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CHAPTER 1: Three Years Later

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It’s been over three years since my Study Abroad program came to an end. I spent six months in England studying and traveling around Europe. I made lifelong friends along the way. I met an extraordinary babe named Gwen Edwards who showed me around. Gwen is a gorgeous British woman, now in her late twenties with blonde hair. Her breasts are mid-sized, nice and perky with clear areolas and cute nipples. She comes from a line of beautiful, curvy women. She’s not different, with an amazing ass! I met her on my initial flight to London for the first time. We hooked up on the plane and we’ve been close ever since. Especially since I received an invitation to join her and her incredibly wealthy family in an orgy. A family orgy they like to call The 2300 Gathering. I always smile when I think about each of those Gatherings I’ve been fortunate to attend. All the crazy sexual fantasies I got to live out with Gwen’s erotic family. Her relatives are some of the wildest, horniest people I’ve ever met. It was a bittersweet moment having to say goodbye to Gwen and her family when my study abroad program came to an end. I stayed in London an extra week while most of my other classmates went back to their homes. Gwen and her family hosted one last 2300 Gathering before I left. And let me say, it was definitely my most memorable orgy by far. We partied, fucked, and partied like never before. I had a hangover for two days after. It sucked at the time but absolutely worth it looking back. After I left England, I stayed in touch with Gwen. She would come to the States and visit me when she could and we always stayed in touch thru video chat, text, etc.

In present day, I graduated from university with a degree in Business and Marketing. I was job hunting for some time before Gwen bought me an airfare ticket to London to come for a visit. I got to see her and reunite with her family for another 2300 Gathering. It was the night before my departure back home to the States that Gwen offered me a job working for one of her father’s companies. A marketing position for a tech company with fantastic pay and benefits. The catch? I would have to move to London and reside in the city to launch my post-graduate career. Best believe I took her offer in a heartbeat! I went back home and packed up my belongings, said goodbye to my family, and moved across the pond to England. Gwen’s family bought me a loft apartment in the city. My place has incredible views of the city and the river! Working for her father’s company has obviously brought me closer to her and the family. It’s been almost a year since I’ve established my residency in England and worked for her father Don’s company.

Gwen moved in with me into my loft shortly after I settled in. We soon became official and started to date. She is someone I can see myself with long term. I plan on asking her the big question to marry me soon. Especially since Gwen is pregnant with my child. Gwen is almost seven month’s pregnant. We did a paternity test right away just to confirm that I’m the father of her child, due to our unique sex life. It was a surprise to find out she was pregnant. Not only because I am the father but because Gwen was on birth control. Her and the rest of the ladies in her family. They have to be due to their sexual conduct without any condoms. Regardless of the surprise news, we were happy. Gwen’s family was happy to hear the news saying I’m “officially” part of the family now. Truthfully speaking, I’ve felt like I was already part of the family when I was studying here in England on my study abroad. I was never close to my own family and mostly kept to myself once I left home.

With the summer season approaching, I found myself thinking about the next 2300 Gathering. It’s been MONTHS since Gwen’s family and I have had it. Gwen was busy with her pregnancy. Lots of medical appointments and checkups. Her father was usually away on business trips with her Uncle Fred. And the rest of the family had their own things going on. Gwen and I have been talking for the last few weeks trying to find the right time to plan the next gathering. We want to make it big and memorable since we haven’t done it in awhile. Gwen has asked me to brainstorm for ideas to figure out what to do since she’s busy. It wasn’t until her father Don made a HUGE investment that my brain hatched an incredible idea. An idea I’m more than confident Gwen and her family are going to love!

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CHAPTER 2: Mile-High Idea

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By the end of my work week, I was exhausted! I had a few big projects I was working on. I got a phone call from Gwen’s father in my office telling me to meet him and the rest of the Edwards at Gatwick for a family meeting after my shift ends. I tell him I’ll be there, and he arranges a private vehicle to pick me up and take me to the airport. I finish my duties for the week and leave the building with my briefcase.

“Hello Charles! I’m meeting the family at Gatwick,” I say to my driver, getting into the back of the dark SUV.

“Yes indeed sir! Mr. Don advised me to drop you off at the general aviation terminal. Traffic is light. We’ll get there in 25 minutes!” Charles says.

Charles gets into the SUV and heads over to the airport to drop me off. We get to our destination later than expected due to a construction delay. I arrive at the airport and make my way into the terminal, clearing security before heading toward the back where I see most of the family waiting for me.

“Finally!” Gwen says, coming up to me giving me a hug and kiss. Her stomach is large, revealing she’s in her final trimester of pregnancy.

Most of the extended family is here except for Aunt Margie, Granny Ellen, and some of the cousins. Don comes up to me and shakes my hand.

“Glad you could make it Luke! Let’s head out to the hangar in back. I have a surprise for the family,” he says.

Don leads the way with his wife Lisa behind. We all follow behind them leaving the small terminal and onto the tarmac. We walk to a large plane hangar adjacent to the terminal. I look inside the hangar to see a large aircraft sitting inside. It’s a completely silver Boeing 777-200ER, a wide body aircraft primarily used for long-haul flights. Commercial and cargo flights. This 777 plane is unique though, looking like a private aircraft, not leased by any airline.

Don stops the family and I at the front of the hangar.

“Ladies, gentlemen….allow me to introduce you to our upgraded private aircraft. It’s our very own luxury wide-body jet!” Don says holding his hands held high, showing off the beast behind him.

“Oh my!”

“Holy shit!!”

“Are you kidding??”

I hear Gwen’s family’s reactions, each of them staring at the plane. Gwen’s father then goes on to tell the family that he decided to sell all three of his small private jets and exchange them for an upgrade, big enough to house the ENTIRE family and then some! He said it’s a worthy investment and that the family will benefit from the plane being able to travel anywhere in the world all together.

The family begins to talk and ask Don questions, especially Gwen’s mother Lisa. She asked him if it was an investment worth having. Truth be told, I’m impressed! To say that the Edwards family is SUPER wealthy is an understatement. The man just bought his family a wide-body jetliner. Why? Just because! I’m more then happy to check out the inside of the aircraft.

Don eventually leads the family and I to the air stairs that lead up to the main cabin door of the plane. We climb up the stairs and walk into the luxurious jet and check out the interior.

