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29 Posts
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Posts: 3853
Lady
Topic starter
(@harriette)
Illustrious Member     Toronto, Ontario, Canada
Joined: 2 years ago

One of my tasks today was to pick up my wife's sweater that I had left with a local seamstress, to repair a hole that mysteriously appeared on its back.

At the same time, I was to leave three pairs of slacks that she had been waiting to get them hemmed. I had pinned one cuff such that it would break on top of her arch. The seamstress suggested that she could angle the cuff, so that it would look good with heels, too.

I told her that my wife doesn't wear heels, I wear the heels. This caught her by surprise and she smiled and chuckled. Then she added that she would like to see that. Challenge accepted.

So now I have to figure out how to manage this because it would mean that I have to walk about a quarter mile through my neighbourhood, in broad daylight, in warm weather, to get there. 🌞

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28 Replies
12 Replies
Baroness
(@annaredhead)
Joined: 10 months ago

Famed Member     Cornwall, United Kingdom
Posts: 1663

@harriette Good luck with that! I'm quite happy to walk from seeing my make up artist back to my car as it's nowhere near home whilst wearing heels. Walking from home....not a chance!

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 Lea
Lady
(@lea-jhene)
Joined: 9 years ago

Noble Member     California, United States of America
Posts: 1063

@harriette Sounds fun. May I suggest carrying the heels in a shopping bag and quickly changing into them when you're close to the seamstress. That might help with any fears of being seen. It also will help if walking that distance is just too much in heels. I'll be looking forward to your next update.

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(@frederica62)
Joined: 6 years ago

Estimable Member     Virginia, United States of America
Posts: 87

@harriette I've walked 100 plus yards in heels and nylons, and it doesn't take long for your feet to slide around and start to feel sore.......I'd suggest you put your heels in a bag and change once you're closer.

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 3853

@frederica62 I am wondering if I can get away with also wearing skin coloured pantyhose under shorts. I don't think that I have any stockings like that. It might be too much of a giveaway, though.

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(@frederica62)
Joined: 6 years ago

Estimable Member     Virginia, United States of America
Posts: 87

@harriette If you're wearing shorts then flesh coloured pantyhose will work very nicely. All you have to do is find the right 'flesh colour'. I've been to the supermarket in shorts and nylons and no-one paid any attention. Shaving your legs is a big help too, since you won't have hair to flatten down. After that, you fit the view of does he/doesn't he category. Of course, that'll all fall apart of you're wearing heels.

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 3853

@frederica62 It took a couple of years of using IPL, but my legs and thighs are now mostly cleared of that forest. I am still attacking a few very resistant areas, though.

Plus, I have good looking, long legs, so if I can, I will.

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(@frederica62)
Joined: 6 years ago

Estimable Member     Virginia, United States of America
Posts: 87

@harriette I'm 6 feet tall, also with long, good looking legs, and I'm very conscious of being too tall; particularly with a pair of 3 inch heels. Thoughts? Get on with it and don't worry?

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 3853

@frederica62 Well, I do have to wait for the hem jobs to be finished. 😉

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(@frederica62)
Joined: 6 years ago

Estimable Member     Virginia, United States of America
Posts: 87

@harriette I've been to bars near me with an SO; both of us wearing nylons and short skirts. It's quite electric to bump knees. I'd never thought about it until it happened.

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 3853

I learned something related with Google Maps.

GM has a feature that tracks the amount of cell phone traffic for locations, which indicates when it is busy or slow during opening hours and how now is different compared to their averages. When I tried to find their chart for the seamstress, it didn't exist.

I guess Ella was too insignificant or small to track.

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 3853

Today, I chose to do some laundry and tidy up my closet, etc. I experimented, a bit, to see what may work here. I am still working on it, but I narrowed down which shoes to wear to two pairs. Three inch dark, dark red (brown?), very comfortable Stuart Weitzman or some two inch black not so comfortable Clark's.

I flipped through my old drab clothes pushed into a corner and found a bunch of old shirts with yellowed collars. They will never change, so out they go. It made room to hang up so more new female clothes. A win-win.

While doing this, it became pretty obvious just how many pink men's shirts that I had collected. 🥳

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 3853

Today, I did it. I went to the seamstress and picked up my wife's items and dressed up for it. 

First of all, I had to be careful of what I wore because I had to go to my bank before walking to the store. I couldn't be too blatant in my neighbourhood about things just yet.

I picked out the shoes, ones with a reasonable 2.5" heel, but I wore some other new shoes to walk the whole distance. I put on black short shorts, to not hide my hairless legs. On top of those, I slipped on a black pencil skirt and pulled it up to my waist. I wore a small bra with my smallest forms. Lastly, I put on a dark gray and white vertical striped short-sleeved shirt, which seems to be a popular style for summer, and left it to hang down loose, to cover up the skirt and because it is annoyingly hot outside, today.

Walking to the bank, the small breast forms still drew a bit of attention, so I secreted them into my shoulder bag until I got close to the seamstress.

