This happened shortly after my girlfriend Marsha and I had started dating. I was 18 at the time, and she was 17. We had been seeing each other for about six months at the time that this happened. Marsha was very cute and a little chubby with long brown hair and glasses. I hadn't been very sexually active before meeting her, and I was her first. But by this time we had both been playing catch-up, and had been doing a lot of experimenting together.
This one night we were in my bedroom with the light on. We were both naked and had just started messing around. Marsha had her head directly over my cock and was slowly pumping her hand up and down, while gazing at it almost lovingly. As she moved a little, her hair brushed the head of my cock, and I throbbed in her hand. She smiled at me and said 'I want to try something'. Then she removed her hand, wrapped some of her long hair around my cock, and put her fist back around it. Very slowly she started to stroke me, and the feeling was unbelievable. I had been masturbating for a very long time, but nothing had ever felt like this.
Marsha kept stroking me slowly, and her hair felt like silk wrapped around me. After only a couple of minutes my prick started to swell and I warned her that she'd better get her hair off of me, or she was going to get my cum in it. Her answer was 'Go ahead, I can wash it out'. That's all I needed to hear, and suddenly my cock started to erupt, shooting stream after stream of white cum all through her brown hair. She just smiled, feeling my cock go off in her hand.