A Holiday to Remember Pt. 01

Dear reader:

This story will be a fluid continuation to the A Vacation To Remember series in which we get to follow good ol' lucky Jack's sexual adventures, this time enjoying the festive Christmas season with his loving family. In order to write this new story and also to continue Jack's exploits into a new ongoing series ( The name has not yet been chosen ) I will unfortunately need to make some minor changes. For example, I will need to remove the pregnancy from all future updates. I tried to continue the continuity but it just wouldn't work. I am sorry for those of you who liked that outcome for Jack, but I honestly believe that you'll still like the new adventures I have planned for this lucky S.O.B. So, with that being said, let's get to it!

All characters in this story are 18 years of age or older

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I came to a full stop as I heard my neighbor's truck backing out of his garage. While I stood there waiting, I decided to use that time wisely and catch my breath, putting both my hands unto my knees and slightly hunching forward. I take in deep, cold breaths and watch as the heat escapes my body via a visible, misty breath. I have gotten used to jogging in the early mornings, despite my age I have come to actually welcome it. It also helps to clear the mind.

As the peppered coloured haired man finally backed all the way out he took the time to wave to me. I waved back as I stretched slightly, it had become the usual for us to exchange the occasional wave or pleasantries since I take this route almost every day.

As I collected my thoughts I suddenly felt a gust of cold air hit me, sending a slight shiver throughout my whole body. I took that as an initiative to get back to my morning exercise routine.

There was another reason why I took this specific route on my way back home and that was because of Hanna, my neighbor's daughter. The teen had what you would call the typical girl-next-door look to her and normally I would have ignored her completely, moved on to other things, except for the fact that I had found her, by pure chance, on the app called Tinder; and that changed everything.

I had downloaded the app about two months ago, interesting enough I never used it, not once. That was at least until about three weeks ago when I suddenly felt lonely and desired some company. It was then that I found her profile as I was testing out the app's features. I hesitated at first, but eventually did swipe right. She, it would appear, didn't swipe back and that made me want her more, the woman who didn't swipe right.

"I guess it's true what they say, you want what you can't have." I say to myself as I keep jogging at a semi-quick pace.

Hanna lives two houses down from mine, as I approached it I slowed down. I would normally wait till she left on foot to school, giving her space, watching her nubile body from afar, using it as inspiration to keep myself in shape. But not today, today I was determined to make my presence known.

As the High school senior left her home, my eyes quickly locked on her. The sexy teen was wearing a short black winter jacket, a pink hoodie, those ripped jeans all teenagers seem to wear nowadays and white sneakers. I slightly increased my speed and once I was close enough slowed down as her heart-shaped ass completely caught me unawares. This was the closest I've ever been to her and without even realising it I found myself staring.

Luckily I managed to look up right as she looked back. I smiled at her and she smiled back.

"Good morning." I said as I slowly jogged past her, not slowing down. The last thing I wanted was for her to see me as a creepy old guy instead of the man that can and will provide her with unbelievable pleasures she didn't yet know existed.

"Finally... Now all I need is a bit of patience." I whisper to myself as I finally come to a stop. I turned around and saw Hanna looking at me while she continued walking. Her family had moved into the neighborhood while I was visiting Tim in the summer, so I wasn't there to introduce myself to them and missed a great opportunity.

I turned towards my front door. "All I need is a little patience."

After a nice warm shower I sit down and open up my laptop. I read through some of my emails, then pondered on whether I should pay my bills; as I tend to procrastinate a bit. I finally decide to pay those bills when I happen to notice a date of importance marked on my calendar.

19, December

Allie's plane lands at 20:39.

Tim's family comes in.

I lean back on my creaky wooden chair as memories of that amazing summer came flooding back to me, it was by far, the best two weeks of my entire life. I even went and asked my son Tim to come and spend the holidays with me, but for whatever reason he was hesitant; well, at least till my beautiful granddaughter managed to convince him.

Unlike Tim, I didn't need to do much to convince my daughter Allison, the moment I mentioned it she quickly said yes. In fact, I believe her exact words were: "Hell yes I am."

I smile as I lean even further back on my chair. That was the easy part, now comes the hard part. I have no clue what to get anyone for Christmas.