The interior has 40 luxury lie-flat seats, 20 on each side of the plane with two aisles. In the front of the plane to the left of the main cabin door is the flight deck with a lavatory. On the forward right side of the plane is the main galley for the meals. Theres a bulkhead in the forward center of the plane that houses another lavatory and the crew rest area for the pilots and flight crew. In between the lie-flat seats on each side of the plane, is a open spaced lounge area. The lounge area has a large sectional couch that forms a U-shape, facing the back of the plane. The lounge area faces the mid-section galley and cocktail bar with built-in stools. Behind the mid galley and bar is a flat screen television with a long table and seats around the table for business meetings and dining. On each side of the dining table area are comfortable couches. In the back of the plane is an enclosed bedroom with a television, reclining chair and dining table. On the other side in the back of the plane are three extra lavatories with extra space. The entire plane is incredibly luxurious!

It isn’t until we get off the aircraft that I’m hit with an incredible idea. Don tells the family to prepare for a two-week vacation in Dubai. We’ll be taking this new aircraft to fly from London down to the Middle East for vacation to kick off the start of summer. When Don announces the surprise vacation to the family, I knew I had a great idea for the next 2300 Gathering.

I get back home with Gwen and share my idea with her.

“Baby? I think I know how we can make the next gathering incredible, like never before!” I say to her.

“I’m listening,” Gwen replies.

“We’ll be flying to Dubai for vacation in style! On our private jetliner! What if we have the next gathering on the plane?”

“Like….a mile-high 2300 Gathering??” Gwen asks getting excited.

“Yeah! We can try to schedule our flight around 2300 hours to commence the gathering in the air! On our way to Dubai!” I say with enthusiasm.

Gwen thinks about it long and hard for a few moments. I can tell see really likes the idea.

“You know what babe….I think you’re on to something! Let me talk about it with my father and see what he thinks!” Gwen says, reaching over to me for a kiss.

I’m excited just thinking about a potential orgy in the skies! It would be an incredible experience and something to always remember. A few days go by after Gwen discusses the my idea with her father. He approved my idea right away and began to work out the plans to make our next orgy happen in the skies. I felt honored to not only be a part of the family but to also be able to have a say in one of the family traditions, discussing ideas and planning the next gathering. I’m no longer just “Gwen’s guest.” I’m part of the family.

The first thing Don and I do is set up the date and itinerary for our flight to Dubai from London in a couple weeks. Don is able to get a time slot for the family plane to depart from Gatwick at 22:15 hours (10:15PM), which should get us into Dubai by 08:30 the next morning local time. Next, Gwen and I find a private flight crew to hire and work our flight. Gwen reaches out to her friend Riley who’s a Flight Attendant for a corporate airline. Riley has joined some of the gatherings in the past and I’m excited that she’ll be most likely joining the family and I on the flight over to Dubai. Riley is a sexy trans British woman with short blonde hair, firm medium breasts, big ass, and a small cock. We’ve had some great times together at a few gatherings, thanks to Gwen inviting her to join the family.

Riley happens to have quite a few connections and helps us find two pilots qualified to operate our 777 plane. She also helps Gwen and I find two other crew members to work the flight on our luxury jumbo jet. We reached out to Riley not because we didn’t know where to find a good professional flight crew to operate our plane. But because she happens to know crew members from all over the world that work for a variety of corporate and commercial airlines. Crew members that are not just professional and safety-oriented but also discreet. Discreet enough to sign nondisclosures to not reveal to the public about our family business. Like say, a wild family orgy onboard an aircraft. Riley chose two colleagues that are qualified to work the aircraft the Edwards family owns. She also found two off-duty pilots that fly 777 planes, willing to work the flight. It’s extra money for the entire crew to be made. But more than that, we want the upcoming mile-high gathering to be a wild, extraordinary event for the whole family to remember. Therefore, Riley extended the invite for the working flight crew to join in on the family fun after they all signed nondisclosures.

Don and I set up a meeting at his lawyer’s firm with the flight crew that will operate our flight to Dubai. Two pilots and three flight attendants, including Riley. She’ll be the Purser on the flight. They each sign the nondisclosure, agreeing to never speak of anything that happens on the aircraft from the moment they step foot onboard to the moment they step out of the plane. The two pilots that’ll be working the family flight to Dubai are named Steven and Laura. Steven will captain the aircraft with Laura as his copilot. Steve is a tall German man, White, in his early forties. He’s friendly and has a kind smile. Laura is an attractive Swedish babe, in her mid-thirties with pale skin. She wears business casual attire at the law firm that show off her busty physique. She has a tight light- colored blouse showing plenty of her cleavage to her medium-sized breasts. She wears dark tight slacks that hug her bubble butt. Her ass is thick in all the right places. Her eyes are green and she has long blond hair.

Besides Riley, the other crew members working the flight with her are Henry and Aries. Henry is a Black British man in his late twenties. He’s roughly 5’8 with an athletic body. Aries is a beautiful Arab woman in her mid-thirties. Though her body is hidden under her conservative clothing, I can tell she’s got a sexy body. She’s curvy with large breasts and a big ass. She wears a traditional dress and a hijab to the meeting.

After the crew signs the nondisclosure, the lawyer tells each of them that they’re more than welcomed to join the “family fun” on the aircraft. The lawyer doesn’t disclose the details of the 2300 Gathering to the flight crew but he doesn’t have to. Riley brings them up to speed after they all signed the paperwork to never speak about anything that happens on the flight to Dubai. I’m thrilled to know that not only the crew is ok with the taboo lifestyle the family has but that they’d all like to join in on the fun!

Gwen, Riley, Don, and I sit with the crew to discuss details about the 2300 Gathering. Gwen gives them a brief history of the family orgy and how Riley and I came to be a part of it. Both pilots, Steven and Laura, agree that they’d love to participate. The flight attendants, Henry and Aries, also agree to join. Riley discusses a plan to coordinate with the Captain the exact time to commence the gathering, once the plane is airborne.

After the family and I find the flight crew to work the flight, we begin to work on the other details for the flight and gathering. Gwen arranges for a professional cleaning crew to deep-clean the aircraft upon our arrival into Dubai. Don gives me the task to buy the “miracle pill” drugs for the men to take for the gathering. It’s a green and blue pill that enhances the sex drive of the men and allow them to have multiple powerful orgasms in short periods of time. Not exactly legal, but the family has connections to some individuals in the pharmaceutical industry that supply us with the enhanced sex drug for the gatherings. Gwen also finds a private aviation catering company with fine-dining meals to cater our flight to Dubai. The last thing we do is send out a formal invitation to the extended family for a mile-high 2300 Gathering. Most of Gwen’s family accept the invite and eagerly await the upcoming flight to Dubai.

