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An Underdressing First (for me)

10 Posts
9 Users
27 Reactions
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Posts: 209
Lady
Topic starter
(@katherineboesemann)
Reputable Member     Cape Town, Western Cape, South Africa
Joined: 6 years ago

Home today after a three day long on-the-road-assignment, I donned my "wfh secretary outfit" after taking a shower and settling down to do my admin.
Needing to pop out briefly to the shops for a few items I'll need for tonight's supper, I felt resistant to the idea of taking off my sheer pantihose and bralette, knowing I'd have to dress up all over again on returning to the house.

I therefore kept on my lacy boyleg panty and hose and padded bralette (which was actually sold as a "light support sports bra") under my male pants and shirt.

It's now almost winter in the Southern Hemisphere of course, and this morning there was some drizzle with correspondingly chilly temperatures.

It was therefore not odd for me to walk around the supermarket wearing a zipped open rainjacket but anybody, I am sure, who miight have looked more closely, would have seen that I have a pair of smallish breasts.

 

I have frequently underdressed when going out, but usually nothing more than panties, hose perhaps, and camisoles (and of course painted toenails hidden in shoes).

Wearing a bra while out and about was at once thrilling and calming.

 

Apart from my occasional foray onto my fairly public driveway at night while fully dressed (including forms and wig), I have never been out and about as a woman. 

My late wife participated in my life as Katherine but it was strictly our little secret and she stopped short of completely letting me out of the house as a woman, but for years my desire to be a full woman in public spaces has intensified and wearing my bra today felt like another little step towards fulfilling that dream.

 

Love,

Katherine

  

 

 

 

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9 Replies
3 Replies
(@tubbydullard)
Joined: 2 years ago

Honorable Member     Citrus hills, Florida, United States of America
Posts: 426

@katherineboesemann encouragement; wear your bralettee more often when you go out shopping

 Eventually wear a maxi skirt too, you'll love the thrill, I promise ! 🥰

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Lady
(@joannajoy)
Joined: 6 months ago

Prominent Member     British Columbia, Canada
Posts: 383

@katherineboesemann congrats Katherine!! Step by step . You go girl!!

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 4559

Posted by: @katherineboesemann

It was therefore not odd for me to walk around the supermarket wearing a zipped open rainjacket but anybody, I am sure, who miight have looked more closely, would have seen that I have a pair of smallish breasts.

Congratulations on this new adventure abroad, Katherine! 

This is my modus operandi, too.

I have a collection of breast forms in different weights and shapes. The largest that I have is probably equivalent to maybe a C cup. The smallest is barely an A cup. This affords me the chance to pick a pair that suits the weather and the clothes necessary for that weather. The colder it is, the heavier the jacket or coat can be.

It has been so cold here, even in mid-May that I almost always wear a jacket even at the peak temperature of the day. I am taking too much risk in my neighborhood, but I haven't been clocked yet by anyone who knows me.

Use camouflage and obfuscation to make it difficult for someone to figure out what you are doing. 

 

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Posts: 15
Lady
(@mygurl)
Trusted Member     Stamford, Connecticut, United States of America
Joined: 1 month ago

Great account of your journey. Enjoy yourself.👗

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Posts: 212
Dame
(@aprilrhaynes)
Reputable Member     Pennsylvania, United States of America
Joined: 2 months ago

Doesn't it just feel sublime?  This was a freeing and next step on your journey, Katherine. I've no doubt I'll be reading a future post about Katherine being out and about.

 

Much love,

April ❤️ 

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Posts: 2500
 J J
Lady
(@jjandme)
Famed Member     California, United States of America
Joined: 6 years ago

Small steps will get you to where you want to go, so keep taking new steps. I think you will surprised just how few people notice, and even fewer , as in none, react or comment. 

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Posts: 855
 Leah
Baroness
(@leah63)
Noble Member     Minneapolis, Minnesota, United States of America
Joined: 7 years ago

I typically wear panties, bralette and camisole top daily   winter time with a thick sweater, I may wear a bra as well

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Posts: 8322
(@aliceunderwire)
Majestic Member     Near Burlington, Vermont, United States of America
Joined: 6 years ago

Hi Katherine,

With fall in the southern hemisphere and winter around the corner you’ll have other opportunities.

Alice

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Posts: 2500
 J J
Lady
(@jjandme)
Famed Member     California, United States of America
Joined: 6 years ago

My wife once said that I probably shouldn't go out in public dressed, and ai agreed that I probably shouldn't. But, I never said I wouldn't. Going out en femme is probaly my seconf favorite thing to do en femme. I will leave up to your imagination what number one is.☺️😘

You can either take your time and build up the confidence to be en femme in public, which is what I did, or you can just decide to do it and go for it, which in hindsight, I wish I had, I would have had some much more chance and oppurtu ity to be out en femme. Still, it is fun to be out underdressed knowing what silky, sexy things you have on that only you know about. It is also fun to be a bit daring with your underdressing. While at first I hid things well, after a time I began showing things a bit. A thinner shirt that shows my bra outline, or a wardrobe malfunction so someone might get a peek, etc. 

Most of all, just have fun. To me dressing is all about the pleasure I get dressing en femme, be it at home, undreseed or out fully en femme. It is just a fun and pleasurable experience, and to me that is what my dressing is all about.

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