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I asked who would be my “babysitter” and mom told me Diana. What? The 23 year old dike from down the street? (I thought to myself). Wonderful. Diana recently graduated from college, stood about 5’8” and about 160lbs—she was not very attractive, but was very athletic. She played softball and basketball for the local college.Diana showed up late Sunday afternoon, and was quickly becoming a nuisance by dinner. I retired to my room for late homework studies…and to get ready for Diana to come to bed. My parents took the suitcase that was positioned behind the door—so my vent was clear for viewing. My wait was long—but in the end, it was worth it. Diana finally came to bed around 11, and was quickly out of her clothes before I could get to my vantage point. When I peeked through the vent she was already sitting at the vanity naked—her boobs were much bigger than my mom’s (turns out they were 36D), and her nipple was turned to the side, almost pointing at the wall! I could not. I get the idea that she’s really interested, but she’s in 8th grade and I think she might be a bit intimidated by Jennifer, you, and the other girls I hang out with. I flirt with her a little bit, and she eats lunch with us every day. I think she’d be a lot of fun, but I don’t want to hurt her.“There’s also Mary, on the chess team, also 8th grade. She asked me to practice chess with her, but I didn’t get any vibes about anything other than just chess. There’s Elizabeth and Michelle.”She stopped me.“Cross Elizabeth off your list. She’s basically gone off the deep end and seems to be working her way through the entire Senior class at her school. She hasn’t mentioned you at all. No loss, in my opinion. Michelle is a different story. She’s too far away for anything even occasionally like we have. And while she really, really enjoyed it with you, and would probably do it again, she knows that you are ‘spoken for’ in a serious way and I don’t think she’s ready to sign up to be a regular.
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