Crossdressing and Curiosity

I believe that much of the desire to crossdress is about natural curiosity.  This was the case for me, and I’m sure it is the case for many others as well.   Growing up in our culture with its many gender stereotypes and gender divisions, we often wonder what it is like for the other side.  Boys wonder what it is like to be a girl and girls wonder what it is like to be a boy.  They are curious about the others’ different bodies.  They are curious about the different things they get to do, and the different things they get to wear.

Even as adult men, many crossdressing desires are partly about curiosity.
What does it feel like to walk around in high heels?  Is it hard or easy?  Is it fun?
What does lipstick feel like on my lips?
What does it feel like to have earrings dangling on my ears?
What does it feel like to wear a skirt in the summer?  Does it feel cooler?
What does it feel like to have the wind blow up the bottom of a dress?
What does eye makeup feel like on my eyes?
What does it feel like to wear a satin nightie to bed all night?
What does it feel like to have my legs shaved?

And so on….

But it can take on a deeper level as well (which can be more disturbing and damaging in your life).

What does it feel like to go out to eat with my wife dressed as her girlfriend?
What does it feel like to have sex with my wife dressed as a woman?
What does it feel like to have men notice my looks and have their eyes drawn to me?
What does it feel like to have a man flirt with me and tell me I am pretty?
And maybe not super common, but at least some crossdressers wonder – What does it feel like to have sex with a man dressed as a woman?

In some ways curiosity is a neutral thing, and even a good thing.   God created us to have a sense of wonder and curiosity, to enjoy exploring his world.  We long to learn new things, and experience new things.  Curiosity is a very important thing.  But curiosity can also be negative.  If we do something sinful or harmful out of curiosity, than it is wrong.  Curiosity not a bad thing in itself, but it led me to rationalize crossdressing.

The problem for me was 2-fold.  First, I pretended to myself, basically lied to myself, saying that curiosity was the main reason I was crossdressing.  But in reality, curiosity was only 5-10% of the reason I was doing it.   How many times can I wear high heels and still attribute it to curiosity?  I crossdressed hundreds of times, but still somehow tried to pin it on curiosity.  It was more about sexual thrills, excitement at doing something forbidden, and wanting to be someone who I was not.

Second, I knew I believed crossdressing was wrong and harmful for many reasons, and yet I would use my curiosity as an excuse to give in to crossdressing.   Ah, the power of rationalization.  This would be bad even if 100% of the reason I wanted to crossdress could be attributed to curiosity.   At times, I could think about my belief that crossdressing is sinful and displeasing to God, I could think about the danger of my wife or others seeing me crossdressed, I could think about how dirty and shameful crossdressing always made me feel afterward, I could think about how much of my crossdressing desires were based on jealousy, and yet I would let myself give in to crossdressing because of curiosity.  All of those reasons not to crossdress didn’t matter, because I rationalized that since I was curious to know how a certain dress would feel on me, that it was okay.   So so stupid and illogical.

A good lesson for me to remember is – “Curiosity killed the cat.”  I must never again use curiosity as an excuse to do something I believe is wrong and harmful.


11 comments on “Crossdressing and Curiosity

  1. John says:

    Interesting post, Thorin but what is it about some of us that causes our curiosity to become something much stronger and compulsive. I think men, in general are more susceptible to sexual urges and so our curiosity about sexual things can lead to compulsiveness. For most men, I think that compulsiveness manifests in the form of pornography and desiring multiple sexual partners, whether acted upon or not. Steve Arterburn’s “Every Man’s Battle” books and programs addresses the commonality of that phenomenon.

    Why we were drawn to women’s clothing and behaviors is a common question we ask ourselves and has been discussed here and in other blogs. I think I was curious about women’s clothes but was already in an aroused by images of women wearing them, the first time I tried them on. I was further aroused while wearing them and from that point forward, the pleasure became reinforced on an ongoing basis.

