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He finishes and start to rub the lube on my hole, he does this till his finger slides into my butt. I wince as his finger enters me unexpectedly, he keeps it in for a little bit and pulls it out and starts massaging again but with two fingers this time. He repeats his action as he did the first time and pulls his fingers out of my bum.Jacob then tells me "Okay Derek, get ready I'm going to pop your cherry now. Just breath slowly and dont move ill do the moving kay.". "Okay Jacob, do you promise it wont hurt?" I say one more time, " Yes, I told you it wont hurt that much Derek" Mark says for him as he's sitting next to us on the bed rubbing himself slowly. Jacob grabs the lube and lubes the condom up once more before aiming it towards my hole. He places it next my bum and slowly starts to push it in, it hurts alot almost burningJacob tells me to breath and relax. The head of his penis is pushing into me and slowly start going inside my bum. He pushes a little more till finally it. .” she thought, squirming on a chair that was clearly designed to keep distracted undergrads awake during lectures, rather than help an exhausted grad student catch a well-deserved catnap in the middle of the goddamned night. Her wrist brushed her nipple, and again she thought about how long it had been… “Dammit!” she snarled again. Sitting up, she realized that her mind was simply not going to let her sleep; she was too keyed up from coffee, worry, and—now—irritation and frustration. Clearly, it was time to go home, drink some Sleepytime tea, and try to get some sleep in a proper bed. She stood up, shrugging off her jacket onto the chair so she could gather her possessions. The movement of shrugging off the jacket brought a sharp, clear moment of body memory. Early in her relationship with Nick, they'd gone out to a moderately fancy restaurant and been caught in the rain walking back. Her top had been soaked through, and he had draped his jacket over her shoulders in a gentlemanly.
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