‘tis the Season

I had what most might say was a "peculiar" childhood, as did my sister. And the best of times always came at Christmas, to nobody's surprise. We were spoiled but our parents made sure we never took any of it for granted, we worked for what we got, and helping the less fortunate was also a must. But things were always slightly different than most and this story is all about that and it is up to you to decide if that is a good thing or not.

As wonderful as that all sounds our parents demanded we go away for college, on their dime of course. I hated the idea but being two years younger than my sister l got feedback from her before diving myself, and her reports had me looking forward to going away.

It was Christmas break of my first year, so Cindy's third. And we were both heading home for Christmas when told our grandmother was joining us this year, the first year after Grandpa's passing.

Normally Christmas was there, at my grandparent's home. It was much larger than ours, but growing up in the same small house was the main reason our parents could afford the things they did. We always thought we would move into Papa and Nana's place but now that we kids are about to leave the nest for good, Dad and Mom figured they would remain in our home, no use for anything larger with just them two on the horizon. Because of their decision, Grandma set plans to sell the place and move into a retirement community the following Spring when housing becomes hot again. Why she chose to move to Florida would be understood before our break was over.

Dad picked us up, waiting two hours for my flight which got delayed but at least he had my sister to keep him company as her flight ran on time. With my bags in hand, l found my sister pointing my way, "There he is." Dad was happy to see me even if not in words. "Son"

It was like old times, my sister and l driving each other crazy. Our Dad back into form, "Don't make me pull over!" But there was no question, we all loved each other. l had a lot to thank my sister for, her help in turning a know-nothing average guy into the well-versed man l am now. Cindy wasn't the bashful type, nor did Mom come to think about it. It wasn't blatant but nudity wasn't a big deal around the house, no need for swimsuits when just us, and things like that. Everything was above board but yeah, l knew a woman's body without the need of Playboy magazines.

We enjoyed a nice meal and catching up afterward. Having run late we left our bags downstairs and it wasn't until l grabbed them to go to bed it occurred to me, what were the sleeping arrangements? Asking Mom half expecting her to say Grandma would sack up with my sister, in worse case she would tell me to sleep in her room and them in mine, as l still had bunk beds. But l guess granny poo-pooed that so l was to share my sister's bed with her.

I was tired and in no mood to argue so l just went along. I showered and climbed into bed in a fresh pair of boxers. l normally sleep nude but under the circumstances, l thought differently. My sister Cindy shortly followed wrapped in her towel and after wiping something on her face she tossed her towel across the chair and climbed into bed with me. I asked. "Naked, really?" which didn't go over well.

"What the fuck Brian, you haven't seen me naked before?"

"Well, seen you but never slept with you like that." l regretted saying it as it left my lips but there was no taking it back now. Thankfully she just rolled her eyes and turned over. So to make up for it for some odd reason l took my boxers off, tossing them across the room. "There, we're even. as if it some kinda contest to begin with."

Cindy did not react to this so l closed my eyes in hopes of sleep. I was just about there when my groaning sister backed her round ass into me, she didn't acknowledge my request that she moves to her side once again. She was asleep so l moved closer to the edge but to no avail, she just followed me once again leaving me behind hanging off the bed. Pressed against me caused my cock began to grow against my will, it was placed between her butt cheeks and the warmth felt wonderful. She finally grunted and then moved to her side.

I tried to sleep but my cock demanded attention and well with my naked sister next to me, it would be impossible to wash such thoughts away. I slowly began to stroke my cock and then needing inspiration l pulled the covers back just a bit, just enough to have a good look at my sister's breasts. Her body was like mom's, full and round in the right places. l stroke away with thoughts of them both, that was until Cindy woke up.

"Are you masturbating?" Before l could answer she pulled the covers back. "Holly Fuck, your dick is enormous!"

"Well, what can l say?" (returning to stroking) "Fuck, it feels good." (Cindy joins in, touching herself.) "Hey, Bro l beat l can come before you."

"Screw that, let's bet who can last longer. Say twenty bucks, what do you say?"

"Oh, you're on." (The two now masturbating.) "Hey, stroke faster. Like you were before."

"Okay, but you have to put your finger inside of your pussy. deal?"

