Note: I would like to dedicate this story to the magnificent Colleen Thomas. Her writing is timeless and everyone can learn from it!
Simon Jacobsen reluctantly got out of bed and slowly walked toward his older brother's bedroom. There was only a year separating him from Caleb, and like most younger brothers, he put the older man on a pedestal. As they were growing up, the siblings were more like best friends. They had nearly the same interests and their personalities were very well matched. Simon was a little more private than the outgoing Caleb. By the same token, Caleb needed Simon's level-headedness to bring his exotic schemes back down to earth.
The house was deathly quiet as Simon entered Caleb's room. His parents were away for two weeks visiting relatives, and would miss Hanukkah entirely. Caleb had gone off to the nearby junior college he had just enrolled in this year. Simon would have normally been in school with the senior class of Bordertown High, but this particular Tuesday was a conference day and so he was free...for the moment!
Simon was very concerned because his diary was missing. In it, he confided his deepest thoughts, and lately they had been more and more sexual. Since turning eighteen last July, Simon had become much more aware of his older brother, in every way. The two boys looked alike, but Caleb had two inches on Simon's six foot two inch frame. He also sported a thin moustache whereas Simon was clean shaven. But it was in the penis department that Caleb was blessed. Simon's mouth watered as he tried to catch his older sibling coming out of the bathroom every morning. One time Caleb had a morning wood and the head and part of the cockshaft poked out of his patterned boxers. Simon figured that his brother's cock had to be at least nine inches hard, and was dying to see it.
In the sad half light of the small bedroom, Simon could see the many ships in their respective bottles on top of Caleb's dresser and desk. His brother was a skilled glass blower, and his creations were miniature works of art. Simon fingered the latest project, a gentian blue clipper which was only partially completed. No name graced the proud ship yet, but Simon could see that the small cup of black paint next to the bow was ready once his brother had decided on a title.
Simon felt a twinge of guilt going through his brother's stuff, but he simply had to find that diary! The last three pages were detailed sex scenes, and his brother was mentioned constantly. Simon would die from embarrassment if Caleb ever read his diary, and he no idea how he would explain it.
Simon started with Caleb's sock drawer. His brother wore short white ankle socks, and had a multitude of them. Simon looked under the socks, but found nothing. He then proceeded to the next drawer, which contained Caleb's underwear. His brother wore white sleeveless undershirts and colorful full cut boxers. As Caleb lifted up the neatly folded underpants hoping to find his diary underneath, he felt a stirring in his loins. There was something about touching Caleb's boxers that was so....so forbidding! He decided it was time to take a break from all this sleuthing. Simon picked up a pair of turquoise silk boxers and lay back on his brother's unmade bed. The sheets smelled slightly sweaty, and Simon wondered if his brother had beat off that morning.
Taking his painfully hard shaft and hefty balls out of the ample fly slit of his own baby blue boxers, Simon wrapped Caleb's silk underpants around his cock and slowly started jacking off. The sensations were so exquisite he let out a loud grunt, then uttered expletives he would never use in real life.
Simon fantasized he and Caleb were kissing. Their tongues came together in wild abandon, and the long wet liplocks seemed to go on forever....
Simon's hand was going up and down on his cock so fast it was merely a blur. His moans became higher pitched as the silk fabric of Caleb's boxers drove his prick wild. After a couple of minutes of extreme ecstasy, Simon let out a shrill scream that could have been heard over a city block. His cock started spurting the Load of Loads into Caleb's thin underwear. After nine very full spurts, Simon lay back on the bed with a contented smile on his face. He fell asleep immediately, dreaming of himself and Caleb on an endless bed, having equally endless sex.
The slam of a door downstairs abruptly woke Simon up. It was Caleb, home from school! Simon hurriedly threw Caleb's ruined silk boxers in a nearby hamper, then quickly scurried back to his own bedroom. He had barely time to jump into a pair of pants, when Caleb came into the room with a mad look on his face. Simon's jaw dropped when he saw the little red notebook his brother was carrying....his diary!! He felt the color drain from his face and looked down at the floor, wanting to die.
"I read your diary!" Caleb looked at Simon with daggers.
"M-M-a-a-n-n-" Simon started stuttering uncontrollably. "That was a d-d-different Caleb..a g-g-guyyy in s-s-s-c-chooll." Simon was faltering, and he knew it.
"It was me...and you know what?"
"W-w-what?" Simon continued to stare at the floor, hoping he would fall into a secret chamber.
"I have a diary too!"
Simon looked up at Caleb, who was suddenly grinning like a Cheshire Cat!
"h-h-h-uhhhh?" Simon didn't get it.
Caleb reached into his bookbag and produced a small blue notebook, about the same size as Simon's red one.
"I've been writing the same kind of stuff you have..about my secret admirer."
"You mean Mary Stein?" Simon was incredulous. Mary Stein was the heartthrob of every red blooded boy at Bordertown Junior College.
"No, silly," Caleb smiled warmly. "YOU!"
"W-w-w-w-what!" Simon couldn't believe this amazing aboutface.
"I want to do the same things to you that you want to do to me."
"B-b-b-u-t-t-t-t-" Simon hands started to shake with anticipation. "We're brothers."
"Didn't stop you from writing about it, did it??" Caleb let out a hearty guffaw and slapped Simon on the back.
"So n-now what do we do?" Simon still had not fully comprehended that his wildest dreams were about to come true.
"Well instead of giving each other dinky presents each night of Hanukkah like we usually do, let's offer each other some very physical presents, if you know what I mean!"
"You mean starting tonight?" Simon's face was a beacon of joy.
"Tonight's the first night of Hanukkah isn't it?" Caleb looked at his brother with pure Love.
"Yeah, guess it is." Simon felt the beginnings of another hard on in his khaki trousers.
