Why Do I Cross-Dress?

By Randi Klein

August 14th, 2020

Insights and Comments from 12 Cross-dressers

Many men who cross dress are not even sure why they do. Although the feelings are strong and compelling, the reason or the catalyst as to the “why” is elusive. Most are not able to articulate much beyond some vague compelling feeling. “It just feels good” or “I feel like the real me while cross-dressing” are the most common reasons given to family and friends as to why a person would pursue this expression. However, there is a concrete and knowable reality behind the need for genetic males to express the feminine through cross-dressing, even if they themselves are not aware of it. They range from curiosity and sexual stimulation, to gender identity and even, in rare cases, mental illness. Some explore the opposite gender as a way to connect with suppressed emotions. Others use cross-dressing (CDing) to experience a different life-perspective. The one thing most all cross-dressers have in common is that the need is neither frivolous, nor easily dismissed.

To help understand the mind-set of a cross-dresser, I have solicited the thoughts of twelve people who identify as transgender. None of those surveyed deal with serious mental illness. All those participating would be considered fairly mainstream. All live the bulk of their day as male, or what is referred to as “in male-mode.” Most of their friends and family members are unaware of their need to cross dress. In other words, they would appear to most in society as “normal, upstanding male citizens.” All identify as Christian, and most are either leaders or active members in their perspective churches.

Those who provided comments share a few things in common:

1. They all questioned the act of CDing as to its morality in light of cultural and scriptural concerns.

2. They all tried in earnest to fight or shutdown their feelings and stop CDing at one time or another.

3. They have all struggled with this since a young age (before the age of 8 years) and have never been able to free themselves from their CDing needs, desires or thoughts.

4. They all sought some form of either professional counseling, or reparative therapy. The result or which was an increased understanding of the subject, but not a relief from its hold.

5. They all experienced, through acceptance of their transgender condition, a certain amount of peace and relief from guilt. Their feminine expression ranges from a total embrace of CDing, to a limited occasional activity.

6. Even after decades, the feelings for most are stronger now than in their youth, and the issue of desiring to express the feminine is very active. Some identify fully as female, while others would place themselves along some point on the gender spectrum. They range in age from 40-85 years.

Below are quotes from 12 different cross-dressers. They offer a range of thoughts and experiences:

Quotes from Mark S. “Mary”

“When cross-dressed, I became wrought with shame in my teenage years, but now working through this struggle, it has become a badge of courage. As a productive senior citizen, I tend now to follow my heart and am not afraid, like I used to be, to enter areas that are labeled “Do Not Enter” by my local community. Dealing with this condition has given me courage.”

“Who do I hurt by cross-dressing? I definitely hurt the feelings of those of my family who fear the repercussions from some in my local community if they ever found out. It seems to me that I mostly offend the person who fears that they may be transgender or even gay themselves.”

“By my cross-dressing I seek not to endanger any person. I seek only to discover more of myself and to create a safe environment to experiment in.”

Quotes from James M. “Natalie”

“When I dress as a woman I am expressing the maternal softness and vulnerability that I find within myself (softness that I usually conceal and am embarrassed of). I cross-dressed, instinctively in my youth and then purposely in my senior years, to form a more perfect union of all that is me.”

“I know the peace of God and I know it well and I have been privileged to experience his supernatural calmness and encouragement often. The thing is, I have never experienced His peace when I have been cross-dressed or even when contemplating doing it.”

Quotes from Robert S. “Jennifer”

“I do not believe God leads me to cross dress or that He made me transgender. In other words, the reason He never speaks to me about CDing may be that He isn’t leading me to do it. Having said that, however, I must quickly confess that a part of me greatly enjoys cross-dressing and exploring life as a woman. God does not condone or condemn my CDing in its entirety. There are many aspects to my CDing. These can be both good and bad — both hurtful and healthy. God did not preordain my transgender nature, but he did allow for it, and so is able to redeem it. God did not ordain my gender confusion or the rigid social gender roles I have to contend with. He has used my CDing though, as an opportunity to teach me.”

