Looking over my shoulder when he’d stopped, I saw him take some lube and smear it over his swollen member, before taking two coated fingers, and ins...rting them gently in my ass.Groaning I lifted my hips up, still keeping my head on the bed, as he thrust them deeper making me gasp with pain as he pushed past my sphincter.“It’ll be okay…” he reassured me removing his fingers and guiding his shining, slippery cock between my cheeks until its head was pressing against my asshole.“I’m not sure if……”. I stayed popular – first in prep school and now in college – by being everything to everyone in the popular crowd and by intimidating the unpopular crowd. Whoever I was with or whoever I wanted something from next was who I focused on pleasing.“I’ve thought about things a lot after we talked on Thursday. I realize I’m still trying to be all things to everyone. I know Tiffany and Molly want to do wild things and try stuff they’ve missed out. I’m trying to be that person for them. I know Katelyn. More

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