Sirs R&R 2 Jamaica

Feeling Sir's cock swell and shoot repeatedly into my cunt sent me over the edge, my cunt clenched, my back arched sending new pain into my abused nipples. Sir called it a scream; I called it a loud moan. I collapsed onto Sir, he grabs a handful of my hair and kisses me long and hard, his cock still lodged in my still rippling cunt.

I eventually rolled off Sir, leaned down to lick and suck his cock clean. I like to sleep gently sucking on Sir's cock, so I laid my head on his abs and gently sucked his cock as I heard Sir start to snore.

Sir was coming out of the shower when I woke up. We applied a liberal coating of sunscreen to each other, and Sir added a generous helping of lube up my ass. I gave him a quizzical look and he just smiled. He said he was going to go try wind surfing, and suggested I try the nude pool after breakfast. He also told me that for breakfast, only the genitals had to be covered and handed me the skirt I had worn the night before.

Even at breakfast the variety is amazing. From model wanabe's to the local PTA meeting, from studs to Dad bods. My outfit got some looks but no real comments. Sir had on his swim suit and another of his vast Hawaiian shirt collection.

After breakfast Sir walked with me down to the nude pool on his way to the beach and windsurfing. I wasn't too surprised when I got to the nude pool to see our pilots. Sir greeted them, then turned to me and said, "They look bored, keep them entertained until I get back for lunch. Sir gave me a quick kiss, a hard slap on my ass, and headed down toward the beach for a morning windsurfing.

The pilots helped me down into the pool and immediately sandwiched me. One behind me grasping my tits to pull me tight to him, his cock nestled in the groove of my ass. The other taking control of my mouth with his tongue with his hand sliding down caressing my cunt. I heard the pilot behind me say, "Too hot out here, lets head for the shade of the grotto."

I hadn't noticed it being that hot so early in the morning but realized that it wasn't my choice if I was to keep them "entertained." I also realized why Sir had so thoroughly lubed my ass that morning.

They walked me, still sandwiched, into the grotto. Bill, the pilot, sat down and pulled me backwards, and slowly lowered my ass down onto his cock, until I was sitting on his lap, with his cock deep in my ass and his fingers still abusing my nipples. Howard, the copilot, lifted my knees onto his elbows, and eased his cock fully into my cunt.

With me sitting on his lap, and Howard pushing me into him, Bill had limited ability to move, but as Howard started fucking my cunt, he rocked me, causing my ass to move with each thrust, giving Bill some movement on his cock. But the main thing, as Howard fucked me, Bill could feel Howards movement in my cunt through the thin membrane separating the two passageways.

While I was being double teamed, two more couples came into the grotto. They were both making out, but primarily watching us. One of the ladies came over and Bill released my nipples allowing her to start licking and sucking my nipple with an occasional nip. The other lady looked at her partner then came over and took my other nipple, doing a lot more nipping than licking and sucking. I started to moan, and Howard leaned forward, silenced me with a kiss and his tongue and started pounding me harder and faster.

Ripples started running up and down my cunt and I came hard, squeezing Howard's cock hard. Howard released my mouth and let my moans and scream echo throughout the grotto, and beyond. As I started to come down, I felt Howard swell and shoot deep in my cunt, that set my orgasm off again as my moans and scream once again echoed in the grotto. The two ladies returned to their boyfriends, and I saw one of them immediately being face fucked.

Howard pulled out of my cunt and released my legs and climbed onto a seat in the grotto at water level. Bill stood us up, still buried deep in my ass and turned me so I was facing Howard. I leaned forward and started cleaning Howard's cock, as Bill used his newfound freedom of movement to start going fast and deep in my ass.

Bill slammed hard and deep into my ass, and I felt his cock swell and start pumping. As soon as I felt him leave my ass, I turned squatted and cleaned his cock. The three of us huddled together on a low seat in the grotto to the applause of about twenty people who had gathered to watch us. I didn't need a sunburn for my face to be beet red.

We sat in the grotto for awhile, one on each side of me. I was stroking their cocks back to life and their hands manhandling me kept me on the edge, as we watched other couples kiss, suck, lick and fuck. Whenever I got one of the pilots hard enough, I would get picked up and lowered onto their cock. I would work my Kegels massaging their cock, while still fondling the other one, until he got hard and I would be lifted off one cock and set down on the other one. I got one major surprise when I was passed back to Bill, and he slipped into my ass instead of my cunt.