    Once, when we were teenagers, my childhood friend tried on my sister’s pantyhose out of curiosity, just as I had done many times, except that he did not seem the least bit aroused and even found them uncomfortable on his legs. (The impropriety of what we did and I did on several occasions regarding the disrespect of my sister’s property is another matter, which I have confessed to God and others). To the best of my knowledge, he did not seem the least bit drawn to repeat that behavior again and based on my knowledge of his sexual history with women, he is not likely a crossdresser or drawn to fetishistic urges. He was a bit of a womanizer and had substance abuse issues, however. Curiosity to try drugs has certainly resulted in addiction in many people, to be sure

    I think most men rarely give women’s clothes, makeup, or grooming regimens a 2nd thought and if they do, it surely does not result in compulsive repeated obsession about it, like we are capable of. But as you say, curiosity can be an issue regarding any sexual thoughts and for anyone can result in being sucked in if one is not careful. At that point, it can be easy to rationalize repeated behaviors away as mere curiosity.


  2. Vivienne says:

    Interesting points, Thorin.
    I only partly agree with your opening statement “much of the desire to crossdress is about natural curiosity”. To be sure, like you, I have found myself dwelling on the subject of crossdressing, and considering many of the experiences and phenomena which you go on to list. However, I am sure I would not be considering them if I was not drawn to crossdressing in the first place.

    I am naturally one of the most curious of people; I think scientists tend to be curious anyway. My curiosity has led me to some things which I have found upsetting or disturbing, so it hasn’t always been a positive thing for me. On the other hand, there are many experiences which some people regard as highly pleasurable or desirable which I have never done; not even thought about.

    What does it feel like to run a marathon? What does it feel like to climb a high mountain? What does it feel like to drive a car at 120mph? What does it feel like to shoot an animal for sport? What does it feel like to steal a small sum of money? What does it feel like to smoke this funny herb? What does it feel like to sleep with someone who isn’t my wife?

    Some of these activities might be considered innocuous; others might be considered unacceptable or illegal. But some of them have the thrill of the forbidden (this is true of crossdressing for me), and others offer other pleasures which some people expend a great deal of their resources attempting to pursue. But my curiosity about these is limited to no more than a passing theoretical consideration. This is in marked contrast to my frequent ruminations about crossdressing.

    Therefore it isn’t curiosity which leads me to crossdressing. I am still not 100% sure of my motivations, but it seems to be primarily a desire to experience or enact a certain emotional profile which I seem unable to achieve any other way. Secondarily, there is a pleasurable physical or sensual component which is undeniable. The curiosity (acrylic nails? Hmmmm….) is secondary to that, and is what leads me to experiment with crossdressing to see what “works” best.

    Kind regards,



  3. thorin25 says:

    John, great point. I didn’t really talk about what it is that brings it beyond mere curiosity in our cases. If you want to write up a post tackling that subject, I would surely be interested, and could make a guest post out of it for you 🙂

    Vivienne, I like your other questions about things you are curious about, and you are right that those other things we may be curious but we don’t actually do them, (or don’t feel like we “need” to do them). So surely crossdressing is not “just” about curiosity. There is something else about it which moves it beyond curiosity to compulsion. Or rather, there are probably a lot of something elses which move it beyond that point. I have written about some of my thoughts on that elsewhere, but more needs to be said to be sure.


  4. Vivienne says:

    Helen Boyd writes “The phenomenon is stubbornly inexplicable, a cross between a compulsion and a wish.” I couldn’t put it better.


  5. Ralph says:

    That’s a great quote, Vivienne. I’m not really a big fan of Boyd and MHB — Betty leans much farther into full transsexual territory than I am comfortable with — but that’s a good description.

    Since my first experience was some 40 years ago the details are pretty hazy, but I suppose Thorin’s premise does apply: I caught sight of my mother’s girdle and wondered what it would feel like on me (pretty disappointing, since she was a full sized adult woman with several children who had stretched her and I was a skinny little 10-year-old). But that still begs the question, why did it ever even occur to me? Most boys never get curious enough to find out what it feels like; what makes us different? And even though the fit was ridiculously loose, why was it so appealing to me that I kept going back to it again and again? Even then I knew it was something deviant that would bring me a lifetime of humiliation if I was caught — I remember I was wearing it under my t-shirt and playing in my front yard when a friend unexpectedly rode by on his bicycle and stopped to talk for a while, and the whole time I was terrified that he would notice the strap bulges under my shirt or somehow otherwise know I was wearing something I shouldn’t. And even after that close brush with disaster I couldn’t stop.

    As I have noted before it wasn’t a sexual urge; I was still a good ten years away from my first climax and didn’t have the first clue what sex was about (my parents were… remiss in their duties in the education department). But it sure was an irresistable compulsion — and a wish, in the sense that in my weird fantasy life I explored the idea of being transformed into a girl (temporarily, always relieved to be back to “normal” afterwards).

