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Why Men Crossdress : 11 Reasons Men Crossdress

11/29/2021

Crossdressing is not a new concept; it means when someone of one gender wears clothing typically associated with the other gender, which has been around for centuries and is still strong today! Men cross-dress daily for many different reasons. Some people are born with gender dysphoria.

 

Crossdressing is often the only way they can feel comfortable in their skin. Other men are attracted to aspects of femininity.

 

Dressing up as another sex will help them explore this side of themselves without feeling judged by society.

 

11 Reasons Men Crossdress

 

Reasons for cross-dressing vary.

 

Some people do it because they enjoy the social aspect, while others want to dress up and do nothing else. Some do it as sexual gratification, while others enjoy crossdressing and keep doing it because they like how it makes them feel.

 

It’s not uncommon for them to feel more confident and prettier. Many men are also attracted to femininity but cannot express their feelings freely. Dressing up as the other sex will help them explore this side of themselves without feeling judged by society or their loved ones.

 

There are some aspects of crossdressing that everyone can agree on. For instance, men must wear cute outfits. One likes seeing someone dressed in frumpy clothing or ill-fitting garments. It’s also necessary for them to pick an attractive wig, if possible!

 

Crossdressing is just one way some men choose to express themselves.

 

In this blog post, we will explore the reasons why men decide to cross-dress!

 

 

1. Reasons Men Crossdress: Fashion

 

11 Reasons Men Crossdress

 

Fashion is a large part of crossdressing for men.

 

It allows them to express themselves.

 

This is an extension of their desire to try on different costumes and roles in daily life.

 

For others, like drag queens or professional performers, it can be a means of earning their living.

 

Most fashion crossdressers do not wish to pass as women.

 

They enjoy dressing in beautiful clothes.

 

Unisex fashions have been a growing trend in the last decade.

 

They allow men to wear clothes once considered “women’s only,” such as skirts.

 

In Japan and South Korea, fashion cross-dressing is famous. Men’s fashions are far more restrictive than women’s in many countries.

 

So, men have much less opportunity to pick clothing not designed for their gender.

 

Clothing designed for women is far more available than clothing designed for men.

 

So, men’s fashions are generally much simpler and less varied than women’s.

 

Thus, cross-dressing allows one to experiment with the other gender’s fashion possibilities.

 

2. Reasons Men Crossdress: Love for the other gender

 

The first reason that many men cross-dress is that they admire women.

 

According to Anne Vitale, Ph.D., “They desire the look, feel, and fragrance of these garments and everything else associated with them.”

 

Some men enjoy dressing in their wife’s or girlfriend’s clothing when she is not around. It adds excitement to their sex life.

 

11 Reasons Men Crossdress

 

Some men even enjoy cross-dressing when their wife is present to see them in women’s clothing.

 

It reinforces the fact that he is doing this for her, making it more acceptable to him.

 

It also makes her more willing to wear sexy lingerie around the house when they are together.

 

For others, crossdressing fulfills their need to feel beautiful.

 

Men are taught that only women are beautiful from a very early age.

 

They strive to be more attractive to attract women.

 

These men enjoy being told they are pretty by their significant other while dressed in female clothing.

 

Pretty and feminine clothing makes them feel more attractive than regular men’s clothing.

 

3. Reasons Men Crossdress: Sexual attraction

 

For some men, cross-dressing is a form of sexual expression.

 

They feel aroused when wearing female clothing.

 

They get a thrill out of achieving an erection while cross-dressing.

 

Some men are not attracted to other men.

 

They are stimulated by the idea of being female in appearance.

 

This is called autogynephilia.

 

Other men are straight or bi-curious but enjoy dressing in women’s clothing for sexual pleasure.

 

11 Reasons Men Crossdress

 

These men are said to have transvestic fetishism.

 

They may masturbate while they are dressed or achieve orgasm by being admired by their partner.

 

Some find the idea of wearing women’s clothing arousing but do not engage in cross-dressing for sexual pleasure.

