A Holiday to Remember Pt. 03

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Can Jack Make The Right Decision And Save His Family?
7.7k words
4.58
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Part 3 of the 4 part series

Updated 06/11/2023
Created 12/09/2021
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Sinwriter
Sinwriter
259 Followers

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

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I pulled my Jag into a recently emptied parking spot, luckily I found one almost immediately. As any good American could tell you, trying to find a parking spot at the mall in December is a test of patience and the acceptance that luck sometimes exists. Once parked I got out and walked towards the entrance.

It was so crowded.

I spent the next half-hour simply perusing since I had no idea what to buy anyone, until eventually I settled on a few items, here and there. After going from store to store, I decided to take a break and stop by a Starbucks located inside the mall.

"Yes, I'd like a low-fat latte, medium, skim milk." I say as I placed my order and paid the woman at the cash register. After I got my drink I sat down and simply enjoyed the sounds of people talking and laughing. I could even hear the sounds of babies crying at the distance. I finally took a sip, enjoying that much needed caffeine when suddenly my eyes captured a beautiful sight, Hanna had just walked into the Starbucks.

Hanna wasn't alone, she had two young ladies with her, a taller blonde and a raven-haired shorter one. I watched as Hanna took off her white hat, exposing her straight, brown hair, it was neck length with streaks of blonde highlights. Her white hoodie clung tightly, accentuating her beautifully crafted body and showed me all of her feminine curves. The beautiful brunette had tight black leggings that showed me her toned legs and those brown winter boots all young women seem to wear. I studied her face just as I had the day I noticed her Tinder profile. She had perfectly shaped eyebrows that stood on top of her stunning almond shaped, green-brown coloured eyes. When she smiled she showed her deep dimples and perfectly strikingly white teeth. Her lips, rosy in colour had become a torture for me, I longed to taste them.

I continued to look at her until by chance she looked in my direction. I didn't break the look right away, I figured it would let her know I was interested in her, a few seconds later I finally did as I took out my mobile device.

I spent a few seconds looking at my phone, opening apps and then closing them, trying not to appear nervous when suddenly Hanna came over to where I was sitting while the other two teens placed their orders. I smiled as she got closer.

"Hello again." I say with as much of a masculine tone as I could muster.

"You're my neighbor right? the one with the really nice car?" Hanna asked me, it was the first time I've heard her voice.

"I am, it's nice to finally meet you. My name is Jack." I say as I extend an invitation for her to sit down.

"I'm Hanna." she said with a big smile and sat down. I was blown away by her beauty, despite my self-esteem being the way it is, I found myself feeling somewhat envious of younger men-- they all have literal perfection at their fingertips.

"Do you like cars?" I asked her, taking a quick sip of coffee.

"I like yours." Hanna said, then she cocked her head slightly left and smiled. "How old are you?"

"I'm sixty." I replied and hoped deep down that this wouldn't be a deal breaker. I wished harder than I ever had in my life.

"Seriously? You don't look it." Hanna said as I saw a slight blush.

I smiled and thanked her. I looked at her for a few seconds, quietly and without realizing I smiled again.

"What?" she asked as she tucked some hair behind her left ear.

"Oh, it's just that you're a true beauty." I said.

"Thank you." Hanna said as she locked eyes with me.

I smile when I see her bite her lip slightly. "You're welcome." I replied with a deep gaze, I let my eyes drop a bit and then brought them back up to hers.

That must've done something because after I did that she motioned for her friends to come over.

"These are my friends, Rylee and Tabby." Hanna said as she pointed to them.

"Tabby? That's a nice name... I mean to say they both are." I add and then shake their hands.

I now began to pay attention to both the women that had just arrived. My eyes first focused on Rylee, she was taller than the other two, I'd say about five seven. She had on these gray, tight leggings that accentuated her amazing legs, a reddish sweater and a multi-coloured scarf; she also had blue eyes and wavy, strawberry blonde hair. She had full lips and appeared to be covered with lip gloss since they had a slight shine to them. She easily had the bigger pair of breasts compared to her two companions.

I then looked at Tabby which I figured was probably short for Tabitha (Hey, I get it, I am not a fan of my given name either which is why I prefer Jack). Tabby was easily the shortest one of the bunch, which I'd wager was about five foot two inches tall. Tabby had her black hair tied into a messy, loose knot, she wore a black hoodie, slightly bigger than her thin frame required, black, loose pants that stopped short of her ankles, and white sneakers. She used black plastic glasses, had dark coloured round eyes, heart-shaped lips, and a beauty mark on her left cheek.

