Age first started wearing heels and your thoughts on wearing them.

[RonC]

8 minutes ago, Bubba136 said:

My mother was just the opposite.  She encouraged me to wear her heels when I was a little boy.  And, when I outgrew her size when I was about 10, she bought me 2 pair of my own.

Wow!  That is pretty rare.

[hiddenheels]

For me, it was when I was ~13-14 that I remember the attraction, but it wasn't until I was ~18 that I bought my first. Been struggling with my own acceptance for decades, and I'm just finally starting to accept and embrace that "this is me".

[pebblesf]

14 hours ago, Bubba136 said:

My mother was just the opposite.  She encouraged me to wear her heels when I was a little boy.  And, when I outgrew her size when I was about 10, she bought me 2 pair of my own.

What a great Mom indeed

[spikesmike]

Bubba136 :  I like your mom.    spikesmike

[Bubba136]

I believe she thought that in time,I would outgrow the desire.  Which I almost did.

[Breeheels]

6 hours ago, spikesmike said:

Bubba136 :  I like your mom.    spikesmike

Now those look fun. Easy to walk in too as they are tied on.

[hhlvr72]

The desire to wear them is among my first memories.  I put them on for the first time around 6 years old.  My Moms were actually too big for me then but quickly outgrew them.   Been collecting and purging since!  Also very much in love with nylons!

[Pierre1961]

Fantastic Mum. 

And lovely shoes. Where do they come from? 

[SF]

I have always been attracted to gals shoes for as long as I can remember.  Why?  Who knows?  I have always found gals shoes and sandals to look nice and "prettier" (can a guy like pretty shoes for himself?) than boring guys shoes.  As I got older and more independent (teen years) I got bold and actually bought some gals flats that I wore discreetly.  When I went away to school, I began to wear gals sandals - flats - a lot, and no one cared.  

In 1995 I was shoe shopping and saw a pair of 2 inch kitten heel thong slip on sandals that I tried on, liked what I saw and bought the shoes.  I was hooked from that point on, unfortunately - ha ha.  When I showed my new sandals to my wife, she thought I was nuts, but eventually came to accept my fondness for heeled sandals.  

Now here I am many years later, still wearing gals flats and sandals and enjoying life.  Have fun all.....   sf  

[Histiletto]

I was already hooked on wearing a pair of black patent leather, buckle strapped shoes when I was at the ripe old age of almost 2. In the mornings after waking they were the first items I would put on for the days activities, because in my mind possession was ownership. Then one day my ownership idea was shattered, when my sister wanted to wear them for an activity we were going to attend. As a toddler I vehemently protested, as my buckle strap footwear was taken off my feet and given to her. From then on, my distrust in others taught me to be deceitful in order to satisfy my natural desire to wear my preferred shoes became regular, if not daily occurrences. Being caught and punished were only consequential formalities. When I was 3, my sister had out grown the footwear and needed to get a larger pair. Once I saw what had happened, I immediately went and got my favorite footwear and put them on, in spite of the objections. The buckle strap shoes and me became one. Only baths and changing clothes separated us. It was heaven on earth, because my most preferred desire was being satisfied and since I had shown others how much I wanted to wear them, surely they would replace them with another pair when the time came. My trust soon became distrust again when I was denied my footwear preference replacement. So I returned to being deceitful and secretive in trying to fulfil my desires to have and wear the now increasing styles of shoes I preferred. 

It was a year or 2 later, I saw my first pair of stiletto pumps and knew right away they were the footwear I would be wearing to satisfy my desires. From then on, when the chances to secretly wear my preferred footwear became available, rarely did these chances get passed up. These activities may not qualify as starts for wearing heels, but until I was on my own, these some times brief episodes confirmed I am a wearer of (high) heels or more to the point - stiletto pumps.    

Edited September 11, 2021 by Histiletto

[Shyheels]

I fancied a pair of go-go boots like those worn to school by this pretty red haired girl. I don’t remember what the heels were like, or if they even had heels - it was the overall lines of the boots that I liked. Oddly enough, it didn’t even occur to me at first that boots might be gender specific and so I nearly blurted out my desire to have a pair of those. Something tipped me if though, I don’t remember what, and I was mortified to find that I’d been coveting girls boots - and afterwards became distrustful of my judgement and tastes, watchful, and cautious. Many years passed before I opened myself up again

[pebblesf]

It seems like societal pressures did a number on many of us.   I remember my sister's red go go boots also...Put them on every time I was home alone....The strong desire to wear them and how they made me feel were more powerful than the "little voices" saying I shouldn't.  I don't know what I would have done if I was ever "caught".  Thinking back, maybe my Mom/sister did know, but let me be me....

[SF]

As a kid, I got "caught," twice.  I was probably 13 - 14 years old.  As long as I can remember I have been fond of gals shoes.  I saved up my paper route money and bought a pair of cheap gals sandals that I saw at a local drug store chain (Thrifty's for us older folks).  Fearing rejection or ridicule I hid the sandals and wore them in secret.  One morning when folding papers for my paper route, my mom appeared unexpectedly, and I was wearing my gals sandals.  We both were shocked.  Surprisingly she did not over react, but said that I should probably wear sturdier shoes when I leave for my route.  I did.  

Later she asked me why I was wearing the shoes, and other than I liking them, I had no answer.  A few days later she took me to my pediatrician for a visit.  The doctor asked me about the sandals blah, blah, blah.  Again, other that just liking the shoes I had no answer.  The whole experience was nerve wracking.  