 

4. Reasons Men Crossdress: For Relaxation

 

Many men find cross-dressing to be a very relaxing activity.

 

It may relieve stress, anxiety, and depression for them.

 

For some men, it is like meditation; they can become completely absorbed in applying makeup or styling their hair.

 

Others enjoy letting go when they are in women’s clothing.

 

They no longer have to worry about responsibility and can relax.

 

Men with demanding jobs or complicated relationships may find it relieving to retreat into their feminine alter-ego.

 

11 Reasons Men Crossdress

 

Being in a supportive and accepting environment is very important for cross-dressing.

 

Any stress or anxiety the man may feel can be alleviated with encouragement from his partner or friends.

 

It gives them an escape from life’s pressures they cannot otherwise achieve.

 

This reason differs from person to person, depending on the stressors of their lives.

 

This relaxation is accomplished in one of two ways: wearing female clothes in public or when home alone dressing up in women’s clothing.

 

Peace can be achieved both at home and in public, but there are different reasons why these methods are employed.

 

11 Reasons Men Crossdress

 

5. Reasons Men Crossdress: Expression of gender identity

 

11 Reasons Men Crossdress

 

Gender Identity is a complex concept for people to come to terms with.

 

In the past, many psychologists believed that all men wanted to be women because of a lack of information about transsexualism.

 

It was assumed that if a boy played with dolls or dressed in his mother’s clothes, he would become homosexual.

 

Yet, many of these boys grew up to be heterosexual men who still crossdress as adults.

 

It is now believed that people who crossdress are expressing their gender identity. Read more about the difference between transgenders and crossdressers>>

 

They see wearing women’s clothing as an opportunity to express themselves in a way society doesn’t usually allow.

 

They still maintain their male identity and gender role outside but get to express their feminine side.

 

6. Reasons Men Crossdress: To hide emotions

 

11 Reasons Men Crossdress

 

Many men who cross-dress do so to hide the fact that they are unhappy and depressed.

 

Society expects men to be masculine, strong individuals who always want to have sex with women and lead exciting lives full of adventure.

 

Men who feel society pressures them into this lifestyle put on a fake smile in public, but the truth is they are not happy.

 

They feel trapped in their male identity, unable to express how they feel because of the fear of society.

 

These men enjoy dressing as women because it breaks them from this lifestyle and allows them to live out fantasies.

 

7. Reasons Men Crossdress: To communicate with other people.

 

Communication is a part of all relationships, and cross-dressing can be a helpful tool for understanding people.

 

Some men indeed crossdress because they’re aroused by femininity.

 

Still, it’s also clear that most want to wear beautiful clothes without sexual motivation.

 

11 Reasons Men Crossdress

 

8. Reasons Men Crossdress: Fantasy or idealization of women/femininity

 

Fantasy or idealization is a big part of crossdressing for some people.

 

It’s a way to explore a different facet of their personality or even the female side.

 

A man might want to wear women’s clothes because he finds them beautiful and feminine.

 

11 Reasons Men Crossdress

 

9. Reasons Men Crossdress: For fun

 

Fun is the most simplistic reason why men crossdress.

 

Some people enjoy dressing up in women’s clothing and have no other reason behind it!

 

Men might also use their female alter ego for different purposes.

 

Perhaps to explore what it would be like to feel more feminine or sexy.

 

Some do so to become an idealized version of themselves without society’s judgment.

 

11 Reasons Men Crossdress

 

10. Reasons Men Crossdress: To fit in

 

Fitting in is one of the most common reasons why men cross-dress.

 

A man might enjoy dressing up as the opposite sex but does not wish to hide it.

 

Some men are content with their biological gender but still want to do female clothing.

 

For these men, wearing women’s clothes in public is a way to challenge the traditional notion.

 

Often, these men dress up and wear clothes in their everyday lives.

 

They may also do this in places where it might be more acceptable to express their femininity.

 

11 Reasons Men Crossdress

 

11. Crossdressing as a stepping stone to ‘transition’ to live as a woman

 

Transitioning to life as a woman has gained some attention.

