The first pair of heels you wore

[shoe-ca]

My first time in heels was not until I was in my 20s and living on my own. The desire to wear them had been there for many years but being a tall guy who needed a women's size 12, it wasn't like alot of opportunity presented itself with them women around me. With the advent of Ebay I finally saw an opportunity to explore my interests and I bought my first pair of black heels. They were a thicker heel, 3 1/4 inch, but sliding them on that first time was incredible. Sadly those shoes are long gone, but they had a ton of miles on them and were so comfortable once I had broken them in. Needless to say that was just the beginning

[thomas]

All though i never started wearing until i was married.I allways had a thing for womans shoes and riding boots the feel and the like of leather.My sister had a book of a girl who had these white kneehighs boots on i was so taken by thoses boots i was always looking at that book then there was the comicbook Archie and Jughead this one particular story line had a girl in a pair of hheels.ah.Now one of my twin boys when they were 3 or so he use to put a shawl on then a pair of 1in heels the ones that Dorthy wore in the Wizard of Oz than walked about the house in this getup.I use think these was funny but now my this is the furture

[SleekHeels]

The very first pair I wore were my mum's 4" black suede peeptoes when I was 5. I used to sneak them out of her room and secretly try them on. Just a very happy feeling. After 2-3 years I guess I must have outgrown them and couldn't wear them any more.

Then when I was 11 I was walking home from school one afternoon and I saw a woman at a bus-stop wearing white 3" or 4" heeled slingbacks with long thin straps that tied around her ankles/calves (lots of girls were wearing a low-heeled version in lots of different colours at school in the 80's - I fantasized they'd send all the boys home but let me stay and wear those shoes too, but that's another story). I searched every corner at home until I found my mum's gold patent slingback ankle-strap sandals with a 4" heel, and that was the first pair I learnt to walk properly in.

What is most fascinating about the comments here, is that it would seem that the 'first steps in high heels' seem to be the same for both girls and boys. In fact there is a common 'secret' aspect to both sexes initial experiences of high heels.

Many of you have posted about 'borrowing' your Mum's, Sister's or other female relation's high heels, and I have to say that it's the same for girls. After all, what other role models did any of us all have?

That's a really interesting observation, and to me it's always been really heart-warming to feel that sense of affinity (rather than the whole "Mars-Venus" thing that treats us like we're different species). Like you say, it's about "role models" and aspirations. That also makes me think of the first heels I ever bought, 4" black patent courts at age 17, and the feeling that they're my high heels.

[johnieheel]

My mom's red 3" pumps. I was 3.

[dww]

I think I bought my first pair of heeled shoes at about the age of 17 after I started working. I did buy a few pairs of flat type girls shoes before that with my pocket money. My mums shoes never interested me, but I did wear a few pairs of my sisters that had heels, she was the same size as me for a while.

[fatfuzz]

The first pair I wore were some 1" pointy courts that belonged to a cousin and I can't remember what the first pair I bought to wear were like. I just remember that they were all way too small for a while til I discovered the Internet and Barratts shoes...

[legs777777]

Hi All. The first pair of heels I ever wore were my sisters black sandals, strappy ones with a 4 inch heel and a small platform, wore them as many times as I could till I eventually took them for myself anyway. Hooked by then, Very eary age too. I also remember the first pair I bought, red leather court shoes with a 5 inch heel, waited outside that store for hours plucking up the courage to go in and but them, at 16 years of age it was as expected, very emmbarrassing, but what a buzz eventually getting them on at home.

[ctdans]

As with many it was whatever I found in my mom's closet. I have no sisters. My first "real" heel was 4 inch or more that I bought when I was 18. I remember my pulse pounding as I went to the register and the guy said " these for you?" I said yes and he said no returns pal. They were red patent pumps that I wore out!

[kikepa]

A pair of fur-lined Italian boots, with heels of aprox 3". Mom kept them in the center front closet, so they were always at ready access, and being a latch-key kid, I'd wear her boots for 45 min a day until mom and pop got home. Over the next several years, I grew through her shoes. So, I was on my own.

