Sirs R&R 2 Jamaica

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.

We wandered by the nude pool. Quite a bit of action, Sir's pilot and copilot both seem to have found a pool partner. One was riding the copilot's lap, not sure which hole, but both seemed to be enjoying themselves. The grotto seemed particularly busy, will have to check it out.

Once back to our room Sir wasted no time before laying me face down on the bed, grabbing a handy bottle of suntan lotion for lube and sinking into my ass with one long slow push. I wasn't sure if the added sting of Sir pushing through my ring was from not wearing a plug that day, or the use of suntan lotion for lube. But it only lasted a moment as Sir pushed the head of his cock through my ring.

Sir immediately started fucking my ass as soon as he bottomed out. Slowly at first, pulling back until the crown of his cock was pushing on the inside of my ring, and then deep until his hips were tight against my butt. After a few long slow strokes to make sure my ass had accommodated him, Sir picked up the pace. Sir was fucking my ass faster and harder with every stroke, his hips soon slamming into my butt, driving his cock hard and deep in my ass.

Sir didn't last long, too much stimuli from the nude beach and I would hope, my tight ass. Sir slammed in particularly hard and I felt him swell and deposit shot after shot deep in my ass. Sir collapsed his full weight onto my back, still deep in my ass, and whispered, "Good girl" in my ear as he bit and kissed my shoulder and neck.

Sir eventually softened and rolled off me onto the bed. I leaned down and cleaned his cock, learning I hated the taste of coconut suntan lotion more than strawberry flavored lube. Disregarding the horrid taste, I relaxed, laid my head on Sir's stomach and gently licked and sucked on Sir's cock.

I still had Sir's cock when he woke me up sometime later by swatting my ass. "Dinner time slut." While Sir calls me 'His R&R', slut is his favorite nickname for me. As I headed for the shower I saw Sir opening the suitcases. I immediately wondered how revealing my dinner attire was going to be. Then I realized I had been running around naked all day in front of all these same people, so what difference did it make.

Out of the shower I brushed out my hair and did my make up the way Sir likes it, dark eyes and lipstick that Sir calls "please fuck my mouth red." With some trepidation I stepped out to see what Sir had chosen for me to wear to dinner. On first glance, it looked nice. It was silver with a halter top, and a high empire waist. I slipped it on and found out why Sir liked it.

The entire dress was made of sheer fabric. The halter top was just two narrow strips of the sheer material that covered my nipples, but only about half my tits. The sheer fabric left my nipples quite visible. The skirt was floor length but quite narrow with side slits all the way up to the my ribs at the empire waist. If I stood still most of my ass was covered, but walking flashed my hips and half my ass. Sir had selected a pair of six inch stilettos to go with the gown and a beautiful crystal choker with matching cuffs and dangling earrings. I called them crystals, but with Sir they may well have been real diamonds. Sir finished it off with a bright stainless plug in my ass.

Looking in the mirror I did look stunning, and Sir looked quite proud of himself with his dress selection or his ownership of me. Sir looked comfortable in his khaki pants, Hawaiian shirt and Huarache sandals.

Dinner was buffet style, a wonderful selection of familiar and native dishes. At first, I was trying to think of how to modestly go through the buffet line, but decided to just pretend I was naked and what got seen, got seen. It helped that most of the women wearing revealing clothing. Sir picked a table occupied by two young men who looked to be twenty something. They seemed delighted to have me join them.

We had a nice chat with them during dinner and the entertainment that followed. When the dancing started, Sir invited each of them to enjoy a dance with me. They both started out very nice, I had to start grinding myself against them, feeling their cocks get hard before their hands started wandering, slipping inside the slits on my dress exploring my ass. The second one suddenly jerked his hand back when he came across my plug. I smiled and told him it was ok, and he spent the rest of the dance exploring it, pushing it in and gently pulling it out against my ring.

When I returned to the table with the second one, Sir said, "We have been talking about the hot tub. It apparently is where the nighttime action starts. Sir asked them both if they would like to join us. Both immediately jumped up and accepted Sir's offer. They led us to the area of the hot tub and explained that whatever happened in the hot tub was ok with the resort, but no public sex in the resort including the deck of the hot tub.

Both men left their clothes on a railing near the tub as did Sir. I left my heels and my dress there and Sir took my hand and helped me down into the tub. It was only about half full of people. Sir had as seat and motioned for the two men to take a seat on either side of him.

