I had been babysitting Heather for a few years, maybe once a month for my sister-in-law. Our encounters started when she was 8, kissing, light touching, etc. When she was 10, I took things further. We escalated to oral sex, but I she never made me cum. Now it was a few months before her 11th birthday, she was over and we were on my bed. Both of us were naked. I had just finished going down on her and making her cum. I decided to try to go all the way with her. I grabbed some lube and loaded on her and my throbbing cock. I spread her legs and gently slid a the head in. She had no problem taking the head, so I pressed it in more. I am 8 inches and I comfortly had about 2 inches in, so I started pumping. Heather was moaning, saying ouch several times. I kept pumping.