[christine_c9]

Wow ... a lot of guys wearing heels. Of the 39 posts to this discussion only 1 is a girl (not counting this 40th post of mine). My first heels of my own were a pair of white slides with cross-over red and blue (seriously) toe straps about 1/2" wide when I was 14 and I begged my mum to get them for me and then I tried to wear them to the local agricultural show which was sort of fun but sort of a bit of a disater. The show and sideshows were on a grassed oval ... not the best for heels, especially when you are not experienced in heels. My two friend had worn heels too. In the end it was fun and that was the main thing. These were not the first I had worn as I had worn friend heels before this. Christine.

[SF]

Like most other posts here, it all started at an early age (would these stories make an interesting study for psychology graduate student?? ha ha) My story, since a teen, I have always liked and worn girls shoes, mostly flat sandals. Not sure why I had this attraction to womens shoes, other than I liked the look and style and always wanted a pair. I wore sandals when alone, and hid my "collection" from my brother and family. When I went away to college, I beagn to venture outside and wore the sandals to class and everywhere else (this was in the early 70's). To my surprise, no one then - and to this day - has ever commented on me wearing flat womens sandals! In 1996, while travelling overseas, I noticed that most all of the women wore wonderful high heel sandals. The shoes looked so classy and elegant. There were all different styles, heel heights and materials. Some of my travel companions even noticed and commented on the shoes, and the gals that I was travelling with bought several pairs. I still have fond memories of seeing all of those high heel sandals. Several months later, after I returned back to the U.S., I was "shoe shopping" as I always do, looking for some flat womens sandals for the summer. I saw a pair of black slip-on thongs, that had a braided upper and a 2 1/2 inch "kitten type" heel, and they were in my size ( I still have those shoes!). They reminded me of some of the sandals I had seen overseas. I tried them on, they fit, and the next thing I knew I was in line making my purchase! I had NEVER thought that I would ever be caught in public wearing a pair of high heel womens sandals, but boy, was I wrong. When I got home I showed my new shoes to my wife and she laughed and thought I had gone nuts. Since then she has become quite comfortable with me in heels. From that summer day in 1996, I have become a regular wearer of high heel sandals (although like many here it DID take some time to get the courage to venture out). I now have about 30 pairs of heels and wear them out quite regularly. Why do I like womens shoes? Don't know, but I like it. I guess I am just different. And I a glad that my wife is OK with it too!! Have fun.. sf

[ilovepumps]

I was 19. I was always sorta fascinated with pumps, having sisters who owned them. When i hit 19, i suddenly became a high-heel pump lover. One of my sisters had some yard sale stuff in our carport, in boxes. I found a pretty black pair of pumps in the box. I took them inside to my bedroom. They were smaller than small, so no chance of getting them on my feet. I was still touching them, smelling the leather scent, and loving the almond-toe shape of them. I wanted a pair of my own. Near my school, i kept seeing a corner shoe store. I made a vow to myself that i would go there and buy a pair. So a short time after that, i went by the store and bought a white pair. They were vinyl, made in china, but when i got them home, and put them on, i felt like i was walking on air. It wasn't long before i bought more, and more, and more. I have almost 100 pair of pumps now, and i don't plan on stopping! I want more, more, more!!

[brake blocks]

It was the same here, wearing mum's shoes a black pair of 3 inch stiletto heel strappy sandels from Bally. This would be around 1974-75, i don;t remember why but i asked her if i could wear them, the answer was yes but only in the house! that was summer time. In 1980 i started work and earning my own money i started to buy from Freeman Hardy & Willis. at this time most of the heels from them were round shaped metal tipped stiletto's & burgendy coloured they were around £15.00, i think & the shop assistants did not even bother in them days. I did buy quite a few pairs at that time. when it was my 21st one of my female cousins were wearing the exact style from Freeman Hardy & Willis, as i had hidden away. in years to date my then girlfriend now my wife was told by my mother about the heel wearing, and the girlfriend had me over at her house when her parents were out and had sorted out a pair of kitten heels for me to wear! That would be in the early 90s. We have not been there since. It would be nice to do that again,

[hhboots]

I don't remember which of these was first: there were my older sisters, my mom, and my best friend's sister (when I did sleep overs at their house) - all of which owned wonderful heels that I was happy to slip into around the age of 11-12.

