10 Best CrossDressing Stories and Examples Explaining “I Love Dressing Like a Woman

10 Best CrossDressing Stories and Examples Explaining “I Love Dressing Like a Woman

10 Best CrossDressing Stories and Examples Explaining “I Love Dressing Like a Woman | Origin of Cross Dressing

Crossdressing is a term used to describe people who express their gender in cu*turally-defined ways that are not stereotypically associated with the sex to which they are assigned at birth. 

In many cases, cross-dressing is related to gender expression, but it can also be about fantasy or sexual arousal. Here we list the 10 best stories and examples of why people love dressing as the opposite sex.

A whole lot of men had always wanted to dress like women for one reason or another, even during the time when cross-dressing was seen as taboo because it was thought to rob men of their manliness.

Origin of Cross Dressing

It’s not often that you hear a group of women screaming, “Why can’t I wear pants?” And yet, in California in 1850, that was just one of the questions raised by pioneer women who were seen wearing trousers. Cross-dressing is so rare among women today that it seems strange to think about it at all. Yet cross-dressing has been around for centuries, and we still don’t know its origin.

One of the first and most popular sources of cross-dressing stories was found in 2009. The blog soon became a platform for real people to share their stories of cross-dressing. Many websites offer advice on what it means to dress like a woman or have tips on how men can try dressing like women without resorting to dragging or fake b*easts. 

Cross-dressing has been around for a long time as well, but there is no consensus about its definition or origin. It’s simply known as “women’s clothing worn by men.” In others, the term “drag” is used when referring to men dressing as women for entertainment purposes. There are also those who believe “cautious clothing crossing” is a better description.

Reasons Why Cross Dressing is in Trend

There are many reasons why men love dressing like women. 

  1. Women are more catered to in society, so it may be a lot easier to express femininity than masculinity.
  2. People who wear the clothes of the opposite sex may also want to tap into their “feminine side.”
  3. There’s no need for elaborate costumes: Any male can wear a dress just by sliding one over his head!
  4. It can feel liberating and empowering when someone is living as the opposite sex, even if it’s just for some time or in interaction with others who know what they’re doing (cross-dressing couples, cross-dressers at parties, etc.).
  5. Cross-dressing is often a fetish and is a way to experience what it’s like to be in the shoes of another gender.
  6. Some men love attention, especially if people don’t recognize them as male or female.
  7. Cross-dressing may also be about sexual arousal, as is the case for many transgendered people.   
  8. Just being able to live as the opposite sex can be an exciting adventure!
  9. Transvestism can also be used therapeutically for some individuals who feel restricted by their birth gender roles or want to work through gender identity issues.
  10. Many people choose to imitate another member of the opposite sex – possibly a celebrity, just because they like their style or the way they dress!

Here is your time to shine for all the women who are over males and acting like one half to their souls. You love feeling all sexy, don’t you? Well, here are 

Undeniable proof that cross-dressing is for everyone

  1. In “The Girl with the Dragon Tattoo” by Stieg Larsson, Lisbeth Salander dons male clothes and cartwheels through Stockholm’s corridors.
  2. Actress Natalie Portman sports her favorite male outfits in her hit movie “Black Swan.” 
  3. Will Ferrell in “Elf”: the funniest man in the world wears women’s clothes. He is sure to make anyone laugh.
  4. Jamie Lee Curtis as a “man” in “True Lies.”
  5. Anne Hathaway as the male Dan in “Get Smart.” She is stunningly transvestite and a witty character for sure!
  6. Tom Hanks does his best to convince himself that he is a woman in this movie, but apparently fails and remains g*y. This is one of my favorite scenes from him in drag 
  7. “Adam, g*y or crossdresser?” This movie is a must-see for any g*y man who has ever been told he is not g*y enough. This scene begins at 1:48 minutes into the clip.
  8. Sean Penn in any movie as a woman, especially “I Am Sam.” 
  9. Posh Spice Victoria Beckham wearing men’s suits has made her a worldwide star! 
  10. Glee: In “The Substitute” episode, Collins dresses up as a woman for a day and is loved.
  11. There is a certain logic in wearing large, feminine shoes while wearing small men’s shoes.
  12. Women have been raised to believe that they’re more valuable and deserving of comfort, so it’s only logical to wear women’s shoes. 
  13. Men have traditionally had the role of provider, protector, and protector of their families, so it may be next to impossible for a man to spend time dressing in women’s clothing.
  14. But then again… It’s interesting that many men enjoy dressing up and doing the “girly thing” (whether out at work or when they’re off from work.
  15. It’s a lot easier to be surrounded by people who are “in the know” and who are more accustomed to seeing men in women’s attire in everyday life when compared with cities like New York or San Francisco.
  16. There may very well be some genuine transgender men who get a thrill from wearing female attire, just as there are transgender women who love their male body and wear only men’s clothing. 
  17. There you have it: Some suggestions for when a man wants to dress like a woman, whether for fun or for some personal reason(s) that may not be easily explained.

