My very first time fucking was raw. I had sucked a couple cocks before and I loved swallowing loads. One day I was talking to this guy on Grindr. He was in his 40s and I was in my early 20s. He asked if he could fuck me and I decided I was ready so I said yes. He asked where I wanted him to cum and I said in my mouth, but he asked if he could cum in my ass. I thought about it for a minute and how I had been told to use condoms, but I didn't think it would be that big a deal if I got fucked raw just the first time, so I said yes. We met up and he was an incredible kisser and he took his time loosening me up before he shot a hot load in my ass. It felt so good that I was shaking. Then he jerked me off and I shot a huge load all over myself. We talked for a few minutes and then I sucked him until he shot a second load in my mouth.
It was an incredible first fuck, but I told myself I should be more careful and use condoms in the future. Cut to a couple weeks later when I had the chance to top a different guy. I brought condoms and planned on wrapping up, but he backed up on my raw dick before I could react. I forgot my plan and instantly started pounding his raw ass. Unfortunately I had enough restraint to pull out and shoot on his chest. He seemed really disappointed.
After that though it was almost impossible for me to commit to playing safe. I quickly stopped mentioning condoms and I realized most guys didn't use them either. I've only played safe a handful of times, at the other guy's request. And I've made up plenty for not breeding that first guy's ass.