Conclusion, I kept the sandals (mom never threw them away), and the subject never really came up again, I still wore gals sandals when the folks were not around, and as I aged and left home for school, I pretty much became a full time gals flat wearer and loved it.  Into my teens and beyond, I wore flat gals sandals around the family, mom, dad etc. and nothing was ever said.  A few years later I "discovered" heels, and never regretted it.  

As I have said before, I have no idea why I like gals shoes, it is the way I am, and I really like it....  Take care all, enjoy your flats and heels....   sf

[crossfire238]

So at age of 12ish….found my dads stash of porn and thought all girls should be in heels garters and hose.  So dipped into my mothers drawers and found all of the above, dipped in closet, found heels.   Wore them ALL… totL HIGH….

[SF]

On 9/14/2021 at 4:45 PM, pebblesf said:

It seems like societal pressures did a number on many of us.  

Ha Ha....   Don't ya know?  I have been fond of gals shoes for as long as I can remember.  As a kid and teen I "snuck" around wearing gals shoes and like you Pebble my folks knew, did not make a big deal of it but the "societal pressures" were there nonetheless.  I had the "little voices" too.  The good thing, as I grew older and became more independent / confident, the voices changed to confidence and compassion.   

The few times I have met other fem shoe wearing guys, we have had similar experiences, which to me is amazing.   Funny how us humans are "wired."  

Have fun....   sf

 

[maninboots]

I started wearing my mother’s boots at around 5 years old, as I got into my teens i used to smuggle them out for trips to town until I started work which was when i started buying my own boots, been buying and wearing boots ever since and I’m 58 next month lol, don’t think anything of wearing heeled boots out in public and couldn’t imagine my life without them 

[pebblesf]

19 hours ago, maninboots said:

I started wearing my mother’s boots at around 5 years old, as I got into my teens i used to smuggle them out for trips to town until I started work which was when i started buying my own boots, been buying and wearing boots ever since and I’m 58 next month lol, don’t think anything of wearing heeled boots out in public and couldn’t imagine my life without them 

One of the benefits of age I guess.  The older I get, the less I care about what others think...Or even more importantly, what I perceive others are thinking about me....

[hhboots]

Like many others here, I was young, probably 11-12, not only did I have mom's shoes but two older sisters.  I only really played around and wore them for short periods when nobody else was home, but that didn't last that long.  They didn't really fit me by the time I turned 13, and am not sure I was really hooked yet, it was a just fun little novelty at that point.

It wasn't until about 2 years later, 14, maybe 15.  It was my best friends sister, I had a huge crush on her, she was hot and wore fantastic 4 inch heels pretty much all the time.  I had a lot of sleep overs at my friends house and occasionally had opportunities to check out her closet, try things on, etc.  I wear women's size 10, and she had tons of pairs that were 9 and 9.5, many of which fit me just fine.  She had one pair of 4 inch white pumps that I am sure she forgot about, they were buried in the back of her closet, buried under a mountain of other things and were scuffed and not in the best of shape and I thought, "she wouldn't miss these", so I ended up taking them home (not proud of that), but that was really my first pair of heels and I was hooked now.

I still didn't have the courage to buy my own pair until I was probably 17 or so.  I kept a pretty small collection/stash that I wore mostly in private until I met my future wife, about 10 years later, who was very understanding and open to my experimentation.  Well, that opened the flood gates.  I wear heels more often than not, and my collection now is really just excessive and I have a hard time keeping it from just getting completely out of control.  She has occasionally expressed some unhappiness with it over the years, but for the most part she still supports my quirks   

Edited October 3, 2021 by hhboots

[SF]

Hhboots......   With understanding wives, we both are lucky guys....   Have fun....  sf

BTW, what part of the US are you in??

 

[pebblesf]

On 10/3/2021 at 12:40 PM, hhboots said:

Like many others here, I was young, probably 11-12, not only did I have mom's shoes but two older sisters.  I only really played around and wore them for short periods when nobody else was home, but that didn't last that long.  They didn't really fit me by the time I turned 13, and am not sure I was really hooked yet, it was a just fun little novelty at that point.

It wasn't until about 2 years later, 14, maybe 15.  It was my best friends sister, I had a huge crush on her, she was hot and wore fantastic 4 inch heels pretty much all the time.  I had a lot of sleep overs at my friends house and occasionally had opportunities to check out her closet, try things on, etc.  I wear women's size 10, and she had tons of pairs that were 9 and 9.5, many of which fit me just fine.  She had one pair of 4 inch white pumps that I am sure she forgot about, they were buried in the back of her closet, buried under a mountain of other things and were scuffed and not in the best of shape and I thought, "she wouldn't miss these", so I ended up taking them home (not proud of that), but that was really my first pair of heels and I was hooked now.

I still didn't have the courage to buy my own pair until I was probably 17 or so.  I kept a pretty small collection/stash that I wore mostly in private until I met my future wife, about 10 years later, who was very understanding and open to my experimentation.  Well, that opened the flood gates.  I wear heels more often than not, and my collection now is really just excessive and I have a hard time keeping it from just getting completely out of control.  She has occasionally expressed some unhappiness with it over the years, but for the most part she still supports my quirks   

Not proud of doing the same type of covert boot wearing while at friends homes....  Sounds like you have a great wife indeed...

[NrthEastHeel]

I Tried on first pair of heels in my teens. From memory they were a suede shoe, about 3 inch block heel. Just loved the shape and the height factor. Seriously started wearing heels almost daily in early 20's, which is when i started purchasing my own. Got more serious with stilettos then, usually from 4 inch high and working up to 5 inch, and higher with concealed platforms. Finding ladies shoes in my size has always been easy, i wear a UK size 5, sometimes a 6 for boots (small feet).