The Eight Nights of Hanukkah

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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.” demetevler escort 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.

“I have to go to the library to study for an exam tomorrow. Make sure to be here when I get back.”

“Of course!” Simon would have agreed to having his head cut off at this point.

In a flash Caleb was gone and Simon started wondering if he had just dreamed the whole sequence. After he came back to earth, he took a cold shower and tried to calm down. Simon decided to get dressed up for his first “date” with Caleb. He put on his best dress trousers and a matching navy blue blazer. The next four hours passed agonizingly slowly as Simon half-heartedly played some computer games and listened to CDs. Finally, there was the unmistakable sound of a key scratching against a door. Simon ran to the front door, opening the heavy wooden portal before Caleb had a chance to turn the key to his heart…

“Hi man.” Simon tried to act casual.

“Hi Bro.” Caleb simply smiled.

“You ready?” Simon looked at Caleb like an eager puppy.

“Ready as I’ll ever be!” Caleb suddenly looked a little embarrassed.

“Let’s sit on the couch.” Simon gestured to the living room.

“Sure!” Caleb led the way to a large flowery sofa that could easily seat four people. The horny siblings sat right next to each other, holding hands. Caleb made the first move. He leaned over and kissed Simon on the cheek. Then he moved to his mouth. A tongue tentatively came out and manuevered its way through Simon’s lips. His brother returned the favor and their tongues dueled like two playful snakes. At the same time, Caleb rubbed Simon’s nipples through his blazer. Simon ran his fingers over his brother’s neck and upper chest. Both men felt their insistent boners pressing against their dress slacks. Suddenly Simon let out a muffled groan.

“O-h-h-h-h-h- SHIT!!”

“What happened?” Caleb had a concerned look on his face as the brothers broke their lip lock. He looked down at Simon’s crotch and started to laugh hysterically.

“You creamed your pants!” Simon turned beet red as Caleb continued to chuckle.

“I didn’t mean to…it just happened!”

Caleb took Simon’s hand and placed it on his own crotch. Sure enough, there was a large stain across the front of his white trousers. Now it was Simon’s turn to laugh.

“You creamed your pants too.”

“Yeah, we came together, man!”

The brothers felt a little awkward after their quick but intense orgasms.

“Tomorrow will be better, I promise!” Simon suddenly felt woefully inadequate.

“You were fine.” Caleb kissed his younger brother on the cheek. “I love you, man!”

“I love you too,” Simon nuzzled Caleb’s cheek as he started daydreaming about the next evening.


It was very hard for Simon to concentrate in school the next day, but somehow he managed. Caleb had late exams and wouldn’t be home until 8 o’clock. After school Simon went over Jacob Finkleberg’s house, his best friend. The two boys watched the original Star Wars, shared a pizza and a lot of sexual jokes. Then it was time for Simon to go home. He hummed merrily as he drove the short distance to his humble abode. Caleb’s sky blue Toyota Corolla was already in the driveway. Simon quickly opened the door and bolted into the kitchen. Caleb was nowhere in sight.

“Caleb, where are you?” Simon escort demetevler was nervous already.

“I’m up here.” Simon heard a muffled reply from the bedroom.

Simon bounded up the staircase two steps at a time and raced into Caleb’s bedroom. There was his sexy brother laying lazily on the queen size bed, clad only in a white sleeveless undershirt and blue plaid boxers.

“What’s up?” Caleb smiled wickedly at Simon as he fingered the large bulge in his underwear.

“I think a lot!” Simon started throwing his clothes off until he too was in a similar wife beater and blue striped boxers. He jumped on the bed and the two men embraced in a hug that defied time. After what seemed like an eternity as the two brothers made out and french kissed into oblivion, Caleb suddenly broke their torrid embrace and reached into a small drawer by the bed.

“What are you getting?” Simon asked quizzically.

“Just some lube.” Caleb answered matter-of-factly. “I saw some cadets do this in a movie once and it looked really hot.”

