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Both Ways

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Both Ways by Ever since I started masturbating around 11, I've been a curious guy about my body. I've explored so many different ways to pleasure myself. When I was about 14, I tried fingering my anus. It was tough at first, but I would lube my fingers with spit or precum and pretty soon I had myself cumming harder and faster with a finger inside me. I also had a very active imagination (and still do!), so I would often imagine bizarre sex scenes and the like. Most of my masturbation happened at night after my parents had gone to bed. I would get on my floor and start humping it looking at a Victoria's Secret or something. This night was different though. I remembered my old stuffed animals and decided to try something new. I got out a thick, tapered marker and attached it to one of them. I licked it to lube it up and then slid it in my crack. WOW! I penetrated myself deep and I could feel my prostate throb against it as my cock started dripping precum right off. Not just little drips like it usually did but completely oozing. Then, I got a puppet out that was thick and furry. I massaged my cock for only a couple of seconds until it stiffened up and then I slid it inside the hand hole of the puppet. I backed against my bed on my hands and knees, pushing back into the stuffed animal penetrating me and then humping forward into the puppet's damp interior. Each way I felt a different intense burst of pleasure. It was all I could do not to moan as loud as I could. I literally felt my balls swell as my dick pounded inside this puppet and my rectum clenched around the marker. Soon the pressure was too much to bear, and indulging a little grunt, I let myself go, spewing hard into the puppet, permeating the fabric, all the while my anus convulsing on the marker. I've never done that since, but I will never forget that orgasm. --

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