 

It is due to the publishing of books like “Whipping Girl” and “She’s Not There.”

 

These books argue that many men who cross-dress later go on to become women.

 

Plenty of men do not crossdress before transition.

 

Indeed, plenty are pretty adamant that they never crossdressed at all!

 

It is important to note that most men do not fit this pattern, which is only relevant to a small percentage.

 

11 Reasons Men Crossdress

 

Men who crossdress get many different satisfactions from dressing in women’s clothing.

 

Their motivation also varies.

 

Some crossdress because they feel their female side is beautiful and want to express it.

 

Others do so because it brings them pleasure or relaxation.

 

The reasons vary, but there are many similarities between the men who dress up as women.

 

Crossdressing is a way for men to release their emotions and express themselves.

 

They get satisfaction from the look, feel, and smell of women’s clothes. Many enjoy feeling beautiful, while others are aroused by it.

 

11 Reasons Men Crossdress

 

Related posts:

10 Tips for Beginner to Start Your Crossdressing Journey

Top CrossDressing Movies to Watch in 2023

Crossdressing Tips for Mature Crossdressers

 

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29 comments

  1. Why do I as getting older like crosssdressing and having sex as if I am a real women.

  2. I have a fixation for glossy women’s fashion and beauty magazines, their beautiful soft sweet scented pages arouse me sexually so much that every month I travel to the book stores to hopefully find gorgeous new thick women’s magazines so I can snuggle into their beauty.

  3. I just enjoy swinging with my partner and it allows me to feel like a woman and engage in bi sex without feeling bad.

  4. I love the feeling of silk so dress a lot but to scared to actually meet someone when dressed

  5. HiDavid I hope you are enjoying the way you feel when you’re dressed up and if you’re somewhat looking convincing as a Woman I would try it but not on your own a good friend with you till you get your confidence best wishes for you wish I could do it Deana

  6. Why is it when i crossdress in a skirt pantyhose and heels i want a man to make love to me?

  7. If you are as attracted to men in pantyhose and high heals as I am…it makes me hard thinking about you in maybe some sissy panties.

  8. I’m tall and very slender. The fact that I can pull off women’s skinny jeans and wear them with white ankle boots – and actually look good doing it – makes me see a lot these reasons in my dressing. I love seeing that same look on other women, so it’s sexy to mimic it. It’s definitely sexually arousing. I know I have a very female side in me and like expressing myself this way. I really don’t have a desire to live as a woman, but I like the idea of both men and women finding me attractive when I’m dressed. And of course, I secretly hope one day to have either a man or woman notice that I could pull it off and have them want me to dress up for them.

  9. Been cross dressing on and off for several years.
    My wife has suspected this but the other day actually can home early and found me dressed.she was very upset and has made life very difficult
    What does one due in a situation like mine?

  10. Comment on article,”11 Reasons …”
    Can someone explain to me why a goodlooking gay man who is able to attract other gay men successfully and actually does so, and then, experiences sexual fulfilment with gay men have a need to crossdress to have sex with a man?

  11. 1. Not all woman are beautiful. Why not dress in “frumpy,” ill-fitting garments to represent those women? Why must it be the “cute outfit” only? Drag queens & professional female impersonation performers who earn a living are more
    than justified naturally. It puts bread on the table. Most cross drrssers want to be identified as men, not women.
    “Kinky Boots” scene where the lead actor performs in a nursing home for the elderly and admits he’s a man. Bravo!
    2. In “LOve For the Other Gender’s sexy clothing. Men can buy very sexy men’s clothing which has style at Macy’s, Bloomingdale’s or Men’s Warehouse. The more money spent, the more fashionable the outfits. Then again, an ugly man can always have plastic surgery done on himself.
    3. Sexual attrac tion. How very sad that a man has to wear sexy women’s clothing because he’s unable to get an
    erection wearing his own men’s clothing.His “getting a thrill” is pathetic.
    4, For relaxation. Relaxation in public? There are other means by which a man can escape from depression, stress,
    and anxiety. We all suffer from these yet the rest of us don’t resort to putting on a skirt. Antidepressants are
    available, as well as therapy.
    5. Eventually, this “feeling more confident and appealing” will wear off.
    6. To “put on a fake smile” in public is being a hypocrite. This “fake world of wild adventure” will not last for a lifetime. Such “adventures” are temporary.
    7. To “communicate with other people” everyday? How? By explaining why they crossdress? By better being able to sympathize with those who are depressed?
    8. & 9. For “fun” or for “fantasy” seems understandable enough. Everyone loves a good time!
    10. In order “To fit in.” At a gay function, -yes! Yet, not everyday on the street being flamboyant & flirtatious!
    11. As a stepping stone to gender reassignment. What you mention is probably true. Yet, how can a “mind” be changed? Not by an operation! Some transsexuals want to return to their previous gender before they die.
    ********************************************************************************