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CHAPTER 3: Takeoff and Intro

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Two weeks fly by and the next thing I know I’m getting ready for vacation with the Edwards family in Dubai. More importantly, I’m ready for the next 2300 Gathering thousands of feet in the skies. Gwen and I have Charles pick us up at our loft to take us over to the airport. Traffic is light in the evening hours. Though the gathering is not in the familiar setting of the Edwards Estate that we’re used to, we still wear the same formal attire. I wear my silver suit with a navy blue tie and a white shirt. Gwen wears a white button-up shirt and a short black skirt with panty hose. However, Gwen won’t be participating this time around due to her pregnancy and being tired from not getting much rest the night prior. She’ll be in the enclosed bedroom in the back of the aircraft for the flight getting her rest. Though I’m a little upset she won’t be able to join in, I understand why she can’t. Gwen does reassure me that she’ll wake up horny at some point in the seven hour flight and expects me to cater to her needs. I happily oblige.

Gwen and I arrive at Gatwick. Charles takes a private access road with pre-security clearance to take the vehicle straight to the tarmac where the family owned Boeing 777 aircraft is parked, adjacent to the private terminal. Once parked, Edward assists with our luggage, taking them from the trunk of the SUV. He hands our bags over to the ground crew, taking all the luggage to load onto the bottom of the plane. Gwen and I walk into the private terminal to meet with the rest of the family in the lounge area for some cocktails. We have relax while we wait for the flight crew to arrive and do their safety checks onboard the plane. I make my way around saying my hellos to the family.

I make my way over to Gwen’s parents, Lisa and Don. Don gives me a hug telling me how excited he is for the trip and of course, the upcoming gathering. Lisa gives me a deep kiss on the lips wrapping me in her arms.

“So nice of you to organize all of this Luke! You’re an amazing addition to the family!” Lisa says, whispering in my ear.

Lisa is the definition of a MILF. She’s got a sexy body with large breasts and a big ass in her late forties. I thank her parents for the compliments and continue to make my way around. The males of the family on this trip include Fred, Roger, Sam, and George. Fred is Gwen’s uncle, her father’s younger brother. Roger is her cousin, roughly my age, Fred’s son. Sam is Gwen’s younger brother, slightly older than me. George is Gwen’s brother in-law, married to her older sister.

The females in the family on this trip are Ella, Abby, Marie, and Dana. Ella is Gwen’s younger sister. She’s in her late teens now, barely starting her final year of high school. Ella has a petite body with small breasts that are growing and a plump, small ass with curly brunette hair. Abby is Gwen’s older sister, married to George. Abby has a body of a curvy model with large breasts and a thick ass, similar to her mother Lisa’s. Marie is Gwen’s aunt, who’s married to Fred. She has a similar body type as Lisa, with smaller breasts. Dana is Gwen’s cousin, daughter of Fred and Marie and her brother is Roger. Dana has a fake tan, with medium length blonde hair, thick ass, and small breasts with freshly-pierced nipples that are see through while wearing her white shirt.

There are a couple of familiar faces missing from the family, Margie and Ellen. Margie is Gwen’s plumper aunt, Ellen is Gwen’s grandmother. Both have other obligations and aren’t able to join the family and I in Dubai.

Besides the family, there are a couple new faces that will join the family on vacation. Gwen’s brother Sam recently got engaged and brought his fiancé Yumi with him. Yumi is a sexy Japanese babe in her late twenties. She looks exotic, looking like a Hentai character. Yumi has pale skin, HUGE breasts, with a FAT ass! She has an hourglass body shape. Though I’ve met Yumi a handful of times, I haven’t talked to her much. And this is the first time she’ll be attending a gathering. I’m aroused staring at her, anxious to get my opportunity to fuck her.

Next to Yumi, there’s one more new face at the Gathering. Her name is Dora. Dora is a high end trans escort invited by the family to join them on their luxurious vacation. All the men, including myself, love having Riley, who’s also trans. I sat down with the men in the family to pick out an exotic escort to add an extra tranny to join in on the gathering. Instead of paying her in cash, we extended her the invite for a two-week all paid vacation to Dubai. And of course, an orgy on a plane. Dora is Italian, with a variety of tattoos all over her body. She has tanned skin, large fake breasts, a fake ass, and a thick six inch cock. She basically resembles a trans model with a Kardashian body. Nonetheless, I still look at her with lust. I know I’m going to fuck her on the flight.

About a half hour later, the flight crew arrives and get onto the aircraft to complete their safety checks. When the crew is ready for the family to board, an airport security officer escorts us to the air stairs on the tarmac. We grab our carry-on bags and walk up the stairs to board the plane in a single line. Once I’m onboard, I make my way across to the other end of the plane and down the aisle to the back with Gwen. I’m going to drop her off at her enclosed bedroom. Once there, I make sure she’s comfortable and secure her seat strap to her. For takeoff and landing, she needs to be seated in the recliner next to the bed.

“Are you good baby?” I ask her.

“Yes darling, I’ll call for you if I need you here. Have fun!” Gwen tells me with a big smile.

I kiss her and leave, closing the door to her bedroom and make my way back towards the front of the plane. I pick a random seat and sit down enjoying the generous space in my “cubicle.” It’s a lie-flat seat with a pillow and blanket ready for me. The seat looks just like a business or first class seat on a regular commercial airliner. Seated on my side of the plane are the males. On the other side, the females. The Purser of the flight, Riley, comes down the aisle and takes drink orders.

“What would you like handsome?” Riley asks me.

“I think I’m good for now. But I’ll have that ass of yours later on,” I reply, groping her bottom with my hand.

“Calm down there mister! I’m working and need to be professional!” Riley says, playfully shoving my arm back.

“Yes ma’am!”

Most of the family have pre-departure cocktails as I sit down getting settled in my comfortable seat. The lie-flat seats are arranged in a 2-2 configuration, with forty seats total twenty on each side of the plane. Seated next to me is Sam, who takes large swig out of his glass of whiskey.

