Members Stories :- Your First Time Trying To Buy Heels

[shyguy 15]

I remember my first time wearing heels, but they were someone elses and I didn't have access to them and sometimes felt the need to wear a pair of heels at home. The solution was obvious, buy a pair of heels of my own, but that had some drawbacks i.e. how does it look for a guy buying heels in a size which is probably his own?

I was young and did a lot of driving for my job, so I had plenty of opportunity to buy some heels away from anywhere I'd be known, but I was also very shy and self-conscious at the same time. Several times I stopped near a shoe shop and got to the door before walking away, probably looking very guilty. I stopped once outside a shop in NW London which had some great looking heels in the window and walked up to the door and inside. Once inside, with a dry mouth and sweaty palms I asked for a pair I'd seen in a size 8. Did the shopkeeper just look at me like I'd shoplifted or was it my own imagination? I didn't know, knowing what I know now he probably just furrowed his brow to remember if he had that size in that style. He didn't have my size so after all the build up I'd have to try again elsewhere.

Eventually I plucked up courage again, and went to a shop in West London which hadn't been open long but had some stiletto styles on display in the window. The shop emptied within a minute or two as I was browsing, then the shopkeeper walked over and started talking, and enquired as to what I was looking for. I swallowed and asked to see some black stilettos in a size 8 for my girlfriend (I lied badly). No go, they only went to size 7 and only in white at that time. Having plucked up courage to get this far again, I decided I'd give it a go and asked if they could be returned if they didn't fit her (the lie might still hold I hoped).

I bought a pair of white stilettos a size too small which I wore a few times when the need hit me. I couldn't keep them at home as my mum would clean my room while I was working so they were kept in my company car. I had to change the car after a year or so, so as I passed a skip one day I threw the shoes in as I had nowhere else to put them for the changeover.

So that's my long winded story, how was your first time buying heels?

[hh4evr1 18]

I don't think I was nervous about buying them as the first time I brought a pair of high heels it was near Christmas, so the sales person would probably have thought they were a gift.

I didn't try them on as the sales person said they could be returned as long as the receipt was kept. They were a black court/pump with a 4" heel.

Edited February 24, 2013 by hh4evr1

[FastFreddy2 282]

Background .......

I used to live near a school. My junior school close enough for me to go over our garden fence if I needed.

Only a year or two out of senior school, I saw a girl I was familiar with (might have been in my younger brothers year) walk down our road on the way to school wearing some high block heels. I nearly passed out! They were bought locally, I think from what might have been Freeman Hardy and Willis. I got an ex-girlfriend (who still liked me) to buy a pair in my size that I funded, saying they were for my new girlfriend. She may have known they were for me, it was never mentioned. At the time I was still living with my parents, but always had places to hide things like a pair of shoes.

A good ten years later when I had my own place, my then 'live-in-girlfriend' (hairdresser with an eclectic attitude borne of eclectic experience from working in a salon) went to Covergirl in Upper Street Islington circa 1984/85, and came back with some courts with a 6" heel. A shoe I only sold about a year ago - BTW......

The first shoes .....

Some time after that, but only months after, I visited the Covergirl shop with my girlfriend. For those of you who aren't familiar with the establishment (now long gone), it was a traditional "costume" shop specialising in men dressing as a woman. Their shoes were made by The Little Box, found only about 500 yards away in Holloway Road. Over several visits to Covergirl I bought 2 more pairs, this time with surprisingly wearable 5½" heels, again that I only sold 7 or 8 months ago. [All three pairs, now too small, since I've gained weight and my feet have spread.]

I also acquired some white courts bought locally, from I think Bally that had a more dance friendly 4 inch heel, for wearing out (with my girlfriend) when we used to go to nightclubs like The Mudd Club in Charing Cross Road. It was run by Phil Salon, who was known to be a very good friend of Boy George. This might have been around 1988/89 or a year earlier. Toward the end of 1989, I retired from "dressing up" as I moved back to my parents. This dressing up incidentally, was a means to an end, the 'end' being I could wear heels out socially.

