Curious George

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Introduction:
My first time masturbating with a dildo. If your not into solo male anal play, don’t read please!

When I was a boy, maybe around 14 or 15, I found a book under my parents bed while snooping around. The book was of all sorts of erotic stories, and I found myself loving the book. I masturbated frequently, as any young man does, and this book became one of my favorite things to masturbate too. I could only use the book while my parents weren’t home, being that I had to go into their room to get it, and I feared being found looking for the book under their bed. After a few weeks, I had finished all of the stories, and read through them all a couple of times. When my parents were out for the day, my mom shopping and my dad at work, I made my way into their room, and got on my knees next to the bed. I found the book, and moved some stuff around to see if maybe I could find another. I found a shoe box, non-descript, just sitting there, so I pulled it out. I opened the lid and found, to my surprise, 2 dildos, one slender and green, and a white one with much more girth. Along with the dildo’s I found some lube, massage oil, and a little pink vibrator on a long cord. I had never seen a dildo in person before, I had seen them on the internet, or in porn videos, but never in person. I picked the green one out of the box and held it in both hands. It was about 7 inches long, and about as thick as a broomstick. I had never had gay fantasies before, or any gay thoughts, but when I held this dildo in my hand, my mind began to race. I thought of what it would feel like in my butt, and if it would hurt. I wondered if I would like it, and if liking it would make me gay. I put my doubts aside and decided to try my luck with the dildo. I took the dildo and the lube into the bathroom, where I locked and bolted the door shut. I peeked out the window overlooking our driveway to make sure no one was home then sat on the toilet.

Being young, and new to anal play, I didn’t know how to begin. I made myself go to the bathroom, for fear of making a mess on the bathroom floor. When I was done, I cleaned up and got on the floor. I took out the lube and squirted a glob onto the tip of the dildo, then rubbed the lube all over the length of the toy. I bent over, on my knees, one hand on the floor, and one hand guiding the dildo to my butt. I pushed the dildo against my whole and pushed, but I had trouble getting it to penetrate. The dildo simply wouldn’t slide through my virgin hole. I straightened back up and took out the lube again, this time rubbing it on my pointer finger. I bent back over and this time guided just my hand back to my butt, allowing my finger to rub on the outside of my whole. I felt the cool lube smearing across my hole, and then an odd sensation as a inserted my pointer finger into my hole. It felt odd, both feeling my insides with my finger, and feeling something moving around in my anus. It didn’t hurt, it just felt weird. I gently fingered my hole for a little while longer, before picking up the dildo once again.

I placed the dildo against my hole again, and this time, felt the odd sensation of my asshole being pulled apart as the toy slid inside more easily than before. The lube around my hole eased the dildo in easily, and my ass willingly accepted the intruder. It felt amazing, this simulated dick sliding into my ass, filling up my insides. The dildo was thin, so it really didn’t hurt at all, uncomfortable, a little, but no pain. I began to slowly move the dildo back and forth in my ass, feeling it slide along my insides, and pull on the rim of my asshole every time it slid back in. I found myself wanting more after a little while, I found myself wanting something bigger inside of me. As the thought entered my head, I found myself walking back into my parents room, and next thing I know, the big white dildo is in my hands.

I knelt down again and lubed up the white dildo. On my knees, I rubbed the toy against my whole, before pushing it in. This feeling was a little more intense than the feeling of the green dildo in my butt. This one hurt, it hurt bad. I felt spasms of pain roll through my body from my rectum. I pulled the dildo out and started to breathe heavily, my butt still hurting. Determined, I tried again, this time, the pain a little less, but still enough to make me pull the dildo back out. This went on for a few minutes, me pushing the dildo in, feeling the pain, then pulling it back out, until finally, I could take the pain, and left the dildo in. After awhile, it felt glorious, the dildo penetrating me deeper than before. I pushed in as far as I could, until it seemed as if I would lose the dildo, then pull it back out, sometimes letting it come all the way out just so I could feel it dive into my ass fresh. I looked down at my dick and saw it dripping pre-cum. I really couldn’t rub my cock with my hand working on my ass, so I stood up, holding the dildo in tight with one hand. I put the toilet seat down and sat on top of it, dildo still deep inside of me.

I stood up slightly and sat down again, fucking myself with the dildo but leaving my hands free. “This is what it was like to get fucked by a guy,” I thought to myself. It felt so good, the dildo pleasuring me in ways I didn’t know possible. I quickened my pace, really fucking the dildo as I began to rub my dick. It felt so good, the combination of my ass getting penetrated and my hand rubbing my cock. I felt my orgasm coming a few seconds after I started rubbing my cock. I came in big globs of white, right into my waiting free hand. My hand was filled up quickly, an some dripped over and landed on my feet and the rug. I looked at the cum, feeling very adventurous (I just fucked my own ass after all) and decided, why the hell not. I brought my hand to my face, and sucked in, taking all the cum in my mouth. I coughed once, forcing some of the cum out, and down my chin. It tasted salty, a very odd taste, but not entirely bad. I tried to swallow but it felt like the cum was stuck in my throat. I kept swallowing until there was only a lingering feeling of the semen. I stood up, almost forgetting the dildo in my ass. It fell out with a sucking noise and hit the floor. I cleaned up, and went to my room. The after affects of everything left me a little sore, and my throat a little sticky, but I could tell that this was only the beginning of a whole new world of sex for me.

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