A December to Remember Ch. 03

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Matty, Cassie, Rachel and Sara enjoy a tropical vacation.
19.7k words
4.78
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49

Part 3 of the 3 part series

Updated 06/07/2023
Created 12/18/2015
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Nick54321
Nick54321
364 Followers

Author's Note: This is the final installment of "A December to Remember". It was incredibly fun to write and hope you all enjoy it. I do have big plans for this group and can't wait to share how everything finishes up. There is a still a lot of this story that hasn't been told and I thank each and every one of you for taking this journey with me.

Enjoy!

The deafening sound of jets taking off within close proximity seemed to come out of nowhere as I was patiently waiting for my sister Cassie, my girlfriend Rachel, and my mother Sara to make their way out of the limo. The bright lights of the terminal were buzzing as the sun was beginning to set and the temperature had dropped. We had arranged for a car service to drive us to the airport. Although the car service was handling the large luggage, the girls insisted on managing their own carry-on purses. After offering once, I could tell by their collective response that I had my answer and was not to ask again. Once they were settled we could go get our luggage checked and head through security.

One week in sunny Cozumel, Mexcio was just what the doctor ordered (literally). Ever since the four of us had decided to take a trip together, my mother insisted that we go to Cozumel. Nobody was in a position to argue with her as she was footing the bill for the entire week. Although my father Will had sold off his life insurance plan to provide for his other family, my mother still received a large settlement from her employer and was using it to 'spare no expense' for this week. It would be quite the change in scenery from wintery Northern Ontario to the sunny white sandy beaches of the tropical island. Although I was dressed for our destination, standing on the curb at the terminal in our current locale was not a pleasant experience.

"You ladies ready?" I asked to the group as I was hopping back and forth trying to keep warm.

"Maybe somebody shouldn't have worn shorts and sandals when it's January in Canada," My mother lectured me causing Rachel to snicker and Cassie to shake her head and smile.

"Nothing wrong with dressing for the destination," I said confidently as I started to slowly wheel my luggage towards the large sliding glass terminal doors. I could tell that the three of them weren't going to let me get away with this that easy.

"Oops, I think I forgot something in the back of the limo," Rachel stated in a joking tone. "I better go look for it before the limo leaves," she finished as she stuck her ass out while reaching into the back seat to pretend to look for something. Cassie couldn't pass up the opportunity to give her a loud slap and squeeze her ass cheek which almost knocked Rachel fully into the limo.

"OUCH!" Rachel squealed as she exited the limo rubbing her ass with a huge smile plastered on her face. Cassie made it up to her girlfriend by giving her a quick peck on the cheek.

"Who are you kidding?" Cassie asked with a raised eyebrow. "I've spanked you a LOT harder than that and you're always begging for more," she said as she turned to me and gave me a quick wink. The three of them started to giggle as they probably saw the look on my face get a little more excited. Rachel looked at me with a seductive glance and blew me a kiss.

"Your turn next time sweetie," she said as she winked and began to walk with an exaggerated swivel of her hips into the terminal. She was looking over her shoulder and grinning the whole time making sure my eyes were fixated where they were supposed to be.

Cassie and my mother were both smiling at her and rolling their eyes. Seeing the two of them laughing together and acting the same would always peak my interest. It's like you're looking at a perfect female specimen, and right next to her is that same specimen with a few more years and knowledge in her eyes. They're both drop-dead knockouts that would capture the attention of men anywhere they went. Rachel was their brunette counterpart who was the ultimate man's fantasy. With an amazing smile, gorgeous flowing brown locks, beautiful hazel-green eyes, and a body that was out of this world, I often found myself staring at her thinking 'I'm the luckiest guy in the world'. Her sense of humour and the fact that both she and Cassie were Harvard graduate students made her the perfect catch.

The four of us made our way into the relative warmth of the terminal and headed to the counter to get our boarding passes and check our bags. We had already completed the seat selection process and checked-in online prior to leaving for the airport. My mother offered to pay first class for all of us but Cassie, Rachel and I opted to sit in coach so the three of us could sit in one row and be squeezed in tight next to each other. Cassie and Rachel would also chat with anybody and thought maybe they could make some friends with people who would be staying at our resort. My mother opted for some peace and quiet and went for the full first class experience. We made it through the check in-line with the help of our car service and before you knew it, our bags were checked and we were on our way to the security check point. The line was surprisingly short and we were only a few people away from the scanners.