“Perhaps I do not have the peace I seek for, because God does not intend for me to stop my exploration yet. He has more for me to learn. Perhaps cross-dressing is not intended to give me peace, but instead to spur me on towards discovery, and hopefully a healthy self-image?”

“Maybe CDing has caused me to throw myself at the Lord more than I otherwise would have.”

Quotes from Bob M. “Still deciding on female persona”

“It’s a complicated issue and the most troubling of any in my life. I have told the Lord many times that it won’t change unless He does something about it, for apparently I am unwilling or unable to do much about it on my own. Why is that? I don’t know but that is the question I’m dealing with and prayerfully I will get somewhere with it. I now rely on God to change my heart and desires as he sees fit. Not in a passive way, but in a guilt-free expectant way.”

“I want to ask myself, ‘Is being a cross-dresser and all of the thoughts, feelings and attitudes I have, made me more like the person I would like to be or less?’ The answer is a resounding “no.” No, I do not like being a person with what is, to some extent, a secret life and to be so absorbed in that. I do not like the constant secrecy, lying and battling that goes on with all of this — it is not good to live a lie or a double life. However, I suppose I play many different roles daily as I find the need. Obviously, my cross-dressing is a big role change, more so than most. However, I also have my church face, my game face, my husband face, my son face, my dad face, and my private face. These may look somewhat the same, but there are still differences. Each face I wear has an exposed side and another I choose to hide. Perhaps this is a lie, perhaps not. I think I can get frustrated and falter if my secrecy leads to guilt. When I hide too much of who I am, my relationships are jeopardized.”

“Why would anyone choose to go against society, religion, biology, and psychology to live even momentarily as something they’re obviously not, if there was not a compelling reason to do so? It requires such an enormous suspension of reality for me to do this. Only a strong motivation like sexual pleasure could cause my behavior. So, is this just sexual? I went to sex addicts anonymous, and tried to work through their “12” steps. I realized that this was not it. I liked sex as much as anyone else, maybe more than some, but I don’t need to dress like a woman to find sexual pleasure.”

“Five years of counseling and reparative therapy turned up nothing. I tried, yes, I even hoped and prayed I could find something to point to and thus find healing from cross-dressing. I tried to blame mom and dad for some repressed childhood trauma, but found nothing there either. Mom and Dad weren’t perfect, but they were about as normal for post-WWII parents as you could imagine. I’ve since met with many other men who struggled with various adult addictions and these guys had some really bad parenting, yet not one was interested in cross-dressing. The childhood abuse or trauma argument just did not apply to me.”

Quotes from Dave J. “Kathy”

“I cross-dressed and then went back to “normal. ” I envied women (their beauty and appeal) but I didn’t idolize them. Becoming a complete-woman was not my goal. CDing is only an occasional crutch to deal with pain and stress.”

“Considering my people pleasing personality, my need to CD must be something very strong to make me risk the wrath and ridicule of family, friends, and society in general. It was more than curiosity and relaxation. I welcomed the relief at finally being real and honest. CDing is not a desperate attempt to escape reality. It feels right and comfortable. I feel real.”

Quotes from Norm P. “Diane”

“Was I a closeted homosexual? I gave it my best shot, but just could not find any desire for men of any type. In fact, physical closeness to men repulses me.”

“It’s as if my brain is somehow hard-wired to be a woman in spite of my chromosomes and genitalia, in spite of being raised as a boy, in spite of being successful as a man, husband, father, and grandfather. Whatever makes someone feel like a man or woman must exist in the brain and not just the organs and hormones. This was the only way I could explain my desires and thoughts.”

