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High Heeled Vacation planning


heelguypa

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Well finally found a girl that loves and not only supports but encourages me to wear high heels. And best of all we wear exactly the same size so I can wear her extensive collection of shoes.

We want to go out in heels however we are from Panama and this is not the most accommodating and tolerant society for thing that are different form the norm. As well as it is a small city, there is nowhere we go at any time that we don’t with someone either of us knows.

So, doing it here is out of the question. We have done it but very very discretely but not the way we wanted, for instance once we went out really late around 3 am for “dinner” at a dinner that is open 24 hours, at that time usually drunk people are in but I just wore wedge sneakers hiding the heel. Another time we rode our bikes wearing 4-inch stiletto almond toe booties late at night and no stops.

But I digress, we want to enjoy full time high heel wearing.

Our plan is around April to fly over to San Francisco, we chose it because it seems to be a very open-minded community and city. And April so it is not too hot nor cold.

The idea is that as soon as we land and until we are back at the airport going back home, during those 2 weeks all my footwear would be chosen by her and she told me that I will be in highs heels 24/7, trying for most of the time to be in stilettos. Not opposed to that, actually looking forward to it.

We have a few items in our bucket list for the trip:

-        -   As I said I would be in high heels 24/7

-        -  Go out for a fancy dinner she wearing a black cocktail dress and me a sharp pinstripe suit with a tie and black stilettos

-        - The same as before but wearing pink or very girly and flashy high heel stilettos.

-        -  During the day walk around, shop, get to know the city, visit land marks wearing high heels and carrying comfortable wedges if it gets tiresome but always on high heels

-        - At night go out to different places bars all in high heels and casual clothes

-         - Sometimes go out in matching shoes

-         - Shoe shopping and trying it at the store and walking out wearing them.

-         - Purchase matching designer high heels, we both are in love and want 12CM heels Pigalle shoes from Louboutin. But still open to alternatives.

That list I our must do.

Well that is our dream adventure and plans, I am posting here from a very long absence (my previous account is lost). We want to know your thoughts, ideas, recommendations, critiques, anything you can think of. We could change location if you suggest a better one and we like it. Suggest activities, places to visit, places to avoid, bars, restaurants… Suggest some more goals for the list. All and any ideas are welcome.

Thanks a lot and thanks for all the people ins this forum it makes it so much easier and more to do something I love knowing I am not the only one.

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My first major public outing in high heeled sandals was in San Francisco. My avatar photo was taken there. Aerosoles "Platonic" sandals, which I have in black and brown and still love wearing them - t-straps with about 3.5" heels. 

Watch out for the steep hills in San Francisco. Going up in heels is easy, but coming down is treacherous and difficult. You might want lower heels for that!

Hint: Don't go to vacant and abandoned places late at night. You may be spotted by somebody unexpectedly and if they see you're wearing odd footwear, you could be facing the police for questioning. Instead, go to busy places in the daytime, such as malls and shopping areas. People are too wrapped up in their own affairs to notice or care what you are wearing, and if it's broad daylight, no one will be suspicious of illegal activity. 

Good luck in SF! Keep reporting your progress!

Steve

Aerosoles Platonic black in SF 1 close-up.JPG

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Thank you Steve, good advice and good to know.

We plan to go to public places all the time it is the whole idea of the trip being in public wearing high heels, the more people the better.

As per heel height I will let her know what you said, but as I said shoe choice during this trip is entirely up to her. I have no say whatsoever.

The only say I have in shoes during this trip is the choice of the matching Designer heels we want to purchase, that is a mutually agreed decision, the ones we want right now or if we see something else we like.

I will keep you guys updated from the moment we purchase the tickets.

 

 

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Hi

I wear heels all the time. I have for a decade. When I started wearing heels a lot - say 15 years ago now it took me a very long time (2 years say) to become good enough to wear tall stilettos all day. Most guys have less flexibility in our feet than women so it is harder for us to start with, that and it is seriously many many times harder wearing heels all day and in all situations.

