your ability to select the right man for you. The truth is that for whatever reason you resonate with the kindness and empathy of the feminine energy that exists within him.

Know that your man loves you deeply. Men like him seek to be better understood, not vilified. Please give them space to be and express who they fully are.

Edith

I stay in shape by trail running. When I am not writing posts to help you be as feminine as you can be, I work as a therapist.

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