    So… once again, I come to the conclusion that the driving factors that get us started and keep us addicted are too complex to sum up in a simple “this is why we do it” explanation. And that’s the point I just give up and take life one day at a time, not worrying about the why and the wherefore.


  6. thorin25 says:

    Ralph, interesting thoughts about your life as usual. I’d challenge one point maybe, and that is it could very well have been sexual, even without erection and climax. Sexual pleasure is more than just ejaculation or orgasm (especially for women). Think about foreplay. Think about seeing a cute girl for the first time and being attracted to her. What you were doing with the girdle may very well have been a sexual thing, in my opinion. The beginnings of a sexual desire towards women, but in this case, towards the “things” of women instead. The excitement and attraction were there, but it had yet to develop into stronger sexual urges.

    The reason I say this is that crossdressing for me I believe was always sexual, even though I didn’t know it. It was a while before crossdressing gave me consistent erections, and years before it led to orgasm. But it always had the same type of mysterious attraction and desire and even strange sort of excitement.

    Likewise, I would challenge you again to say that maybe your crossdressing today is still sexual, even though again, there is no orgasm present with it. In the same way that married couples can lie naked together and enjoy each other’s presence without sexual climax or even arousal, so also I think we can become so accustomed to crossdressing, that it brings the sexual comfort of a spouse, but no longer with the strong arousal.


  7. Ralph says:

    This is why I love your site, Thorin. You always give me a new perspective and things to consider that had not occurred to me in my extensive (excessive) self-analysis.


  8. Tony says:

    Like you Ralph, I was first attracted to trying to find out what it was like to wear my mother’s girdle. It was over 55 years ago for me (I was about 12 or 13). I’ve no idea what put the thought in my head, but I knew I had to wear it, and I found an opportunity while I had the house to myself. I remember the girdle in detail though, it was a white open bottom girdle, with rigid front and rear panels, elasticated sides, stiffening bones and a hookside fastening. Unlike yours, it was very tight on me and it needed a lot of stretching to get the hooks together. The whole time I was struggling into it, I was trembling like a leaf; the excitement of adrenaline I now know! I had this feeliing that I was trapped in it too; if anyone came home unexpectedly, I knew I couldn’t get the hooks undone fast enough to get it off and get dressed (I started deliciously naked) before being discovered in my mother’s bedroom. Very carefully, I also put on a pair of her nylon stockings and hooked them up to the suspenders. The feeling of those on my legs and the tug of the suspenders was electric. I didn’t know about tucking then, and I’d had an erection the whole time, so my member was really squashed by the corset, and that just added to the stimulation. Unlike you, it wasn’t another 10 years to my first climax, it was more like 5 minutes! I don’t know what prompted me to do a few press-ups, but I got a real kick everytime my torso hit the ground until the inevitable happened, and I was so scared; I had no idea what was happening to me, but I had no control over it. It felt like I was urinating into the girdle in spurts, but it felt so good……Until I realised that I had a major clean up job on my hands. Then panic set in; but either my mother didn’t notice (I became very good at covering my tracks) or she decided not to mention it.

    That was the beginning of a lifelong crossdressing habit, which unfortunately has been in the closet because my wife, who I told 30 years ago, and who I love more than anything else in the world, still thinks it is disgusting, knows I still indulge from time to time, and has encouraged me to just stop. It’s unlikely I’ll ever achieve an ambition of going out in public passably dressed (no wig or make-up yet), but after a start like the above, I’m never going to forget the association between that level of excitement and crossdressing, even though I’ve never achieved such a high peak since. The nearest I got to it was when I laced up my first real corset as tight as I could get it about 10 years ago. I felt “trapped” in that too; it takes several minutes to get that off, and feeling trapped just added to the excitement.

    I feel my motivation IS primarily sexual, except for the first time and I can’t explain that. Otherwise I’m a pretty normal heterosexual man, many manly interests, manly car interest (I’ve got a V8 Cobra replica for fun), manly job (Engineer) and very happy to be a man, husband, father and grandfather….except when I feel like a bit of fun crossdressing, and I need that only from time to time. I too no longer try to understand why it is, I just know it is, and probably will only stop when they start nailing up my coffin.


