heelguy's adventures

[partyshoes]

Hey Heelguy, thanks for sharing. Its a fantastic story and very inspiring - now need to to get it out of my head Anyway, love the shoes, great shape on toe box - like a roundish toe myself and love the height. Please keep the stories coming

[danielp6406]

Greetings heelguy :-)

Nice shoes and shopping with a good female friend who is also open minded...

You cannot ask for anything more isnt-it ?

Well done !

[heelguy]

Thanks everyone yea it was amazing. I was pretty hesitant and in two minds wether to open up to her about my heel wearing. To open it up i sent her a message informing her that there was a pair of shoes i wanted to try on and possibly buy. I didn't state anything about the shoes as to not make a big thing of it. Once i'd sent the message i thought well i can either do two things now.. i can go ahead and just get the heels which i really want to do, OR i can either lie and try a different pair of shoes or just not try any at all. But as we were shopping around i saw the store coming up and thought to myself "I actually really want these shoes, whats the worst that could happen?" so just went ahead with it like nothing was out of the ordinary and it all worked fine. She think's it's cool and call's my heel wearing my "hobby" which i like and think is a good way to describe it. I also (although not as passionately) like to look out for and wear high top nike's. I consider this as a hobby, almost like a collector. So the terminology fitted for me it's great to have somebody you can share your heels with, and like i said before, i recommend it to anybody who's thinking about opening up to someone, like the nike tagline says.. JUST DO IT! haha

[jay jay]

Thanks. My fiance also go out with me and we buy shoes together ( we wear the same size SA 8 or a 41) I have not yet tried on a pair in the shops but the time will come.

[zebra heels]

thats great heelguy. did you show her your collection? PS love the heels

[heelguy]

Thanks Zebra, oh i must have forgotten to mention that! Yes! i did! we came back to my house to hang out for abit and i got out ALL of my heels, we both tried them on (she is one size smaller than me, so thought that some may fit her, but none did :[ ) as i pulled out my grey heels she said "ooo those are my favourite!" then i pulled out my snakeskin tony bianco's and she then changed her mind saying "actually no, these are now my favourite!" She's not much of a high heel wearer herself, but im sure i can change

[zebra heels]

Heelguy that is great. Isnt great when you can have a heel party lol. Thats what my friend and I call them. Speaking of a heel party i need one asap:smile:. Too Bad we are on different sides of the world because we would have alot of funny heel shopping and what not

[heelguy]