“Dude, you’re a fucking genius for coming up with this idea!” Sam says to me.

“Ah, it was nothing. I’m sure someone else would have thought of this eventually. As soon as your dad showed the plane to the family, I was just reminded of my first encounter with Gwen. Which happened to be in a plane on our way here to London.”

“Whatever you say lad! You’re still a genius in my eyes!” Sam says with a chuckle.

Shortly after, Aries comes down the aisle with amenity kits for the men. She hands mine over to me with a wink. She looks sexy in her stewardess uniform with her dark hijab on her head matching her uniform. The female flight attendants wear a short black skirt with a red collared button-down shirt. Aries and Riley wear dark pantyhose, heels, and a black scarf around their necks.

I look inside my amenity kit and find a sleep mask, toothbrush with toothpaste, a bottle of lube, a small plastic baggie containing three “miracle pills”, and some other complimentary items. Aries makes her way around to hand out mini bottles of water for the men to swallow the pills. I plan on taking mine just after takeoff.

Riley’s voice then comes over the PA on the plane, announcing that the aircraft door has been closed and for the other flight attendants to arm all the other doors on the plane for departure. Captain Steven then speaks into the PA.

“Welcome aboard ladies and gentlemen! I’m your Captain, Steven, flying this luxurious bird with First Officer Laura. This is Flight 2300 with nonstop service over to Dubai! Our approximate flight time tonight will be 7 hours and 10 minutes with an arrival time of approximately 8:30 tomorrow morning, local time in Dubai. Weather is looking great to fly tonight, a slight chance of some light turbulence half way through the flight. I will get that seat belt sign turned off as soon as we reach cruising altitude. Once the sign is off, feel free to go about the cabin and enjoy yourselves! You have a fantastic crew in the back! Your Purser Riley with her team are going to take amazing care of all of you! So sit back, relax, and enjoy the ride!”

Riley, Henry, and Aries walk through and secure the cabin. They pick up drinks from the family, close the overhead bins, make sure everyone’s strapped in with seat belts. The plane is tugged backwards, away from the small terminal. The pilots start the engines up, as I hear them slowly come to life to begin our short taxi to the runway. I look at my watch and see we departed on time, 22:15. The 2300 Gathering is scheduled to commence in 45 minutes. By then, we’ll be airborne at our cruising altitude. Riley, Aries, and Henry perform a brief safety demonstration for the passengers in cabin. Riley took the time before to brief Gwen in the back of the plane in the bedroom, in case of any emergencies. The large jet begins to taxi to the runway. The flight crew in the cabin take their jumpseats as the Captain makes one final PA before takeoff.

“Flight Attendants, please be seated for departure. We have a short taxi and we’ll be airborne soon.”

The plane taxis to the end of the taxiway and turns slowly, as the pilot centers the plane onto the runway. We sit tight for a few moments, awaiting for the all-clear from Air Traffic Control. Suddenly the engines roar with monstrous power and the plane begins to pull forward. As the pilot puts the plane in full-throttle, the plane picks up speed accelerating down the runway. The plane begins its rotation and pulls up with the wheels leaving the ground. I stare out the window at the city lights, getting dimmer the higher the plane climbs into the clouds.

Some time goes by as the plane climbs towards its cruising altitude. I take a look at my watch. The time reads 22:45. Just fifteen minutes remaining until the gathering begins. Riley then makes a quick PA.

“For our gentlemen onboard, please take your pills. I will make an announcement in fifteen minutes to commence the 2300 Gathering, Mile-High Edition!” Riley says, earning an applause from the family.

“For everyone, please feel free to start undressing in your seats with your seatbelts still fastened.”

I reach into my amenity bag and grab a pill, swallowing it down with some water. It takes a few minutes for the effects to kick in but I feel my cock getting rock hard inside my pants with my heartbeat racing. My thirst for sex intensifies and I get fidgety, shaking my legs back and forth and moving around in my seat. The anticipation is killing me! With my seat belt fastened, I begin to strip out of my clothing. From what I can see, everyone seated onboard around me do the same. I unbuckle my belt and unzip my pants, using my hips to shake my lower garments to my knees. My blazer and shirt are easier to take off. It’s not long until I’m seated completely naked in my seat, as the plane continues to ascend. Riley then makes another announcement over the PA, giving the details of tonight’s 2300 Gathering.

“Ladies and gentlemen, welcome aboard! Just want to make some quick reminders before we begin this evening’s gathering up in the clouds!

First and foremost, due to our setting and environment, there will be some notable differences in this gathering. Remember to follow all federal guidelines and crew member instructions. The captain will keep the seatbelt sign off as long as he can but if we encounter moderate to severe turbulence, please be ready to pause all activity and take the nearest seat available and secure yourselves.

Refreshments will be available throughout the cabin in the lounge in the mid-section of the plane and the forward galley area. Please stay hydrated and keep in mind our high altitude.

All crew members and pilots, with exceptions, are invited to join the fun at any time. Please keep in mind that safety is still our top priority and be ready to stop all sexual activity with pilots and flight crew if and when we use our safe word ‘MAYDAY!’ Keep that in mind ladies and gentlemen.

Though the host of the gathering usually makes all the announcements, there are some changes due to our setting of course. Tonight’s official host and VIP finale to end the 2300 Gathering for the FIRST TIME EVER will be Ella!”

The cabin is filled with applause for Gwen’s little sister. It’ll be wonderful to have a new face for the finale. Up until this point, it’s only been Gwen, Lisa, Abby, Aunt Marie, Granny Ellen, and Aunt Margie who’ve been the VIP and hosts since I’ve started participating.

“That’s all for right now ladies and gentlemen. I will be back to start the countdown shortly!” Riley finishes with.

Finally, it all comes down to the final minute. 22:59. The plane has leveled off at cruising altitude about ten minutes prior. Riley coordinated with the pilots to turn the seatbelt sign off at exactly 2300 hours to commence the Gathering. The interior lighting in the aircraft is set. The sides of the plane by the windows have a dawn color hue while the ceiling lights up sky blue. Riley’s voice then projects over the PA.

“Ladies and Gentleman…the time has come for the commencement of the ‘2300 Gathering.’ Please remember that consent is mandatory, always stay hydrated, and of course…have a Happy 2300!”

“Let the 2300 Gathering commence in….

10

9

8

7

6

5

4

3

2

ONE!!!”