I do not want to ruin your fun - but I would seriously advise you to be careful of what you wish for here - its a pretty big ask if you want to do a lot of walking around a city and its attractions in tall stilettos. I am all for challenges and having fun and doing stuff - I honestly wouldn't aim to to wear my average to taller heels all day for 2 weeks while going around a new city - and I wear heels all the time - I know it would be really hard work for me to do.

My advice is plan to mix your heels up, and take varied stiletto heights deliberately. Then if you're keen you can dial the heels up all the time, rather than being limited to wedge back-up options you mentioned because you got heeled-out. That way you've got your favourite heel options in varied heights and the enjoyment can be maximised ?

 

On a more positive note - Shoe shopping sounds so cool together!!!  Get a pair of matching So Kates - I reckon they're the best CL. Pigalle is too small in the toe, and the heel feels awkward underfoot in the pigalle.

Are you going to fly there and back in heels. Its fun flying in heels - always get lots of compliments from the air crew. You should try that?

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I live close to SF and have been around there in my heels. This city is not very stiletto friendly other than the financial district and SOMA (south of mission avenue). San Francisco is built on hills and many of the tourist things are not heel friendly. It very easy going UP, coming back DOWN and be ver difficult.

Chinatown...on a hill.

Fisherman's wharf/waterfront. uneven planks with gaps between planks, uneven surfaces....

Ghirardelli Square hill..

Lombard Street is a steep hill...that's why all the twist.

Jumping on and off street cars...extremely easy way to break a heel.

Better place for the heel-cation you want would be someplace flat, like NYC.

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heelguypa,

Welcome to our site!  Read your post about wanting a trip to San Francisco. I once lived there and can offer you some useful information. As Cali pointed out SF is built on a series of hills. The fact is, for a city on a peninsula with the ocean virtually visible from many areas, most of the city is better than 200 feet above the water. Many streets have grades of 11% or better which is rare in North American cities north of Mexico. While SF doesn't care what style you wearing YOU may want to choose your style carefully. I would take at least two pairs of wedge sandals which give you height but with stability. You could plan a night out to dinner and then a nightclub in stiletto heels but pack them in handbag and change into them as you arrive at your venue. That way you'll avoid the hazards described above. My other advice is this: San Francisco is one of the coldest cities you never saw coming! The average high temperature in the warmest month (September) is just 70F/21C. The driest months are May-September although there is abundant sunshine all year around. Despite low average rainfall the humidity is almost always high in SF as there is water everywhere you look. The average high in April is 63 which is the same in November. Its climate is not typical of anywhere else in the USA. It is a Mediterranean climate with a heavy marine influence. A jacket is about the most important possession a San Franciscan has. If you want specific ideas on where to stay I'll give you some.  HappyinHeels

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Welcome back!

I agree with the others - high wedges are a safer bet, both for the topography and your current "skillset". High wedges can also be very sexy - so no need to worry about that. See if your GF will agree to that (so lovely, btw that you have each other!)

 

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4 hours ago, HappyinHeels said:

heelguypa,

Welcome to our site!  Read your post about wanting a trip to San Francisco. I once lived there and can offer you some useful information. As Cali pointed out SF is built on a series of hills. The fact is, for a city on a peninsula with the ocean virtually visible from many areas, most of the city is better than 200 feet above the water. Many streets have grades of 11% or better which is rare in North American cities north of Mexico. While SF doesn't care what style you wearing YOU may want to choose your style carefully. I would take at least two pairs of wedge sandals which give you height but with stability. You could plan a night out to dinner and then a nightclub in stiletto heels but pack them in handbag and change into them as you arrive at your venue. That way you'll avoid the hazards described above. My other advice is this: San Francisco is one of the coldest cities you never saw coming! The average high temperature in the warmest month (September) is just 70F/21C. The driest months are May-September although there is abundant sunshine all year around. Despite low average rainfall the humidity is almost always high in SF as there is water everywhere you look. The average high in April is 63 which is the same in November. Its climate is not typical of anywhere else in the USA. It is a Mediterranean climate with a heavy marine influence. A jacket is about the most important possession a San Franciscan has. If you want specific ideas on where to stay I'll give you some.  HappyinHeels

I went to SF once and was amazed by the temperature, especially as in the Sierra Nevada (several thousand feet up) it was warmer! It was May, and I very definitely needed a jacket although it was a lovely sunny day. Lombard Street in heels! Lovely thought.

