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I stood up straight and moved closer. Carol’s legs were pointing straight up, the green stiletto heels by my ears, pointing towards the ceiling. Carol reached between her legs and placed my cock at the entrance to her pussy. “Push! Just push it in!” We were watching each other’s faces to see the reaction—me reacting to my first pussy, her reacting to having her pussy stretched. Truthfully, my cock is pretty average length, six inches on a good day. But I have since learned it is pretty thick. Carol’s eyes widened at I entered her, my balls slapping against her taint. I didn’t see any more reaction as I closed my eyes as I felt my dick swallowed by warm wet tight pussy for the very first time. If I hadn’t cum an hour earlier, I would have blown my load right then on the first stroke (as I did with more than a couple girlfriends soon after).

She’d snuck into her parent’s bed a few times over the years, something she hadn’t grown out of since her childhood. But to her credit it always got her a good night’s sleep after a bad dream. After she hit puberty, she’d been told she had to go back to her own bed, but after giving her dad a sulking pout she was always allowed to stay until she calmed down.

Guy Humping Pillow: A meme referencing exaggerated or humorous portrayals of loneliness, often used in internet culture to mock obsessive anime fans.