The three of them were very good looking, and they had a look of athleticism to them. So, I took a wild guess. "Cheerleaders?" I asked.

"How did you know?" Hanna replied.

"Just a hunch." I said with renewed enthusiasm.

"You know... you look very familiar." Rylee said. "Like really familiar."

"He does?" Hanna said, stepping in. "Well, he's my neighbor, maybe that's how?"

"No, I never forget a face." Rylee added and then took out her phone. After a few seconds she showed it to the other two women at the table.

"Wow." said Hanna.

"Okay." Tabby said then looked at me with new eyes. "You got a nice body on you for an older guy.

I simply looked at them quizzically, which caused Rylee to finally show me what she had on her phone. It was my Tinder Profile. I saw my name, age, and a picture of me shirtless, showing off my healthy, muscled physique.

"I saw this profile recently and I was like, wow, hot old guy." Rylee said as she put away her phone. "And now you're here."

"Are you all on Tinder?" I was curious, so I asked them.

The three women giggled together and thankfully our conversation flowed perfectly after that, none of that weird, awkward silence. I kept up my charm, throwing a few jokes here and there and making very carefully crafted lewd remarks.

Twelve minutes later...

"Oh shoot, my mom is asking if we're ready to be picked up?" Tabby asked suddenly while she looked at her phone.

"I don't know, are we?" Rylee asked, looking at her two friends.

From what I could surmise, it seemed that the ladies were willing to entertain me a little more, whether it be physical or not I couldn't tell, so I took the next logical step.

"I could always drop you ladies off, later, if you want." I said, shooting my shot, as these youngsters say nowadays.

"My parents aren't home." Tabby said to her two friends.

"Tabby!?" Said Hanna in a surprised tone as she looked at her friend and then at me.

"Hanna?" Rylee now asked.

The girls all looked at each other, some kind of silent body language that only close friends could possibly understand. There was a moment of silence.

"Okay, I'm game, let's go to Tabby's then." Hanna said and the other two agreed

Now, I often hear people my age complain about the open sexuality that today's youth seem to enjoy. I personally found it very silly to hear and never accepted it as such; anyone that is old enough to have experienced the 60's or the 70's would attest; but I do admit that it is a lot easier nowadays. As I pulled up to Tabby's home, I made the smart decision to not park in her driveway.

I suddenly felt as happy as a clam. I may have been jumping ahead of myself, but I went into her home optimistically, in my mind I was about to have sex with three very beautiful young women.

The house was all on one floor, the salmon coloured walls were appealing to the eyes, not too strong a color to choose. The living room was immediately to the right of the entrance, it had a wall mounted TV, a circular glass coffee table surrounded by a large, sectional couch of white/beige color. The floor was white marble that led to a long hallway. The kitchen was slightly to the left at the beginning of the hallway, the long hallway continued and at its end was Tabby's room.

As I was being led into the bedroom my heart rate shot up, I was suddenly very nervous, I have never been in a situation quite like this. It's amazing what some charm, confidence and good looks can do for you. I remember being in High School, I couldn't even get a first date. I was this scrawny, timid thing, barely noticeable. It wasn't until I met the woman that I married when all that changed.

I was lost in thought and didn't even realize where I was until I heard the door close behind me. Suddenly, this was all too real. I watched those three teens sit down on the bed. I looked at them, each one had something I loved, Rylee with her nice legs and her straightforwardness, Tabby with her demure physique and those big round eyes that hid behind those glasses, she looked so innocent. And of course Hanna, the beautiful brunette with a perfect smile and a killer ass.

Holy Fuck, what am I going to do? I've never even considered how I was going to please three women at the same time. I was so preoccupied with simply getting to this point that I never planned ahead.

I immediately smelled sweet perfume as I entered. The room itself was decently big. There was a big bed with white bedsheets and two white pillows, a closet to my left, a computer table to my right. The walls, unlike the rest of the house, were not painted with the pinkish hue, but with a light, blue tone instead. In fact, it was a nice touch.

All three of them were sitting down on the bed, looking at me, they suddenly appeared shy-- looking at each other. I felt a cold chill as I began to feel my chance slowly disappear. I needed to do something, otherwise they might chicken out.

Luckily, Rylee gave me that chance as she removed her sweater and her shoes, the other two followed her by doing the same.

