Walking in heels in the middle of the night for the first time

[redtea]

What a wonderful rush, I felt like a pretty girl extremely vulnerable even though i haven't done anything to my head yet.

I wore a white front lacy camisole with a racerback bra
a cool strappy pair of panties from VS
AOE blue jean shorties with clean shaven legs

And to top it all off, my brand new Funtaisma white high heels. I must say shopping for heels on Amazon is tough being a size 14. My options were fairly limited and there were lots of things that were my 1st 2nd 3rd choice that they simply didn't have in my size.

I contemplated doing the walk for like 45 minutes and ultimately took the plunge.

Only 1 car drove past me (i was on a sidewalk) but there were lots of people out walking that night. It felt like a game of "don't get too close to people or they could comment on what a pretty sissy boy you are"

I didn't go far at all, Just the small loop I do for every new article of clothing i get to sort of break it in and get over the initial fear.
I might go for another walk as these rare chances of having the night to myself only come maybe 5 times a year.


Heels without a doubt add a massive element of fear and anxiety to public walking. When i wear flats I can jog a little if i want to cut a corner and avoid being seen by a car.
With heels, I have no choice but to embrace being seen.

And of course the best part was practicing the walk, which to my amazement, got very good at. I still have a few issues with a few steps applying too much pressure on the toe but I didn't fall AND i walked down 34 steps and walked up 34 steps in a motel like apartment complex. The anxiety of slowly walking down the apartment halls thinking "if my pretty neighbor decides to go out at this moment, i'm really in for it".


Why push myself to do this? Because I've lived my life pretending to be normal for far too long. I really want courage more than anything else. There are beautiful girls that i can't say a word to other than hello or something that is a scripted exchange related to my job. I want to live life like I was in a dream, ignorant of the consequences my fears like to shroud me in. within moral reason of course. I want to be very impressionable one day and change the way people think of crossdressers.


Course the ultimate challenge is to wear what i wore tonight to the mall and go shopping in VS. At that point, It's safe to say I would no longer be worried about "people getting the wrong idea". I will be the true sigma male i always wanted to be. A MIAD who owns it. Defeating fear with confidence.


But sadly i'm not sure i will ever reach that point...

[Cwest862]

Yes, the walk takes practice. I got lots of practice walking in the annual "walk-a-mile-in-her-shoes" event for sexual assault awareness. One year I even had thigh high patent red high-heeled boots. I told my wife I was doing it as a fund raiser, but secretly it was fulfilling part of my need to dress.

Don't sell yourself cheap. You are already out walking in your neighborhood. I think in time you will own it and go shopping at the mall. Dare greatly!

[Tracii G]

Lets see a pic of the outfit with you in it.
I'm trying to picture it in my head.
What time of night is this happening?

[Teresa]

Redtea,
The fun has just begun, heels around the house are easy especially on soft carpet . Stepping out the door suddenly it all changes , you find soon enough if the shoes were a good buy or not . Very sensible not to have walked too far, once heels start to hurt every step becomes more and more painful . So you've done stairs great if you have a hand rail but take care without one when there's nothing to grab on the way down . So you need to progess onto gravel , soft grass , slippery tiled/wood floors and cobblestones , also learn to avoid some of those , gravel especially is a killer for heels it can soon strip the heel tip bare ! Not good when you've spent good money for the little darlings ! Also a tip about feet , take better care of them and apply cream to keep the skin soft , I try to keep my nails short , once a nail has chafed for a while the damage can take weeks sometimes to heal .

As for the Mall , don't worry it will happen , maybe when you get to that point buy some nice heeled wedges they will blend in more and tend to be more comfortable if you intend to do some serious shopping .

[redtea]

To my amazement, walking outside was much easier than the practice on the carpet. Carpet reduces balance a lot more.


Sadly the satisfaction of heels isn't too great.
Walking at 50% speed doesn't feel good
having to focus a little on steps isn't too fun. I actually fell once on my second time out that night because i was looking to my left to see if my neighbor was at their window and stepped wrong. Luckily i had fallen once before in the apartment so i know what to expect and to just sort of lower yourself and roll to reduce the impact.


People run in heels? THEY RUN IN HEELS?!?!?

The ones i got are pretty high, like 4-5 inches. The 1-3 inch ones didn't seem too appealing. Plus the toe part was also raised a good 2 inches, so i felt really tall.

[SIZE=1]- - - Updated - - -[/SIZE]

Lets see a pic of the outfit with you in it.
I'm trying to picture it in my head.
What time of night is this happening?

I don't take pictures of myself, That would seem like a whole new can of worms i'd rather avoid. Wouldn't want to end up being on Chatterbate because of some slippery slope of getting off to people seeing and commenting on my appearance.


Yeah yeah i know, you were on my last midnight walk thread to tell me how dangerous it could be. I don't plan on walking in the middle of the night forever, it's just a stepping stone to get my feet wet and increase my tolerance to humiliation. I actually don't like night walks as many times they are very uneventful and nobody even saw me except maybe 2 cars.

But going out in broad daylight in the that outfit with a male head is still too much to handle.

I feel pretty safe in the small city i'm in. It was 1AM when i went for a walk.
I also went for a 2nd walk at 3AM with my flats, and one more walk in heels at like 4:30AM.

[Teresa]

Redtea,
Yes it is possible to run in heels , thinking back to the days when you listened for the door catch and hearing it meant running and possibly taking two steps at a time on the stairs .

I sounds as if your shoes a little too loose if you go over on them , maybe you should have started with something lower and worked up . Sometimes women are suprised we can walk in them at all. I called in at my daughter's I had some heeled sandals on with a 3.5" inch heel she was amazed even more so when she saw me drive in them .