This is a story about the first time that I had anal sex with my neighbour, named James. James was 1 year older than I was. From as far back as I can remember I always used to go around to his house on Saturday mornings and play computer games or go swimming in their pool.
James had a bedroom in the attic of their home, with a small on suite toilet and hand basin. There was good privacy up in his room, we always had a couple seconds to “get your pants on” as we could here as soon as anyone started walking up the attic stairs. We often used to give each other butt massages, and apply some attention to the ass hole during the massage process, from there we slowly progressed to masturbating in front of each other. We rather foolishly turned it into a game to see who could manage to blow their load first. I was always slightly envious of James as his cock was 8.5 inches when erect, and slightly bigger than my 8 inch member, his penis was also much thicker than mine and we were both circumcised.
One day when our parents were out he showed me a strip poker game that he managed to get hold of for the computer, the graphics were so terrible in those days that you could hardly be aroused by the images in the game, but it was the excitement of playing a sexual game that would get us turned on. We started playing strip poker and both ended up completely naked before we could get any clothes off the women in the game, after a few more attempts we finally managed to get one of the women naked. By this point we were both very horny and James explained that he had something cool to show to me, we went into the main bathroom of the house and he demonstrated a different way to masturbate with soap, using both hands and stroking only from the base of the penis to completely over the tip, alternating hands, like you are milking the penis. After a few minutes of great masturbation we both came hard in front of each other.
A few weeks passed, and we didn’t have much time alone to try anything sexual, but now that I had experienced masturbating with a lubricant I experimented with different substances at home to see which felt the best. It was then that I discovered petroleum jelly, at first I used it to lubricate my cock while jerking off, but I soon discovered that it was even better to lubricate fingers and brush handles to insert anally, I showed this to James the next time we were alone and we started to finger each other, this was something that both of us enjoyed giving and receiving.
As we became more and more comfortable with exploring each other, things naturally progressed to the next level with James suggesting that we try fucking each other, although we didnt have a clue what it was called at that age, we both wanted to try giving and receiving anal. As soon as we were alone again I suggested that he get the pot of petroleum jelly so that we can use it as a lubricant for our anal adventure.
James returned with the lube and proceeded to apply it to his already rock hard penis, as I rubbed some into my tight virgin anus in preparation for the pounding I was about to receive. I don’t have a clue why, but we decided to fuck in the tiny toilet off his bedroom. I was standing facing the hand basin, holding onto it for added support. James positioned himself behind me, in the restroom attendant sex position. I looked at James in the mirror and he asked if I was ready for him to put it in me. I reached back with both my hands and spread my ass cheeks apart, allowing him to slide in easier, indicating that I was ready. I soon realised, as he started to push it into my tight little hole, that I was far from ready to take his big cock. My ass hurt so much, like nothing I have ever experienced before. I tried to relax but it was nearly impossible. In hindsight it probably hurt so much and I couldn’t really relax because of the position we were using.
We paused for a moment to apply more lubricant before assuming the position again, this time it hurt a bit less. James let out a sensual moan as his cock started to enter my tight hole for the first time, I told him it was hurting too much but he kept on slowly pushing in, I thinking he only managed to get about 4 inches into me that first time, and then he started thrusting in and out gently opening my hole. Fortunately for me the head of his rock hard cock was rubbing perfectly against my prostate and soon this created so much pleasure that my cock became very hard.
James then started to fuck me at a steady pace. With every thrust I felt more and more pleasure and started to moan. I think my moaning spurred James on, as he started to moan too. It was still hurting a great deal, but the prostate stimulation was also feeling incredible at the same time. I stopped holding my ass cheeks open for him, used my left hand to support myself on the hand basin and started to play with my now throbbing hard penis, it was then that I noticed the huge amount of precum was leaking out for my cock, I used the precum as extra lubricant to sensually stroke my manhood.
After a few minutes of slow and painful anal sex he told me that he was going to cum in my ass. In those days neither of us knew what a condom was. We had already agreed beforehand that we both wanted our respective holes filled with the other’s hot cum. A few more strokes of my cock and I started to explode and shoot a huge load of cum into the hand basin and on the bathroom floor, shortly after I heard James grunt and thrust deep into my ass as he painted my rectum with his warm man seed, I feel spasm of his cock as it squirts his cum squirt into me. James finally stops cumming after several cumshots into my ass, and then stops moving.
We stood in this position with his softening penis still inside my ass, for a few minutes enjoying the afterglow of our first anal sex together, before he slowly pulled it out. I felt a little bit of cum sliding out of my ass, so I moved over to the toilet, sat down and pushed his cum out of my ass while he knelt down and watched it streaming out. James then washed himself off as I cleaned out my aching hole with some toilet paper. We then returned to his bedroom to recover before it was my turn to fuck his ass.
I cant really recall the details of me fucking him, only that he also experienced a lot of pain when I tried to enter him and we eventually stopped. This was the first of many anal sex sessions that I had with James, which continued for several years. He eventually was able to handle the pain and take my cock completely. Still to this day the sex with James was some of the best I have ever had, he is the only guy ever to fuck me bareback, we always fucked each other bareback and shot our loads into each other asses.