I have a best friend named Jake who was 13 years old at the time of the story, I was 16. Jake was and is the absolute sweetest most adorable guy you would ever meet in your life, he is very short and light and just has the cutest little face and body ever.
Anyway, one day I was giving him a ride home after school and he started saying that he was really horny. I've always secretly wanted to give Jake an orgasm, and when he said that I just lost it. I remembered that my parents weren't home that night so I asked Jake if he wanted to have some fun at my house and then I put my hand on his inner thigh and started squeezing it. He gave me a little smile and said, 'Sure, I'd love that.'
When we got to my house we laid on my bed in my room and I just started hugging and cuddling Jake. For a long time I had been fantasizing about doing this with him, so I had a plan of what I wanted to do. I decided to just go with it and see what would happen. First I completely stripped him butt naked and then I grabbed a shaver. I completely shaved every single hair he had all over his little tiny body. I completely shaved his butt cheeks, his butt hole, his taint, his balls, his pecker, his stomach, his back, his armpits, and his upper and lower legs. Next I started slowly caressing his velvet skin all over and then I grabbed a feather to slowly tickle and tease him. I tickled his most sensitive parts with the feather and he almost blew just from that so I stopped.
After all of that I wanted to give him a super erotic strip tease. I put a pair of super cute little boy cartoon tighty whities on him, then I put a pair of cute boy's gym shorts on him, then a pair of baggy sweatpants and then a T-shirt. first I took the T-shirt off and started tickling his nipples. Then I flipped him on his stomach and grabbed his ankles. I started to extremely slowly work my way up his back legs until I got to his butt cheeks. Once there I started squeezing and fondling his butt cheeks and I kept touching his hole through the sweatpants. He was moaning in pleasure so I flipped him on his back and pulled the sweats down. Then I put my hands right in his inner thighs behind his ball sack and started to slowly work down his ankles.
After that I took the shorts off, leaving him in his underwear. I stuck my hand in the little Y-front and pulled out his four inch erection. I started stroking it while I squeezed his butt cheeks with my other hand. After a while of that I pulled down his underwear and grabbed some lube. I told him to lay down on the bed on his back with his knees bent. I put the lube on my fingertip and stuck it up his butt hole, then I followed up his taint and started squeezing his little balls. I stroked him with the lube until he was about to cum. When he was about to cum I had him go on the floor and sit his cheeks on his heels. I told him that when he was going to cum to spread his butt cheeks as far apart as he possibly could with his heels and it would feel amazing. When he did this I grabbed his balls again and he shot 5-10 huge ropes of cum that shot everywhere. He was completely out of breath and just collapsed into my arms. He started saying how much he loved me and that he'd promise to do it to me some day. He did do it to me, but that's another story that's just as amazing. I hope you enjoyed my story of giving the cutest little cutie in the world a huge orgasm.