Your first time out wearing heels

[misterd73]

I thank this community's members for being so opened and posting their experiences. It has been very edifying for me and I'm gaining confidence to "go out" for the first time with my stiletto boots. I'd be very pleased if you could share with me (with us...) your first time out, as well as any advise, as I feel that the moment is "close" for me. Thanks in advance.

[morpho]

Welcome, thanks for joining, is great to share all experiences and yes indeed it is a very helpful forum, because we can get answers to all of our existential questions and doubts, at least to me it made feel free and without a guilt, I started to enjoy the experiences much more after reading all this forum in a regular basis. First time out, is maybe the most important and most dificult to do. In my case I just did it and it was very dificult, althought i had short trips out in public but no public, i never consider those ones as a real outing, since the challenge is to face the crowd and the eyes of others, and at the same time feel that you are showing off the shoes and the outfit in a full view. My "first first outing" was in Austin Texas, at down town after partying i went back to my former home in 2005, change, i was very drunk though, then I went to the streets, i was totally in femme with a blonde wig and pink suit, with a nude shiny hose and a pair of black 5inch pointy pumps. it was awesome but nobody saw me even if i were walking 2 or 3 blocks twice, then i went back to my car and drive back home, by then i was not that drunk, i have to say that it was stupid, because if i were driving drunk and in femme can you imagine what it could turn out all this story if a cop busted me? imagine walking straigh line in heels and showing the cop my nude legs and heels, in the first outing.....it was really risky. Then another trip to the public but again no public, it was in a park in NYC last year, it was very cold and at night, i wear sporty outwear to get out from my home and then went all the way to the park, once there I took of my sweat pants and sweat shirt, under them i was wearing a brown pencil skirt and a black blouse, i put on a women black coat and took my back pack inside a woman's purse, which was containing my 4.5 inch black leather boots and a wig. ALl the change i did it in less than 2 minutes over a bench in that park, amazing uh? then i went back and forth with my outfit until i got sored under my feet, it was only one couple that saw me, they passed in front of me in the same pad and i look straight to the eye of the woman, i could felt that she was scared at me, my silhuete was not fememinine at all and she could realize from far that i were a man in femme, the guy was totally frozen and never try to look at me, but that woman was staring and giving me a look of being scared big time. I realize that it is not safe to heel in public places that are lonely, just becasue as well as one cannot feel safe maybe the others neither, you never know what can happen. Then my first real outing was last halloween, please check my thread in tv and cd, a"a woman's halloween outfit". what can I tell you besides what i wrote is that hopping into a halloween party totally in femme with even your nails done, was an experience, and the whole long long night worthed the try, I didnt got any negative in fact some ladies were atracted to me, and something in them makes them know who is straight and who is not, but there were also bisexual folks that were looking after me as well but without any indescent experience, in fact we went friends and toasted loudly afterwards, I can tell you that feeling the tighs and the high heel all the time, sitted, standed, walking, talking, paying or even at the taxi, make an experience, and what it make the excitement is that there are people watching wondering and maybe admiring, ....something else that grab my atention is that at the first moment I felt very shy and very self conscious that men were looking at me, in a way that they were totally fixing their eyes beteen my legs and at all my legs and shoes, that was awkward and nervous, later i started to distinguish men that were atracted to another man wearing in femme, men being surprised at seeing a man wearing a halloween custom in femme no big deal"cheers happy halloween!!", and men that were wondering if one day they can have an opportunity to experience that, by checking out deeply and maybe making some comments to their partner or friend next to them. I realize the women fixes the eyes to the clothes but not to who is wearing it, but men always fixes the eyes to who is wearing it and always if it is a man in femme, always always look down to see the heels and the hose, like if they are also doing it closed doors, which sometimes i think that the statistics may be higher than what we think, out of 10 guys 1.5 or more is or has an intention to be a heeler. My intinct is that maybe a 25% of men has no problem to be a heeler but society plays a big role, and there could be men that are so weak to accept, but will always be admirers, and never accpet to themselves, that would be sad if is im not mistaken. I realize that my second experience will be very difficult as well becasue it wont be on halloween and it will be in a normal day or night, at the shops, well thats the idea. So maybe my second time will be the real real first time. but for sure my conclusion is that everytime is a first time since all are diferent. and what we get out from those experience is a better SELF CONFIDENCE everytime, for life, for businesss, for love, for family for us. cheers, hope you can make it soon, take some pics.

