What sort of woman would I be?

After my last post about seeing the woman walking down the street and me being jealous that I would never be able to look like her or experience it like her I started to think about what sort of woman would I be?  I don’t mean if I was to transition over a number of years or wake up tomorrow as a woman but if I was born a female.  It brings up some interesting questions such as would I be a mirror image of myself? A feminine woman with a tom boy side?  Would I be attracted to men with a slight interest in women?  So a few compare and contrast points.

Wake up as a woman

First I should deal with a fantasy we have all likely thought about at one time or another and that is that through supernatural or sci-fi means I wake up as a woman and everyone assumes I was always one.

Always been a woman

Here I am assuming that I was born female and my life followed a similar course.

Underwear:  Waking up tomorrow as a woman I think I would likely be slipping on all the prettiest of black lingerie.  Bra, Thong, Garter belt, Corset, Slip, and fishnets just to take it all in.  Oh look at all the fun lingerie! Underwear: Supportive bra because I have to wear one to keep the girls from going all over wondering why I have breasts since I’m not breastfeeding, I love them and everything but such a pain.  Likely bikini panties because there is no need to have the thong wedgie all day.  I really should wear my sexy lingerie more often but what is the point?
Clothes:  Tight dress or short skirt with a low cut top.  Maybe some tight jeans and a tank top. Clothes:  Flattering but comfortable.  No need to have my body on show the entire time.  I like being a woman but all the styles is tiring and why does everything have to show off my cleavage?
Shoes: Sky high stilettos Shoes: Laces are good, or low heels.  No need to walk around on stilts all day but on occasion maybe some extra height.
Make up: All of it Make up:  Who needs it?  I suppose for a special event or if I looked terrible.
Nail Polish: Deep red to match my lipstick Nail Polish: It chips and wears off to easily, I am not just enough of a girl to keep redoing it aside form special occasions.
Jewelry:  Hoops or something that gives me that jingle jangle all day.  Tasteful necklace to draw attention to my cleavage, you know you want to look. Jewelry: Sensible earrings so I don’t have a jingle jangle beside my ear all day.  Everything else will just get in the way and necklaces only make people look at my cleavage
Pictures: Selfie time! And not only innocent and glamour ones but the ones you shouldn’t take ever; even for snapchat Pictures:  Occasional selfie for social media but likely to take pictures of places and things as opposed to of me.
Weekdays:  Go to work with the most feminine underwear and business clothes.  Nights are out experiencing life or in experiencing self. Weekdays:  Go to work and then come home and walk the dog, watch Netflix, hang out with friends may be a night out here and there.
Weekend: Party time.  Have a new body to try out and it seems unlikely that I would be spending a whole bunch of time alone.  Men?  Women? No clue but keeping my current orientation women, with toys. Weekend:  Read a book, walk the dog, drinks with friends, housework, and maybe someone for personal comfort but if else fails there is always a battery operated option.
When would I be ready to go back: Are you kidding I get to play both sides how often do you get a chance to do that?  The getting periods thing would be tiring but dude I’m not a dude anymore!  I want to make sure I can go back but if not look at all the pretty clothes I have!  Though I would not switch without a reverse option. Would I want to switch?: Men have it so easy, no periods, no bra, and people not judging them on everything they wear just a lot of it.  I wonder what it’s like for them?  I suppose I could always get a strap on.  Men’s clothing is comfortable and relaxed, good thing I’m a woman and no one looks at me to strange for wearing men’s clothes now and then.  Why aren’t women’s panties as comfortable as these boxers I have on?  Do they actually use the flap?


I suppose if I had been born female I would have had the experience of being a girl, a teenage girl, a young woman, and a woman.  Since the vast majority of crossdressers are male for many possible reasons I doubt I would be chomping at the bit to wear men’s clothes, but if I did it would be more socially accepted anyway.  I identify as heterosexual and the majority of people are straight so it reasonable to assume that I would also be straight, I have thought about men but they really don’t do it for me.  Would I be married to a man?  Would I be bi sexual? Even if I were a lesbian it seems likely I would have a boyfriend at some point and had kissed a man or more.  Maybe I would be a mother at this point.  Would I have the same joy out of a simple pair of panties?  The only way to explain some women’s underwear is that it makes them feel feminine so I suppose I would still take some joy in lingerie, though it wouldn’t be a forbidden fruit of the loom.  Would I have the same degree?  It seems likely I would have studied different things?