One week later

I stood there peering into that darkness, it always boggled my mind how it was just five forty in the afternoon and it was as dark as carbon outside. I took a sip of eggnog, then with a flick of the switch, that noble seven foot tall Fraser Fir came to life, illuminating that dark living room and turning it into a vibrant holiday setting. The colourful twinkling of lights, the sounds of holiday music playing and as soon as I lit it, the crinkling sound of the fireplace and suddenly my house felt all Christmassy.

Afterwards, I walk outside into that brazen, single digit weather with just a light sweater, jeans and sandals. Once I reached the end of my driveway I looked back at my house. It was dark, you could barely make out its features. "Let's change that." I say to myself as I walk back into the house, flick another switch, then return to the spot I had just come from.

My house had transformed into a Winter wonderland with bright lights on the roof and the lighted reindeer on the lawn that brought my two story house into clear view. The front door adorned with lighted Christmas ornaments, wreath and trim added to the scene. I haven't done this in a long time, I thought to myself as I simply stood staring at it for a few minutes.

"Aren't you cold?" said a feminine voice behind me.

I was caught so unawares that I simply breathed in deeper. "Yes I am." I say and then let out a small chuckle. I turn around to see standing just a few feet away from me, a beautiful middle-aged woman. "I'm John Rose, but everyone calls me Jack." I introduce myself and extend my arm for a handshake.

"Hi Jack, I'm Nora Miller. I moved into the neighborhood recently." she said to me and shook my hand.

"Oh yeah, I've been meaning to come by and introduce myself." I looked down and saw a small dog. "May I?"

"Yes, he's a softie." she replied.

"Boy or girl?"

"Boy, his name is Remington."

"Interesting name, what breed is it?" I ask after petting the small dog for a few seconds.

"It's a Boston terrier. It's not really mine, it belongs to my youngest." Nora said as her eyes looked at me with deep interest.

I honestly wish that I knew what women thought about whenever they looked at me. I have always been blessed with good looks, but I felt some of that would go away with age. It didn't, in fact, this year alone I have turned more heads than I ever did in the past, maybe it had something to do with me putting on some muscle.

I recognised her as Hanna's mom immediately, they looked very similar in the face with the same contour shape of the eyes and the same eye colour. Even the hair colour was the same shade of brown, just a shorter cut on the mom.

"You have kids?" I ask politely.

"Yes, I have two of them, Lily and Hanna." she replied.

I smile as I catch her fixing her hair on several occasions.

"And Mr.?" I ask carefully, trying to not appear too nosy.

"He's not in the picture anymore."

"Oh, I'm sorry, I didn't mean to pry."

"It's okay, it's been over for a while now." Nora said and smiled as she fixed her hair one last time. "Well, I have to go and start making dinner. It was nice meeting you."

"Likewise." I say as I return a smile. I watched her leave, just like her daughter she had a nice butt. I sigh, turn around and walk to my front door but before I reached it I saw a car pull into my driveway. I recognised it immediately, it was Tim's. I stood there and watched as it came to full stop. Once it stopped, the back door suddenly swung open.

"Grandpa!" screamed a very familiar voice. I watched as this blonde, five foot tall, skinny teen ran up to me and jumped into my arms, her slim, ninety pound body barely rocks me. As I held her, I inhaled her sweet smelling perfume greedily which caused her to lock her legs around my back. I made sure to compose myself and not do anything lewd in public.

After the long hug, she kissed my cheek and told me how much she missed me. I smile, kiss her forehead and put her down, then I walk towards the car, along the way Jen hugged me with the same vivacity that her teen daughter had just done seconds ago. "It's good to see you Jack." Jen says to me with a wink.

"It's good to see you too." I say as I grab her bags. I then proceed towards the white Mercedes SUV.

"Hey son." I say to Tim, we then proceed to give each other a strong hug. "It's good to see you." I say as I release the hug and grab some of the suitcases.

The warm, cozy house welcomed me. As I finally closed the door behind me, I could see why the Holidays was an experience better spent shared. Since my wife died, I have chosen to keep to myself, a lot. I missed the last two Christmases and felt a deep regret as I looked at my family. I took a step in, causing a slight creek on the wooden floor.

"Grandpa, I love your tree." Chelsea said with a big smile.