The two change things up but both are still half-hazard. Cindy places her hand on top of her brother's. "Like this." (Stroking much faster.) In return he slips a finger on his free hand inside of her pussy, sharing the space with hers. "Oh, fuck." (She leaves her pussy to place both hands on my purple cock.)

"Oh, yeah. (Adding two more fingers to her box.) She begins to moan even louder, thinking she is close l picked up speed again. Just then she leans over taking his cock in her mouth, it feels so good bet be damned. "Oh, fuck yes. Just like that." l placed my hand on the back of her head, "Oh, fuckkkkkk."

My sister announced, "Told you." (While wiping the cum off the side of her mouth."

"That's right Sis, you win." We crawled under the covers and fell asleep.

l woke the next morning to his Sister riding me. "What are you doing?"

"Well, it was hard so why let it go to waste?"

"It's hard every fucking morning. Oh fuck it but we are even." (getting myself out of her debt) "Fine," She says in response and then begins to get their fuck on. Cindy comes twice and is well on her way to number three when the door flies open. "Breakfast you two," Grandma states before realizing what's going on. "Oh, Shit." We screamed in unison before diving under the covers. Grandma only closes the door without committing, this causes us to laugh loudly.

But then reality set in when we heard Dad's voice, we hurried out of bed thinking Grandma would be less likely to say anything in front of him. Mom with her uncanny sense asked what was wrong, but we held it together and the subject soon changed. We ate breakfast and then we were all going to the mall for some last-minute shopping. We returned upstairs to get ready to go.

(Knock-Knock) Granda: "l thought l would knock this time" (said with a grin ear to ear.) "Your parents are already in the car, we better get a move on."

My sister sat between Grandma and l, her short skirt made my pants far from uncomfortable. Sis noticed it, placing her hand on top of my raging cock only making things worse. Our parents piled out quickly, Grandma turned before getting out. "You'll have time for that later."

Sis and l went one way and the other in the opposite direction with plans to meet up in two hours no ifs, ands, or buts according to Dad. My sister and l finished in less than thirty minutes, after all we didn't have much money to spend. Some scented soap for Mom, a candle for Grandma, and some pipe tobacco for Dad. Splitting the bill on all three. So we stopped at the food court for a snack.

My sister teased me saying how she wished their hotdogs were as big as mine. l responded saying how mine cost her twenty bucks the last time so it seemed appropriate. After we laughed we ordered a pretzel and a chorro, splitting both.

On the way home Grandma seemed to carry on a conversation they must have started earlier. When she was done our Mom said. "Fine, Greg and l will go out tonight if that makes you happy."

"Great," Grandma said. "Dinner and dancing, I'm not unlocking the door until midnight." (As if they didn't have a key themselves.) She then winked at us. l wasn't exactly sure what that was for, something she knew about that l didn't, or maybe in regards to what happened earlier. Upon getting home we went our separate ways to wrap what we got at the mall. Afterward, we sat around shooting the shit before enjoying dinner.

Mom came down all dolled up, l had forgotten how good she could look. In fact, at first glance, l thought it was my sister. Dad was looking his best too, even if he would have rather stayed at home to watch the game. They left with little fanfare and that theme continued after they were long gone. We were not sure what Grandma was after but we were not going to make the first move. The night went on and although it was ten o'clock it felt like midnight to us at college on the West Coast. So we kissed Grandma and wished her a good night.

l went in for a quick rinse or l would not sleep well, l got about half done when my sister joined me. It was above board for the most part, but my mind should have stayed in there as it remained quite dirty.

We climbed into bed and it was as if she could read my mind saying. "Go ahead, but don't get any of it on me." I was needing to and my hand felt good sliding up and down my cock. A some point and before l came my sister turned and asked if l even had "That thing." (meaning my cock) in someone's ass.

"No, but I'm willing." said with a laugh attached.

My sister: "Well fuck, now I'm horny too." And with that, she joined me in masturbating. "Okay, but we can only touch ourselves." She added. But within two minutes she was stroking my cock as l fingered her pussy. l thought of earlier, touching her back door with one of my sticky fingers. She bared down on it welcoming it in. "Fuck yes, that feels so good." (As l finger fucked both holes) Then out of the blue, "l want to try."

"Try what." l asked.

