Why do men crossdress?

Girl friends and wives want to know.

Why do men cross dress?

Why does my husband cross dress?

How can I make him stop cross dressing?

The unfortunate truth, is that there is no simple, one line answer to these questions. If there were, you probably wouldn’t be reading this article, and the debates on this topic would be silent.

In my personal experience, the fascination with woman’s clothes started when I was very young. I must have been about four years old, and I remember going to great lengths to procure and then wear my mom’s nightie. My most vivid memory is as a teenager, nervously buying a pair of pantyhose from a local supermarket and then wearing them home under my pants.

I felt (and still feel) a need to wear woman’s clothes, and I can’t quite explain where it comes from. The media like to think of cross dressing as a sexual perversion, and so naturally they see the desire to cross dress and purely for sexual gratification. The problem with this theory is that when I (and many others) first felt the desire to cross dress I didn’t know what sex was.

Many cross dressers I’ve asked describe the need as ‘feeling more comfortable wearing woman’s clothes’. This is sometimes (but not always) coupled with the desire to be seen as a woman. To not just dress like a woman, but behave like one as well, to wear make-up and otherwise pass as a woman. There are others who cross dress for sexual excitement. The need to cross dress is indeed a spectrum.

That still doesn’t answer the question why do men cross dress?

Marcy proposes a few interesting answers to this questions.

One argument is that transvestism of cross-dressing is a way of offering a challenge to society’s preconceptions about gender. Some men cross-dress because they are unhappy at being men. Others didn’t mind the male state, but also like to put on women’s clothes occasionally. Some men cross-dress simply to make a passing social or fashion statement, and some because they have emotional needs that can only be met by the comfort that wearing women’s clothes gives them.

Yet the true reason why men cross dress remains somewhat of a mystery. It is intensely personal, often confusing and sometimes guilt ridden. I’m hopeful that as society grows more tolerant of diverse gender expression we will see more cross dressers and transgendered stepping forward to share their stories. Without the need to justify their behavior, and no longer shamed by society perhaps we will be better able to answer this baffling question.

Comment and let me know, I would love to hear- why do you cross dress?

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  1. Scarlett398 1 year ago

    Hi girls, it’s Scarlett and I wanted to ask this question in a different kind of way by asking you when your wife found out, one way or another, that you were a cross dresser, what were the reasons you gave her (after she stopped freaking out) as to why you love the thrill of cross dressing?

    Now I’ll start with not the reasons I told my wife why I cross dress because she still doesn’t want to know and wants me to keep it private and not cross dress while she’s present in the house. I also have to keep it private as a result of where we live and my wife’s employment position in our county. However, it the last two or three years, she’s come miles forward with her acceptance of my thrill to cross dress!

    Well, here’s my cross dressing story! I started cross dressing when I was about 9 years old. I was home alone from school and was doing some exploring in my mom and dad’s bedroom for some reason. I stumbled across two things that led me to my first day of cross dressing. One was my dad’s collection of Playboys and Penthouses he kept under their bed in way up on a shelf high in their closet. The next thing I stumbled across was about two or three drawers in one of my mother’s dresser that were full of sexy lingerie I’m assuming was worn when my mother and father were busy making love on the nights when all three of us kids were dead asleep on a Saturday night.

    In those two or three drawers of my mom’s were some of the sexiest lingerie they made back then. Black lace panties, black garter belts, black thigh high hose, and an assortment of other goodies – mostly black in color which is my favorite color in panties, hose, tights, skirts, dresses, and heels to this day which is decades later!

    That day, I knew my mom and sisters were at a girl scout meeting that would last for at least two more hours and my dad was out of town on a business trip so the coast was clear for a long time! So I put on a sexy pair of those black panties, a pair of those sexy black thigh high nylons, and a black garter belt and then figured out in about 10 minutes how to properly hook the thigh high hose up to the black sexy garter belt. After all hooked up, I grabbed several of my dad’s Playboys and Penthouses, laid them out all over the bed and had my way with myself for about a hour or so! I’m sure you are well aware of what I’m talking about. After that specific and fantastic day, I was basically hooked on sexy women’s clothing for life. So after that day, I would go in there anytime I knew the family would be gone for a while and the coast would be clear and have a wonderful time with myself for years to come!

    I never started to buy sexy things for myself until after I married my high school sweet heart at a very young age. I bought all kinds of female goodies inclusive of lingerie, skirts, tops, heels, makeup, etc. over the 24 years we were married and she or the kids never found out or had a clue I was a cross dresser. I kept the clothing and footwear in a couple of large leaf bags under the pink insulation up in our attic and kept the make hidden underneath a dresser in an unused bedroom. We divorced after 24 years as a result of an affair he had with a short fat troll who was living in an RV and who had been married and divorced four times before my wife had a six month affair with him before I found out and then filed for a divorce for unreconcilable differences after 24 years of marriage. To this day she has no idea I was and still am a cross dresser.