Caleb generously greased his cock with the lube and did the same to Simon’s wang. Then, he got on top of his younger brother and grandually pushed his long thin shaft into the fly opening of Simon’s boxers. At the same time, Simon’s bone hard prick pressed into Caleb’s boxer slit. The two men let out loud groans as their lubed cocks pressed against each other. Then Caleb started thrusting his boner in and out of Simon’s boxers. The sensations were so incredible for both of them they both groaned and grunted like sweaty pigs.

“I’m gonna cum man…Caleb finally managed to get out…this is too intense!”

“Me, too!” Simon squeaked. “Let’s cum together!”

Caleb gave one tremendous thrust into Simon’s boxers and let forth with a hoarse wail. At the same time Simon screamed with lust as both men dumped a full eight squirts in each other’s shorts. Caleb collapsed on Simon, still breathing heavily.

“That was unbelievable!” Simon had never felt so emptied yet content at the same time.

“Definitely better than last night!” Caleb grinned at Simon and gave him a deep kiss. The two brothers quickly fell asleep in each others’ arms…..


The third night of Hanukkah progressed even more smoothly. After a sumptuous feast of macaroni and cheese, cheerios, and stale coke, the brothers quickly stripped to their underwear and climbed into Caleb’s waiting bed. For some reason, they didn’t quite feel comfortable being totally naked with each other..yet. Simon quickly reached into Caleb’s white boxers and starting jacking his massive prong off furiously. Caleb, in turn, pulled Simon’s beautiful hard-on out of his checkered shorts and masturbated him with two hands, the way he usually did it himself.

“Hold on man, I don’t want to cum that fast.” Caleb gently slowed down Simon’s vigorous pumping.

“Oh, Ok, sorry.” Simon was so excited to be actually handling his brother’s cock he had lost control of himself completely. The two brothers looked into the depths of each others’ eyes as they slowly jacked each other off contentedly. Then, Caleb leaned over and gave Simon a kiss. A kiss without end, as the two brothers turned lovers sloppily thrust their tongues in and out of each others’ mouths. For the next 15 minutes time stood still as the two brothers’ hands explored every nook and cranny of their ample endowments. Simon was the first to lose his load.

“F-f-f-f-uck!” His cock started spasming just as Caleb felt his own impending orgasm.

“Jesus!” Caleb grunted as he cock started shooting off like a cannon.

The two brothers laughed together as their cum flew everywhere, on Simon’s discarded shirt, the headboard, a model ship, and the previously pristine white rug. Then they tickled each other unmercifully until they finally fell asleep.


On the fourth day of Hannukah, Caleb had another long day of school because it was a Friday. Simon just went through the motions at school, fantasizing the whole day about sucking Caleb’s cock that evening. He couldn’t believe there were five days of pleasure left. It was truly extraordinary that the brothers had become so close in such a short space of time.

After what seemed an eternity, the bell rang and Simon drove to the library, as he hadn’t had time to study all week. The next 5 hours were pure hell as Simon tried to learn a series of boring facts about World War II. Finally, he drove home, smiling as he eyed Caleb’s Toyota in the driveway.

Simon rushed into the house, throwing clothes everywhere as he rushed up the stairs to Caleb’s room. As he bolted through the open door, there was his stud brother in his blue silk boxers and nothing else. Caleb had taken his cock and balls out of the fly slit and was stroking himself slowly.

Simon quickly stripped to his own solid blue boxers and pulled his rock hard prick and balls out of the demetevler escort bayan fly. He got next to Caleb and started stroking his hairy chest. Caleb in turn pinched Simon’s nipples until they were hard nubs against his fingers. The two men enjoyed their erotic titplay until Caleb abruptly stopped his gentle massage of Simon’s nipples. Bending over Simon’s crotch, he stuck his tongue out and made contact with Simon’s balls.

“Oh my God, man, that feels so good!” Simon closed his eyes contentedly.

