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Jill didn’t look like a freshman. Besides being tall and having model looks, she might have the biggest, firmest breasts in school. She and Kate Upton were about the same size up top, and Jill was slimmer.I was afraid that if Jill and I went out, I might not be a good boy. That would just invite a shit-storm of trouble. I wouldn’t blame Phil if he never talked to me again, and Brook ... I didn’t even want to go there. Besides Kate Upton coming and telling me she’d made a huge mistake with that baseball dork, Jill was the only girl I might be tempted to cheat on Brook with. From the look Brook gave me, she knew it too.“Well, this just sucks,” Brook said when we were finally alone.“Yeah,” I admitted. “I was hoping we were done with this part of it.”“Don’t play dumb. What are we going to do about Destiny, Zoe, and Jill?”I noticed she threw in the ‘we.’“We could help you get enough signatures to win,” I suggested.“I’ll never catch them. Plus, they’re out there right now working to get. D.’s throbbing cock. On feeling it, I again started flailing, or rather tried to, doing everything I could to break free, but it was no use. Alex was too strong and heavy. I whimpered, as J.D. searched for my hole with the head of his penis. On finding it he said “Don’t worry Jason, gay boys like you enjoy this kind of thing.”What came next was something no boy can prepare for. J.D. began to push his Vaseline lubed penis inside of me. As he pushed I felt my tight hole stretch, and stretch until I thought I couldn’t take it. And I couldn’t. The pain hit me like a sharp knife cutting my insides as he slid inside me. I cried out to no avail, my eyes beginning to water and blur from the pain. “Please stop” I tried to yell, but what came out was a wordless, muffled scream. “Oh my fucking God,” cried J.D. “Alex, holy fuck this is good.” J.D. began to thrust. Gently at first, but it didn’t matter. The pain was excruciating, my ass had never been stretched like this before. .
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