"You know, anal."

Holly fuck l thought but l tried to keep my cool. "Well, if that is what you want." And with that l moved in behind her. I dipped my cock in her honey hole a few times before pushing the head of my cock in her tight ass. This only leads to her screaming for me to take it out. l told her how l was sorry and l didn't mean to hurt her. She confirmed how she knew and how it was alright.

Just then Grandma came bursting in. "Is everything alright?" I guess from hearing her screams, it was more shock to that than anything else, I mean she was standing there naked. l blurted out. "We tried anal and l hurt her." I wanted to take back the words as soon as l said them and by the look on my sister's face, she was in full agreement.

As for Grandma, she had no surprise upon her just asking how we went about it. I'm not sure why, and most likely because l still wanted to fuck my sister's ass. But l gave Grandma the play-by-play. "l see" she said and then she made a quick trip into the bathroom. "This isn't what works best, but it will work in a pinch." (holding a jar of Vaseline.) She went on, "Now Cindy my dear, did you want it?"

"Yeah, kinda."

"There was mistake number one, you must want it or your body will reject opening itself. And if you only use spit or body nectar it won't end well, not with a cock as big as your brother's. So let's try again." Grandma said.

"l don't think so." My sister said rejecting the thought, then expanding. "l mean l want it but I'm sore and you are here, and... l mean, some other time."

"And when will that be?" Grandma said. "When your parents are home, or when I'm not here to guide you?" She added. "Fine, now that you both got me all wound up l will show you both how to do it."

A bit shocked. "Grandma, do you mean what l think you do?"

"Yes, a hole is a hole, isn't it? Besides Grandma needs a good rogering." With that, Grandma got in the bed. "Now normally l would make you lick it before you stick it but we will move on. Now slip a finger or two into my pussy, this will help me get in the mood for anal." (Loud moans) "Okay Cindy, come sit on me and hold my cheeks open." Grandma moaned louder not only to the fingers working her pussy but to Cindy's warm and wet box on the small of her back.

"Now take a good dab but warm it in your hand first, cold closes the door." (louder moans) "Oh yes, just like that. Now give me a second finger, oh fuck yes, faster." (Pushing back against his hand) "Fuck yes, ask me if l want it, ask me!"

"Do you want it, do you want my big cock in your ass?"

"Oh, fuck yes. For years now."

Needing no more than that he pressed forward. Despite the size of his cock it slipped in with ease. "Oh my God, your ass feels fantastic." With his big dick pumping her ass and Cindy grinding her pussy against her Grandma screamed as a wonderful orgasm raced through her body. "Oh damn, l needed that. You can come when you're ready." Grandma informed me.

"No, wait." My sister screamed. "l want to try again." With that and following Grandma's guidance l was pumping my sister's ass with ease and to the delight of us both. I tried to hold off, but l did. But l couldn't, leaving my sister short on completely satisfied.

Grandma jumped back in. "l got this" and before my unbelieving eyes, she began to eat my sister's pussy. Fuck, nothing in my life was as hot as this. Then just as my sister came we heard Dad and Mom returning, Grandma dashed for her room slamming the door behind her. In hush tones, my sister and l talked about what just happened not that we disapproved but it was surely a new high in the strange or what makes us different than most of our friends making it less of a leap in ways.

Because we went on and on the night before we both woke up late finding dad had already gone to work and mom upstairs getting ready for the day. We had to settle for cold cereal, finding Grandma still at the table. "Good morning, Grandma. We won't say anything about last night." l said, breaking the ice.

"Well, that might be a good idea with your father, but your mom already knows."

In a panic, my sister jumped in. "You mean you told her! Oh my god!"

"Yes, Dear. She might be your Mom which l get but remember she is my daughter and l would never keep anything from her."

Just then Mom entered the room. "Good morning, my love loves." As if nothing ever happened. Then she turned toward my Sister. "l have some Preparation H in my medicine cabinet, l use it once in a while when your Dad pounds my ass and it is sore the following day. But always far less than when Grandpa hit it, thankfully."

(With our mouths wide open Grandma put her two cents in.) "Yep, he was hung like a horse. And you did well by naming your son after him, he is surely a chip off the old block. Or should l say cock?"