All the time my nipples and clit were being played with and abused. They were all tender by the time Sir came back from windsurfing to take me down to the oceanside grille for lunch. As we were leaving the grotto, I saw both pilots talking with other ladies.

Sir and I had jerked chicken for lunch along with a couple of Red Stripes. We decided to lay on the nude beach for awhile before going for a nap during the heat of the day. We had barely stretched out on two of the lounges when three young twenty somethings stopped to talk to Sir. They were friends of the two men I had enjoyed in the hot tub the previous night and apparently, they had spoken highly of the experience with their friends.

One of them asked Sir if he minded if he took me out for a swim to cool off. Sir took looked at me and said "have fun," that was not a suggestion. Sir's only request was "Don't drown her."

The ocean was refreshing, much cooler than the pool. We waded out about waist deep before we started making out. He was fingering my cunt and I was stroking his good sized cock, feeling it continue to grow. I wrapped my arms around his neck and my legs around his hips as he guided his cock into my cunt. As much as it had been used that morning, between his size and the cool water I felt my cunt stretching to accommodate his size.

He carried us out into deeper water as I slow fucked him, the waves started picking us up and moving us adding a new movement to mine, we were essentially weightless, buoyed by the water as each wave passed us. Occasionally he would duck us under the wave, leaving me without air for a moment if I didn't see it coming.

Eventually he started carrying me back into shallower water. Once we reached shallow water, he laid on his back and I was now riding him. I was facing the shore, watching Sir and the guy's friends talking and drinking on the beach while watching me fucking along with it seemed half the people on the beach. His hands were on my hips, helping to keep me on him as the waves crashed into and over us. My hands went to my tits, caressing, groping, teasing and abusing my nipples as I kept my eyes on Sir's on the beach. He was still joking with the young men on the beach, but his eyes never left me. I worked to put on a show for Sir and the rest of my audience, besides showing off my tits I was rolling my hips as I fucked him and made a show of pulling in my stomach as I rocked back and forth too.

I had already had three or four small orgasms when I felt his cock start to swell. I gripped his cock as hard as I could with my Kegels. When he came, his hips slammed me upwards, completely clear of the water twice, before finished. While he bruised me, I managed to stay on and ride him out. He used my nipples to pull me down into a kiss as the wave crashed over us, rolling us in the sand.

We came up giggling and headed back to shore holding hands. Sir met me with a kiss, smile, hug and a dry towel. I heard applause up and down the beach, so I curtseyed to even more applause. The trio headed off for the pool for a scheduled meeting with friends. Sir said that two of them were from near our town and would be riding back on the plane with us. Sir said they were excited for not only being on a private plane, but he had told them I was the full service stewardess. It sounded like it was going to be a busy flight.

Sir and I went back to our room to get out of the heat and rest up. Sir laid down on the bed while I took a shower, douched, and brushed my hair out. By the time I got back to bed, Sir was snoring. I laid down next to him, took his cock into my mouth, rested my head on his abdomen and fell asleep gently sucking Sir's cock.

Sir started to stir and woke me up, his hardening cock still in my mouth. I started licking and sucking. I rolled between Sir's legs so I could watch his face as I sucked his cock. Sir fluffed his pillow, smiled, and laid back to watch me. I put on my best show, sucking Sir's cock. I flicked my tongue across the piss slit. I circled the head with my tongue before sucking it into my lips. I let his cock lay on my face as I licked and took his balls into my mouth to caress with my tongue. I took him into my throat, I let him feel my throat gagging. I ran my tongue up and down the sensitive bottom of Sir's cock. I sucked him hard, I sucked him gently.

Sir finally gave in and came. I let his first few shots go straight down my throat before pulling him back and filling my mouth with the rest so that I could both taste Sir and show him the gift he gave me. I opened my mouth to show Sir the gift and held it until I heard permission to swallow. Sir pulled me up to a hug and a kiss then told me to go back to the shower and prepare my ass for the evening.

I took and released both a Castile soap and then a saltwater enema to ensure my ass was clean. I worked a copious amount of silicone based lube deep in my ass as it sounded like Sir had plans for it.

