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My heeling out experience!


latindancer

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I just don't understand why you guy's women will not except you as you are in heels. I started training another girl on one of the machines at work and as usual, I bring up high heels. Well she loves them as much as I so we have had a lot to talk about. Then when I showed her a pic of me in 4" and 5" stiletto's, she was a little surprised at first and then it became a normal conversation about what shoes to wear with what. We have been talking like two normal adults about what looks best with what heels, on me and on her. So now I am working with two women in which I sold one of them 3 pair of my heels and having conversations with both. What I'm saying is that 99.9% of the women I talk to about me or men in heels agree that it's a good thing. Just to be yourself. So now when I run into them at walmart or where ever, it's no surprise, and it happens a lot.

real men wear heels

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Johnnieheel,

I think that the answer is that people are different; indeed there are also cultural differences that also are barriers. When it is all said and done, my wife will "tolerate" the heel thing at home - but that is as far as it goes. She knows that I have heels in the trunks of the cars and chooses to ignore it as much as possible.

As far as heels while driving in the car, she is concerned about being stopped or being in an accident (obvious embarassment on her part - not so much mine; I could deal with it).

So, I have to take the positive with the negative - heels at home and not outside (when she is around). When she is not around, I do what I want to do, in the car or otherwise. If she changes over time, great and I would certainly encourage that by talking about it, etc. etc. But if not (and she really wishes the whole thing would go away), I have to accept her for who she is as she does me. Of course, all of that is within limits on both sides.

It's all about the heel!

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Bootking-I like your new avatar. It looks good. Well, just wanted to tell everyone about my last couple of nights. It was awesome and exciting. I have this tight mini-skirt that I like but never had the guts to go out in it. Well, saturday, I put on some makeup for the first tiime, just to stay at home. I put on my mini-skirt with my nine west 4" pumps and suntan hose. I have to say that l looked good. I didn't have a bra or anything else but it felt good. After an hour, I decided what will be wrong with going for a drive with the way I looked. It was night though. I was driving around and after a while I got thirsty. I went to a Dunkin donunts and didn't know what to do. Finally, I said skew it and went inside, it didn't have a drive-thru. Talk about having my heart come out of my chest. Just picture, a guy with a tight mini-skirt comes in with nice legs, makeup, no wig, bald(clean shaven) and ask for coffee with a strong male voice. Ha, but the guy at the register did nothing and served me. It was awesome. I love the way I felt. The heels, skirt and hose made me feel like a million dollars. I was excited and happy as one can be. Well, on the way home I stopped at a gas station cause my windshield wiper fluid wasn't working and the front windshield had a lot of salt buildup. I cleaned the windshield as was about to leave when I noticed 2 girls inside the gas station. No one was around, so I said screw it. I went inside for some water. I got my water and went to the register. Nothing. Not even an wow. Well, I finally asked them a few questions. I asked them if I was missing anything. One girl said "oh my god". I asked her, what? She actually thought I was a woman, that shaved my head. Now, I know I don't look like a woman, but she said I did a great job with the makeup, and the way I walk, and legs confused her. HAHAHA:clap: The other girl also complimented me on my makeup and wanted to know why I was dress like that. I told her I was going to a party and wanted to know what I was missing. Of course, the obvious, wig, breast, and earing/jewelry, other than that, perfect. As, I was walking to the car, a guy came out of his car, and was looking. I didn't want to deal with it, so I said. I'm going to a party. The guy obviously knew I was a guy, you know the baldness kinds of tell it, but he said. "Don't worry, you look sexy away." Talk about a high.:santa_hat: I LOVED THE WAY I FELT. Just wanted to say that. When I got home, I felt couldn't believe I did what I did. 4 months ago I would never of gone out like that, even during Holloween. Now, I just went out like that and said screw it. It was the best feeling I had in a long time. I loved every minute of it. The pumps, walking in heels, the mini-skirt, the feeling of hose, and the way they felt together was wonderful. Plus, knowing I had makeup on, and the way people reacted was amazing. I have to say again thank you for everyone on this site that gave me the courage to go out in heels and now is giving me the courage to do as I want. So, one more time THANK YOU. Latindancer

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Latindancer –

That was a great outing. From experience, I know exactly how you felt. A guy going out in public as a guy in a skirt and boots can be an extreme high (and even higher when you talk to someone).

I hope you have had time to come down off the high and to get your pounding heart back into your chest. You just had a super outing and are feeling great but be aware that that feeling is addictive. It is real easy to get hooked on that excitement. I’m not suggesting that going out was a bad thing but getting addicted to anything is a bad thing. You have pushed your envelope from guy shoes to heels at home, then to heels in public, then to skirts heels and makeup in public in a fairly short period of time. Each step builds on the previous one and is more exciting than the previous one. It’s real easy to get addicted to the feeling you get by pushing your envelope further and further.