    Then many years later, I met my current wife on a very reputable dating site. We fell completely in love rather quickly, got married and have been madly in love for fifteen years! I don’t think I’ll ever be able to keep my paws off my sexy redhead. She came with no kids, a college degree, a career, no verbal or physical abuse, she was financially responsible and had gotten a divorce years prior to our meeting for the same reason I filed for my divorce – an affair outside the marriage her ex husband had with not one but several different women.

    Now my reasons for cross dressing is that fact that I have reached a level of cross dressing of when I get my total girl on as Scarlett, no one can tell there is a guy in that dress, skirt, booties, or heels with my makeup and accessories on. I’ve been told by many girls I’m really quite good at being more than just passable when it comes to cross dressing and that is verified on the rare occasions when I go out in public and apparently no one can tell that’s a guy in the cute dress or outfit!

    Believe it or not, I didn’t own one dress until about 3 months ago and now I have between 40 and 50 of them – half of them being Calvin Kleins. I was always self conscious of my arms being too muscular from working out in the gym. Now I focus on the core of my body and my legs when I’m working out and spend little time with sculpting my arms.

    I dress now because I love the look of Scarlett – my feminine side, which has taken many years to try and perfect. My clothing style is very similar and almost identical to that of my wife. I love to shop with her and help her pick out everything from dresses, to skirts, to tops, to heels, to purses, to jewelry, to even makeup. But I’ve only bought something feminine for me on three rare occasions while shopping with my wife. I’ll shop and look while she’s shopping and looking but I won’t make a purchase on something I like until the next day or so and I’ll go buy what I really liked while she’s not around and that’s how both of us like it! She and I would both feel awkward if I went up to the counter with dresses, skirts, and makeup to buy at the same time. I’m sure some of you girls can relate to that situation.

    One of the other main reasons I love to dress up as Scarlett is to take pictures of her with my Nikon D3100 or D3400 with the camera sitting on a Vivitar tripod that is adjustable in so many ways and I put the 10 second self timer on the camera that gives me plenty of time to get posed up in front of the camera with whatever props or accessories I need or location I desire to make the photos look professional, cute, sexy, and classy! I’ve been a semi professional sports photographer at big time college and pro gamed for decades and I’ve mated my photography skills with my cross dressing skills to have so much fun with my private Scarlett photo shoots which usually last from 4 to 6 hours and includes up to as many as 7 or 8 outfit changes over the course of a given photo shoot. Then I upload the photos and pick some of my favorites to share with you lovely ladies or the very small group of people in my area who know that I love to cross dress. My wife is the only family member who knows about Scarlett. Others include my hair cut girl of many years, the ladies at customer service on the second floor of our brick and mortar JC Penney’s which is were I go to pick up Scarlett’s heels, booties, or boots I order on line and have shipped to the store for pickup, a couple of girls in the ladies shoe department at the same store, some girls at Sephora at JC Penney’s or our local mall, and one or two girls at Plato’s Closet – my favorite consignment store.

    I am lucky enough to wear the same size of my wife with the exception of our shoe size, so I get to go into her closet and borrow whatever I need for a photo shoot if I need to borrow something from her closet. She knows I do this and knows when I borrow something like a top, skirt, dress, or purse that they will always be returned to their original places in the same shape they were in when I took them out of the closet. She’s very cool with me borrowing her things and she can always borrow whatever she wants from me as well. Pretty nice setup huh?

    No when I am home alone sometimes, I will, like the days when I was a kid, borrow some lingerie from her drawers or closet and have my way with myself to relieve some sexual tension if I haven’t gotten lucky with my sexy redhead in over a week’s time.

    So girls, this is how I got started with cross dressing and this is why I continue to do it! On three occasions, I’ve done a complete purge for religious or guilt reasons but I really wish I had all of those nice items that are sitting deep in our local landfill back because when I tossed Scarlett’s previous items, they were almost like brand new and would still be in style today if I still had them. I regret tossing the items out but if I had them back, I would need another 3,000 square foot house to store all of Scarlett’s discarded items! So maybe it’s a good thing they are in the bottom of our local landfill. The dresses and items I have now will never be tossed. My purging days are over and done with! No more purging for Scarlett. I’m so comfortable with myself as a handsome husband and as sexy, cute, classy Scarlett, I’ll never purge again and always maintain the feminine side of my personality with comfort and pride!

    Thanks for reading this novel girls and I hope some of my story relates to many or your stories.

    Take care and continue to enjoy our wonderful thrill of cross dressing in whatever way you choose to enjoy expressing your feminine side of you!

    XOXOXO Scarlett

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