[Guest]

Bonjour Misterd Sorry I have to stay in English as my French is almost none existent even if I got the grammar right. some simple advise Darkness is a godsend and hell shadows to hide the heels but it hides the surface that you are trying to walk on. You may wish to be away from your own town just in case you are recognised get to know the streets were you go. get used to the sound of the heels so you are relaxed at what you hear. Be confident, will you go en femme or masculine each has hazards? but unless verbally challenged, walk on don't panic and don't run. So many have said it "it's in your head" a "Head game" Not being relaxed is 90% of the problem. When you are ready just enjoy. I like the Bretons and Carantec in the bay of Morlaix I found very beautiful. I want to return back there again but not via Saint-Martin-des-Besaces had a nasty accident there. Al

[misterd73]

Alsheels and Morpho, thank you for your answeres, thank you for sharing!

In my case I just did it and it was very dificult, althought i had short trips out in public but no public, i never consider those ones as a real outing, since the challenge is to face the crowd and the eyes of others, and at the same time feel that you are showing off the shoes and the outfit in a full view.

I think that if I succeed going out "in public but with no public", it's already a great victory!

Then, going out in public will come. I agree with you, that's the real challenge - especially for me, as I live in the countryside. Minds are much more closed here than in big cities.

Yes, reading these forums daily has been source of motivation and release from social conditioning.

With everyday that passes, I feel the urge to liberate this "feminine" side of myself, starting with the heels.

Like yourself Morpho, I find a curious attraction to a men in femme. I'd love one day to feel what you felt when other men and women were looking at you, some feeling attracted. It must be a great feeling!

please check my thread in tv and cd, a"a woman's halloween outfit".

Oh I will! It's something that I have never reaaly explored but feel real curious about it! It's something that I need to try one of these days too.

my conclusion is that everytime is a first time since all are diferent. and what we get out from those experience is a better SELF CONFIDENCE everytime, for life, for businesss, for love, for family for us.

I fully agree with you Morpho. I have already begin to feel that.

Besides, wearing heels or even "go further" into the experience like you guys who do TV/CD, means caring and taking care of ourselves. This can only be good, as often we have a tendency to care for others or for our jobs, often neglecting ourselves.

I will surely take pics, even if very discreetely with my cell phone...

Sorry I have to stay in English as my French is almost none existent even if I got the grammar right.

Alsheels, by all means; thank you very much for even bothering to reply. Don't worry about your French. I can speak English. Thank you for your poleteness though...

Darkness is a godsend and hell shadows to hide the heels but it hides the surface that you are trying to walk on.

Yes, it would be better to do this at night. Yet, I have to pick up my kids at school and the wife and kids are home at night. It'll happen sometime in the morning. I really have "no chocie" and I want to do it...

You may wish to be away from your own town just in case you are recognised get to know the streets were you go.

Excellent advise. I was thinking on going to a place about 10 km from home, with a big concrete surface that extends along a beach (which shoud be deserted during the morning, as it's winter here...). I might have to reconsider the location.

get used to the sound of the heels so you are relaxed at what you hear.

I just love the sound of heels.

I can't wait to hear the sound produced from my own when walking outside.

Be confident, will you go en femme or masculine each has hazards? but unless verbally challenged, walk on don't panic and don't run.

I think I will go masculine. In fact I have no experience in TV/CD. I must look deeper into that, as a complement of my "heel" experiences.

I'll think I'll just wear this: http://img299.imageshack.us/my.php?image=bottes5dm7.jpg with a simple coat... what do you guys think?

I'll try not to panic and not to run... good advice there!

I think I need to find someone with good experience on CD/TV to explore that side.

So many have said it "it's in your head" a "Head game" Not being relaxed is 90% of the problem.

I fully agree with you, 100%.

I like the Bretons and Carantec in the bay of Morlaix I found very beautiful. I want to return back there again but not via Saint-Martin-des-Besaces had a nasty accident there.

Thanks again for the compliment! yes this is a very lovely region and here's where I live: http://maps.google.fr/maps?hl=fr&tab=wl, which is not far from Carantec.

Ah, you were coming from CAEN on the A84, I reckon?!? Yes, dangerous road.

I'm looking forward to deepen our friendship and perhaps meet when you return to Brittany.

Thanks again, guys, for sharing your experiences.

[Dawn HH]

Sounds like a great first time outfit to me. Try it and go out in daylight and see how it feels. Look in a mirror first before you go. If you think your outfit looks O.K. to you, then go out and do some streetheeling and have some fun. Once you try it, you will not believe the fun you will have and you will want to do it again soon after and that is how to build your confidence to do it again and again. Then post here to let us all know of your progress. Cheers--- Dawn HH

[johnieheel]

I thought the world would come to an end. I thought I would get beat up, laughed at, poked fun at, earth quakes would happen, every building I went in would fall in and the list goes on and on. Nothing happened and it was great! Never looked back.

