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Going out for the first time


zathrus69

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Guys, I'm looking for recommendations for where to go and what not to wear the first time going out in heels. I can't figure out whether it is best to go somewhere busy (so that people are less likely to be looking around but there will be more people who could spot my heels) or somewhere quiet (fewer people but when its quiet people tend to look around more - I know I do!). I would probably die if I was spotted and made fun of, I'm pretty insecure at the best of times. So I'd like to minimise the risk but where? Busy shopping centre or quiet town? Any recommendations? As for what to wear. I'd like to go out in my 4" stiletto boots but the click, click sound is a bit of a giveaway :lol: Any recommended shoe types and heel types that are harder to spot than others under jeans or combats? Thanks for any help you can provide. Cheers, Zathrus

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My first outing in woman's shoes was with a pair of Penny loafers with 2" heels, hardly attention getting or feminine in appearance. However, they did get me "over the hump" of fearing negative reaction. I gradually increased the height of my heels to where I am comfortable wearing my brown boots with 4½" blade heels (in the winter) to malls and restaurants. I do, however, still wear my trouser legs a little longer to help obscure the obvious female look of certain foot ware. I haven't worn a pair of men's shoes in several years, now. Normal shoes for everyday wear are loafer style pumps with 2½" to 3½" heels. Admittedly, I chose my shoes to match my activity. Lower, less obviously feminine, shoes for work and visiting clients. Higher heels for leisured activity. I've never worn pumps with stiletto heels in public, however. There're a little unorthodox for the conservative climate where I live.

Being mentally comfortable in your own mind is the key to wearing heels in public.

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Hello Zathrus! Best of luck to you but the answer to your questions is just common sense. Most of us worked it out for ourselves and I am sure you can: Regarding the heels, as has just been said, sdtart with lowish block heels and long trousers, and then, when the world doesn't cave in, gradually work up towards higher, slimmer heels and shorter trousers until you reach your goal. Regarding place, BUSY places every time to start with. Everyone is bustling around much too much to worry about you and your heels - you're just a tiny part of ther general scene. Nothing more self-concious-making than your footsteps echoing along an almost-deserted sreet with just two or three people standing around weith nothin to watch other than your every step. However, in busy places, avoid confrontational thugs and hooligans, and parites of giggling schoolgirls. Best of luck and ENJOY (like the rest of us!)! hgeerfully yours, Heelfan

Onwards and upwards!

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As others have said, start low and wide and raise your heels to match your confidence level. I generally agree a somewhat crowded place is better, probably avoiding malls and such where crowds of giggling teenagers hang. The first public place I ever wore heels (other than night walks on dark quiet streets) was a bookstore. They're still my favorite places for trying out new heights. Then again I'm always amazed at how few people ever notice my shoes. I'll go out wearing cowboy boots with 5 inch heels plainly showing or 4 inch platform flip flops, walk all around a crowded supermarket, and maybe catch one person checking them out -- usually nobody notices. You'll find yourself walking around saying "oh, oh, she's going to see my shoes for sure..." and alternating that with "HEY LOOK AT MY F'IN SHOES YOU BLIND IDIOT!"

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Start out with somthing like these...

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With these no body will really notice when wearing pants over them and since they are a rubber heels nobody will hear you as well. Start around the 2.5" to 3.5" heel area with out paltform added,(keep the plat small) just actual heel lift. Wear them around the house with cloths you would wear out side and over time you will get comfrotable enough to start wearing them around in public.

But don't wear somthing like these......

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A high heel that will alter your walk that will attract attention. Save the fourth picture for when you become an expert. A stiletto type heel that will be a attention getter (you could be wearing these eventually) and the last one is obvious you would not get very far. But great for the bedroom for your GF who loves you to wear heels. :lol:

Hello, :wave: my name is Hoverfly. I’m a high heel addict…. Weeeeeeeeeee!  👠1998 to 2022!

