Anal first time - Sex Stories

Anal first time

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 ...