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hiddenheels last won the day on September 5

hiddenheels had the most liked content!


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  1. During flying I've had a few people comment on how much they like my skirt, but never had a comment on the heels... My favourite was the security person, a young lady, commented how much she liked my skirt, but was sad that her mother doesn't allow her to wear something like it.
  2. Whenever I can, in or out, but it's a bit rare as finding time alone to do so is a challenge. Not nearly as often as I wish...
  3. Had a chance to fly recently. Each trip I plan out, what I want to wear on the flight. Have worn a 4" chunky boot once with skinny jeans, with the entire shoe exposed. That was fun, for the ~8h flight. Another time, on a ~5h flight decided to wear something a bit different, so wore some ankle boots from Steve Madded, 4.5" stiletto heel, white snake print (like these, but ankle only: https://www.amazon.com/Steve-Madden-Womens-Fashion-Natural/dp/B08BFM15NB/ref=sr_1_9?keywords=Steve+Madden+Snake+Booties&qid=1665974294&qu=eyJxc2MiOiI2LjkwIiwicXNhIjoiNS42NyIsInFzcCI6IjQuMTQifQ%3D%3D&sr=8-9). They were under some boot-legged jeans, with ~3" of shoe showing. No problems through security, obviously took them off. Enjoyed the entire trip, flight was uneventful. On the destination terminal, as I'm exiting, stepping onto the escalator, I hear this strong grinding sound. When I got off the escalator, I immediately noticed one of my heels is different, and recognized it the heel tip coming off. Awesome. I'm walking on the little metal thing in the middle of the tip, completely bent... I was sad. In between meetings I took it a nearby cobbler, he looked at it and told me $15 to fix, and he'll have to drill the tip out and replace it. 24h later, I had my boots back! Later that trip I did go for a long ~2h walk downtown with those boots on. That was a lot of fun! Unfortunately the heel started to wobble a tiny bit by the time i got back to the hotel, so am not quite sure whether something else is wrong with the heels, or it's normal... A few more flights over the last 6 months, but have been sort of alternating between wearing skirts, or heels, on the flight. Did want to wear 4" pumps once, but at the last minute switched the outfit out for a skirt instead... Just wanted to relax and take it easy, so skirts it was.
  4. Definitely agree. Our mirror is such that if I'm wearing heels, I'm too tall to get my entire reflection in the mirror, my head is outside the mirror, and things usually look good waist-down, but am still not completely comfortable with the entire image. Society's image of what a man/woman should be is deeply ingrained in us I assume. It has gotten much better over time, and I'm much more comfortable. Look at images online of what women wear, and try to copy those styles that I like, with a modification that above-the-waist it's my normal cloths, below-the-waist it's usually something from the other side of the store.
  5. What's so special about those? Just the scene it causes? My worry with something like this is actually fitting into the seat.
  6. Any chance you could either post a few links here, or send me a PM with them? Would like to have a look, just so I have a clearer idea of what you mean. Thanx!
  7. Was able to have some fun over the last week or so. - Went to breakfast to a hotel a few times. Once wearing torn jeans with dark blue 4.5" pumps. It looked fantastic, and I felt as such (one of the waiters -a guy- complimented me on the heels). Another time 4.5" white pumps with a white/pink mini-skirt. Another time dark blue mini-skirt with 4.5" pumps. Anxiety kicked in each time, but I made it through. The restaurant was usually full. - Torn jeans, with 4.5" chunky heeled mules (jeans go to ankle), took the metro to another city, walked around for ~5 hours, then went home. Shoes are super-comfy, had no issues. OK, my ankle went out 2-3 times, but was able to recover immediately. Aside from that, it was fun! - Same mules as above, with torn-jean-mini-skirt, went downtown for a few hours. Found a store that was closing, with a bunch of heels in the display. 80% off and such. Went in, a lot of it wasn't my style, but ended up trying on a few shoes, and buying 3 pairs. Paid like $45 total, totally unexpected purchase, but for that price I couldn't resist. The heels are awesome. One is a combat boot, but the best way to describe it is "cute"! Lady told me to try them on, no problem. - Coffee shop & a store in a black mini-skirt and a new 5" stiletto mule. The shoes are super-comfortable. Anxiety kicked in, but was defeated in 2-3 minutes. I don't get it... Some of these shoes are so comfortable, like I'm walking on a cloud! The two mules I mentioned above, I will be really upset when they break, as it feels like they're crafted to my feet and I could wear them all day. Wish I could do this more often... For all of these, I usually wear a nice shirt. Given that no breasts are showing, and I have stubble on my face, it's obvious I'm a guy. Been working a lot on my posture/confidence. I envy women who can do this without anyone batting an eye. But I rarely see any heels being worn.
  8. A week back had to go on an 8h flight. Wore some 4.5" chunky heeled shoes with jeans that go above the ankle. Jeans did nothing to cover the heels. Heels were like this but in brown: At security, everyone is walking through the detector with their shoes on, so I line up. When it's my turn, the guard points to my shoes, tells me to put it through the xray. Did. No problems at all at any time during the flight. It was fun! On the way back didn't feel like wearing heels, so ended up wearing black opaque tights with a black mini-skirt. Was super comfortable.