Cassie and my mother went through first without an issue. I swear they could have flashed a smile and walked on with a hand gun they were that persuasive and gorgeous. Rachel walked through the scanner and was permitted to continue through. Her purse when through the conveyor belt and I could see that the attendant had a strange look on his face.

He began to question Rachel about something that was in her bag. They were speaking in a whisper but I could only make out the words 'law enforcement' and 'just a toy'. It peaked my interest but it seemed to be an appropriate response for the attendant. She flashed her beautiful smile and he got out of his chair to hand her purse to her.

It was my turn to go through the scanner. I walked through after placing my watch and phone in the bin but the beeper still went off.

The attendant started with her wand and gave me a thorough look up and down.

"Sir, please remove your belt," the attendant ordered as she motioned for me to place it in the bin. As I was removing my belt I could see Rachel slowly nodding her head and licking her lips. Jesus I thought to myself. Taking off my belt at airport security was making her mind wander to places I didn't want it to go right then. I couldn't risk getting aroused going through airport security...That wouldn't go over well I don't think. I rolled my eyes and shook my head at Rachel but complied with the attendant. I threw it in the bin and walked through without any issue. I picked up my stuff and met up with Cassie and my mother who were already a grabbing a drink. We had about an hour before we had to board so a drink sounded like a great idea.

The four of us sat in the airport and talked about what excursions and activities we would like to do around the island. My mother was picking excursions that were all about relaxing. She suggested the occasional catamaran trip, spa day, etc. Cassie and Rachel on the other hand were picking things like cliff diving, zip-lining and shark-cage diving. It would definitely be interesting to see what we could actually do together as a group as I'm sure we all wanted our alone time as well. As we were finishing up our drinks we heard the desk attendant announce that all first-class passengers could now board the plane.

"Well I guess that's my cue," my mother stated as she got up and got her stuff together. "You three have fun in coach," she said with a wink. "But not too much fun," she finished as she pinched my cheek and walked away towards the gate. The three of us were staring at her tight toned ass as the blonde beauty made her way to the gate like she was a celebrity. We all caught each other looking and broke out into a fit of laughter.

"Ahhh this is going to be a GREAT week!" Cassie squealed as she embraced Rachel in a hug and a quick kiss on the lips. Rachel embraced her and hugged her back as I placed a hand on each of their shoulders.

"This WILL be a fantastic week," I stated. "The four of us are going to have a blast...trust me," I said as I gave them both a quick kiss on the lips which I could tell was not enough for them as their tongues were left hanging out of their mouths when I pulled away. The three of us chatted for a few minutes until we heard that our row could now board. We were lucky enough to be sitting in the second row which meant we were close to the front but had the camouflage of an extra row in front of us in case things got...inappropriate during the flight.

The three of us excitedly got up and were first in line to hand our boarding passes and passports to the attendant. After quickly scanning the boarding passes we were on our way down the jetway to the plane. The attendant on the plane offered us a friendly greeting and pointed us towards our seats. We had to walk through first class to get to our seats and couldn't believe the setup my mom had going on.

Each first class "pod" featured a fully reclining bed, TV, and ample space to store luggage. There were even individual dividers that could be closed for privacy. Complimentary drink service was offered and there were of course the warm hand towels that you hear about in the movies. The three of us had to stifle our laughter when we saw mom getting all settled in and cozy in her pod. She gave us an enthusiastic thumbs-up from across the aisle as we walked past her. We smiled and took our seats behind the partition wall in the second row. We were three seats in a row in the middle section while an aisle way and two more seats flanked us on each side. The girls opted to keep their purses under their seats as I stuffed my backpack into the overhead compartment. While I was making space up above, I felt a familiar hand rubbing against the front of my shorts.

