Why do men cross dress?

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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846 Comments - Leave a comment
  1. todd says:

    OMG its 100 here and after a long day in a hot ass building working my balls off in this heat i got to come home and thow on a skirt and let it all air out feels soooooo damn good

    • william says:

      Amen I agree. Skirts keep men cool with there package. I love them cause there open and refreshing and like this person I sweat like no tommorow. Also the reason I wear women clothes is because they are more comfortable and they have so much more to choose from and are not so plain like most men clothes.

    • dorthy says:

      its 100 here to but even nyloyons make u feel cooler nice small sexy panties maybe even lace nylon or lace blouse lipstick nail polish high hills and walk outside over vents soo nice

      • scott says:

        Yes the mens design and selection is by far the worst I have ever seen. Why would you even buy any of that junk. Womens clothes are lighter, brighter, and more comfortable to wear. Hands down the reason I crossdress to enjoy real clothes.

  2. rick says:

    This is interesting for me….my brief story is when I was 3 my dad died my lovely young mom was a widow. Sometime after dad died, one day mom was putting on her stockings, garters and beautiful lipstick and I wanted lipstick on me. So she put it on – I was probably 4, and she did it several more times. I liked it, but was shamed by a male friend/neighbor who came by one afternoon while I was wearing lipstick. He looked at me and started mocking me saying I looked like a little girl, and I remember him telling her not to do that because it would make me a sissy and she never did it again. Then another incident. This is true I sware. We had a neighbor husband/wife with 2 daughters roughly my age and they would babysit me occasionally. Each time I was put down for a nap in the adult’s bedroom, there were her stockings all perfumed up on the bed, alone with other feminine clothing. I remember putting my face on them and just breathing all that very feminine stuff into my being. Loved it and I do remember having orgasms at that very young age (they were without ejaculation). I think the seeds for loving female stuff were sown via those 2 experiences as a young boy.

    Fast forward to mid teens I suddenly became aware of mom’s stockings and lipstick and would put them on when alone. It was very arousing and I’d unload every time. Then I met my first real GF and all that went away as we were very involved sexually and that remained until I was drafted in the military. After that I got married and had a few kids and lots of living a normal male life with hard work and lots of good stuff.

    Last year my wife threw me a pair of her panties because I didn’t bring enough of my own for a 2 week vacation. (It was purely an accident that I didn’t bring enough of my own, NEVER thinking of putting on her undergarments.) Her panties were nylon/satin high cuts and when I slipped them on (a little reluctantly because they weren’t mens underpants). I instantly got this warm feeling in my lower stomach. They felt so friggin nice, and they were so comfortable that I said to her “these feel great! – and so comfortable….”. I’m not a kid anymore and this came as a big surprise to me. Pretty soon I found myself getting my own panties and then one day I got some pantyhose and man those felt great on my legs. This was becoming a big turn on. I started getting feelings about putting lipstick on and every time I made a move towards the feminine stuff, I got more turned on by the fact I was doing it, and by the deed itself. I finally ordered a satin skirt/blouse (labeled “sissy” by the seamstress) and a pair of high heels and a garter belt with lace and stockings. Put all that on with some lipstick and a bra with some padding for cycling that I had and wow, one look at my hosed legs with that satin skirt and heels lipstick and it’s pretty tough to forget about.

    I don’t consider myself a CD, but perhaps I am to some extent. I’ve been wearing panties every day for a year now, nothing else and my wife of course started it and it doesn’t bother her at all – “be comfortable”. But it’s becoming more than comfort, and it’s getting a bigger hold on me….so now if I get too excited and do release, I find I regain my composure and can walk away from it all. I am very secure in my manhood, but I do find it very exciting to touch the feminine that closely and I can’t quite put my finger on why. Why? Why is it so intoxicating? I did a little reading about forced feminization and did it while wearing pantyhose and satin lacy nylon panties with lipstick on. I was just oozing for a couple of hours…..very intoxicating.

    So in a nut shell that’s my story regarding this new-to-me thing. I can’t imagine it going any further because there is not a chance in a hundred billion that I’d let another male near me, so it’s not that. I think it’s the closeness to the feminine that’s such a draw – I love the feeling of women’s clothes…..

  3. Blake says:

    To Rick,
    So very cool.Loved the story,and hats off to ya.Men need to be liberated !

