I would agree with Tricia to a great extent… Why do I cross-dress…

1. I feel really excited when I cross-dress… specially a full transformation
2. I do it partially for sexual gratification
3. I feel very powerful sexually when dressed as a woman. I like the way people look at me in admiration, when i dress up a bit sexy, the way the heads turn, the attention I get. No matter what I wear as a man, I never get that kind of attention/appreciation
4. I feel it is very artistic. Its not as simple as picking up a pair of clothes then wear them and I am ready. For me its is very artistic… I chose a dress/clothes to wear, the lingerie I would wear with that, then the makeup and accessories…!!! Finally when the full image emerges, I find it very satisfying… at times, I do not like what I see and I change or start over.
5. I have a huge attraction for women High Heels shoes/boots/sandals, etc. I have always found them to be very sexy. I cant wear them when I am dressed as a man….
6. I love the feel of lingerie on my skin. The fabric, the cut, shape and fit…!!! I love everything about it. The way it hugs my body… it feels so good… I have been wearing lingerie for over 30 years… panties, stockings are the regular ones even when I go to work as a man. At times, I even wear bustier/bodysuit, panties, stockings, etc. and I feel very excited about it.
7. I am NOT gay…!! I do not look for men when dressed up. But I like to see and meet more women and I find it interesting when they react to my voice… they look confused initially, then despised, then appreciative…!!! Its a wonderful thing to observe such reactions about the same thing from the same person
8. I find Lesbian sex very exciting… I always thought of experiencing myself when two women make love. I try to experience that..!!! It is very satisfying too.

When Tricia says, the power of Women sexuality, I could not agree with her more. Men drool and bend over sexy women and whatever they do, most of it is to win that sexy woman… or get that sexy woman. This is one thing that some women know the best while most women are completely ignorant about.

I am going to tell you why I believe men cross dress. There are women that cross dress too. I think it is for similar reasons. You may not agree and that is your prerogative. Would likely be better to hear from male cross dressers. I have only had two clients that were cross dressers in the 30 years. I believe there were more. They simply did not tell me. Here goes:

One common reason that men choose to cross dress, is for sexual gratification. They may enjoy the sexual excitement that they experience from wearing feminine clothing, and in seeing their feminine image.

Another reason for cross dressing, is that men want to feel free to express the feminine side of their personality. Boys are commonly socialized to believe that they cannot portray feminine traits. They can't cry, appear weak, or be soft. Males who dress in female clothing often feel liberated to express their emotions that perhaps, they are not able to freely express as themselves. Men do not like their responsibilities. They find them burdensome. They don’t know how to relieve themselves in another way so they cross dress.

Many men want to feel the "power of a woman." They want to turn heads too.

Women often do not know just how powerful they are. Women are very powerful especially sexually. Especially sexually. It is too bad no women have ever written a book directed to women on how to use their sexual power. It is sad that women are unwilling to share this secret they know.

Unfortunately, in many societies cross dressing, especially male to female, is often still considered an illness or that they are gay. Many men cross dress that are not gay. And so what if they are gay as long as they are not hurting their wife and kids or any one else.

I forgot to mention one of the most important ones. They were women in a previous life or maybe all of their previous lives and came as man this time because they chose to do so.

I’ve posted on this many times. “Cross dressing” is a general term, and there are several different types of people that cross-dress. Motivation is quite different.

Transgender folks are dressing to match their perceived gender. They usually do not think of this as “cross dressing”. A M-to-F transgender identifies as female, and as such is wearing the proper clothing.

Likewise with F-to-M transgender folks.

Transvestites are different. Note that this is the clinical term for someone with the paraphilia of transvestism. (The term transvestite seems to be felt to be somewhat pejorative by some, so they use the term cross-dresser. Transvestite is the correct term.)

Transvestites are heterosexual men who wear women’s clothing because it turns them on. Again, it’s a paraphilia. Because of the problems with misunderstanding, shame, embarrassment, etc. associated with this, many transvestites will deny the sexual component. They will say they cross-dress to “relax”, or to “express their feminine nature” or a variety of other things as the other answers indicate.

Nonetheless, it is a well-understood condition and the primary motivation is sexual. Most transvestites are attracted to specific types of clothing or specific outfits, often items that were popular when they arrived at puberty.

Some homosexuals cross dress as well, they “do drag” (think of RuPaul). This is for entertainment purposes and has been a part of “gay culture” for a long time. There are drag shows, competitions, etc. by most accounts, there is no sexual component to this; gay guys are not “turned on” by cross-dressing. (Note that there is also a “drag king” scene as well where women dress up like male celebrities and entertainers)

There are a couple of other aspects as well. Folks who identify as “androgynous” or “intersex” may wear clothing items of either sex to affect a “neither this nor that” appearance.

Also, there is a “cross-play” scene… Doing opposite-sex cosplay at festivals and cons.

Okay, here’s the thing. I cross dress, but it’s not an every day thing. I cross-play, which means that I cosplay characters of a different gender than me. Why do I do it? Because it’s fun. I like dressing up as my favorite characters and it’s always really fun to see people’s reaction to it. I’m not a guy, but most of my favorite characters are male. It’s really amazing to me when I can transform myself from a short girl with a relatively feminine face and obvious breasts and hips to a (still short) guy with a little makeup, a binder, and the right clothes. I like to cross dress because I want the experience of being someone else and I don’t feel like that “someone else” has to be a woman.

To explore the other gender, or the clothes are sensuous and comfortable. It is also mental. Right from childhood boys and girls are treated differently, so some may get curious to cross to the other genders dressing, and some may go further by changing their gender as well. World is diverse!!

There are almost as many reasons as there are cross-dressers.

Everyone does it for different reasons. Most that I have talked to just want the freedom to wear something soft and comfortable and shake of their male stereotype clothing as well as attitude.

Lots of Reasons!

Because they feel more comfortable

Because it turns them on

Because they are social experimenters

Because they are transgender or trying to figure out if they are

Because they are curious

Because it makes them feel close to the women/men they desire

Because they like the fabric/look/feel

Because they enjoy the feeling of transgression

Because they don’t care or know about gender norms

Because they want to set an example for others

Because they think its funny or silly

Because it makes them feel powerful

For me, it is because I now have a body shape more like a woman. So, women's clothes fit me better. I feel more comfortable and confident in clothing made for my shape, which is more like a female than male.