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I would say that my "fascination" with boots and heels began when I was just a little kid. I have often wondered if this "fascination" is something I learned, or was I hardwired this way. Unfortunately, I waited until my late 40s-50s to actually allow myself to admit that I wanted to wear high heel boots and get some.... It has taken me many years since then to develop the courage and confidence to wear them in most any setting these days without the usual self imposed negative feelings. Thanks to all my friends here for your help. Don

Although I've had a fascination with heels since childhood, I did not actually start wearing heels for real until age 44, in 2012. I started with clogs before that, but the first time I wore shoes with an obviously elevated heel was in May of 2012. They were also clogs, but with about a three inch heel. I stuck with clogs for quite a long time before I tried some other styles, and today I will wear just about anything that I find attractive.

I acquisitioned my first wife’s shooties (shoe-bootie) one day in the late 70’s because my dress shoes didn’t look good with the suit I had on. I was in my early 20’s. They became my dress shoes until I wore them out in the late 90’s. Great leather shoes with a 2.5 inch heel. Then in about 2008 I needed water shoes for a trip to Hawaii. They ran out of men’s in my size. So, I tried the women’s size 10 and the men’s size 10. To my surprise the women’s size ten fit better than the men’s size 10. In 2011, I researched shoes that fit my feet and it turned out to be women’s. Haven't bought a pair of men's shoes since then. I started with 1.5 to 2.5 inch booties. Today I only wear women’s shoes. Mostly 4 inch heels everywhere including board meetings.

Well, let's just say I waited a long time - too long - to buy my first pair of heels. I was well into middle age before I dared to give it a try - even just wearing them at home. I felt guilty about wanting to try wearing high heels; I mean, what if I liked it? You mention job and social life as the things that are holding you back. But you don't need to wear them out and about if it makes you feel uncomfortable. Sure, quite a few of the guys on here do - and cut quite a dash. But it doesn't mean you have to. You can buy yourself a pair of heels tomorrow and wear them to your heart's content at home or in private or in whatever way or place works best for you. It's not a contest to see who can push the envelope the farthest. As for me I own a couple pairs of stiletto boots, but I don't wear them out and about, but instead at home while I am working. I do this in part because I am not well practiced in wearing them, in part because of where and how I live they would only get ruined, and partly because my natural style runs to knee and OTK boots with chunky heels, rather than stilettos. I bought some stilettos because they are the Ultima Thule of heels and (for guys) taboo breaking and I like wearing them, but when I am getting dressed the chunky heeled boots call out to me more often (which is why I am not well practiced in stilettos) I sm comfortable wearing feminine knee of OTK boots (with and without heels) out and about, but that's me. The point is it is not a competition. Wearing heels it doesn't need to be about towering stilettos or cutting a dash in public. It's about freedom of choice and your own personal style. The world doesn't make it easy for a guy to wear heels, but you don't have to wear them in public if you don't want to. Wear them at home. It's better to do that than never to try at all.

I found these by chance - and to my surprise they are (allegedly) available up to size USW15/UK13/Eu47, assuming that they run true to size: Link here: Women Thigh High Boots PU Leather Black Sky High Chunky Heel Over The – Prettyunik The heel height is not specified but looks at least 4". A tempting purchase, especially at the discounted price of £59.99 (with the same boots seen elsewhere at £150 or so), but I will have to pass. Little of the other footwear from this supplier ('Prettyunik', about whom I know nothing) is available in sizes above USW11 or 12.

I can stay pretty much for free wherever I like as long as I move every 14 days - and with 2000 miles of canals and the ability to work from my boat, as long as I have wifi, it is an incredibly free existence. Off grid, solar power, heat with coal in winter and cook with gas. Life is slow in the canal - about 3mph when you’re moving, but if you’re working a lot of locks in a day you travel about one mile for each hour you’re moving. The canals are all 18th century and working the locks can be hard work. And there is a lovely community among those of us who live on the canals, very bohemian, very diverse and interesting.