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How did you buy your first pair of heels


Heel_Boy

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I actually found my first pair in a multi-storey carpark. Someone had presumably bought a new pair of shoes and on their way back to their car had thought "i may as well just leave these old ones here rather than taking them home just to throw them away". They were black suede with approx. 2 1/2 inch heels. Nothing special and a bit beaten-up but 'owning' them was a milestone (of sorts). The first pair acually I bought, I spotted in an Age Concern charity shop. They were stunning 4 1/2 inch black patent stilettos. I had been dragged into the shop by my parents during a dull saturday afternoon shopping expedition. I went back later that week to buy them (after agonising with myself over it!). They were still there (phew!) and priced at a very reasonable £3. Unfortunately, I decided to throw them out when I moved house as I couldn't think of a 'safe' way to move them without chance of them being discovered by my girlfriend. :smile:

Always High-Heel Responsibly

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Bounced into ASDA (Walmart for the non uk members) at 6.30 in the morning on my way to work, nice and quiet, chat line at the till from the staff "we do sell quite a few to men ,- wink" I felt like an 18 year old. I think I half caught a sour comment from the old guy behind me, but he can think what he likes!

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my first pair i bought was for my gf and i tried them on and they fit tight so i had an idea what size to buy so i went to a shoe store and bought some without trying them on in the store and had to take them back the next day saying my gf couldnt wear them . so i then went to the same name store but in a different part of town and the girl there kept asking if i was ok and i told her yes. when i went to pat for them she said do they fit i told they were for my gf , she said it was ok if they were for me . she was ok with me trying on heels and said i wasnt the first the first guy to try on heels . so i go to that store all the time and they have heels in my size 12 .

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The first pair that I bought was in a self-service type of women's shoe store that was in a stand alone store. Unfortunately, the chain is no longer in business and I don't remember the name but they had nice stock.

I wanted to buy a knee high size 10 (US) white stretch boot, very nice style in the '70s. Unfortunately, they didn't have my size (actually not even close because I take a large 11 - but of course we didn't know that then). So instead, I bought a beige stretch boot, size 10. I can't tell you how very, very nervous I was but at least, 30 years later, I can tell the tale with a big smile! And I paid cash at the register. Come to think of it, the cashier was quite bored as I was the only customer!

As US 10 is too too small, they looked good but after about 10 minutes or so, they had to come as they were too too tight.

It's all about the heel!

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I always liked looking at the girls having fun with their heels and enjoying wearing them, so one day I decided that I would like the thrill of wearing heels too. I hopped into my car and went to a shoe store, walked in and picked a pair that I liked, payed for them and left. That was the start on my crossdressing adventures. Cheers--- Dawn HH

High Heeled Boots Forever!

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  • 2 weeks later...

My first couple pairs were long term "borrowed" from a GF and from my sis. :winkiss: (not too proud of that, but I had no spare shoe hobbie money in my early teens and the urge was just too strong to see the wrong in that)

My first bought pair was from Payless when I was about 17 and I was nervous as hell. I planned it when I knew it was a slow time for them and had to take a pre-purchase quick scanning trip there to find what I wanted exactly and then when I finally commited to buying them I was in and out like the wind. :nervous:

These days, the internet is my primary shoe store, but I have ventured in a few stores recently to shop for heels. Not as nervous about it anymore, still some hesitancy lingers all these years later though.

hhboots - I have a similar story. I bought my first pair of boots at a resale shop. Made a pre-purchase scanning trip then walked in the next day, picked up the boots and walked in and out like the wind. All my other pairs were purchased through the Internet.

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I can't recall how I actually got the cash to buy my first pair, but back then I would do all kinds of jobs, mostly yard maintenance. At maybe, 75 cent to a dollar an hour, I'd work under the desert sun, during our summer vacation period out of school. When we were attending school regularly, I would work some weekends doing the same kind of yard work. After the day's work was done, I'd stop by the local "Dairy Queen", if possible, and get the largest chocolate milkshake they had with a straw, to make the trip home bearable and worth the day's effort. Back then the cost of a milkshake was not quite an hour's wage. As far as buying my first pair of heels, I've told most of it in another thread. A week or so before my first purchase of heels, the school period was to begin the next week. My dad brought us to the store so that we could get the clothes we needed. While the others were busy picking out what they wanted, I wandered over to the shoe department, because I had noticed their display had some high heels that I had to get a closer look at right then. Of course, I was pretending to look at the boy's shoes, which were near by. Once I saw the 4" white patent stiletto pumps, I knew I had to have them. I wandered back to where my brothers and sisters were shopping for their school wear and discovered they would be going to the shoe department, soon. I can't remember who all needed new shoes, but I did talk to my mom about getting the heels (I secretly wanted). She declined, so I had to figure out another strategy. I had a bit of money put away from the odd jobs I had been able to do. I didn't have quite enough right then, but that weekend I was to get paid for a janitorial job I recently obtained on a regular weekend basis and the rest is a history you can finish reading about in the Everybody section under the heading of "Age you WISH you started wearing heels?".

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