Lots of 'first time' stories. Here's mine.
I was 18 when it happened. This was over 20 years ago. I was out with this boy named Dave on our third date. We ended up parked in front of my house kissing each other. This went on for a good 20 to 30 minutes and I finally told Dave I better get in. He then told me that he'd have to wait a few minutes before he could walk me to the front door. I ask him why the wait. Dave looked at me and said 'You don't really want to know'. I told him I did. He said 'If you really must know' and then turned on the interior lights and leaned back in his seat and pointed to his crotch. He was wearing a pair of light blue slacks and what he was pointing to was more than obvious.
I let out a little gasp and put my hand over my mouth when I first looked at the big bulge running down his left leg. It looked enormous. I slowly reached down to touch it. I could hardly believe how hard it felt. The slacks were a very thin material and I could actually feel the warmness coming off of his big hard-on. I instinctively ran my hand up and down the shaft. This was all it took. Dave let out a deep breath and I could feel his cock literally throbbing in my hand and saw the wetness start at the end of it. Dave ejaculated right there in his pants from the touch of my hand on his cock. This was my first hand job I ever gave a boy.
From this time on, Dave couldn't wait for a repeat performance. Of course, after this first time, Dave would pull down his pants and I'd grip his cock in my hand and stroke it and would watch him come. Dave would feel on my tits or finger my pussy while I jerked him off. This was how my sex life started and I've had a very full and active one ever since.