He asked me to show him how girls do it. That led to him showing me what I wanted to see.
Jason was only in my class because he skipped second grade due to being real smart. We lived only a few doors away from each other. He texted me to come over to his house, he wanted to ask me something.
At his house he took me around to his backyard. He said he was wondering for a long time about how girls do it. 'Do what?' I asked. 'You know....'
Clearly he was embarrassed to say it, so I egged him on until finally he blurted out 'How do girls masturbate?'
I was taken aback for a bit. I didn't say anything. He said 'Are you mad at me for asking?'
'No, just speechless.'
'I'm sorry. Forget I asked.'
I said 'No, no. It's ok. I can show you real quick.' His eyes lit up. 'You will? How?'
'Like this' I said. I spread my legs and put my hand on my crotch over my shorts and started rubbing up and down.
'That's all?' he asked. 'Yeah, that's pretty much it.' I said.
'You do it standing up with your clothes on?'
'No, stupid!' I said. 'I do it laying down naked in my bed, or with my PJs on.'
'Really?!' He was clearly interested.
'Really.' I said. 'But now I want to know how guys do it.'
'I can't' he said.
'Not fair. I showed you. You have to show me.'
So he made a fist with his hand and pumped it back and forth in front of his crotch.
'I want to see it for real' I said. He said I would have to show him for real too.
Neither one of us was going to do that and I went home. But I didn't stop thinking about it.
Later I texted him and said 'I'll show you if you show me.'
Not three minutes later, he was knocking at my door. We went up to my room. Mom was busy cooking in the kitchen and didn't see us go.
I locked my door and we nervously paced around not knowing where to start. Finally he said 'You really do it naked?' 'Yes. You go first.'
He said 'Together, then.' So he kicked off his sneakers and socks. I was already barefoot.
He tentatively lifted his tee-shirt part way, looking at me, waiting for me to follow. So I took off mine.
Then he unzipped his shorts and waited to drop them until I did so too. I started sliding them down and we stepped out of them in unison.
Next went our undies. He was naked and his boner was sticking out. He said 'Your bra too.'
I wasn't too eager for that, but he said he's naked, I have to be naked too. So I took it off.
Then he said 'You first' and I said 'No, you first'. He said he needed some lube and I offered him my Vaseline jar. He scooped out a dab and sat on my bed and started jacking, while looking at me... well mostly at my small tits.
After a short while he layed back, closed his eyes and grunted in a low animal way. It sprayed all over his stomach. I gave him a box of tissues and he wiped up and sat up again.
He said your turn. I felt real awkward and wanted to back out but knew I was obligated.
So I laid on my bed and closed my eyes. That made it easier to feel like I was alone. I was already wet and it was easy to start. I spread my legs and started masturbating.
But it wasn't really working for me because it was so embarrassing. I was almost about to quit. Then I got an idea to make it feel better. I told him it wasn't working, but he could help. I told him to sit next to me and lightly rub my tits and nipples. He was all too eager. And that extra sensation made it feel real good for me and I got bolder and told him to lightly caress the insides of my thighs. This did it for me and I came in a couple of minutes.
That incident was the start of many mutual masturbation sessions we shared that summer. We became sexual a few months later and now we are engaged to be married.