  9. Well said! Awesome point. I have been trying to pay attention to my posture, straight back, shoulders back, head up, show confidence. Just like anything, it's a work in progress. I can't do this with my wife, so taking videos or pictures is a bit tricky. I would love to see it, but it's a bit of a problem. I know what you mean though. I'll keep pushing myself. Have found that the anxiety does get better. Actually, let me rephrase. The anxiety level has gotten a bit better, but at the same time the heels have been getting more obvious! Hey, I understand. I am having trouble fitting my heels into the space I've allocated them, but can't resist. They're gorgeous, and let me have some fun! So I buy them. Although the standards have been getting higher, I want more padding, more comfortable shoes, and have settled on ~4.5" as the sweet-spot. I really wonder how frequent it is that a guy goes into a shoe store and tries on women's shoes. About a year back, I recall ordering online some heels for an in-store pickup in that exact same shoe-store. I did go in wearing heels, hidden as best as possible. Compared to this most recent visit, I would say it's progress.
  10. Sorry, do not like posting pics. Not a huge number of chances to do any heeling lately, or skirts. Did do one outing a few days ago. White shirt, denim mini-skirt, and 5" heels (like in the picture, except there's a small strap on the back). Stubble on my face, obvious I'm a guy. The shoes are the most comfortable heels I've worn. No problems walking in them. Bought them in a 2nd-hand store a few weeks back, but I love them. I don't feel like I'm wearing heels at all. Anyway, planned out a small trip. Went to a 2nd-hand store to browse around. Went in. A bit nervous, could feel my heart-rate and anxiety up there. After about 5 minutes calmed down. Checked out the shoes (nothing ), and skirts (nothing). Am not looking for anything in particular, just for "outstandingly awesome" items, like my boots from the previous post. No one commented. Was there ~15 minutes? Got in the car. A few days prior I noticed some really cute heels on sale at a local shoe-store, thought I would stop by the mall and see if I could buy them. This is a mall, quite busy, so the nervousness came back, but went in, went to the shoe-store, pointed out the two shoes I wanted to buy. The lady brought them out, I tried them on. Both were super comfortable, nice padding on the bottom makes a huge difference! Bought them. Went to another store to look at some cloths. Browsed around a bit. Was at the mall for an hour? Got in the car and went to another 2nd-hand store. Nothing there either. Then sat in a coffee-shop for an hour working. Got used to the skirt and heels I was wearing. Was quite comfortable in them! The heels look "manly" and the skirt was denim, also somewhat "manly". I don't know... My original plan was another skirt and stiletto heels, but wasn't too comfortable with that, whereas I think this worked well. I had fun. No one said anything.
  11. 'Morning! It's been a while. Busy life. Been progressing in my heeling, about once a week for a few hours is all I can manage. With the warmer weather I've been focusing on mini skirts, easier to style, and still love them. They're also easier to figure out how to actually wear without interrupting the peace at home. Skirts have become a quick favourite, I'm surprised how quick. I've lost all anxiety in wearing them out, I've gone shopping for skirts wearing skirts countless times now. Buying heels while wearing heels has still causing some anxiety interestingly. Anyway, this is not a story about anxiety. I'm still mulling over a recent trip. Weather was good, and I got it into my head that I really want to wear one of my pumps, a 4" matte black pair. Nothing fancy, but super comfortable. Weather is too good for pants, and I was experimenting at home, trying on different skirt combinations with shoes/heels, and found one I absolutely loved. Black mini-skirt with 3-4 pleats in it, plus the 4" black pumps, plus a white shirt (in-between dress shirt and t-shirt). Loved it. I **really** wanted to wear that. Could I? My hidden heels are not so hidden when wearing a mini-skirt. I figured I would compromise a bit first. I grabbed my 4" combat boots and 4" pumps, and headed out. First I stopped by a mall, and wore my 4" boots to test things out. Parked, walked into a near-by store I wanted to check out. I figured I'll see how this goes. Spent 20 minutes wandering and checking out some cloths. No anxiety, no stares, nothing. So I said, what the heck, and headed to the other end of the mall where I wanted to buy a specific skirt. Walked in. First employee I came across commented that she loved my shoes. I thanked her. Then spent at least 30 minutes looking at stuff, trying on a few things, and buying what I came for, plus a bit more. Then walked around the mall and got back to the car. At this point this was my 4th (I think) compliment on my shoes *ever*. Thought this is going well... In the car swapped over to the pumps, and drove to a large thrift store. While I have previously sat in the car sometimes for 10-15 minutes dealing with anxiety, this time I got out and just walked in. I have never worn a skirt with pumps out before. It's obvious I'm a guy, and I'm not trying to pretend otherwise. It was sooo comfortable. I felt *good*! I walked around, checked out the shoes and the skirts. No skirts to buy this time, but noticed a pair of ankle boots in my size. The front looks like cowboy boots, interesting. Pick it up,it's a 4.5" stiletto heel, even better! Looks perfect! $30. Then I notice the $200 original sticker on the bottom! Brand spanking new. As I'm checking out the shoes, this lady stops and tells me that I walk perfectly in the heels, and how she used to wear them but not anymore. I was a little surprised, so am not sure what I responded (but it was pleasant). But two compliments in a single day, never happened. I ended up buying the heels. The boot is super comfortable, brand new, and I just love it. So this is why I kept my heels hidden? "this" being no reason at all. It's all in my head.