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I did my first walk in heels at 2am in the morning, sneaking out of my parents house and putting the shoes on around the corner. It was very dicey, but fortunately the streets were empty and it was reasonably safe. I do recall that I had to discover a whole new way of walking, no long strides or being able to walk through obstacles, each step had to be consciously made and throughout my walkabout I was aware of the noise they made.. a crunching solid noise which I am sure was heard by anybody who was awake. I had bought a apir of wedges with an inch plat and at least a 5inch heel so there was no real experimenting inbetween. what a rush it was... 1981, never looked back after that. Nowadays I wear mostly Mary jane styles, usually to work and around the house. heels are fun, but I am afraid South Africans are a bit too intolerent of difference.

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Guys,

I'm looking for recommendations for where to go and what not to wear the first time going out in heels. I can't figure out whether it is best to go somewhere busy (so that people are less likely to be looking around but there will be more people who could spot my heels) or somewhere quiet (fewer people but when its quiet people tend to look around more - I know I do!). I would probably die if I was spotted and made fun of, I'm pretty insecure at the best of times. So I'd like to minimise the risk but where? Busy shopping centre or quiet town? Any recommendations?

As for what to wear. I'd like to go out in my 4" stiletto boots but the click, click sound is a bit of a giveaway :lol: Any recommended shoe types and heel types that are harder to spot than others under jeans or combats?

Thanks for any help you can provide.

Cheers,

Zathrus

Hi Zathrus (and Dimpantyhose too),

I aggree with my previous speakers.

Do it whole-hearted in the bright daylight of a shopping centre! I earned almost positive experiences. I know, that showing your heels at your first outing visible for everyone requires a lot of courage. But believe me: The big majority doesn't take notice of you. In the worst case you must count with young teenie girls giggling behind you or stupid remarks of muslim immigrants or other blockhead guys. If this should really happen to you, remember always: they are narrow minded and stupid. Keep cool!

My worst experience was a midnight trip on stiletto heels at three a'clock, when I encountered (in my quarter in Frankfurt/Germany) three aggressive turkish guys. Their first loud remark "Oh, what a shit!" I couldn't help to answer "What is here shit besides you?". In spite of my bold answer I was full of fear. Me alone against three? Luckily they pissed off after a lot of typical gay-hostile insults :lol:

My recommendation for your first outdoor trip: Boots with thick blockheels as Hoverfly rcommended. IMHO style #4 is also OK. I'm wearing my 4.5'' Buffalo platform boots often in my neighbourhood (model 24400-T) and for shopping in the super market. Nobody cares for it. Worn under jeans they look like male boots. Sometimes people stare at them guessing: Does he wear male or female shoes?!

Last week I heard - waiting in the queue at the cashier - young girls whispering behind me something like "... the eighties are IN again ..." :rofl:

micha

The best fashion is your own fashion!

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Still a picture of the ankle boot version of the boots, I was talking about

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But please don't ask me, if I wear italian Parma bacon under the heels :lol: It's only a patch from an old red-brown leather jeans. The heels were simply too noisy.

micha

The best fashion is your own fashion!

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Hello Hoverfly and Micha! I think the advice you are each giving to first-time street-heeling guys is EXCELLENT and your photographs are EXCELLENT! I don't think Dimpantyhose (in his thread) and guys like him would need to be nearly so nervous if they just followed your very good commonsense advice! Cheerfully yours, Heelfan.

Onwards and upwards!

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I haven't gone out in my heels yet. The closest I came to doing so was opening the front door and taking a set out, at 3pm. I completely forgot that the kids at the school next door get out around that time so I had to get back inside quickly. Nobody saw me, unless my neighbors saw and never said anything. I might do it tonight, if I'm not busy

I wish I was a size 10

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Good luck Alex, but honestly, I can't see what the problem is if you follow the excellent advice carefully laid-out and illustrated by Hoverfly above. With lowish block heels and long trousers/pants, you can initially look INDISTINGUISHABLE from wearing normal men's shoes. hence no need for ANY fear or embarrassment whatsover. Then you take it step by step from there, realising as you go that it's fun and its no big deal to the outside world. If you follow Hoverfly's suggested programme, there is no need whatsover for furtively ducking outdoors at 3pm and straight back in again - just GO FOR IT and get struck straight in to busy shopping malls etc.! Cheerfully yours, Heelfan

Onwards and upwards!

