Men, What Made You Want To Wear Heels

[Shafted]

Please spare me. Sorry, but this sounds like it belongs more in the stories forum. The more I read, the less I believed.

[SF]

hmmmmm, interesting….????

[Crushinboots]

Well actually Shafted my late mum would comment on how when I was younger I was never out of her boots.

It is true

[dannyM]

For me, it's the bondage idea of wearing high heels. The restriction they give, they make you alert to every step you make,  certainly if you push your limits a bit...

[Histiletto]

For those who aren't familiar with the return of high heels over the last couple of centuries, there are some enjoyable notes of enlightenment waiting to be discovered. However, this thread is concerned about how any person - men, in this case - have gotten interested in wearing heels. 

As I have posted earlier in the beginning of this thread, I haven't known any time in my life that didn't include the desire to wear my favored design, styling, and type of heels to some degree. The need to find some fulfillment for my desire, lead me into many sporadic happenings and sometimes initiating tactical manipulations of occasions to secretively slip on a pair or more, if only to feel and see them on my feet for a moment or so. Many memories of these incidences have been recalled as I read the activities of others having their first and subsequent experiences with high heels. They may have not been exactly the same as mine, but the similarities as they have devolved their experiences are proving to be striking coincidences.    

[Rick24]

because im tried of wearing flats nearly all day, whats more great than wearing a pair of overknee stiletto boots with a 5inch heel, its ridiculous that society today still wants to treat men like little kids,

[BigEed]

For me, I had an older sister. She was quite popular and as such, had quite the collection of pumps, strappy sandals, clogs and other assorted shoes. 

I used to sneak into her room while I was home babysitting my little brother and sister and play with her shoes being very careful to put them back exactly the way I found them. 

She had the wooden sandals with a leather strap that I could wear. They were so smooth and really felt good. My feet were too big even for my older sister's shoes.

I got caught with her shoes a time or two and my parents shamed me over it every time. Over the years, I would have a stash of stuff but they caught me with it every time. I think they believed I was gay.

Over the years, I have fantasized about having my own heels. I finally ordered a pair online last week along with some ankle nylons to wear in my home office. I don't forsee ever going out with them on; I have several friends who are homophobic and who would interpret me heeling as me being gay. 

My wife is awesome and doesn't have a problem with my fetishes and the shoe thing is no different, although we agree that this is something that is to be kept out of the view of our kids.

I'm glad I found this website. This is the very first time I have ever posted about my desire in public.

-eed.

[maninpumps]

BbigEed ,

 Your beginnings sound a lot like mine . I had a sister with a pair of leather and wooden soled sandals much like you described . She caught me in them and said if you are going to wear them ...learn to walk in them so she put on a pair of heels and taught me . Then to my surprise she gave me the pair I was wearing . They finally after miles of wear started to wear out and she made sure I had another pair about two sizes up as my feet were still growing . 

 I was in middle school back then and to this day she still has to show me her new heels and has to check out mine . Funny how we have been doing this for 30 years . I have moved more to platform wedges and she has moved to the lower 2-3 inch heels . We both like the peep toe style . 

 My family all know about my heels and crossdressing . I have been lucky about my folks and the fact they never judged me . My children have figured it out . My daughter asked once "Mom why do you have so many large high heels ?" and she told her they are daddy's . My daughter said can I wear them dad ? I said if you an walk in them . We don't make a big thing of it . The children see it  as no big deal either. I do hear about it if she thinks the style is wrong for me . I will say, when I am wearing heels or crossdressed I am not with the children unless they want to . 

[Thighbootguy]

This thread has been going for a while and provides some really interesting reading.  I don't know how I missed posting in it... so here it goes.

My fascination with heels has come relatively recently.  My earliest recollection is back high school (early 60s) when I became fascinated with women's boots.  I remember buying a pair in a thrift store that had a 2" block heel and just loving wearing them (in private).  Occasionally I would venture out with them on under my jeans.  Around that time there was a crotch high stretch boot with a 2" block heel in style.  The boots were meant to completely cover your leg and the top should disappear under a skirt.  I bought a pair from a Montgomery Ward's mail order store and really enjoyed them.  This was many years before the internet.  Over the years I bought more thrift store boots until about ten years ago.

