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I was having a great time in my RL boots walking around in Vegas the other day when I stumbled a bit and noticed more clicking than usual coming from my 4" stiletto boots.  Sure enough, logging the miles had blown out on of the heel tips.  I made my way back to the hotel and took a seat in the bar/casino area to watch the world go by.  I did notice one nice looking tall gent with long grey hair was having a great time with a few people around him, all laughing it up....

I then noticed he was bare footed and was holding a pair of strappy heels in his hand!  Stay cool I thought, don't be creepy, don't go lurking around him.  But, on the other hand, I did not want the opportunity to meet this fellow and compliment his footwear get away.  I watched as he and his friends got up and headed for an exterior door, better hurry up and do something I thought.  I followed the group as they went outside, they seemed to be waiting for a cab...Then, the gent turned around, headed back for the door, I intercepted him by opening the door for him and giving the usual "like your heels" compliment.  The gent laughed saying he was creating quite the stir, he claimed one of his gal pals' feet were killing her while wearing the strappy silver heels.  The gent had given her his sandals and was holding her heels....I almost blurted out with something like  "well I'm sure those heels would look great on you...." compliment but decided he might be offended so kept my trap shut (amazingly).  We laughed as he went back out the door.  Funny thing is, I forgot all about me wearing 4" stiletto boots, and I don't think the gent even noticed my boots....

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That would have been amazing if he were the wearer of the heels + him admitting defeat to you.

But you're better than me. I probably would have stared, looked away, and he'd be gone in a flash.

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Formally "HHDude"

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I have never seen another guy in high heels - or gals shoes for that matter.  I know they are out there, still looking.....   Maybe someday....  sf

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"Why should girls have all the fun!!"

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On 10/25/2017 at 12:39 PM, pebblesf said:

I was having a great time in my RL boots walking around in Vegas the other day when I stumbled a bit and noticed more clicking than usual coming from my 4" stiletto boots.  Sure enough, logging the miles had blown out on of the heel tips.  I made my way back to the hotel and took a seat in the bar/casino area to watch the world go by.  I did notice one nice looking tall gent with long grey hair was having a great time with a few people around him, all laughing it up....

I then noticed he was bare footed and was holding a pair of strappy heels in his hand!  Stay cool I thought, don't be creepy, don't go lurking around him.  But, on the other hand, I did not want the opportunity to meet this fellow and compliment his footwear get away.  I watched as he and his friends got up and headed for an exterior door, better hurry up and do something I thought.  I followed the group as they went outside, they seemed to be waiting for a cab...Then, the gent turned around, headed back for the door, I intercepted him by opening the door for him and giving the usual "like your heels" compliment.  The gent laughed saying he was creating quite the stir, he claimed one of his gal pals' feet were killing her while wearing the strappy silver heels.  The gent had given her his sandals and was holding her heels....I almost blurted out with something like  "well I'm sure those heels would look great on you...." compliment but decided he might be offended so kept my trap shut (amazingly).  We laughed as he went back out the door.  Funny thing is, I forgot all about me wearing 4" stiletto boots, and I don't think the gent even noticed my boots....

I know what you mean. Had similar request from a beautiful woman at work. She had on platform silver strapy sandal heels, all dolled up for evening event. She cried out to group of us. Looking more towards me focusing her request. Asking if she could swap her heels wearing my shoes. Only I was wearing sneakers. It gave me clue into she suspected I wear heels also. Only few in my group laughed upon her calling her stupid for wearing such shoes. While I muttered to her I doubt they fit me. Nobody took my comment seriously but sort of knew she did taking second surprised stare upon me. Realizing I maybe right about sizing looking back at me, as I was serious. Seeing that I often wear tight female jeans at work. Isn’t out of the realm of possibility I may pertake wearing a heel shoe now and again. In her mind if a guy cross dressed in skinny woman jeans he probably has a woman shoe in his closet. 

Yet if at any other location if the familiar woman I recognized asked me I will do it giving her mine. That is if I was wearing heel booties giving her the chance to wear mine. Doubt any woman would judge or complain for me wearing heels only be thankful I helped being gentlemen. Makes for great story for her laughing later to her female friends. Yah, there was a guy in heels gave me his saved my feet for the evening. 