My advice is to not be in a hurry. Slow down a bit and enjoy things. Become aware of what you are doing and make sure you are really comfortable doing it and not just doing it for the excitement ie. addiction.

If you go too fast it is real easy to overshoot your comfort level. I say that from experience. All of a sudden you see yourself and wonder what the f- - - you are doing. This is not a pleasant experience. Several of the folks on this board have been there and done that.

My 101 year old aunt used to tell me “Quality work takes time”. Although she didn’t have guys learning to wear skirts and boot in public in mind, it’s still good advice.

Bootking – great avatar

I dream of a world where chickens can cross roads without having their motives questioned.

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TBG-Your right about the high. I had a huge high for the whole day yesterday. I still can't believe that I did what I did. I understand about your comment and your advice. I will like to do that again, but understand that I must take it slow. Hopefully I can buy everything else that I need in order to go enfemme and try to pass. I really want to be able to go out in a dress and see if I can enjoy an evening like that. The only problem will be trying to stop guys from hitting on me. Will not like that. I will like to just go out. Just like you said, I must take my time though. Thanks for the advice. Latindancer

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My dream was to one day just be able to go out in public just like women do in heels and just be me. That day has came a few years ago and it just keeps getting easier. I really don't care if I get attention or not. I just love being able to wear my heels as a NORMAL every day part of my wardrobe but a nice complement here or there would be nice.

Johnieheel

I agree with you in that I look forward to the day when we can wear heels as part of "normal" attire. I agree with Bootking that cultural barriers is a problem. My wife is not keen on my likeing heels and it come from the culture she grew up in and she is fairly open minded person. My wife is 5th generation Texas spaniard whos ancestors came to Texas from spain on spanish land grants. Part of the spanish and the mexican culture is a male dominate society they call it machismo and men should never want anything feminine. When I first talked to her about my likeing womens shoes the first thing she asked is are you gay? I told her no I just like heels she thinks I will lose my masculinity she is slowly comming around but it is a very slow process and therfore alot of my heel wearing is done alone, I would love for her to be with me but that may not happen for awhile LOL.

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billyb, how true! Culture has a lot to do with expectations and beliefs. Change will take time, if ever. My wife is from the Caribbean and similar attitudes prevail although she has been here for 25 years and is okay with heels in the bedroom! Once in a while though, I hear the little remarks that she is not entirely happy about it but tolerates it.

It's all about the heel!

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Johnnieheel,

I think that the answer is that people are different; indeed there are also cultural differences that also are barriers. When it is all said and done, my wife will "tolerate" the heel thing at home - but that is as far as it goes. She knows that I have heels in the trunks of the cars and chooses to ignore it as much as possible.

As far as heels while driving in the car, she is concerned about being stopped or being in an accident (obvious embarassment on her part - not so much mine; I could deal with it).

So, I have to take the positive with the negative - heels at home and not outside (when she is around). When she is not around, I do what I want to do, in the car or otherwise. If she changes over time, great and I would certainly encourage that by talking about it, etc. etc. But if not (and she really wishes the whole thing would go away), I have to accept her for who she is as she does me. Of course, all of that is within limits on both sides.

Bootking: I do understand. There are more important things in life than shoes to be realistic.

Johnnieheel, that's guts! To go out dressed lower half "female" but as a guy - incredible! My hats off to you too, thighbootguy!

Glad you guys like the avatar!

I think you got the wrong guy Bootking. I don't wear skirts. Just mens pants and heels.

I do like your avatar though.

real men wear heels

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TBG-Your right about the high. I had a huge high for the whole day yesterday. I still can't believe that I did what I did. I understand about your comment and your advice. I will like to do that again, but understand that I must take it slow. Hopefully I can buy everything else that I need in order to go enfemme and try to pass. I really want to be able to go out in a dress and see if I can enjoy an evening like that. The only problem will be trying to stop guys from hitting on me. Will not like that. I will like to just go out. Just like you said, I must take my time though. Thanks for the advice.

Latindancer

I've been reading your posts with avid enthusiasm, but wonder if you just missed the crux of TBG's post?

If you really wanted to take your time, why would you expressly state your desire to go "enfemme and try to pass" in the same post?

It's your life and you can do what you want with it, but I'm just saying....

:santa_hat:

Feminine Style .  Masculine Soul.  Skin In The Game.

