Empowering Heels!

Greetings, wonderful readers! I hope you all had an incredible holiday season, and are ready for new and exciting experiences in 2020. As we step into this new year, I would like to discuss the expansive topic of High Heels.

For me personally, High Heels were one of the first feminine accessories that filled me with awe. Specifically, it was a pair of black leather knee-high boots with a 2" heel. At the time, I was used to shoes only serving their base function; utility. To see a shoe that had such an amazing visual appeal, filled me with a curiosity I didn't quite understand, and I was driven to try them on immediately.

Sliding my foot into the boot, and zipping it up to my knee filled me with such an intense euphoria. It was as if I was fulfilling my destiny, even though these desires had laid dormant in me for the first years of my life. All I knew was how much I enjoyed putting them on, wearing them, and seeing them on my feet/legs. The feeling of a heel underneath my foot was incredibly new at the time, but it filled me with confidence as I became taller, and my posture was straightened.

High Heels have been a symbol of femininity for so long, that the majority of the population doesn't realize that they were originally invented for men. At their genesis, they were invented for horseback riding, as the heel helped keep the riders foot secured in the stirrups. Not long after, they became an item worn by Nobles, as to convey their status. Women then took notice, appreciating their fashion appeal.

If you've read my blog on Hosiery, you'll notice a similar trend of such items being invented for men, women taking a liking to them, and men abandoning them for fear of being considered "less manly". One of my main goals in dressing femininely, as well as writing these blogs, is to break these stigmas. Sure, wearing makeup, heels and skirts make one appear feminine. However, both femininity and masculinity are not limited to clothing.

Bravery is a traditionally masculine trait, and what is braver than overcoming your own fears and wearing something that is so stigmatized? High heels are perhaps the boldest feminine accessory out there, and I wear them with confidence every day. I hope I can inspire you all to do the same, as the only way to break toxic stigmas is by normalizing things once considered taboo.

When I first began my journey, I purchased two pairs of heels. The first was a pair of satin thigh-highs with a 3" chunky heel. I've always adored the alluring sheen of satin, and I loved the look of such a material gracing my whole leg. The second pair were studded open-toed heels with two straps to hold them on. These had a very thin 4" heel, which was incredibly difficult to walk in. However, the difficulty is worth it to be able to wear such amazing shoes.

My feet are naturally arched, so I became accustomed to wearing heels relatively fast. At first, though, I would only wear them at home because I did not want to make a fool of myself publicly by stumbling around with horrible form. My mistake was going from wearing flat shoes for the first two decades of my life, to 4" heels. My advice: start slow. Get a 2" heel and upgrade when you feel comfortable in doing so. Walking in heels definitely takes practice and patience.

I have found that routinely exercising your legs is one of the best ways to make walking in heels easier, as it requires a decent amount of muscle in your calves to walk on the balls of your feet constantly. Walking in heels itself is an exercise, and if you are out of shape it will be much harder. I have been wearing heels daily for months, and I can confidently say it gets much easier with time. In fact, I find it more uncomfortable to wear flat shoes, and I often wear a 2" heeled leather bootie when I need to do a lot of walking.

Once you start wearing heels, so many more options will open up for your shoe collection, and you will never want to go back to the drab male options. XD has a decent amount of heels made specifically for men's naturally wider feet, my favorite being the "Silver Open Toe Pumps". In fact, XD is the best place you can buy heels as a male because they are suited to fit our feet perfectly. I've had to return plenty of shoes purchased online from other sites, as they were always too narrow for my feet. High Heels that don't fit correctly will make walking in them an absolute nightmare, so shop wisely.  

High Heels are my favorite feminine accessories, simply because they not only look and feel fabulous to wear but complete literally any outfit. And thus, my blog on High Heels comes to an end. What are your favorite types of heels? How high do you like the heel? What are your favorite styles? Let's get a great conversation going!



I finally got the courage to tell my wife yesterday that I want to wear her dresses. She’s already bought me panties to wear, I was hopeful she wouldn’t freak out. She didn’t! I am wearing one of her dresses now with some green bikini panties that are so soft. I’ll need to ease into the bra situation, but so far so good. Sometimes she catches me in panties and paddles my bottom. She makes my bottom hurt. I’m glad she puts up with my fantasies and uniquenesses. Her clothes are small size, we need to shop-hopefully today, for some dresses in my size.

