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I hadn't expected to hear this from her and I really didn't know what to say, so I simply took her hand in both of mine and held it tightly. Her eyes glistened as she held back her tears. "I'm in," was all I said and she smiled. It went on like that for three more weeks, with me walking her to the car and sharing a deep, passionate kiss with her. As we went on, I caressed her body as we kissed, feeling her taut breasts and her sumptuous ass. It never went further, and I didn't push her to go further. Just about every Friday night I would call her and we enjoyed the sounds of our voices. One Wednesday night as I kissed her goodnight she asked me to get in the car with her. As we sat in the front seat making out, she reached between my legs and found my erect cock. I tensed up, not quite ready for this bold move on her part. "Relax," she said. "Don't you think it's about time we went a little further?" I mumbled a reply as she felt my cock through my pants. Her hands traced the outline. His best friend, David Chaney had introduced Michael to the pleasures of anal penetration. It had started one afternoon when they were playing on David’s Xbox. “Hey Mike, have you ever tried sticking something in your ass when you jack off?”“No have you?”“yeah. It’s real cool. It makes me cum real good. In fact I’ve even made myself cum without stroking my cock, just by fucking my ass with something.”“So what do you stick in it then?”“My mom’s dildo.” Michael thought of the lovely Mrs Chaney, so pretty, so demure. He could not imagine her using a dildo. He started to wonder if his own mom used one.“I don’t think my mom uses one so I couldn’t do that.”“I bet you $5 that she has one. All women do. It’s a well known fact. Anyway you’d be better trying it with something smaller to start with, until your ass gets used to it.”Michael took David’s advice the very next night. He went to bed early, sneaking a candle from the emergency stash in case of a power cut. Michael’s heart was beating.
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