Ben094

I just went out for another little stroll, around 11:30pm here.

As usual there was that nagging yet exciting 'wait-by-the-door-and-pick-your-moment' feeling, but I just thought screw it (excuse the unpleasantries) and went.

I was wearing my latest pickups over my jeans for the first time and it was a lovely feeling. I was also wearing a black leather jacket with a hood on, but by the time I was halfway around my walk I just took it down. The confidence boost I'd got from overcoming the hesitation earlier had given me quite the sense of freedom and empowerment, and I felt like I didn't have a care in the world. By the time I'd got back around to my street I saw a rather young lady a couple doors up having a cigarette outside.

Still with my confidence boost before, and especially after I saw her glancing over, obviously curious at the sound of my heels on the pavement (which is a lovely sound, I think we'd all admit), I decided to make conversation with her. A fence separated us both so, as politely and cautiously as possible so late at night, I called over to her: "Excuse me?", to which she replied: "Yeah?", "I was just wondering if I could have your advice on something?". "Sure," she replied kindly. "Come through the gate, I can't see you up there" she humoured.

As I walked through her gate, with my hood down, she kept eye-contact with me and glanced down at my boots that were shining in her porch light. She looked back up after and didn't seem to be phased by it. I smiled at her and asked: "From a ladies point of view, can I ask about my boots?" she looked at them and smiled again. "They're quite new and I'm trying them out. They're really comfortable and nice to walk in, but I was just curious as to what you thought of them?" at this point I was rather nervous to be talking to a complete stranger about something so personal and nerveracking, but she was really nice about it.

"I think they look quite nice, actually, and especially with your jeans." she hesitated, questioning me with her eyes. "Go on then, let's see how you walk in them." she requested, to which I was quite taken aback by. I hesitated a little, but I walked up her driveway with great confidence and back down again to where she was standing. "How long have you been wearing heels? You walk really well in them for a guy; most struggle and their balance is all wrong.", to which I replied: "Since I was quite young, just curious, but up until recently probably about a year or so, mostly in my house down the street.". She nodded, interested. "I think you should wear them outside more. You look pretty confident in them and if you like them, wear them." she suggested.

I was really touched by what she'd said about my boots and the way I walked, especially considering she was just a stranger, and offering me advice like that really made me feel chuffed inside and actually brought a little tear to my eye. She took one last drag of her cigarette and dropped it between us. She smiled at me and asked: "Can I ask something?", "Of course,", I replied, "Anything.". She looked down at the cigarette she'd dropped and winked at me. Out of some strange instinct, I put my right boot over it and turned it left and right a few times, putting it out for her. She smiled again and laughed a little before wishing me goodnight. I replied with the same and thanked her very much, then walked back home.

A phenomenal experience, I have to say. To think that a complete stranger had given me such kind feedback and implored me to go out in public more often with my new boots was lovely, and I will most definitely be taking her advice. I'm already thinking about my next venture as I type this and the smile has yet to leave my face. I just thought I'd share this little experience with you as a few of the posts in this thread are along the same lines of feeling conscious or discussing our first few times.

All the best,

Ben

SleekHeels' first experience is eerily reminiscent of my own, and reading it almost felt as if somebody had watched me the entire time and documented my own experience for me.

I did it late at night also, around midnight. My area is very quiet and next to nobody is awake at that hour. Your heart is pounding for two reasons I think; one because there's that underlying worry that somebody will see you and make fun of you (which nobody wants, even with the thickest of skins), and because it's something you've built up the courage to do for so long and you're finally taking those first steps. It's a huge adrenaline rush really, and I significantly remember having a few nervous yet excited sweat drops on my forehead while I had my little walk.

I too felt the strain on the bottoms of my feet, but that's because, like SleekHeels eluded to, you kind of rush yourself. You have that worried feeling inside but the excitement keeps you going. I know when I took those first few steps I was very conscious but you start to develop a more confident approach to wearing your heels/boots in public, even if my experience was at the dead of night. It becomes more of a natural feeling to you and the confidence exudes out of you. Once you've had your first experience and you've had time to dwell on what you've just done, you want to do it again and again. It's a very addicting feeling; similar to people who have tattoos (myself included).

You very rarely just have the one.

I must say, I'm really pleased to see such a friendly and sharing community here. This isn't the first forum I've been a part of in relation to guys wearing heels and I won't name names but this is by far the most friendliest and I feel very comfortable opening up to you all, even as a newbie here. Here's hoping I get to stick around a lot longer and share more stories like this with you all and generally have nice chit-chats.

Ben

These are my latest pick-up.

Legroom brand, black knee high boots, with a 5cm heel, size 9E.

I wanted something casual but trendy at the same time and I really loved the look of these. I think they look great under or over some dark blue stonewashed jeans. By far the nicest fittings boots I own, also. The leather is buttery soft and feels worn in despite being brand new, and they're incredibly nice to walk in and they feel as if they have no heel at all while still giving you that uplifting sense of extra height and empowerment from wearing a pair of boots. Thinking of going to meet a friend for some coffee soon and try them out properly. At £20 on eBay you can't complain, really.

Thanks everyone for opinions and support. I get that heels need to match with the right outfit. I have been looking at a few gallery's to get some ideas. I have been looking. One problem my wife doesnt support me and she pays the bills. Its hard to spend money on women's jeans or clothes without hee knowing bout them. There have been a few pair of jeans I have wanted. I am crazy bout heels and leggings. I have been wearing leggings and they look great on me. I have yet to build confidence to go to a women dept store with leggings and heels to see what looks good on me.

Confidence is by far the biggest step for most people, myself included.

As comfortable as I am walking around in my heels at home, as well as not caring if the neighbours notice me, it's still a huge challenge to just throw on a pair of heels and go out.

I've only ever done it once and I was actually complimented by a lady passing by saying my boots looked great on me, but even with that one compliment, it's still nerve-racking. I too hate how society has deemed that guys wearing heels is some form of mortal sin. Most people forget that heels were originally designed for wealthy men. One way I look at it is that mens fashion is totally boring! Always the same stuff just in different colours. Female fashion is always changing, and more often than not, men have better taste than some women.

Hi, everybody.

Firstly, sorry for the delayed introduction. Secondly, I suppose I'd better introduce myself properly!

I'm an average guy of 20, working as a freelance artist. Like most guys on here, it will have started from an early(ish) age, but I've always loved the look of heels; though preferably boots.

The first pair I bought myself were thigh-high PVC stiletto boots. They looked really nice and felt great for a little while, but were prone to calf cramping because of the height (13cm).

Currently, I own three pairs of boots. Some 6cm black calf boots, great for wearing under trousers or jeans, a pair of knee-high black platform boots that are for more special ocassions than anything else, and my most recent pair which just a casual pair of black knee high boots, about a 4cm heel, slightly square-toed and look great either under or over jeans. They're by far my most comfortable pair and feel great to walk in; almost as if they're flats.

Anyway, that's my short story.

Nice to meet you all!