Rylee had the biggest boobs of the three as her tight white shirt clearly showed me. Tabby's boobs weren't as pronounced as Rylee's, but she did have a slim, flat stomach that Rylee didn't have, and of course Hanna with that violin-type body of hers, pure perfection. In essence, I had variety, and I loved it.

I removed my coat, my sweater and my shoes. All that remained was my black t-shirt, my blue jeans and my white socks.

"Not bad, let's see more." Rylee said suddenly as she fixed herself on the bed causing the springs to make a loud noise.

I smiled, Rylee was making this easier for me. Honestly, I think I wouldn't even know where to go next, she was my guiding light at the moment. I took off my shirt, exposing my hairless chest to them, then I walked up and took Rylee's hand, moving her closer to me.

Her hands were cold to the touch and that caused me to slightly move back, it was an instinctual response.

"Sorry." I said to her and moved back. She took her time touching me.

Tabby moved closer and started to do the same, her hands were warmer at least. Hanna, that beautiful brunette looked at me but didn't come closer. I closed my eyes and let out a soft moan when I felt Rylee put one of my nipples into her mouth.

Within seconds they both went back to the bed. I honestly felt a little confused, was it a tease? Was it perhaps that they were afraid of being with a stranger, or each other?

I sat down on the bed between them.

"Is this your first time? I mean... is this the first time you girls are doing things together?" I asked.

"No, me and Tabby have messed around." Rylee said.

"You did?" Hanna asked quickly.

"Yeah, the Halloween party at Kyle's." Tabby now said.

"Oh my God." Hanna said as she now crossed her legs. "I never knew that."

I sat there as the girls began to tell Hanna everything about that night. The two teens told their friend that they had made out and performed oral sex on each other. I was happy simply being there, listening to this.

"We decided it would be a one time thing, and have never even talked about it till just now." Rylee said.

"I always wanted to try it... to be with another girl." Hanna said to her friends as a confession. That's when Rylee took the initiative, she put her hands on Hanna's chin, turned her face towards her and kissed her. That kiss turned into a deep, passionate kiss. When she stopped, Tabby followed suit, and that turned into a deep make-out session.

I used that opportunity and moved towards Rylee since she was easily the most receptive. I initiated a kiss, her lips were soft, our tongues danced and we touched our bodies, slowly it turned into a full make-out session.

I opened my eyes for a second and watched Tabby and Hanna, still at it, so I moved from Rylee's lips to her neck, nibbling, causing her to slightly moan. Then I removed her shirt and bra, exposing her pear shaped, C sized breasts with those pink hard nipples. I put one into my mouth while I used my thumb and index finger on her other nipple, twisting and lightly squeezing. As soon as I heard her moans slightly louder I moved south.

Her leggings were very easy to remove and in a few seconds her hairless, pink pussy came into view. I looked at Hanna and Tabby as their make-out session was slowly turning into more, Tabby had begun to touch Hanna's breasts.

I smelled Rylee's intoxicating aroma almost immediately, her pussy was already wet as I put my mouth on it. I licked and slurped, enjoying that sweet nectar. I could literally feel that cute blonde melt in my hands, her legs weren't as tense after a few minutes of me giving her labia the royal treatment.

I stayed licking Rylee's bare kitty until I saw Hanna so enthralled and lost in the moment that she didn't feel my hands going up her thighs, she was really into touching and kissing her friend. That's when I moved in, when she was distracted. I slowly moved away from Rylee and pulled down Hanna's leggings, pulling the underwear down carefully until I saw her nice pussy and her nicely cut pubic region.

I opened her legs slightly and put my mouth on that pussy, using my left hand to continue and stimulate Rylee. Hanna realized that it was me only after a few seconds, when she looked down, my eyes looked at her, I was enjoying that taste.

The beautiful brunette must've been more hesitant than I thought because she did try and push me off, I simply suckled and licked her clit faster.

"Oh my Gosh." Hanna said with a soft moan as I continued, finally relenting after a few seconds as her hips began to gyrate. I grabbed her hips with both hands now and put my tongue deep in. "Fuck!" She yelled as I kept eating her out. I licked that pink clit like you wouldn't believe.

Rylee came over, it looked like she wanted some. I loved how horny these women had suddenly become. As soon as that blonde teen began to lick her friend, I moved towards Tabby.