Sir turned me facing away from him and lowered me into his lap, or more accurately onto his cock. Sir reached around and grasped my tits in his hands and started pumping me up and down on his cock.

I heard Sir tell the two men, "the rules are simple, don't hog the hole, take a half dozen or so strokes and pass her back. Feel free to explore all of her charms. Don't hurt her. Agreed?"

That got a hearty "Yes Sir, from both men.

Master pulled me up off his cock and handed me to the man on his right, who lowered me onto the hard on I created on the dance floor. He was wide but not exceptionally long. He used my tits to move me up and down on his cock, but after the half dozen strokes Sir had allowed, passed me back to Sir.

Sir also took only his half dozen strokes before passing me to the man on his left. This guy was big. He lowered me slowly allowing my cunt to adjust to his size, then slowly took his half dozen strokes. I still wasn't comfortable with his cock when he passed me back to Sir.

As Sir slipped into my cunt I grabbed him with my Kegels, which got a nice moan, but probably wasn't necessary as my cunt quickly adjusted to his size. As I sank onto the man on Sir's right, he reached down and started rubbing my clit and pinching my nipple as I actively pumped up and down without him doing it. He got in a few more strokes than his allotted half dozen before passing me back to Sir. As I was riding Sir, I took a look around the hot tub. Most people were watching us, but one very young girl was giving a blow job to an older gentleman. It looked like he was coaching her on technique.

Passed back to the large cock on the left, he slid in easily this time and fucked me harder. He also took quite a few more strokes than the allotted half dozen, but no one seemed to mind, I certainly didn't. I'm not a size queen, but size does matter.

When Sir got me back he asked how I was doing. I managed a moan and a weak, "Fine Sir." Sir twisted my nipples hard as he fucked me, before handing me off.

The man on the right took quite a few strokes, but I felt him swell and the pulses in my cunt told me we had a winner. I turned, kissed him and thanked him. before he handed me back to Sir.

Sir smiled and immediately handed me to the man on the left and said, "Now you can finish too."

I was now fully adjusted to his cock, as he started pumping me up and down I started rocking my hips, pushing his cock even harder against my G-spot as he pushed by it on every stroke. I came hard, my moan had the entire hot tub looking at me, as wave after wave ran up and down my cunt as I clenched hard on his cock. That seemed to set him off as I felt him swell even larger and I actually felt his cock jerk as he shot into my cunt. I collapsed back into him and he wrapped his arms around me taking a tight grip on both of my breasts and giving them a hard squeeze. I looked over and saw the smile on Sir's face. I was finally released and passed back to Sir. Sir had me stand and give both gentlemen a kiss and a thank you as they headed for a rendezvous they had set up earlier at the beach.

As Sir held me on his lap the young girl being instructed on the art of the blow job by the older gentleman finally got her reward as he came in her mouth, causing her to gag and spit about half of it back out on the gentleman. He didn't seem to care and just sat back down to wash it off. But the girl was just beaming, so proud of her accomplishment.

Sir helped me out of the hot tub and into my heels. He carried my dress as we walked nude through the resort back to our rooms. Sir took a shower while I removed my makeup and then took my shower as Sir collapsed on the bed. As I came out of the shower, I saw Sir laying on his stomach on the bed. I crept between his legs and started rimming and tongue fucking his ass, trying to take my tongue deeper and deeper into his ass as I worked it.

I heard Sir moan and then roll over revealing his cock at full glory. I suddenly realized that Sir was the only one fucking me in the hot tub who had not cum. I started worshipping Sir's cock, kissing, licking and sucking before I started fucking it with my mouth and throat. I saw Sir watching me and started keeping unbroken eye contact with him as I saw him smile. Sir motioned for me to come up and I threw my leg over his hips and dropped my wet cunt down Sir's cock as fast and hard as I could. I almost came from my cunt hitting his pubic bone.

For those that didn't know, rock and roll is an old sexual term for what a woman does with her hips while being fucked. Rock is back and forth while roll is more of a circular grinding motion. Lets just say I did a rock and roll on Sir's cock in addition to pumping up and down. Sir reached up and grabbed both nipples, pinched them hard, and held them firmly in one place as the rest of my body was moving. It was excruciating, it felt incredible, my body couldn't decide which.