My younger brother, Jake and I have always been close, even though he was born two years after me. I remember as kids we would strip off and compare hardons. Even then I remember thinking we had bigger dicks than all our other friends.
As we grew up we became quite different. He was a jock and I was a science geek. He was on the football team and I was chess captain. It wasn't uncommon for us to get mistaken for twins though as my brother has always been tall for his age and I was a late developer. We both have blonde hair and are quite broad. We get out build and body from our dad.
I wasn't just a late developer in a physical sense but in a sexual way too, at 16 I still hadn't discovered the pleasures of masturbation. I got boners all the time, but I guess all my geeky buddies didn't talk much about that kind thing. At any rate that was all about to change.
It was holiday time and we were visiting family in Canada. Mid-journey we were staying in a motel. Now the motel was very busy that weekend and our parents had only managed to get two double rooms at either end of the building. So after much complaining my brother and I were forced to share a room together. It was quite late and we had been traveling all day so as soon as we got to the room, immediately stripping down to our boxers and getting into bed. After getting cozy and fighting over the blankets with my brother I went to sleep.
It was about eight o'clock the next morning when I was woken up. As I slowly awoke did I became aware that the bed seemed to be rocking around. I turned over to see what was happening. I got the biggest shock of my life! Jake, my little brother, had thrown off the sheets and both his hands were busy massaging his massive organ. His head was huge and the shape and colour of a plum. He moaned every so often and sometimes thrust his hips up forcing his dick through the fists. He had his eyes closed and was squirming with pleasure.
'Jake what the are you doing!?' I asked. He stopped immediately and looked straight at me.
'Sorry man. I just had to jack off you know, I can't go without it for too long.'
'So that's jacking off!' I exclaimed. I had heard the term before, but didn't really know what it meant. Jake gave me a puzzled look before speaking.
'You mean you've never jerked before? Gee man your missing out on a lot. I knew what to do with my meat at 12 and I've been doing it three times a day ever since. We gotta get you into training!'
I didn't have time to respond before Jake pulled the covers off me and pulled off my boxers. My flaccid pink prick stood to attention quicker than a firing gun. Jake sat up and stared at my considerably big erection for a moment.
'How big is it?' he asked,
'I don't know. I never thought to measure.'
'Wait a second,' with that Jake rushed over to his bag and rooted around untill he found a tape measure. He then bounded back over the bed and grabbed my cock and started to measure it. It felt so good to have his warm hand working around my dick. First he measured the length and then the girth.
'Pretty damn good bro, but not as good as me. Guess I'm gonna have to call you little brother from now on.'
'What do you mean?' I asked.
'Well your cock is 10 inches by 7 and mine is 12 by 8.5.'
He measured his cock to prove the point. It was after that he turned his attentions back to me. I didn't mind that he was bigger than me as I knew that I dwarfed most of the guys in the locker room.
Jake set to work grabbing my cock. He gently juiced my mushroom head and all the time working the great trunk from base to top. For ten minutes he went quite slowly working me into a frenzy. I'd never experienced anything like this before. Sure I'd had a wet dream, but I just thought I'd wet the bed in my sleep. Suddenly Jake stopped and grabbed my cock hard and fully with both hands.
'Watch out bro. This is were I'm going to make you scream!'
With that he started to pound my penis faster and faster. The head turned rock hard and purple. I gripped onto the sides of the beds not sure what to expect. All I knew was that I liked it. Blood rushed up my massive veiny penis and I felt as if I needed to pee so much that if I didn't my cock would explode. It was at this moment that we heard a click as the door opened and someone entered the room. We must have forgotten to lock it. It was too late though and just as Jake stopped pumping I saw spurts and spurts of cloudy cum straight up into the air and back down onto my chest. I opened my eyes in awe at what had just happened, but scared of what was coming next.
'Looks like you boys are having a good time.' It was dad. Jake and I went red with embarrassment.
'Hey, boys don't be ashamed' he said reading our emotions.
'Masturbation is perfectly natural and healthy past time. I do it myself everyday. Why your Uncle Peter does it five times a day, I think that's why he doesn't have a wife.' Jake and I both giggled. Our feelings of shame disappeared as we saw that Dad was fine at what had just happened. I began to clean the cum of my chest with tissues. Dad looked from me too Jake and then his eyes turned to our dicks.
'Looks like you too our carrying on the family tradition.' he said with a wry smile,' You don't just take after me in the looks department, though you both look as if you have a little way to go before you beat me. I used to bet people at college that I had a bigger dick than them and I won every time. Hey don't look so shocked. There's nothing wrong with having a bit of fun with other guys from time to time. In fact it was Uncle Peter who showed me how to jerk off when I was 9. When did you two start?'
Jake answered first, 'I was 12 and I just kept getting these boners. I didn't know how to get rid of them, until one day I went into the bathroom to get a towel whilst you were in the shower. You didn't see me because you had your eyes closed Dad, but I saw you beating off and was so impressed I tried it that night.'
Dad laughed slapped Jake on the back and then he turned to me. I looked down and explained that Jake had only just taught me there and then. Dad told me it was ok to be a late starter.
'I think we need to celebrate your new found skill in someway.' He said 'I know.' and with that he began to unbutton his jeans slowly. He then got down to his boxers from which a huge bulge protruded. He removed his boxers to reveal a cock bigger and wider than both Jake's and mine. We stared at the big, veiny tree of a dick for a moment. Dad sat in a chair by the bed spreading his big, hairy sportsman's legs revealing his huge flaccid cock, which was topped with dark black fuzz. We watched and swelled as it gorged itself and stood straight out and the fore skin pulled away to reveal a massive pink head. Dad began to stroke it with all the skill of a craftsman who has mastered his tool.
'You boys want to know how big it is huh? Well I'll tell you. It's bigger than uncle Peter's eight inches and even Grandpas ten; my cock is the biggest in the family. I am fourteen inches long and ten inches wide.'
He smiled at us, closed his eyes and began to work his love tree. My cock was obviously ready for more and began to bob up and down anxious for a second chance. Jake hadn't needed telling twice and was already busy pounding away with both hands again. I grabbed my dick and mimicked dads up and down technique, hitting hard and fast. Jake was the first to cum standing up on the bed and aiming his cock directly at me. I turned just as he was cumming and his purpled head pulsated and shot a solid line of cum in my face.
'Hey play fair!' Dad said standing up and handling his cock faster and faster with both hands now. His low hanging big balls bouncing around all over the place. He put one hand on the chair to steady himself and aimed straight up at Jake cumming six strong jets straight at him.
'Wow that was good!' He exclaimed.
It was my turn then and I was so turned on by Dad and Jake that I creamed almost as soon as Dad did oozing straight into my right hand. I lay back on the bed blissfully happy.
Three years on and I'm now a full-fledged masturbator managing to do it about four times a day and often with Jake. I'm bigger now with a full 12 inch by 9.5 to my name now but Jake's still beating me with a 14.5 inch by ten putting even Dads to shame!
Lots more stories to come!