"Take your time baby," I heard Rachel whisper as she subtly massaged my cock for a few seconds. I was trying not to think about it while I was making room, but I started to get hard anyways while she was working her magic. When I got the compartment closed, I shuffled over top of Rachel's lap and took my spot in the middle seat with Rachel on my left and Cassie on my right.

"Keep it in your pants until we at least take off Rach," Cassie playfully scolded her girlfriend. "Although It might be hard to keep it together that long," Cassie finished as she placed her hand in my lap and squeezed my cock. I nearly jumped out of my seat. The flight filled up pretty quick and before we knew it the attendant was doing the pre-flight safety demonstration as we were taxiing to the runway. It was hard to keep focused on the demonstration as the gorgeous flight attendant kept looking directly at me whenever she demonstrated inserting the seatbelt into the buckle. She had long flowing curly jet black hair and her skin was sun kissed to a beautiful light brown. She had that sexy sultry Hispanic look with big beautiful brown eyes and a gorgeous smile. I felt bad for staring but when I caught out of the corner of my eye both Cassie and Rachel staring at her too, the feeling of guilt was replaced with a feeling of excitement. This was shaping up to be a great flight.

About ten minutes later we were steadily ascending through the clouds as we reached our cruising speed and altitude. Rachel wasn't the best flyer and nearly crushed my hand she was squeezing so hard during take-off but had now slightly released her grasp.

The same flight attendant soon came by with a selection of goods.

"Would the three of you care for anything? Headsets, pillows, blankets?" she asked in an incredibly sexy accent that reminded me a lot of Henrietta. At that moment, I could actually see a lot of resemblance between her and our sultry housekeeper back home. I thought I was just making some type of crazy comparison and shrugged it off.

"Could we have three blankets please?" Cassie asked batting her eyelashes. The attendant smiled and leaned over Rachel and me to place the blankets on Cassie's lap. She seemed to hover over top of me for a few seconds before standing back up.

"Will you require pillows?" She asked in a playful tone.

"Nope, no pillows," Cassie answered with a smile on her face. "This is all we'll need...plus the drink cart when it comes."

"Sure thing Ms." The attendant replied as she smiled. "Drinks will be served shortly. Enjoy your flight," The attendant (named Maria) worked her way down the aisle occasionally looking back at our direction and smiling. My sister couldn't take her eyes off her.

"Does she remind either of you of Etta?" Cassie asked curiously.

"YES!" I cried out a little louder than I thought I would as both girls looked at me and giggled.

"Easy their boy," Rachel said as she patted me on the leg. "But yes, I think so too. She is absolutely gorgeous.

I couldn't pass on the opportunity to probe this further.

"You two think Henrietta is gorgeous too?" I asked, knowing full well that Cassie had kissed Etta at our dinner the other night. I wasn't sure how much Rachel knew about that or how she felt about it.

"God yes," the girls replied in unison as we all broke out into laughter. "We have thought about her a few times...when we were alone together," Cassie said. "I mean, when we weren't thinking of fucking you," Cassie whispered as she leaned in and licked my ear.

"You mean you weren't always thinking about me?" I asked in a sarcastic tone. "To be honest, I could swear that Etta is into me judging by the way she acts sometimes. It seems like she is flirting with me all the time," I finished.

"Wouldn't surprise me," Rachel said. "If she ever caught a glimpse of that massive cock I'm sure she'd be all over you."

I shook my head and laughed as I looked at my sister.

"True story," she confirmed as she nodded at me and smiled. The two girls cuddled in tight against me and draped the blankets over our laps. I could feel one hand from each side of my seat roaming over my lap under the blanket. My sister brought her luscious lips to my ear and gave me a little bit of a nibble. The combination of her perfume and the smell of the lotion on her soft silky skin made all my cares in the world disappear.

"I don't think I can wait until we land," she said in a sexy whisper. At that moment I could feel the belt on my shorts loosen. Two hands from two different women were acting like they were being controlled by one mind. The movements were flawless as they unzipped my shorts and pulled them a little bit down my legs.

"Just sit back and relax babe," came another whisper from the other side of me. I could feel Rachel's tits pressing against my arm as she inched even closer to me. "We know how to take care of you," she finished.