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Kneehigh- I understood TBG's comment completely. I stated that I wanted to go enfemme cause I will eventually like to wear what I did without having the looks and comments that a guys whose wearing a skirt, hose and heels will normally get. There are a lot of days that I will like to not get anything and be able to wear the female attair that I have without those looks. Something I always wanted. I understand the high came from what I was doing and wearing, therefore, I need to take my time due to not doing that before and also a lot of people are not use to it. Therefore, them seeing a man doing that will cause a lot of issues. Put, I understood.

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I haven't posted anything in a long while. I've been busy doing a lot of things, like trying to find a new job and probably relocating to Florida were my family is at. I've been wearing my heels on a regular basis. Mostly they have been very visible and I really don't care, but recently I have been more concious of what people do think. I went to a OfficeMax, and a couple of girls laughed when they noticed, after that they were very nice, but I didn't enjoy that. Overall, I have my don't care days and my do care days. I thinking of spoiling myself in with a Vegas trip. For the people who have gone to Vegas and did their heeling, what kind of heels did you wear and did you wear skirts?

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"Overall, I have my don't care days and my do care days." On my "do care days", I simply don't wear heels. I also have days where I don't want to go through the whole dressing up/shaving thing just to wear my heels. I can't simply throw something on and go out with them since they require a coordinated look. So, I just wear masculine shoes although I tend to keep a coordinated look when wearing purely masculine clothing as well. You know what they say, "What happens in Vegas stays in Vegas". I think you could get away with almost any outfit in that town.

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I was in Vegas from Dec 31 to Jan 6. I wore men's style heels (4") everywhere. I have several pairs and bout some there, trying them on in the mall. No one even blinked. One guy at the Golden Nugget asked me if I was wearing heels. I said yes. He asked if they were men's heels and I said they make them but they cost a lot more. We had to go but it was a positive experience. I think he wanted to find some for himself. Have fun in Vegas CJ

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  • 2 weeks later...

I haven't posted that much lately and I won't be posting for a while. I have a feeling that my heeling out is going to deminish during the next couple of months because I will be moving in with my sister who doesn't know, or she does and I don't know. Basically until I find a job and find a place to live I will not be going out that much or heeling. I will try some times. Other than that nothing much is going on. Well, let me tell you about Vegas. I got there and after I went to the room change into my stilleto boots and decided to go for a walk on the strip. I walked basically from the Tropicana and all the way to the Bellagio. That's about a mile or more. I walked all over the casinos and decided to see the water fountains at the Bellagio. Then I walked back. Overall, it was 6 hours in my boots. No comments or looks. Inside the casino I did get a lot of looks but nothing. It was fun. As soon as I got into my hotel, my balls of my feet where killing me. I thought that my feet hurt cause of the amount of walking that I did. The next day I walked in my sneakers and felt the same thing after a long time of walking. I noticed that it wasn't the shoes, but the amount of walking. Then I change to my heels. I went into the MGM Grand and a lot of people were looking because they were very visible and not my boots. Fun stuff. Got dressed enfemme the next day and no looks or comments. I did get a little laugh from someone that noticed that I was a man dress in female clothes. But everything was cool. I actually got to use the slots enfemme in which I thought would never happen. I didn't win anything but it was fun. I even went across the hotel to the MGM Grand and nothing. It was a fun time. Got dressed on more time in total woman clothes and went to the Walmart here in Chicago. No one noticed again, not even the woman that knew me as a man in heels/skirt. I walked again to one woman and finally after looking at me, did she recognize me.. ;) She told me good job and all that I need left is hormones. I said no, I like being a man and enjoy it to much to want to go that far. I told her I like woman way to much to do that. Moving next week to Orlando. I can't wait. Sun and warm weather. LD

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Moving next week to Orlando. I can't wait. Sun and warm weather.

LD

Gosh, the time to move out of Chicago is in August or early September. Not at the end of winter. Especially this winter.

Have a safe move and we will look for your return sometime this fall. ;)

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

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Hey Johnieheel - If you do come to Florida, then it will be me and CassieJ here. It will be our own little heel meet in Florida. HA! CassieJ stated many times that it's no big deal in Orlando either, so it will be fun. Thanks everyone for the comments. I will try to be careful. It stinks cause I just found out that it's going to rain on Monday(pack day) and snow on Tuesday(move day). That's all I need. Especially moving with a big truck and a car dolly. I just need to be careful. Everyone have a good weekend. LD ;)

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  • 4 months later...

