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It was frustrating being on the other side of the country when my girlfriend lived in Arizona and went to another college. I tried as hard as I could to keep our sexual intimacy up but it still wasn’t as good as I wanted it to be. I was almost out of school for the summer and all I wanted to do was be with my girlfriend so we could have sex again. I felt like I planned out us having sex more then we actually did it. I also felt like I wanted it more then she did. I often tried to bring up sexual topics between us and she would respond barely and then drop it or change the subject. This was frustrating to me, I knew other guys girlfriends were a lot more sexually driven then mine. I wanted to do something special for her when I got back home so I tried to plan something sexual. When I flew back to Arizona I drove to see her immediately because I couldn’t wait to see her. I planned on asking her to marry me as soon as I got out of school the following year. When I got to. After a couple minutes, I pulled my hand back and felt Mr. Phillips let his cock rest between my ass cheeks. It was so warm and his big hair balls were in contrast to my smooth little sissy nuts. Reaching for my mom’s baby oil next to the bed, he drizzled my little asshole like a pastry until my young rosebud and ass crack were saturated. He returned back on top of me, and this time I felt his old cock touch my tight little butthole. At first, he just “knocked” at the entrance didn't enter me. But he pushed harder, and I felt my virgin sissy pussy stretch. As his cock pushed inside further inside untouched territory, the stretching started to hurt. I involuntarily pulled away, but he kept saying its okay and to relax. I just grabbed the pillow at the top of the bed, barked into it. He continued pushing it in, very slowly but gently and he asked if I wanted him to stop; each time I shook my head no. He did it so slowly that when the head finally entered me, it felt good but somewhat.
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