'Come, and trip it as ye go

On the light fantastic toe.'

John Milton

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Shopping together should be a blast. You should have zero issues in the Louboutin store as both here in Miami have never flinched at letting me try something on :)

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(formerly known as "JimC")

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Thank you all guys for your answers and tips. I will try to answer, reply or clarify in this post as much as possible, please keep up the tips and advice.

As I mentioned heel choice is up to my GF and it is part of the trip and fun, she (and I) want to try most of the time on stilettos, however that is the ultimate goal, we are both well aware that it is no entirely feasible nor practical or safe. But we will try as much as possible. She is not an ogre an trying to harm or cause me any pain, it us just fun to push boundaries as well as our limits. There will be some wedges (mostly for what you mentioned to change into something more practical), thicker heel boots in the suit case. But be wear high heels as much as possible.

We want try try and avoid as much as possible what @HappyinHeels advises to change at the venue, we want to wear them as much as possible.  But there is a reverse scenario we might just do, if we rent a motorcycle, then of curse no high heels but wear them over there then  change to more appropriate footwear. Although I have ridden in high heels it is not advisable nor smart (but so you feel so damn sexy and cool, just short rides when there is almost no traffic) specially on streets you don't know and a motorcycle that you are not 100% familiar with specially rented.

I know wanting something and actually doing it is not the same thing, we will try to stick as much as possible to our goals but we are not inflexible nor impractical, it is just nice to dream about the best case scenario.

Maybe San Francisco might be the best choice for this vacation/adventure, we will look into other locations.

@nzfreestylerRegarding your advice on the So Kate look amazing and that turned us to Pigalle Follies, once we really compared them the last seem so much sexier and pretty specially because of the thinner heel. You have given us a lot to think about and so much more fun trying and choosing. Thank you.

We will go shopping for other cheaper shoes together and try and get some more matching pairs but the Louboutins are a must now after your advise.

No we will not be flying yet. too many chances to be seen.

Although I have worn heels on an off at home for several years before meeting her, I have been working up my heel skills for about 7 months now. At home (either mine or my GF's) I wear high heels at least 90% of the time. I do not wear them when we have guests, and mostly for showering (although I did shower in wedges a couple of times at her request). Also started walking in high heels on a treadmill working up to longer distances and higher heels slowly. I do it in front of the TV with her just hanging out. Besides being a good exercise it really helped me with my high heel skills. This was jokingly suggested by my GF, when I first started wearing High heels around her. She said since I wanted to wear them and that I should because she thought it was so sexy, I should get as good as her in them she did not want to date a flappy duck on heels, lol.I tried the  treadmill first with boots about 4" heel but at a 1.5" platform and thicker heel. The thicker heel, platform and support from the boot made it easy to work up to 5 miles. Then I started working up with higher and thinner heels as well as using the tilt feature of the treadmill. Also I wear varied types of high heels to become good and comfortable in all kinds, but you could say my major is in stilettos, the other shoes are minors. Right now i can spend a full weekend, at home, wearing 4 inch stiletto pumps with no issues, including the treadmill exercise for about 5 miles a day, as well as cooking, cleaning, vacuuming and all chores, sometimes changing for a little while to 5 and 5.5", I am still working up to those heights (I have managed 2 miles in the treadmill and 8 hours around the house int he 5").

I know it is different than doing it on the street but we though this might be the best way to work up to it. We just want to make the most of our trip, we will not be disappointed if we cannot achieve our list (The Louboutins are not negotiable they are a MUST), but what fun would it be without it? as I said try to push the envelope and ourselves a little bit.

 

Thanks a lot again for your answers and support, we will keep posting updates and ideas

 

 

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Congratulations @heelguypa.As i am also using the treadmill as a double (heels and health ) purpose,I perfectly realize how difficult it could be. 

Its not so easy to walk in a perfect line on the treadmill. So,despite the fact walking outside could be different it's a perfect training. Keep on training and posting !! 

