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Weekend Adventures and then some....


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I started this weekend off with renewed confidence and an abundance of support from my loving wife...I knew that I would wear heels out (finally!) after too long being on house arrest, but I had NO idea what a ground breaking weekend this would be. It started out on Saturday and dinner out with my wife while wearing my 3 1/2 inch block heel, knee high Nine West black boots (pictures are in my album) with my jeans and a nice dress shirt, then a leisurely walk around Target. Sunday, my wife talked me into wearing the same boots to my Family Birthday Party...my heart was racing, but I did it - the whole day Sunday in my heeled boots! The only time anyone even noticed was when my Mother lifted up my pant leg because she thought she saw something stuck to my heel - and she didn't even say a word (yes, I've already told her about my interest in heels, and yes, she's fine with it). Next, because I had today off, I invited my Mom to go shopping with me at the local mall. Once again, I zipped up my beautiful black boots and toured the mall without even flinching...amazing! We went out to lunch and a couple other stores, but no one even seemed to notice my footwear. It was so liberating and I had such a great time. Best of all was tonight...after dinner, my wife and I went out to the grocery store. I decided to kick it up a notch and put on my brown 4 inch stiletto Nine West pointy toed boots. No panicking, no heart racing, no nervous sweat...I was fine! We were there about an hour and other than the floor being slippery, I maintained my confidence and poise and carried myself as I usually would. My wife was so proud of me...she couldn't stop saying it! As I sat down in my truck on the way back home, I took a deep sigh of satisfaction. I've always wanted to get the guts to wear my stiletto boots out and about, now I finally have and I'm hooked! :chuckle:

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What a fantastic experience! Though I wear heels a lot, I would never dream of wearing them around my family. You are a lucky guy and I am glad to see that you are off to a great life in heels.

Style is built from the ground up!

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Thanks for the encouragement and support HappyFeat. So many people here have helped to inspire me, yourself included. After reading about others experiences and seeing pics of what others are wearing out in public I always think to myself, "Well if he can be comfortable wearing a skirt and heels out then I should be comfortable enough to wear a pair of my boots under jeans." Thankfully for me, I have a wife who is very supportive and encouraging of my heal wearing. In fact it is something that we have a lot of fun with. As far as my family is concerned, my mother has known for several years and is of the opinion: if I'm happy and not hurting anyone then that's what matters. While I haven't discussed it with my father, I have a feeling that he already knows but hasn't said anything. I can only assume that because the rest of my family is used to seeing me in nothing but cowboy boots, that so far the only time they question my footwear is when I'm wearing sneakers. Trust me it was scary as hell, but I'd like to hope that my family loves me enough to accept me for who I am. More advendtures to come!! Cheers, NH Heels

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Ok, so i know that I just posted but I can't help it. Today I put of my black Nine West 3 1/2" block heel boots with a longer pair of jeans and a maroon button down shirt and headed out with my wife. First stop was to pick up my mother and my 11 year old sister. We headed of all places to our churches holiday craft fair, where we were sure to see many people that we know. We saw many old friends, bumped into an old girlfriend and her mother, talked to one of our priests and walked around for at least 2 hours. If anyone noticed my heels, I really don't even care. It was a great experience and I'm glad that my wife talked me into it. After dropping my mom and sister of at home, we headed to the oultet mall up north. Spent way too much money in Old Navy(all Christmas gifts), walked all around poking in all of the stores that we wanted and still no issues. When we finally went into the Nine West outlet, I was like a kid in a candy store. We looked around for a while and I was determined to try on at least one pair of boots even if I didn't buy anything. Sadly I was not overly impressed with the selection of boots, but I did try on a pair of stiletto knee boots with a semi squared toe. I really didn't like the look of them enough to justify buying them just for the sake of buying something. I was a little disappointed since I had been looking forward to our trip to Nine West for at least 2 weeks. We did end up stopping at our local Off Broadway Shoe on our way home. This is where I again tried on another pair of boots (3 1/2 block heel, round toe, black knee boot) which I ended up buying. These are definitely another pair of boots that I will feel comfortable wearing out and about, hopefully tomorrow. Over all another successful heeling experience. More to come, NH Heels :cry1:

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Thanks guys. I need all the encouragement I can get. This place has definately been a great help. I only hope to help others the same way. :cry1:

I agree with you that theis website has been such a great inspiration. Congratulations to you and I hope you realize how lucky you are to have someone so supportive of your high heel desires with you. Thank you for sharing with us.

