Skirts (Dresses) worn by Males ###

[littleph0enix]

very cute i would wear that

thanks getting dressed up and posting about is not something I have ever done before though I really do love wearing that kind of stuff hehe

 

[Blueboy]

nice to see im not the only one that wanted to wait until the dead of night to just walk about XD. the fear and excitement is 100% there since I flipped a coin as to if I did it or not and when I did kind of could not stop myself from going out even further. (first stop was a playground near me but I was soon like I could take this further haha) end up in the bigger play area/ pack near town with all the shops, scared the shit out of me when I saw people around bits here and there lol.

I really love the style of your 2nd dress, I sadly dont have much right now but I am looking at getting one of these 2 for my next buy at some point.
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wow you look so good, love your shoes? boots? sorry not sure look great though

I dont have much for now but here is the first thing I got that I like and what I walked around town in at night that one time XD :
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hmm I am worse at taking pic's of myself then I was thinking oh well, (did 3 since I didn't know which was better, all seem bad to me...) and yes I know I have too much petticoat going on and not so much skirt XD didn't think it was this bad but I just felt like one was not puffy enough to the point I was happy hehehe

Wow very nice hehe

 

[Fireball44]

I like skirts, but my miniskirt does not work with diapers. I don't like to purposely show off my diapers.

nice pictures, i've been wearing a little longer skirt, and some wrap around skirts with leotards and tights under my skirt. I love wearing pantyhose or tights under my skirt, lots of times out with a disposible diaper panty.

 

[Fireball44]

A great choice she made...

love diapers to wet under my pantyhose and socks over my pantyhosed leggs,Feel so sexy and fertile when wet.

 

[GatoChihuahua]

I have recently worn these two dresses and a skirt to work (retail), the magenta/indigo turtle neck sweater minidress reminds of Lana Kane from the Archer TV show. I wore this over blue jeans because skirts have to cover the knees at work. I skirted their rules



I did not wear my boobs at work, but I put them on before taking this photo. It was "wear something red" day. I love this red sweater dress. The shiny metal rivets all over the front sparkle and catch the eye a lot more IRL instead of a photo. I wore black dress trousers underneath because of the shortness of the skirt with regards to work's dress code.




I finally gathered enough stones to wear a skirt with tights to work. No pants to protect my modesty.



The Lana Kane dress over jeans was my first dress worn out in public since the 90's. I got a few compliments and now it's snowballing.

 

[Ali123]

View attachment 93459Mommy's choice for me

That’s delicious! I love how you can still see your nappy through your skirt.

 

[RachelOlivia]

I have recently worn these two dresses and a skirt to work (retail), the magenta/indigo turtle neck sweater minidress reminds of Lana Kane from the Archer TV show. I wore this over blue jeans because skirts have to cover the knees at work. I skirted their rules

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I did not wear my boobs at work, but I put them on before taking this photo. It was "wear something red" day. I love this red sweater dress. The shiny metal rivets all over the front sparkle and catch the eye a lot more IRL instead of a photo. I wore black dress trousers underneath because of the shortness of the skirt with regards to work's dress code.


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I finally gathered enough stones to wear a skirt with tights to work. No pants to protect my modesty.

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The Lana Kane dress over jeans was my first dress worn out in public since the 90's. I got a few compliments and now it's snowballing.

Well done you.

 

[BabyprinceS]

That’s delicious! I love how you can still see your nappy through your skirt.

Thanks

 

[Blueboy]

Here’s my wittle skirt for the night hehe

 

[james6416]

Yesterday's fun

 

[Ali123]

Yesterday's fun

How sweet! No hiding your nappy under such a little flared skirt!

 

[stuckin60s]

Yesterday's fun

Just love the diaper peeking out from under your skirt.

 

[Deleted member 64479]

View attachment 93459Mommy's choice for me

Ok... That's just adorable!

 

[claire123]

Ugghh!, that's me!.
I've been wearing my girlfriend's cheerleader skirts and her bridesmaid dresses too.
(Why women don't wear some type of shorts under their dresses or skirt?).

that was a thing when I was in high school shorts under skirts the shortest skirts possible so same for shorts

 

[Jorelaxed]

Oh yes me too

Uh oh!, diaper peeking out underskirt.

 

[BobbiSueEllen]

I love wearing big baby girl dresses! They're cute, simple, comfy and have this aura of innocence & sweetness to 'em.

I have several basic play/nightie dresses, one casual pink gingham sailor dress...and coming soon: one pink "kinda-formal" '50s/'60s dress with Peter Pan collar, puffy sleeves, a sash for a cute bow in back ...and with a skirt that allows the slightest peek-a-boo view of my diaper or matching diaper cover. It'll have a petticoat, too, which will give the skirt a little bit of body...like that of a small schoolgirl.

 

[michaelmc]

Skorts are short skirts with shorts built in. They keep the private parts private. I love them.

I don't like skorts myself ... the flash of panties is so exhilarating that fleeting glimpse puts a smile on my face! lol

 

[michaelmc]

Is this any better? Here is a cute little jumper with Pampers Cruisers... My wife does like when I wear this as diaper checks and changes are much easier...

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An iron on embroiderd patch like Minni mouse or the likes put on the chest would look awesome

 

[michaelmc]

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Two of my many

 

[star]

I used to think like that, but it really isn’t a big deal.

I first went out in a skirt when I was fourteen - terrified that everyone would stop, stare and point at me. And do you know what actually happened? Nothing. No-one batted an eyelid.

I think more judgment lives in your own head than exists in the outside world. Everyone is tol busy with their own life. It's like "ooh, a boy in a skirt", for about three seconds, then back to their own day-to-day worries.

Personally I love to see people out expressing who they are. I feel good for them. I love unconventional..Conventional is boring.