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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).

“We’re going to need some of this,” she said, unscrewing the cap. “Lubrication,” she said with a smile, seeing the confused look on my face. She poured a generous handful of oil and slathered it onto my shaft and my balls. She spied the label as she set the bottle down. “Hmm…extra virgin. That’s the only thing in this house tonight that is virgin anything.” I laughed nervously. I remember now my clueless mom never figured out why her bottle of olive oil kept appearing in my bathroom.

“Please?” Carol asked again before I could say something. “I never thought of being assfucked, but you just made me feel so good, I want to feel you cum in my ass. Please? Before I change my mind?”