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Happy Belated Thanksgiving everyone...had a great day, although heel-less until 8pm, but today was another great outing. After working all day, my wife coerced me to do some Christmas shopping with her, and of course, she made sure that I was wearing heels! I pulled on a pair of brown, calf-high, rounder toe, cowboy boot-style 3 3/4 heeled boots - they looked great paired with my jeans and a nice t-shirt. We went to dinner, then off to Target where we walked the entire store. The boots were so comfortable and, once again, I don't think anyone noticed. I'm becoming more confident in my heeling and I didn't even really think about it - it was great. I still have to post pics of the boot that I bought last week, but I have posted some of the ones I wore tonight. Taking one day at a time, NH Heels :cry1:

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After a long day at work the only thing I could think of was coming home and putting on my heeled boots. When my wife suggested going out for supper and doing some Christmas shopping I was siked. Another chance to go out and maybe push my self even just a little. I went to my closet to try to find a nice dress shirt to wear with my long jeans and maybe my black Nine West stiletto boots. After going through every shirt I own and not really finding anything I thought would look good or wasn't wrinkle I had one of those moments where i questioned everything. I collapsed on the bed in complete dispair and disgust and wondered exactly what the hell was I thinking. I had lost all of my self confidence in a heart beat and was ready to give up. After about a half hour of hemming and hawing and realizing that I was trying too hard I decided to just put on the same brown 3 3/4 cowboy style boots I was comfortable with last night and a maroon long sleeved t-shirt and just try to get a grip. I knew that I looked good and felt confident enough to go out, just a little dissapointed in my self. When I went dowstairs my wife complimented me on my outfit but was curious as to why I had decided against the stilettos. We headed out to dinner and while I wasn't worried at all about what I was wearing, I was a little dissapointed about what I could have been wearing if I hadn't freaked out earlier. Dinner went well though and so did our shopping trip to the local Kohl's. I don't think that I spent any time at all worried about others seeing what I was wearing, I was far to concerned with my own self image and comfort. I know that if I hadn't been able to at least wear the boots that I did that I would have been kicking myself for the rest of the evening. In the past if I had a moment of self doubt no matter how badly I wanted to wear my heels out, I would've chickened out. I know that I am slowly becoming more comfortable and confident I just need to remember to not over think everying and take it one step at a time.

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Sounds like your really getting the hang of it NH. Sounds like you also have a very supportive wife like mine! When I first joined this site a few years back, it seemed like not so many of us were going out in heels. I think more and more are seeing our posts and finding out there is really nothing to fear. Thanks for sharing.

real men wear heels

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Thanks Johnieheel. I know that most of my issue is in my head. I even often refrain from posting here because of my own fears. I am trying to work through this. My wifes support and a need for my own sanity combined with reading others posts here have helped so much. Cheers, NH Heels (Jim)

