It had to be around when I was 13-14 years old, I was mostly influenced by porn.
It was the time when affordable broadband internet became widely available for the big public and I could finally download some real movies instead of tiny low quality clips from Napster or Kazaa. It was the teen time of porn as I call it, every movie was obsessed with their actresses having just turned 18 and it seemed like every good looking young girl got their own non nude model site with Tiffany Teen as their role model. Either way, I got most of my porn fix from one of those sites that update every day with preview galleries, which were mostly pictures or small clips of such teen models, lesbians, the occasional sex scene and rarely anal. To me anal was something dirty which was only done by filthy rednecks and homosexuals because they had no other choice.
I didn't understand why the girls would allow that nor did I understand why guys would want it when they had a pussy they could fuck instead. Then one pornstar came along that changed everything for me, Gauge. It was like a clash of two different worlds, she looked like she belonged on one of those non nude model sites, petite, cute, innocent face, but instead she did hardcore porn with anal. I was intrigued, it drove me wild how someone as innocent looking as that could do such nasty stuff and I loved it. I searched for as much of her stuff I could find and started looking for anal in general, then I realised that people actually enjoyed it, seeing the girls go crazy made me wonder how it felt and one night I decided to try it myself.
I still remember that first time like it was yesterday, parents asleep in the next room, lying in bed fantasizing about the porn I watched earlier. Without thinking too much about it, I quickly grabbed a thin marker from my desk, got back in bed and pushed it in. It hurt like hell, I almost screamed, took it out, threw it in the bin and I thought that was the end of that. But I kept watching the porn and during horny moments in the months following I kept trying, making one mistake after another, too fast, too hard, using soap as lube, ... Until I started using the handle of a screwdriver under the shower which was the first time it actually felt good. I bought several more screwdrivers as toys and kept doing that for years, eventually used more household objects until I finally bought some real toys 2 years ago.
