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Thread: First Time Wearing High Heels?

  1. #1
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    First Time Wearing High Heels?

    Just curious. I have read and seen pictures of guys wearing heels for the first time and the troubles they have adjusting so as not to stumble.

    What was your first experience? When I first started dressing in my early teens I took to wearing 2" and up like a duck to water.

    Was anyone else a natural?

  2. #2
    Aspiring Member MissDanielle's Avatar
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    All I ever wore were 2 inch pumps but I don't recall struggling to walk in them.

  3. #3
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    I have tried many times; I even borrowed my wife's walker to help me.
    Just no luck at all. My ankle just does not want to bend so much, But I
    do have a pair of flats and a pair of 1 1/2"
    I can walk in those for a short time.
    Rader

  4. #4
    Gold Member Maria in heels's Avatar
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    When I was little, my stepmother had these beautiful pair of platform black pumps with a 4 inch block heel....thats where it all began

  5. #5
    Miss Conception Karren H's Avatar
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    Think I was like 3. Lol. At least that's what mom told me. Apparently I didn't have any problems because later on in life when I started buying my own, I took off running and never looked back. I attribute it to decades of playing ice hockey building up my ankle muscles.

  6. #6
    Member Tara Rushing's Avatar
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    Although I am no graceful swan in heels, I didn't really bobble or fall. I guess it helps that I've worn Cowboy boots for so long (of course they have a heel but not 4" LOL) and had the basic heel to toe motion down beforehand.

  7. #7
    Exploring NEPA now Cheryl T's Avatar
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    I first wore my mom's (about 3") when I was like 9 and looked like all the videos you see of little girls dressing in their mom's clothes. I tottered and teetered all over. Then in my teens I bought my own first pair of 3" pumps and they felt like flats to me. It was riding a bike, I just never forgot how...
    I don't wear women's clothes, I wear MY clothes !

  8. #8
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    Never had a problem when I first started. I bought a pair of 3" strappy sandals and that was.it

  9. #9
    Lost in Heels AnnaMarie's Avatar
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    Never have a problem and I like high ones (see my profile pic). Found the easiest way to balance is to sway the hips when you walk - it does help!

  10. #10
    Gold Member ~Joanne~'s Avatar
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    I would say wearing heels came natural to me, almost borderline scary natural lol. I may not be totally graceful in them due to hip movement differs between the male and female body but i never really wobble in them and I have never fallen in them.
    Flip Flops were made for Beaches & Bath Houses, We have neither in 2017. Lose the flip flops!

  11. #11
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    I picked up a pair, I think they were 2 inches, at a thrift store. This was when I first started dressing. I had no problems at all. Being used, may have made them easier to get used to.

  12. #12
    Gold Member Jaylyn's Avatar
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    Use to wobble around in moms when I was a child. I have never had a problem wearing them. I also grew up in tall heeled bronc riding boots. I now have a pair of Six inch, and Four inch heels. I really think it's all about getting the calves in shape and the ankles stretching a bit. I do the elliptical almost daily and have begun to do it on the balls of my feet. I've found this strengthens the calf, heel and ankle. I can almost run in my heels like "Charlie's Angels" used to... Well maybe not as graceful....

  13. #13
    Member SHINY-J's Avatar
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    I took to wearing heels very quickly. I didn't start low and work my way up either... I started with platform heels and boots right away! I don't own any ladies footwear that aren't high heeled platforms and never have.

  14. #14
    Silver Member Tina_gm's Avatar
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    I think that a lot of guys who wear heels and are not CDers, For a joke, dare, hh race and look like it is the hardest thing to do, are acting out on this a bit. Not saying I was really good at it when I 1st wore them, but I do not remember being so awkward that I had a hard time standing up.
    Chickens should be allowed to cross the road without having their motives questioned

  15. #15
    Member Tara Rushing's Avatar
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    Perhaps part of our "natural ability" (as it seems the theme of the thread) has to do with the fact that we had all probably rehearsed/envisioned/fantasized about it well before we did it and probably many times at that. In sports visualization is a powerful performance technique so it probably applies on some level here.

  16. #16
    Member Allison_CD's Avatar
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    Have had my sexy Red 5.25 for about 2 months and can barely walk across the room.
    Gals make it look so easy. OK in my 2 inch heels.

  17. #17
    Neanderthal in nylons Julie Denier's Avatar
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    I started clomping around in my mom's shoes as a tot. When I started crossdressing seriously decades later (about 5 years ago), I took to heels pretty well and have no problems walking in heels up to about 3 inches, maybe 4 if the shoe is well constructed and well balanced.

  18. #18
    Sixty Something Gypsy Sam's Avatar
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    Just the fact that they look so sexy, and when trying them on the heightened sexuality of wearing them triggers a arousal. Navigating in heels becomes a blend of desire to sexy, and liking what the reflection in the mirror does for a female presentation. Still learning how to descend stairs in 3" mules, but sure do enjoy strutting across a room.

  19. #19
    Senior Member Christie ann's Avatar
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    I remember slipping on the tile floor in the grocery store. So much for being subtle.

  20. #20
    A lady in the making..... Erica Marie's Avatar
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    Odd, I commented to a friend just the other day how natural it is for me to walk in heels. 2", 3", 4" honestly doesnt matter. Almost like a sign from above.
    Erica

  21. #21
    Member Allison2006's Avatar
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    The first heels I ever wore were a pair of my sisters wedge sandals, when i was about 16. I think they were 3-4 inches and never had trouble walking in them, although wedges aren't as difficult as other heels. Never had trouble with other heels either though, and its rare that I buy a pair with less than 4 inches.

  22. #22
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    I was in secondary school at the time, and still presenting as a boy in a dress. The heels were my mother's, and I could still somewhat fit into them. I walked much slower than I usually do, and it was more awkward than anything.

    Fast forward to after graduating high school. A pair of unwanted stilettos from the storeroom were the highest I ever went. Still a little daunting wearing them, but posing in them (and stockings, and a mini skirt) was beyond sexy. Walking in them was still okay at least.

  23. #23
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    I think walking in heels was easy for me, I remember wearing my mothers heels at about six years old, have been doing it for the past 66 years, heel heights are so different, heels with no platform are the hardest to walk in as the heel gets higher, 3 inch and under are very easy for most people to walk in, above that, it takes practice. the practice is just wearing the heels, not for 30 minutes, but for 8 hours or longer. Your calf has to a just to the new angle of your foot and this takes some time (practice) to get use to with out calf hurting. Platforms, subtract the height of platform from heel and you will get the real heel height. You have to wear heels very regularly to keep leg muscles from not hurting after a long night out. Marshalynn

  24. #24
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    Hi Diedre, At around age 4 I would get into my moms heels, and the rest is history.
    Just like the GG's I learned at a very early age and after 69yrs. of walking in heels it's
    just second nature to me, Dressing everyday and wearing 4" or 5" heels just seams so natural.~~......
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  25. #25
    Gold Member Diane Smith's Avatar
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    I think the exaggerated tripping and stumbling when men first wear heels is largely a media trope, like the overused bullet ricochet sound or cars bursting into a ball of flames after they crash. People have seen it on screen every time a man tries on a pair of spikes ever since "Some Like It Hot," maybe before, and so film and TV directors (and often the subjects themselves) repeat it endlessly because it's just part of the cliche now. Actually, most people (male or female) do reasonably well in heels the first few minutes, after maybe a few awkward steps to get the feeling of them -- it's only after they've worn the shoes awhile and covered some distance in them that the long term aches and pains begin to affect the speed and grace of movement.

    - Diane

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