I pulled down her pants, exposing her pale legs, she kept her white, ankle sized socks on. Once her panties were off, I got a clear view of her tiny snatch.

I licked that black haired teens pussy just as vigorously as I had the other two.

I decided to take my time with all of them, I shifted from one to the other, they also took turns on each other. (Well, except Hanna, she didn't seem too keen on going down on her friends.)

I was determined to make sure they all orgasmed before it was my turn, and for fifteen minutes I did just that, Tabby was the first, I ate that pussy like a fruit, her slim ass on my hands, she was a quiet girl, barely a whimper as she came, but man did she shake. The blonde one with that firm ass was next, she was the exact opposite of Tabby, Rylee was a screamer.

By this point my pants were feeling a little tight, so I decided to get more comfortable. I stood up, undid my belt, pulled down my pants and underwear and pulled Hanna close to me. My mouth put in the work, I continued to slurp on her cunt like it was a gift of immortality from the gods. I watched as Rylee began to take care of Tabby, so I didn't feel rushed in any way.

Now, when I tell you that out of all the women I've ever gone down on that Hanna was the most I've enjoyed, then you can take that to the bank. Hanna had the most beautiful moaning sounds that I've ever heard. I opened and pushed those legs back, as my fingers now joined the action. I was determined to get that orgasm.

I fingered her sweet pussy, twisting my hand, massaging her clit with my thumb. I watched as her precious mouth hung open, spewing beautiful sounds of enjoyment from it.

"Ahhhhh, Ahhh, Ahhh." Hanna moaned as her hands tried to get me to slow down. All it did was entice me more as I curved my fingers. "Holy Shit, Oh my God! Oh my God! Oh my God!" She continued to say in quick, short cut breaths as I finally got my first orgasm out of her. Her legs shaked and then clamped shut.

I heard Rylee moaning loudly as she also appeared to have an orgasm, Tabby also stopped when the blonde began to writhe.

My hands were slowly getting tired, I have never worked as hard as I was doing, both my hands moving fast as my fingers penetrated those teen pussies.

"Ahhh, ahhhh, ahhhh" moaned Tabby, finally audible enough for me to hear.

"Oh my God! oh my God, oh my god! Ahhhhh!" Screamed Rylee as her mouth stopped licking Hanna's sweet cunt. "I'm going to cum! I'm going to cum! OHHHHHH, AHHHHHHH!" Rylee screamed as she had another orgasm.

Finally after another minute, Tabby had hers as well.

Now, all of them had orgasmed at least once and my erection needed the attention of those three teen beauties.

I helped Hanna to sit up on the bed, her hazel eyes looked at my hard prick as I stroked it right in front of her. She looked at it hungrily and almost immediately closed those beautiful lips around my veiny shaft. I was in pure bliss as I saw her bop back and forth, my cock slowly inching its way deeper into her mouth until it was about half way in.

"ohhhh." I moaned softly as that teen continued to please my cock with her mouth.

Hanna twisted her head around my cockhead causing each nerve cluster to come alive.

"Fuck, damn you're good at that." I say as she continued to impress me. That beauty was playing that skin flute like a pro, causing me to suck in my breath from how good it felt.

I needed to fuck her.

I laid Hanna down till her back laid on the bed, my mouth kissed her as I put my cock at her entrance, she was so wet that it provided all the lube I needed, in a few moments I entered her love hole, I thrust carefully as her tight cunt lubricated me. I could hear her sweet moans again.

"Wait... Wait." Hanna suddenly said, stopping me mid thrust. "Do you have a condom?"

I looked at the three teens. "No sorry, I don't."

"Nope." Said Tabby as Rylee shook her head.

I looked at them, realizing that no one thought of that. I took a deep breath and said with pure confidence in a trusting tone: "I am very good at pulling out, I promise I won't cum in you." I then moved my hips again, her sweet pussy tightened momentarily.

Hanna looked at me very worried, the others did as well. I continued moving softly as the bed began to creak under my movements.

"I can't believe I'm going to this." Said Hanna as she put hands over her eyes.

"Do you want me to stop?" I asked in earnest. "I don't want any of you to feel uncomfortable."

The friends all shared a look for a few seconds, my heart started to beat fast, I didn't want this to end like this, but what could I do? I was a literal stranger to them, I knew I was good for it, but how would they know that?

"You promise to pull out?" Hanna asked.

"I promise to pull out... Do you want to continue?" I asked.

Sinwriter
Sinwriter
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