The why do you want to cross dress conversation.

[1Ladyjade]

Last night wife and I anchored the boat hoping for a quiet cool evening on water. She recently bought us matching pocket dresses to wear as lounge wear in the evenings. She is ok with me in that but no bra or makeup. So just a man in a dress. While it's comfortable to wear I am not comfortable not presenting femme. So last night she asked why do I like to cross dress. I've told her in the past the dresses are very comfortable. So she reminded me that's what I had said. Then she says but you take it to the next level. You put on ahapewear to hide your man bulge and put on a bra and makeup to appear as a women. It smelled like a trap so I really couldn't give her a good answer to that so I just sort of let it go. The night before I showed her my hidden folder of Jade pictures on my phone. She questioned where did the blue shoes come from. I told her somebody left them in a trash bag. And they just happen to be your size. Well yea and so I couldn't throw them away. Then she saw a couple blouses she had thrown away. Is that my shirt? You threw it away I have lots of skirts but no tops to go with. I think she is getting used to the idea. But she lives too far in her own head. Since there is no logic to crossdressing she may never fully accept it. But Im not going to push and I will hope that someday she may want to meet Jade.

[alwayshave]

Jade, my wife is very accepting and has asked why I do it. I have no answer. It's a compulsion that I have always had and know that I'm never going to stop. She knows that I take care of her and I'm masculine other than when dressed and that's good enough for her.

[1Ladyjade]

She has said before her concern is that in the near future I am going to come to her and say I want to transition. But I do not. I am happy in my man skin. I just enjoy slipping in femme for a few hours if I can. But being I dress at work I know that at any minute they could call me and need me somewhere. At which point I am stripping Jade off and back to drab. When it was cold I would leave my stockings on put on my pants and resolve the issue and run back to get Jade out again. But now it's shorts weather can't be underdressing now.

[char GG]

It seems good that since she started this conversation, keep up the communication. There will probably be more questions. I suggest, just answer honestly, even if you don't know the answer yourself. She is trying to learn about YOUR thoughts. Since everyone is different, it seems this was a good talk.

[Jenn A116]

I've had my wife and a very good GG friend ask that question. I honestly answered that I really don't know why. I just enjoy doing it.

[kimdl93]

At least you are having the conversation and able to share your images with her without adverse consequences. Thats a step in the right direction

[Cheryl T]

I've been asked that many times.
I told one person that if I had the answer to Why that I could make a million dollars writing the definitive book on the subject.
I have no idea why but personally I believe it's genetic. I have my reasons for that belief, but no proof it's true. After decades of searching for the answer I finally relegated it to the Big Foot category. The answer may exist, but I haven't seen it. Once I gave up the search life became so much easier.

[Pumped]

I told my wife if she could figure out why we like to dress she would be a rich woman!

[Stephanie47]

When my wife and I had "The Talk" back in the early 1980's the "Why?" question arose. After some bullshit answers I told her "I do not know why I do what I do!" I also told her I wish I did not do what I do. Frankly, life would have been a lot simpler if I was not driven to wear women's attire. My recommendation for any man trying to explain himself is to avoid saying something to a woman akin to "getting in touch with your feminine side." If my wife and I were to have a conversation I could tell her how wearing women's attire makes me feel which does not answer the question of why I may have chosen wearing women's attire in the first place.

Ladyjade's wife asked a valid question. If a guy finds a dress more comfortable than "X" why does he strap on a bra with false boobs, makeup and a wig? My granddaughter raided my closet and took several of my flannel shirts to wear with her young men's jeans which fit her better than women's jeans. She has long hair; currently blue. She does not apply false facial hair. She does not roll up a sock and stick it in her pants.

I really cannot explain why I am wearing a long white nylon nightgown as I bang away on the keyboard.

[Kris Burton]

It seems most folks are saying here "I do it because I enjoy it" or some such variant. I think that's an excellent reason for doing something.

[Elllie]

Really if you think about it, asking 'why' is quite an odd thing to do. I doubt many would ask that about other interests that people have. Why do you like reading, playing sports, going to the theatre? You like these things because you do.