  12. I enjoy becoming SophieAnn, wearing female clothes when I can. Unfortunately, like Victor, the woman I love found out and is deeply upset. Feel trapped between a rock and a hard place as I don’t want to lose either of them.

  13. Do guys being a woman for other men to have sex like a girl do they have orgasms like girl’s do ??

  14. It’s nice to break down into a list to try and understand the why of the internal urges. The list isn’t exhaustive and some people may not check any of the list off and others multiple or all of the above.
    I found it useful in a therapeutic, safe way to better understand myself and what burns within.
    It has been raised above in the comments about dressing for sex and specifically dressing for sex with men. We each need to understand our own desires and urges and to accept them. The advice i was given through counselling was to disconnect the dressing and sexuality and to look at each in turn. This may not be the right approach for everyone but i found it helped.
    On this site and other similar sites are safe spaces for use to explore and understand. I would be careful of easy answers as there are none and wary of chat/meet sites as they are used primarily for sexual gratification often at the expense of others. We are vulnerable because of our urges, longings and desires. Equally we are desirable due to our femininity and sexiness.
    I am torn in two by my desire to dress and by my sexuality vs my real life. The world can be cold and cruel and whilst we find like minds and support on line, the reality in the world is we arw viewed as strange and odd.
    Think of telling your friends and family, those closest to you and who care about you about these aspects of yourself and the fear just crushes me. But these are steps we must take as these people are close to us, love us and want the best for us.
    These aspects of me (and like many dressers) are not a choice, how we choose to express them and where/when is. Always be safe and never let the excitement take you into dangerous or risky situations. For sure that can be a turn on too, i know that only too well, but look after yourself.
    On the matter of wives and girlfriends this is what tears me in two. There is part of me that has been held in secret, suppressed that she doesnt know about. There are stories of supportive women and if you have one you are lucky. Most partners are not supportive and imagine rhis important part of you that you’ve kept hidden (not deliberately!), perhaps because you didnt understand or accept it and suddenly dumping that on someone who thought they knew you and loved you. Their world destroyed, their understanding of you in tatters. These decisions are not easy, which is why i say stay safe, if you want to come out make sure it is when you are ready and on your terms. I have no further answer or advice as im in the closet, living a double life. The euphoria of dressing femme against the shame and guilt for the deception of my partner. I have no idea what to do now.
    Love and hugs to you all.
    Monica x

  15. Hi Bobby,
    Some girls do enjoy being the receiving partner in sex with men. I certainly do.
    As for orgasms, that is different. Men have a prostate gland at the base of the penis which can be stimulated through anal penetration. This can be with toys, fingers or during anal sex. The orgasms experienced are often very intense and personally i derive a great deal of pleasure from it.
    There is pleasure from dressing femme, pleasure feom wearing high heels, pleasure from getting male attention and having him lust after me and then the pleasure from anal sex. So all these different feelings of pleasure combine for a very, very intense and pleasurable orgasm for me personally.
    Sometimes through pure excitement i orgasm from the initial penetration.
    I hope this answers you question.
    Monica x

  16. I not only prefer been dressed as woman, but I thoroughly enjoy been a “woman” for men aswell, I found I liked crossdressing when I was about 16, several years later I was caught dressed by someone I know, he said if I like been dressed as a woman, I must like men & soon I was on my knees giving him a BJ. what I’m trying to say is the world is full of people who have different needs. I must admit though been stripped to my lingerie & high heels looking after a man’s needs for the 1st was rather scary & exciting but it made me be the woman I want to be.