Michael June 08, 2020

Hi Nathan,

i would like to add a side note on your comments concerning clothing history.

You are correct about men wearing heels first, but men also wore wigs, hosiery, skirts (in some cultures), etc. These were usually all started by the nobility (or common sense), and when the middle class came into existence they copied the trends of the nobility.

Where you faltered was when you stated that once women started wearing the clothing, men started questioning their masculinity and ran from the options. Actually, it was the industrial revolution that made it impractical for the working man to continue wearing such fashions in a place that was filled with deathtraps for wigs, heels, skirts, and anything that was not worn near the body. When the Industrial Revolution was in swing, it was the Victorian Era that “standardized” what men and women should wear. We have been in the corset of the VE ever since. Once a garment became “feminine” only, men couldn’t wear it. The reverse was true.

When the feminist movement began and women began wearing men’s clothes again, men did not loosen their own stringent choices of clothing (except in the counter-culture). And this leads us to now, where men are hopefully reclaiming the right to wear clothing that traditionally began as men’s clothing. However, only women’s versions of some articles tend to be the only versions available for men to wear.

Viva la revolucion!

Histrionics May 12, 2020

I deliberated for months about getting a pair of heels. Main stumbling points were , what kind , do i really want them etc, will i be able to walk in any pair etc…..

Eventually bit the bullet and went into a store here and ordered a pair. Completely ignoring all Youtube advise of get a small heeled pair to learn with etc….having bought a black leather pair of stilettos that were 5inch extra thin heeled. Dive into the deep end i figured

They took three weeks to come in to stock and then i went in and tried one on. Just one.. to ensure they fitted. Paid for them and took them home.
Couldn’t put them on that day as others were around the house etc…

But when the house was empty i grabbed the box , got them out… put on one of my pairs of fishnets and then put the stilettos .

They were like putting on electricity.

The feeling of kink and excitement all at once was game changing.

Tough to stand in at first… and impossible to walk in as well.

But with a few hours of practice i now have it worked out. Also have new appreciation for those who walk in high heels every day.

Love them and have ordered two more pairs…..

Phil March 16, 2020

women are way ahead in freedom/choices..i love wearing heel and stockings.they ,more than any thing else makes me feel sexy/womanly,esp during sex…mmmmm

johnnie February 20, 2020

I hear you nathan but I have a family and a job that says not so fast. I d lise everyone and everything, not ready to do that. Bit I encourage those who can

Stevie February 09, 2020

Stevie, you can wear them no matter where you live! I live in Idaho, and I’m the only man to wear heels publically that I’ve noticed. You all need to get on the bandwagon!


Nathan February 09, 2020

Nathan where do u live? I cant here in NC . But I m glad you can !

Stevie February 04, 2020

Hey everyone! I’ve loved reading all your comments, and it’s great to see we all share the same affinity for heels. I agree with you all here, high heels are the absolute epitome of femininity. An outfit just isn’t complete without them. That is why I wear 4-5" heels daily, as my default choice. Break the stigma and get out in public and wear some beautiful heels!


Nathan February 04, 2020

Great to be wearing my lovely satin tanga today. My absolute favourite. So light it feels barely there. Not a day for heels today though. Shame.

Stay pretty.
Ally x

Ally January 30, 2020

Een hak hoort erbij. Althans zeker als je ook meer wilt dragen dan een slipje.
Prachtig om te zien :-D

A heel completes it. Certainly if you also want to wear more than a pair of panties.
Beautiful to see :-D

Chris January 27, 2020

Hi Gurls – we all know that high heels have to be up there with the most iconic and desirable of feminine apparrel. Every gurl has had a pair in their dressing journey, which they have either mastered – or been turned into an uncomfortable, precariously wobbling jelly. For me, comfort in shoes is so important. If I can’t walk well in them, I don’t bother.

I’m lucky in that my feet fit the upper and wider end of women’s sizes and so I have a fantastic range to choose from. Whilst six inch highs with ankle straps are the stuff of fantasy, I find two to three inch heels in a more blocky style much more comfortable. My latest pair are actually one inch sling-back kitten heels in snakeskin. What’s not to love when paired with wetlook skinnies. Love the trend for leopard-skin prints right now too. There’s so much out there.