The seat belt sign almost immediately turns off with a high pitch chime. All passengers stand up and move about the cabin. The time has arrived and the party is just getting started.

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CHAPTER 4: Cousin Dana and Aunty

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Around me, I hear everyone undo their seatbelts. Some cheer out loud, ready to begin. I take my time getting out of my seat. I take the lube from my amenity bag and pour a generous amount onto my erect cock. Like a predator, I make my down the aisle searching for my prey. Looking around, I see most of Gwen’s family has started. Further down on a side couch near the dining and business table, Don has his daughter eldest Abby bent over fucking her from behind. Her massive breasts dance in motion as he pounds her. In the lounge area, Lisa rides her son Sam on the couch facing the bar. She winks at me when she sees me walk by. Adjacent, her young and petite daughter Ella rides her cousin Roger. The flight crew, still fully clothed, prep the bar area with refreshments. Seated at the bar is Gwen’s cousin Dana with a drink in hand. I rub my hands together and make my way to her.

“Hello Dana.”

“Luke!” Dana replies turning herself over to give me a deep kiss on my lips.

I feel her body up and down from behind her and pull back. I want to fuck her from behind on the barstool. Dana must have read my mind, seeing me stand back and rubbing my shaft.

“Why don’t you fuck me from behind mister?” Dana says adjusting her lower body so her plump cheeks are seated off the edge of her stool.

“You read my mind.”

I lean into her and kiss her neck gently, making my way down her body. Dana moans softly, using her hands to spread her lower cheeks for me. Her asshole looks nice and ready for penetration but I decide to find her slit. There’s going to be plenty of opportunities for anal tonight. I’m going to work my way up to it. Once my tip finds Dana’s slit, I easily push myself into her vaginal passage. Dana lets out a grunt with my cock sinking deep into her. She puts her hands in front of her onto the countertop and I begin to thrust slowly in and out of her. My left hand reaches for her breast and I grab it. I feel her firm small breast, playing with her nipple piercing. My right hand grasps her short blonde hair. I get a great hip workout as I fuck this bitch from behind.

“Yes! Fuck yes! Fuck me harder! Just like that!!” Dana shouts.

Riley looks over at me with a smile, continuing to set up the bar with refreshments for the family. I wink at her playfully as I fuck Dana picking up my pace. I eventually slow myself down, making small thrusts in and out of her pussy. I look at my cock each time I pull back. My rod glistens with lube and Dana’s wet pussy. I watch my rod get swallowed by her hole when I push my way back into her. Dana moans, begging for me not to stop. After a few minutes, I disobey her command and pull myself out of her. Dana looks at me with a look of disappointment on her face. There’s so much I want to do tonight with many sluts left to fuck.

“The show must go on,” I tell Dana leaning into her for a kiss.

She leans into me and kisses me lustfully, her lips locking into mine. I pull back and begin to look for someone else in close proximity. Aunt Marie suddenly appears from the back of the plane, walking into the lounge area. We look at each other and she smiles at me. I make my way to her and take her hand, escorting her to the sectional u-shaped couch.

We don’t make any small talk. Aunt Marie simply climbs into my lap when she sees me sit down on the couch. With her knees bent on the couch sitting over my body, Marie finds my cock with her hand and adjusts it to find her slit from behind her. I feel my cock slip in between her thick cheeks, finding her vaginal lips. Her eyes close and her mouth drops as my thick shaft sinks deep into her pussy.

“Bloody HELL!!” Aunt Marie shrieks.

I give her a few moments to adjust to my fat rod inside her snatch before I pull her upper body close to me. I do the work using my hips to move up, down, in and out of her cunt. Her shoulder-length dark hair falls into my face as she rides me on the couch. I shove my face in between her breasts and play with them, turning my head side to side in a motorboat motion. Aunt Marie screams that she’s close to her orgasm and sits herself upright. I lean back relaxing on the couch, allowing her to take over. With her knees still bent on the couch, she shifts her body up and down on my lap. She fondles her breasts with a big smile on her face, continuing to enjoy the deep penetration of my penis. Aunt Marie fucks me slowly, building up an orgasm.

Looking around, I see Ella next to me continuing to ride her cousin Roger. She lies forward leaning onto his upper body as his lower body moves up and down repeatedly at a quick pace. She moans out loud and makes eye contact with me as Marie continues to bounce on my cock. Ella extends her arm to me and grabs my hand. She squeezes my hand tight smiling while riding her cousin. Tonight will be her first time being the VIP at the end of the Gathering. Ella is now a young woman and will receive an anal cream pie from all the men, including Riley and Dora, to end the orgy. Next to Ella and Roger, Gwen’s brother Sam continues to fuck their mother Lisa. He now has her bent over on the couch fucking her from behind. Uncle Fred has joined the action and stands proudly behind the short couch in front of Lisa. She has most of his thick shaft in her mouth, sucking him at the pace of Sam’s thrusts behind her.

Paying attention to Aunt Marie, she rides me on the couch. I lean forward to grab her breasts and massage them gently. I take one of her globes and try to swallow it whole, making her moan louder.

“Just like that!! Yes darling!!” Aunt Marie shouts.

After a few minutes, her movements begin to die down and she lets out a deep sigh of relief, looking up into the heavens. Naturally, my cock glides in and out of her snatch, easier now that it’s soaked in her pussy juices. Marie had a long orgasm with her pussy convulsing, which I feel on my stiff rod each time she sits down into my crotch. When she calms down, Marie leans into me with a deep kiss, shoving her tongue into my mouth. We stay with our lips locked for a few moments until she grabs my broad shoulders to pull her bodyweight off of me.

“As always, GREAT JOB Luke!! I’ll see you around!” Aunt Marie says, walking away from the lounge area.

I sit back and relax for a moment, listening to the family having a great time fucking and sucking each other. The plane sails smoothly across the skies with the sounds of the roaring engines in the background. The night is young and I’m just getting started. I’ve fucked two of Gwen’s horny relatives already and haven’t had an orgasm yet. I’m in no rush though.