Pierre 

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Ok Guys, gears are turning and ideas are flowing.

My GF has already selected the first heels we will take there and the ones I will wear for the second item on the list "The same as before but wearing pink or very girly and flashy high heel stilettos".

She does not want to spoil the trip and trip pictures yet, so I am sending an internet pic from the shows, they are amazing:

ZJFAB287_OUT_LG.thumb.jpg.01bf71b6c3187e82e81082cf4087982f.jpg

 

She is thinking very hard about this and what she wants me to wear. As well as er and since we share shoes, well she shares hers with me, I have very few of my own so far.

She is also browsing the internet for different shoes to buy and I will be posting her choices or as we have talked when if she is not sure she might make me post it here for opinions.

This trip is getting better and better, just planning it and sharing it with you guys is a thrill, I am getting more exited like a child before Christmas about this.

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Hello all:

After reading some older topics on this forum, it seems another great place to wear high heels is Las Vegas. So we are considering a road trip, start in SF stay there 7 or 8 days and drive or fly to Las Vegas for the remainder of the trip.

I will be posting a few more shoe choices she is thinking about, from her collection and some purchases online, an also some more boundaries she is thinking about pushing, keep tuned

Any thoughts?

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Hello all:

My girlfriend is getting more and more exited by the minute about the trip, more so than before, her shoe search is getting more serious, I think it is also an excuse to buy more shoes fir her, LOL.

She is coming around a little but on the flats but she said when I chose to wear flats after i am tired of heels the will be extremely girlie flats with rhinestones, sequins, bows, very colorful flowers patterns and the like. I will show you her choices as soon as she has them.

also she said we should start posting here shoe choices for your opinions, starting with the ones we have at home now. We will in the next couple of days.

Another evolution of the trip, all thanks to @balletboot latest thread where he shows us his amazing outfits with skirts. She would like to try that, I am not sure yet, but she had her private fashion show this weekend, she had me try some of her skirts and dresses and played dress up. Pictures will follow soon. About this I am not so sure yet, I think  lets start and step at a time, but we will see, she is so supporting and she enjoys this so much that I at least owe it some hard thinking.

And for your shoe enjoyment, she is adding this to her purchase list, we found them after I found an old shoe identification request on this forum and found and posted the site for him @Dean. As soon as we saw the sites offerings we were amazed at such beautiful shoes they have, and for you guys that need larger sizes they carry up to 15US and offer customization: heel height, width,... you should check them out. Lets not digress much, these are the shoes and the link to them:

fashion_silver_stiletto_boots_peep_toe_rinestone_buckle_ankle_boots_1.jpg.030eb408b48ef54726351d0f956768f2.jpgfashion_silver_stiletto_boots_peep_toe_rinestone_buckle_ankle_boots_02.jpg.447e415e37a98c01c04c5ee91b381311.jpgfashion_silver_stiletto_boots_peep_toe_rinestone_buckle_ankle_boots_03.jpg.0eaab2d0c51ea2037d2c17a75474548e.jpg

https://www.fsjshoes.com/fashion-pink-lace-up-boots-pointy-toe-stiletto-heels-ankle-boots-8760.html

They are really beautiful and amazing but maybe a little too much for me yet? I am not sure but they sure are incredible.

Let me know tour thoughts.

Thanks again all of you.

 

Edited by heelguypa
Forgot link mentioned
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I am sooooo envious of you, and I'd love to walk in either of those pairs in SF. The hills would be a delightful challenge, particularly in the pink ones, where you have the higher centre of gravity of the platform to contend with! I can picture you in Lombard Street...

'Come, and trip it as ye go

On the light fantastic toe.'

John Milton

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8 hours ago, Tacchi Alti said:

I am sooooo envious of you, and I'd love to walk in either of those pairs in SF. The hills would be a delightful challenge,   ......  I can picture you in Lombard Street

LMAO...thank you Tacchi Alti!!! I haven't laughed that hard in a long time.

