I was almost fourteen and, unlike all my friends, had not yet been able to jack off. They would invite me to a circle jerk and I would stand there stroking my cock until it got to a nice firm bone but nothing happened and eventually it would feel sore and get soft. A couple of the other boys tried to jack me but with no success at all. I was beginning to feel very inferior.
The summer I turned fourteen my mother's sister, Aunt Clare visited us and had the next bedroom to mine. She was older than my mother, about fifty I guess, but very nice. We talked a lot and played cards together and I got sort of a crush on her. She was what you call full-figured and I liked looking at her. On a Sunday we all went to church together and Aunt Clare and my mother were all dressed up with tailored outfits and stockings. I sat next to Aunt Clare and felt very excited. Was I in love or what? After church, Aunt Clare announced that she just had 'to get out of her girdle,' and went to her bedroom. A few minutes later I passed her open door and saw a beautiful six-garter, open-bottom, zipper girdle laying on her bed. For some reason, I just had to touch it. I went into her room, picked up the still warm girdle and felt the elastic and satin fabric and the dangling garters. I was strangely excited and, to my amazement, felt my cock getting fully hard. I pulled down my zipper, took out my boner and rubbed the girdle against it. The sensation was incredible.
Suddenly, I knew I had to put it on. I took the girdle into the bathroom, stripped off my clothes with trembling fingers and drew the tight garment over my hips. I connected the hooks and eyes on the side and pulled up the zipper, encasing my swollen cock tightly and pressing it upright against my abdoment. I looked in the mirror, admiring how the awesome feminine garment looked on me.
I felt a brand new sensation in my cock, fuller than when I had to piss. I knew something was about to happen. I ran my hands over the girdle fabric, not touching my cock, but enjoying the feeling of being tightly embraced. Then, without my willing it, my hips thrust forward as if to push my cock deeper into the girdle and the spasms started. First, a small gush of warmth came out of my cock into the girdle, then a mighty surge, followed by surge after surge pushing cream that oozed out through the fabric.
I was in heaven. Even today, many years later, whenever I want a really mighty ejaculation, I repeat that first virginal ejaculation with the same kind of girdle. Of course, now, I also put on stockings, a bra with forms, panties and a slip to complete my pleasure. It just proves that first masturbation experiences are often the most determinative of future desires.