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shyguy

Members Stories :- What Got You Started Wearing Heels?

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My first time wearing "heels" started when I was staying at a cousins house. She had some burgundy shoes with a low heel, which I put on one time when curiosity got the better of me. I think the excitement of breaking a taboo (very strict parents on that score - boys don't play with dolls even action man, dress up in anything other than total male clothing etc.) and the weird feeling of being in some feminine article of clothing gave me a huge buzz at the time.

As I was often left to my own devices and my aunt was a very feminine dresser with lots of heels, I had the opportunity to go higher still almost immediately and I felt the need to, firstly with some cork wedges and then some gold stilettos with what seemed to the, only just pre-teen, me very high heels but were probably 3 inches or so. There was also an added buzz of maybe getting caught when trying these shoes on which probably kicked off an addiction to that buzz like an adrenaline junky.

So that was the first time for me which lead to the love for high heels I have today 30 years on...

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I had liked looking at heels for years before I got curious. My first time wearing heels was trying on my sisters white stilettos. The heel was quite low, but I still loved wearing them. She had a few pairs of heels and I used to put one pair on then put them into a different pair to make them higher.I would wear them as often as I could after that day.

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My first experience was when I was quite young...My sister had a pair of red go go boots...Couldn't wait to be alone at home, so I could wear them..It's been boot love ever since...

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I can't ever remember not having a thing for the flip flap sound of a mule slapping up against the bottom of a heel. My mother used to have some sensible height white wedge mules she used to wear in summer. I also remember a beige pair too, but I remember the white ones mostly, though I must be writing about a memory nearly 50 years old.

At the time, I must have been younger than 8, because we moved to a different house soon after. Not sure how I was left alone (people not so afraid to leave their children alone for 20 minutes then) but I got the chance to try the mules. I liked wearing them.

Several years later, I got the regular opportunity to try them again. Like hh4evr1 I too would stack two wedge heels together, one on top of another, to produce some height. Although I was quite young, I enjoyed wearing them more than should have been possible. In fact it was such a comfortable feeling, I wondered if I should have been born a girl?

When I started "dating" girls ('going out' with girls) and having a proper girlfriend, I realised I definitely had the right body. ;):D

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I also started by trying my mother's and older sister's shoes. I can't recall at what age or any particular pair of shoes I tried, but I remember when left home alone, I used to sneak in to closets to find shoes to try on. The same sneaking took a place when I was sometimes allowed to go to my dad's workplace with him, and while he was concentrating to his work, I was wondering around the office and locker rooms to find women shoes to try out. One particular pair I still remember, dark brown greenish knee high, with zipper and block heeled boots. What a sensation it was to try them! Size was perfect, they fit perfectly around ankle and calf, I was in seventh heaven when I put the boots on and pulled up the zipper first time. I think that was a starting point for me liking the heels on me, I can't recall any high heels from home, but those boots had maybe 2 or 3 inch heels and that feeling on my feet was incredible.

At the same time when I had the boots on and was walking around the locker room to get the feeling, my father had finished his work and was looking around for me. I didn't hear him coming, I was still in heaven and didn't pay any attention, but when I saw my father at the door, taking quick look on me, turning around in a way that can tell that he really didn't like what he saw, just mumbling that we are going home now, I think I also generated shame and guilty feelings for wearing the boots based on my father reaction. We never spoke about that later, I think my father just wanted to ignore what he saw. But it might have hit him later when I was openly cross dressing and my parents knew it as well, my mother took it very badly in a first place but my father was cool about it. I didn't realize it earlier, but most probably my father had an idea already. I think I was never caught by my mother and that one time only by my father, and I guess my parent never spoke what my father saw in that locker room... so he was somewhat prepared but my mother was not.

But the starting point was most probably the boots I tried on at the locker room. The sensation of perfect fit on size and everything, the feeling of the lift the heels generated... yeah, I call this event to be the moment when I started to like wearing heels.

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It's very interesting to hear how it all started for everyone, and some great stories coming in, let's hope some of the lurkers will jump in too.

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At the same time when I had the boots on and was walking around the locker room to get the feeling, my father had finished his work and was looking around for me. I didn't hear him coming, I was still in heaven and didn't pay any attention, but when I saw my father at the door, taking quick look on me, turning around in a way that can tell that he really didn't like what he saw, just mumbling that we are going home now, I think I also generated shame and guilty feelings for wearing the boots based on my father reaction. We never spoke about that later, I think my father just wanted to ignore what he saw. But it might have hit him later when I was openly cross dressing and my parents knew it as well, my mother took it very badly in a first place but my father was cool about it. I didn't realize it earlier, but most probably my father had an idea already. I think I was never caught by my mother and that one time only by my father, and I guess my parent never spoke what my father saw in that locker room... so he was somewhat prepared but my mother was not.

But the starting point was most probably the boots I tried on at the locker room. The sensation of perfect fit on size and everything, the feeling of the lift the heels generated... yeah, I call this event to be the moment when I started to like wearing heels.

