As much as I'd like this story to be true, it is entirely fictional.
When I was 15 I had a 13 year old friend named Jason. In the summer, I was at the local swimming pool with my family. A few minutes after I had entered the pool, I saw a wave from Jason, who had just came in. I told my family that I would swim with Jason for a while. At the time I was wearing plain blue speedos and Jason was wearing black boardshorts with blue stripes down the side. I swum with Jason for a while before we sat on the gutter right on the edge of the pool.
'Nice speedos,' he said.
'Yeah, they're cool. You ever worn one?' I asked.
After we finished swimming and talking, both of us headed to the changing rooms. There, we showered together, with our swimsuits on. Suddenly, Jason pulled his boardshorts down to reveal his semi-erect penis.
'You look nice in your speedo' he said, and soon I began to have a boner of my own.
'Thanks. Maybe we should buy one for you someday.'
A few weeks later, we had our chance. After school we both went to the local shopping complex and looked through stores for speedos. We found a shop with a huge section of speedos- three long rows of them. Jason grabbed a few different speedos and asked me to come with him to the change rooms. When we got there, we saw no-one near us, and so we went inside a cubicle together.
The changing cubicle was quite large, with lots of floor space. I had a quick look through Jason's selection of speedos and before I knew it he had stripped down to his underpants. From this point I could tell he had a semi-erection. His penis stuck out straight in front of him. Then he asked me to hand over a pair of speedos to try on.
'Here, I'll help you'
I went over to Jason and pulled his undies down fast, making his penis bob up and down slowly.
'Hey, be gentle'
'Sorry, I will be'
I then grabbed a red pair of speedos, knelt down in front of Jason and held it in front of him, stretching a little wider than necessary.
He placed his legs inside the speedo and I began to slide the speedo up his legs. A few centimeters from his penis. I stopped sliding it up further, tightened one hand on the speedo as I reached his balls with the other hand.
I tickled his balls and he giggled a bit.
His penis began to slowly rise, and soon enough it was fully erect. At that moment I pulled his speedo up and let him tighten the string and make himself comfortable in it.
'Wow, that feels awesome' he said as he looked into the mirror. 'I'm taking this one'.
Without hesitation Jason, slipped off his blue speedos, changed back, paid for the speedos and we left to go to my house.
My parents both worked and got back at 7 at night. It was on 4 in the afternoon, and the sun was still fairly hot. When we reached my house, we went to my bedroom.
'Hey let's wear our speedos!' Jason suggested.
We changed into our speedos. Jason had the plain red ones he bought and I had the light blue ones I wore to swimming. With just our speedos on, we lay on my queen size bed, resting on our sides and huddled close together. It was then that I asked Jason if he masturbated.
'I'll show you'
I asked him to loosen his speedo but still keep it on, and I loosened mine as well. Then I asked him to lie on top of me, facing me, so our boners would touch. He was shorter than me, the hair on his head just touching my nose. As he got comfortable I reached inside his speedo and massaged his bum.
He let out a small groan as I worked my way across his bum to his balls and massaged them as well.
His penis was extremely hard now, and the friction between our penises and speedos was the most amazing sensation I ever felt. Now, I began to move up and down my bed and started to groan as well. We were rubbing our cocks together and turned as we rubbed. Soon we were back on our sides again.
'And now I do this' I said and reached to feel his penis inside his speedo. Jason's cock was 5 1/2 inches, pretty decent for his size. He had no pubic hair and was uncircumcised. I pulled down my speedo to my knees and asked him to lie on top of me again, so my boner could be in between his bum and I could jack him off while giving myself a nice pleasurable time as well. When he got into position, I pulled gently up and down at his foreskin, speeding up slowly.
'Oh, this feels so good' he groaned out
'Yeah, its cool'
Soon he asked me to stop, and said he felt something was going to come out of his penis.
'Don't worry, its just cum'
'Relax. Just think of something sexy'
Jason closed his eyes as I jacked him harder and harder. Then, he stiffened his body, straightened his legs and tensed so four or five long ropes of cum shot out of his penis. Underneath, I began to shoot at the sight of his cum, but since I masturbated often, it wasn't as much as him.
When the fun was all over, we cleaned up and changed back to our normal clothes. He said he would wear his speedos again soon...