You can also find other videos and photos of cross-dressing when on social media. But the top recommendation is to simply check out the stories in which actors or actresses appear in drag. 

The perspective of Cross-Dressing all around the world – Gender Identity Crisis

In some countries such as India, Pakistan, and the Philippines, the word hijra refers to transvestites and eunuchs. In Thailand, it’s known as Kathoey, while in Myanmar it’s called Hijra Phetmey. 

In Brazil, they are often called Bissu while they are referred to as Sworn Virgins in Ethiopia. In some parts of the world, cross dressing takes different forms. 

In some Chinese cultures, men wear women’s clothes as part of their daily lives. For example, in Russia, a man known as the “de-facto king” wore women’s clothes and lived with his wife. 

Men are also known to show up at parties dressed like women. In Thailand, where cross dressing is not allowed in most public spaces such as public transport or hotels, these men are also referred to as kathoey.

The above mentioned terms have sometimes been used interchangeably while others have been used incorrectly. For example, while “drag” is a specific type of cross-dressing that originated in the g*y community, both “drag” and “cross-dressing” are examples of transgender identity. 

However, in some countries and cultures, such as Japan and Korea, where identity is more fluid and society more open than in North America or Europe, it’s not only acceptable but actually encouraged. 

Cross-dressing can become a real way of expressing oneself if you style yourself accordingly while wearing certain clothes. In such a way, one can express the gender they wish to be seen as without meaning to be transgender or hatering those who prefer different gender roles.

Many people dress up in cross-gender outfits as part of everyday fashion trends in modern times. They are not necessarily g*y, but enjoy some of the benefits of being a woman without resorting to burlesque or drag. 

Young people exploring their gender identity may dress like the other sex to understand how it feels to be in that role. In recent years, more and more women are taking an interest in men’s fashion and style; for example, wearing pants suits and bow-ties is no longer so unusual.

The main point is that cross-dressing is not one specific thing; it has many faces depending on the reason, motivation, or personal background of each person who does or doesn’t do it.

The word trans*gender can be used to describe a transvestite or transsexual who has sex reassignment surgery. But it is also an umbrella term which refers to all people who dress in the clothes of the opposite gender.

A study showed that 45% of those with gender dysphoria felt that they had been born into the wrong body, while 39% didn’t feel their genetic sex or biology matched their gender identity.

How Cross Dressing is good for you

Crossdressing is often seen as taboo and may make others uncomfortable. Some people may not approve of it and may make negative remarks regarding the manner a cross-dresser dresses or the reason for their clothing choice.

However, cross-dressing is a way in which one may express themselves without being forced to do so by society or others. Cross dressing can help to boost confidence and may allow them to enjoy the same freedom that others experience but in a sense that they are not normally allowed. A cross-dresser is more likely to feel comfortable with themselves if they dress in clothing that shows off their look and feel for their own gender. Cross-dressing is not harmful, but it helps boost confidence.

In many places across the world, cross dressers are shunned for their dressing. They may not be able to express themselves openly due to the fear of being made fun of by others.

Cross dressing can change a person’s life who wants to feel more like another gender without necessarily meaning to identify as such. Many people do not see cross-dressing as a problem and enjoy that they can express themselves freely while doing so. Crossdressing is not a bad thing and it helps many people feel better about themselves.

Many people enjoy the look of a particular outfit so much that they choose to wear it and have people accept them for being who they are. However, there are also those who may wish to dress as the opposite gender and are not comfortable with the idea that others may make fun of them for doing so.

In recent years, some schools across the world have begun allowing cross-dressing in their uniforms, but this is not something that can be extended to all circumstances. It can become disrespectful when certain individuals do not agree with how certain individuals choose to express themselves. Cross dressing is something that is completely personal and should be respected by all members of society.


Whether you want to do it for fun or to express yourself, cross dressing is not a bad thing and can help many people feel better about themselves. Do not be afraid of trying it out and wearing that dress that you’ve always wanted to wear but were too afraid of what society would think.

The world has many different possibilities and that’s why we should try them all. Maybe cross-dressing is right for you.”.

Cross dressing can change a person’s life who wants to feel more like another gender without necessarily meaning to identify as such. Many people do not see cross-dressing as a problem and enjoy that they can express themselves freely while doing so. Crossdressing is not a bad thing and it helps many people feel better about themselves. 

You deserve to wear whatever makes you happy and you should never be afraid of what other people think. Feel free, express yourself, and have fun. Many people enjoy the look of their own outfits so much that they chose to keep wearing them.