 

Remembering the tall boots I had in my youth, I wanted another pair but the only thing I could find that was in a size I could wear were Pleaser's thigh boots and they came with a 5" stiletto heel.  I had the money at the time and ordered a pair and I remember opening the box and thinking, "How will I ever walk in these?".   You can pick up the rest of my story in Thigh Boots in Public.  I have been wearing heels ever since.  Now when I look at boots I do look for a high heel.

[LovesHiHeels]

Not sure why I started wearing heels but I know wanted to see If I could walk in high heels 

 

[pebblesf]

I have spent many years trying to "figure out" just where my love of boots originated.  Genetic, or learned, really don't know.  All I know is that I had a fascination with boots of all sorts when I was very young.  I clearly remember my fascination with my sister's red go go boots, and wearing them while alone in the house.  I am particularly fond of taller boots with high stiletto heels, I know my family realizes I have a thing for boots, but they do not realize I enjoy wearing 5" stilettos.  I would love to know if I was hard wired from birth with a love of boots, or if it is a learned thing, but have learned to just accept and enjoy my boots. 

[bss]

As for me... High heel stiletto pumps were like love at first site.  As far as I can recall, I have always love high heel stiletto pumps since I was born.  I remember playing with my mom's shoes when I was a couple years old.  Being that the shoes where just too big back then, I think it was just the love of seeing women wearing the high heel stiletto pumps.  Once I grow enough to fix into some high heel shoes, the desire to wear them just sky rocketed.  

High heel shoes and boots are a work of art.  They are beautiful.  They are colorful and they have a very sexy curve shape.  Although high heel shoes and boots can be painful to wear at times; the form fitting, rich soft buttery Italian leather, arch supported stiletto high heels feel so amazing.  The infinite styles, textures, colors and materials will never bore you.  This is what really made me want to wear high heel shoes and boots.

 

[Kittyinboots]

My desire to wear high heel boots was mostly learned.  Movies, TV shows and music videos showed very sexy boots and it was my desire to dress like these stars, walk like they did, reenact those scenes.  

I thought that I would never wear a pair of high heel boots in my lifetime and I would just accept it. My first pair was purchased at a thrift store.  Thanks to Internet sites, I was able to find my first pair of thigh high boots, which again I never thought I would wear. 

My desire to wear boots also came from my dreams. I had a dream a very long time ago, that I was walking in a parking lot wearing a short black leather jacket, tight blue jeans and sexy high heel black pirate boots. This was long before I had any boots. This past Sunday I wore my slim fitting black jacket, blue denim riding jeans and my recently acquired high heel black pirate boots.  Then I drove to that parking lot near where I grew up and walked across that lot feeling confident that I lived my dreams.

[Histiletto]

Contrary to popular social attitudes, many men have just as much need, interest, and/or taste as many women have in the wearing of the attire they find looks good. In this respect, we are equal. Letting people have the respect to naturally choose and wear their own desired outfits has not been a societal feature. I guess this thinking stems from the status policies created by civilization when people were placed by their wealth and power while using attire as identifiers of their job or community positions. The natural right to choose our own outfits depending on our personality tastes was taken away. Then standards were set up to place more controls over what people could choose to wear. When these man-made rules were challenged or not kept, the attitude was to ridicule, persecute, imprison, and/or exile the defilers until they returned to complying or met with death. Society promoted these perpetrators as demons, perverts, and social idiots so the fear of such titles would help, encourage, or even force others to stay in compliance. Things haven't seem to change much in this day and age of the greatest exponential learning and technical advancements ever known, yet we can't know what each individual thinks and perceives all the time. Individuality is a natural property of how mankind is suppose to function. When the ability to choose ones own attire was taken away, the natural power to be and express differences was compromised. The social contentions, like men's high heels or women's pants wouldn't have become a social issue, if people's right to choose their own apparel had never been placed in society's dictation.  

[Shyheels]

No, the right to choose your own attire remains absolutely yours, as it always has. You are free to wear whatever you like, in terms of fashion or style. But along with that choice of fashion or style comes the choice to stand out, or not to stand out. Many - most - choose not to stand out. 

But the choices are always ours. 

[Histiletto]

Yes, the choice of what we wear has always been ours, but social standards have caused the exercising of this choice seem like it is a sin or a perversion against society's intent to make us comply with its ideals.

[Shyheels]

That hasn't stopped Thighbootguy, CAT or Jeff B from wearing any damned thing they please, any time they like, and they seem to be prospering. Melrose Plant wears heels all the time. His blue collar mates know all about it, so do the folks at his church choir. He's still breathing, as far as I know.

