Outing in high heels, in male cloths or passing as a woman

[kobo]

I plan to go out in my high heels and as I’m not enough self-confident to stand any curious glances or comments I got two options First is to do it in more or less male cloths with my female shoes hidden by wide legged jeans, this is what I did, and what turned out to be slight disaster. I went out in stilettos with their fabulous click, click, click….You can imagine what was next. I supposed it to be just nice stroll and cup of coffee in coffee shop but I underestimated these click…click…click, later I felt terrible, Anyway, now I know I should have wore more wedge heels, but telling the truth I did not have such then and I don’t have now either. Second way is to go out in my favorite stilettos but dressed more woman style, I mean make up, painted nails, proper hair and glasses and some loose unisex looking plain cloths. I do it often at home. Actually I dress this way; besides make up and hair; almost every day when I’m working alone at home. Due to my physique I can quite easily pass as a female as I did it before at fancy dress parties, but it was not what I’m going to do now, to go out dressed as a woman in stunning pointed stilettos. One disadvantage is that I wont say a word, I wont even try, so there are limited places where I can go. All this isn’t easy for me, but I just cant stand wearing heels, painting nails, wearing all these gorgeous cloths and staying home all the time, working at front of my computer. I guess it’s the only way and sorry for my terrible english, I know..

[Ionic]

First your English is very clear and well constructed, you certainly don't need to apologise for it. Much better than my feeble efforts in French and Italian. [edited: and even rustier Spanish!] Secondly, please do tell us which country you are in because that will help us understand the cultural background your questions are coming from. Why not add it to your hhplace forum profile. You don't need to add any more identifying detail. (everyone else please note too!!) Here in London, I believe you would get more stares passing as a female than wearing 3.5" block heeled boots, or even slightly tapered ones, with reasonable length boot cut style trousers. If you do want to pass, you need to be able to do it very well. It is not for me, the full beard is rather a 'give-away'... /I

[kobo]

I live in Spain although I'm not Spaniard. Yes I want to pass and I hope to do it well, I want to try at least Anyway thanks

[chris100575]

Good luck, I hope all goes well. Personally I have no interest in passing as a woman, probably due in part to the fact that I wouldn't stand a chance! All the best for your outing, let us know how it went!

[Firefox]

I've never worn heels in Spain, but have done so in France, Belgium, Netherlands, Moscow etc with no problem. I don't believe it would be any different in Spain as it seems a relaxed type of country from what I hear. I think you'd be best off wearng some 3 or 4 inch quiet blocks with jeans and normal attire, about 2 inch of the heel showing. Unless you have an interest in X-dressing or whatever why do it? I X-dressed a few times at University in my late teens as I thought it was the only way to wear heels, but I didn't enjoy it. I thought, why the fuck am I doing this when all I want to do is wear heels. So once I realise it is perfectly OK to wear heels in male mode I never looked back. So if you can, forget the X-dressing and develop your own style. But it seems from your first post that you like to X-dress as you mention gorgeous clothes and such like, so you might need to take some advice or read some TV sites on how to do all that properly.

[Ionic]

Do both!! You clearly want to pass off, but when you don't have the time to dress convincingly, get the ankle boot out as Firefox described above, and go male mode! /I

[new_look]

ive tried x dress very briefly and failed miserably, probably because like firefox i didnt enjoy it and it was a simple cover up for the heels. I prefer male mode and can say i enjoy it more than tryig to appear as a woman, even though i can probably walk as good as if not better than some women in heels

[chris100575]

I know for a fact that I can walk as well in heels as most women, and better than some. I still look like a big hairy guy in the process though! Even without the beard and tattoos, the only way I'd pass is if I claimed to be an East German shot putter.

[WarrenB]

I know for a fact that I can walk as well in heels as most women, and better than some. I still look like a big hairy guy in the process though! Even without the beard and tattoos, the only way I'd pass is if I claimed to be an East German shot putter.

HaHa! I don't even want to think about that...

[Thighbootguy]

I go out in thigh boots with 4” stiletto heels as a guy. I tried X-dressing a couple of times but I don’t do it well enough and haven’t a chance of passing. Like Firefox I thought that was the only way I was going to be able to wear the boots I like. After finding this forum, it dawned on me I could wear whatever I wanted and I’ve been having a great time ever since. X-dressing can be a lot of fun. I wish I could pull it off but wearing thigh boots as a guy is also a hoot. The key is to enjoy yourself. I like Iconic’s advice, “do both”. Have a great time.