Quotes from Eric R. “Silome”

“My exploration of being transgender has led me to conclude that I was fearfully and wondrously made by God; He knit me together in my mother’s womb; He made me the way I am for His glory and to enjoy Him forever. Years of constant daily prayer for the truth have given me no other answer. Realizing I am who I am, transgender, has given me much comfort.”

“It was only after I became aware of other trans-persons, that I stopped to examine my life and began to recognize a pattern of behavior that indicated an unusual comfort with the feminine role. As I embraced this just a little, it opened up a flood of emotions I never expected or sought. It was like being honest and real for the first time in my life. So why not embrace this and transition to living as a woman? The cost of that is high by all accounts, very high. I’m not willing to pay that price. I don’t want to give up my family and friends and I feel I would have to. I’m not even sure I would want to live full time as a woman if I could. I’m also comfortable living as a man; whether this is due to long practice or the wiring of my brain, I’m not sure. I suspect the latter, though. I envision gender as a continuum and I’m somewhere very near the mid point of it.”

Quotes from Margie

“Whenever possible, I present as a woman as completely as a 6 foot 2 inch frame allows. I don’t sense I’m acting or putting on so much as I’m allowing myself to be and express what has been long suppressed. Life is not perfect, but it is good.”

“I do not consider ‘it’ cross-dressing. I don’t feel women’s clothing is not the opposite gender for me, but my normal way of dressing.”

“I certainly have emotional needs, but I am an engineer with a master’s degree and am a scientist at heart, so I need to understand the clinical side of this as well. This should go a long way to dispelling much of the “out of hand” dismissal of my ultraconservative church background. I am only recently out to my wife of 40 years and she is struggling with this mightily. I don’t see myself as ever transitioning but being TG is an undeniable part of me that needs to be recognized and accommodated. My two selves are very separate and I have no immediate plans to share this information with my current church. They would not necessarily be judgmental, it’s just that I don’t want to go through all of that if I don’t have to.”

Quotes from Mark M. “Sheri”

“This morning, in a very clear way, while I was cross-dressing the Lord imparted to me the gift of no condemnation. For the first time ever, I have the peace of God while cross-dressed. This is a very big deal.”

“I worry about people finding out. I don’t know what they would think. If I were to ask any number of people in my office, for example, what they think of Christians I suspect I’d hear adjectives used like narrow-minded, hypocritical, homophobic, misogynistic and intolerant. In my experience at least, those adjectives don’t really fit the Christians I know. It isn’t who I am as a Christian. In like, I don’t think I would fit their image of what a cross-dresser is either.”

Quotes from Marvin R. “Janet”

“In high school I was class president, dated the homecoming queen and played football. I’m a college graduate, and I’ve always had good jobs. I’ve made a lot of money and have a great family. I’ve been in many small men’s groups at church and have facilitated many too and I have to say I have far less insecurities than most men I know. So it actually still freaks me out to some degree that I want to shave myself and become Janet.“

“Maybe I want to cross dress because it feels safe. When I’m dressed in female attire I feel completely honest. I like how I feel when I’m female…but honestly, I don’t dislike how I feel as a guy. I’ve never suffered from a feeling of loathing of being a man…although I’ve never been comfortable with some stereotypical guy stuff either. Cross-dressing represents a REAL vacation to me. An opportunity to shed the burdens inherent in my life and temporarily become a softer, more overtly loving version of myself. I often have marveled at how much closer I tend to feel to God while CDing.”

“How did I get this way? My parents, God love them, were so hilariously hyper vigilant about gender roles and behavior that almost anything but anger and exaltation were labeled “feminine.” If I cried it was “girlish.” If I expressed tenderness demonstratively or wanted to learn to cook I was acting girly, and that was a bad thing. Cross-dressing became the method I used to reclaim that which God wanted to originally give me.”

Quotes from Joeseph C. “Lori”

“I’m finally learning to accept that this is my “thorn in the flesh”…and that that’s OK. I actually find myself looking forward to my future!”