Long time no post! So here's abit of an update.. It'd been quite a boring few months with nothing really happening in my world regarding heels. I could feel the itch SO SO badly and needed something new to happen. I have a male friend with who i am also good friends with his girlfriend. I'd always considered telling her about my liking for high heels and other female attire but was always abit scared to tell her as obviously she's only one conversation away from my whole friendship group. I was chatting to her one night trying to cheer her up and take her mind off some things but nothing was working, so i saw this as a perfect opportunity to really give her something to think about I told her all about my interests in this subject. She recieved it very well although almost refused to believe me before seeing it in the flesh as she said there is no way in the world she would ever pick it out! So a few nights later we arranged to go and get coffee together and i said i would wear my heels. Turns out that when i went to pick her up, she had a friend with her! so now her friend also knows too, but it turned out to be a short but pleasant evening all 3 of us out having coffee together all wearing heels As most of you who have read my previous stories would know, my girlfriend is aware of my high heel wearing. Well she was still unaware about the fact that it didn't just stop at high heels i'd been telling her for a while that there was more i needed to tell her, and she'd said to me that she thinks she knows, she'd just rather not hear it just yet, because she wasn't sure she'd be comfortable with it and give me a good reaction, so i held off. Anyway one night we were talking like we do every night as we live in seperate states, she asked what i was wearing and i told her "you'd rather not know if you get my drift..." to which she said "ohhh, well... i think you should tell me :)". I was nervous as hell even though she practically already knew. I told her all about what else i enjoy wearing and her reaction was fine, she told me that yes, she had assumed that it went further than just high heels and i'm now completely open with her about everything i wear We're seeing each other again in february and we're going to go out and have a day getting pedi's, go shopping and have coffee and lunch in our heels together, i can't wait! i'll be sure to update you all on that! I also have a female friend who i've stayed in contact with that i met in my previous work who knows about the way i dress too but had never seen it, one night she called and asked me if there was any chance i could pick her and her friend up from a party they'd been at, so i said of course! i put on my heels and a high waisted skirt and went to pick them both up. Turns out her friend is the same size shoe as me so we're soooo going to borrow each others shoes! haha Anyway... this same female friend called me again the other night asking for a lift very apologetically at 4am in the morning as she needed to be home but had no way of getting there at all. I was glad she called as id rather her wake me and i get her home safe than her being stuck somewhere she didn't want to be. I put on a short, tight front button sailor dress which i got from a store over here called "supre", my grey high heels and picked her up and took her home. Nothing was said about my attire at all, it was like nothing was out of the ordinary which was actually quite dissapointing, but she'd been round to my house between these two occasions and i showed her everything then, so what can i expect? On my way home from dropping her off at her house, it was now about 5.30am, i'd NEVER been outside in public in a dress/skirt before so i decided to stop at the servo to get petrol even though i didn't need to. Before now all i'd worn out in public was high heels and skinny jeans, so this was a first time for me, and the dress i was wearing was my shortest and tightest one i own! As i stepped out of the car i could feel the crisp morning air on my legs, it was an excitement i hadn't felt in such a long time! There was a small truck also in the servo with the driver filling it up too but he didnt pay me any attention. I walked in to pay for my petrol and the counter was very low with quite a distance to walk to from the door so the cashier could clearly see from top to bottom whatever his customers were wearing. I was greeted with a smile and hello just like normal, as i walked back out of the store i used the glass to see if he was looking at me as i walked out, he couldn't keep his eyes off my legs! haha it was a huge thrill, not half as scary as i'd imagined hope you all enjoyed reading! im hoping to get out more in my heels and skirts/dresses, they make wearing heels much more fun!

[heelguy]

I often spend hours browsing ebay looking out for anything that catches my eye, 99% of the time it's all crap or priced too high. But the other night i came across a pair of heels that i've wanted since i saw my girlfriend in her's almost a year ago! I messaged the seller right away asking for a buy it now price but to my dissapointment they declined to stop the auction for a set price. Never the less i felt optimistic and i thought i'd try my luck and i messaged them once again offering my price and i'd pay on pick-up of the item. I got a reply today with the seller accepting my offer. I called the seller as she provided me with her phone number to arrange pick-up which was only half an hour away from me. Earlier tonight i drove there and picked them up, im SO happy i finally got my hands on my very own pair of these after falling in love with them the moment i saw them on my girlfriend's feet! Hope you all like them as much as i do...

[skirtedvik]

Nice dress and heels,but it wouldn't be me if i do not say - where is the front part, mate?Keep up freestyling!

[Cl0setheels]

I often spend hours browsing ebay looking out for anything that catches my eye, 99% of the time it's all crap or priced too high. But the other night i came across a pair of heels that i've wanted since i saw my girlfriend in her's almost a year ago! I messaged the seller right away asking for a buy it now price but to my dissapointment they declined to stop the auction for a set price. Never the less i felt optimistic and i thought i'd try my luck and i messaged them once again offering my price and i'd pay on pick-up of the item. I got a reply today with the seller accepting my offer. I called the seller as she provided me with her phone number to arrange pick-up which was only half an hour away from me. Earlier tonight i drove there and picked them up, im SO happy i finally got my hands on my very own pair of these after falling in love with them the moment i saw them on my girlfriend's feet! Hope you all like them as much as i do...

You have such a great taste in heels. I love those!

[heelguy]

Nice dress and heels,but it wouldn't be me if i do not say - where is the front part, mate?Keep up freestyling!

Hi skirtedvik, even though i am wearing a dress in a couple of the pictures, the shots were more so to show what the heels looked like with an outfit i'd be likely to wear them with So there's less emphasis on the dress, more on the shoes

You have such a great taste in heels. I love those!

Thankyou imroter! I love them too!