    Blake

    • Rick says:

      Blake, thanks for the reply. Took me a while to respond. I really don’t know what’s happening on my end, because today my wife and I went thru her intimates and she made a pile of her panties that “don’t fit anymore”, including some lacy totally feminine bikini light green satan, and a few totally lacy panties. I’m baffled that she thinks it’s so cool for me to wear them. I’m delighted because the only time I will wear white cotton men’s underpants now is under my jock strap/cup I wear when playing infield softball in a men’s league (I’m a damn good infielder!). I don’t know why this was such a turn on for me but I got an erection when I slipped on the green lacy panties and they’re covering my butt as I type. Ya gotta love it! She’s such a blessing to me! And she also gave me a pair of her pantyhose which are incredibly silky on my legs, that I’ll save for cooler weather.

      Anyway I thought you might enjoy. Good blog site. Some comments I have to admit I feel sorry for the guys who are in the throws of some bad stuff…..I think you have a pretty healthy attitude towards your fondness for feminine clothing. I love the materials they are made of. I’d love to find a blouse made of something light and silky that would pass as a man’s shirt….I’d snatch it up….

  4. diamond tweeks says:

    Mine’s a strange one because I’m split right down the middle, one side of me is all rock macho man love woman to death which is how I am 98% of the time and there is the other side to me that couldn’t be more different, different as in girly to the extreme! and that’s where cross dressing plays a hand, I cross dress purely for sexual gratification, they say cross dressers aren’t gay but I do beg to differ because when I cross-dress I want to be with a man so much, OK yea I am bisexual but I cross dressing to express a need for being a woman and being with a man for sex and feeling the need to be taken advantage of and abused sexually, I’ve spent years working out why I feel like this with out no explanation, I’m 33 now and I’ve learned to deal with it, I love both Men and woman 50/50, when I’m not wearing girly clothes then I have no desire to be with a man or wanting to be woman, lol it’s an odd situation I think but that’s the way it goes.

  5. Blake says:

    For me on the skirt and so on subject,i like female clothing better for many reasons,but,it has nothing to do with arousal
    or trying to look female…I just like what i like simple

    best to ya

    Blake

  6. Rachel says:

    Yeah, I’m pretty much on the same page as you guys. I still like women and think they are sexy, but a lot of times, if I see a sexy girl on TV or even in real life, I.get jealous becuase I know that, as a man, I will never be as soft, silky and feminine as some women out there.

    Maybe that’s just the whole male.dominance thing of wanting to be the best, but, I have never been as turned on as when I think about playing the girl and letting some muscly, strong guy (exact opposite of me).turn me around and do me like a dirty little girl.

    Sorry of that was a little explicit, but hey, what can I do? It’s definitely how I feel, and I’m tired of having to be embarrassed by the true passions.that I feel and want to feel inside my body.

    • dorthy says:

      on jelous subject i wish i was female cause they get away with cheating dress code i find myself staring in jelousy instead of focusing on work this won girl wears white short and i think about there periods i get trying to tell what kind panties she wears with it she hides them well

  7. dorthy says:

    me my favorite is wear a negligee to bed or dress u don’t even sheet to bed u can feel cool breeze of airconditioner up your dress a slip nylons are even better i am getting more confterable around my kids i cant wear it out cause wife dont accept but i cant wait for kids to go out so i can go full time female truck driver i drove in military and itreally helps u see the sexy things girls do in a car and pink lipsick is hardly even vissible in public i wear it as chapstick and panties all the time a bar to work in winter is nice too

  8. Kathleen69 says:

    When I was little I was molested and a few yrs later I was dressing in my mom’s clothes. I’ve been doing it for 30 yrs and will continue til the day I die. What was done to me then, I felt like a woman. Maybe that mind set is what got me started, not sure.

  9. biboybum says:

    I was sexuaky imprinted at age 15, a shy, ackward, very hu\orny young boy very attracted but shy and scard withgirls, found panties and put them on to see what a girls ass looked like, next was dildo’s to feel what girls feel fucking, neever felt comfotale deing domiate with girls or guyss, felt weak,scard and worthless infrott of girls snd guys, felt sexy, feminane, and submisse instead, like I deserved to be used,forced, punished or whatever bi the man/women dominating me with no choice , but to except smy role as submissive.

  10. Blake says:

    To Rick,
    RIGHT ON…she wants you to wear sexy undies,thats why she did what you said she did.That is just freaking fantastic.Take advantage of it.I would.My g/f and i are talking about doing
    small implants for me.So now the ball is in my court to decide
    to do it or not,she even said she will pay for them.How lucky
    can a guy get !

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