[Bubba136]

I thought the world would come to an end. I thought I would get beat up, laughed at, poked fun at, earth quakes would happen, every building I went in would fall in and the list goes on and on.

Nothing happened and it was great! Never looked back.

Geeze, Johnieheel, some people feel the same way when they walk into a church?

[johnieheel]

Matter of fact... Same answer if that were the question. Not to get off topic but thats how I was raised. I knew I was going to hell cause I could never do anything right so the first time I walked into a church I thought God was going to condemn me straight to heel and I was really scared! No Kidding!

[bladerunner]

hi misterd73 well five years ago i wouldnt have even opened the front door in heels,as yet i havent done stilletos but do go out in wedge heels and chunky heels mainly 3 or 4 inches,because as of yesterdays example! my legs ached like hell from 4hours of walking up and down oxfoed st! great fun but boy talk about needing some practice. My advice is start simple if your not confident..comfortable styles and build from there..it is very different from heeling indoors to heeling outdoors,especially going up or down a hill as wimbledon where i live is full of them!! BUT do it..its great fun and very liberating ,you only live the once so go out and enjoy!! A tip ! pick a nice neighbourhood around dusk for starters!!

[misterd73]

Sounds like a great first time outfit to me. Try it and go out in daylight and see how it feels. Look in a mirror first before you go. If you think your outfit looks O.K. to you, then go out and do some streetheeling and have some fun. Once you try it, you will not believe the fun you will have and you will want to do it again soon after and that is how to build your confidence to do it again and again. Then post here to let us all know of your progress.

Cheers---

Dawn HH

Sounds like great advice and I am already drooling about the perspective, as it may happen tomorrow if I'm off and if it's not "raining cats and dogs".

Thank you very much Dawn!

[misterd73]

I thought the world would come to an end. I thought I would get beat up, laughed at, poked fun at, earth quakes would happen, every building I went in would fall in and the list goes on and on.

Nothing happened and it was great! Never looked back.

Yeah, I aprehend the reaction of others too. Yet I'm looking very forward to this experience.

Thanks for sharing your ideas, Johnie!

[misterd73]

hi misterd73

well five years ago i wouldnt have even opened the front door in heels,as yet i havent done stilletos but do go out in wedge heels and chunky heels mainly 3 or 4 inches,because as of yesterdays example! my legs ached like hell from 4hours of walking up and down oxfoed st! great fun but boy talk about needing some practice.

My advice is start simple if your not confident..comfortable styles and build from there..it is very different from heeling indoors to heeling outdoors,especially going up or down a hill as wimbledon where i live is full of them!!

BUT do it..its great fun and very liberating ,you only live the once so go out and enjoy!!

A tip ! pick a nice neighbourhood around dusk for starters!!

Thanks for the advice Bladerunner. Yes, I seek liberation from my fears and to release myself from this idiot social conditioning, where only women are tolerated to crossdress and have innovative dress codes...

[morpho]

good luck, forgot to say that i personally consider to dress full in femme ONLY for a public outing because it hides all my id and cannot be recognized easily, whereas in normal style, if I meet someone or somebody that know me or remembers me and maybe i dont remember, spotting me in heels is a great topic to gossip and i wouldnt know who is talking about me etc, and it can made my life a hell, since my wife doesnt know, sad but true. In femme is more challenging- yes, much more work- yes, too risky-no, i think less, because in anycase a Tg is a TG in public and no body gives a damn most of the time is accepted anyway, than a person that cannot be defined, people tend to check out the TV or TG and admire or criticaze the outfit rather than trying to id the guy., so in normal outfit is very likely that most of the public will try to get your id first. hope this opinion can help you. I am going to a different city to heel where nobody knows me for sure, and even that is so so hard to do, will say when and how later in a new thread.

[Dawn HH]

Johnieheel:-) Don't worry about going to Hell, just wear your heels and remember that you will not be alone. Misterd73:-) Let us know how you make out on your outing. Cheers--- Dawn HH

[sabotalot]

I'm so glad to have found this place. I really like 4-inch open-back "Candies" clogs. When it doesn't snow, I wear them everywhere. Lacking ok weather,I wear my Bastad (discontinued loafer-vamp style) clogs. They allow me to stomp-off the @#$%& snow o.k. Springtime and hh meet, please hurry!

