I looked over at her with her fisted hands and tears running down her red face. I didn’t know what to say. I didn’t know what to do. The feelings that I felt for her went beyond her outside appearance. She was my wicked smart friend. Yeah, I knew she was overweight, but I never saw her as an ugly person that I wouldn’t want to be around. She was fun, funny, and so very wicked smart. She made me smarter just talking to her and being with her. I couldn’t imagine not having her in my life. ‘Why don’t we go to the prom together?’ She looked up at me, blew her nose, and smiled. ‘Go ask a cheerleader. You don’t want to be seen at the prom with me. You’ll never hear the end of it. All your friends will laugh at you.’ ‘I can’t think of anyone else who I would have more fun than you. Besides, my real friends wouldn’t laugh at me for going to the prom with my best friend.’ We went to the prom and the closeness of slow dancing advanced to a first date, a first kiss, and our first sexual. From having sex outdoors at home or on vacation to inviting Melanie and Mary over for an occasional foursome, I could not have asked for anything more.We also settled into a nice routine where every morning Sherry would wake up to me jacking off and we’d masturbate together. Sometimes I’d oil up her ass and enjoy rubbing my cock between her ass cheeks for extended periods of time before my cum would explode up her back. Sometimes I’d slip my cock into her tight ass and fill her with cum. I never lost my desire for her youthful body and would have sex with her throughout each day as soon as I recovered. That usually meant getting off five times or more every day. Sometimes it would be long sessions where I fucked every orifice. Other times I’d just have her jack me off or give me a quick blow job. That went both ways and as I got older when it took me longer to recover Sherry would climb on top of me while I was sitting in my chair and sit on my face while I licked her pussy.
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