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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).

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“Good girl, sissy! I knew you had it in you! And now, you're about to really have it in you!” She laughed at her own joke, and started to push. True to her word, at least she went slow. I gasped and moaned, feeling the huge, hot weight of her gradually stretching me open, relentlessly forcing her way inside. She grabbed hold of me, one arm wrapping tightly around my leg, her other reaching around to grasp my dick. She wasn't stroking me anymore, not intentionally, but as she began slowly thrusting in and out of my ass, working her way deeper, the effect was the same. It took her maybe five minutes or so to finish getting all the way in, pressing hard against my ass, grinding to make sure I was feeling every last inch she had to give.