“Having spent 45 years in the evangelical church, I have always been under the bondage that what I am doing will send me to hell. Now, in recent months I have stopped fighting who I am. I have even begun praying as Lori, and was shocked to feel totally at peace with that. It is hard to accept that after a lifetime of my femininity being sin to me that I can still communicate with God while expressing my feminine side. I’m afraid though that if my family learns of this they will think that I am headed for hell. I know what people say about being surprised at who accepts you, and a Gender Therapist I consulted suggested that two of my children might understand. However, I am not sure since I see how negative they are towards the homosexuals in our family. I really want to socialize as Lori. I keep telling myself that if Lori must go away for my family’s sake, that I want to at least have socialized as Lori a few times. I plan to find a support group.”

Quotes from Steve P. “Carol”

“I asked myself why I wanted to go out as a woman. Searching my heart for an answer, I found it was simply what I wanted to do. My guy side can’t understand this need, but the fem part laughs and says, ‘What else did you expect?’ So here I am, so unsure, searching for truth from God and myself, while all along walking on a road that I walk involuntarily.”

“This road has been difficult, but the growth, life lessons, self-acceptance, peace, grace, and physical health I have received through acceptance is very much a redemptive act. God did not “heal” me of what I thought was an affliction, but instead used it in a redemptive way. He redeemed who I am, rather than change me into someone else.”

“It is hard to attach blame on someone else for my CDing. I don’t think it was any one thing that makes me want to cross dress. All I know is that when I stopped struggling and began to accept myself, the desire to dress became manageable. Accepting my needs, freed me from guilt”

“My wife has been very understanding of my need to express the feminine side of me, and both of us know when I need a break from my “male” life. This is all still new to me, but I think I am beginning to understand why I feel the way I do. I’m glad I have someone to share this gender identity issue with who is not judgmental.”

Why We Cross Dress – A list of Reasons and Catalysts

1. Child abuse (emotional and physical)
Both physical and emotional abuse, especially from a trusted adult, are destructive actions that victimizes the child. Abuse leaves lasting marks which if not addressed, can affect the quality of life for the survivor well into adulthood. The act of abuse often leaves the victim feeling out-of-control. Cross-dressing can be a way to cope with the emotional pain of past child abuse. It can be a way to attempt to regain control. The endorphins released during cross-dressing and the comfort of the clothing can help to relax and center and can be used as a type of therapy, or self-medication in some cases. Someone who is abused may turn to cross-dressing for comfort, but cross-dressing is rarely the direct result or response to abuse. Rather, a more purely fetish behavior will often be embraced by the victim of abuse. Usually a specific object or objects are fixated on that represent the actions of the abuser. This fetish component could be incorporated into a person’s cross-dressing, but only a trained therapist with knowledge of both abuse and gender identity can sort this out.

2. Gender-related Taunting
Although not as prevalent with today’s youth, many boys have been victims of gender taunting. Some boys identify more with girls and feel more comfortable around their female peers. When a boy demonstrates female tendencies, expressions or interests, he might become a victim of taunting. If ostracized by his male peers, this disassociation with the male gender could become a catalyst for a boy to experiment with cross-dressing. He may develop a close association and connection with his female image. The person who is the object of persistent gender-related taunting almost always has demonstrated those feminine characteristics being cited by his peers. Taunting may drive a boy to choose the female over the male, but that desire to be female usually already exists.

Not all boys turn-away from their taunting male peers. A boy, who wishes to fit in, may succumb to the taunting and deny himself those feminine interests cited by his peers, or try and cease his feminine expressions or change his mannerisms. This will almost always result in emotional damage, and a poor self-image.

3. Emotional Gender Identity
There is a distinctive difference between the typical male and female brains. Some biological males are born with what is considered a more typically “female brain” as evidenced by emotional responses and self-declared interests. Many cross-dressers consider this condition as their most important reason to express oneself in female mode. Powerful emotions while cross-dressed come to the surface of even the most placid male. These feelings can preoccupy much of the cross-dressers day, even when they are in male mode. The reason for this may be biological or sociological. Both are valid, real, and need to be recognized.