Stay pretty

X Ally.

Ally January 26, 2020

Oooo I love me a pair of heels! 4 or 5-in classic pumps are my favorite part of any outfit. They just complete the look and I love how it feels to slip them on. Can never have too many!

Skyler January 26, 2020

Great topic. I have been wearing heels for years and it has to be my favorite accessory. Like the others on this topic, I started out wearing my mother’s with her approval and her help in choosing the right style and height. It does take practice. I started with 2 inch heels and gradually worked up to 4 inch heels. Today I am wearing a beige 4 inch pair around the house.

Randy January 25, 2020

Ooohh high heels are soooo sexy on either men or women! Thanks for the blog Nathan, I can’t think of a better subject to start the weekend! I’ve been wearing heels off and on for several years now and it’s hard to accurately describe how wonderful they make me feel except to echo some of the above comments. There’s no other accessory I can think of that brings out my femme side like heels do. I started out “low and slow” with 2-3” heels and finally worked up to 4” heels, but it takes a lot of practice. My GF helped a lot, both with advice on walking and with shoe selection. Once I got used to it I became more confident when wearing them and now it’s almost second nature.
Unfortunately, I haven’t worn them yet to work (though I ldo wear light makeup and have never heard an unkind word) but someday I’ll soon I hope we can all go to work in our heels and no one will consider it unusual. For now, it’s weekends out and evenings around the apartment. It’s hard to put into words how fabulous they make me feel. I’m more confident now that I’ve had some experience with them and my GF and I love wearing them when we go out together, either alone or with others.

So get your femme on gurlz and strut your stuff this weekend!!


Kyrstin January 25, 2020

Hi Nathan. Great blog! The first feminine apparel I ever wore was my mom’s navy blue high heels. She also had a pair of loafers I loved, and she was fine with me wearing them. Little did I know that from this interest in mom’s shoes, I would end up with an entire wardrobe someday. Due to foot problems (arthritis) my high heel days are over, but I have a nice selection of sandals, ballet slippers, loafers, and even a pair of over-the-calf boots.

Thanks for your research on the history of high heels. You are absolutely right that high heels were the thing to wear when riding a horse and, incidentally they still are – only now we call them cowboy boots and they have a semi-high heel for the same reason, and oddly enough, they are considered macho. In the regency period of England, men wore high heels, but they soon became viewed as the costume of dandies (members of the aristocracy that were considered a bit odd.) Anyway, thanks for this stimulating topic. Well done!

Fond regards,

Angie January 24, 2020

Love love a great pair of 4 inch heel started with black oPatten then a great pair of boots.Boots are the sexyies shoes a man can wear

sidney or cindy58 January 23, 2020

Great topic
My crossdressing started with heels. My mom wore a lot of heels and i always check out the bright toenail polish with the sling back open toe pumps she wore as well as the open toe sandals with the skinny heels
Once i tried them on i was hooked. I added the nail polish stockings panties bra dress in that order

For me heels complete the outfit. It signifies openly that there is something feminine happening here. You can wear lingerie (panties bra stockings) wimens jeans tops but add heels to anything and it feminizes the attire.

Now I love the peep toe pumps platform pumps and strappy sandals with pretty nail polish. Oh how I wish men could wear without stigmatism. Now of course for special occasions I d like to don a dress. But a stilletto and skinny jeans and turtle neck with a matching bra panty would be AWESOME

SO yes I love heels wish they were mainstream!
Wear something pretty today i am
(Black high leg panties from jockey-had to go stealth today because i was in a locker room )


Stevie January 23, 2020

One of my many comments on heels. The beautiful melody of a stiletto strut.To hear your heels clicking beneath your feet,EXQUISITE!!!!!!

Sallee January 23, 2020

Nice, very nice, almost my favorite subject. My favorites are 4" pumps, with a thin heel and not necessarily black in color.

These are almost magical and I hate the fact we men don’t have shoes like these. Everything in this world is for women, or at least that’s how it seems to be.

Ivo January 23, 2020

I really prefer almond toes heels

Rudy January 23, 2020

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