Hey everyone, I must say that it's been awhile since I last wrote in this site and I have to admit that I miss it. I'm also been in florida taking care of family situations and haven't been able to go out cause all my stuff is in storage. I do miss it though. I miss my shoes and boots and everything else. I am amazed how quickly this thread just died... LOL Oh well. Maybe it will get going again once I start heeling again. I just have to get a job and a place and nothing. Well, one thing that has happened is that I meet a new person and told her about all the extra stuff I do, and her main response was "What sizes are you, maybe we can share?" Cool, I never thougth that will happen. Overall, I have been reading other post and I like seeing more and more people getting out. Hope to one day see other out, so I can give each one of you a thumbs up. :o I hope to be contributing to this thread more and hope everyone is doing well. Later LD

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In my serious relationships, once I divulged my heel wearing it ranged from "don't ask, don't tell" to let's have some fun. But never was an issue. I guess I was fortunate to have women for whom the shoes weren't a show stopper. Or they realized that in the greater scheme of life, what shoes you wear really doesn't matter.

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Hey everyone, I must say that it's been awhile since I last wrote in this site and I have to admit that I miss it. I'm also been in florida taking care of family situations and haven't been able to go out cause all my stuff is in storage. I do miss it though. I miss my shoes and boots and everything else. I am amazed how quickly this thread just died... LOL Oh well. Maybe it will get going again once I start heeling again. I just have to get a job and a place and nothing. Well, one thing that has happened is that I meet a new person and told her about all the extra stuff I do, and her main response was "What sizes are you, maybe we can share?" Cool, I never thougth that will happen.

Overall, I have been reading other post and I like seeing more and more people getting out. Hope to one day see other out, so I can give each one of you a thumbs up. :o

I hope to be contributing to this thread more and hope everyone is doing well.

Later

LD

Wow, meeting a new person like that right off the bat....you are a lucky man! Good luck in your new surroundings and please keep us posted concerning your future adventures in high heels.

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  • 4 months later...

Golly! I said "I'm glad I'm done reading it all!" Lol! Im kidding. I'm really looking forward to hearing more. Heh, you have loads of guts for the last bit, the "negative experience." I would have either cried or sweated extremely hard or something like that, lol. I'm still a teen, after all, and peer pressure's not a strong point with me quite yet. But I still venture out somehow. Brought outta me a similar story to yours. Something you couldn't do but just went for it anyways (good job, btw). I went to the mall a month ago. It was early, so I was sure not to come across any class/schoolmates. It was pretty cold, but I didn't care, and I threw on some open-toe wedges, 5 inches high! Lasted an hour in them, of only browsing stores really. Went to Macy's to see if they had anything of interest. Nothing :lmao: Went across to Carson's, on the way probably had some eyes on me for a second take while I walked, but I verged on. I walked to the "Shoes" section, not too far from the entrance. Passed some people along the way, but no look-downs. I was disappointed, but still went on to look at shoes. I cowarded out from being out in the open looking at heels while everyone were looking at mine. So I left here to a distant Bakers (coincendence, LD? lol). I got some eyes while walking, I bet, passing some teen girls as well o.o Well, guess I'm not gonna score them later XD Went to Bakers in hopes of seeing this girl I kinda liked :w00t2: But no luck D: Had to settle for someone new, and hopefully as well, lol. So I browsed and tryed on a few pairs. Some people came in, and I got kinda nervous cause a few of the people that came in, their child was teen girls or a little younger/older. (Well, not gonna get them either, lol) I held on trying any more on until they left, tryed some on, and on I went...to my truck, that is. On my way to the truck, however, passed some teens going into the Mall, some guys and a girl (o.o). As I passed, the guy must have commented on my footwear cause the girl said "You wrong!" and laughed aside of him. Oh well. Better experiences to come soon.

Formally "HHDude"

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Wow, I just looked at the number of people who viewed this thread over 12000. It's amazing. Hopefully, I helped some people to be themselves and do what they always wanted to do. HHDude- You already have experienced going out. I can understand the being young thing. I can't even image being 17 and going out in heels and trying to score a girl. Just understand that if you do, then the girl will know. Unlike you, we are already in our 30/40/50 and it's a lot harder to find someone. You still have the benefit of time. Experience and confidence comes from within. Once you have already done it, then it should be easy. I am not going to lie that there are days I chicken out, cause there are plenty of them. I just get the confidence when I do it and nothing happens, after that it's fun from there. Most of my confidence comes from curiosity. I am curious of why no one is saying nothing or doing nothing(not complaining), but I have an iquisitive mind. I'm curious, and I would like to know why. That's why even to this day, I will ask people why no response. Times are changing and people are being more accepting of letting people be. The ones that are not are just closed off or haven't experience life to what it could be. Keep heeling and eventually that confidence will build and then you will be able to do what ever you want when it comes to wearing what you want. Enjoy, relax, have fun and live life as you seen will make you happy. I know what I am doing is making me happy, therefore, I will continue to do it. Happiness will bring peace, and peace will bring that confidence everyone wants. Latindancer

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