[MarinaTwelve200]

Started as a fetish, but NOW I find it is a "Vacation from MYSELF"---An escape from ME and all my little worries and also an escape from the stresses and obligations of "manhood" itself.---I can COMPLETELY relax and unwind and relieve ALL my stress. not to mention the erotic effect and the feel of simply "being pretty".

[Leelou]

When my wife and I had "The Talk" back in the early 1980's the "Why?" question arose. After some bullshit answers I told her "I do not know why I do what I do!" I also told her I wish I did not do what I do. Frankly, life would have been a lot simpler if I was not driven to wear women's attire. My recommendation for any man trying to explain himself is to avoid saying something to a woman akin to "getting in touch with your feminine side." If my wife and I were to have a conversation I could tell her how wearing women's attire makes me feel which does not answer the question of why I may have chosen wearing women's attire in the first place.

Ladyjade's wife asked a valid question. If a guy finds a dress more comfortable than "X" why does he strap on a bra with false boobs, makeup and a wig? My granddaughter raided my closet and took several of my flannel shirts to wear with her young men's jeans which fit her better than women's jeans. She has long hair; currently blue. She does not apply false facial hair. She does not roll up a sock and stick it in her pants.

I really cannot explain why I am wearing a long white nylon nightgown as I bang away on the keyboard.

That's an interesting take that you don't think that's a good idea. For me personally, I've used a variation of that to explain why I like to crossdress. I don't use the somewhat cliche "getting in touch with my feminine side". Rather I express what my best understanding of what and who I am. I say that I feel that I fall on the Transgender spectrum. There are aspects of my personality and identity that do fall on the feminine side. Wearing women's clothes helps me express that feminine side of myself.

So for me, I find the question pretty easy to answer.

[DianeT]

This is the problem of pretending it's just for the clothes when it's not. If it's just for the clothes then you don't need wigs, boobs and hip forms. My wife asked the same question. I told her that my dressing was initially motivated by a curiosity and fascination about females, with some level of identification (not a female side, but simply wanting to try some taboo, sensual experiences), with a clear sexual driver (even though I started before puberty).
It has evolved since I bought my own clothes at 50+, now I am more interested in playing with the female presentation and its various incentives (feeling elegant, enjoying the game of transformation, feeling complete by venturing on both sides of the gender separation line). But, but, but, and I told this right after I came out to my wife: there is always an erotic subtext to my dressing. It used to be the main motivation. Not anymore, and my sessions have turned lately more into a dressing showroom where I try different looks. But even if it receded, it is still there. I am a heterosexual man and I can't immerse myself in a sea of female cues (boobs forms wig) without some level of trouble and tingling. The taboo of crossing the line, the shock of appearing in the mirror as a woman, has an harmonic to it that comes from that erotic vibe.
So, it's not, it never was, just for the clothes. And that's ok. That, and a ton of other vibes and feelings, is what makes the experience so rich and enticing.

[April Rose]

One of the most productive conversations I ever had with my late wife was when I finally admitted to my self and to her that I really couldn't explain why I was the way I was even to myself, let alone to her. It can't be defended logically because it is not about reason it is about feelings and emotions.

[Mary Loo]

This is a really interesting thread.

Jade, I had a similar conversation with my wife a few weeks ago. It went similar to several posts here. She asked, if it was just about the clothes, then why the wig and makeup ( I have only bought my first wigs about 2 months ago, and have only practiced with makeup four times, now ). The point was she was seemingly better with it all when it was just clothes. Now she is more concerned I think, and honestly, the biggest issue is she just can’t understand and I can’t do a very good job of explaining it or giving her satisfactory answers. She understood better as a sort of sexual taboo/turn on and much like Diane it is evolving for me, though still at its core it is mentally a little arousing, but not so much physically anymore. It is more about the emulation and presentation to me, than the previous experience of simply the dressing. She is actually more concerned that it isn’t as sexual anymore. I truly wish I could explain it better, but she has never really been the overly girly type ( even less so as she ages ) and considers getting dressed up and makeup and such not as “fun”, but as work and a hassle and much like most on here, is never quite fully happy with her results.

