Youngest male heelers

[high_55]

if driving around the city counts as in public, i was about 18, though i knew i liked heels, i thought it was some kind of a sexual game, walking in public i have done let's say about 2 years ago, not on crowded streets, but going out of my office to the car, as i like very much sandals, i think it is harder to conceal them when wandering around.

[EdwardianEra]

JNR, The two friends I took were a guy and a girl. The girl, Anna, already knew about my love for heels, so she was fine with it. Ryan, the guy, didn't know until Anna and I had dragged him into the Payless, and then he didn't seemed fazed by me trying on women's shoes. I am blessed to have friends who are much more open-minded and nonjudgemental than some of the people I know. -EdwardianEra

[ChipsHH]

I am blessed to have friends who are much more open-minded and nonjudgemental than some of the people I know.

-EdwardianEra

Have to agree with ya there.

[ChipsHH]

Your mom ever catch on to the fact that you were wearing her heels?

Yeah. Wish I could post a link to get you there, cause I talk about it on another topic around here, so yeah.

[dingpat]

yesterday actually, age 19. low heels though. still made the clacking sound as I browsed through the shop.

[ChipsHH]

What shop, if I may ask? If it applies, what shoes ya get?

[dingpat]

it was actually a ross. I bought the shoes from payless, they were low heel (1 inch) sling-back type shoe, really cute. just walked the womens section. Felt nervous at first, but then decided I loved it

[ChipsHH]

Good go. Did u walk out with them on? And did u get any stares while shopping?

[skirtsnhose]

I was in high school, so around 15 or so. It's been an on-again, off-again thing since then, for about 20 years now.

[HeelsForMen]

On a paper round at 14 i use to borrow some ladys 3in heels and do my paper round wearing them (remember walking up the paths but mostly cycling) then replace them back in her porch at the end, they were always there so guess she never caught on, and was nearly caught lots of times but in hindsight was probably caught loads of times just no-one said nothing as very much doubt i walked all those paths without someone looking out window and they were clacker type. You are more fearless when you are younger probably because the consequences seem less harsh.

[hh4evr1]

I started wearing heels in public about 2 years ago. I wore block heels to work every day and sometimes go for a walk in stiletto boots.

[heelguy]

i started wearing heels around 15, sneaking out under the cover of darkness for walks... im now 19

[roniheels]

I started wearing high heels (my mom's) in my teens. I started wearing men's and women's high heels publicly when I was 18, the best of my recolection.

[Histiletto]

For this thread, when heels are referred to, I take it to mean the shoes that females, not males, are socially approved to wear. Around the age of 3 years old, I got my own pair of black patent leather Mary Janes and publicly wore them all the time. I was too young to care what others said or thought about my choice of footwear. While the Mary Janes were my sisters before they became mine, I would often put them on, inspite of my sister's objections and my parents interventions. Finally, when she couldn't wear them any more and got some new shoes, I saw my opportunity and made them mine. Yes, life was a heaven on earth for a spans of several months. Then the social standards were thrown upon me when my pleas for another pair were ignored and then out-right forbidden. It took a while to understand the reason for not helping me get another pair, but my desire to wear them continues on. Being denied the wearing of my choice of footwear publicly only made my resolve to wear them more intense, which lead to some episodes of less than honorable dealings. What could I do otherwise, though? I was a child and felt alone, I couldn't express my desires openly, without the unwanted social repercussions from everyone I knew. They weren't aware that a male could have the desire to wear "heels" and still be a "normal" human being. So there I am, a secretive non-conformist in a crowd of my contemporaries, being careful not to exhibit any unusual stereotypical performances for their notice. This environment and the subsequential attitude I developed is hard to shred and open up after living in it most of my life. I suppose these feelings of social alienism will continue to be part of my public heeling, no matter how much it becomes accepted.

[William]

I remember trying on my Mom's and Sisters' heels around the age of ten. I was older (high school and college) before ever buying any of my own. My collection of heels is small compared to several members here. I remember falling in love with high heel cowboy boots (3") and wearing them in college. But while still in high school, there were a few of my friends that bought and shared funky retro shoes and clothes to wear for fun, including a few pairs of original disco-esqe platform shoes and boots. I still don't wear extreme heights in public very often. I wear 6-7 inch heels at home quite a bit to relax in. Still hoping for a fashion change to come around again that would have famous rockers and fashion forward men in heels again to help set the trend...

[Jamie001]

The only person that can set the trend is you and the rest of us here. We cannot wait for famous people to embrace our cause because it may never happen. Life is short and you need to wear what you want to wear and don't worry what other people think.

I remember trying on my Mom's and Sisters' heels around the age of ten. I was older (high school and college) before ever buying any of my own. My collection of heels is small compared to several members here. I remember falling in love with high heel cowboy boots (3") and wearing them in college. But while still in high school, there were a few of my friends that bought and shared funky retro shoes and clothes to wear for fun, including a few pairs of original disco-esqe platform shoes and boots. I still don't wear extreme heights in public very often. I wear 6-7 inch heels at home quite a bit to relax in. Still hoping for a fashion change to come around again that would have famous rockers and fashion forward men in heels again to help set the trend...

[heelsinmass]

i started at about 11 or 12, but wore them out fully dressed as a girl when i was about 27. then just heels dressed as a gut about 2 weeks ago. i have a great wife she lets me do stuff like that, i just hope she asks me to do it more now lol.

[joeshoething]

I started wearing my mom's hels when I was roughly 5. every year she would pull out the Halloween Box, and I couldn't wait to get the silver glitter 4-5 inch wedges out and put them on. My first public outing had to have been in high school (opposite gender day during homecoming). That was the first time I ever spent the day in high heels. It was awesome. Since then I have done a few laps around the college campus, at night, and a few trips to the malls. Those occasions, I went out in full femme, and being young at the time had a face with no 5 o-clock shadow, so was passable. Even got a few hoots and hollahs from drive buys!

[William]

Jamie, I totally get where you're coming from. My circumstances involve working with kids on a daily basis. If high heel shoes on guys were fashionably in style, I would not hesitate to indulge personal style. But, as it would be cause of great concern as to why some dude was wearing high heels in my setting, I'll pass. Kids are confused enough. I'm not about to add to their stress level. There's obviously a right time and a right place for everything. Still, thanks for your thoughtful words of encouragement. Wil