I look around and see that the flight crew is done setting up the cabin with refreshments. The male crew member, Henry, stands at the corner of the lounge looking at the family in full action. Riley sneaks up behind him, encouraging him to join in on the fun. Riley, the purser, is already stripped down naked. She’s been a part of previous Gatherings and is ready to participate. Riley has her tight skirt pulled all the way up to her upper waist, with no panties visible. Her small lady cock stands completely erect. She and Dora both took the miracle pills with the men, as they’re both fully functional trans women with lady cocks that can ejaculate when they each have orgasms. Riley’s red uniform shirt is no wear to be seen and she has her black scarf wrapped around her neck. We look each other at the same time. With a grin, she uses her pointer finger to signal me over to her.

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CHAPTER 5: Purser and an Asian Fantasy

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I meet Riley by the edge of the bar in the lounge. She takes my hand and escorts me to one of the comfortable passenger seats that lies flat into a bed. She kisses me with passion feeling up my body before pulling herself back from me with a big smile on her face.

“Do me a favor sir and pull this out for me. Nice and slow!”

Riley turns herself around and bends her body forward only the seat with her ass up high. I look down and spot a shiny object up inside her bum. It’s an emerald green plug lodged in her rectum. She shakes her ass for me in the seat with a giggle.

“You came prepared, huh?” I ask her with a chuckle.

“I always do! Need to make sure I’m always ready for a fat wanker up my arse!” Riley says with a cute laugh.

I take one hand and place it on her lower back and use my other to grab hold of the object. Grasping the plug, I slowly pull it out toward me. In no time, the entire plug slips out of her asshole. Riley groans, pushing her rectum outwards to gape her tight passage and have it ready for my cock to slide into. Riley hands over to me a bottle of lube. I use it to pour some more down my shaft and then some into her rear. Riley spreads her buttocks for me, ready to accept my manhood into her ass.

“Push the recline button on the seat for me dear and lie down. I want you to jerk off while I fuck you.” I tell her.

Riley obeys and pushes the recline button on the side of the seat. Once the seat is almost flat, she shifts her body around and lies on her back with the seat slightly inclined. She spreads her legs for me, shifting her lower body upward. I hold her left leg for support and use my primary hand to direct my cock below to her gaping hole. I rub my mushroom a few times on her perineum in between her arse and genitals. Slowly, I slip my tip into her welcoming ass, pushing myself against her sphincter. Riley lets out a deep grunt, as her tight hole swallows my cock inch by inch. At this point, her erect cock shakes softly on its own with precum dripping down her small lady cock. She’s so aroused, she’ll hit her first orgasm of the night in no time.

“Oh my!! Yes!! YES!! Fuck this tight asshole darling!!” Riley shouts in high-pitched squeals.

I grab both her legs and use my lower body to thrust in and out of her ass. I take deep, long strokes. I stab her with my sword slowly, not wanting to build up an orgasm for myself just yet. Riley begs for me to fuck her, stroking her erect penis. The lube is a tremendous help as I’m able to fuck her tight hole without any trouble. I slip out of her a few times but quickly guide my way back inside of her. I take one hand and begin to slap both of her firm breasts, one at a time. Riley likes it rough and I know it drives her crazy.

“I’m so close!!! Fuck me harder!!!” Riley yells.

I slowly pick up my pace, allowing my shaft to slide in deep as can be into her rectum. Riley furiously strokes her cock until I reach down to her crotch and take over for her. She immediately grabs her breasts and squeezes them firmly together. I thrust in and out of her against the reclined seat. With her eyes closed, breasts in hand, she goes quiet. Her cock erupts, spitting her seed onto my hand and onto her crotch. She releases about five powerful spurts of cum, making a mess all over herself. She takes deep breaths as I slowly begin to calm my tempo. Eventually, I pull myself out of her and stand up.

“Thank you darling! That was incredible!!” Riley says, sitting upright.

“My pleasure.”

I leave Riley and move on to find someone else. I walk by Henry who has little Ella bent over leaning against the lounge area bar. He’s currently half way up into her barely legal cunt with his dark meat. She screams begging for his big black cock to go in deeper. From what I can see, he’s at least eight or nine inches with thick girth. Across from them on the couch is the escort Dora with Abby. Abby rides her thick cock facing forward, shifting up and down with Dora spanking her plump cheeks from behind. The other stewardess, Aries, gives Uncle Fred a blowjob on the other side of the u-shaped couch. Her breasts are marvelous with big brown areolas and erect nipples. She’s completely naked with the exception of her hijab on her head and her uniform scarf.

I walk past the mid-section lounge and get to the long table with chairs around. I’m met with the sight of Dana and Yumi, Sam’s fiancé, on the side couch next to the table. They’re both in a comfortable position, scissoring each other. Their pussies mash together, back and forth, with each of them moaning in unison. It must be some hot and heavy lesbian fun as they’re each sweaty. I stare at Yumi with wide eyes, looking like a thirsty creeper. She looks better than I could ever imagine! She’s a Japanese Goddess! The kind of body anyone would expect to see in a hentai porno. Her breasts are huge, perfectly rounded with soft pink areolas and puffy nipples. Her curvature is perfect with a thin waist and a fat, curvy ass. She has long dark hair with bangs in the front. She has a cute button nose, stereotypical squinty eyes and juicy, plump lips. How did Sam find this perfect babe??

I walk over to Dana and Yumi and interrupt their session. Dana sees me first and stops movement.

“You want a turn with Yumi?” Dana asks, reading my mind once again.

“Absolutely!”

Yumi looks at me with a big smile and giggles.

“She’s all yours!” Dana says to me with a smirk, standing up and walking away.

Yumi smiles at me, as I extend my hand to her and help her off the couch.

“What would you like to do with me?” Yumi asks with a thick accent.

Thinking about it for a moment, I look around and see the table facing the flat screen television.

“Lie down on top of me on the table. I want you to sit on my face while you suck my cock.”

Yumi happily follows my instructions. I slide myself onto the tabletop and lie down on my back onto the hard surface. Yumi uses a seat to climb onto the table and turns her body around to face my cock. I’m blessed with the sight of her pale luscious ass. With her knees on the table and my body in between them, she slowly lowers herself onto my face. I take a deep breath for good measure and brace myself for Yumi’s round mound. She literally takes my breath away with her full weight on top of my face. My hands grab each of her rear cheeks for support while Yumi’s lips meet my cock for the first time in front of me. She grunts softly and lets my meat hit the back of her throat.