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Sunday was a quiet day with my family to celebrate my fathers' birthday at my parents house. I wore my black 4" heeled cowboy boots, a black button down dress shirt and boot cut jeans that didn't cover any of my heels (as this is for some reason the only way I can wear these boots). My younger brother and his gf, my little sister who's 11, and even an elderly neighbor/family friend were all there for dinner and then cake and gifts. As usual there were no comments on my boots whatsoever. We had bought my father a pair of jeans among other things. At one point he went to try them on to make sure they fit. When he came out of the bedroom he wasn't wearing any shoes, so the pant legs were dragging on the floor a little. My wife commented that they would fit better when he had shoes on, to which my sister chimed in "Yeah, maybe you should put on a pair of mom's high heels!". I had all I could do to contain my laughter. It blew over quickly and the day went on. It was another good day for me, completely stress free and just enjoying myself. Tonight my wife and I needed to go food shopping after supper. I was already wearing my longer cut jeans with my black, pointy toed, 4" stiletto heeled, knee high boots. After supper, my wife asked if I was ready to go and I told her that I needed to change out my boots as I am still trying to strech out this particular pair a little and am still unsure about going out in stilettos even though I've done it once before. I went upstairs to change into another pair of boots and once again almost lost all of my nerve. Instead of getting all worked up about it, I called for my wife to come and help me make a choice. I was torn as to which to wear, but when I asked her to just tell me which she preferred she told me to keep what I was already wearing. My decision was made! We headed out to the store, where I hardly hesitated to get out of the car and walked head held high into the store. We walked the whole store, up and down just about every aisle, and although the store wasn't really busy, there were definitely plenty of people around. Once again, I didn't notice any looks or comments from anybody! Seriously, with every successful adventure, I feel more and more sure of myself and happy that I've finally taken the "steps" (pun intended) to live the way I want to live and wear the shoes that I want to wear.

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  • 2 weeks later...

NH Heels, What a coincidence that both of us had our breakthrough weeks of heeling, at almost the same time, recently. I feel that my recent outings in boots brought me a little bit closer to my wife, and made me appreciate what I have. I won't take her for granted. I enjoyed reading your posts.

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Kittyinboots, It is an interesting coincidence. I try very hard not to take my wife for granted. She has always known about my interest in wearing heals and has always been supportive. I have found over the years that my interest has only grown even though there have been long periods of trying to turn it off. This of course upsets my wife since she loves me for who I am and honestly loves me in heels. I on the other hand always felt like I was hiding something and felt like I was always on the defensive, which would cause me to become depressed. Over the last few months though, I have done a significant amount of healing (for me at least). My wife and I have noticed a difference in my attitude and I am overall a much happier and relaxed person. I still have my moments when it comes to going healing, but I am able to get through it. I realize that I don't always have to push myself. Sometimes the status quoe is ok. I have several pairs of boots that I know I am comfortable wearing out and that's what I'll wear rather than always trying to amp it up. Sorry if I've been a little long winded, just trying to get things off my chest. Hope to share more stories soon. NH Heels

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My wife and I have noticed a difference in my attitude and I am overall a much happier and relaxed person.

Funny you should mention this aspect. I used to have an identical problem. My mood became very "shitty" when ever I tried to quit or I didn't wear my heels for a couple of months or longer. When I decided not to try and quit wearing heels, ever again, my mood became stable and I was actually a pleasant person to be around. The burden was lifted and I felt like I was "free." I wonder how many other of our heel wearing guy members have experienced something like this?

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

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Thanks Bubba, it is really awesome for me to find out that I am not alone. It has been a lot of help to share experiences and thought with everyone. Just being able to verbalize and get things off my chest has been good for me. I totally understand the feeling "shitty" thing and am glad to be mostly rid of it. I would also be very interested to find out if there are others that have had this same feeling. It's just not worth it to feel that way and if I'm a happier person for my heeling then so be it. My wife is enjoying the happier me also. :cry1: NH Heels

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NH Heels, Hell no you are not alone but indeed among a crowd of people, genetic guys and girls alike, that know pretty much who they are and that high heels are a natural part of their identity. Like Bubba136 says, my mood would probably be extremely negative if I quit wearing heels for a period of time. I have become very accustomed to wearing 5" heels in the car and have worn 4-5" heels in a few malls and IT IS LIBERATING to say the least. Your wife's support is invaluable and will only help you stay on your path. Your life, as well as all of ours, is a one-shot deal; better we enjoy it even more with high heels or whatever else you might want to wear with them! I'll click my shoes together and wish you only the best! HappyinHeels