[SleekHeels]

Great find heelguy, the year to track them down was well worth the wait, they look really go on you. Have you stopped gazing down at them yet? Awesome adventures too, heels and coffee with the girls sounds like heaven!

[1234tazzer]

Great out fit with I was 20 again. But I did realy like the heels and the out fit was awsome. Thank you for the post.

[heelguy]

Great find heelguy, the year to track them down was well worth the wait, they look really go on you. Have you stopped gazing down at them yet?

Awesome adventures too, heels and coffee with the girls sounds like heaven!

It definately was! thankyou, i haven't had much chance to wear them as i only got them last night and i had work early today, but on my way home last night from picking them up i did stop off at a servo (gas station for any american's reading this) and i already had them on because i couldn't wait until i got home to try them! i walked across the forecourt and there were two other cars filling up with petrol. It didn't phase me one bit and infact as i walked into the store the male clerk greeted me with a smile and was quite talkative with me throughout my purchase!

Heels and coffee with the girls is AMAZING! i love us all strutting our stuff in our heels down the street lol i can't wait to wear this outfit when i go out next!

[muddypaws]

I sure hope your gf likes them as much as you do. If that is your body in them, when can we have a date. They are great. Pass them on to me when you are finished with them. Muddypaws.

[hhboots]

Great out fit wish I was 20 again. But I did realy like the heels and the out fit was awsome. Thank you for the post.

I'm with you on that one. I wish this site was around when I was 20 and that I was having as much fun with street heeling at heelguy's age as he seems to be having. Ahh well. better late then never I guess, I'm having fun in heels now, but definitely would have really loved to be doing this back then.

Anyway, very nice shoes once again there heelguy.

[Awtucs]

Great heels, and dress of course! I do recognize the eBay addiction, and sometimes also looking out for the same footwear my wife has (possibly for models in our sizes, Eu 36 and 43, respectively I'm truly happy for your success in finding what you've wanted for a long time, and wish you all luck in continuing the high heels and dress success!

[denisegurl2]

I often spend hours browsing ebay looking out for anything that catches my eye, 99% of the time it's all crap or priced too high. But the other night i came across a pair of heels that i've wanted since i saw my girlfriend in her's almost a year ago! I messaged the seller right away asking for a buy it now price but to my dissapointment they declined to stop the auction for a set price. Never the less i felt optimistic and i thought i'd try my luck and i messaged them once again offering my price and i'd pay on pick-up of the item. I got a reply today with the seller accepting my offer. I called the seller as she provided me with her phone number to arrange pick-up which was only half an hour away from me. Earlier tonight i drove there and picked them up, im SO happy i finally got my hands on my very own pair of these after falling in love with them the moment i saw them on my girlfriend's feet! Hope you all like them as much as i do...

Sexy shoes and I luv that dress! Thanks for sharing

[heelguy]

