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When I Was A Kid
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Straight Male / 29
Young Boy Experimenting Pt.2
Yes this is a continuance of a true part of my life... I previously posted this story but not to full extent, not as in depth and I had gotten my age wrong. I was actually a year younger then I had thought I was because I was only in 4th grade.
After a few times of using golf balls as my way of experimenting and exploring my curiosity of putting things in my butt, I found something new. One day around the beginning or maybe middle of 4th grade, I was being snoopy and was searching through my parents room, for what reason I dont know. I searched through there closet and dresser and found nothing of interest and was about to leave there room when I had the thought to check under there bed. When I looked under, right there was a huge double sided dildo. It was purple and translucent. I was about 4'5" maybe 4'6" and was slightly tall for my age. This dildo was so long when I held it, it went from the ground to the middle of my thigh at most, so I'm guessing about 20 or 22 inches long. It was huge! It seemed way thicker than the golf balls were but not as thick as a soda can. If I had to guess about 2 inches in diameter or very close to that. The heads on it were flared and were bigger than the rest of the shaft by about a quarter of an inch.. Instantly I wanted to see if I could fit it in my young little butthole. I went to the kitchen and grabbed some olive oil and went back to my parents room. I started jacking off my little cock to prepare myself. My parents room had a sliding doors closet and it was just two giant mirrors. I lubed up one side of the dildo to about half way down the shaft, got on my knees and hands and started to push it against my hole. It was super hard to make it even start to go in because it was such a big tip. When I finally was starting to get barely a third of the head in and was still struggling to get a hard enough push I decided to lay my face and chest on the ground while still on my knees and use both hands to be able to get a better grip on this monster dildo and be able to push harder. The first push made the head slide in to about half way, then i let up and tried again. This time I pushed even harder. The whole head went in me and it was painful when the last part of the head popped in me fully. I remember the big pop feeling it made. After that I had to take a minute to catch my breath amd stop my self from almost tearing up. Once I recovered from that pain it felt nice still sitting in my ass. I started to jerk off my harder than ever pecker then layed back on my face and chest and slowly started to push more in. I would push in about an inch and slide it back to where just the head was in me again which the flare of the head made it stay in my ass, do that a few times, then I would push it in another inch or so and repeat the process until I couldn't fit anymore in. If I had to guess I probably fit about 5 maybe 5.25 inches into my 9 year old hole. Once I couldn't fit more in I slid it in and out, first slowly then faster for about twenty minutes, taking breaks in between with it fully inside me to jack off. It felt kinda painful but in a good way. I felt like I had accomplished a challenge I was questioning if I was going to be able to beat. After I was finished I had to pull the dildo out. All was fine until the flared head which like I said would stop and not slide out. It was bigger than my little ring amd since it was the back of the head it was the most flared part with no taper really. I slowly pulled on it and had to use more strength than I had to sliding out the shaft. Finally the flared back of the head popped out and the rest of the head slid out fast due to being shaped like a real penis. When it finally popped out it hurt just as much as when I put it in and along with how fast it slid out the rest of the head it kind of made it hurt even more. This thing took the breath out of me once again and I felt like it might have damaged me coming out so fast... once it was out and I recovered, I washed it off in the bathroom and put it back under my parents bed. I checked my butthole which was stretched out and there was some blood. Luckily it was not a lot of blood, left only a few decent sized drops on the tp i wiped with and with a few wipes it had stopped. It took me a while to build up the courage to use it again, but I used it quite a few more times. Every time was just as painful as the first time and just as pleasurable. My little asshole would always shrink back to where just one of my fingers would fit snuggly and back to its regular tight self. I wish I could find a dildo now that would give me that feeling of that monster in my little body then. I cant find a dildo that has as big of a flared head. i have a 7" usable length by 1.8" diameter dildo now, the length is fine but isn't thick enough + the head isn't flared as much . Thinking of finding one around 2" to 2.1" diameter and maybe that will be enough to get that feeling again.
After a few times of using golf balls as my way of experimenting and exploring my curiosity of putting things in my butt, I found something new. One day around the beginning or maybe middle of 4th grade, I was being snoopy and was searching through my parents room, for what reason I dont know. I searched through there closet and dresser and found nothing of interest and was about to leave there room when I had the thought to check under there bed. When I looked under, right there was a huge double sided dildo. It was purple and translucent. I was about 4'5" maybe 4'6" and was slightly tall for my age. This dildo was so long when I held it, it went from the ground to the middle of my thigh at most, so I'm guessing about 20 or 22 inches long. It was huge! It seemed way thicker than the golf balls were but not as thick as a soda can. If I had to guess about 2 inches in diameter or very close to that. The heads on it were flared and were bigger than the rest of the shaft by about a quarter of an inch.. Instantly I wanted to see if I could fit it in my young little butthole. I went to the kitchen and grabbed some olive oil and went back to my parents room. I started jacking off my little cock to prepare myself. My parents room had a sliding doors closet and it was just two giant mirrors. I lubed up one side of the dildo to about half way down the shaft, got on my knees and hands and started to push it against my hole. It was super hard to make it even start to go in because it was such a big tip. When I finally was starting to get barely a third of the head in and was still struggling to get a hard enough push I decided to lay my face and chest on the ground while still on my knees and use both hands to be able to get a better grip on this monster dildo and be able to push harder. The first push made the head slide in to about half way, then i let up and tried again. This time I pushed even harder. The whole head went in me and it was painful when the last part of the head popped in me fully. I remember the big pop feeling it made. After that I had to take a minute to catch my breath amd stop my self from almost tearing up. Once I recovered from that pain it felt nice still sitting in my ass. I started to jerk off my harder than ever pecker then layed back on my face and chest and slowly started to push more in. I would push in about an inch and slide it back to where just the head was in me again which the flare of the head made it stay in my ass, do that a few times, then I would push it in another inch or so and repeat the process until I couldn't fit anymore in. If I had to guess I probably fit about 5 maybe 5.25 inches into my 9 year old hole. Once I couldn't fit more in I slid it in and out, first slowly then faster for about twenty minutes, taking breaks in between with it fully inside me to jack off. It felt kinda painful but in a good way. I felt like I had accomplished a challenge I was questioning if I was going to be able to beat. After I was finished I had to pull the dildo out. All was fine until the flared head which like I said would stop and not slide out. It was bigger than my little ring amd since it was the back of the head it was the most flared part with no taper really. I slowly pulled on it and had to use more strength than I had to sliding out the shaft. Finally the flared back of the head popped out and the rest of the head slid out fast due to being shaped like a real penis. When it finally popped out it hurt just as much as when I put it in and along with how fast it slid out the rest of the head it kind of made it hurt even more. This thing took the breath out of me once again and I felt like it might have damaged me coming out so fast... once it was out and I recovered, I washed it off in the bathroom and put it back under my parents bed. I checked my butthole which was stretched out and there was some blood. Luckily it was not a lot of blood, left only a few decent sized drops on the tp i wiped with and with a few wipes it had stopped. It took me a while to build up the courage to use it again, but I used it quite a few more times. Every time was just as painful as the first time and just as pleasurable. My little asshole would always shrink back to where just one of my fingers would fit snuggly and back to its regular tight self. I wish I could find a dildo now that would give me that feeling of that monster in my little body then. I cant find a dildo that has as big of a flared head. i have a 7" usable length by 1.8" diameter dildo now, the length is fine but isn't thick enough + the head isn't flared as much . Thinking of finding one around 2" to 2.1" diameter and maybe that will be enough to get that feeling again.
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