Let me start off by saying I have a butt fetish. If a see cute guy with bottoms that have a good outline of his buttcheeks, I get an instant hardon.
Anyway, years ago in my gym class there was this adorable boy that was about 4'9' tall and weighed about 95 pounds, and he was the absolute cutest thing you could ever imagine. He had the most adorable little face with the cutest button nose ever and it just makes you want to give him the warmest hug everytime you see him. The best part is he wore real tight little gym shorts that gave a beautiful outline of his buttcheeks, and it just looked like the cutest butt in the world.
Now, me and this boy were very good friends and we gave each other hugs and always told each other we love you, in a brotherly way at least. I always wanted to tell him how badly I wanted to have a sexual encounter with him, but was always too scared. One day however, we were alone in the locker room together and he was standing up on a bench giving me a back rub. I picked him up by his legs and placed him on the ground and gave him a huge hug. I told him about how badly I wanted to jack off with him, and he instantly said he would do it. We planned to do it in the bathroom after Biology class during lunch.
Biology was over and we waited for the hallways to clear out and everyone to go into the cafeteria, then we went into the boys bathroom together. Once in there I locked the door and we went into a stall, which I also locked. I told him to get up against the wall and spread his legs so I could 'tease' him, and he did it. I started out by giving him a standard bodysearch similar to one at the airport by starting at his ankles and moving up to his buttocks, except I did much more slowly and sexually, with a great deal of time spent on rubbing his butt. I then removed his belt and pulled his pants down, leaving him in a pair of gym shorts. They were really velvety and felt amazing in my hands so I assumed they would feel amazing on his cock. I did the same back buttocks search again groping his cheeks with much love, but then I told him to spin around, and I performed the same pat down on his front side. I put my hands around his ankles and slowly worked up his inner thighs and massaged all around his cock, he had a throbbing erection and was begging for me to get started, but I had to finish my teasing. I pulled his shorts down leaving him completely butt naked and told him to sit his butt down on the toilet. I pulled out a bottle of KY jelly and rubbed some on his nipples, some in his butthole and some on his penis. I started out by slowly tickling his nipple, and then I slowly fingered his butthole. I grabbed a hold of his cock and slowly stroked him as I fingered his butt. After about 20 minutes of me stroking him and finger banging his anus, he said he was about to cum. I told him to get up from the toilet and sit down on the floor on top of his heels. I continued to stroke him and told him that right before he came, he should spread his buttcheeks as far apart as he could with his heels and it would feel amazing. In about 20 seconds he had done this, and he had the most powerful, body shaking orgasm I had ever seen.
After he splooged his goo, I cleaned him up and cleaned up the floor, then I redressed him. He told me how much he loved me and gave me the most amazing hug he had ever given me. Since there wasn't enough time left he couldn't do me then, but he promised he would do me the next day, which he did, and trust me, it was just as amazing.
That is the story of how I gave the cutest boy in the world an amazing orgasm, and how our numerous sexual encounters began.