When I came out of the shower Sir was sitting on the bed, still naked, with a paddle in his hand. He motioned me across his lap, and I laid with my butt on his thigh, my hands and toes touching the floor on either side. Sir proceed to blister my ass until I swear it was glowing. I was bawling but was disciplined enough to keep my hands on the floor and away from my ass.

When Sir finally stopped, he said, "There, that will go well with your dress for this evening."

Sir moved me to kneeling at his feet. He took a shiny stainless nipple shield and clamped it on my right tit and then my left. They weren't tight clamps, but enough to pinch and keep the shield in place framing my nipples. They had a little arm that held a ruby crystal that pushed into the center of each nipple, and when Sir flipped a tiny switch, they started to glow. Sir then worked a large plug into my lubed ass. It had a similar ruby crystal and light in the center.

Sir told me to go dry my eyes and do my make up for the evening while he got dressed. I made my eyes dark and smoky and my lips bright red as Sir likes. Sir put on a pair of khaki's and one of his better Hawaiian shirts.

Sir took my dress out of the closet. There wasn't much to it. It was silver mesh, essentially transparent. The top was a thin band of fabric that went across my back, wrapped around in front over my tits, up over the opposite shoulder and was tied behind my neck. It had lots of little ruby crystals like the ones on my nipples and ass.

The skirt was a simple wrapped skirt, except that it didn't quite meet when wrapped at my hips and two thongs tied and held it in place. It was ankle length and cut away so that my entire left leg was exposed. Since the dinner was a beach event there were no shoes.

I twirled for Sir's inspection. He frowned and said, "I was hoping your glowing paddled butt would show better, but I did the best I could." Sir pushed a button on a little remote and the ruby LED's glowed brighter, I couldn't see the one in my ass, but was sure it did likewise. Sir pressed another button, and they started blinking. Sir decided he didn't like that so went back to the just the bright setting.

Sir kissed me and put his arm around my waist as we walked down to the beach. We got a drink and sat and watched the glorious sunset. Dinner was again set up buffet style, seating was a several long tables. Sir chose seats at a table near the three young men from earlier and the young ladies they were now with. Sir joked with the one who took me into the ocean, asking if he had anything left after leaving the beach. The young lady he was with blushed bright red. Sir reminded the two flying home with us, to be at the checkout on time and no drugs on the plane. Both looked and me with big smiles. Everyone at the table laughed when Sir changed the LED's on my tits to flashing.

One lady came up and asked Sir if she could have a dance. Sir said yes and to my surprise she took my hand and led me onto the dance floor. She was a good dancer and I tried to follow her but was hopeless. She didn't seem to mind and was happy to hold me close and let her hands roam under my skirt.

Dinner was delicious. The young Jamaican waiter seemed to take special delight in keeping my rum drink full all night. The resort was providing entertainment that evening, we watched about half of it before Sir took my hand, put his arm around my waist to steady me, and led me back to our room. Since our room overlooked the beach the sound of the drums from the entertainment echoed throughout our room, especially after Sir opened the windows for the cool evening breeze.

Sir removed my dress and the nipple shields. He blindfolded me and put the cuffs on my wrists and ankles before leading me to the bed. He placed me on my knees with them wide apart on the bed and attached my wrist cuffs to the corresponding ankle cuff. The plug was pulled from my ass. I heard a shuffling of feet and the door open and then closed followed by more shuffling of feet.

I laid there silently, listening, but not hearing. Had Sir left me bound while he left the room? Had someone else joined our party? Then I smelled a new but familiar perfume, the bed shifted, Sir lifted my head using my hair, and when he lowered it back down, my face was in a rather wet cunt. I almost immediately felt a tongue run across my clit and probing up through my cunt. I started to reciprocate with the cunt in my face, but my ass suddenly exploded in pain as Sir, or someone struck it with the paddle.

After the first heavy strike, whoever was wielding the paddle kept it much lighter, but in constant rhythm with the drums on the beach. After Sir's predinner warm up it didn't take much before my entire ass was on fire again. Then the spanking stopped. All that was left was the tongue exploring my cunt, and the taste on my tongue as I explored hers.

