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That fall Sis went away to college and my parents had a dilemma. They had to work in the city but there was this now-12-year-old boy who needed supervision. Mom first tried having me stay with neighbors, but they had kids of their own and it didn't work out. Then she tried a couple of housekeepers, women who cleaned the house and did the laundry as well as made my dinner. These didn't work out either because they couldn't make me do my homework.Finally, after almost a year, mom found a high-school junior who would meet me when I came home, see that I did my homework, cook me dinner, and stay until 9.It was Anne.Over that summer I had begun to mature. I had a small amount of fluffy pubic hair, my cock was now 4 inches long (4¼ inches if I cheated measuring), and I was capable of sustaining an erection. I was beating off to some porno my dad thought he'd hidden in his closet.For the first 2 days Anne and I didn't acknowledge we knew each other. We settled into a routine where I got home. I watched two guys begin to bareback on the video in the woods and fantasized that I was the guy getting fucked. I pushed the tip into me. It felt good. I rubbed myself as I pushed it deeper into me. I changed positions and sat down on the dildo…working myself up and down on it as I pinched my nipples and tugged at my cock. I flattened myself down onto the dildo it was deepest I’d ever gone. I felt it stretching me. I wanted it all the way in. I stood up with the dildo still in my ass. I grabbed a chair from the kitchen and sat down slowly. I flinched a few times, because of pain but finally was able to sit down all the way. My back was straight, my ass pushed out the back a little as I released a large amount of cum. It squirted beyond the towel I laid out hitting the TV screen. I stood up off the chair coaxing the last bit of cum out of me as my ass pushed the dildo slowly out of me. The dildo plopped onto the chair. My legs were quivering as I struggled to stay up. I straddled to.
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