Thankyou everyone for your kind words and replies I realised after looking through photo's on my phone that i completely forgot to update you all on another pair of shoes i recently purchased! woops! Anyway.. One day after work i went to a local shopping center, i was headed for a certain store i wanted to get a few things from.. as i walked in a could see some new construction going on inside the building but thought nothing of it and carried on. As i got right up to where i remember the store being, i was struck with dissapointment because ALL of the store's in that section were boarded up and being renovated, including the one i headed there for in the first place! never the less it was still early even though i had been at work that day so i decided to visit another one of their store's. I arrived at the other shopping center and walked in, online the store said it was a sectioned part of another store which seemed strange to me as it's a BIG store here in Aus that i was looking for. I found the one it said online that it was but couldn't find this so called section that stocked the certain brand i was after, so i asked one of the sales assistants (an older lady who seemed much more interested in folding clothes than helping me) pointed me to a tiny rack with hardly anything on it. By this point i'd started to lose hope of finding what i was looking for. I remembered that one of the girls i got chatty with at a payless store in another center a little distance away from me had told me she recently started a new position with the same company at another shopping center which was closer to me but i hadn't yet been to visit her, nore had i ever been to the center in which she now works, so decided to cut my losses and go see her! She works at payless shoes so i knew there'd be lots of shoes for me to try on even though i wasn't out to buy shoes that day. Once again i headed off to yet ANOTHER shopping center and wasn't even sure if my friend was working that day, but as id never been there before, i thought even if she isn't working, i can still have a look around and see what it's like. To my delight when i got there she was working and seemed very pleased to see me we got chatting and catching up on each other's lives, as we were talking i decided to try on some shoes i'd seen that i liked while i was there. I must have tried on about 7 or 8 pairs of shoes with her helping me with them while we chatted, it was fantastic! But i couldn't decide between two pairs There were other customers entering the store and maybe only an hour left before the shops started to close so i left her to start wrapping things up with her store as she's the manager there, Before i left i asked her if this certain store i'd been after all day was in the center, she told me there was and that it was just around the corner! So off i went.. On my way to the store i saw another store called Supre which i always like to have a look in. They sell all female clothes, i'd say their average customer is aged between 16 - 25, so needless to say, there's some revealing stuff in there! i wasn't sure on time so i skipped Supre for now to head straight for the main place i wanted to go to, YAY! i'd finally found it, i spent about 15/20mins in there and got a few things that i was after, so decided to head into Supre after all and have a look around. I was greeted by a nice young lady and asked if i needed any help, i declined and told her i was 'just looking around, but thankyou!'. I found a little white completely lace dress that i liked, so i asked her if she could show me if they had a slip that goes underneath it, she asked the size i was looking for and pulled one out for me. I usually find the service at Supre sub-standard when they're dealing with a guy like me as they wonder what the hell i'm doing in that kind of store, but as the girls in here were very nice just like they would be to anybody else, i decided to buy them! There was now only about 15mins of shopping time left before it closed, and on my way out i had to pass my friend at payless again anyway, i felt kinda bad for taking up her time and not buying anything, and i really did like these two pairs of shoes. So i quickly went back in and tried them both on again, it was between a pair of black peeptoe wedges or wooden heel lace up's. I was going to buy both but decided not to as i'd spent more than intended in two stores already! and as the wooden heels were abit more different to any other shoes i already have, i went for those, i bought them and walked out feeling better about not wasting her time with chit chat and trying on shoes plus who of us here doesn't enjoy a new pair of heels even if they're not needed? haha here's a couple of pics of the heels in question

[ilikekicks]

Those are hot!

[heelguy]

Thanks ilikekicks! They're different to the usual shoes i'd go for.. i think that's why i like them they're comfortable to wear too which is always a bonus!

[ilikekicks]

From the picture title ( payless.jpg ), we have payless stores in my area of New York. I havent seen anything like those at those stores here.

[CPB]

I'm not a great fan of peep toes, but the previous set of photo's are absolutely gorgeous!! Definitely worth the long search & wait.

[heelguy]