[chris100575]

Wearing heels in public is 90% a mental thing. I used to worry that everyone would notice and either point and yell or actually assault me for wearing them. A few times out and I realised that pretty much nobody cares, and anyone who does is highly unlikely to make a deal of it. I've been laughed at once, by a lad of about 14 who was with two of his mates, and he shut up pretty sharpish when I turned round and looked at him. It's all about confidence, if you walk with your head high as though you're doing nothing at all unusual you're far less likely to attract unwanted attention than if you look nervous and shifty. Unfortunately this is easier said than done, especially at first. The remaining 10% is physical. I'd wear low heels that you can walk in easily to begin with, it's a lot harder to walk in heels outdoors where you have uneven surfaces etc to deal with. It's also going to take longer to get anywhere as you're probably going to be taking smaller steps than you would ordinarily. Your feet will also get sore. I realise this may sound like stating the obvious, but I was amazed how much harder it was to wear heels out in the real world than it is at home. My first serious outing I took a pair of trainers in a daysack in case the heels got to be too much. Tying the two together is the image you project. I think that boots work better with trousers than shoes do, but that's just me. Either way, red patent stiletto courts are not going to go with jeans and a T shirt. In a nutshell, if you pick shoes or boots that go with the rest of your clothes and you can walk well in them it's much easier to pull off. Usually with the boots in my avatar I wear black jeans, long sleeved black T-shirts and a long black leather coat. It's quite gothy which suits me and they all fit together. It's not everyone's style but it works for me. I hope this doesn't sound preachy, just wanted to pass on some of my thinking and hope some of it helps. Good luck! Chris

[misterd73]

good luck,

forgot to say that i personally consider to dress full in femme ONLY for a public outing because it hides all my id and cannot be recognized easily, whereas in normal style, if I meet someone or somebody that know me or remembers me and maybe i dont remember, spotting me in heels is a great topic to gossip and i wouldnt know who is talking about me etc, and it can made my life a hell, since my wife doesnt know, sad but true.

I'm affraid I am in the same situation. My wife knows that I like heels, but me wearing them shocks her.

In femme is more challenging- yes, much more work- yes, too risky-no, i think less, because in anycase a Tg is a TG in public and no body gives a damn most of the time is accepted anyway, than a person that cannot be defined, people tend to check out the TV or TG and admire or criticaze the outfit rather than trying to id the guy., so in normal outfit is very likely that most of the public will try to get your id first. hope this opinion can help you.

Hmm, interesting perspective. Yet, I have no experience on CD/TV at all... it's something I'd like and probably will try. Yet I need some additional motivation to try that. You have a good point though.

I am going to a different city to heel where nobody knows me for sure, and even that is so so hard to do, will say when and how later in a new thread.

Yes, I'm not going to try my heels out for the first time in my home village - especially because I live in the countryside, where people are more short minded, in what concerns "heeling for men".

But thanks for your points of view and suggestions. Much appreciated.

[misterd73]

Johnieheel:-)

Don't worry about going to Hell, just wear your heels and remember that you will not be alone.

Misterd73:-)

Let us know how you make out on your outing.

Cheers---

Dawn HH

Hello Dawn,

Thanks for the encouragements! Yes, i'm surprised to see how many men actually love wearing heels! I'm very happy to be a member of this community and it's already helping me make some "mental" progress, if I may say.

I will fully document (well, as best as I can, considering that I will be alone...) and post a written report here.

It will happen as soon as I can have at least four ours alone or off from work, which is quite hard, considering that I'm married with two kids...

If only I could "brainwash" my wife into liking men in heels...

[misterd73]

I've been laughed at once, by a lad of about 14 who was with two of his mates, and he shut up pretty sharpish when I turned round and looked at him.

Must have been an unpleasant experience though...

It's all about confidence, if you walk with your head high as though you're doing nothing at all unusual you're far less likely to attract unwanted attention than if you look nervous and shifty. Unfortunately this is easier said than done, especially at first.

I'll try to bear all that in mind, thanks for teh advice...

The remaining 10% is physical. I'd wear low heels that you can walk in easily to begin with, it's a lot harder to walk in heels outdoors where you have uneven surfaces etc to deal with. It's also going to take longer to get anywhere as you're probably going to be taking smaller steps than you would ordinarily. Your feet will also get sore. I realise this may sound like stating the obvious, but I was amazed how much harder it was to wear heels out in the real world than it is at home. My first serious outing I took a pair of trainers in a daysack in case the heels got to be too much.