[kobo]

Yes in some way I enjoy x-dressing, although I’m not so sure what is most important for me and what I really need. My interests develop. Few years ago these were simply womans shoes, any style at first, later more and more feminine. As time was passing by I started to shave my legs, wear tights, makeup and paint nails and so on. I was discovering more and more new female clothes for me. Now I wear all outfit; makeup, bra (though I don’t have breast forms, shame:), jewelry and all womans cloths, frilly and shiny, (sometimes plain, but same womans), but not every day of course, just from time to time, once, twice a mounth. I do it with pleasure though it is a kind of a play for me, in order to have fun, to feel what woman feel, you know, wearing all these things I know or feel they are not my every day cloths and I don’t want them to be I guess (though I’m not so sure about that , ok let’s say I’m quite sure) But at some points I’m not so undecided and I can call my every day dress style. I definitely just love stilettos and other female shoes, I wear them almost all the time when at home, driving car sometimes. And I rarely plunge into my stilettos with bare foot, first I slide into nylons, (gorgeous feeling , yeah stockings, tights are indispensable. And also I paint nails, transparent slightly shiny sometime even when I go out, all shades of feminine colors when at home and not expect anybody’s visit. I have my nails painted almost all the time. I don’t take into account female underwear (I wore my ex-gf’s panties and she knew it and enjoyed it, now I do just the same) Bout cloths, apart from skirts I wear sometimes, I take unisex style, same or similar as I wear outside. So when I work at home freestyle dressed, sometimes its enough to change shoes and I can go out, (providing, passing as male nail polish color, proper cut of legs when in stockings, no lipstick Now I desperately want to go out dressed my everyday style, but maybe its just excuse and really what I want is whole x-dressing. I feel I must do it so to know my inner reasons. Anyway thanks for all your words, I just needed them.

[Firefox]

I suppose it really depends who you want to meet and what you want to do also Kobo.If you want to appear as a woman then you are going to get guys interested in you or a few women who like X-dressers. You might have to learn a female voice or female mannerisms an stuff like that. If you want to wear more wideranging things then you may be a freestyler, or if you just want to do heels or nails then you are just pushing fashion boundaries as a man. I've found the last one is acceptable in work and all social circles. You'll have to decide exactly where your interests lie and as Ionic says, you could do both, but you'll need to be careful what social fabrics you integrate any particular fact of yourself in that case.

[kobo]

So I did it, I did it today, yeah I did it and it was just fucking great!!. I said to myself now or never and I did it. Even now I feel some sort of thrill when I recall it. I was so excited, but all went just smooth. I was just walking in my fabulous pointed stilettos, I bought for over 200 €, unveiled this time, outrageously clicking and I was just passer by, no glances, nothing has happened, nothing at all, just nothing, I could do whatever I wanted. All my fears have gone. Finally I sat at the table in a street café and bought a glass of water, yeah I said just two words, almost whispering, but nobody even looked at me, waitress neither. I felt as in a dream. Recalling my first going out in stilettos, after which I felt as raped or something like this in mood, I just couldn’t believe. Walking in stilettos on the street, pavement, I mean in real life is quite different story then at home, its slightly tiring and its better to avoid rough surfaces, although for the first time, coming home I put my stilettos off, not put on like almost every day so far. The most I was afraid of were my face and hair; though my make up was almost a piece of art I wore glasses and a plain scarf on my head, so looking at my face there were lips only, it was just impossible to discover anything, I guess so. Then slightly big shoe size as for a woman, 43, but these are real woman’s style shoes, stilettos ultra pointed, maybe a bit exaggerated even. No doubt they are big, however its hard to judge by this kind of shoes. And of course fact that I’m about 1,80m when high heeled, pretty tall (these heels are 10cm high only, shame I know, just casual shoes) But it worked, I was so uptight but it fucking worked. Simply tall young woman in stilettos, no stares, nothing unless some natural looks at me, at my foot, but these looks were sort of swift and ordinary looks, just as mine as I see a girl in stilettos, something like that. Catching these looks I even felt a sort of excitement, its completely wired I know, but I liked it and I must do it again. Unless reaching my home, when I turned the key, I felt save and some sort of relieve, yeah I must get more self-confident, no more stress. What I was afraid of was driving home; it takes almost one hour each way. I had my male cloths in my car just in case. I could easily slip out of stockings and spikes, but make up and especially red nails would be a problem so I took a pair of sport gloves and cosmetic towels. Happily I didn’t need them. Now I feel so so so fucking free, there are no frontiers, I can do whatever I want. I can wear whatever I want. Sorry, I’m boring but I had to tell it somebody.

[Heelfan]

A really great report kobo! Very vividly and sincerely written. Congratulations on making the outing, and congratulations on writing about it. Thank you! Cheerfully yours, Heelfan

[Firefox]

No problem, Kobo. The most important thing is that you first find peace with your own inner feelings whatever they are. Then you can fit that into your life in some way, but never deny to yourself what truly want form your outwar persona. Make your fantasy reality in as most practical way you can. That's what you are doing now. That's what I did too and I never regreted it.

[Thighbootguy]

Great outing kobo. The idea that I could wear what I wanted came as a real revelation to me and it sounds like it hit you the same way. Confidence comes with practice but never abandon caution. There are still people that feel it’s their job to make the world conform to their standards. Thanks for including us in your adventure. Thighbootguy

[kobo]

Thanks guys. You helped me so much. Some time ago it seemed to me unfeasible. Now I'm not like a bird in a cage anymore.