I looked around, the tree poised left of the fireplace, at a safe distance so it wouldn't catch on fire. The centre of the room had two large chairs and a brown sofa, it also had a sectional rug between them that for sentimental reasons I never got rid of. Both of the large chairs had throws on them.

Chelsea suddenly grabbed my arm prompting me to look at her. "Would you like a tour?" I ask.

"Yes, I would." she replied with both a look of an inquisitive nature and one of lust.

And as thus, I gave her a tour. I showed her the living room, kitchen and dining room, all of which were on the ground floor. Then proceeded to show her the basement and backyard.

The upper floor had all the bedrooms and two of the bathrooms. I showed her the master bedroom which is where her parents would be sleeping, the next room over would be hers and Allie's for the next few days and finally the last room would be where I would be sleeping.

"So I'm going to share a room?" The beautiful blonde teen asked as she looked around. "If that's the case, can I sleep with you?" she asked.

"I don't think that would be possible, at least not the way it is at the moment." I replied.

I looked at Chelsea as she got real close to me, I looked into her blue eyes for a few seconds then my gaze began to focus on her freckled nose and those sexy curved lips. I stand there like a total idiot, completely missing all the queues. Luckily Chelsea realised that I had no idea and proceeded to tip toe and pucker her lips. It was then that I finally realised what she wanted as I kissed her soft lips.

She wasted no time as she tilted her head and introduced her tongue into my mouth. Despite how badly I wanted this, I had to be extra careful and didn't give into the tempting thoughts of incest that rushed into my head.

After a few more seconds I finally break the kiss. That little minx looked at me with a more lustful look than she did before and winked at me before finally walking downstairs.

"That's trouble." I whispered to myself and followed her downstairs.

"Hey dad, where do you keep... never mind, I found them." Tim said from the kitchen.

"Hey Jack." Jen said as she approached me. She stopped in front of me and then squeezed my biceps and chest. "God, I forgot how fit you are. I can't wait to taste you again." she said, whispering into my left ear. I felt goosebumps all over as her warm breath hit my neck. "I can't wait to taste... you." she softly repeated as she kissed my neck then turned and left.

"Fuck." I again whisper to myself.

For the next half hour we all sit around the dining table and simply talked and laughed, catching each other up to the current state of affairs in our own lives. Chelsea was now in college, Jen took some time off of work and Tim got promoted to vice-president of his company. I congratulated all of them. That was when I realised it was time to pick up Allison from the airport.

"Tim..." I said as I stood up. "... can I use your car to pick up Allie?"

"Sure thing dad, keys are hung up, next to the door." he replied as he continued to joke with his family.

I walked to the front door, grabbed my coat, grabbed the keys and right as I was about to open the door, I felt someone grab my arm. I turned around and saw Chelsea.

"Wait for me, I wanna come too." She told me as she ran upstairs. In less than a minute she returned, she had put on a pink sweater, changed from jeans to leggings and tied her long blonde hair into a ponytail. "Bye mom, I'm going to pick up Aunt Allie with grandpa." she yelled from the door then quickly closed it behind her.

The car quickly came to life as I turned on its engine. I quickly check the mirrors, turn on the heat then back out of the driveway. I turned left, then right and before long we were on our way to the airport.

A silent car with two passengers always seems to cause a bit of apprehension to me as I keep thinking of things to talk about. I knew that it has been hard on her ever since she realised that she had a false positive on her pregnancy test a few months ago. Perhaps, a joke or two, or maybe an anecdote. I looked at her for a second and her eyes caught mine, she smiled and tucked some loose strands of hair behind her ear.

"How long till we get there?" Chelsea asked as she began to look around.

"Oh, about twenty minutes or so." I replied as I took a right turn.

"At what time does she land?" she asked as she continued to fix herself and squirm on the seat.

"Not for a lil bit, but I don't like arriving at the last minute." I said, taking my eyes off the road for a second. "What are you..." I began to ask but stopped when I saw her showing me her panties.

"So that means we have some time then." her sweet voice came to me just as those sirens had tempted Odysseus and his men on the voyage back to Greece. Suddenly, I felt an urge and a need to hold her, to feel her subtle warm skin, to smell her hair and taste her lips. I have had no sexual contact since I left Tim's house in the summer and I was indeed very horny.