I could feel my cock start to get hard as they massaged it and pulled it out from the slit in the front of my boxers. The two girls would occasionally look at each other and smile. I could tell they were both getting turned on and at that moment I had wished that we were in first class so I could fuck both of them in one of those pods.

One hand was focusing on massaging my balls and shaft while the other was swirling around the tip.

"You girls know what you're starting here?" I asked as I looked at my sister and then at Rachel.

My sister bit her lip and slowly nodded while Rachel smirked and winked at me. The both of them continued to pick up the pace as my cock was now rock hard and throbbing under the blanket. I had closed my eyes to focus on the incredible pleasure these two were giving me when all of a sudden they stopped.

"Can I interest the three of you in a beverage?" I heard the sexy exotic voice of Maria ask out of nowhere. My eyes shot open and I found her staring down at my lap.

"Can we just get three rye and cokes and some extra napkins?" Cassie asked while making eye contact with Maria as she continued to stroke my cock.

"Most certainly," replied Maria as she began to pour the drinks. Rachel flashed me a wicked grin and continued to massage my balls with Maria standing right there next to her.

Marie made eye contact with the two girls and then looked me straight in the eye.

"Here are you drinks," she said as she placed them down on the tray table. "I'm glad that you're all enjoying the flight," she finished with a wink and a smile as she continued down the aisle. The three of us looked wide-eyed at each other after realizing that Maria seemed to knw what we were up to and seemed perfectly fine with it.

"Maybe we could ask for her...assistance with something," Rachel queried. Cassie's eyes immediately lit up.

"It's easy enough for us to do it under blankets, but how could we get her to...assist?" Cassie asked with a frown upon realizing that this might not be possible.

"Why don't we just finish what we have going on here and then we can strategize together. I can't really concentrate on anything else right now," I stated in a playful tone.

The girls giggled and started focusing all their attention back on to me. Perfect.

"Is this better brother?" Cassie whispered in my ear as she started stroking me long and slow. "Do you want your big sister and girlfriend to jack you off right now?" she asked in a sexy whisper.

"Are you going to cum for us right now baby? Is it hot knowing that we could be caught any minute and your mom is just a few feet away?" Rachel added in.

My sister grabbed a few napkins and brought them under the blanket.

"Do it brother. Cum baby. Cum for US!" she said in a louder tone as they were both feverishly stroking me and keeping the napkins around my tip to try and contain the inevitable streams of cum that were about to start shooting.

Rachel and Cassie both started sticking their tongues in my ears as they brought me to climax.

"ohh fuck," I whispered under my breath as I began to shoot stream after stream of cum into what I hoped was the pile of napkins. The girls never let up on stroking me and kept pumping it out of me.

Rachel was giggling now. "You're making quite the mess you dirty boy. It's all over my hand," she said.

"Yeah me too," Cassie mentioned as they began to slowly stop their stroking.

Rachel was the first to remove her hand. I could see that it was absolutely covered in cum. She quickly took her hand up to her mouth and sucked her fingers dry. Cassie followed suit and although there wasn't as much on her hand, she did the exact same thing and licked up every last drop.

I put my hands under the blanket to clean up whatever was left with the napkins. They had pumped a lot out of me but luckily most of it was contained on the napkins. I quickly put my shorts back together and decided to head to the bathroom to clean up.

I walked all the way to the back of the plane to find out that both washrooms were occupied. I peeked my head past the curtain to find Maria doing some paperwork and checking the inventory of meals.

Her face lit up when she saw me.

"Something I can help you with sir?" she asked as she waved me in past the curtain.

"Just looking for a g..garbage ," I managed to squeak out. "And a sink to clean up."

Maria smiled and offered to take my garbage from me. The napkins were soaked and I knew if I handed them to her that she may be disgusted at what was on them. Her hand was stretched out as she stood up and walked toward me.

"It's fine, please let me take it," she said in an almost desperate tone. I handed her the cum-soaked napkins as she rolled it in her hands for a few seconds before throwing it out.

I was blown away at the fact that she seemed to want it and actually played with it in her hands for a few seconds.

Nick54321
Nick54321
364 Followers