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hi The first time you will go out in heels will be burned in your mind forever the excitment, the rush and even the fear will make you high (both ways :lol: ) all the other times after it you will want to relive this feeling but you couldn't, after a while you will even forget you are wearing HH. and HELL YES , i even miss some teens giggling. we want to wear HH freely, but HEY we don't want to go unnoticed. so make the first time special, and let yourself be seen ! go out at day to a crowded place and enjoy every moment it won't come back !!!

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Oh I don't know dawn - maybe that is too pessimisitic and even a bit of of turn-off for keen young budding streetheelers. I was only twelve years old when I went started streetheeling in my Mother's shoes. I am now just turned 59 and it still gives me a HELL of a buzz!!! In my case the excitement has never lessened - heaven forbid that it should! Cheerfully yours, Heelfan.

Onwards and upwards!

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well what i ment was that the first time i went out with heels it was :OH' DAMN I'M WEARING HIGH HEELS OUTSIDE. and now it's : I'm just wearing my shoes , which seems perfectly normal maby it's just me but nowdays i actually seek the attention. i want other to notice me and my heels while at first just knowing i'm wearing HH gave me rush of andrenaline. in some way i miss the nerves i had when someone approached me on the street, will he/she notice ? , while nowdays i don't realy care. what i'm saying to all the guys out there who are still fear the outside - don't be afraid of this moment of steping out , cherish it !!! your life won't be the same the moment youl'e walk out that door (it will change for the better . trust me)

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  • 2 weeks later...

Had a great evening out with my wife last week. We both wore tights as we often will on a night out. She wore medium heel, closed toe mules, whilst I wore regular men's slip on shoes. As the film commenced she took off her shoes and rubbed her foot against my leg which was the signal for me to slip her shoes on. This has happened a couple of times previously but this time it was at the beginning of the film and she let me wear them for the whole film. They were bought from Clarks last year for a wedding and although they're not high, they feel wonderful. Here they are:

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On the way home, she suggested that we fulfill one of my fantasies by going for a walk in heels. She had bought an old pair of her heels with her for me to wear. They are a little dated now (about 10 years old, navy blue suede, 3" heels) but they hold special memories for us as at the time she bought them they were the highest heels she had ever owned (we've put that right since!).

Here are some (poor) pictures

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The walk was only about 10 minutes long, but it was a special evening as I felt it was another step to her accepting my desire to wear high heeled ladies shoes

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Hello Smudgeur! A great posting - I'm sure that the cinema and the 10 minute walk were both a great thrill, and most importantly, you have the developing acceptance of your wife! Wonderful! You mention taking steps towards your wife accepting you wearing high heels. As a suggestion: why don't you go to Brantano or somewhere and start off by buying some ladies' masculine-toed boots or loafers with 3" or 4" block heels of the sort that a lot of us street-heeling guys use for everyday-about-town wear and that can be totally inconspicuous when worn with longish trousers. That would enable you to enjoy wearing heels for complete outings instead of a snatched 10 minutes, and would also get your wife acclimatised to your prolonged heel-wearing. Then, as each of you becomes ready, you can look forward to progessing to heels which are higher and slimmer, maybe also letting more been seen under your trouser-bottoms. That way your wife should accept your passion in gentle stages. That is the way many of us have done it, and the nice thing is that at every stage it gives you something more to look forward to! Happy Heeling! Cheefully yours, Heelfan

Onwards and upwards!