The bed shifted again, and a cock went deep into my cunt in one long slow push. It immediately started to slowly but deeply fuck my cunt. Whoever it was had an ear for music. He went in deep on the downbeat and back on the offbeat. The tongue now concentrated on my clit, licking, sucking and occasionally gently biting. I started doing the same with her cunt.

The drums on the beach went to a higher tempo and so did the cock fucking my cunt. Between the tongue and the faster tempo, I was being pushed towards the edge. I was about to cum when, suddenly the cock was gone from my cunt. It only took a few drum beats before I felt it pushing at the ring of my ass.

I felt a slight sting as the cock pushed through my ring, but it then went quickly deep in my ass and I felt his balls hit my cunt. The drums had returned to their slower reggae beat and again the cock went deep in my ass on the downbeat and back against my ring on the upbeat. The tongue in my now empty cunt had renewed its efforts.

My senses were being overwhelmed: the taste on my tongue; the licking, sucking and nipping of my clit; the cock fucking my ass; the pain as his hips beat against my burning butt with every stroke in my ass; the reggae beat and song in my ears. I wanted to cum, I needed to cum, but my senses were so confused that I couldn't go over the edge, I just went harder and harder against that edge, climbing ever higher.

Then all at once, my face was flooded as the lady under me came hard from my ministrations, and at almost the same time the cock in my ass swelled and started pumping deep in my ass. I screamed into the cunt in my face as my whole body went rigid, my back arched, and wave after wave ran up and down my cunt trying to grasp the cock that wasn't there.

I felt the cock withdraw from my ass followed by a hard slap on my bruised butt. I was pulled up onto my knees by my hair. I sensed then smelled the cock in front of my face, fresh from my ass and I opened my mouth to take it, to own it, to lick and suck it clean of the cum and my ass covering it. The cock pumped in and out of my mouth as I sucked, frantically licking it, trying to find every crevice, every drop of cum that covered it, every nuance of taste.

I sensed that the tongue that had been using my cunt was now rimming my ass, digging for what the cock had left there, lapping up what was pouring out of my gapping ass. I was controlled again by my hair and turned and laid down on the woman under me, now face to face. She took my head in both of her hands and guided me into a kiss. As we kissed, she pushed what she had gathered from my ass into my mouth. The same nectar that I had sucked from the cock. As we continued the kiss our tangled tongues pushed the nectar back and forth sharing what she had found. We also licked each other's faces clean of the squirt we had both given the other.

As I lay there making out and sharing with the lady, I started to wonder whose nectar we were sharing. Was it one of the three young men; or was it the lady's partner I had seen her with at dinner? We finally broke the kiss and as I raised my head the blindfold was removed from my eyes. I was looking into Sir's smiling face. I looked around for the other person and Sir started laughing. I suddenly realized that it had been Sir and no one else. Sir had saved me for himself on our last night in Jamaica.

Sir cuddled with both of us for a bit until the lady said that her partner was waiting, dressed and left. Sir and I continued to cuddle until we both fell asleep. At some point during the night, Sir rolled over on top of me and fucked me. It was so quick and unexpected that Sir came but I didn't. After Sir rolled off me, I bent down to clean his cock and spent the rest of the night resting my head on his abs, gently sucking on his cock.

By the time I woke up in the morning, Sir was already showered and packed. He had left out a simple short wrap dress and heels for me to wear. I did my morning enema, showered and shaved. As I slipped on the dress and heels I realized that it was the most I had been covered since we had gotten to the resort.

We had a quick light breakfast while the porters brought our luggage up to the reception area. By the time we got there the luggage, and our two passengers were there and waiting. Sir checked to make sure that our passengers had their passports, and both swore that they had no contraband. The pilots were already at the airport doing their preflight checks and clearing our paperwork. It took five minutes to go through the Jamaican exit procedure and we loaded the plane ready to head home. As I boarded the plane, I noticed the back row of seats were already fully reclined with several layers of sheets on top, the copilot gave me a big grin we saw that I had noticed. Sir and our two guests were huddled at the foot of the steps, apparently Sir was laying down the ground rules for the trip.

I chatted with the pilots while we waited for Sir and the passengers to board. They had both had a wonderful time in Jamaica but had only the slightest hint of a tan, apparently not too much beach time.