Sirs R&R 2- Jamaica
This is the second in a short series. The first in the series Sirs R&R (literotica.com/s/sirs-randr) gives the background and makes this story much clearer. Fundamentally Sir is old money, I have my own business that Sir wanted. The final result was I kept my business and Sir got me. Sir is busy all week long, flying internationally managing the assets he owns. He takes weekends off for some R&R, that is me.
On Wednesday I got a text from Sir - Be at the hanger by 1 on Friday, bring passport. The hanger is where his plane flies out of and of course 'bring passport' means we are leaving the country. I'm hoping for Paris again. I know not to ask. I text back 'clothes?' Hoping for a clue. The text I get back is not helpful 'toiletries and makeup.' That tells me that he is handling that side of the trip and I will be on display wherever we go. Sir's taste in my clothing is the minimal to be legal. I just know a couple things. What I'll be wearing will be expensive and designed to tastefully show off my assets. From experience I know that if I brought anything to wear, it would be left on the plane. The other thing I glean from Sir's terse message is that I will be back in time for the office on Monday.
My secretary knows that Sir and I are a thing. Fortunately, she has no idea what that relationship entails. She is not surprised when I tell her that Sir and I will be out of the country all weekend and probably unreachable. I see the message that goes out to all my direct reports that they are on their own that weekend.
I left the office midmorning on Friday, picked up lunch at a drive through and stopped by the house. I showered, shaved(again to be sure), and changed into a short dress that I hoped Sir would like. I lost my bra and suspender hose, there are never panties to lose. I switched to higher five inch heels. I grabbed my passport and large kit bag and headed for the small airport. My kit bag is larger than most since it must hold my enema kit. I'm also never plugged on a flight, because as Sir said, "it is necessary for the intestinal system to equalize pressure when at altitude." He translated that to "You'll need to fart when we are flying."
I got there around noon and was met by Sir's copilot. He had just finished filing the flight plan but was not willing to give any hint on the destination. He said Sir was on his way and we would leave as soon as Sir got there. Sir drove onto the tarmac and the pilot loaded both suitcases onto the plane. Sir parked his car and met me in the terminal.
"Ready for a wild weekend?" Sir asked.
"Yes Sir, where are we going? I asked.
Sir just smiled hugged, grabbed my ass, and kissed me. He held my ass as we walked out to the plane. The copilot helped us up the steps into the plane, closed the door and headed into the cockpit. Master and I strapped into our seats and watched as we taxied out and took off. Once we were at altitude all I could see below us was clouds. There is a display in the front of the cabin that sometimes shows a map of the world and the plane's location. It was turned off, I still had no idea where we were going.
Sir got up and fixed himself a drink from the minibar. He asked if I wanted anything, and I told Sir in a minute or two. When Sir sat back down, I unbuckled my seatbelt and slid down between Sir's legs, reached up and unzipped his pants and fished out his cock. I looked up at Sir and said, "This is all I need for now."
With my flights with Sir, I am a gold level member of the mile high club. A platinum level if you count the blow jobs I've give Sir and the crew members. Today I was happy to just kneel at Sir's feet, gaze into his eyes, and enjoy the feel of his cock in my mouth, on my tongue and then in my throat. Sir just sat back, relaxed, watched me, and let me enjoy myself, until he grabbed my head and held it steady as he filled my mouth with his cum. I opened my mouth to show Sir his gift before swallowing it. My first "Good girl" of the weekend.
I stayed between Sir's knees, licking and kissing his cock and balls, trying to lick up the small amount that I had spilled on his pants. Sir finally shifted and turned on the video display. "You may want to watch this. I put Sir away and zipped up his pants before returning to my seat. The video on the screen was from the camera over the pool during a weekend party where I had been the designated pool toy.
There is a certain detachment when you watch yourself being passed around in the pool. Which is not to say that it isn't hot as you watch yourself, sucking cock, sucking on tits, licking cunts, having your tits and cunt licked and sucked, and getting fucked. I saw Sir smile as my hand slipped inside my dress. I had been wet since Sir kissed me at the terminal and I was now soaked.