  17. Yes I love the feel of being dressed up it’s so good to feel silky clothes next to my skin and tight things on your body and I heels that you can walk in. Give you that feeling love the way someone put their hand on your leg and touch you and make you feel wonderful

  18. It is a very difficult thing to accept in your Husband. As a woman it makes you feel like you are not enough for Him. Like there is something wrong with You. I was devastated when I learned that my Husband of well over 30 years was dressing up like a woman for a guy who was younger than our Son. I couldn’t deal with it even after going to numerous counselors. My advice to men who enjoy this don’t marry.

  19. The number of reasons are as different as there are men doing it.

    I can feel sexual arousal without it. I don’t need it in my life to feel fulfillment, what I need is the type of validation of being wanted sexually -feeling irresistible…. In drag I can feel that way and even if you look look like a linebacker with a wig on, that would actually send people running what I FEEL is the feminine power of being sexually desirable at all times.

    For me the internal feeling while dressed in full drag in the moment is affirming…I am hot, I am desirable, people are vying for my attention. I am what I wish I was as a male the source of strong sexual desire. There are people desperate for my attention, I can arouse people sexually with ease and fulfill their desires. At any time I please to be sexual I can get what I want… all that has an appeal that isn’t as direct a connection to gender preference as one might think. it feels good to be that desirable…

    I created a woman who was always around to play with me in a sexual manner that couldn’t resist me. It is less a compulsion and more an escape for me being myself. An easy way to manufacture excitement. It If I was with a woman whose libido and sense of adventure matched mine I wouldn’t have a need for it.

    That type of spouse can take a lifetime and never be found, and there are other things more important to balance in a partner. The idea of kissing a guy repulses me, but in that mode roleplaying it to the fullest provides the excitement that may is missing as yourself. While engaged in transvestism that sexual validation is easier to achieve because guys are so much hornier and separate sex and emotional connection so much more than woman. Its an easy escape.

    The desire is not to express a feminine side of me, to have sex with a male, but to feel desired, to be able to be sexual at will. To be alluring and wanted. That is why some men in marriages still turn to it. I wonder how many guys who are having sex all the time with their spouses, have sex that doesnt feel like routine service sex still feel it as a compulsion.

    I

  20. I found out at birth that my mother dressed me in my sister baby cloths for 2 years back in the 60s,other mothers would say what a pretty girl, then his sister would dress her up as their baby sister in his younger years in dressers and lip stick.
    Dressing up has stayed with me all my life, before the internet I was a lone wondering should I have been born a girl. Knowing now cross dressing is normal feeling to have, there is a lot of us males out there I do not question it feels natural have the best of both worlds. so what very feeling and style just enjoy it, as they say if you can not beat them join them, makes sleeping at night easier then trying to analyses those feminine urges.

  21. I started crossdressing a few years ago My wife packed my clothes bag for the week for me I found a pair of her panties in there I called home that night and asked what should I do with them She said wear them to bed and jerk off in them I did ever night Came home with cum strained panties and she asked how I liked wearing them I told her the truth I loved wearing them Needless to say I found another pair therenext week She started giving me some of her old outfits and she got me stuff for Christmas When we go off on holidays we always going shopping for new stuff for both of us One store the sales lady figured out she was buying for me She told the wife I would look good in that outfit It has opened a new world for me Wife likes it and I have been checking out dating sites for CDs with the wife’s permission She likes that I crossdress and I am comfortable with Her dream to do a 3 way with another cd and me I am in !!

