I was twelve, and although it seemed like I had a boner all the time, I had never had an ejaculation. No matter how much I stroked or rubbed, nothing ever happened, other than a slippery drop oozing out of the tip. A friend at school even tried to jack me and it really felt good but no squirts.
One day I decided to explore the bedroom of a live-in helper. She was about 28 or so and I often got a hard-on when I talked to her. She was out shopping and no one else was home when I went into her closet. The combined smells of perfume, powder and well-worn feminine clothing gave me a strangely passionate feeling and the start of a tingle in my cock and ball sack. On a shelf I found a simple four-garter open bottom girdle with alternate panels of elastic and satin. I rubbed it against my face and sucked one of the dangling garters. Suddenly I knew I had to put it on.
I couldn't believe the sensation. Was I some kind of queer that wanted to wear women's underwear? No matter, all I knew was that the thought of wearing the girdle was making me more excited than I had ever known. I stripped off my clothes and quickly tugged the tight garment over my hips and up until it flattened my stiff cock against my belly. The caress of the elastic around my hips and ass and the touch of the dangling garters was giving me sensations I had never known.
Suddenly my cock felt full as if I had to pee. Quickly I dashed to the bathroom, pulled up the bottom hem of the girdle and strained to piss but nothing came out except a drop of goo. I smeared it around the head and, for the first time, it occured to me that maybe I was about to come. I pulled the girdle back into place, returned to her closet and admired myself in the full length mirror.
Then the full feeling came back to my cock. I felt a spasm deep inside and the girdle seemed to answer with a squeeze. Another spasm and then I knew something was about to come out. Instinctively, my hips shot forward as if to drive my cock deeper into the girdle and then the first gush came, followed by three more. I looked down to see the white cream oozing through the fabric as I experienced spasm after spasm and the girdle answered back.
I was in heaven. My first jack off and I hadn't even done it myself! It was all because of the tight smooth embrace of the girdle. After that I was a confirmed girdle and pantie masturbator. Later when my first sex partner and I masturbated each other, she liked to take off her panties and wrap them around my cock and watch the cream squirt into them.
You might have thought that I would become gay after that first girdle jack but I have always been just an admirer of and masturbator with women's lingerie. They say you never forget your first orgasm and it's so true.