We were having a conversation this weekend at one point discussing way back when, 30 years ago, when she was bridal shopping and again, she saw it as a job and annoying to have to “figure out” all the dresses to try on and how to get in and out of them. She told me at one point she had tried a pretty expensive dress at a nice boutique near her job at the time. I asked did it feel extra special or nice and she basically replied, meh, not so much. My whole point is the argument about feeling pretty and feminine and playing dress up it lost on her because she doesn’t necessarily enjoy it, herself, so even harder to understand why her man would.

She has been wonderful and trying not to play spoiler to my habits and even has been helpful with some purchases and advice, but wants NO part of seeing me or pictures or ever truly understanding, even if she herself is trying to be understanding of my feelings.

The whole thing is a big, crazy, confusion of I don’t knows, but I do appreciate reading about everyone else’s situations and conversations. It is helpful.

[NancyJ]

The question Why is often a shame-inducing question as in when parents ask their child why did you hit your brother, or a wife who disapproves of her husbands drinking asks why do you drink so much? There is usually no satisfactory answer as the person asking the question really is just expressing their disapproval. Why do I dress?: Personally, I dress to soothe my gender dysphoria. It calms me, and I LOVE feminine things. This is, honestly, what I have told my wife (and she does not like this answer). Nancy

[Leslie Mary S]

To me the question is "Why do I dress feminine?" The only answer to myself is "because I like the feel". Then I ask "Why the bras, forms, and hip pads?" and the answer is "They fill out the clothes to the design/form they were cut for." Then I ask myself "Why the makeup, wigs, and shoes?" and my answer is "The outfits I am wearing just look better with all the assorted support things that a woman wears with them". To me it is the feel AND the look that I like.

I ask you why do you wear a bracelet or a necklace when it is the feel of the cloth and the cut of the cloth that you claim that you do it for?

[AngelaYVR]

Maddeningly, the best answer to the question is to show them but you can’t get to that stage until they are happier with your reasons. Swings and roundabouts. After my wife had been out with me a couple of times and saw how I lived this part of my life then she understood that it was who I am, woven into my tapestry as surely as a fish knows how to swim. The why is a blind alley, we just are! But nobody is going to be happy with that explanation.

[Leslie Mary S]

The reason I answered the way I did is because there is no one asking me "WHY", I live almost alone.
I have a just a mildly supportive GG renter in the opposite end of this mobile home.
She needs the room and can't afford a home of her own, so she just accepts me for what I do.

[Mackem Sue]

Why? Heavens knows. I've stopped asking.

I just enjoy it. Being single, the why question hasn't been asked of me.

Sue

[nancy58]

I don't know "why", I just know that I want to dress up. At this stage in my life (60's), I don't really care so much about being a man, but there's no magic fairy who could make me a woman AND also resolve all the fallout that would come with it.

[MonicaPVD]

We spend so much time rehashing the why, to no one's satisfaction BTW, when we should just be enjoying the ride.

Why? Because we can.

https://youtu.be/g_cwuRmjhsY

[Georgina]

I live alone so I dress whenever I want. Last year I told my sister and she has been so supportive and gives me clothes as well. Only last Sunday she visited and we were looking at my clothes and photographs and I apologised for going on about my like and dislikes and said that I don't really know why I do this. Her reply was don't worry, you enjoy it, you are not harming anyone why would you want to stop. I am happy she is my sister.

[BrittanyB]

What a great sister, Georgina! And she's right...if you're not harming others and you enjoy it then just let it be.

When I was in the closet (45 years), I didn't really attempt to understand why. It just didn't make any sense to me other than I enjoyed it. Of course there was a great deal of shame and guilt wrapped up in it for me at the time as well, but the psychic relief of dressing was greater than the shame and guilt, at least most of the time (those soul crushing purges...ugggh!)

After being discovered by my wife of 16 years, I couldn't answer this question, "why?", and she was not satisfied with "it makes me feel good" answer. She challenged me to really try to understand why and over the next 5 years I worked hard on the question from two key angles, intellectually and emotionally. I am proud to say I have come to a reasonably good understanding of "why" (for me), but it was painful getting here. I won't detract from this thread with the explanation, I just wanted to say that satisfactory explanations can be achieved if the motivation and stamina is high. In retrospect, I am glad I worked to find a satisfactory explanation, but if I was single, I would have been ok with leaving it as "it doesn't hurt others and I enjoy it. The why is nobody else's business".

