She stroked his cock slowly but with purpose as she kept pressure on the toy going into his tight ass hole. She knew from experience that the first ti...e was going to be difficult and painful but she also knew the pleasure that the anal penetration could bring, especially to a man. The toy was almost in him, he only had to take in the wider part and then he could start to really enjoy himself. "Connor baby, it's going to be a bit more painful now, but I'll do it quickly, so just hold on and. I find you attractive and very knowledgeable.” I see a look on her face that tells me she is listening. I go on, “You look like someone who could teach some young man, like me, how to pleasure a woman. I am willing to do whatever you say in order to give you pleasure, if you are willing to teach.” Her friends arrive and I get up to leave. I make it about three feet. She says, “Turn around.” I turn and watch her talk to her friends. I could not hear what was being said. She asks,. More

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