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LOL, yes it might be a real challenge, I guess we could try. she wants the pink shoes for a fancy night out, pinstripe suit, shirt, tie coordinated with the shoes. For dinner and drinks.

She is getting a shoe list together of must wear shoes for several occasions and then day shoes, but there is no harm in mixing it up and trying different things, also she slowly realizing that luggage space is limited, lol, and there will be shopping involved during the trip. Specially I think the Louboutins we purchase should come back in their original boxes, other shoes that purchase not necessary.

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heelguypa. you can expect a lot of excited women in a store like Louboutin. a number of heel wearing men on the forum have bought shoes and boots from expensive stores like Louboutin. jimmy choo, and the response was one of amazement and being admired from staff and customers.

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15 hours ago, Cali said:

LMAO...thank you Tacchi Alti!!! I haven't laughed that hard in a long time.

I love a challenge in heels. One last year was a hump-back bridge over a stream. The gradient was about 1 in 2 and I was in 4 inch heels. Did it... The piers in SF in stilettos? You might have to zig-zag down Lombard Street rather than take the footpath. Crossing the road on a steep hill is another challenge. In platform stilettos it would be a bit hairy!

14 hours ago, heelguypa said:

LOL, yes it might be a real challenge, I guess we could try. she wants the pink shoes for a fancy night out, pinstripe suit, shirt, tie coordinated with the shoes. For dinner and drinks.

She is getting a shoe list together of must wear shoes for several occasions and then day shoes, but there is no harm in mixing it up and trying different things, also she slowly realizing that luggage space is limited, lol, and there will be shopping involved during the trip. Specially I think the Louboutins we purchase should come back in their original boxes, other shoes that purchase not necessary.

You are so, so lucky! I usually wear fairly restrained styles (eg wedges or block heels) in public but if I was dared, and had the person that dared me with me, I'd wear almost anything so long as I could walk reasonably well in them. That means nothing over six inches with no platform.

'Come, and trip it as ye go

On the light fantastic toe.'

John Milton

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  • 3 weeks later...

Hello All:

The planing is still going good, more posts and pictures will come next week.

My girlfriend wanted girls opinions as well so I asked Tech to move this the for Everybody section.

We will be posting shoes, outfits asking for opinions, and maybe a challenge or public request, such as you guys vote and choose a shoe for me to wear on an outing.

As for the pink shoes I posted earlier they are sold out online, but my girlfriend convinced her friend who bought them a while back to sell them to her, I am picking them up tomorrow and we will post pics.

She is also choosing form her collection as well as online lots of shoe styles, which will include flats (extremely girlie as stated earlier) and wedges. She is still adamant for stilettos as much as possible but we know it is not practical but we will try to push the boundaries.

SF and Vegas is almost a go, not only SF anymore.

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Thanks a lot.

@jeremy1986 not my favorite either, but my girlfriend is having so much fun planning this, what shoes to wear, outfits, outings and all that. And she so so supportive and more so encouraging for me to wear high heels that I oblige to all her wishes and requests.

@canadianbeaver17 She also loves this Forum and how all of you are so supportive and encouraging. Sh is also glad I am not the only guy that wears high heels as well as she is not the only girl that supports and enjoys guys, especially me, wearing high heels. That is why she asked me to have this moved to the for everybody forum.

As I said we will posting pictures soon, had a few hectic days, being a long holiday so lots of partying, lol.

 

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4 hours ago, heelguypa said:

Thanks a lot.

@jeremy1986 not my favorite either, but my girlfriend is having so much fun planning this, what shoes to wear, outfits, outings and all that. And she so so supportive and more so encouraging for me to wear high heels that I oblige to all her wishes and requests.

@canadianbeaver17 She also loves this Forum and how all of you are so supportive and encouraging. Sh is also glad I am not the only guy that wears high heels as well as she is not the only girl that supports and enjoys guys, especially me, wearing high heels. That is why she asked me to have this moved to the for everybody forum.

As I said we will posting pictures soon, had a few hectic days, being a long holiday so lots of partying, lol.

 

That's great - enjoy it, both of you :)

 

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  • 1 month later...

Hello all:

First I am sorry this topic has been abandoned but things have changed for  a while.

