Jealous of the woman walking down the street

I saw a woman this week walking down the street in her work clothes and it brought up a number of feelings.  To start with I will describe her, she appeared to be in forties and medium build with C or D breasts and wearing a brown skirt and blouse, nothing flashy and it wasn’t that she was incredibly hot she just looked good and put together.  This caused a conflict within me as she was attractive and as a heterosexual male I checked her out but as a crossdresser I also checked her out in a different way.  The first part is obvious the second is a little different because as a crossdresser I also looked at her outfit and how she looked likely more like how another woman would look at her, admiring her outfit and how she pulled it off (I wonder if that is how lesbians look at women?).  But also as a crossdresser I had a feeling of jealousy in that I would likely never be able to look like that nor am I likely ever going to be able to wear that to work.  While I could easily find out what it is like to walk down the street wearing a skirt, blouse, tasteful heels, pantyhose, and carrying my purse on a late summer day I would be doing the same thing knowing that because of my frame and build I would be read nearly instantly.  In order to achieve a convincing look I would need to be wearing a corset, breast forms, and padding on my hips and butt and even then it would be pretty hard to pull it off.  It made me realize that without hormones, surgery, and perhaps some magical powers I will never be able to walk down the street and feel even remotely the same as she did.  My own breasts in a bra as they sway slightly and the feeling of the blouse against my slight hourglass figure as I walked, or the skirt moving against my wide hips and larger rear as my heels click on the pavement.  My long natural hair to my shoulders is one thing I could likely do but to be honest my personal style does not support that.  I will never know what it is like to live like that day in and day out, which is sad but also the reality of the situation.

The only solution to this is of course the previously mentioned hormones and surgery, which is not a path I would like to go down.  It is at moments like this that I wish I was transgendered and felt like I was a woman and would be content living my life as such or not be attracted to wearing women’s clothes while recognising that being transgendered is not living a charmed life.  I am guessing many crossdressers are caught in this middle ground where we are just trans enough to be compelled to wear women’s clothing but not trans enough to do anything permanent about it.  At the very least it would be nice to be a slightly less masculine man as I am above average height and size for a man making buying men’s clothing a chore forgetting about tasteful women’s clothing.  If I was less masculine I could at least look feminine and be able to get a glimpse into the everyday life of a woman and closer to the feeling of walking down the street.  I typically like to offer a positive thought for me to work from in these posts to be honest this time I don’t have much, that woman without knowing or intending it brought up so many conflicting feelings.  I truly do love women and their clothes and I typically do not see crossdressing as an affliction to be cured but there are moments where it would just be easier to be average.

There are certain things we will not be able to experience in our lives and the fact is that I will never know what it is to be born female and live my life as a woman.  While I could live my life as a transwoman it does not hold any appeal for me.  So I will live my life as man who likes to wear women’s clothing and be content in the knowledge that no one truly knows what it is like to be someone else.

Ever had these conflicting thoughts of attracted and jealous?

9 thoughts on “Jealous of the woman walking down the street

  1. Nice Post.
    Very much had the same feeling. What most struck me of my this at the time of my revelation was the sheer sexual power of this woman, confident in her outfit, strutting almost, and holding most of the men in the vicinity in her thrall.
    However, we are not the only ones with body dysmorphia, and suspect that inside she was thinking “my bum’s too big in this dress, my mascara is smudged, why are all those men staring so”.
    So it goes 🙂

    1. The sexual power is a complex interplay of looks and personality as you seem to state. I wonder however if it is made more pronounced for us with the additional level of “I want to be that, even just for a bit”?

  2. Excellent commentary. We, as happy, hetero CDs do often deal with the conflicting issues of envy and acceptance. I will never flip the script but there are times when it would be nice to truly be able to see things from the other side of the gender divide.

  3. Hi Jess, I’ve only just found your blog whilst searching for ways to deal with my hairy legs and bits. I’ve read a couple of your posts now and see all of me in you. I’ve dressed for years since I was a small boy, I’ve purge clothing before, but came to realise it’s better just to store it as I come back to it every time, and the outfits remind me of good times.
    Now in my late forties, the urge is so strong, after a break for kids and work commitments I’m back for more wanting to dress fully, although as with you, I bigger frame and masculinity I’m going to struggle to pull it off.
    I liked this post as it sums me up very well, I’ve gone through my whole life, every day feeling like this. Past girlfriends and the wife have all accused me of checking out girls thinking it’s sexual. Some it it is there’s no denying it, especially went they’re dressed well and full of confidence. I’m always looking at girls, ladies in the street, or magazines etc I’m checking out their outfits, how they carry themselves, their confidence in their choice out outfit. I love looking at their footwear, high heels or boots the choice of the heel design. The tightness of a pair of boots on the calf is crucial to me, I admire everything even the choice of coat or jacket.
    When I’m admiring them I’m thinking wow great outfit admiring their confidence(which they probably take as second nature). I’m thinking I’d love to wear that, thinking I’d wear that dress, but with boots not shoes and probably a nice hat?!?! Then I’m think wow could I be her could I swap places would I be happy with her lot, her boyfriend etc……I’m dreaming now I know.

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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