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I laid on the bed on my stomach and she helped me put a pillow under my hips. She started by inserting a cotton swab with Vaseline into me so I could get used to something going in. After 2-3 insertions of the cotton swab, she changed to a pencil wrapped in a condom. This did not bother me at all, actually it was pleasurable. Then she put on a disposable glove and slowly inserted her middle finger, the feeling of my asshole being penetrated like this was odd, but I was getting turned on. Slowly she moved her finger in and out, in and out. Many times she would rotate her finger around. I started breathing heavily and could feel myself getting very wet. She told me that she felt I was ready for something bigger, her 6 1/2 inch strap-on, I took a deep breath and told her to go ahead. She put some lube on the strap-on and around my asshole. She told me that when I feel her pushing in to push out and the head will go in smoother.I felt the head push against me and I pushed out and the head. . a... I was skipping school that day. I got fed up with studies and needed some free time like any teenager. So during lunch I simply skipped out the back door and walked home. Luckily home isn't that far away and in no time I'd be there relaxing by myself, free from the boredom of classes and stupid teachers. Who knows what useless thing I might have been doing had I not seen the car in the driveway. Perhaps I would have wasted it watching TV or something. But turns out I was soon going to be watching something a whole lot more interesting.The car in the drive way was my mom's. Of course this was very unusual since she was supposed to be at work. I was instantly pissed off upon seeing it there. My naive little mind thinking she must have been sick or something. No matter the reason, my mind only thought was "How the hell was I supposed to skip school with her around?"Basically I was left with two choices, run back to school and beg the security to let me back in, or open that front.
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