[CynthiaD]

Some things can’t be explained in words. Why does one melody sound beautiful, while a similar melody sounds bad? You can analyze it, but it really doesn’t help much. When I get all dolled up with makeup a feminine wig and nice clothes, I can look in the mirror and know why I do it. But explain it in words? No way!

While it’s true that skirts and dresses are way more comfortable than pants (I hate wearing pants), it doesn’t go far enough, for me. For me, skirts and dresses feel correct. Pants do not. Don’t ask me why.

[countrygirl]

I had the a similar conversation with my family when they asked why. Of course the question started to fly was it a turn on or did I want to be a woman. I explained that no I just feel better when I get to express this side of me. My sister understood better than parents but she is 2 years younger than I and has friends that have transgender family members. I really couldn't explain it partly do to them yelling and screaming and calling me all sorts of nasty names. It is hard to understand. I tried to get them to come to the local support group to just to listen to the other folks stories because in reality in we all have such the same story. I have accepted this part of me a long time ago. I don't fight it in embrace it and I actually enjoy it better now that I have not fought it. I am looking at micro dosing hrt. Not to transition but to help with the dsyphora. Talked to my doctor about it and he mentioned that I would need to see a endocrinologist. Some days I want nothing to do with being Amanda. There are other days that I can't stop being her. I let it happen when and how it happens and frankly I am SO much happier now I do this and everyone of us needs to find our own way to do this. If I can only find Mr. Right who understands this.

[Teresa.Smith.VA]

I told my wife if she could figure out why we like to dress she would be a rich woman!

I told my wife that if she would get paid for every hour we discussed why I like to dress she would be a rich woman!

[Pernille Tiratzo]

I just had this conversation with a male friend, very respektfull and a good person. Offcourse he asked this question, "why?". I told him it made me feel happy and pretty. He smiled and said thats a reason as good as any. I agree.

[SuzyZahn]

The `why`?
I told her, its sexy
i told her, it relaxs me,an escape
I told her, it feels delish
I told her, it heightens all my sensesI told her, makes me sub to her
I told her, no I wont transition
I told her, I did this before I knew her,,,and i`ll do it after i know her if she prefers
I told her, Its `Me`and I adore it

[Veronica Lacey]

Hey there Ladyjade...

It's a truly beautiful conundrum that your wife still pursues her interest in who her husband is, that you both can share discussion in this way, yes? She does not sound confused so much as fascinated by your depth, perhaps something much less common with many other men she's ever known.

I'll avoid the dissection of the philosophical theory behind this reply (as it would be too ironic) and suggest that I tend to subscribe to something along the lines of "Occam's razor" which "in simplicity: of two competing theories, the simpler explanation of an entity is to be preferred."

The rare moment so many years ago now when my wife asked me the "why do you..." question I replied that I just do. I can supply all manner of history, hyperbole and conjecture if it pleases but the bottom line is the simplest explanation. I find preference in wearing a variety of "female" attire as much as preference wearing a variety of "male" attire. This belief provides as much sensible explanation as to why I tend to choose chocolate over vanilla and strawberry (but could enjoy them all), rejoice in rainy days with or without an umbrella and boots to sunny days with or without sandals and sunglasses (but could enjoy all) or wish to be more than one place at the same time.

I long ago detached from overexplaining this one to anyone so long as I feel comfortable reasoning it to myself. I know the answers for me and have no way of bending my truths to make it more digestible or plausible to another.

It's a good life even if it goes without explanation sometimes :thumbsup:

[Camille58]

Being fairly new to crossdressing, I have asked myself this question a lot. And, I have yet to come up with a completely satisfactory answer. And I am beginning to not care! Maybe I shouldn?t question something that touches me on so many levels! I have spent a lifetime searching for something to calm the overactive thought process in my mind, and nothing works as well as this. Not meditation, not exercise, although they help some. But there is something about getting into femme mode and snuggling up to a good book that is just heaven! I would be lying if I said that there isn?t a sexual component to it. There is, and that?s nice. But anything that makes you feel this good is bound to enhance that part of life also, I think. You know, maybe I just answered my question!