We lie on the business and dining table in a sixty nine position. Yumi sucks off my fat cock and I slip my tongue deep into her wet snatch. She has a trimmed bush but I don’t mind. My tongue dives into her slit and savors her vaginal flavors. It’s a fusion of her natural scent combined with what I imagine to be Dana’s vagina after their intense scissoring action beforehand. Yumi grunts softly, bobbing her head up and down my rod. She releases my cock from her mouth to lick my tip. She licks my tip for a few moments before putting my rod deep into her mouth, continuing to give me oral satisfaction.

My tongue ventures up to her tighter hole. I spread her cheeks wider for her arse to split open enough for my salivating tongue to slip inside. Yumi’s lower body shivers from the sensitivity of my tongue penetrating her asshole. As my tongue probes deeper into her tight passage, Yumi begins to rock herself up and down on my face. Asphyxiation settles in as I’m barely able to breathe with her fat ass on my face but I don’t care. I’m in lust with this busty Asian on top of my face, giving me incredible head. Her warm mouth engulfs about half of my shaft at this point and she shakes her head side to side. For the first time of the night so far, I feel an orgasm building up. I decide to build up the feeling just a bit more by thrusting my hips up and down on the table. My sudden hip movements forces Yumi to take the entirety of my penis in and out of her throat. I hear her gasping, desperate for air. I know she’s into this though because each time I lower myself back down onto the table, she bobs her head back down to leave my cock inside her mouth.

For about a minute or so, I continue to assault Yumi’s mouth with forced deep throat. I multitask and leave my tongue probed inside her asshole, doing my best to prep her for what’s to come. I knew I had to have her and do whatever I want. And what I want is to fuck this Japanese whore in her small asshole. My hips come to rest on the table and I pull my face away from Yumi’s ass. I lift her thick cheeks with my hands to speak up.

“Get up and lie flat on the table. I want that tight asshole of yours!” I tell her sternly.

“You going to fuck me in the ass with that big cock??” Yumi asks with a gasp.

“Don’t worry! I’ll be gentle….for now.”

Yumi gets herself off of me. She leaves to find a bottle of lube while I get off the table. She comes back shortly and lies back onto the table in between two seats. She spreads her legs wide for me and uses both her hands to spread her fat buttocks for me. In doing so, her anus splits open. Just enough for me to slip into her with enough lube. I pour some lube onto my shaft and then some down her lower vagina and ass. Yumi takes a few fingers to apply the lube to her tight hole and slowly fingers herself.

“Be gentle!” Yumi says with a smile.

I put one hand on her thin waist and take my other to guide my penis into her rectum. My mushroom presses against her hole and I slowly inch my body closer to allow her bum to welcome my tip. Yumi begins to wince and make high pitched yelps. Once my tip is shoved into her ass, I firmly push my way deeper into her especially tight hole. I feel her anal muscles squeeze my cock while I do my best to stretch her out and accommodate my manhood inside of her. I reach forward and grab both of Yumi’s massive breasts to feel them for the first time. I felt like a virgin all over again in her presence, fondling her soft, firm globes. Her puffy nipples are erect. Yumi moans each time my fingers pinch her nipples.

I stare at Yumi’s pale face the entire time I fuck her. I can’t believe I’m fucking this busty babe in the ass! Her tight hole is stretched now, taking most of the length of my meat. I pick up my pace, thrusting deeper into Yumi which each movement shoving my meat up her rectum. She begins to finger her hairy snatch, staring into my eyes.

“Just like that! Oh yes!! Fuck this ass!” Yumi cries.

I feel the sudden rush of adrenaline in my body from my crotch up to my face. My first orgasm will arrive shortly and there’s no going back. I don’t want to finish anywhere else at this moment except inside of Yumi’s asshole. With our bodies thumping on the edge of the table, I begin to slow my thrusts down. I want to make myself last just a little longer to enhance my orgasm. Yumi knows I’m going to cum for her. She begs for my milk, deep inside of her.

“Cum baby! Cum inside me! Cum inside my ass!”

There’s no going back. I succumb to my efforts in lasting longer and unload my mess deep into Yumi’s bowels with slow thrusts. I make sure my tip stays lodged inside of her tight hole as it spurts my seed deep inside. Yumi has her eyes closed and smiles bigger with each spurt of cum spitting out of my cock. It’s a powerful, long overdue orgasm. And I’m just getting started.

I only pull myself out of Yumi’s ass once I’m confident that my orgasm has subsided. Because of her position, it’s easy for my milk to spill out of her bum onto the edge of the table. I’m about to take my fingers to clean up the spill when I see Dana coming our way in the aisle. I point her over to us and she comes by to get a view of Yumi on the table with my cum dripping out of her ass.

“Eat her ass!” I say firmly to Dana, pointing at Yumi.

Dana licks her lips with a devious grin on her face, stepping over to us. I back away and make my way around the table to get the perfect view of Dana cleaning up my mess. Dana grabs hold of Yumi’s lower thighs before lowering her face down to the table to lick up my leftover semen on the table. Dana slowly glides her tongue from the edge of the table right into Yumi’s crotch. I hear her smack her lips, enjoying the flavor of my semen. She then pushes Yumi’s lower body upright to raise her bum. Dana shoves her tongue deep into Yumi’s asshole, beginning to push my creampie out of her back door. My semen spills out of Yumi’s ass into Dana’s mouth, catching each drop with her tongue. Once most of my spunk is released from Yumi’s arse, Dana swallows my entire load before cleaning up Yumi’s crotch with her tongue.

“Fucking Delicious!!” Dana says proudly.

“Gimme a taste!” Yumi replies.

Dana pulls away allowing her to sit upright on the table. Yumi pulls Dana in for a deep kiss. The two of them tongue and kiss each other with fiery passion. I leave them both and make my way back to the lounge area where most of the family is.

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CHAPTER 6: The Train and the Escort

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Don and Henry fuck Aunt Marie on the couch together. Don has his cock deep down her throat with Henry fucking her pussy from behind, spanking her. Henry still has his uniform shirt on. Sam lies on the other end of the couch parallel with his little sister Ella. He fucks her pussy lying down at a steady pace. Uncle Fred fucks Abby in the ass, lying on the floor with her on top facing forward. Abby’s lean and built husband George has the stewardess Aries on the floor riding his cock. Roger is by the bar drinking some water taking a rest break. Riley, Lisa, and Dora walk toward me standing by the bar.

“Hello darling!” Lisa says to me, embracing me with a kiss.

“Want to join us?” Riley asks.