The pilot came back to get some water and told Sir that it was about an hour to touchdown. Sir thanked him then asked, "Would you do me a favor? My protégé' is very horny and she just drained me. Would you mind taking care of her for me?"
The pilot said, "My pleasure." Took my hand laid one of the seats down that turned into a bed, put a bar towel down, unbuttoned my dress, and slipped it off my shoulders. I might have been shocked the first few times that he and I had done this, but now it was just a break from a long boring flight for both of us. He laid me on my back, dropped his pants down, put my ankles on his shoulders and slipped easily into my soaking wet cunt.
He thoughtfully handed me another bar towel that I used to gag myself when the first orgasm rolled through me, the second wasn't far behind. For some reason the third one was the big one. I was loud even biting hard on the rolled up towel. Whether it was my muffled scream or my cunt clenching hard on his cock that pushed the pilot over and I felt him swell, drive hard and deep, and deliver shot after shot deep into my cunt. He sat on my tits as I cleaned his cock.
I thanked him. He pulled up his pants and handed me two more towels to sit on, not wanting me to leak all over his $15 million jet. He said something to Sir as he passed him on his way back to the cockpit. I put the towels in my seat and sat down still naked except for my heels. Sir smiled and asked, "Feel better?"
All I could answer was, "Yes Sir, thank you."
Shortly after that the copilot came over the intercom, "prepare for landing. Seatbelts please."
I thought about retrieving my dress but decided I could do that after landing. We approached over water and landed at a small airport. From the trees and foliage I could tell we were somewhere in the tropics, but still had no idea where. As the pilots were securing the plane, I retrieved my dress, the wet spot was far less noticeable.
A van pulled up to the plane and the pilot and copilot loaded the luggage into the van. The pilot sat in the front seat with the driver, Sir and I had the middle row and the copilot climbed into the back row. As soon as I heard the driver, I knew we were in Jamaica. No one else does the "No problem mon" like Jamaicans. The pilot handed all the passports to the gate attendant who stamped each of them.
About fifteen minutes later we arrived at the portico of a well know adult resort in Negril. While Sir checked us in, I wandered out to the pool to watch a game of topless volleyball that was going on. Much tamer than our pool parties.
A hostess took Sir and I down to our room. It was quite nice, overlooking the nude beach and the bay. She said sunsets here are beautiful. She explained that the "nude" side that we were on was clothing optional. The nude beach required that you shed your suit within fifteen minutes of arriving or leave. Coverups were required for meals in the main area or one of the special restaurants or if visiting the "prude" side. The pool I had first seen was the prude pool, and there was a major nude pool on our side of the resort with a swim up bar and hideaway grotto.
As she was leaving our suitcases were delivered. I was curious what Sir had provided for me to wear this weekend, but Sir was anxious to hit the beach. He unbuttoned my dress and took it, throwing me a small bag with a pair of flip flops, a broad brimmed hat and a tube of suntan lotion. He then spent the next fifteen minutes making every inch of me was well covered in suntan lotion. I then did the same for him, making sure his cock and balls were well protected.
We each grabbed a towel and our beach bags and headed out. There is nothing like stepping nude onto a beach with a couple hundred nude people. I had thought Sir's naked pool parties would prepare me, but it was nothing close. Even though very few people blatantly stared, it was obvious that most of the males and females were checking Sir and I out.
We found two empty lounge chairs, dropped our stuff and laid down. The lady next to me asked, "Just in?" I raised up to look at her, a 40 something with a boob job so new the scars were still red. "Yes, we just flew in this afternoon," I answered. "Be careful, use protection, stuff here from all over the world." She warned.
Through my dark shades I saw that I (we?) were being checked out by several couples, a few guys and a couple of ladies. Couples seemed to predominate. I was a bit surprised that no one approached us.
After a bit Sir suggested we go get something to drink. We took our beach bags and walked almost the entire length of the nude beach. While there were a few beautiful women, and some with the beauty of youth, for the most part, picture your local PTA meeting naked, all shapes and sizes. At the bar Sir got the local beer, a Red Stripe. I got another local drink, Jamaican rum and a local grapefruit soda called Ting. It was a nice combination I could get used to.