Edited by MackyHeels
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9 hours ago, SF said:

I have never seen another guy in high heels - or gals shoes for that matter.  I know they are out there, still looking.....   Maybe someday....  sf

You just got to look in the right places. I've seen several and we live in the same geological area. Keep trying

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28 minutes ago, Cali said:

You just got to look in the right places. I've seen several and we live in the same geological area. Keep trying

I will say that I saw a lot more women in heels in your neighborhood than I will in mine. Wedge heels seem popular where your at.

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It can be a lonely life, but I am wiling to make the sacrifice for the good of the group....  ha ha...

In fact I was out in heels today, running errands.  Then I saw my reflection in a glass window - don't suppose that counts as seeing another guy in heels???  

Bummer......    have fun all...    sf 

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20 hours ago, SF said:

don't suppose that counts as seeing another guy in heels???  

Only if it's an out-of-body experience.

I was down in Almaden Valley today in my errand wedges...you just didn't look at the right place. LOL

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I have only seen two other guys in heels (excluding drag shows).  One was a young fellow who was standing/dancing on the sidelines while the pride parade went by,  he handled those heels like a champ and looked great in them.  The lad was fairly young, so I did not want to appear "creepy" by jumping the barrier to compliment him.  The other was waiting in line behind me for a bar in SF, he had great black thigh high boots on, I did compliment him and we had a nice chat. 

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Very kind of you. I am sure you have a wonderful collection, and no doubt wear them all out and about, as do many people on this site. But we are talking very, very tiny numbers here. The total population of HHP is probably no larger than the total number of climbers who summited Mt Everest this year. Ones odds of encountering one, randomly, on a city street or in an airport, are vanishingly small. 

I have travelled to every US state, most of the Canadian provinces, and more than 100 countries and yet I have never, in all that time and distance and across a vast spectrum of peoples and cultures, encountered a guy in heels. 

Edited by Shyheels
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On 7/2/2018 at 1:03 PM, Shyheels said:

Very kind of you. I am sure you have a wonderful collection, and no doubt wear them all out and about, as do many people on this site. But we are talking very, very tiny numbers here. The total population of HHP is probably no larger than the total number of climbers who summited Mt Everest this year. Ones odds of encountering one, randomly, on a city street or in an airport, are vanishingly small. 

I have travelled to every US state, most of the Canadian provinces, and more than 100 countries and yet I have never, in all that time and distance and across a vast spectrum of peoples and cultures, encountered a guy in heels. 

With that kind of logic behind you, I'm not surprised :P

Only kidding, of course. I'm on the logic of "anything can happen" and after today's happening at work, ANY thing can happen, haha.

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1 hour ago, ChipsHH said:

With that kind of logic behind you, I'm not surprised :P

Only kidding, of course. I'm on the logic of "anything can happen" and after today's happening at work, ANY thing can happen, haha.

Okay, I’ll bite...what happened at work?

To be sure, anything can happen and I have seen many an unusual thing and had many unusual experiences in my travels, but so far no men in heels. And while it would no doubt be possible to engineer a sighting - meeting up with a fellow HHP member for example - I suspect I could travel many more years before such a thing happened naturally and randomly. 

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On 7/2/2018 at 1:43 AM, Shyheels said:

In a lifetime of travelling, through many, many countries and on every continent I have never seen a guy in heels. Not once.

I have, but only low heels in public.

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(formerly known as "JimC")

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A quick and very approximatively calculation brings me to the conclusion that there are probably not more than around 100 public heelers on our earth. So not surprising we never meet any. 

We must urgently explore new planets! 

The number of Men in heels at home seems to be much more important. 

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And on that front - men who like to wear heels, or wished they dared, but in any event do not do so in public - I suspect the number is considerably larger than most people  suspect. Wasn't it Thoreau who said the great majority of men lead lives of quiet desperation?  

Edited by Shyheels
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3 hours ago, Shyheels said:

And on that front - men who like to wear heels, or wished they dared, but in any event do not do so in public - I suspect the number is considerably larger than most people  suspect. Wasn't it Thoreau who said the great majority of men lead lives of quiet desperation?  

