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Holding my legs up against himself, Gary pushed. I felt pressure, and realized I was clenching my asshole in anticipation. I breathed out, and relaxed my ass. His cock shot halfway in at the sudden relaxing of my hole. He looked at me “You Okay?”. He looked concerned. “Yes, no problem, keep going.” I felt no pain at all, just a bit of pressure. Not long after, I felt Gary’s bush tickling my smooth bottom. He was all the way in. Gary looked me in the eyes, I looked back, and nodded my head up and down, he began to withdraw that beautiful cock. I was thinking, this seemed pretty nice. No pain, felt okay, we can do this.Gary continued thrusting in and out of my ass, picking up a little speed, but staying at a constant pace. I was still feeling no discomfort, which I guess surprised me. Apparently, those sessions of fucking myself had paid off. After maybe 5 or 10 minutes of fucking my ass, Gary seemed to be tiring of holding me up off the bed. “Gary, put me down.” He lowered me, pulling. I was glad that it was you on that bench last night crying. Wait... that didn't come out right." It's ok I know what you mean," she replied with a giggle. We sat there just looking into each other's eyes and if she was ready or not, I was going to kiss her. I wanted it to be as perfect as possible so I thought for a minute about exactly what I would do. She knew what was coming because she was biting her lip in anticipation but still had no idea when it was coming. So I put my hand under her chin with my index finger on her chin and softly pulled her head up a bit. I leaned in slowly and closed my eyes and the next thing I knew my lips grabbed hers and we had our first kiss. It was my first ever kiss so I wasn't exactly sure what I was doing so I just tried to do it like they did in the movies. I put her upper lip in between mine and began massaging it. I backed away pulling her lip back a bit in the process. "I'm sorry. I just thought we had something. I..."She was smiling and.
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