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Jul 29, · 22 Stories Of People's First Orgasms I've had so many bad sexual experiences in the past, that it was hard for me to enjoy any sex now. "The first time I orgasmed was my first time. Nov 02, · My now boyfriend went down on me on our first date. I had no sexual experience and while I had masturbated before, it was never to orgasm. When he was done, my whole body was shaking for at least ten minutes. I started dating my first serious boyfriend towards the end of my senior year. Our second kiss ever was at my senior prom, so I ended.