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I've enjoyed the feel of wearing heels since before I was 8. [Exact dates, difficult at my age. ] Later, when I went from boy to man, I realised I really enjoyed both wearing heels, and seeing them worn. Since I'm not stunningly attractive, I've always thought clothes and personality were as least as important as basic looks. And looks (for me) didn't need to go much further than 'clean and tidy'. For a girlfriend, tidy with a bit of makeup maybe perfume, always a plus. My then girlfriend bought me some high heeled shoes somewhere around 1984 I think. After that, I bought myself a couple of pairs too, and the two of us went out with me in heels to [mostly] fetish clubs. We did go to some mainstream clubs, but Boy George was regularly on TV/in the music charts/on the front cover of most womens magazines, so the androgynous look was not so unusual. Wearing high heels was very natural for me. I don't mean I'd gotten plenty of practice, but I put them on and walked 'gracefully' like you might expect a girl to. I could [can] straighten my legs while wearing them, and to a degree, sway my hips in higher heels. [Just like girls do.] Jump forward 25+ years. It had been some time since I had worn heels. I still had my older shoes boxed and stored at home, but they never saw daylight. My feet had grown [as had my weight] so they weren't that comfortable anyway. [They were all a small 7 except the silly high ones which were a 7 1/2.] One drunken New Years Eve, I'd gotten in my head I wanted to wear heels. When we got home (me somewhat the worse for wear still) I put on a pair of Mrs Freddy's size 6 reject ankle boots, and went out walking. I had to be a bit careful as there were other revellers out, and I was walking around the streets I lived close to. I got home just before daybreak, and quite sober. I hadn't realised, but the shoes had cut my skin and I still bear the scar from that night. Within weeks I'd bought some new heels, and wore them at home and out late at night. They were both stunning to look at, very tight stretchy OTK boots that were quite cheap, but were just wonderful to wear. I bought several pairs, and wore out the first pair in about 6 weeks. They were never meant to be used as hiking boots around poorly maintained pavement. I was lucky in that within two months I'd found HHplace and went to the World Heel Meet [WHM] in London. I walked in broad daylight, from a car park close by, to the venue in 4 1/2" heels. When I walked back, I stood around and next to a family group, and no one spotted my heels. A few weeks later, I went to a shopping Mall in some 4" rubber wedge heels. I was very self aware, and spent a lot of time looking for those who might be looking at me. I got 'noticed' by one or two women, but no finger pointing and no loud ridicule. The rubber heels were very quiet, and drew no attention. I returned to the Mall regularly, always in heels. More recently my love of heels has waned. I've had personal health pressures, a newly acquired home to deal with so poorly built it needs knocking down and rebuilding..... Too many funerals in the last two years...... My taste in heels has matured a little too. At the time of the WHM it was stiletto heels or nothing. I now wear block heels during the day as they are much less likely to draw attention while out. If it's dark out, I'll be in high-ish stiletto's, most with fairly thin heels. Despite the real threat of them going into cracked pavements. I've been out locally in heels at night with varying success. Noise from heels being the main point of interest to those I'd sooner weren't noticing. [i have a particularly quiet time and place in mind.] More often than not I'm wearing heels in noisy/busy venues were people are usually too wrapped up in themselves to notice my footwear. Sometimes I'll walk where it's not busy or noisy at all, and I just carry on as before. My venues are selected. I have, despite my reduced interest, a continuing pledge to myself that I'll wear heels every and any time I can. I've probably lost 30+ years of heel wearing, and do not want that number to increase. Health and opportunity will make my heel wearing career short enough. In the past, when I was an active member of HHplace, I spent a lot of time enthusing fellow heel wearers to try to wear heels out when they could. I often tried to get groups together to walk out in heels, usually in darkness, though not always so. It's my belief that we all do stuff that is 'normal' for us. I've managed to see wearing girls shoes as normal, or more accurately, "usual". I possibly haven't changed the attitude of a single other person [ie woman] about it, though I've now several people I meet who don't bat an eye when they see me wearing heels, I'm hoping to increase the number as time goes on. There has never been a time in my life I've felt compelled to do something, and not done it. True, there haven't been many of these, but I don't feel frustrated at not being able to do something I want to do. [Living to be 200 years old is likely going to defeat me though. ] For this reason, I've never understood why anyone else would be any different? I'm not being hard arsed about this, I just think our lives are too short to not indulge a core interest. Only yesterday, I was talking to Mrs Freddy about Mr Freddy's funeral arrangements, and what shoes I'm going to wearing in my box. Apparently I've got to sort that one out myself, but it is on the agenda to do. With few exceptions, the "life's too short not to" motivation doesn't appear to have an effect on men who are interested in wearing heels. [Maybe not until their later 'mid life crisis' perhaps?] I'd have to say I've always felt this pressure, since my first 'near miss' in a car accident..... Certainly for me, the thought of being too old or sick to change how I live my life is a constant pressure to live the life I want, rather than lead the life I'd like to have. [The optional parts obviously. Few of us could afford to live on a cruiser sailing around the Mediterranean for most of the year.] I'm evangelising about the benefits of wearing heels obviously, while [still] being fit enough to do it I suppose, and using some of the detail of my own personal journey to illustrate it. So far, even when I've been clearly spotted wearing heels, there's been very very very little adverse reaction. This won't be the case for everyone in every situation, but it would seem the first hurdle [of several] to wearing heels out, is ourselves. Building our lifestyle to accept that wearing heels in public, is normal [usual], is probably the biggest hurdle. This will be because we are are all more comfortable doing things we are familiar with, being places we are familiar with, so less comfortable doing anything for the first time. Or uncomfortable until the change becomes the regular/normal thing to be doing. Has the opportunity to wear heels out lessened the excitement/pleasure of wearing them for me? Possibly a tad, but I still feel wearing heels out is a pleasure I don't want to lose. I just love wearing a heeled shoe. Lastly, I'd say it's got to be easier having a partner who can be supportive in an outdoor adventure, by encouraging or better yet, by taking part. But taking part is a big ask of most women, it's an act of bravery difficult for some men. Good luck to you all. Anyway, the pep talk is over. Reason for edit: Grammar. ....