4. Biologically Pseudo-female or Androgynous Body Type
There is a wide gender spectrum of body types, emotions and interests. Many who cross dress are expressing not only how they feel mentally, but are responding to what their body is telling them physically. Some males have body types that could be confused for female. Wide hips, enlarged chests or breast, and small hands to name a few. Some males simply do not feel comfortable in male clothing; it really does not fit them. They may have a healthy self-image and truly feel more comfortable expressing themselves as female or softer in appearance. Often these males will adopt a more androgynous look. Some may even consider themselves as “inter-sexed” even though the sexual organs may not be ambiguous.

5. Psychological Female Gender Identity
This is often the most common reason for a male to dress as a female. Regardless of the catalyst, someone who has chosen cross-dressing to express an inner need will usually have a psychological profile showing that they have a strong alignment to female sensitivities or typically female thought patterns. Most males in our society have very rigid ideas about what is and is not allowed for a male to express. These males while cross-dressed, give themselves permission to embrace their inherent female psychological make up and express those feelings they deny themselves in male mode. Often, our sociological training is such that many males find it next to impossible to express these emotions and thoughts unless they are cross-dressed.

6. Social Gender Identity
A male may cross dress as a woman to join in social activities that interest “her” which “he” has previously suppressed or avoided because of social gender roles. The desire to experience social situations as female will often lead a cross-dresser to join social groups. Activities and social settings include dining out, shopping, playing sports, or just taking long walks. Sometimes a cross-dresser will want to partake in other typically female roles while “dressed” including, cleaning the home, cooking and gardening.

7. Fetish
Some use cross-dressing as a tool to express fetish behavior. This however usually includes some sort of object for sexual stimulation that is not inherently related to sexual function. Most fetish behavior focuses on a specific aspect of clothing such as shoes. Also role playing, wearing seductive costumes, or dressing in tightly constricting clothing can be a fetish expression of sorts. But not all these have a clinical of psychological root in fetish behavior, and the person may just be cross-dressing for fun or curiosity. A true fetish behavior is often a result of childhood trauma.

8. Depression
Although not a reason to cross dress, it can be a catalyst. The act of cross-dressing can release endorphins that are shown to help battle depression. Although these endorphins can sometimes become addictive, much like someone who is a runner or jogger becomes addicted to the runners high, cross-dressing can be an effective tool for self-medication.

9. Chronic Depression
Much like regular momentary depression, the endorphin rush experienced through cross-dressing can ease the symptoms of chronic depression. However, the effects are very short term and not as profound. Chronic depression is much more severe, and only an aggressive treatment program including therapy and chemical aids can offer real effective chronic depression management.

10. Fun/Entertainment
For some cross-dressing is just a costume and used as play. These males still relate strongly to their male role but just wish to express an aspect of the feminine, or mimic women for a short time.

11. Curiosity or Envy
People are normally very curious. Some males want to see what it would be like to be in the role of a woman. If this is the main reason to cross dress the act of cross-dressing is usually short lived. Envy is included in this category because both do not have a long-term, biological, sociological or psychological component. A cross-dresser may say that they envy or idolize a woman’s body, but this, by itself is not a compelling reason to cross dress.

12. Relieve Stress
Some feel extreme pressure in their everyday or “male” lives. The act of wearing women’s clothes allows a male to take a break from their social masculine expectations, restrictions or pressures. Cross-dressing for these males is escapism.