“Sure thing! What’s the plan?” I ask in reply.

“Dora and I are going to run a train on Lisa with me sandwiched in the middle. Why don’t you join in on the action and make this train longer?” Riley asks.

It doesn’t take much for me to accept their invitation. I follow behind the three of them back to the dining and business table area. Yumi and Dana are nowhere to be seen. Lisa settles for a side couch that’s further than the table. She gets comfortable, placing her knees down in the center of the cushion, facing out the window of the plane.

“Where do you want it Lisa?” Riley asks.

“Put it in my ass darling! I want to be consistent with you and Dora!” Lisa says.

Riley gets behind Lisa, standing over her. She puts one leg up onto the couch next to her for support. Lisa is already lubed and ready to go as Riley slides her small cock deep into the MILF’s asshole. Lisa lets out a joyful laugh, placing both of her hands in front of her.

“Just like that darling! Fuck me! Yes!!” Lisa shouts.

Riley starts slow at first, waiting for Dora to get behind her. Dora splashes some lube onto her thick shaft and rubs it up and down. She hands me the bottle and I pour some extra lube onto my cock as well. Dora puts a hand onto Riley’s lower back and takes her other to align her cock with Riley’s gaping hole. Dora slides easily into Riley’s ass, beginning to thrust slowly. They both use slow, gentle moments to stay in sync and wait for me to add the final piece to the puzzle.

I look at Dora’s ass for the first time and see her rear is gaping too. She’s ready for my fat cock to slip into her from behind. I place my hand onto the back of Dora’s neck and use my other to steer my cock into this sexy tranny’s ass. I rub my tip on her perineum a few times, just like I did with Riley, and slip my helmet into her bum hole.

“Oh FUCK!!!” Dora screams.

I smile with pride. It’s music to my ears each time I get a first time reaction from a bitch yelling out loud, taking every inch of my monster. Pure eight inches with plenty of girth. At this point, I’m balls deep inside of Dora, feeling her warm and tight anal muscles squeeze my rod. Dora is deep inside of Riley. Riley is deep inside of Lisa. We have a train assembled and I slowly pull back to begin the ride. Dora follows my motion, pulling back with me. This creates a chain reaction as Riley pulls back out of Lisa. We start slow at first, trying to stay synchronized. I hold onto each of Dora’s ass cheeks for support as all of us thrust in and out, back and forth.

Lisa cries out loud, saying she can feel Riley deeper than ever inside of her ass. No surprise there thanks to the added body weight behind her with Dora and myself. Riley fucks Lisa, Dora fucks Riley, and I fuck Dora. We do the best we can to stay in sync but eventually we each go at our own pace. I focus on Dora, slapping each of her buttocks till they resemble a ripe tomato. All kinds of profanities, moans, and screams are let out from Dora, Riley, and mostly Lisa. We fuck in a train for a some time until Lisa hits an orgasm.

“FUCK!!! YES!!! ALL OF YOU MADE ME CUM!!!!” Lisa shouts.

Slowly we all come to a halt and I pull myself away from the three women. Dora pulls out of Riley and so forth. We catch our breaths for a moment.

“Luke! I almost came for the first time tonight! Literally as soon as that FAT PENIS of yours was shoved inside of me!” Dora says with a giggle.

“Well lets make that happen!” I reply.

I take hold of the escort’s hand and leave Riley and Lisa behind. We make our way to the other side of the table to another couch. I’ve seen enough porn to know all kinds of crazy positions. Recently, I saw a video of a guy fucking a tranny in a pile driver position. With her legs up in the air and her cock facing down toward her face, she stroked herself to an orgasm as he pounded her ass. She milked herself and aimed her cock to cum inside her own mouth! Feeling adventurous, I want to do the same with Dora.

“Get on the floor for me and put your legs all the way up. Lets see if you’re flexible enough to jerk yourself to an orgasm into your own mouth!”

“Let’s see how that goes! I’ve never tried that before!” Dora says.

Dora gets herself into position, placing her curvy lower body against the edge of the couch. She grabs hold of her lower thighs and spreads her legs apart before bending them towards her upper body. Looks like she is flexible! In no time, Dora has her body positioned with her cock aimed at her face just like the bitch in the porno I saw. I stretch my legs over her bent body. Dora is now in between both my legs and I take hold of my penis and shove it down to her gaped asshole. Once my tip presses against her sphincter, I lower myself down, shoving most of my meat back into her asshole. Dora calmly groans to herself, having adjusted to the size of my rod inside of her ass.

I thrust myself up and down on top of her as she begins to jerk off her thick cock. She grabs hold of one of her fake tits to massage it while I fuck her. I can tell she’s getting close to her arrival as her facial expressions constantly change. Establishing my dominance, I fuck this sexy trans whore, grabbing her from the bottom of her nut sack and squeeze them, firmly but not too hard.

“OH SHIT!!! FUCK!!!” Dora screams out.

I massage her scrotum, building up the sensitivity for her to enhance her orgasm as I pound her asshole. I begin to spit down onto her face to degrade her some more. She’s my bitch now and I get to do whatever the fuck I want. I spit on her, squeeze her shaft and testicles, continuing to push myself in and out of her ass until Dora lets out a deep growl.

“Aarrrraaggggghhhh!!!”

Dora hits an orgasm and begins to unload her cum onto her nose, cheek, and finally her mouth. With four or five gooey ropes of semen spitting out of her cock, she catches the last two shots into her mouth and swallows her load with a couple gulps. Once she’s done jerking off her cock, I know she has completely milked herself. I take that as my cue to slowly pull my fat rod out of her tight hole. I step to the side and allow her to bring her legs down and stand up.

“I needed that relief!!! Thank you so much!” Dora says to me, embracing me with a kiss. With our lips locked, she presses her tongue against mine. I taste her flavor as she has some leftovers on her wet tongue. We kiss for a few moments before I pull away.

“I’ll see you around,” I tell her with a wink.

I leave Dora behind to recover and make my way over to the lounge area for a rest break. Feeling dehydrated, I know I need some water after all the sexual activity so far.

TO BE CONTINUED……

Thanks for reading! I hope you all enjoyed! Part 3 and 4 were written together to conclude the series. Figured this would be a good stopping point due to the length of the story! Expect to see Part 4 this upcoming week! I do appreciate feedback! Please rate and leave a comment below if possible!

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