Encouraged by Simon’s approval, Caleb stuck his broad tongue back as far as it would go. He bathed Simon’s balls with spit as his younger brother groaned into oblivion. After two exquisite minutes of ballplay, Caleb moved up to Simon’s prickstalk. He took the head and a good three inches of shaft down his throat in one gulp as Simon let out a loud groan. Then he deep throated his brother like a madman, delighting in Simon’s moans and grunts. Although Simon tried to hold back, the idea of being given his first blow job by his older brother was simply too much for him.

“This is it-t-t-t-t-!” Simon started to shoot off in Caleb’s mouth a solid six spurts of cum. Caleb swallowed it all eagerly, loving the slightly salty almond taste. At the same time, his own cock exploded all over the bedsheets. The two brothers lay silently for a good minute, each too amazed to speak.

“That was awesome!” Simon finally managed to get out.

“No, you’re awesome!” Caleb embraced his brother strongly, never wanting to let him go.


The fifth day of Hanukkah was a Saturday and as it worked out, both Caleb and Simon had made plans for the day. Caleb was going to a local amusement park with some friends while Simon was doing the local Mall circuit with Jacob Finkleberg. It was just as well, as the brothers needed a little time apart to prepare for the nights activities. Simon had a funny feeling he was going to lose his cherry butt to his brother and was excited but a little worried at the same time. He’d only seen one gay video and it looked like the guys were in pain as they were penetrated. Simon knew that Caleb would never want to him to be in any discomfort, so he wasn’t too concerned. Still, it was definitely going to be a night to remember!

Simon managed to actually enjoy himself at the mall with Jacob, who was absolutely clueless as to what he was doing with his brother. And Caleb had a reasonably good time at the amusement park, trying not to think of Simon too much, as he got an instant erection. In due course, dark followed light and the brothers arrived home at the same time, about eight o’clock.

Simon followed Caleb by about 5 minutes. When he walked into the house it was completely dark, save for a light coming from Caleb’s room. Simon set a speed record getting to his brother. To his surprise, Caleb was standing in the doorway, wearing a grin and a towel and not much else.

“What….?” Simon gave Caleb a goofy grin.

“Thought we would take a shower together, what do you say?”

“Sure!” Simon was pleasantly surprised. He practically ripped his clothes off as Caleb dropped his towel to the floor. The two brothers took in their naked bodies for the first time. Caleb had a moderately hairy chest, with a cute pleasure trail leading to his navel. Simon was a bit smoother, with sparse hair on his chest and legs.

Caleb led the way to the large shower and Simon quickly followed suit. In a manner of seconds the spray of water hit their well muscled bodies as Caleb soaped up his younger brother. Simon in turn, soaped up Caleb, eventually dropping to his knees. He looked hungrily at his brother’s magnificent prick, then took the dickhead in his moist cavern. Caleb groaned and grunted as Simon sucked him off like a pro (he has been practicing with a banana for months), trying not to cum as Simon got progressively deeper and deeper. After a few minutes of extreme bliss, Caleb reluctantly pushed Simon’s head off his pulsating cock. He gently pulled his brother up and turned him around. As if on cue, Simon offered his virgin asshole to his one and only brother. Caleb soaped Simon’s asscrack generously, then inserted the head of his cock into his brother’s waiting hole. Simon let out a mixture of a groan and a scream as Caleb penetrated him in one quick thrust. Then, the older man screwed his younger brother with infinite gentleness, taking him one easy inch at a time. Simon felt a little pain at first, but as Caleb started to massage his prostate, any aches and discomfort quickly turned into a burning pleasure.

As Caleb thrust his cock deeped and deeper into Simon’s bowels, both men swore up a storm under the rushing water. At one point, Caleb reached around and started jacking off Simon’s cock vigorously. That was enough to bring them both over the brink.

“I’m g-going t-too p-op!” Caleb screeched.

“J-j-j-j-j-esus!” Simon groaned as he felt the amazing sensation of Caleb’s cream blasting in his butt. At the same time his own cock started to spasm all over the shower walls. The next minute was mind boggling for the two brothers as they seemed to orgasm forever. Finally, Caleb pulled his cock out of Simon’s butt with a loud plopping sound. He blew into Simon’s ear and the two brother’s exchanged long sloppy kisses.

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