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I agree. The first time was a total blast. It was scary but I felt so good when it was done. I was in a motorway service station in 2" wedge boots (hey, it's YY, wedge boots, what else :lol: ?) Since then, lots of times, including times where I've forgotten I've got them on. I honestly think that you can get away with almost anything under trousers. I've never had any trouble, and I've done all sorts of things in heels. I even did a beer festival in 3" wedge boots and never had a comment, even from the ladies who were there. Having said that, I've stuck to either the inside of my car, or relatively crowded places so that I was safe - but then I tend to do that anyway. I've even been to crowded pubs, out all night in my heels and never had a comment (and the added height means I get served quicker, too :lol: ) Long jeans - a life-saver. I have several pairs. In fact, a couple of people want to know why all my jeans have turn-ups now. It's because I didn't buy them to wear with trainers, but I don't always feel like explaining!

Obsessed is such a strong word. I prefer to think of myself as "differently enthusiastic"

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YY, you make it sound as easy as it is. :lol:

Why thank you!

I did have a couple of near misses before I got to that point, tho'. I'd got my courage all the way up to filling the car up with petrol in a pair of 3" boots, but the petrol station was shut when i got there. At the next petrol station, I chickened out. I didn't actually do it for weeks after that!

Obsessed is such a strong word. I prefer to think of myself as "differently enthusiastic"

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Didn't you run out of petrol, then? :lol:

Emma

:lol:

Fortunately not - the next petrol station was only a couple of miles further on. Plus I had about a quarter of a tank anyway, I think. It was that I'd decided to do it then, on the spur of the moment, then lost the courage when I couldn't do it!

I've managed it since, tho', once or twice :lol:

Obsessed is such a strong word. I prefer to think of myself as "differently enthusiastic"

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Almost 15 years ago, I drove from Washington, DC to Chicago wearing a pair of brown, calf-high boots with 4½" stiletto heels. I was all alone and after a few hours I actually forgot I was wearing them. As I approached the Ohio boarder I decided to stop at one of the last refueling plazas in Pennsylvania, before entering the Ohio Turn Turnpike, and tank up and grab a sandwich at the restaurant. I pulled up to a pump, hopped out and started refueling. While the pump was running, I grabbed a couple of paper towels and the squeegee, walked to the front of the car and cleaned the windshield. After topping off the tank, I walked across the parking lot to the store to pay for the gasoline and happened to catch a glimps of myself in the window. Seeing my reflection I realized that I was still wearing my boots. Too late to turn back, I proceed into the store, payed for my gasoline, walked over to the restaurant and bought a hamburger, fries and a soft dring. After paying, I casually made my way back to the car and drove away. Reflecting back on the incident a few hours later I realized that I had walked all over the plaza in my boots and no one, as far as I could tell, even noticed that I was wearing high heels. This incident is significant because it occurred long before I ever began to regularly wear heels in public. As I remember back to this incident, I actually believe it was one of the main factors that lead me to regularly wearing heels outside.

Being mentally comfortable in your own mind is the key to wearing heels in public.

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The first time I went out was silly - 3am and 6 inch heels and a couple of beers inside. I got away with it (age 21) because no-one was around. Driving in heels is good - and then you can carry on as normal refueling / having a break etc. Three inch wedges really go unnoticed - in fact I've never had many glances at any heels so it must be time to be even more adventurous! B-booted

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YamYam you wrote "Long jeans - a life-saver. I have several pairs. In fact, a couple of people want to know why all my jeans have turn-ups now. It's because I didn't buy them to wear with trainers, but I don't always feel like explaining!" That made me laugh because somebody asked me exactly the same question not long ago. Vanessa _________________

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That made me laugh because somebody asked me exactly the same question not long ago.

Glad it's not just me then :lol:

To be honest, that's probably the most awkward question I've been asked. Most of the people I know aren't that curious, or at least haven't bothered asking me about it!

Obsessed is such a strong word. I prefer to think of myself as "differently enthusiastic"

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