  22. Thank you for this forum. I’ve been enjoying reading the comments. I’m a wife but my husband can’t explain his desire to dress like a woman. Zero lesbian tendencies on my part! But for him I wear a strap on and let him play with “my dick”. He says he wants to feel cum shoot down his throat, wants me to teach him how to “ride like girl”, and I just get quiet. We’ve been together 20 years and it feels like he’s brought “another woman” into the relationship. I don’t get it. Can’t figure out why he’d rather go on a a “girls trip” and stay in drag the entire time. When asked by strangers he wants to say we’re girl friends instead of husband and wife. He wears boobs, bra, and panties ALL THE TIME at home. I’m not aroused by him in a feminine appearance at all and never initiate or encourage sex. He says he’s not gay and not attracted to other men, but then he says he wants “people” to see him as a beautiful sexy woman. He still works, but I’m concerned he’ll go full female once he retires. He says he won’t, but maybe that’s just to get me to stay? Can’t figure out why he wants to be married to a woman of he wants to pass for one. He doesn’t like other CDs because he thinks they don’t pass in large groups. I question why I stay everyday.

    1. It sounds like you are going through a difficult and confusing time in your relationship. It’s important to understand that your husband’s desire to cross-dress and explore his feminine side is a part of who he is, and it’s not something that he can simply turn off or ignore. It’s also important to understand that this doesn’t necessarily mean that he is gay or wants to transition to being a woman.

      It’s understandable that you may feel like your husband is bringing another person into your relationship, but it’s important to remember that this is still the same person you fell in love with 20 years ago. His desire to cross-dress doesn’t change the fact that he loves you and wants to be with you.

      Communication is key in any relationship, and it’s important that you and your husband are able to have open and honest conversations about your feelings and concerns. It’s possible that you may never fully understand why he wants to dress like a woman, but it’s important to try to be accepting and supportive of him.

      It’s also important to set boundaries and have a conversation about what is and isn’t comfortable for you in the bedroom. It’s okay to not be aroused by your husband in a feminine appearance, and it’s important to communicate that to him.

      Suppose you are feeling overwhelmed or unsure about your relationship. In that case, it may be helpful to seek the support of a therapist who can help you navigate these complex emotions and provide you with tools to communicate effectively with your husband.

  23. I do agree that communication is very important I have been crossdressing most of my life my sister asked me to wear her panties we were 12 and 13 years old I have been hooked on girly things ever cents I told my wife before we married she was ok it’s been a struggle at times she now love’s for me to wear leggings in public not fully dressed you have to pick your battles I still will get fully dressed make up everything when I can but my wife doesn’t want to see me in full feminine so just talking and compromising works well for us

  24. Telling these wives who found out about a hidden life to “just accept it and support it” is not understanding the human condition at all. If you can’t see both sides of this issue then maybe don’t comment. I have a trans son who I love and support and buy both girls and boys clothes and makeup for… it’s expensive. However I met a man 6 months ago who was all things that I loved. He was in a motorcycle club, mountain bikes, loves the outdoors, had a sexy beard. One night after leaving my house after the weekend came bursting out of the closet via text. He told me that he loves crossdressing and went on to be very explicit about how much he loves di@ks and cum and how he wants 10 men to run a train on him. Eventually he asked if I would go with him dressed to a gay bar and watch him pick up a guy. I was floored. Because of being raised to accept everyone for who they are I stayed with him for a few more weeks and had all of my boundaries trampled. I’m sorry, if someone lies to you about who they are you should not stay with them. I don’t care what the reasons are. If they are lying to you every day about one thing they could be lying to you every day about multiple things. If you crossdress then you should be honest very early. If you can’t, then don’t get into a relationship. I was dehumanized, and I am the biggest supporter of lgbtq+ rights. My mother is gay, my brother is gay, and my son is trans and this was the biggest insult to the honest lives these people live and the rights they fight to maintain.

  25. I too can only achieve an erection when I crossdress in undergarments. Now that I’m older and married with no kids, I don’t have a sex drive anymore.
    It scares me of losing my wife. She knows about my crossdressing but doesn’t care of see me dressed when she’s around. She says she accepts it but it doesn’t seem like it. Sometimes I wish I could turn off my urges.

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