  9. Vivienne says:

    With respect to you both, I somewhat disagree. A pleasure can be sensual without being sexual. I often think (and have frequently blogged) that boys are not permitted to be sensitive, or pampered. I can’t tell you how often I was told to be the “big brave soldier”: who wants to be a big brave soldier? I still don’t!
    I was unable to articulate my feelings as a child, but a reasonable approximation to some of them would be this statement: “If that’s what being a boy is all about, then bugger that!”
    Quite recently I went to get my hair cut at a place I don’t usually go. The hairdresser asked me if I wanted her to wash my hair, and I thought: sure, why not? I can’t remember the last time anyone washed my hair for me, and the experience was incredible. I was somewhat transported! It wasn’t in the least sexual, but it was profoundly sensual, amazingly relaxing, and suddenly it struck me why women spend so much time and money in the hair salon!
    Pleasures like having someone wash your hair for you are basically “forbidden” to men. It’s certainly not OK to admit to your mates that you like stuff like that.
    I find myself wondering if the little boy (that I was) had access to pampering and sensual pleasure, if those desires wouldn’t have become twisted into the desire to crossdress. It’s something I am aware of in my own children, and I try to watch out for when they are vulnerable or sensitive and just want a cuddle or a cosy time. And I never tell them to “just be brave”.
    I think the desire for sensual pleasure is predominantly an emotional one. At adolescence, it becomes (I believe) inextricably bound up with the sexual awakening which occurs at that time. I know I was sexually aware at an extremely early age, but I am also aware that my crossdressing tendencies started much earlier still.
    Without doubt, I still enjoy sensual pleasures enormously (and I am still driven by emotions). As time goes on, crossdressing is becoming less sexual and more sensual, for me at any rate, and the times when I enjoy it most are the times when I feel least sexually aroused, though there remains a sexual component to the pleasure.


  10. thorin25 says:

    Vivienne, you say “I find myself wondering if the little boy (that I was) had access to pampering and sensual pleasure, if those desires wouldn’t have become twisted into the desire to crossdress.” If you acknowledge freely like this that crossdressing desires are abnormal twisted desires, not what they should have been, then why don’t you work on trying to undo the twisting? Why not find sensuality in the ways that are not twisted and stop with the crossdressing? Because I agree, there is so much that boys and men are supposed to experience, “as boys” or “as men”. It is not right to have to crossdress in order to try to feel those things. That is why I argue for not crossdressing but rather living as a whole man, a real human being, who can feel things like we are supposed to, even if our culture tries to pressure us otherwise. Do you really want to be a person who has to hide in the closet and put on a dress in order to experience certain normal life pleasures and emotions? Wouldn’t it be better to learn how to integrate those feelings into your real life?


  11. Vivienne says:

    Hi Thorin, nice to see you back.

    I am still trying to work out for myself whether becoming a crossdresser was an inevitable event for me, or whether the events of my childhood which attempted to “make a man out of me” somehow made it happen. For the moment, I am inclined to think that it was the latter. I think that crossdressing is basically abnormal, and that a well-balanced, emotionally aware individual (in a tolerant, enlightened society) would be able to have his psychological needs met without it. In this I think we are agreed.

    It’s certainly true that I sometimes wish I weren’t a crossdresser. You ask: do I really want to be a person who has to hide in the closet and put on a dress in order to experience certain normal life pleasures and emotions? No, of course not!

    However, integrating these into my real life isn’t that easy. I basically accept that my inclinations are innate, essential, and unchangeable. It just hasn’t been possible to create an environment in which it is permissible to have them met overtly, and please believe me, I’ve learned that lesson hard, over and over; from my parents, my schoolmates, and more recently, my wife. Men are expected to behave in certain ways, and those of us who don’t quite fit that mould can find ourselves severely ostracised and made profoundly unhappy.

    In addition, I believe that many life events can’t simply be undone. Each of us is the product of our experiences. In this, I am firmly with Fitzgerald: The moving finger writes; and, having writ, moves on: nor all thy piety nor wit, shall lure it back to cancel half a line, nor all thy tears wash out a word of it.

    For me, crossdressing isn’t an addiction (the definition of which, I suggest, is an activity which is in control of you, not vice versa), but it is both a pleasure, and a refuge. In brief, I can’t get my emotional needs met any other way. If I could, would I stop? Maybe, after a while.

    I admire your determination to follow a different path, and I wish you nothing but success; but in my case, I don’t think that path would be successful.



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