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I haven't had a whole lot of noteworthy outings lately but I did buy a new pair of boots on Sunday. My wife and I were out Christmas shopping at the mall. Managed to make our way to the shoe dept at JC Pennies. While I found several pairs of awesome boots that I would love to add to my growing collection, I have been on the hunt for a pair with a chunckier heels that I would be guarranteed to feel comfortable wearing out (maybe without covering the heel). I saw one pair of knee boots with a chunky 2 1/2 in heel and a rounded toe that I liked, but felt the heel wouldn't be enough for me. I then found a similar pair of midcalf, 4" chunky heel boots with a round toe that i like even better. My wife got a female SA's attention and asked her if she had them in a size 10and she went outback to find them. She returned with the boots in my size and I somehow found the nerve to let her know that they were actually for me and asked if there was a backroom or somewhere discreet where I could try them on before buying. Without skipping a beat she led me to a hall that led to the back room and said that my wife and I were welcome to try them on there. I proceeded to pull off the cowboy boots that I was wearing and take the boots out of the box to try them on. I was on the fence about the round toe, but decided that they fit well and were comfortable so on to the register we went. I know that I should have just tried them on out in the open, but one step at a time. At least I tried them on in the store so I count this as a success. NH Heels

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I can really relate to those feelings. Society tells us that somehow this isn't right, but even though on the rational level I know better, on the subconscious level it keeps eating at me and causing enormous amounts of stress. Hence it is every time still a struggle to do what I want to do. My wife is very supportive and helps me a lot, but still I have a feeling it is my struggle and I don't want to burden her more with it than necessary. Maybe I am oversensitive. I hope to sooner or later find the inner peace that allows me to get rid of this stress. But this may still take quite a while. Y.

Raise your voice. Put on some heels.

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I haven't had a whole lot of noteworthy outings lately but I did buy a new pair of boots on Sunday. My wife and I were out Christmas shopping at the mall. Managed to make our way to the shoe dept at JC Pennies. While I found several pairs of awesome boots that I would love to add to my growing collection, I have been on the hunt for a pair with a chunckier heels that I would be guarranteed to feel comfortable wearing out (maybe without covering the heel). I saw one pair of knee boots with a chunky 2 1/2 in heel and a rounded toe that I liked, but felt the heel wouldn't be enough for me. I then found a similar pair of midcalf, 4" chunky heel boots with a round toe that i like even better. My wife got a female SA's attention and asked her if she had them in a size 10and she went outback to find them. She returned with the boots in my size and I somehow found the nerve to let her know that they were actually for me and asked if there was a backroom or somewhere discreet where I could try them on before buying. Without skipping a beat she led me to a hall that led to the back room and said that my wife and I were welcome to try them on there. I proceeded to pull off the cowboy boots that I was wearing and take the boots out of the box to try them on. I was on the fence about the round toe, but decided that they fit well and were comfortable so on to the register we went. I know that I should have just tried them on out in the open, but one step at a time. At least I tried them on in the store so I count this as a success.

NH Heels

Great boots!:cry1:

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

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My first outing, with a lady friend, was a long time ago but I remember it like it was yesterday. Of course you need to know my friend was pretty straight forward, as in after asking her to wear heels for me the second time she looked me straight in the face and asked "so what size are your high heels?" That sort of shocked me but I didn't hesitate to tell her my size. From that point on we experimented outside the house, driving around at first then going to parks to walk around. Probably the most exciting time, being a first in public, was when we went to a mild adult bookstore together. Although I prefer to wear stilettos I toned it down to a pair of my boots that had a 2 1/2 inch block heel. I worn them under jeans but I didn't realize how noisy they would be on the store's tile floor. As we walked around the store the definite click clack could be heard by all, which raised a few eyebrows. Even though you could plainly see I was wearing heels I think most of the attention was drawn to my friend's five inch pumps. From there I was hooked, unfortunately our relationship drew to a close about a year later but it was still an experience I will never forget and one that I have repeated by myself a number of times.

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