*This is a true story*
It started years beforehand. Chatting with a girl from MySpace who was a bit kinkier than I was. I hadn’t even thought about doing anything with guys, or even playing with my ass. But while chatting with her, she brought it up. It sounded kinda hot, so during phone sex, I started playing a little. I liked it, a lot. We chatted a few more times, she brought up the idea of an MMF threesome, to which I wasn’t interested at the time. She was ok with that, and we proceeded to have occasional sexting/phone sex conversations.
Finally we decided to meet up. During a blowjob she slipped a finger in my ass. Feeling her suck my cock and finger my ass was amazing! It was the best BJ I had ever gotten. I came hard and she swallowed all of it. The experience left me wanting to try a bit more.
Fast forward a few years.