Not knowing you were really into wearing women's clothes ?

I turned down way too many opportunities when I was young and would love to hear about those that accepted the offer.

What specifically did you wear ? Did the female involved offer underwear also and if so was it plain or very girly ?

How much fun did you have and how much fun did she have ?

Later did she suspect you liked it too much ? LOL

The only thing i did close to this was having to play girl parts at my boarding school in the East. The teachers wives fawned over us putting us in cute Bras and slips and making us try on numerous dresses. It was amazing how much true joy these women seem to get in turning Teen age boys into girls and women. They espcially liked watching us struggle with putting on stockings and walking in heels.