True story. I can't put on a rubber now without thinking back to that moment in time. Hope you enjoy.
My first experience with a condom was when I was 16 years old. I shared a room with my brother who is a year older than I am. One night while we laid in bed still awake we started talking about girls, sex, jacking off, and about rubbers. My brother asked me if I was hard yet, I told him of course. This is usually how our conversations went several times a week. We would usually end up jacking off ourselves or each other. My brother then asked me if I had ever seen a rubber before. I told him no. Sure, I knew what a rubber was and had seen a package of a rubber but I had never actually seen a rubber itself out of the package.
He sat up on the side of his bed and turned on his bed side lamp. He was naked, with a 8" boner pointing up and two rubbers in his hand. He said "I've got a couple right here, you want me to show you how to put one on?". I sat up on the side of my bed naked with a 6 1/2" boner of my own and said "hell yes!". He got up from his bed and walked over to me. He told me to lay back down and he would show me how to put it on. He opened the package and pulled out the rubber. I watched as he placed the rubber over the head of my dick and slowly unrolled it all the way down to the base of my shaft.
He smiled and stroked my dick a few times saying "That's the wildest feeling! Here, stroke it and tell me that doesn't make your dick wet." I reached up and took my dick from my brother and ran my hand up and down my shaft. He was right. Just feeling my dick inside that rubber made my balls tighten up and I could feel the pre-cum ooze out as I flexed my dick. He handed me the other rubber package and told me to put the rubber on his dick so he could make sure I was doing it right.
I opened the package and took out the rubber. This rubber seemed to be slippery in my hand. My brother noticed it and said that rubber must have lube on it. I placed the rubber on the tip of his dick and tried to unroll it. It was very slippery. Every time I got it past his dickhead and tried to get over his hard shaft my fingers would slip off and it would roll back up to sit on the ridge behind his dickhead. On the third attempt I managed to roll it all the way down to the base of his dick. You could see both of our dicks clearly through the rubber.
I sat back up on the edge of my bed and leaned backward onto one of my pillows, my brother sat down next to me and also leaned back on one of his pillows. So side by side we stroked our dicks. My brother told me that my pre-cum should lube the inside of my rubber so that I could jack off using the rubber. I must of had a confused look on my face because he reached over and started moving the rubber over the tip of my dick. The rubber became slick and it moved easily over my dickhead. Using the rubber he continued moving my pre-cum down past the head of my dick and onto my shaft. Wow, it felt great. He told me to do the same thing with his rubber.
I wrapped my hand around his 8 inch dick and started to slide the rubber over his dickhead. My brother has always been a heavy pre-cumer and so his rubber was sliding easily over his dickhead and halfway down his shaft with my first stroke. The sensation of the rubber sliding up and down my dick was sending me to the edge quickly. I would not be able to hold out for very long.
I started moving my hips in rhythm with my brothers stroking and his hips moving to the rhythm of mine. As I watched my brother's hand moving up and down on my dick I told him I was almost there. He said "I'm with you little brother. I can feel my dick filling up with my cum.". My brother's words and the feel of this hard pecker in my hand did it for me. I felt my nuts tighten and my dick harden even more. I'll let out a soft moan as I pushed my hips up hard against my brothers hand. My brother said "Yah, that's it little brother, blow your load!!".
My brother and I watched as my dick spasmed and started filling my rubber with my cum. My brother moaned "That's it, oh shit, that's so hot! I'm cumming!" He froze as I pulled tight his rubber and felt his dick flex in my hand. Side by side we filled our rubbers with our thick white cum. My brother is a heavy, heavy cummer so his dick quickly disappeared inside his cum filled rubber.
We both slowly stroked the remaining spurts of cum out of each other's dicks. WOW!! AWESOME!!! We caught our breath as we laid there watching our slowly deflating cum filled rubber covered peckers.