He was too shy to try anything so I had to pull him along
We were both 16 at the time this happened at a summer camp for boys. The camp had a hotel at the top of the hill, where parents (and others) could stay and watch the camp activities from their balconies. I was a maid for the hotel. He was the chef's assistant.
We both fancied each other but he was way too shy and inexperienced to dare try anything with me. So I decided to get things moving. I asked him to show me how to play the guitar. We were sitting on the edge of his bed and I pretended to fumble around not knowing where to put my hands or what to do with them. I told him to reach around me and show me, and I moved to sit in front of him between his legs. He reached his hands around and took mine, placing one on the neck of the guitar and the other at the strings. That's when I struck.
I grabbed his hand and pulled it to my tits and said this is the guitar I really want you to play with. I put the guitar down and let him fondle me for a while then quickly removed my top and let him play with my 30AA tits directly on my skin.
I then said don't forget the low notes and took one hand and guided it to my crotch. I had to lay back against him to give him the access. We ended up me laying on top of him, both of us facing up, with his hand on my tits and the other one inside my shorts.
I showed him how to masturbate me and he went right at it and gave me a thundering orgasm.
After that, I got up onto my knees on the floor facing him between his legs and let out his cock and gave him a hand job. He came almost immediately.
Since I got him to break the ice with my guitar lesson, we started masturbating each other all the rest of the summer.