First Time

The first time trying on women's clothing happened when I was about 8 or 9 years old. I was playing at a friend's house down the street. He wasn't a close friend, just a neighbor boy a year or 2 older than I. Anyway, we were outside playing and his parents weren't home. Out of the clear blue, he asked if I'd ever worn my mother's clothes. I don't remember my exact reaction but I'm sure I was slightly confused as the thought had never entered my mind. Anyway, i'm sure I said no and he said it was fun and into the house we went.
He lead me to his parent's room and started taking off his clothes and told me to do the same. Once naked, he opened up his mom's dresser drawers and started removing various items of undergarments. Bras, panties, slips, girdles, etc. Mostly white as I recall and mostly shiny smooth nylon. We spent the next hour or so trying on various combinations. I still vividly remember trying on a girdle and my friend getting a big chuckle out of it. I must have been much skinnier than he as he'd had to do a bit of tugging to get it up over his butt, but when I put it on, the girdle just slipped right on up.
Anyway, I found the whole thing exciting and pleasurable and was a bit disappointed when we had to stop. We never did it again but from then on, I tried wearing women's clothing...mostly underware and lingerie..whenever I could and still to to this day.
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3 Responses Jul 26, 2010

That first time is always the best.

I was dressed by my aunt from age 8 to 12.After she moved my mom continud to dress me.At 14 and over a friends house,he had 2 sisters 12 and 10,I noticed a laundry basket in the laundry room.The panties were nylon and all I had ever worn were cotton print briefs.So I took a pair and when home I put them on.A few days later while wearing a dress at home I wore the nylon panties under it.Well mom lifted the dress and I was caught and asked where I got them,scared I told her.She took me over to my friends house to tell his mom what I had done.He wasn't home but his sisters were,they laughted but his mom said she wasn't mad she only wished I had asked and then told my mom I did look pretty and she had some clothes for me

You were very lucky to have had the experience.