I was considering doing it on a long flat, paved surface like a promenade around the sea. I plan on doing this in the morning and hopefully it will rain, so there will be even less people out...

Tying the two together is the image you project. I think that boots work better with trousers than shoes do, but that's just me.

I fully agree with you.

Either way, red patent stiletto courts are not going to go with jeans and a T shirt. In a nutshell, if you pick shoes or boots that go with the rest of your clothes and you can walk well in them it's much easier to pull off.

Yes, I am planning on going "casual", with these boots: http://img299.imageshack.us/my.php?image=bottes5dm7.jpg

I think it should do it nicely with a brown or beige coat...

I hope this doesn't sound preachy, just wanted to pass on some of my thinking and hope some of it helps.

Good luck!

Chris

Not at all! Thank you for your advice. Knowing that lots of people have already gone out with their heels is an extra motivation for me!

[Bootking]

Misterd, the boots and jeans are a good choice. I would strongly recommend starting in an area where you are not known, this way you do not have to worry about people that you know. Good luck!

[misterd73]

Misterd, the boots and jeans are a good choice. I would strongly recommend starting in an area where you are not known, this way you do not have to worry about people that you know. Good luck!

In fact, I just did it!

Yet it didn't happen as I was planning!

As other members have asked me to make some pics of the "event", here they are. Learn all about my first time here: http://misterdshighheelsexperiences.blogspot.com/

Please excuse my "excessive enthusiasm", as I'm not so "advanced into heeling" as much of you.

Enjoy the reading!

[Mr. X]

In fact, I just did it!

Yet it didn't happen as I was planning!

As other members have asked me to make some pics of the "event", here they are. Learn all about my first time here: http://misterdshighheelsexperiences.blogspot.com/

Please excuse my "excessive enthusiasm", as I'm not so "advanced into heeling" as much of you.

Enjoy the reading!

Very nice Mister. The site looked great and so did the shoes. Good read too.

[misterd73]

Very nice Mister. The site looked great and so did the shoes. Good read too.

Thank you very much Mister X! Glad you liked it!

[kikepa]

Well, that depends - out where? Taking out the trash? That would have to be grade school. Out where others saw me? That would be college, using Halloween as a cover. For real, as myself, wearing heels in a public place? That would have to be about eight years ago, going to the movies. I felt self-conscious as could be! But I did it, and tried to ignore the few glances. One guy was determined that I observe him staring, so I made a point of pretending I didn't see him. He started getting out of line, so I left the concession line and returned later, missing part of my move, drat him.

[euchrid]

A slight Freudian slip there perhaps, johnieheel !?!

...

the first time I walked into a church I thought God was going to condemn me straight to heel and I was really scared! No Kidding!

[Thighbootguy]

DawnHH has given excellent advice (as usual). Look in a mirror and be sure you are comfortable with what you are seeing. You have to be comfortable if you are going to go out with confidence and having confidence is the critical factor in the whole adventure. You have to be able to say to yourself, “This looks good and I like the way it looks.” Going out away from you home is a good idea but don’t worry about going to a deserted location. Ok, first time go to the deserted location but then find a populated place and take a stroll. I recommend a bookstore or mall. The first time it will take some to get out of the car, but that is normal for a first (and second outing). Once you go out in public, and discover that nobody cares what you have on your feet, you will have a great time. The key to the whole adventure is having confidence in yourself. If you do, others will recognize it and give you plenty of space. Enjoy your heels.

[misterd73]

Once you go out in public, and discover that nobody cares what you have on your feet, you will have a great time.

That's what I need to do next...

[Dawn HH]

Misterd73:-) That was a great account of your adventure in driving your truck in 4" heels and seeing the pics ment a lot in our enjoyment with you. Thanks for sharing with us all. Now that you have broken the ice, it will be easier the next time. Go out and have fun and build your confidence and be sure to let us all know just how you make out. Cheers--- Dawn HH

[maxhh62]

Hallo misterd73. I'm from north Italy and I have tree kids and my wife doesnt like me in heels. My town is a little town and I cannot wear heels on the street with daylight so usually I go out in heels (and long pants that i wear only with heels) only in the evening using cowgirl boots or boots with large high heel. When I go on holidays in foreign countries like France or Germany I feel more free. Last year I bought a fantastic pair of cowgirl boots with 8 cm. heel in Germany because there normal size of women shoes is also 41 42.

[Magic Heels]

MisterD Well done, superb pics, I liked the boots with a skirt. It shows them off better! I do the same and it is great fun!