[Gogoboot2000]

The first time was when i was about 11. It was my mum's kneehigh 3-3,5" black leather boots. The heel was squarish and laminated (wood?). I wore them as i often as i could until they didn't fit any more. I wonder what eventually happened too them, i think she had them 20 years or so. I never wore her HH shoes and her flat heeled everyday boots were not interesting either, although i did use them some times.

[XtremeHeels]

The first time I wore heels was when I was around 5 years old. I really didn't think much of it at the time though. However, when I was in elementary school one of my teachers wore stiletto heels every day in class (4-5 inch stiletto heels) and I was hypnotized watching her in them. I wondered how she was able to walk in them all day and was very curious how they felt. One day after school I secretly took a pair of my mom's heels from the closet and tried them on. They had a 3.5 inch stiletto heel and fit perfect. Once I had them on my feet and admired how they looked on me I stood up in them and the feeling was incredable! I took a couple steps (wobbling around of course) but from that moment on I was hooked. I started wearing them as often as I could and got great at walking in them and just had to go higher! The rest is history:smile:

[w6ish]

awesome first time stories! hope to read more from other members.

[heelman83]

I was around the age of 13 and I always loved heels and wanted to try them for myself. My sister was older and did not live in our house and mom did not have heels so I had to find some. I went to sears and tried on a white pair of 4" heels, I bought them. Those are the first heels I remember wearing. I loved those heels! Eventually I started going higher and higher. When i turned 18 i got to try a pair of 8" heels those were amazing!

[Schnubab]

Im sure my story is a lot like most guys. As a child I was always amazed by my mother's ability to strut around in her HUGE collection of heels (seriously, she had so many shoes that she had pairs in everyone's closet in the house). She always seemed to have a walk about her that just radiated confidence. Eventually, when I was about 10, my mother had decided that she needed to keep a pair of black, leather and suede, knee-high stiletto boots in my closet. I had seen her in them before and was instantly captivated by them. I couldn't wait to have the chance to wear them. Later that night, sure enough my door was closed and I opened the box with such anticipation that I was shaking. As I zipped up each boot, I knew where my mother's confident stride came from. I lay back on the bed and admired the boots for the rest of the night. Needless to say, I was only happy to have my mother keep more shoes in my closet:silly:

[kikepa]

I was around 5 or 6, and while looking for one of the board games in our front hall closet, I came across a box with two pair of boots in it. One was a simple pair of rubber galoshes, but the other was a pair of leather stiletto-heeled winter boots. I tried them on, and walked around for a minute before putting them back. I didn't play around with my mom's heels at that age, but I'd occasionally wear the boots. About five years later, I was at a neighbor's house with my mom, and while she and the neighbor were talking out back, I snuck into my neighbor's closet and began trying on her heels. They were a lot smaller than my mom's and fit me perfectly! For at least another year, anyway. About three years later, I finally grew into my mom's shoe size and would wear them after school for a couple of hours until shortly before she'd come home from work. That lasted two years. I never wore heels while in high school. It wasn't until my third year of college that I regained an interest in wearing heels, and I had a couple pair I'd wear staying up late after my roommates went to sleep or when they were in class. Since then, my interest has been fairly steady.

[ELECTRIC]

I remember when I first wore high heel shoes. I was staying at my aunt and uncle's house for the weekend. They went out for the evening and my aunt had left a pair of her pumps in the hall way to their bed room. I was curious as to what it felt like to wear them. They were the classic black pumps with 3-1/2 high heels. I put them and it was the most wonderful feeling in the world. The shoes were soft and very comfortable and I felt very tall wearing them. I though it was amazing. Of course walking around in them took a little getting used to but I did get over the wobbly walking. After going over to their house several times during the summer, I would go to my aunts closet just to wear her heels, when both aunt and uncle were not home. It seems she never wore them much as they were always in the same place. So the last time I was over at their house, I took her heels and put them in my suit case when I went back home. If she ever missed them, she never said and I never heard a word about it. I now wear only classic high heel pumps as much as I can and own several pairs. It seems there are not enough words or adjectives to describe how wonderful it feels wearing these wonderful high heels and more men should wear them. I see nothing wrong with it and wear my high heels with pride.