Skirt Boys » Discussions

When Did You Lose Your Skirt Virginity?

 
  • When Did You Lose Your Skirt Virginity?

    Explain when and how you wore your first skirt/dress?

    I want to be a girl like you, The way you swing your hips in jeans,
    I want to wear my face like you, Shiseido Mac and Maybelline,
    I want to paint the town with you, And tickle you until you scream,
    I want to fall in love with you, I want to say I do
  • Probably never was...

    ...a skirt virgin.

    Up until the age of 6 I don't recall ever wearing a pair of pants. I was outfitted with little kilts and plain pleated skirts because my mother liked the style and remembered seeing many little boys so dressed when she was a child. The fashion of dressing little boys (up to the age of puberty--or even for a few years after) in skirts and dresses did not die out until well after WW-I. I count myself lucky because I have never felt uncomfortable when skirted.

    Edited by Confidentmale on 5 Sep 2007, 02:16
  • Probably should explain my first time

    Well it was my birthday party on 7th July 2007
    wore a nice and short tartan skirt also wore Stockings and a Girls t-Shirt
    It was a camp theme

    I want to be a girl like you, The way you swing your hips in jeans,
    I want to wear my face like you, Shiseido Mac and Maybelline,
    I want to paint the town with you, And tickle you until you scream,
    I want to fall in love with you, I want to say I do
  • So your birthday this year was your first time wearing a skirt?

    What did you think of it? It felt good, right? So free and easy. Did you like it? what would keep you from wearing a skirt again? And have you considered that there is no earthly reason why you shouldn't?

    • [Deleted user] said...
    • User
    • 25 Nov 2007, 21:51
    .

    Edited by a deleted user on 1 Mar 2011, 08:41
  • When I was about 14..I tried on my sisters gym skirt at her insistance..and really liked it! Been wearing them whenever I can ever since. Nothing I like more than going hill walking in Wales in a gym skirt. You get the odd funny look, be hey! who cares!

    Gym Skirts Rule!
  • Skirts

    1951 I had not much interest and could not decide, what to wear, normally a knitted skirt, 3 years later, there was a childrens carneval and i went as a girl, my younger sister was crying, because i got all attention which she normally got, later i tried disused clothing from my mother's wardrobe and wore that stuff swimming in the lake. About 8 years ago i bought my first kilt, then several skirts and more kilts. Skirts are nowerdays my usual wear, kilts are for more elegant occations. Sometimes i have the sensation of whispering and loughing behind my back - so what?

    I need no reason to buy new stuff - just money
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