Well said indeed

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On 7/3/2018 at 8:58 PM, Shyheels said:

Okay, I’ll bite...what happened at work?

To be sure, anything can happen and I have seen many an unusual thing and had many unusual experiences in my travels, but so far no men in heels. And while it would no doubt be possible to engineer a sighting - meeting up with a fellow HHP member for example - I suspect I could travel many more years before such a thing happened naturally and randomly. 

A lady who joined the job as I did mouthed off to her trainer, and she didn't seem like the type to do that!
Same lady also confessed to having a husband, and I assumed otherwise! (going by her hairdo) *shame on me, I know*
And most recently...
I did a job that was outside my job description. (The perks of Retail, I suppose)

Although if you want something more...concrete, I am tempted to - and just might - take my flatform sandals to work and wear them out as I leave. No one, FAIK, has seen me in such yet. These days, it's FAR too hot to be wearing shoes that are nearing its expiration date.

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2 hours ago, ChipsHH said:

A lady who joined the job as I did mouthed off to her trainer, and she didn't seem like the type to do that!
Same lady also confessed to having a husband, and I assumed otherwise! (going by her hairdo) *shame on me, I know*
And most recently...
I did a job that was outside my job description. (The perks of Retail, I suppose)

Although if you want something more...concrete, I am tempted to - and just might - take my flatform sandals to work and wear them out as I leave. No one, FAIK, has seen me in such yet. These days, it's FAR too hot to be wearing shoes that are nearing its expiration date.

Sounds to me that it’s a workplace that could do with a bit of stirring up. Go on, wear the sandals. Truth is though, nobody will notice. Not even if you wore patent pink stiletto thigh highs. They’ll all be still gawping in wonder at the lady who mouthed off to her trainer...

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On 7/2/2018 at 7:03 PM, Shyheels said:

Very kind of you. I am sure you have a wonderful collection, and no doubt wear them all out and about, as do many people on this site. But we are talking very, very tiny numbers here. The total population of HHP is probably no larger than the total number of climbers who summited Mt Everest this year. Ones odds of encountering one, randomly, on a city street or in an airport, are vanishingly small. 

I have travelled to every US state, most of the Canadian provinces, and more than 100 countries and yet I have never, in all that time and distance and across a vast spectrum of peoples and cultures, encountered a guy in heels. 

I'm not nearly as well-travelled as you, nor do I frequent clubs.   However, over the last 60-odd years, I reckon I have seen at least ten men in public in the UK who were wearing heels that were either intended for women or at least of a conspicuous height and style - so excluding 1970s men's platforms, cowboy boots and Beatle boots and the like.   Probably half of them were dressed as women (or at least wearing other feminine clothes); the others in essentially or wholly male mode.   I can't identify any particular trend as to the time or place of my sightings but they remain quite vivid memories because of their admitted rarity.   But 10 is not zero.

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I can't speak to your experience, only mine. But ten individuals in the course of 60 years and the tens of thousands of people you would have encountered, at least visually, in that span of time, is such a tiny percentage that the difference between it and zero is negligible.   

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54 minutes ago, Shyheels said:

I can't speak to your experience, only mine. But ten individuals in the course of 60 years and the tens of thousands of people you would have encountered, at least visually, in that span of time, is such a tiny percentage that the difference between it and zero is negligible.   

I think you miss the point.   Your implication that male heel-wearing is negligible to the point of non-existence because you, personally, have never witnessed it (which I find surprising) is devalued by even one sighting, let alone my ten.   Yes, it is rare - and I for one do not claim otherwise - but clearly it does exist.

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Er, no. I don't miss the point in the least. I never once said or even suggested that men wearing heels do not exist, only that I have never personally encountered any and that given the amount of travelling I do and my exposure to the world, that the overall number of heel wearing men must be negligible. Your pointing out that you have seen but ten men wearing heels in public in the past sixty years rather underscores my point, I think.  Men who wear heels in public are vanishingly rare.  

We could put it this way if you like.  There are people in this world who are well over seven feet tall. I know they exist, but I personally have met only one person who was seven feet tall, and nobody who was taller than that. Now, I might strike up a conversation with an NBA basketball coach who says he sees such people all the time. Does that make them commonplace and my experience invalid?  I think not. 

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