5 Questions Crossdressers Dare Not Ask Themselves

crossdressing questions and tips

5 Questions Crossdressers Dare Not Ask Themselves

Without a doubt, the need to crossdress is something every crossdresser is born with; it’s an indisputably built-in part of us.

For most participants it brings great pleasure and greater awareness of the differences between genders. It also provides valuable time for many men to escape from the hurly-burly of the modern world and relax, letting their feminine side rise to the front and watching the world go by from a different perspective.

Most crossdressers are pragmatic enough to know that they can never ever give up this need, this want, this overpowering desire to crossdress. Even though some of our community purge (an awful word!), they are likely to start crossdressing again, almost as sure as the sun will rise in the east!

There are those who say crossdressers are delusional, in their En Femme dress or skirt and top, that they lose sight of reality when the so-called pink mist descends on their thought processes. No, sorry, I don’t agree. We are as sane and reasonable as the next person. It’s just that we do, I must admit, have the tendency to avoid asking ourselves some searching questions about our dressing—to which, perhaps, we don’t really want to know the answers!

What are these five questions?

  1. If crossdressing, for many, is simply about wearing women’s clothes because they enjoy the feel of the fabrics, the sensuality of the silks, the swish of the En Femme skirts and the variety of colors and styles on offer, then why do so many crossdressers feel the need to wear bras and breast forms and figure shapers, wigs and makeup, to give themselves the complete appearance of a woman? Is it, therefore, not the latent desire to be female which drives them to dress, not their admiration for the clothes?
  2. If crossdressing is frowned upon and misunderstood by the vast majority of the world’s populace (despite recent great advances in public awareness in the media and elsewhere), why do so many crossdressers offer themselves up for taunts, ridicule and even the threat of physical danger, just by going out and about to show themselves to the big wide world when crossdressed? Are we all masochists at heart?
  3. If there were no negative repercussions with family or job, or no monetary concerns, if most crossdressers had the chance to live and present as a female full-time with no repercussions, would they really do it? After all, many of us long so much for the times when we can be women that to be full-time with no hassles attached would seem to be the ultimate goal, right?
  4. On the basis that most crossdressers all travel on a very similar crossdressing journey to each other, are they not all moving towards the inevitable day when finally there is no choice but to have gender affirmation procedures? In other words, will we all one day end up being full-time women?
  5. Why does dressing like a woman, making our appearance as perfectly feminine or as convincing as we possibly can, temporarily alter the perceived sexuality of some crossdressers? There aren't many crossdressers who will say from the outset he is gay or bisexual—yet a fair number of our community are prepared to engage in relations with another man when they are crossdressed, aren’t they?

Food for thought, yes? I dare you to answer….

However, I have to say that I don’t for one minute pretend to have the answers to these questions, nor do I believe that they apply to everyone in our crossdressing community—just many of us.

I also know there are many crossdressers who are more than content to occasionally parade around indoors in their En Femme finery without ever having the wish to leave the comfort of their bedrooms or homes or meet others in the community, but I’m not one of them.

For those of you who feel similarly, what’s your take on these questions we avoid?


  • Susan

    I was a cross dresser for years, I remember dressing up in petticoats when I was 4, and "borrowing" my sister's clothes as a teenager. When I finally asked my self those questions I found the answer in changing my name and my legal status. I have been a woman forever, but legally for the last 7 years. And loving it. Dare to ask.

  • Paul/Gina

    Great topic and you seem to have hit the nail on the head in terms of the questions, here's my 2 cents!

    1) For me it's about how it makes me feel as I dress. Each layer makes me feel more and more "trapped" in my femininity. I love the marks the bra leaves later and each step brings me closer to the object of my desire; the feminine form. I shave my legs and underarms, I have my chest and brows waxed and mani-pedis are a part of my life; all are things women do to that I align with!
    2) I don't "offer myself up" to anyone. I seldom dress full outside my home in and out of the presence of my wife. I go out infrequently, it's not worth the "hassle" and looks I'd endure, I'm not close to passable. Besides, this is something I do for ME, not to meet society standards.
    3) No hassles attached? Yes, deal me in for that option! Emphasis on the word "option". I don't hate who I am and I live comfortably in the spectrum of my male and fem self, though as I grow older, I tend to be more fem in nature. I enjoy having the option, after all, I see many women wearing jeans and "shirts"…..I am jealous that they get to wear heels with those jeans! ;-)
    4) I don't believe most of us are on a similar path arriving at SRS surgery. In my mind I AM a "full time" female, Gina is always with me to the level I can possibly be. I wear panties everyday, bra on some days, a wisp of mascara daily and wear nighties to bed…..I'm getting what I need and am happy.
    5) In my fem mode I am drawn to and have had experiences with other CD's, though I am not drawn to men per se. I am not delusional enough not to recognize that the sexy CD with a bulge in "her" panties is a guy….I get it! But for me, there is a level of submissiveness that comes with my dressing and part of that is in pleasing someone, male or female. Admission of my BI-Sexuality is nothing I shy from; if two people can make each other happy and have fun together, I care not the "title" society places on it!
    Thanks for letting me share!!
    - G

  • William

    I know we all have a lot, or at least one major thing, in common. Never the less, I think there are some vast differences. Question #1 hits very close to home for me. I'm in my 60s and have been crossdressing as long as I can remember. It is only recently, however, that I've extended myself to full female transformations, including makeup, wig, jewelry, heels, dresses. etc. I can't say if it means I'm going to a new level or whether its simply that I have the opportunity to take things things further now that I'm retired. I've read that crossdressers seek to become the object of his/her own desire and in my case anyway, there is much truth to that. Question #2-Never done it and probably never will but I admire the hell out of all of you girls who do. Question #3-Again an interesting question. Since I am retired, grown children and a wife who is aware and at least tolerates my crossdressing, I theoretically could be dressing up all the time. Truth is, I still only do it maybe once a week or twice and even then, for no more than a few hours. As exciting as dressing up is for me, I am generally more comfortable conducting my life as a male. #4-In my case, not in the least. #5.-Another interesting one. I will say, the fantasy is very much there, especially when I am dressed up. But while I've been attracted to men in pictures/websites, I have never actually met another male that I am even remotely sexually attracted to. Go figure? I'm curious about one thing not mentioned here for me. As dressing up seems to involve a high level of masculine denial, is being cuckolded a common fantasy or is that just me? Anyway Kathy and SF, thanks so much for the forum.

  • Larry

    I can identify with almost everything u state. I guess the feelings we all have are more connected than I imagined.

  • MarieMarie Nicholson

    Not new, not shy, and hjave learned to ignore the ignorant among the species here's my take on Your questions: #1;for myself it the desire to be female and to represent myself as fully as possible, #2;most definitely not masochistic, i endure such insults because , as a person, have the right, and obligation, to be who/what i know in my true nature to be (my only exception to this is child molesters don't care what religion/belief/society, etc one claims there is absolutely no justification for harming a child) and while i no longer react with violence to such attacks, the recipient of my vicious tongue is usually sad they opened their mouth, #3; Without any doubt in my mind, go full time very next second of life and continue till the last second of life, #4; No , not always true. i personally know many CD's who would never consider Gender reassignment, #5; not true, based on clinical surveys by the National Board of Psychiatry, 80% of all crossdressers/transvestites are heterosexual men involved in either marriage or a monogamus heterosexual relationship

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