[Julia1984]

Maddeningly, the best answer to the question is to show them but you can’t get to that stage until they are happier with your reasons. Swings and roundabouts. After my wife had been out with me a couple of times and saw how I lived this part of my life then she understood that it was who I am, woven into my tapestry as surely as a fish knows how to swim. The why is a blind alley, we just are! But nobody is going to be happy with that explanation.

That is the most concise, most accurate and most truthful thing I have read on here for really quite a long time. Thank you. It's brutal, but it's right.

[Rachelakld]

I've done 57 hard years of being me (well maybe 56.5 years of being me and 0.5 years "on vacation from me")

[April Rose]

I haven't had that conversation recently, since I am alone now, but after reading this thread, if I am ever asked the "why?" question again I think my response will be as follows: "That's a really valid question, and I will try to answer it as best I can, but first, so that we have a context in which to proceed, can you explain to me why you are the way you are."

Who knows; they may even be able to do it. At least then I'll know what the ground rules are.:heehee:

[ShirleyN]

You know, I'm not married yet but this would absolutely be a concern for me. Speaking from personal experience, it's not really a "why I need to dress", but more of a "need to dress", if that makes any sense.

[jacypods]

We have had the conversation a couple of times, but finally just decided it was a fact. He enjoys it, and it's part of who he is, so how can we make it both enjoyable and guilt-free for him, while making sure I'm not uncomfortable. I mean, I love hockey, it's just who I am, and he has to accept that. In the end it's not that different. We all have different things that make us feel happy or fulfilled or at peace and it's sort of impossible to track down the "why" of those things. My feeling is that everybody should be allowed to love what they love, and people in relationships just need to be open to finding a happy medium in the expression of our personalities.

[cindylouho]

Aside from the myriad of underlying reasons why we desire to dress, at the root isn't it simply because it helps bring out the woman in us? My wife noticed the second I'm dressed I walk differently, I always knew that but always thought I was trying to walk that way.

[Leslie Mary S]

On the subject of hip sway, I wanted to know so I found a nice explanation at. https://www.docunlock.org/youtube/hipsway. with graphics. There is a real reason for the hip sway.

I also saw a great talk on the show called "TED" by Johann Hari about depression and anixiety. I think we crossdressers use our dressing as one of his "COW"s. Give it a listen. It is NOT about cross dressing but it is about depression and anxiety. Please give a listen.

[RADER]

It seems most folks are saying here "I do it because I enjoy it" or some such variant. I think that's an excellent reason for doing something.

You hit the nail on the head. I dress because I Like it. I wear a skirt around the house every day. I would not have it any other way.

[Micki_Finn]

If say she is afraid of where it is going and I?d say that is a completely legitimate fear. You told her that you like the clothing for the comfort, but by your own admission, you don?t feel comfortable presenting without makeup and bra and the whole deal. Makeup and bras are NOT comfortable so your wife has obviously seen through that excuse. So why DO you like to crossdress? If you can?t articulate it, then maybe you don?t understand it, and if you don?t understand it, how can you ever say definitively where the limits and ends are?
Maybe it?s time to reflect on why you enjoy it and what you want to get out of it.

- - - Updated - - -

If you ask me, “because I like it” isn’t a REASON. Of COURSE you like doing something you’re doing voluntarily. That doesn’t answer the question because then you can just replace the original question with “Why do you like crossdressing?” Is that really a different question than “why do you crossdress?”

[SaraLin]

Micki_Finn, you're right in saying that makeup and bras aren't comfortable - and in a sense, you just might be wrong at the same time.

How?

Well - I agree that PHYSICALLY, bras, girdles, pantyhose (the list goes on...) can be quite uncomfortable.

So why do so many of us do it?

I'd like to suggest that for some of us (I'm including myself in this group) - we find an EMOTIONAL sense of comfort from wearing feminine things. I think that THIS is what many of us mean.

I know that for myself, I feel much more "at home" when I'm not wearing anything from the men's wear department. I get a sense of "comfort" when I'm dressed that I just don't get from a t-shirt and jeans (my man costume). It's got little to do with physical comfort though. For example, I'll find myself complaining about my nighties tangling around my legs or bunching up underneath me in bed - but I wouldn't dream of taking them off, or wearing men's PJ's instead. That would just feel wrong somehow and I'm "uncomfortable" wearing them.

