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This evening I was not sure I wanted her by the window. I was not in the most flattering condition. She was there of course.When she saw me she gave me a small smile and a shake of the head as if to say, “you are nuts”. She left the window before I could nod in agreement.My body was telling me she was right. But my heart had a second picture of her and knew I would continue. Her smile could light up the sky. She was beautiful.Running past her window became the highlight of my day. I ran everyday. She was accomplishing more than any amount of will power or trainer could have. I began to make physical progress. Running became easier.I had done some snooping and found out that her name was Debby. She was a teacher and much to my delight, single.I would see her at the window only two or three times a week. Sometimes she would appear to take notice of my passing but most of the time she would not.My heart was telling me she knew when I was there. My mind disagreed.About the fourth week of. I felt myself resisting, then releasing, relaxing with her massage. She tugged a little farther and I let her stretch my tight spincter. It was weird, but it felt sexual and vulnerable too. What was happening to me?"Still feel good?" she inquired.I nodded. As if my rock hard cock didn't tell her."Good. Now, I'm going to pop your cherry." You are?" Stupid question."I am. Focus on relaxing. Relax your body. Focus on the feeling." I tried, but part of me was still resisting.She withdrew her wet finger and applied another drop of lube. By now I was enjoying the sensation of being "wet"- almost like her pussy, I thought. Is this how girls feel? Wow, I thought, if I was going to say anything... if I was going to stop... this would be the time. But I didn't.Meg dobbed the lube at my entrance and pushed her moistened finger back in to the first knuckle. She met the back spincter but, instead of stopping, she pushed slowly but insistently. After only a second, she pushed past the resistance.
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