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My earliest recollection of nylons is when I was very young (early  50's). My Aunt Helen, who lived with us, worked as a secretary at a  trucking company, and as such, always wore dresses or skirts to work. I  remember that when she got home from work, she'd sit on the couch and  take her stockings and high heels off, and leave them there until she  went to bed. 
    
I was fascinated with her legs, and I still remember exactly what they  looked (and felt)like-she had great legs! She would hike her skirt up  above the tops of her stockings, and unclip the clasps on her garter  belt, and then roll her sheer nylons down her legs, placing them in her  shoes. Being as young as I was, it was no big deal that I'd  consistently watch her, and on occasion, even catch a glimpse up her  skirt or dress. 
Once in awhile, I'd run up to her to greet her, and hug her around her  legs. I'd rub her stocking clad thighs until she made me stop. I'm sure  that this is what hooked me! I simply loved the texture of the sheer,  slick nylon on her legs, and never got enough of feeling them. She  always warned me not to cause a run in her nylons, and I think that was  probably why I developed a dislike of runs and snags in nylons or  pantyhose, which I still hate today. An ugly run is almost as bad as NO  nylons at all!
One evening, Aunt Helen fell asleep on the couch, and I did what I'd  planned for quite awhile. I snuck in and grabbed her shoes and  stockings, and hid with them behind a big recliner chair. I took my own  shoes and socks off, and slid the sheer stockings onto my feet and up  my legs. WOW!! It was like an electric charge going up my legs, to my  crotch! If I didn't know better, I believe that I had my first orgasm  right then, it felt that good! 
Well, Aunt Helen woke up and caught me playing, and very sternly told  me that I shouldn't be playing with her clothes, that boys didn't wear  stockings, and that they were very expensive, and I might cause a run  in them, at which point she would be very mad at me!