The next pair I bought was from the London Fetish Fair, when it actually was, a fetish fair. I bought a his and her pair of black patent platform sandals (mentioned elsewhere on the forum), around 1997. They had not stored well, and were thrown away last year.

The next pair I bought and wore, where some over-the-knee boots from Priceless. That would have been around January 2008 or just before. I'm sure I was with Mrs Freddy at the time. I don't honestly remember who took them to the till, but it wasn't long before I took them back (faulty) and had them replaced FOC, while on my own. The second pair weren't off my legs for about a month, by which time I'd worn them out.....

By about April of that year, I was trying on shoes in stores like House of Fraser Lakeside. I remember vividly, asking a middle aged lady for the other shoe, of a style of Diesel courts I'd fallen in love with. She brought the other shoe for me to try, without batting an eye-lid. The fitted, and I bought them. I didn't keep them as they wouldn't stay on my feet, but they were and are, stunning to look at. Around the same time, (I think) I also tried on a pair of ALDO black patent courts in store, again at Lakeside. Neither the girl who got them for me to try on, nor Mrs Freddy, understood why I didn't buy them. They fitted well, and I could walk in them. I had decided I would have them, but would wait until I could get them in a sale. Took two years, but I do own some I got at a better price than the then asking tag of £50.

There are few shops I haven't tried girls shoes on in, but do it much less these days. It's a challenge I've met, but now feel less inclined to 'prove' myself, even when offered a pair to try on by a helpful shop assistant recently (who plainly knew they were for me). I'm less worried about myself than I am about embarrassing shop staff, and their customers. And returning shoes, if I need to, is a great excuse for a second outing.

..........

Edited February 25, 2013 by FastFreddy2

[Jinx 12]

My first time shopping heels just for me... hmm... it must have been around 20 years ago, and I must admit that I don't remember great details, but at that time I was cross dressing and I was buying women's clothing and shoes openly and without any hesitation. I got lots of shoes from second hand shops, but some I bought from shoe stores as well.

One particular pair of boots I remember, I think I still have them somewhere. I went to shoe store with my (that time present) wife and for some reason at that time I didn't try the boots on, just bought them based on size on the shoe. And of course they didn't fit, so back to the store. This time alone, and that time I openly told that boots are for me and I need them probably one size bigger. Sales girl went all red face and almost panicked and she was in real trouble with the situation. She was looking around the store to see if anyone noticed me and my boots I had placed on the desk. And this time I also wanted to try the new size at the store before bringing them back to home. And at that point sales lady almost fainted so mostly for her comfort, I asked if I can use back room for trying on the boots, and she was ok with that. So I tried the boots, noticed the sales lady checking me trying on the boots and turning away again red faced when she noticed that I saw her peaking from the door. I really don't know what was going on with the sales lady, but I bought the right size boots and left the story without second thought.

Later on my cross dressing fainted and most fade away, but love for the shoes kept growing even stronger, and in one point I realized that is was actually the shoes why I was cross dressing in the first place. That was quite big relief, even I was very serious about dressing and putting full effort to look as feminine as possible. Today I put a wig and makeup maybe once a year, usually for some costume party and that fills my inner need to be in full drag and show my feminine side full open to the world. Otherwise it's just about the shoes, being man who just happens to like shoes with higher heel.

[FastFreddy2 282]

This time alone, and that time I openly told that boots are for me and I need them probably one size bigger. Sales girl went all red face and almost panicked and she was in real trouble with the situation. She was looking around the store to see if anyone noticed me and my boots I had placed on the desk. And this time I also wanted to try the new size at the store before bringing them back to home. And at that point sales lady almost fainted .......

I think I've possibly once experienced a bit of obvious reluctance, but nothing like this. I would have assumed the sales girl was maybe 15 years old, but "sales lady" doesn't sound like a junior person at all. Maybe she didn't get out much?

