The first one is etched indelibly in my mind and heart
I never understood why, but from a very early age, I wanted to wear dresses and skirts like my sisters. It was something that made me feel good, but it wasn't really a sexual thing for many years until one day when I stayed home from school with a tummy ache.
When I could convince mom to let me stay home from school, I would amuse myself by trying on my sister's things and sometimes, mom's too. I watched the clock carefully so that I could have everything put away by the time anybody came home from school or work. It was always very pleasurable for me to dress in feminine things, but always left me feeling a little guilty, too, since boys weren't supposed to do that. Nonetheless, I couldn't stop and I couldn't help myself.
On this occasion, when I was about 12 or 13-years-old, I had managed to stay home from school to play. Mom had a second-hand clothing store and would often bring home some of her finds. They were often of good quality, but generally outdated by the time they got to her shop.
The dress that caught my fancy was a lovely green satin vintage cocktail dress with short sleeves, a side zipper and a slim skirt topped with a flat bow at the waistline. The skirt hit just below my knees. I carefully borrowed a bra, a panty girdle, stockings, and a half slip from mom's lingerie drawer. I filled out the bra with some more stockings, pulled on the girdle and hooked up the hosiery to the garters on the girdle. I pulled on the slip and then I put on the dress.
The feeling of wearing all of this finery was totally luxurious. I walked around the house a little bit, careful not to be seen through any windows by neighbors. After a while, I laid down on my back in my bed ro rest. I had a very hard erection which the girdle did a nice job of hiding, but which I could feel through my dress and lingerie.
I was enjoying the experience tremendously as I idly rubbed the front of my dress. That felt very nice, actually, and I kept at it, making more nice feelings. Something seemed to run away with me. I rubbed faster and harder and had the most amazing, intense experience wash over me as I had my first orgasm and my first ejaculation ever.
After the obligatory sex education classes they had us attend at school, I knew what had happened and was, at the same time, panicking to get things cleaned up and put away and happy to have discovered such a wonderful thing to do for myself.
Needless to say, since that time, I have had many occasions to try on feminine things which always intensify the experience for me.
I'd enjoy hearing about others with a similar story to tell! This website is truly fun and wonderful!