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Thread: The why do you want to cross dress conversation.

  1. #1
    Member 1Ladyjade's Avatar
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    The why do you want to cross dress conversation.

    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.
    If you buy Craftsman tools instead of DeWalt to match your nails. You might be a cross dresser.

  2. #2
    Platinum Member alwayshave's Avatar
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    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.
    Please call me Jamie, I always_have crossdressed, I always will, "alwayshave".

  3. #3
    Member 1Ladyjade's Avatar
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    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.
    If you buy Craftsman tools instead of DeWalt to match your nails. You might be a cross dresser.

  4. #4
    Super Moderator char GG's Avatar
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    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.

  5. #5
    Senior Member Jenn A116's Avatar
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    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.
    Jenn A --- nothing fancy, just me.

  6. #6
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    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

  7. #7
    Exploring NEPA now Cheryl T's Avatar
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    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.
    I don't wear women's clothes, I wear MY clothes !

  8. #8
    Silver Member Pumped's Avatar
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    I told my wife if she could figure out why we like to dress she would be a rich woman!

  9. #9
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    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.

  10. #10
    Senior Member Kris Burton's Avatar
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    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.

  11. #11
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    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.

  12. #12
    Resident Polymath MarinaTwelve200's Avatar
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    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".

  13. #13
    Aspiring Member Leelou's Avatar
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    Quote Originally Posted by Stephanie47 View Post
    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.
    Last edited by Leelou; 05-21-2022 at 05:23 PM.

  14. #14
    Senior Member DianeT's Avatar
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    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.
    Last edited by DianeT; 05-21-2022 at 07:36 PM.

  15. #15
    Senior Member April Rose's Avatar
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    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.
    I am a vessel of the goddess. Let me express my calling to a feminine life through nurturing love and relatedness.

  16. #16
    Member Mary Loo's Avatar
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    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.

  17. #17
    Aspiring Member NancyJ's Avatar
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    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
    Last edited by NancyJ; 05-22-2022 at 08:09 AM.

  18. #18
    Silver Member Leslie Mary S's Avatar
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    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?
    Leslie Mary Shy
    Remember this:
    You do not have to be a man to love a woman, or be a woman to love women's clothes on her or yourself.
    _________________________

  19. #19
    Another fine dress AngelaYVR's Avatar
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    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.

  20. #20
    Silver Member Leslie Mary S's Avatar
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    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.
    Leslie Mary Shy
    Remember this:
    You do not have to be a man to love a woman, or be a woman to love women's clothes on her or yourself.
    _________________________

  21. #21
    Member Mackem Sue's Avatar
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    Why? Heavens knows. I've stopped asking.

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

    Sue

  22. #22
    Member nancy58's Avatar
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    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.
    Nancy
    "If you are lucky enough to find a way of life that you love, you have to find the courage to live it." -- John Irving

  23. #23
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    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

  24. #24
    Aspiring Member Georgina's Avatar
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    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.

  25. #25
    Member BrittanyB's Avatar
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    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".
    Last edited by BrittanyB; 05-24-2022 at 04:21 AM.

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