[TallSwede]

Kobo, I know that I am very late with my response and I am sorry for that. As already have been said, YOU have to decide what feels right and NOBODY else. It is your life and noone else can advise/tell YOU what is the best way to go. You have gotten some very good advice here, but in the end, YOU are the only one to decide how to proceed. I am a "lucky"one as I (really) have a spinal disorder as an "excuse" (I more often verbally disintergrate the eventual commentors (real fun actually)) I myself am happy with wearing HH's whenever I need/want and also nail polish at times when I want to look nicer... As a matter of fact, I am trying to save money to be able to get myself a set of about half inch long finger nails for the christmas (and longer) holidays if I am able to afford them (it's about EU60 and the broken car engine costs about EU500, which also by itself is sobering enough...), anyhow just follow your deepest feelings (unless they lead to prison...) and try to find your own way before the grave. -Cynical mode on: -Life is a series of hard hits, then you end up in a deep hole in the ground; -Just like golf ball... /Cynical mode off... TallSwede

[kobo]

I’ve come home at 7 in the morning after whole night in stilettos. My foot are dying. For the first time, putting my spikes off I didn’t feel slight bit of excitement as usually, but just great great relief. They have almost killed me. I’m wondering how women; they are incredible; can spend whole life wearing this stuff.

[Heelfan]

Simple - before plunging in to a marathon session, build-up slowly, conditioning your feet by short sessions and then slightly longer and longer ones. The flesh of the sole toughens, and the circulation adapts to coping better with the high-heeled foot. Believe me, women (even the staunchest of them) will suffer JUST as much if they are out-of-condition at the time of plunging into similar marathon heel-wearing (like long weddings etc.). However, on the whole they have more common sense and take it a bit more calmly and gradually than us guys, probably because most of them wear heels mainly for fashion etc. and are not fanatical enough to rush into wearing overly high heels for hours on end to achieve any sexual arousal. Although one or two lady posters on this forum (and particularly on Jenny's Forum) might be rare exceptions to this! Cheerfully yours, Heelfan

[TallSwede]

-As Hellfan already told you, You must find out your current "all day heel height" and accept that for the time being. Then you might train yourself to wear higher heels for extended periods until you eventually find that you have reaced your limit due to physical reasons or whatever. Best of luck, TallSwede

[FGWJON]

dressing as a woman just to wear heels in public does not really appeal to me either,those of who have met me would probably agree that if i was in drag i would make a passable Bella Emberg crossed with Anne Widdicombe!!!!!!! Hello to all again back with you in civilization after a three week stint in Pewsey!

[Firefox]

You do yourself an injustice there John! Anyway, it's always seemed to me that wearing something like heels as a guy is completely different activity to cross dressing. Most people do neither, some do both, and some do one or the other, but the exclusive male mode heel wearers are certainly quite a small group.

[Heelfan]

Well, granted you're the expert Firefox, but don't you think you're underestimating the total number of 'Male mode' guys in heels? A number of Forum members have posted that the USED to cross-dress, but then realised in was mainly only to 'carry off' the heel-wearing, and have subsquently abandonned the other stuff just to concentrate on enjoying continued heel-wearing in male mode. Also there are many Forum members who choose not (or are unable) to come to our Heel-Meets. Then there's the lurkers who are out there looking in without participating. In fact, we regularly meet two or three of them at the Heel-Meets, so goodness knows how many more there are out there! Then there must be people like I was until recently - never having known these Forums existed, but nevertheless happily street-heeling away in 'male mode' (I've never been interested in anything except the shoes) for years and years. Then there are the large numbers of guys who turn up in heels to the Rocky Horror Shows. Some of them are jokingly borrowing some heels for a one-off laugh on the night, but others are obviously 'old hands' turning up in their well-worn regular high heels without necessarily being forum members. If there were a way of conducting a survey (which of course, would be impossible), I think we could all be surprised by the number of male-mode street-heeling guys. Come to think of it, Richie might have some idea, because until earlier this year, he had been running some sort of questionnaire on his "Heels4Men" site. The Tidings of The Season to all male-mode street-heeling guys! Cheerfully yours, Heelfan

[Firefox]

I still don't think there's that many of us in the world. If you consider that this site is very well linked and rates well on search engines like Google, it wouldn't be long before a male mode street heeler came across us and, seeing as we are one the only sites where these kind of people post, he would be pleased to make contact. If you care to compare the numbers we have as against the many hundreds of thousands, if not millions of TV/CD type sites one can't but help come to the conclusion that there is a large difference in the sizes of the groups.

[PJ]

I still don't think there's that many of us in the world...

kind of feeling like the minority within a minority, huh?

[Robert]

Come to think of it, Richie might have some idea, because until earlier this year, he had been running some sort of questionnaire on his "Heels4Men" site.

What happened to Richie's website? When are his remaining pages finalised as he stated on his website?

Robert

[Firefox]

I don't know. He did have a busy job and a girlfriend and it's quite possible to integrate your unusual shoe preferences into everyday life.

[kobo]

I became complete x-dresser. Yeah this is what I really needed. And now Im more and more confident. I guess I felt that shoes are not enough. Now I develop more and more my second, female image, and I really feel good with it. Im just myself.