Lately i've been considering broadening my options with regards to my high heels and the way i like to dress. Over and over in my head i've been wondering how it would pan-out if i "came out" about my love for womens fashion, wether it would wittle out the people in my life that i dont really need there and the people that stick around and show me they're true friends and love me for who i am, not what i wear. I've also been considering how it would affect my home life with my parents finding out and all.. But there have been numerous conversations with them when i've been present and they've started talking about transvestite's and crossdressing, all of which have ended positively with either one of them saying that there's nothing wrong with it and actually understanding that you don't HAVE to be gay to enjoy it. Whilst i am a wearer of women's clothes, i dont consider myself a CD, as i feel like the fashion fits me and who i am, rather than being assigned to a specific gender. Well with this floating on my mind i discussed it with my girlfriend and how she feels it would affect her if everybody found out about the way i am. She said to me that really, it doesn't matter how it affects her because she knows how good it would be for me, but i can't help holding back a little to save her any embarrasement she may feel (or maybe im just making excuses for not being out with the truth!). Anyway, i've felt long overdue for another heeling adventure, and planned to go out with a couple of girlfriends to a club in the city called "Priscilla's @ 153" in Melbourne. They hold drag nights on a friday and saturday nights, entry is free and i have a male friend who goes there often during the week who recommended it. Well... with this planned, it begs for a new outfit to strut my stuff in! So after work last thursday, i headed to Chadstone Shopping Centre here in Melbourne to get myself one! I went into a shop called "Supre", which isn't a shop of the highest quality garments, and they're target customer is usually 14-18yo females with little taste. I see this as a stepping stone for young females and a place to start exploring their inner fashionista, so what better place for me to start? I went in knowing pretty much what i wanted, but when i was approached by a young female sales assistant and asked her for the specific items i wanted, she informed me that they no longer had them and that they were only online :/ bummer! I carried on looking and found myself a few things and took them over to the counter to pay. The young SA who previously helped me was there to serve me and asked "what are they for? :)" I froze for a second and considered my options.... 1. i tell her they're a gift and she's none the wiser or 2. i be honest with her and hope for the best. Well me being my awkward self, out of knowhere i replied "what do you mean?" to which she gave me a strange look.. I then said to her "you wouldn't believe me if i told you anyway" and she said "ahh i dunno, we see all sorts in here! so what are they for then?" i told her they were for me and that i was going out with a few girlfriend's on the weekend and told her all about the place we intended to go to blah blah blah she wished me a good time and off i went to continue my shopping. Okay so i'd already gotten my outfit, plus another dress that caught my eye, so that was my spending done for the day (or so i thought). I just wanted to check out the shoe stores to see if they had any ankle booties that i'd fall in love with because i already tried on a pair with my girlfriend but they were $170 and i wasn't super keen to fork that much out for them. My first stop was a store called "Santini" and to my suprise they had a simple pair of ankle booties with a short side zipper for decoration. Now, this store's SA's aren't the friendliest looking bunch of girls i've ever come across. In actual fact to be honest, they look like straight up bitches, lot's of make-up, super expensive clothing, tackily well groomed. Never-the-less these booties were $80, so i wasn't going to pass up the opportunity to try them on as they were so well priced! i asked the one young woman if she had them in a 9 but she came from the back and told me they only had a size 8 or 10 and then asked me "are they a gift?" i said to her without hesitation "no, they're for me :)". Expecting to be looked at like a weirdo and frowned upon, she then said "ooo very nice , did you want to try them on?" so she went and got me the size 10. I tried them and they were a little big, but i wanted them and being ankle booties they didn't slip off my foot. After having 2 very pleasant and quite unexpected experiences at both stores, i left the shopping centre feeling very happy about the whole thing. Unfortunately, me and my girlfriends were meant to go to that club tonight, but we didn't end up going so the outfit's will have to wait for another night! Here's a couple of pics anyway, i originally intended to wear the first outfit, but after trying the blazer with the second outfit, i've decided to wear that instead hope you like!

[SleekHeels]

It's very honest of you to admit that your preconceptions about the sales assistants turned out to be wrong, a reminder that we can still catch ourselves pre-judging people by their appearance. It's great that they were so cool about the boots, which are very cute by the way - they could work well with so many different looks, maybe skinny-jeans with your black jacket or a long-line cardigan now that the Melbourne winter is approaching.

[heelguy]

It's very honest of you to admit that your preconceptions about the sales assistants turned out to be wrong, a reminder that we can still catch ourselves pre-judging people by their appearance. It's great that they were so cool about the boots, which are very cute by the way - they could work well with so many different looks, maybe skinny-jeans with your black jacket or a long-line cardigan now that the Melbourne winter is approaching.

It is so true, no matter how hard we try i think we all are a little bit judgemental. It really made me realise that what i was doing to them by judging them on appearance was exactly what i didn't want happening to me, which made me feel bad, but at the same time it felt good because it was like my preconseived assumptions of that type of person were completely thrown out of the window

Thanks SleekHeels, glad you like them! that is very true, they work well with lots of things, i recently got myself a pair of "sass and bide - black rats leggings" (check them out on google) which i think will go great with the boots! i think the winter has already hit! it's been freezing cold here lately! lol

[jarod81]

I like you I also have a love for women's fashion and feel that it is mystyle. Last year I decided to start coming out more and telling my family. Both of my parents now know what I prefer to wear and have no problems with it. Along with a handful of my closest friends everyone has been very supportive of my choice. The only regreat I have is that it took to long for me to accept myself and to be comfortable with myself. If you feel that this is what you want then go for it and enjoy you life. You will unfortunately loose some friends who don't understand but you will gain new ones who do.