RANT ALERT, sorry guys this just started as a 3 line post explaining why I haven't bee active (although reading some other  topics), and words and sentences started pouring out. I also apologize if this is inappropriate or not heel related, just let me know I will promptly delete it I do not want offend any one. Thank you guys for allowing me to rant and vent a little bit since some of the stuff I discussed here cannot be discussed with any of my IRL friends.

The trip is postponed, maybe august if things line up correctly.

The thing is instead of getting the promotion my girlfriend had been waiting and working for she was fired from her job no need to get into details, just management thinks instead of paying her high salary they rather hire 3 new kids fresh form college for the same amount (starting salaries are really low here).

So she has been looking and of course depressed about it. She had been so looking forward to this trip and all her enthusiasm looking for shoes for us to wear and for our collection is no longer something she looks forward but something that stresses her, that and anything that is an expense. So all that has been put to sleep for the time being. I have been as supportive as possible and she will get to her normal self soon enough. She has some interviews lined up so things will pick. She stopped all the "fashion shows" she was doing with me on weekends for fun just for the of us (some pics were selected to upload here and more were to come). She stopped all her browsing and selecting new shoes styles and a little wardrobe as well.

I have been wearing my heels at home a little less, especially when she is around and of course mostly my heels and maybe some that she left at my place. No that it upsets her that i wear them but it reminds her of the trip and more expenses.

There has been just a new kinda related to high heels at least she thought it did. One day soon after she was fired I'd say around 10 days, she was shaving a bad day, and was angry because she needed to spend some money on her usual beauty routine, many, pedi, hair, waxing..... all that. And started thinking about ways to save on those. first she said her hair can wait and use her hair dryer more often after shower at home. She would skip the mani and di them herself, the pedi had to stay. And since she hates shaving and only does if she must she said she would try those at home waxing strip that you rub between your hands. So a couple of days go by, it is the weekend and she arrives at my place completely mad, fuming, something about shipping and the clerk, just usual stuff  that pisses her off, but added to how she was and the reason for purchasing the waxing strips, she was a little madder than usual (the level usually reserved for me when I piss her off, lol). So I try and comfort her try to talk her down support her (I offered to pay for all and that she could keep her routine and a sense of normalcy that but she refused). Long story short I say a couple of bad jokes and puns, she gets more pissed off, and then a devilish grin shows up, and basically says if this is all a joke for you and I am not sure how well these strips will work, your are my guinea pig, pants down... She used the strips on my lower legs, the final result was not perfect but according to her not that was as a light touch up wit a razor would make it ok. We had talked about me shaving to try it but since the fashion shows stopped we no longer discussed it. She then told to leave her alone, she did her thing came back down smiling a little but, had not seen her smile since she was fired. She then hugged me and sorry about that I did not mean to hurt you, but to be honest it really helped me get rid of the anger and use in a productive way. I said it did not hurt as much as thought it would, and that the feeling was weird but pleasant. And she decreed once she is financially ok again she wants to take me to a salon for a real full waxing. If it makes her happy I can agree to that since she supports me so much specially wearing high heels. She said my legs looked so much better with stilettos and no hair. I am no really looking forward to that, I did impose to limits on it, no chest and no arms, so i look normal unless I strip down. also she agreed no beach unless it is just the 2 of us at her parents beach house, no one else but her will see me like that, at least for now. Maybe in high heels, lol.

After that day there was no more mentions of high heels, waxing, the trip, fashion shows and it has been over a month since I will however be there for her and support her as much as possible. I know once she gets a job and security she will be back to her old self. Also I wan to make it clear that she is in no way extremely depressed mopping all day, she is a little bit depressed, sad disappointed, nothing too extreme and of course she has good and bad days as all us do. She started job hunting the very next day. Met with a few head hunters within 2 or 3 weeks and applying to jobs almost daily.

@luvheelsmuch she we will post some pictures of me mostly, some of our collection and some as a couple wearing high heels, matching shoes and maybe as she once said on our fashion shows matching outfits. I just want to give her the space and time she needs, she comes first before any shoes.

 

Thanks again

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