A curious guy learns the hard way what its like to lose your anal virginity
*Warning* this story includes sexual interactions between adolescents. I do not condone this behavior. This is based on true events.
I’ll start with a bit of background. I was born in the 80’s, a time before the internet. I had a normal upbringing, nothing out of the ordinary. I have an older brother (I won’t include names). He was 3 and a half years older. Ever since I was a child, I liked “playing” with myself. I was a very curious kid. I legitimately thought I invented masturbation. One of my earliest memories is of me taking a bath and while the water was filling the tub I would stick my penis under the waterspout because it made me feel good. I was kindergarten age. Around this age, I also had a fascination with sticking pencils in my butt; I did it because it felt good… I had no idea why I did these things, like I said I had a normal upbringing. To my knowledge, I was never abused as a kid.
My story starts when I was in third grade. Back then the internet wasn’t a thing. I had very little exposure to anything sexual. That all changed when a boy brought in one of his dad’s porno mags to school. When he showed a few of us guys my world changed. I was enthralled from the first page. The mag showed naked women and men. It also showed them doing everything from giving/getting blowjobs to fucking!
People say that the current generation is too sexualized, but I’ve found the old saying “there is nothing new under the sun” to be true. I remember even back then girls and guys talking about the stuff they would do with each other. The girls talking about giving blowjobs. It wasn’t until I saw the porno that the context finally sunk in. After that day, I kept asking the boy if I could see it again and again. He finally just let me have the porno. I brought it home and showed my older brother. He just laughed and said he had a few of his own.
After that, things seemed normal for a while. I learned what masturbation was (and that I didn’t invent it lol) and started masturbating any chance I got. One day out of the blue, I asked my brother if he would let me suck on his penis. I still remember how shocked he was when I asked him haha. Personally, I didn’t thing anything about it. I just wanted to act out some of the stuff I saw in the porno and since I didn’t know any girls that I could ask I figured why not ask my brother. After his shock wore off, he asked if I was serious. I said I was. He said that is kind of gay. I knew the word but didn’t think much of it. After thinking about it for a few seconds he said he would let me if I never told anyone about it. I agreed right away. He said let’s wait till night, after our parents went to sleep.
That night I remember how nervous he was, he was kind of trembling once I came into his room. He asked again if I was sure I wanted to do it. I told him I was. He laid back on his bed and pushed his underwear down. I remember how big his penis looked to me. My penis was so much smaller by comparison. I couldn’t take my eyes off it. He didn’t have ask me to do anything. I climbed on his bed brought my face right up to it. I reached out with my hand and wrapped it around the head. My hand could barely wrap around it, it’s likely that my hand was just small. His penis had a large purple-like head. I just stroked it a few times. My brother looked like he was holding his breath, probably too scared to say anything and break the spell. I can only imagine how he must have thought he was the luckiest guy!
After stroking him a few times I wasted no time and brought the head of his penis to my mouth. I licked the head like a lollipop a few times. It didn’t taste bad, I bet he took a bath before I arrived. After licking the head, I put it in my mouth. I sucked on it like a vacuum cleaner, that’s what I thought sucking meant…lol. My brother didn’t seem to mind it. A few times my teeth kind of bit into his penis and he let me know not to do that because it hurt him. I tried my best not to do it again but I’m sure I did it again. About a min after I started “sucking” his penis. He started to moan and tell me he was close. I had no idea what that meant. Suddenly, he tensed up and grabbed my head and held it still. I had only taken about two inches of his penis in my mouth so when he came it was all over my tongue. It was my turn to be shocked! I had no idea that a penis could cum. The porno never showed that part. After he was done cumming, I just sat there with a mouth full of cum.
After coming down from his orgasm my brother just looked at me confused. He asked, aren’t you going to swallow? I didn’t know you were supposed to swallow, so I swallowed. I remember I didn’t hate nor like the taste. I just took it as a part of the process. My brother was a bit shocked that I actually swallowed his cum. I thanked him for letting me suck his penis and left to go back to my room. I can only imagine what was going thru his head…like did that just happen.
For the next few weeks everything went back to normal, we didn’t talk about what had happened. Then about a month later my brother asked me if I wanted to “do it again”. I was more than eager to do it again, so I said yes. That night, once again I came into his room after our parents went to bed. He was already naked waiting for me. My starkest memories of those nights were just how much I liked looking at and touching a penis. We continued our little rendezvous for a few months.