Now, if I'm asked why I like it, I guess I could always counter with "Why do you like onions? They're nasty!" IOW, different strokes, and all that.
I am who/what I am. I can't change that, and frankly, I've stopped trying to.


I hope I'm making sense - at least a little. It's hard to put into words sometimes.

[MiniRock]

The problem, it seems to me, is that most cross dressers do it as a turn on. Which they know sounds a bit dodgy. Especially as it's kind of self-sufficient. So they try to give their wives an alternative, more palatable explanation. Even saying I don't know is a bit of a cop-out. I've told my partner that it has a sexual side. And she's seen me starting to get aroused if I try on something new. But fortunately, she's open minded enough not to care. But I think she might be quite unusual.

[MonicaPVD]

Because I like women's clothes because I like to look like a woman because I like to feel like a woman because I like to be treated like a woman because I always wished that I was a woman.
I will never be a woman. So I do this.

[Geena75]

As stated, there are a myriad of 'reasons' or just things going on when I dress. There is definitely a sexual, or fetish aspect of it, but if that were the defining part I would probably dress more often and for shorter periods of time. There is the curiosity aspect of it, discovering what a woman might feel like dressed up pretty, but then a couple times later curiosity would be satisfied and done. "I enjoy it" would prompt the response "What do you enjoy about it," and back to square one.

Probably the defining point for me right now is being someone else, or at least appearing to be. I am consistently amazed at how little resemblance there is between drab me and Geena (owing a lot to wearing a face mask, I'm sure), and it's both stimulating and relaxing to do it. It would also explain why I would want to venture out and about dressed up -- it sort of certifies that I appear to be someone else. I recall someone meeting friends when dressed and having to announce that "it's me," and that struck a chord inside me. It's fun to not be me now and then.

[JulieC]

I don't dress to get a turn on. I can't say that hasn't happened as a result of crossdressing from time to time, but it's not the reason. Certainly as I've aged, it doesn't have much of an affect in that category anymore anyway. Yet, the urge to crossdress is as strong as before. It's not the reason.

I don't crossdress because I like to crossdress either. It's not the reason. It is a benefit of crossdressing, but it's not the reason.

For me, the reason is there is a feminine aspect to me that demands expression. If I don't express it, over time it impacts me in negative ways. I need to crossdress as it is a part of me that needs expression. I need to be able to feel and/or look feminine at least partially in my appearance. This is why women's slacks/jeans/leggings don't really do it for me. It's dresses and skirts for me. This is why flats don't really do it for me. It's heels. Same for socks as opposed to hosiery, or plain underwear as opposed to frilly underwear, etc. I need to feel it, I need to see it, I need to have that expression of being feminine. That is the reason, and it's the only real reason. Anything else I get from it is a benefit, but not a reason.

[Joanne108]

My why was that I enjoy it. I go through a slow transformation from my male look to that of a totally female look. It blows me away that I can in less than 45 minutes look just like a woman! And I love it.
She said, Okay, but I still don?t get it.
I said, You get to be beautiful all day every day. I get to be beautiful about less than ten percent of that time. It?s rare for me so I do it and look forward to the next opportunity.

[Marissa Q]

The question Why is often a shame-inducing question as in when parents ask their child why did you hit your brother, or a wife who disapproves of her husbands drinking asks why do you drink so much? There is usually no satisfactory answer as the person asking the question really is just expressing their disapproval.

Possibly. But not providing a satisfactory answer is often dissimulation; it frees the subject of any real responsibility since the real reason behind an action is never revealed. And it is often this dissimulation that drives an SO/wife/parent to despair.
There are always real reasons behind every human action.



The problem, it seems to me, is that most cross dressers do it as a turn on. Which they know sounds a bit dodgy. Especially as it's kind of self-sufficient. So they try to give their wives an alternative, more palatable explanation. Even saying I don't know is a bit of a cop-out.

You're right. "I don't know" is almost always a cop-out, generally associated with childlike behavior. It is, prima facie, an avoidance of the question. Even worse, it has no therapeutic value for the person uttering it save to defer a reckoning with the self.