Mom's focus turned to me. "Congrats, Big Boy." Then just like that the subject changed, like what was said was water off the back of a duck. l sure as fuck wasn't settled in my mind, but also not crazy enough to continue the subject. Not until l was able to process it a bit longer, say twenty years or so.

I got a chance to corner my sister, thankfully she was in the same state l was. But as the day went on it all became more acceptable to me, and not to me alone. In another quick moment, Cindy trapped me in a corner. "I want you to fuck Mom while l sit in her face." Holly fuck, l thought then. "Yeah, as Grandma watches." It was just a dirty thought for the most part, but as they say "Be careful what you wish for."

Our giggling caught Mom's attention. "What's going on over there?" No reply was given. Then Mom gave my sister and l a few tasks that would keep us busy for a good hour or so. After that, she asked Grandma to join her upstairs. Grandma did not answer but her crooked smile spoke volumes as they climbed the stairs together.

Five minutes later my sister asked. "Are you thinking what l am?

"Yes, shut off the vacuum for a second." She did and with it quiet now we could hear muffled moans coming from upstairs. My Sister said "Fuck this," and then began sucking on my cock. Fueled by what was going on upstairs l quickly came in her mouth. "Wow, that was quick." She said, then she kissed me hard on the mouth. At first, l tried to pull away but she was having none of that, or l guess her determination was stronger than mine. And she was right, a moment later I'm looking for more of that salty treat. I licked and finger-banged her to what was also a hasty finish, and then we went about finishing our chores.

Mom and Grandma came back down shortly after that, both looking like the cat that ate the canary. (in unison) "What?" Nothing more was said but if their minds were rushing like mine was, all of this was far from over.

With all that Sis and l claimed to be tired and retired early that evening, l clicked on her stereo to cover for us and we went straight at it. Gone were the games as well as the shyness. We fucked and sucked well past midnight, and hopefully, none of the rest were in the know.

Even with that, we made it down to breakfast this time, maybe because of the need for fuel after such a night. After Mom kissed Dad goodbye she reminded all of this how this was his last day of work before Christmas and our return to college. I don't know if she meant anything more than information with that but l had my take on it, one l wasn't going to let slip between my fingers.

Mom resorted to what worked before, giving us chores to keep us busy before heading upstairs with Grandma again. But we were having none of that, not to her knowledge we weren't. We waited until the soft moans began again, this time taking our flight up the stairs. We stopped at the door where my sister asked. "Are you sure?" l slipped my hand in her P.J. bottoms finding her pussy soaken wet. "Yes, I'm sure."

With that l slowly opened the door finding them both on the bed. Grandma was over my mom, both locked in a 69. But l guess the movement of maybe the sound caught Grandma's attention, but she only smiled and then winked before returning to Mom's pussy.

Mom was blind to all of this with Grandma having her pinned down by her wanting pussy, Mom with no struggle given. We watched side by side, that was until Grandma turned her head taking my cock in her mouth. Maybe for cover or just want, my sister took over and began eating out our Mom. She stopped momentarily only to wave me in for a kiss, her mouth filled with the taste of Mom.

That was the pin, there was no stopping now. I peeled my sister away and Grandma gave way, sitting upright on Mom's face. l moved forward dipping my hard cock into Mom's wanting pussy. Maybe still lacking sight there was no doubt that she knew exactly what was happening. (Moaning) "Oh, Honey. l have wanted this for so long."

With that Grandma gave way which made it possible for my sister to fulfill her desire, she climbed up in the bed and slowly lowered herself until her pussy met our Mom's wagging tongue. As if they knew, Grandma took a seat in the corner working a dildo in and out of her worn pussy. But that was short-lived and now she was out of view.

Unexpectedly she began to tongue my ass, it felt fantastic and now l was all about not coming as it was pounding on the door from that point on. Fighting off the urge, thinking I'm on top again but just then, "Holly shit!" as grandma pressed her dildo inside of me.

Mom sensed l was close. "It's Okay baby, come in me, you can't get me pregnant." With her want and my need, l lost the battle, filling my Mom with copious amounts of cum. Mom licked my cock clean while Grandma and Sis took turns lapping up my cum as it escaped from Mom's well-pleased pussy. We all crawled under the covers for a well-deserved rest.