I've mentioned only a couple of months ago, a young twenty-something (20/21/22) year old girl assistant, had offered me a pair of high heeled shoes to try on while I was in a busy high street shop. They were labelled UK9 (though same fit every other brands UK8) so there was no doubt who they were for, and she did actually say; "do you want to try them first?" With one shoe in her out-stretched hand, offered at me to take.... Obviously I don't look as 'manly' as I think I do.

Later on my cross dressing fainted and most fade away, but love for the shoes kept growing even stronger, and in one point I realized that is was actually the shoes why I was cross dressing in the first place. That was quite big relief, even I was very serious about dressing and putting full effort to look as feminine as possible. Today I put a wig and makeup maybe once a year, usually for some costume party and that fills my inner need to be in full drag and show my feminine side full open to the world. Otherwise it's just about the shoes, being man who just happens to like shoes with higher heel.

With a single (recent) exception, I haven't 'dressed up' since about 1989. No need, as I had a busy life (career) that kept my shoulder hard to the millstone. Now, I probably still don't have a need, as I pretty much wear heels whenever an opportunity presents itself. The exception was about 5 months ago, when I met up with someone into REALLY high heels, who said they would be "dressed" when we met at their home. Think I wore a foundation, jersey dress, and a wig I'd owned since around 1985. Plus a pair of knee boots with 5" heels. Was okay, but didn't produce the excitement it once did.

As before, it's a means to an end. I'm only tempted to 'dress up' so I can wear some of the more feminine shoe styles I have in the collection, which include some black patent courts with pencil thin heels. I have in mind to wear these somewhere regardless, but it's finding suitable venues.

.....

[Jinx 12]

I would have assumed the sales girl was maybe 15 years old, but "sales lady" doesn't sound like a junior person at all. Maybe she didn't get out much?

Nope, she was older them me at that time, maybe 30 something.

I didn't pay that much attention for her, just remember how strange she behaved.

Was okay, but didn't produce the excitement it once did.

Double that. It is still fun to go 'all in' time to time, but the excitement and that inner satisfaction it used to bring is not there any more.

Stepping back to shoe shopping experiences, it is somewhat amusing that younger days I had no trouble going to shoe store or any shop carrying women's only clothing and lingerie and everything, and without any hesitation was trying out shoes, dresses, etc. even I was shopping in man mode. But later on, when things evolved from cross dressing to using only high heels from the 'wrong side of the aisle', my brain generated great grand wall of shame and hesitation for shopping the heels. Go wonder. And I had to build up the courage from ground zero again to be able to try on the shoes in the stores and to go our bravely being me.

I've came out to conclusion that when I was younger and doing CD thing, it was sort of 'on you face' type of approach and sort of youth rebellion against norms and rules. And when gained years, it became more of trying to blend in and seeking acceptance...

[miltboot 2]

Since I have a larger shoe size, I never had the option of going the retail route because the stores didn't carry heels in my size. All off my boots have been acquired through mail order. I guess it has made the first time more comfortable for me because of the "privacy" factor.

[shyguy 15]

The coming of the internet and the option to buy online has certainly made buying shoes much easier. These days I can just find a style I like and order it to try in my own home, and the well known auction site also means many more styles at bargain prices. Sometimes it's hard not to buy shoes these days.

[FastFreddy2 282]

Sometimes it's hard not to buy shoes these days.

Very very hard.

I have plenty, many I'd like to move on. (Sell.)

Doesn't stop me looking, nor being tempted >> clicky <<

If link doesn't work ....... £95 in sale!!

Edited March 1, 2013 by FastFreddy2

[shyguy 15]

You have expensive taste in shoes Freddy ;-)

Almost back on topic -I can also remember the first time I bought shoes online, and having to show them to Mrs Shyguy (not a great supporter of me in heels even now but then it was real tough) so she would at least know what was going on. After the initial debates and an agreement that I could order, just to try on, some heels from an online catalogue the deed was done. Another buzz when I got home to a stern looking wife with a parcel and the words "this is yours". I went upstairs and unwrapped a pair of stilettos and put them on. A huge buzz and that same feeling I had the first time.

I still have them now..