I walked past her door, to check if any customers were at the front. There were none. I stopped and stood in a nearby recessed doorway, to scope out the rush hour street traffic which was stopping as a herd, for red lights. Fortunately, there was no sidewalk traffic. So I timed slipping on my heels and pulled down my skirt, so that few could notice me, and opened her door. She works at her sewing machine 10-12' away and recognised me.

It took a few seconds for things to sink in, but she smiled and we started talking. I reminded her that she wanted to see me in heels and here I was.

After a few minutes, I didn't want to embarrass any of her customers if they suddenly came through her front door, so I started switching back to my androgynous mode. She seemed interested enough to watch me how I changed my presentation. She asked if these were my wife's clothes and I indicated with my hands that they were all mine, top to bottom. She said that I looked classy. I agree. 😁

I carefully asked if she had other crossdressers come to her and she said yes. They come in with their dresses, to get fitted, etc. I figured that would be the case even before asking.

So, she had asked to see me in heels and I took things a bit further, partly to challenge myself because I don't get the opportunity to do this kind of thing very often. No big cover-ups, as in winter, but a healthy dose of stealth nevertheless. My mouth had dried up, probably from being tense or under stress, so I went home, satisfied that I had had a good experience, to quench my thirst.

Given the right opportunity, yeah, I will do it again.

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Posts: 3277
Hostess
(@ab123)
Illustrious Member     Surrey, United Kingdom
Joined: 4 years ago

Fully femme or in drab - either way we will be awaiting the report with interest. 

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Posts: 192
 Lacy
Duchess
(@rholtman96)
Reputable Member     Lincoln city, Oregon, United States of America
Joined: 2 years ago

 You could always carry your heels in a bag and put them on just before you walk through the door, like a lot of women do after work.

Lacy

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Posts: 7734
(@aliceunderwire)
Illustrious Member     Near Burlington, Vermont, United States of America
Joined: 5 years ago
Harriette, I’m sure you’re up to the challenge.  Have fun.
 
Alice
Reply
Posts: 2026
Hostess
(@cdsue)
Famed Member     Delaware, United States of America
Joined: 5 years ago

Harriette -

Sounds like a fun challenge to me. As others have said take them in a bag and change before going in the store. Waiting to hear how it goes.

XOXO
Suzanne

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Posts: 716
Lady
(@sashabennett)
Noble Member     Wick, Caithness, United Kingdom
Joined: 1 year ago

Well, It would be rude not to as she asked so nicely 😆 

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Posts: 3853
Lady
Topic starter
(@harriette)
Illustrious Member     Toronto, Ontario, Canada
Joined: 2 years ago

@cdsue @rholtman96 @lea-jhene 

Yes, carrying high heels is definitely a possibility, but changing into them would be out in the open. It might work, though.

Another possibility would be to wear a relatively comfortable 2.5" block heel that wouldn't draw too much attention. It would allow me to walk the whole distance in them, too.

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4 Replies
 Lea
Lady
(@lea-jhene)
Joined: 9 years ago

Noble Member     California, United States of America
Posts: 1063

@harriette A block heel is a brilliant idea.

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Hostess
(@cdsue)
Joined: 5 years ago

Famed Member     Delaware, United States of America
Posts: 2026

@harriette block heels are a wonderful idea - I have a pair of ankle boots with 2" block heels that I wear out on occasion - my wife is okay with it as she says they look like cowboy boots - kitten heels would work as well - good luck and be sure to let us know how it goes

XOXO
Suzanne

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 3853

Posted by: @cdsue

@harriette block heels are a wonderful idea - I have a pair of ankle boots with 2" block heels that I wear out on occasion - my wife is okay with it as she says they look like cowboy boots

Exactly why I have worn them outside so much - they don't draw much attention at all. Not so much with the Mary-Janes, though. A New Year's Eve drunk noticed them. 🫣

 

Reply
 Lacy
Duchess
(@rholtman96)
Joined: 2 years ago

Reputable Member     Lincoln city, Oregon, United States of America
Posts: 192

@harriette I have a pair of wedge sandals that I've worn, and nobody has noticed.

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Posts: 712
Lady
(@jincrocker)
Prominent Member     Oregon, United States of America
Joined: 5 years ago

not sure I am up to that long of walk in heels!

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3 Replies
Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 3853

@jincrocker I can rock block heels all day. I have both Mary-Janes and more normal pumps. Spike heels outdoors is risky even for good, practiced, strong ankles. I don't have any kitten heels yet, but they would work, too.

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Lady
(@jincrocker)
Joined: 5 years ago

Prominent Member     Oregon, United States of America
Posts: 712

@harriette Nice, how did she react when you showed up in your girl things? I mostly get positive response from women, and neutral from other men.

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 3853

@jincrocker Most of the clothes that Hong has worked on are my wife's. I took one of my own dresses to her, to be altered, as a test run, but I didn't let any secrets out of the bag, at that time.

I will attempt to wear the heels in the next episode.

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Posts: 1618
Baroness Annual
(@secretpassions)
Noble Member     Wisconsin, United States of America
Joined: 3 years ago

It's hard to pass up a challenge like that. I'm looking forward to the next episode!!

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Posts: 81
Lady
(@sarahl)
Estimable Member     Kalamazoo , Michigan, United States of America
Joined: 2 years ago

Mission Impossible music starts playing.

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