[ilovetights]

Whilst i am a wearer of women's clothes, i dont consider myself a CD, as i feel like the fashion fits me and who i am, rather than being assigned to a specific gender.

I've never liked the term crossdresser because it has so many negative connotations but even more so because I have never felt like I am doing anything wrong (I know I'm not!!). These are the most thruthful words I have ever read regarding wearing women's clothes (and I thank heelguy for it). I feel exactly the same way.

Heelguy, why didn't you tell me you were going to Chaddy??!!

I have been wanting to buy a skirt from Forever New so badly but have been working quite a lot and have had a few other (more important) things going on too so have held off to this time.

I remember one day (years ago now) I went around Chadstone looking for skinny jeans and asking shoe stores the largest size they offer and I got far more positive, friendly and helpful SA's then negative ones. Ever since I've had no problems shopping around Chadstone. (If anyone comes down to Melbourne they should definitely check this shopping centre out... it is pretty big and has so many great shops! It's slogan is "The Fashion Capital").

Love your description of supre!!! ....Good to hear of your adventures and new purchases, heelguy. You're looking great (if you don't mind me saying)... you must have quite a collection of heels and clothes now?!!

I love the shoes at Santini, most of all in summer! There are always great heels there and most with platforms! I hope you didn't pay too much for the S&B Rats... I've bought 2 pairs of Rats for $10 each (rrp $170+ for those who are not familiar) from their warehouse sales!! As a result, I wouldn't pay more than $50 for any rats.

[heelguy]

I've never liked the term crossdresser because it has so many negative connotations but even more so because I have never felt like I am doing anything wrong (I know I'm not!!). These are the most thruthful words I have ever read regarding wearing women's clothes (and I thank heelguy for it). I feel exactly the same way.

Heelguy, why didn't you tell me you were going to Chaddy??!!

I have been wanting to buy a skirt from Forever New so badly but have been working quite a lot and have had a few other (more important) things going on too so have held off to this time.

I remember one day (years ago now) I went around Chadstone looking for skinny jeans and asking shoe stores the largest size they offer and I got far more positive, friendly and helpful SA's then negative ones. Ever since I've had no problems shopping around Chadstone. (If anyone comes down to Melbourne they should definitely check this shopping centre out... it is pretty big and has so many great shops! It's slogan is "The Fashion Capital").

Love your description of supre!!! ....Good to hear of your adventures and new purchases, heelguy. You're looking great (if you don't mind me saying)... you must have quite a collection of heels and clothes now?!!

I love the shoes at Santini, most of all in summer! There are always great heels there and most with platforms! I hope you didn't pay too much for the S&B Rats... I've bought 2 pairs of Rats for $10 each (rrp $170+ for those who are not familiar) from their warehouse sales!! As a result, I wouldn't pay more than $50 for any rats.

Hi ilovetights, thanks for your response. Although i dont consider myself a CD, i don't see that there is anything wrong with it.

There's always time to go shopping! especially with chaddy open until 9pm on thursdays and fridays! Your other priorities must be pretty important to put shopping aside!

I was always fearful of going about my business in chadstone as it's such a large and commercial shopping center, i preffered the quieter ones (ie waverely gardens ) but now i've had positive experiences at chaddy, i'll definately be going there more often to shop my little heart out!

I don't mind at all, thankyou for the compliment i also showed my GF these pictures and she said i look good too, so that made me extremely happy!

I do have quite a few pairs of heels now (12/13 off the top of my head i think) but not too many clothes, i think i have around 5 or so dresses, a couple of skirts, jeans etc.. enough to keep me going for odd night out on the weekend anyway! there's 20 years of being a traditional socially normal boy to make up for! haha

i paid $40 for my black rats, although i noticed one of the girls in santini wearing a pair and hers were nowhere near as shiny as mine :S mine have all the genuine tags and labels attatched, but i cant help wondering wether they're fakes or wether Sass and Bide brought out different shades of them?