Choices are ours. 

Wasn't it Emerson who said "What you think of me is none of my business."

Edited March 17, 2017 by Shyheels

[mlroseplant]

 

6 hours ago, Shyheels said:

That hasn't stopped Thighbootguy, CAT or Jeff B from wearing any damned thing they please, any time they like, and they seem to be prospering. Melrose Plant wears heels all the time. His blue collar mates know all about it, so do the folks at his church choir. He's still breathing, as far as I know.

Choices are ours. 

Wasn't it Emerson who said "What you think of me is none of my business."

It pains me to find myself in the situation where I must be contradictory, but since my name has been dragged into this conversation, I feel I must answer.

I don't disagree with you that we are free to wear what we want, the limitation on that being our own personal boldness and ability to be thick-skinned. However, when I say "free," there are limitations on that as a male, much in the same way that I am "free" to not go to work if I so choose, but it doesn't keep a roof over my family's head if I choose to exercise that freedom.

In your four examples, each of these fine fellows has a limitation on their fashion freedom, by their own admission. I'll start with myself. I am not allowed to wear heels when we visit Vietnam. That's the rules. A small price to pay for domestic tranquility. Sometimes, here in the USA, my wife will tell me, "We will be going to visit such and such at his house. You will not wear heels, nhé? Or, and here is the worst one, if I am to play or sing something at church (where I always wear heels) and she wants to video it so that she can show the folks back in Vietnam, she will often insist that I wear flats so that the people back in Vietnam don't see what a freak I am. It's no problem, I have just come to accept it, got to keep the wife happy to make the life happy. But I am certainly not free to wear whatever I want, whenever I want, and it is because I am a man.

TBG is probably the closest to me in execution, and by that I mean that he wears "alternative" clothing every day, rather than saving it for special occasions. Even he admits that there are certain venues where he will not wear certain things. That's because he's a man.

JeffB is perhaps the most thoroughly thought out dresser in this whole bunch, but, as far as I know, his impeccable style is reserved for his jaunts only. It's not an everyday thing with him. I am sure that were he a woman, he would feel free to wear the type of outfits he wears on his jaunts to work every day. Alas, that is not the case.

CAT I don't know very well, but he has indicated in his prior posts that the reason he always crops out his face in his numerous photographs is to protect his kids from possible ridicule, should their dad be discovered by accident on the internet, dressed like that. I can infer from this that he doesn't walk around his neighborhood every day wearing what we see on here, or the face-cropping thing wouldn't make a bit of sense. Again, if CAT were a woman, this would simply not be an issue.

So, you know, yeah, we're free to wear what we want in the theoretical sense, but reality often dictates that we conform to society's expectations. I guess I'm not complaining. It's actually gotten a lot better in recent years, and I expect that trend will continue in the years to come.

[Shyheels]

Life is inevitably a series of compromises, no matter which sex you are, or what your field of endeavour. Apologies for dragging your name into a conversation to which you were not originally a party.  I mentioned you and the others (positively, I hope) as examples of people who enjoy - or appear to enjoy - a large measure of the sort of sartorial freedom the earlier poster suggested does not exist. 

We all make our choices, of course, the wiser of us taking into account the feelings and sensibilities of those around us and going from there. We act with restraint. We look for balance, an appropriate level of give and take. And that's not necessarily a bad thing. No man is an island, as John Donne said. We all exist in concert with others.

Conformity, manners and a social sense also have their place. Even the best natured of us do not really like to be jarred too much. We don't really want people bringing six packs of beer to a funeral, or firing up cigars in church, sitting shirtless at the next table at a restaurant or teachers coming to school in drag, all in the name of personal freedom.

We are all censorious in our way, too. Gosh, I know how much i hate it when I see people boarding planes in shiny track suits, or shorts and flip-flops, looking like they just stepped off the beach. 

My point, I suppose, is that we are not helpless blobs of putty. 

Edited March 17, 2017 by Shyheels

[mlroseplant]

There was a fellow at university I used to hang around with whose name was, and I shit thee not, Bell Island. I suppose he was an Island.

Seriously, thanks for the thoughtful reply. Personally, although I don't follow the modern super casual dress code when flying the friendly skies, I can understand it. Back when people used to dress up to fly, they actually flew you around in reasonable comfort. When we fly, I usually wear a jacket (but not a tie), and my wife wears heels. I kind of wish she wouldn't, though. She is just simply not as fast as I am in heels.