I really wanted this, but my mind couldn't wrap itself around the fact that this wasn't my car.

"Chel..." I started to say but I quickly halted when I felt her hands on my leg. I took in a deep breath as I felt it move from my lower thigh to my upper thigh and then to my crotch. In what I can only describe as pure talent, that sexy woman managed to unzip and pull out my cock with no effort whatsoever.

I lost control momentarily of the vehicle when I heard a clicking sound, I realised that she had removed her seatbelt and I knew what was coming next. I was afraid of losing complete control of the vehicle and opted to be the more mature party member and put a stop to it. "Chelsea...." I said with a whisper. "...this is your fath....eeerrssss... ooooohhh sweet Jesus..." I trailed off for a moment as my cock found itself inside that blessed mouth.

Just concentrate on the road Jackie boy, you can do it.

But as I was about to turn into the freeway I heard a slurping sound and felt a quick suction pressure as two lips enclosed themselves over my engorged mushroom head. The beautiful eighteen year old began slowly working just on my cockhead with soft mews of encouragement.

"Ooohhhhhhhh.... God almighty." I say as I barely managed to pull over into an empty parking lot I found. I found myself closing my eyes as each time she nibbled on my cockhead I felt something like an electric shock of pleasure shoot up my spine. "Where dddiiiid... you... leaarrnnn... that?" I was barely able to put that sentence together.

That vixen blonde teen continued to only work on my cockhead, then I heard a loud popping sound as she removed her lips and tongue from my aching member. I looked down as her blue eyes met mine, she licked the cockhead, and very good I might add, then took my cock slightly deeper into her mouth. She bopped, slurped, twisted her hands, causing another series of pure ecstatic pleasures throughout my whole being. Finally, after a few more seconds she popped it as it left the confines of her wonderful mouth, then she started using her teeth to slightly bite it.

"The internet." she said with a slight giggle and went back to work.

"I've heard that before. Thank God for the internet." I whisper as I now found myself looking around to make sure no one was watching. Out of the corner of my right eye I saw her milky white butt and reached out to it, her pussy was wet to the touch.

"Are you ready?" she said as she positioned herself on top of me and in one slow, sweet motion introduced me into her tight sweet hole. I let out a low moan at the same time she did.

"Ohhhhh baby, I've forgotten how tight you were." I whisper into her ear as she lightly bit my neck.

"And I forgot how big your dick is." she whispered back then slowly began to moan as she began to move. I felt my cock melt with each bounce as the tightness of her teen pussy reminded me of why I had such an amazing summer.

I looked around again and saw no one as she began to breathe heavier. "God I've missed this." I say softly as her sweet moans becomes music to my ears. "Wow, baby." I whisper into her ear as I start to hug her tightly while she continued to work her magic, grinding away all that heavy tension I had bottled up.

Little by little I began to feel my strength ebbing away as the teen continued to entrance me with her new tricks, this time rotating her hips and twerking as she rode me. Our faces were inches from each other, I looked deep into her blue eyes, I felt her sweet breath as it hit my cheek. I observed her freckled nose and cheeks slowly begin to get rosier.

"Ahhhh, ahhhhh, ahhhhh." Chelsea began to moan louder as her mouth remained slightly open, it was beckoning me to kiss her. I proceed to do just that as I begin to kiss her deeply. "mhmhmhmhmh." I hear her moan as our lips remained locked.

I kept kissing her as she continued to grind and twerk, squeezing my cock.

"Mhmhmhmhmh, mhmhmhmhmh, mhmhmhmh..." Her soft, sweet moans continued to be constrained by my lips. Suddenly Chelsea stopped kissing me as she begins to ride me faster and faster. "Ahhhhhh, ahhhhhhh, ahhhhhh, ahhhhhh, ahhhhhhh, ahhhhhh, ahhhhhhh, ahhhhhh" she was now moaning louder and louder as I began to feel the SUV rock slightly.

We continue our exotic dance for a few minutes before I start to feel that pressure build up. I did not want to stop, it was feeling too good, I wanted more, I needed more.

"Do those seats lie down?" I ask as my own breathing is now beginning to get heavier.

"I am sure they do." Chelsea replied as she stopped grinding on me. She kissed me, then went to fix the back seats so we could head to the rear and lie down. I used every single second to regain my strength.