I've told my partner that it has a sexual side. And she's seen me starting to get aroused if I try on something new. But fortunately, she's open minded enough not to care. But I think she might be quite unusual.

Good for you! And she might not be unusual at all given that you offered her a reasonable and believable explanation that she can understand and even identify with.

[1Ladyjade]

Something my wife has asked since that day. In conversations before I said I liked the sensuality of the femme clothing. Since I made this original post she asked if you like the feel then why all the shapewear and makeup. The feeling is lost behind the shapewear and makeup serves no feeling. So there is more than just sensual aspect of cross dressing. I am trying look more feminine. So she is struggling with the you sure your not gay or wanting to transition. No I am happy in my man skin. I just enjoy putting on a dress and being free for a little while.

[Jessica Secret]

The simple answer for me is I love wearing lingerie and expressing my inner woman. My boyfriend and I had that conversation while we were still in the dating stage many years ago, he asked out of curiosity and made it clear that he was accepting, supportive and encouraging of me in that regard. I told him I just loved fem clothing and wanted to feel like a woman. When we got into a relationship I told him that I wore romantic lingerie to bed almost every night because I loved feeling feminine at bedtime. Needless to say he was pretty happy and excited about that and couldn't wait to actually see me wear it, which he was beyond excited when I did that first time.

[britskye]

I'm still coming to terms with the "why". Some of it is the softness of particular clothing, some of it is the variety and cuteness of women's clothing. There's likely something else there deeper, but i'm not sure exactly what that may be quite yet. Whatever it is, i'm hoping to continue embracing it as soon as current relationship status makes that opportunity a reality.

[Stephanie47]

I out my two cents in at #9. I'll throw a thought out for consideration. If anyone has read some of comments over the years, there is one that is applicable to this conversation.

My counselor, who is also an Iraqi deployed veteran, expressed her opinion that each man and woman has dna of the opposite sex within their dna profile. In some it is greater than others.

If I accept her premise, it does make some sense in my life's journey. That analysis may answer the "Why." Then the question arises on how a guy deals with expressing or suppressing his feelings when they arise. Once I accepted myself, I still have to deal with those around me. Their problem becomes my problem.

[sometimes_miss]

My current understanding is that crossdressing is basically one of the ways that a person who suffers from the cognitive dissonance of having a male body, while having a mind that identifies itself as female (for whatever reasons; genetics, hormonal caused, conditioning, etc.), is able to diminish the amount of psychological discomfort experienced, in order to allow him/her to accomplish the other tasks which other people are able to do without the sometimes almost constant mental thought interruptions caused by that dissociative state.
Of course, because most of the people in our current society see any type of gender 'abnormality' outside of the standard binary as the only acceptable one in our world, in a mate to be such a complete turn off, that explanation isn't something that anyone would want to tell a current or potential mate.
So most of us are stuck without a mate who truly finds us adorable as we truly are.
So at this moment in time, 'I don't know' is likely to be the only potentially satisfactory option we have, as the truth would be almost certainly the ending of the relationship.

[DianeT]

The feeling is lost behind the shapewear and makeup serves no feeling.
The feeling isn't lost in the shapewear, unless you cover all your body, and wig, shapewear and makeup are very effective for attaining a feminine look, look is important to many of us. Makeup is also feeling, it is very sensual to apply and it is also an act of pampering yourself, which sends good vibes in my opinion, not mentioning honing your artistic skills.