[Shyheels]

6 minutes ago, mlroseplant said:

There was a fellow at university I used to hang around with whose name was, and I shit thee not, Bell Island. I suppose he was an Island.

Seriously, thanks for the thoughtful reply. Personally, although I don't follow the modern super casual dress code when flying the friendly skies, I can understand it. Back when people used to dress up to fly, they actually flew you around in reasonable comfort. When we fly, I usually wear a jacket (but not a tie), and my wife wears heels. I kind of wish she wouldn't, though. She is just simply not as fast as I am in heels.

You seem like a nice guy - I just hope I didn't offend with my earlier post

you are so right about the deterioration of air travel! I do try to maintain a smart casual look, even in the tropics. 

As for me I like my pull-on otk suede boots, but I do not wear them travelling because of the hassles taking them off at security. 

 

Edited March 17, 2017 by Shyheels

[mlroseplant]

6 minutes ago, Shyheels said:

You seem like a nice guy - I just hope I didn't offend with my earlier post

you are so right about the deterioration of air travel! I do try to maintain a smart casual look, even in the tropics. 

 

Absolutely no offense (offence) taken. I actually welcome the opportunity to further the discussion.

[Shyheels]

I'm glad. It's a good discussion. Worth pursuing and furthering.

[Thighbootguy]

13 hours ago, Shyheels said:

That hasn't stopped Thighbootguy, CAT or Jeff B from wearing any damned thing they please, any time they like, and they seem to be prospering.

and doing well in retirement thank you.  I really never thought I'd be an outlier here at HHPLACE.

6 hours ago, mlroseplant said:

TBG is probably the closest to me in execution, and by that I mean that he wears "alternative" clothing every day, rather than saving it for special occasions. Even he admits that there are certain venues where he will not wear certain things. That's because he's a man.

I seem to wear whatever suits me on any particular day.  Some days it's boots and jeans, some it's boots and a dress and sometimes (but not often) I try CD.  My common theme is boots.  There are places I go that won't push past boots and jeans, most of these are musical or church venues where I am playing.  However when I go shopping, I'll wear anything I want as most people don't care what a paying customer is wearing.  I can usually tell if I have pushed my presentation too far on a given day when it comes time to get out of the car.  Most of the time I notice my boots hitting the ground and I take off walking without a second thought.  Other times, while still sitting behind the wheel, I'm thinking, Do you really want to do this?", and this is not always determined by what I'm wearing (but it most often happens when I'm wearing a dress).

All I know is that I'm retired and having more fun than I've ever had before.

6 hours ago, mlroseplant said:

the face-cropping thing wouldn't make a bit of sense. Again, if @CAT were a woman, this would simply not be an issue.

I'm not too sure about that.

[Jkrenzer]

I'll be honest. It started as pure fetish lust for me until I finally donned my first pair. Then I fell in love not just with the look (fetish) but the feel (me and no fetish). Now I wear my heels because I like the look and feel on me. Do I still get excited seeing women in heels? Absolutely, but now it's more because I think about how I'd look and feel with them or how much better I actually walk around in them than the person wearing them. 

[HappyinHeels]

All have made great points here. There is a process filtered by personal limits and one's own sense of comfort in their surroundings. I wear heels everyday but I am cognizant of where I do it. The farther from work and home the more obvious the heels and the more mixed my warddrobe becomes. What is inescapable in all of our journeys and experiences is we are enjoying a one-shot deal. We have a finite lifespan and an even shorter period to wear whatever we want while we're still ambulatory and in decent health. Make the most of your ONE chance to enjoy your life on your own fashion terms. HappyinHeels

[JeffB]

On 3/17/2017 at 0:58 AM, Shyheels said:

That hasn't stopped Thighbootguy, CAT or Jeff B from wearing any damned thing they please, any time they like, and they seem to be prospering.

Well, I certainly do as best I can, I won't deny that.

21 hours ago, mlroseplant said:

JeffB is perhaps the most thoroughly thought out dresser in this whole bunch, but, as far as I know, his impeccable style is reserved for his jaunts only. It's not an everyday thing with him. I am sure that were he a woman, he would feel free to wear the type of outfits he wears on his jaunts to work every day. Alas, that is not the case.

