I usually don't fuck bare very often but surprisingly the very first load i took was the first time i ever had anal. I just turned 18 and horny as hell, after chatting for about a week or two with a guy on the Internet i decided to go on an "adventure".. He was a 36 yo american guy quite handsome and well hung, i didn't have much experience with sex in general and still kinda innocent. I just went for it it and asked him to meet. After a few days i left home with some excuse to my parents( going to spend the night at some friend's house) and took a train literally across half the country, (italy) and met him in Naples. We had a walk, talked a bit, got to know each other. After some time he took me to a sauna, (i had never been to a sauna before so i was kinda nervous) we drank something got in a private stall, and he offered me to smoke some weed to "loosen up" i accept the offer happily and after the joint, high as fuck he took me to the pool and gave me a bj in front of all the man there, i felt embarassed and yet so aroused, after reciprocating and feeling all the looks and some light touching on me by the rest of the people. We went upstairs and he told me to lay on a sling. And then proceeded to rim me and push his cock on my hole, i never wandered about his status nor ask for it i was just so taken by the moment i let him have me right there in the middle of the room, high and bare with nothing but spit as lube, it hurt..a lot.. Fortunately the weed helped with that . After getting me loose a bit he started pounding me hard while saying how he would wreck my boy pussy, and what a slut I was..i loved every second of it. He came in my ass grunting like an animal never pulling out, i took 2 of his loads in my ass and 1 in my mouth that evening. After we showered and left the sauna he told me he was actually 42 and not to worry because he was neg. I didn't care for his age at that point and was relieved he didn't have any sti's. We had dinner and parted at the train station that morning at 3.am i spent the night "sleeping" on one of the station benches and took the train the next morning while thinking how stupid i was and what shit could have happened.. After getting home my parents were furious they found out i lied and they tried to call me several times, and pushed to know where i had been.. I never spoke a word I just sat quietly through all the ranting and didn't speak till i went to bed ... I layed down and i cried the rest of the night.. Ifelt such an idiot.. Never brought up the topic again with my family, i remember being so ashamed and feeling dirty..
Today i still remember that couple of days like it was yesterday, fondly, and each time i recall them i just laugh at how reckless i was.
It might seem foolish or exagerated but it's exactly what happened. I regret nothing.