There was one thing that I still wanted to do and that was to know what it felt like to have a penis inside of me. The girls in the porno’s seemed to like it a lot so it must feel great, right? Like I mentioned earlier, I have always liked playing with my butt. After getting the porno mag I started inserting larger items in my ass. The biggest thing I ended up inserting was a toothbrush. I remember it hurt a bit but felt good. Naturally, I figured a penis would feel good too…foreshadowing.
After a few months of sucking my brothers dick whenever he wanted, I never said no. He asked me again, this time I said I would do it if he would put his penis inside my butt. I think I broke his brain for a few seconds because he just stood there like he couldn’t believe what I just asked for. As I write this, I can see how my brother must have thought I was insane. Like, who it this kid?!? Who even asks for something like that? Well, I was that kid. I don’t know what else to say, I was super curious and had an unhealthy fascination with sexual acts.
Eventually, I convinced my brother. Yes, I had to convince him…he didn’t want to do it because he thought it was too gay. After convincing him, he said next time he was taking a bath he would let me know. A few days later he came and found me and said he was going to “take a bath”. After he left, I waited a few min and followed him to the bathroom. Mind you, I had no idea that normally when people decide to do anal, they prepare themselves. My naïve self just went for it. Once in the bathroom, my brother turned on the water so that our parents wouldn’t hear anything. He got fully naked and told me to do the same. He then asked me to suck his penis so that he could get hard. I got on my knees and sucked him till he got fully hard.
We got into the tub, he sat down and told me to hover over him, while facing away from him, like I was going to sit on his lap. I did as I was told and waited for my next instructions. He grabbed a shampoo bottle and poured it on his penis. He handed me the bottle and told me to put some on my asshole, I did. He then told me to slowly lower myself, I did. Once his penis hit my starfish it stopped. Once again, I have to remind the reader that I didn’t prepare for anal. His penis wouldn’t go in. The biggest thing that had gone up my hole was a toothbrush. Of course his penis wasn’t going to go in easily! We kept trying the gentle method for a few min but eventually he stopped and said he didn’t think it was going to work.
I was so disappointed! I was so looking forward to it. I suggested that he be more forceful; he ask if I was sure. I told him I didn’t know how else to get his penis inside of me, I should have stopped and thought maybe there is a reason for that…hindsight is 20/20. He said it might hurt…might, an understatement of the century. I told him I had already put items in my butt and it was fine. So, round two commenced. This time he put his hands around my waist and once his penis was at my hole and pushed down on my waist and thrust up with his penis.
It’s hard to describe the pain that shot thru my body once the head of his penis broke thru my anal ring…It hurt so much that I was in a state of shock. If I weren’t I would have screamed my lungs out. The problem was, I was facing away from my brother. So he couldn’t see the pain on my face, apart from my body tensing he that everything was okay. After the initial shock of shoving his penis into a warm and “welcoming” hole, my brother started moving his penis in and out about an inch each time. While I was questioning every decision I had made that lead me to this pain in the ass, my brother was having the time of his life. I’m convinced, if he could see how my pain I was in, he would have stopped. However, he couldn’t see it so he just built-up speed. Once my initial shock wore off I was so embarrassed to admit to him that I regrated wanting this that I just let him continue. To be fair, once my ass got somewhat used to his size it did feel a little good. It didn’t hurt that his penis was hitting my prostate. It only took him a min, definitely felt longer for me, to cum in my ass. Surprisingly, there was only a little blood on his penis once he pulled out. I’m sure his cum helped with that.
We washed up and before leaving the bathroom he told me how much he appreciated that I let him fuck my ass. I felt so proud that I could make him feel so good that I didn’t tell him how much it hurt. It took almost a week for my ass to stop hurting. Looking back, even with all the pain I can say I enjoyed it. I don’t regret it. I never asked him to fuck my ass again. Luckily, since he thought it was gay he never asked me to do it again. If he had asked, I believe I would have let him. I did suck his dick again, but we stopped once he hit 18 and was more interested in girls. We get along just fine as brothers, we just don’t talk about what happened when we were kids.