Great report. While I'm sure it wasn't all that pleasant at the time, it's a great insight into how people respond to unexpected circumstances. Not just by them, but from you too. A sincere thank you for sharing. B)

I don't know if it's too early to be drawing any sort of conclusion from the stories so far, but two things seem common to all. Firstly, and inquisitive nature. "What's this, what does it do, what does it feel like?"

Secondly, a pleasant experience with women's heeled shoes at a fairly young (and impressionable) age?

I do know, or believe I know of an exception, and that might be Heelman500. If I remember correctly, he saw a buddy "dressed up", and had the suggestion made he might like to try on the dressees heels - which he did then try. Liking the experience, he got into heels. But that is (if I have remembered it correctly) the only instance I'm aware of, where someone got interested in heels as an adult, rather than as a child?

Other than that, it would seem to coincide with childhood experience?

I have the same situation with "Classical" music. Compositions we used to listen to walking into Assembly at my infants and junior schools, are the ones I can bare to listen to now, as an adult. Everything else is crap (to my ear :D).

.....

Edited by FastFreddy2

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Some good points there Freddy, I seem to recall a similar discussion on the other forums and that had a very similar kind of vibe i.e. most started at an impressionable age. It would be interesting to see what kind of jobs people did too, as it would seem to be logical that those with inquiring minds and who tried heels would also end up in jobs where inquiring minds were pre-requisite.

Also in the stories so far I have seen parallels to my own life experience with heels, i.e enjoying the feeling and wanting more, then maybe trying crossdressing and finding that the other female attire wasn't needed. It's all about the shoes ;-)

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My first experience was when I was quite young...My sister had a pair of red go go boots...Couldn't wait to be alone at home, so I could wear them..It's been boot love ever since...My experience was similar. I had a cousin who used to wear boots a LOT. She had at least 4 pair, and when we would visit, I would sneak into her closet and try them on. (I was a kid, so there was no problem with shoe size at the time)

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Some of my first experience with heels was, for me, not at a young age. My parents shielded me from the world, keeping me into this so called "Protective Bubble". It was only a few years ago that i started to let my mind wonder, then one day I remember seeing a pair of heel that i would have die for. they were amazing. =D . But, being me i didn't say anything, thinking to my self that this was weird and not right.

I was kind of paranoid at that time with what people thought of me, considering i was the odd one out. but then i found out about others who also wear heels, that stopped me feeling like the odd one out. eventually i got the courage up and when to the 2nd hand shop and bought my self a pair of boots, which ever time my parents and brother when out at the same time, I’d put them on and walk around the house. I just loved the look of heels, most of the shoes I found in the men's section just never really interesting to me.

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I was kind of paranoid at that time with what people thought of me, considering i was the odd one out. but then i found out about others who also wear heels, that stopped me feeling like the odd one out.

I would not be surprised to find many more feel the same way. I have heard about a fella who felt really bad about his interest, and got himself into quite a state over it. Like you, discovering his interest was more widespread than he could have hoped, produced a great deal of relief.

Not sure being different or an individual ["odd one out"], is so bad? In many forms of art, sport, and business, running from the herd is what helps make you successful.

We are what we are. Best enjoy it. ;)B)

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FastFreddy your memory has not let you down, it was indeed a few years back that as a forfeit for failing to complete a 40 mile charity walk, one of my mates had to go out around town on a saturday night crossdressed...

Now this lad is skinny as a rake, about 5'8'' tall and from the back whendressed... Well we had to leave one nightclub when some drunken neanderthal failed to spot the obvious...

At his suggestion I did try on the heels and that as they say was the first step, i have always been keenly observant of the female footwear and was always watching girls feet, especially on nights out! I guess it was a natural progression to move into wearing heels myself.

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FastFreddy your memory has not let you down,

Goodo! ;)

i have always been keenly observant of the female footwear and was always watching girls feet, especially on nights out! I guess it was a natural progression to move into wearing heels myself.

Ahh!

The 'seed' just needed some nurturing ..... ;)B)

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Goodo! ;)/>

Ahh!

The 'seed' just needed some nurturing ..... ;)/> B)/>

I guess it did need nurturing..... I think that if more of my previous partners had been high heel wearers that might have sufficed??

But to be honest I really doubt it

I have met one other chap in my hometown who is really into womens shoes,

I met him in a pub one evening and it was quite obvious that he was only interested in what the ladies were wearing on their feet, we had a good discussion over a couple of pints and it was quite clear that he never wanted to wear then himself, just to appreciate them.

I think that I made the switch from being a passive heel lover (on women) to being an active heel wearer as well!

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..... I think that if more of my previous partners had been high heel wearers that might have sufficed??

My personal experience suggests not.

