#708704
Jennifer Connolly
Baroness
Registered On: November 27, 2022
Topics: 8
Replies: 121
Has thanked: 293 times
Been thanked: 669 times

I love this question.  I’ve read as many answers to this question as I can find in searches.

I can recall my first time.  Some friends and I were playing in the basement, and decided to play dress up.  So the washer was in the basement with us, and my Mother had thrown away some old panties.  One of my friends said that I should put them on, but I was thinking to myself how much I wanted to do it, but didn’t.  I was scared that they would tell someone and make fun of me, after all it was the early 60’s.  So that episode got me to thinking about how much I wanted to do it if I didn’t get caught.  Then one day when I was about 9 years old, my Mother had washed an old fashioned girdle, and asked me to go get it, and I just had to try it on even over my clothes.  That’s where it all started.  After that I got brave and asked my Mother if I could dress as a girl one Halloween.  She thought it was OK, and said that other people had done it in the past after I asked about it.  I remember her taking me to the local small town store where she had me trying on a girls bonnet, since wigs were expensive back then.  When someone else walked in the store, she said,” he wants to be a girl for Halloween”, with a disgusted look on her face.  So she dressed me that Halloween in a pleated skirt, one of her orange sweater tops, a female mask, and that bonnet.  I looked like a boy dressed as a girl, and felt embarrassed about it, but all I knew was that I wanted to do it again.

You would think that with all the negative feedback I got, I wouldn’t have done it again, but our compulsion to dress is so strong that here I am today.

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