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donontario · 70-79, M
I only wear the kilt, so I suppose I do.

DragonFruit · 61-69, M
Yes, I have worn a dress once or twice.
malizz · 70-79, M
Not often, but it's something every man should try, as long as it's in an accepting environment.

I wear a kilt regularly, but Highland outfits are not generally seen as female attire.
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malizz · 70-79, M
@silkydrawers Aye well, kilts are one thing, but, as I expect you know, with skirts or dresses, the knickers can make all the difference, especially if they're silky.
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Dear men of SW, have you ever been asked to crawl?
SW-User
No, never. Nor will I ever 😬
SW-User
@SW-User Noooooo 😱
SW-User
@SW-User those smexy robot legs can pull it off ..
or would you rather i pull off those robot legs 🤔 😂
SW-User
@SW-User Bad bunny! 😡
patkaren1717 · 41-45, M
Being a Cross Dresser i have many times.
StevetheSleeve · 31-35, M
High school. Reversed rolls with my girlfriend. Regretful.
Julien · 36-40, M
@Julien damn kilts are hawt
Ooft 😏
Julien · 36-40, M
@SW-User nop
Julien · 36-40, M
@PepsiColaP very itchy
Soxs45 ·
On Halloween
@Soxs45 what costume!
Soxs45 ·
@Dewms i just dressed up a girl in high school lol
@Soxs45 omgggg 🥰
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StevexStephie · 70-79
@silkydrawers I wish it could be much more often for me!
PTCdresser57 · 61-69, M
Yes..as much as possible.
lipstickguy · 61-69, M
I'm wearing one now
lubovont · 70-79, M
ElsaKaren · F
All the time
hlpflwthat · M
Have worn a kilt. And once wore a cheerleaders outfit for a skit at a prep rally. That look is immortalized in my high school yearbook.
Gusman · 61-69, M
No, never had the inclination
Imsleepy · 31-35
Nope, I have not.
redback · 51-55, M
Johnblackthorn · 56-60, M
I wear kilts when I not working.
AuRevoir · 36-40, M
James1956 · 61-69, M
MrBrownstone · 46-50, M
deadgerbil · 26-30, M
Pretzel · 70-79, M
Smokey · 46-50, M
SW-User
SW-User
🍿 👀
Like as an everyday wear choice? Nope. Don't really have the legs to pull it off 🤣
Jklove · M
Fock nooo😂

 
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