With a single notable exception (a slim pretty girl of 5' 9" with the body of a lingerie model who couldn't wear a heel) all of my girlfriends have worn heels. Even the lovely Mrs Freddy, with a heel collection that would put ALDO, KG and many others to shame, there was no stopping the inevitable return of my interest. Possibly, if we went out more socially with her in a high heel, my interest may have been kept subdued. But that's a big ask from a middle aged couple, with one of them up for full-time work at 5.15am every weekday. I couldn't do that, unless I stayed up all night, as I sometimes do. (Apprentice vampire, me. No good with this 'up with the larks' nonsense. :D)

The fella you chatted to in the pub sounds interesting. I wonder, did he know what got him into liking the look of a high heel?

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Freddy

The fella in the pub was quite open to the fact that he had a shoe fetish. He was able to identify all the differnt types, the brands and had an opinion of all of them.... And the whether the shoe suited the wearer or not!

I know that he was very oppossed to the idea if men wearing heels, as to him it was all about the look of the shoe on the foot, and how it enhanced the female form.... Buy hey ho it was an interesting chat!

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I started by liking to look at heels on women before I tried wearing them myself.

I'm guessing that I was pretty much the same as you, it took trying that one pair on to make me realise that I liked wearing heels as much as looking at them.

What prompted your move into wearing heels, Rather than just admiring them?

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I know that he was very oppossed to the idea if men wearing heels, as to him it was all about the look of the shoe on the foot, and how it enhanced the female form.... Buy hey ho it was an interesting chat!

I've a lot of time for the same idea.

When I was younger, I used to go clubbing quite a bit. Unlike many other white men 'of the day', I could dance well enough to compete with some of my black friends. I remember well a little 'inter-town' competition we had at a club in Luton called Sands. We would go on the free night (or cheap night) that wasn't a Friday or Saturday, when most young people would go out for a drink and the chance to 'pull' other young people. We were there for the music and the dancing.

So the comp was friendly, and a laugh. Luton had a good girl dancer, we didn't. No matter what we did, it wasn't possible to beat a girl dancing, because she's a girl. It just looks better.

Same with heels I guess. Although I have more girlie feet than many girls I know, I'm a size 8, and I've got man shaped legs. Any heels I wear would most likely look better on a woman or girl, simply because they have a better (more aesthetically pleasing) overall shape.

I've never been into any sort of spectator sport. If I can't participate, I've no interest at all. My heels still look good though (or I wouldn't wear them), and they feel shedloads better than a flat shoe - which I don't enjoy wearing ever. I'd like to be surrounded by good-looking women with high heels, wouldn't we all? But as you drinking buddy will find as he ages, opportunities for such situations don't go on forever...... Unless your name is Hugh Hefner. ;)

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Right again on both fronts Freddy, I really do like the look of heels on women, but there are also some pics on the defunct highheelspassion site with men wearing heels that also looked really good and I have also seen some women wearing heels that 1. Couldn't and 2. Really shouldnt!

I think a lot of heel wearing is what you wear with the heels, I'm always wearing jeans or trousers as they go with heels and therefore you dont see my male legs..... Hairy, knobbly knees etc... Women look good in a variety of outfits with heels, but I am not keen on flared work trousers that hide the heels somewhat on women.

Also I am not a spectator and enjoy wearing heels, I don't think I wear heels anywhere near as much as you Freddy, but as I have found it is not something that I would ever willingly give up doing. I hope that when I wear heels it is not too horrendousand I do try to be discreet.

I also like working trains from the city either in the morning or evening rush hour, because there is always something to look at, and I always have a good look. Friday/Saturday evenings are also good, it makes me laugh when some girls can't even walk in their heels on the way out, let alone when they've had a few!!

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I don't think I wear heels anywhere near as much as you Freddy,

I'm not so sure. You 'wiped-the-floor' with me this weekend. ;):D

I also like working trains from the city either in the morning or evening rush hour, because there is always something to look at, and I always have a good look. Friday/Saturday evenings are also good, it makes me laugh when some girls can't even walk in their heels on the way out, let alone when they've had a few!!

I know it's completely unrealistic, but I'd gladly work your shifts to see what you see. Perks of the job or what? :D

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What prompted your move into wearing heels, Rather than just admiring them?

I tried a pair on and from that day started wearing them as often as I could.

I wore them indoors for years before finding sites like this for men wearing heels and after reading of men wearing heels in public I brought some block heeled ankle boots and started wearing them in public too.

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Freddy you can't have my job its mine all mine!

Seriously a really nice pair of heels IS normally the first thing I notice running into a platform, and the rush hour trains are best. I have noticed that Bolton for some reason is a hive of well heeled ladies!

Unfortunately the job where we got off in Manchester at 0820 has changed, there is one woman who Always wears really and I mean really gorgeous heels.

But there is still plenty to tantalise the eyes!

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Unfortunately the job where we got off in Manchester at 0820 has changed, there is one woman who Always wears really and I mean really gorgeous heels.

And unlike me, you weren't wicked enough to snag a piccy? ;):P:D

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No the company would be exceptionally displeased with me taking photos, a driver on another company got the sack for taking inappropriate pictures of women... Whilst on duty!

It's a thin line and one probably not worth crossing!

I will try harder when I am out to get some decent snaps

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