The end result is that while we as crossdressers have all likely daydreamed or fantasied about being able to experience life on the other side.  (What would it feel like to be a woman?  What is it like to have breasts and feel them in a bra?  What is it like to have sex?  Would I like it more?  Would I want to stay a woman or would I want to be a man again?)  We also recognize that if we had been born female it would all be normal and to a point mundane.  Yes being a woman and always being one would have different perspectives and experiences but much of the same things would happen as I would likely have a job, pay bills, have experienced love, experienced heart break, and had questioned my sexual and gender identity.  While we all experience these things and some people even say sex and gender is not nearly as important as it used to be I would expect that with all things being equal experiencing gender as a woman would result in a very different person today.  Even if everything else was the exact same and we lived in a genderless society experiencing sexuality as a female would have wide ranging impacts.  I would not be the same person I am today not only because I had a vagina but because having a vagina would alter so many other aspects of my life and the choices I would have made.  I will never know of course what the everyday mundane life of a modern woman is to live but I like to think I would have made a good woman had I come out that way.

So if I were given the chance to flip a switch and switch from male to female and have the world think it was always that way and nothing else in my life be different would I?  I would give it some serious thought and would defiantly take a test drive if I had the option.  If it was an all or nothing chance and I would never be able to go back I think I would likely turn it down, after all I like being  man but I would always be left wondering if I made the right choice.  Just as well that it is a choice I will never face.

Thoughts?  Have you ever wondered what your life would have been if you had been born female instead of male?

3 thoughts on “What sort of woman would I be?

  1. Great post. Lots to ponder.
    As for me I love my wife and children and am relatively happy as a guy. I do wish I could take the occasional walk on the other side.
    As a kid l liked comic books…mostly Superman. I wonder if I see my dressing as being my secret identity.

    1. Funny thing is that I have a post describing my history of dressing that i have been working on and use the exact same analogy of superheros and secret identities.
      That’s two posts in a row that you have described something that I am working on for a future post.

  2. I have to wonder about the results. . Consider, my current thinking. Most of us that have been crossdressing for any length of time have given that idea some thought. And without a doubt, it is fascinating. .But here is the problem . . .

    What sex do you choose to love? True women much more often than not, are straight, not bi, or lesbian…YET most crossdressers are also straight. In theory, they want a woman’s body, but yet, they want a woman for a lover. . .There is a significant disconnect.

    I suspect that this disconnect tells us something important about ourselves. . . Couple that with the all to common feelings of those that have had MTF surgery, (regret) and it would seem that crossdressing is at its core a type of female envy. .

    I have no problem as a 44 year crossdresser admitting that is most likely what is occurring in my case. I’d love to have boobs. . I’d love to have a more feminine face and perfect legs. . but NOT all the time. I think we all have to admit, there are times when its damn nice to be able to take off our boobs and bra and go about as a man. otherwise, we would be transgender.

    I have been crossdressing since about 72 or so. . underdressing regularly since 80. I probably wear a bra and forms under otherwise normal male clothing 70% of the time. BUT I still don’t want to BE a woman. . Yea, I have thought about breast implants. . but not having the twigs and berry’s shaved off.

    Nor does the idea of being in love with a man do anything for me.

    We want the trappings of womanhood. . the frilly clothes, the makeup. . the chance to destress to feel soft and silky clothing against our skin. . to break the conventions of social mandates that force us to be “men.” Just not all the time.

    I realize I don’t speak for everyone. But I suspect that for most “Crossdressers” this is a correct observation. As I said, otherwise we would be true transgender, and accordingly have the desire to fall in love as a woman would, with a man. . The idea that Transgendered (MTF) women would have such a high prevalence of lesbianism really streatches the bounds of believability.

I love to hear from people who read my blog, even if your not in agreement with me. Your comments may spur me on to write something else so please comment.

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