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My wife, when she was alive, had only one restriction: That when I went out with her that I present as a man. Otherwise I was free to do anything, including being on estrogen. She even encouraged...

Quite simply why I wear dresses is I'm sick and tired of seeing so many people wearing trousers.

John

Um, I'm a man who wears a bra with a cup size of DD with no forms or filler. So I wear one for the same reasons as do women.
But I'm careful not to allow my bra straps to show as I'm a man.

John

I have NEVER purged any of my "feminine" clothes as I was not brought up to feel guilty for wearing those clothes. Also I don't like to throw anything away unless it is passed its useful life.
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We can blame the dull and drab male attire to The Great Male Renunciation that occurred in the mid 1700's. Before that calamitous trend male attire was elaborate and colorful. This topic is...

My normal attire is a dress and I have hair beyond my shoulders along with a bust. So you might say I'm dressed all the time unless I'm doing something like climbing on the roof to trim vegetation...

Considering that I wear dresses almost all the time, including shopping, doctor appointments, and church I say you should be able to wear dresses at a senior living center.
The pushback for my...

With my DD boobs I have to wear a bra whenever I drive or ride in a vehicle as the jouncing of the breasts is annoying without a bra.

John

I tried on a white cotton and linen dress yesterday to wear to church. Unfortunately the dress which otherwise fit me was too tight in the bust area so I had to wear a different white dress that I...

I started wearing bras about 12 years ago when I was 60 years of age. I started with a B cup size. But thanks to estrogen I have developed into a DD cup. However, I wear men's cotton briefs as I...

And perhaps in gym class you were unlucky enough to wind up on the Skins (shirtless) team for basketball.

John

When I'm in male mode (which is not often) I don't try to hide my DD boobs. And yes, as a man I wear dresses most of the time.
And I have a bass singing voice. Does that make me a Busty Basso? :)...

The question for me is when I don't go out on the street dressed like a woman? Not very often as I wear dresses around the house and when I.go shopping, to church and to doctor appointments.
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I notice when I am dressed en femme at church women will give me hugs. I don't get that behavior much when I am in male mode, which is not often.

John

Robin,
I have gotten virtually no pushback for presenting like a woman.

John

The only time I don't present myself like a woman is when sometimes I wear a man's coat, tie, and trousers on Sunday morning. I have hair longer than shoulder length and a bust. My voice however,...

I sometimes have a moment when I feel that a woman is looking back at me in the morning while standing before a mirror while wearing a summer nightgown. That, however, disappears when I sing with my...

I had a very interesting experience today going to a doctor appointment today. I wore a long sleeve maxidress and makeup. The nurse, who remembered me, asked me how my job at Victoria Secrets was...

Joey, it will get easier for you to go out wearing your outfit. I don't give a second thought about going out en femme which is my normal presentation. That includes shopping, church, and doctor...

Yes, there are things I do where I have to wear trousers such a replacing roof shingles and running wires through the attic. And yes, sometimes I wear a man's coat and tie outfit on Sunday mornings....

Dresses are far less of a hassle than a shirt and trousers. I just slip on a dress instead of having to fiddle and coordinate a top and a bottom.. Also I don't have that wedge of cloth against my...

Dresses are my go to clothing except for wearing trousers on an occasional basis. And for formal wear I add nail varnish (polish), makeup, and heels. So I would say free styling (cross dressing) is...

If I ever get married again I might be dressed en femme but with my real masculine name of John. My wife passed away on 2023 April 4 and it's mighty lonely.to not have a wife anymore.

Jessica, if...

I have been on estrogen for 12 years and have acquired a feminine appearance although I still have my masculine bass voice. My hair comes down 5 centimeters below my shoulders and my bra cup size is...

Thank goodness I have the confidence to dress en femme at home and then go out to do my business, whether it is out shopping, to church, and to doctor appointments. And I do not use stick-on nails;...