So last night she asked why do I like to cross dress.
As for the why, I have searched a lot, with the help of my wife too, and while I don't have a definitive answer, I learned a lot about myself and came back with several explanations.
So, I don't think the why is out of reach like some said. But I think that to be successful in your search you have to settle for a level of accuracy. You'll know which is right for you because past that point, you will notice that you tend to come back with more questions than answers. This to me was the sign that I was beyond the point in question.
It's a bit like Mandelbrot measuring the coast of Britain. The more accurate you want to be, the smaller the rule you'll need to use, and the resulting measure will increase indefinitely. You must chose a reasonable rule size and stick to it.
It's also like understanding the weather. Meteorologists use models splitting the atmosphere in cubes of a given size. The smaller the cubes the better the precision. But the required computing power quickly grows exponentially and you have to draw the line somewhere, where the weather predictions remains useful and the cost under control**. They will never get to the real truth of how the weather works, it is far too complex and chaotic and all the computers in the universe wouldn't suffice. But they can make a coarse model that does useful predictions.
Likewise, we can't expect to explain the inner mechanics of a human brain with a hundred thousand billions of neurones. And neither can psychiatrists. But like meteorologists, we can try and make a coarse model of it, inject some motivators and stimuli and see if we get interesting deductions out of it, for example a taste for some aspects of crossdressing. We can then play with our new model and try to deduce a thing or two. If we land a deduction that is confirmed by facts then we have a model that reasonably works. If we don't, rework the model at the light of the new findings. I have a model for my crossdresser brain. It's not perfect, but it gave some interesting results already*. It's a work in progress, but I also know that I will find the limit of this exercise at some point, and I will have then reached the optimal rule size for measuring my own coast.

*I also tried a tentative model for some of us, to try to explain the pink fog, or the claiming of heterosexuality despite getting intimate with males (did a thread for this one), all this with more limited info, and consequently less reliable results.

-- EDIT --
**Also, at some point, you will become precisely inaccurate instead of coarsely accurate. Like when encoding audio or video with two high a bitrate, you end up encoding noise.

[BrittanyB]

Diane,

I never expected to see fractals and non linear dynamics applied to crossdressing, but I like it! :)

My "model" is not so complex and therefore doesn't run the risk of being "precisely inaccurate". It took a great deal of time, though, to understand this. For decades I didn't even attempt to understand it. I was too caught up in the shame and guilt which made any attempt to understand it an exercise in masochism.

Fortunately, after being discovered by my wife of 17 years at that point, my wife encouraged me to "try" to understand it. I wrote "explanations" as best I could progressively over time. The first was far too simple..."it's similar to a hobby in that I enjoy it and I strive to be better at it." Later efforts landed on a reasonably correct, but somewhat unsatisfying :"it's an escape from the stress of life, a euphoric escape that brings feelings of calm, completeness and joy."

The real breakthrough in this endeavor, though, was when I really tried to get in the head of my younger self when I first started to wear my sister's clothes and as I progressed to wearing my sister's and mother's clothes. I explored how I was feeling, what was going on in my life at the time and the "my story" myth that we all have to some degree.

My mythology went something like this: I was a strong, smart boy who became rebellious and self-destructive after my parents' divorce. Eventually I shed the rebelliousness and became a thoughtful, empathetic, and successful person.

Much of that is true, however, a more precise narrative would be that I was a smart and sensitive boy who was deeply impacted by three simultaneous and chronic life changes:

1. My sister, to whom I was very close until I turned 8 and she turned 14, started to reject me as she entered high school, a perfectly natural and common thing for a young girl entering that phase of life.

2. My mother's affair and subsequent divorce during the same period resulted in my mother changing from a doting, loving mother into a self (and man) obsessed person.

3. My sister became clothes and makeup focused and she and my mom became close through makeup, clothes, chatting away while doing their makeup, often while wearing pantyhose, slips, bra.

Through makeup, hair and clothes, my sister and mother now shared a closeness that was unavailable to me. I was just the young boy neither understood or tried to understand while wanting desperately to feel the warmth and closeness I enjoyed with my mother and sister prior to this period. I think it's reasonably accurate to say that when I first put on my sister's sweater poncho, I felt closer to her. It reminded me of her and how close we were. She used to wear that poncho a couple years before when she would take me everywhere with her.

Then I started trying on my mother's clothes, starting with a light green, wool, houndstooth skirt suit, and matching pillbox hat (think Jackie O) that she had stored in a garment bag in the basement. It made me remember the vibrant, smart, playful, loving mom she used to be.

The feelings I get today are so very similar to my memory of the feelings I had as a little boy when I dressed in their clothes. There is, of course, more, but it is less interesting and relevant to "why". But this is the important part, there was no way I could have begun to understand this if I had not worked to accept it and for that I have to thank my wife. Otherwise, the effort, though painful as it was, would have been a highly masochistic endeavor.