13. Poor Male Self-Image/Acceptance
Some males wish to escape their male image because of a negative or poor self-image. Although most were well adjusted when toddlers or even young boys, they become increasingly disassociated or disconnected from their male persona and male peers as they age. Those boys who are not gender-polarized towards the male end of the spectrum may find it hard to fit in with other boys. This lack of acceptance can lead to the development of a poor self-image. They often feel as if they have no real male friends and will gravitate toward a female expression in hopes for some peer and self-acceptance. An affirming transgender community is often the only community they may feel comfortable with. Although not a reason to begin cross-dressing, it is a compelling one to continue. Affirmation of their feminine image by others can even help improve a negative male self-image. Being affirmed as a person helps a negative self-image.

14. Andropause / Mid-life Crisis
When a man (usually between the ages of 35 and 60) goes through the change of life, it is called andropause. At this time, testosterone levels decrease while the estrogen percentage increases. He becomes less aggressive and more gender neutral or softer in his actions and interests. This happens to all males to varying degrees. If he has previously demonstrated a desire or a proclivity to cross-dress, the hormonal changes during andropause can be a catalyst to begin cross-dressing again in earnest. This is sometimes referred to as mid-life crisis. Who am I? What have I done with my life? Is this the life that I want? These questions come out of a sense that time is running out, but are heightened by a change in the body’s chemistry. A drop in testosterone may make a male feel more feminine, and re-ignite a desire to look and act more female.

15. Sexual Expression
We are sexual beings, and the act of cross-dressing can release powerful sexual emotions, making it easier for some men to connect with their feelings. Sexual orientation usually is unaffected.

16. Schizophrenia / Mental Illness
Decades ago, the diagnosis for being transsexual of transgender was mental disorder. Schizophrenia was the most common diagnosis, since the person who was male was declaring himself to be female. This was mistakenly interpreted as having two personalities. This condition was considered a serious illness needing therapy, including shock therapy. However, this was almost always a misdiagnosis in that a transgender person is aware of their choice, and has purposed to pursue it in order to develop congruent personhood. Fortunately, the medical community today sees the “schizophrenia” diagnosis as unsubstantiated in all but some very rare cases. However, with many cross-dressers, the alternative “female” personality is a distinctly different persona from their male. “She” frequently has “her” own name and social niche. Rather than being a mental disorder, this double-life is often a matter of convenience for associating with other cross-dressers. For some this alternative personality could even have “a life of her own.” This is not, however, a split personality because the cross-dresser knows that the “female” character is in addition to their male persona, and is aware of the distinction. An individual with true schizophrenia or a mental disorder has a break with the reality of their situation and could have more than two personas. This individual needs clinical help for their condition.

17.Inter-sexed or Hermaphrodite
Some people are born inter-sexed and their choice or clothing or gender expression can confuse others as to how they wish to be related to since their gender is non-specific. Their choice of clothing should never be considered cross-dressing, but just a declaration of personhood. Often their clothing choice is gender non-specific as well.

18. Personal Choice/Drag
Some call their cross-dressing a hobby that occupies their leisure time. They have no real underlying psychological reason to cross dress. They dress in women’s clothes purely as a creative or fun outlet. “I just feel like it” is reason enough for them. A male who dresses in drag to entertain does not usually identify as a cross-dresser or transgender in terms of their gender identity, but refer to themselves as female impersonators, or drag queens.

19. Cross-gender Predisposition
All those who identify as transgender and use cross-dressing to connect with their transgender nature have some sort of predisposition to do so. Whether it is nurture, nature or choice, the desire to be female full-time, or in part, is a predisposition. This is not a fully conscious or personal choice on their part, but goes deep into the core of how they relate to their world.

This list is not all-inclusive but touches on many of the reasons why a male may want to look like and be treated as female. Those who cross dress when younger, will often stop when they become teenagers. The natural female tendencies, however, will remain, and the person can develop severe anger, depression or even thoughts of self-injury when suppressing their female desires and emotions. Often, it isn’t until later in life that these transgender individuals seriously address their gender issues. Often, it is a back and forth struggle of indulgence and purging. It is important to look at the issues of mental, emotional and physical health over the idea of right and wrong. Cross-dressing can be good therapy.