You were right about everything you said, my style is indeed reserved for my outings and not day to day dressing, I wish it could be more, like wearing my outfits to work, but I'm rather limited while I'm still doing the 9 to 5 rat race thing. However, I have envisioned and toyed with the idea of throwing away all my men's stuff and wearing ONLY women's clothes and shoes 24/7 after I retire. That would be fun.

[pebblesf]

On ‎3‎/‎17‎/‎2017 at 0:58 AM, Shyheels said:

That hasn't stopped Thighbootguy, CAT or Jeff B from wearing any damned thing they please, any time they like, and they seem to be prospering. Melrose Plant wears heels all the time. His blue collar mates know all about it, so do the folks at his church choir. He's still breathing, as far as I know.

Choices are ours. 

Wasn't it Emerson who said "What you think of me is none of my business."

well said indeed...

[pebblesf]

On ‎3‎/‎17‎/‎2017 at 7:49 AM, mlroseplant said:

 

It pains me to find myself in the situation where I must be contradictory, but since my name has been dragged into this conversation, I feel I must answer.

I don't disagree with you that we are free to wear what we want, the limitation on that being our own personal boldness and ability to be thick-skinned. However, when I say "free," there are limitations on that as a male, much in the same way that I am "free" to not go to work if I so choose, but it doesn't keep a roof over my family's head if I choose to exercise that freedom.

In your four examples, each of these fine fellows has a limitation on their fashion freedom, by their own admission. I'll start with myself. I am not allowed to wear heels when we visit Vietnam. That's the rules. A small price to pay for domestic tranquility. Sometimes, here in the USA, my wife will tell me, "We will be going to visit such and such at his house. You will not wear heels, nhé? Or, and here is the worst one, if I am to play or sing something at church (where I always wear heels) and she wants to video it so that she can show the folks back in Vietnam, she will often insist that I wear flats so that the people back in Vietnam don't see what a freak I am. It's no problem, I have just come to accept it, got to keep the wife happy to make the life happy. But I am certainly not free to wear whatever I want, whenever I want, and it is because I am a man.

TBG is probably the closest to me in execution, and by that I mean that he wears "alternative" clothing every day, rather than saving it for special occasions. Even he admits that there are certain venues where he will not wear certain things. That's because he's a man.

JeffB is perhaps the most thoroughly thought out dresser in this whole bunch, but, as far as I know, his impeccable style is reserved for his jaunts only. It's not an everyday thing with him. I am sure that were he a woman, he would feel free to wear the type of outfits he wears on his jaunts to work every day. Alas, that is not the case.

CAT I don't know very well, but he has indicated in his prior posts that the reason he always crops out his face in his numerous photographs is to protect his kids from possible ridicule, should their dad be discovered by accident on the internet, dressed like that. I can infer from this that he doesn't walk around his neighborhood every day wearing what we see on here, or the face-cropping thing wouldn't make a bit of sense. Again, if CAT were a woman, this would simply not be an issue.

So, you know, yeah, we're free to wear what we want in the theoretical sense, but reality often dictates that we conform to society's expectations. I guess I'm not complaining. It's actually gotten a lot better in recent years, and I expect that trend will continue in the years to come.

happy wife equals happy life!

[pebblesf]

On ‎11‎/‎8‎/‎2015 at 8:32 PM, BigEed said:

For me, I had an older sister. She was quite popular and as such, had quite the collection of pumps, strappy sandals, clogs and other assorted shoes. 

I used to sneak into her room while I was home babysitting my little brother and sister and play with her shoes being very careful to put them back exactly the way I found them. 

She had the wooden sandals with a leather strap that I could wear. They were so smooth and really felt good. My feet were too big even for my older sister's shoes.

I got caught with her shoes a time or two and my parents shamed me over it every time. Over the years, I would have a stash of stuff but they caught me with it every time. I think they believed I was gay.

Over the years, I have fantasized about having my own heels. I finally ordered a pair online last week along with some ankle nylons to wear in my home office. I don't forsee ever going out with them on; I have several friends who are homophobic and who would interpret me heeling as me being gay. 

My wife is awesome and doesn't have a problem with my fetishes and the shoe thing is no different, although we agree that this is something that is to be kept out of the view of our kids.

I'm glad I found this website. This is the very first time I have ever posted about my desire in public.

-eed.

I had similar experiences as a kid.  I'm glad you finally have your own boots to enjoy and a great wife who is understanding and wants you to be happy.