  12. I'm going to post my outings in this thread, just to share. A few things about me: Have been married for a long time, with kids. My wife knew about my heels before we got married, but was never supportive, and eventually all heels became hidden (hence my alias) from view, we didn't talk about, I didn't wear it in front of her, nothing. Recently the topic came up, and the conclusion was that she said is OK if I go out periodically, she might join once in a while. It's slowly been improving, I showed her my heels, we discussed them, etc, but she doesn't want me wearing them at home. I'm used to that, so it's OK. Traditionally, 50% of my outings have been at night, with noone around, lasting about ~30 minutes. 50% of my outings have been to parks, or other more-deserted locations, during the day, hoping noone would be around. I usually wear jeans which cover the heels, and the heels vary depending on my mood. I much prefer boots, or ankle-boots, so it's almost always that. I have never ventured into a store or anything like that. Now I'm working hard to change that... More recently however, I've been getting really angry, sad, anxious, etc, most of it I am convinced is because of my inability (self-imposed or otherwise) to wear heels out. These emotions have been really difficult, and have preoccupied me greatly. I am getting really fed up with it, and have decided to try to challenge myself a bit and try to wear them outside. This is all recent, and has been happening in the last 2-3 months... OUTING A while ago I had to go downtown for work, and was in a huge mood to wear heels. I decided to take the required cloths with me, and a ~3.5" ankle boot that looks professional, no platform. After I was done with my work stuff, I quickly changed... Jeans covering almost the entire heel (about 1" was showing), and off I went. Broad daylight, with your general downtown population moving about, roads, etc. Put in headphones and walked around downtown, looking into stores, just browsing. Obviously lots of people saw me, but I was having fun. Didn't bother me who saw, and I didn't hear, was busy listening to music. Once I was done walking around, I walked too far from the car, so I decided to take the bus back. Got on the bus, in heels, sat down, and paid no attention to anyone. Was a bit self-conscious, but it was great. This was the first time I went out in public, ever, in broad daylight. I had a blast, still processing the experience. Cloths were: jacket, white shirt, very dark blue jeans, and black ~3.5" chunky heel ankle boots. The outfit I think worked perfectly. OUTING A few days after the above adventure, I got another chance. Was near a shoe store that I don't get a chance to go to often. Was coming home from a work-thing, and wanted to challenge myself. After my work-thing, I got changed, put on very long jeans, and a pair of 4" stiletto boots which I simply love. So comfortable. The heels could barely be seen. I got out of the car, shuffled around a bit, battling my thoughts, but then decided to just go for it. Ventured into the mall, past some coffee shops, and into a large department store. I looked around a bit randomly, just enjoying that I'm there in my heels. Then walked around the mall for a few minutes before making my way to the shoe store. I looked around, found nothing of use, then walked around the mall for a few more minutes and out to the car. The entire thing took 30 minutes or something, but it was broad daylight, with lots of people around, and I loved it. I was just a bit self-conscious. Cloths were: dress-shirt, black sweater, long blue jeans, and black 4" boots. I think it looked OK, upon reflection the outfit could be improved, but am still trying to figure that out. OUTING, OUTING, OUTING, OUTING A few days after the above adventure, over the course of ~2 weeks, I had the chance to be alone during the day once in a while for some hours to do my own thing. I wanted to challenge myself again, and wear heels. This time I decided to go to a coffee shop and grab a drink & some food, and work. So I did just that, picked a coffee shop that was far enough away from home, packed myself into the car, and went. This time I was quite self conscious in my brown wedge ankle boots, and long jeans covering most of it. While standing it was OK, the heels weren't showing, but when sitting I'm sure they were. I tried it out before going to the coffee shop and the jeans would ride up if I sat down, so I assume people could see some of it. But I sat down, enjoyed my drink, ate a bit, and worked on my laptop. Spent about an hour there. Got to repeat this 3, maybe 4 times over the course a few weeks. Quite enjoyable, but doesn't beat the above two adventures. Cloths: Varied, but long blue jeans with 3" wedge ankle boots covering most of it. --------------- The above outings might show progress, and they are huge progress compared to what I was doing a year ago, or further back. But I am still very much conflicted with this heeling thing, and I am sure these emotions will not go away for a while yet. I am trying to challenge myself, and in the process wear my heels, and so far so good. I am still very uncomfortable showing photos or URLs of the heels, or myself. I love it when others post photos of themselves in coffeeshops, etc, but I am not comfortable with that, for various reasons.
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