My first boyfriend was a year younger than me and went to a different high school. Sex for us was very…innocent (at first!). Never any sucking, just some jerking and kissing. Well, two months into it, Jack (the bf) started getting restless and distracted. After asking him several times what was wrong, he finally said, very quietly “i want to stick my tongue up your butt. I saw it on an online video, and I just can’t stop thinking about it.” I was totally freaked out by the thought of it—i mean, you know, it’s an asshole—well, I finally agreed to it and we made a date when no one would be at my house, and we could explore with leisure.
He called me right before he came over and again said, “just make sure you’re clean down there.” After heading up to my bedroom and stripping down, he shoved me onto the edge of my bed, spread my legs apart, and dove right in. Having never felt it before, all i could muster were high pitched gasps and comments like “oh! stop! stop!” and “i don’t know about this”, even though i was solidly enjoying the moment. He was clearly having a great time, and would stop and say, “damn, your hole is so hairy!” and would whimper a lot. I didn’t last long, and soon shot all over myself. He came with his tongue still in my asshole and said afterwards, “I felt your asshole twitch when you came. It made me shoot.”