Sirs R&R

When Sir saw us, he called everyone to the table. Sir was at the head of the table and Susan and my seats were on either side of him, with me on Sir's right side. As I started to sit, I saw the well lubed seven inch dildo in the middle of my chair. From Susan's reaction she had the same. As I settled onto it I looked at Sir and saw him smile, reach into his pocket and turn the dildo vibration on a low speed that ramped up and then quit before continuously repeating that pattern.

Everyone at the table was either naked or had put on a simple coverup. I was seated next to the naked gentleman of my favorite couple, with his nude partner on his other side. I wasn't seated long before his hand found my upper thigh, gave it a squeeze and didn't let go. His hand never left my thigh through the entire meal.

After the desert course, Sir announced that the dungeon was now open for those who chose to use it. He reminded everyone that the last guest should plan to leave no later than 2:00 AM, and he thanked them all for coming.

As the guests started to rise and make their plans the gentleman holding my thigh said, "You are ours this evening." I looked to Sir, and he nodded. He took my hand and with his partner right behind headed up the stairs instead of down to the dungeon. I was even more surprised when he led me into my room. As soon as we entered my room, I noticed that someone had moved a horse and our guest's toy bag into my room. He immediately pulled me tight into a deep kiss as his tongue explored my mouth, she reached inside my kajira and grabbed both my tits tight, squeezing my nipples hard. She whispered in my ear, "You are ours to enjoy for the evening, your Sir's only stipulation was that you show up with cane marks on your ass when he gets you back. I told him we would be delighted to provide them."

I was led over to the horse and blindfolded. I laid down and he strapped my forearms, thighs and calves to the saddles on the horse. My chin was just off one end of the horse and my ass hanging off the other end. He picked up my head with my hair and I opened my mouth to accept his cock.

He rested his cock on my tongue and said, "I am going to fuck this end while my partner delivers your first set of required cane marks. Be careful, for every tooth I feel, there will be five more stripes on your cute little ass.

He started slowly and gently fucking my mouth, a little deeper with each stroke. I gagged when he reached my throat the first and second times, but the third time he entered my throat without an issue. As was just relaxing into enjoying his use of my mouth and throat when with his cock deep in my throat, my ass exploded in pain. I heard her behind me, "One."

I'm sure he enjoyed the vibrations in my throat as his cock muffled my scream. They had a pattern every third or fourth time he was in my throat, she administered another stripe on my ass and his cock muffled my scream. After every stripe she counted for me, a total of five stripes on my ass. After being surprised with the first stripe, I was very conscious of his cock and my teeth on the rest.

After the fifth stripe, he pulled out of my mouth and was replaced with his partner kissing me and caressing my tits dangling on either side of the horse. I felt the cool lubed fingers start exploring my ass, lubing, caressing and stretching. While my butt was still on fire from the new stripes, her kisses and caresses, and his gentle probing of my ass was definitely turning me on.

I felt his cock pushing against my anal ring and a brief sting as it popped through into my ass. A sudden sensation told me she was putting clamps on my nipples as she kept her tongue playing in my mouth, and sucking mine into hers. The clamps didn't so much hurt but were simply one more sensation for my overwhelmed senses.

He started fucking my ass, slow steady and deep. The change in sensations in my nipples told me she was pulling on the chain connecting the nipple clamps and adding weights. The cock in my ass picked up the pace going faster and harder. The impacts of his hips driving into my newly stripped butt added a new element of pain into the eclectic suite of sensations.

I started concentrating on the kiss, the only sensation I had any control over. I gently bit her tongue, so I could flick mine back and forth across the tip of hers. I released it and sucked it deeper into mine, only to have her repeat both with my tongue, but biting it harder. As much as I tried to concentrate on the kiss and her tongue, my ass kept reminding me it was being fucked, and my butt frequently noted a harder slap from his hips against the stripes. Whatever she was doing with the clamps on my nipples occasionally registered as a change in sensation.

I suddenly felt him slam hard into my bruised butt, driving deep and fast into my ass. I sensed his cock swelling and felt pulse after pulse as he came deep in my ass. As he was releasing in my ass, she pulled and released both nipple clamps at the same time. I moaned in her mouth as I came hard, ripples running up and down my cunt. There was a multicolored light show inside my blindfold. In my haze I felt him slowly fucking my ass with little, small movements. She gently kissed my lips as she fondled my tits and rubbed my sore nipples. He withdrew from my ass, she kissed me one more time and was also gone.

I was floating in subspace when I sensed and smelled his cock by my face, I opened my mouth and received his cock for me to lick and suck clean. It was a mix of his cum and the lube, hate the taste of strawberry lube. As I was sucking his cock clean, I felt her tongue rimming my ass. Gently probing, licking, cleaning the leftovers of his fuck, fucking my ass again, this time with her tongue.

I must have faded out, the next thing I remember is lying on my bed sandwiched between the two of them. Him spooned behind me, his cock nestled in the cleft of my ass, one of his hands holding and caressing one of my tits, while she was licking, sucking and nibbling on the other nipple, her hand in my cunt rubbing against my clit.

When she saw my eyes flutter open she moved up and kissed me, smiled and said, "Welcome back to the living. Ready for your second set?"

I wasn't sure what she meant by the second set, but I was theirs regardless of what they intended. She scooted up until she was sitting, leaning back against the headboard. She trapped each one of my arms under one of her thighs and pulled me forward until I was laying on my front, my face buried in her cunt.

I started kissing, sucking and licking her cunt, savoring the sweet flavor. In the back of my mind, I was wondering if he was going to lift my hips to fuck my cunt, or was just going to fuck my ass again. I was wrong on both guesses.

She pulled my face in tight to her cunt and my ass exploded in pain again. I heard him count, "six," as I screamed into her cunt. He was in no hurry to complete the strokes. I concentrated on pleasing her, moving up to suck, tongue and gently nibble on her clit, lapping up the sweet juices from her cunt. Sometimes I would know the blow as coming when she would pull my face tight into her cunt to muffle my scream, sometimes it took me by surprise.

After I heard him count "ten," I felt his tongue rimming my ass before he worked a large lubed plug into my ass. It stung until the wide part passed my ring. Once it was fully seated in my ass, it started gently vibrating.

I continued concentrating on pleasing the cunt in my face. He stood on the bed moved up and started fucking her face. Between my work and her partner's cock she was moaning almost constantly. It wasn't long before came flooding my face as she squirted all over it.

He must have cum soon afterwards. She leaned down and with his help rolled me over onto my back before she leaned down, kissed me and pushed his entire load of cum into my mouth. We kissed sharing his cum back and forth. He knelt over my chest and his partner, and I shared the duty of licking and sucking his cock clean.

The three of us collapsed on the bed, snuggling and caressing, perhaps occasionally napping. Somewhere around 1:30 the alarm on one of their watches went off. He rolled me onto my back hooked under my knees and bent them up to my tits and fucked me. Just a quick slam bang, thank you mam before depositing whatever he had left into my cunt. They both kissed me goodbye and left.

I was lying there debating if I had enough energy left to go cleanup in the bathroom when the door opened, and someone carried Susan into my room and laid her on top of me with her cunt in my face and left.

I started licking up the cum seeping out of her cunt. The more I licked, the more I got. I felt Susan's tongue starting to do the same cleaning job on my cunt. While I suspected that having already cum twice there wasn't too much cum in my cunt, Susan's was full of cum. Once I tongued it open it poured into my mouth. I licked and swallowed until I was getting nothing but Susan's juice.

I rolled out from under Susan and moved up to hold her face to face. She smiled and started licking my face clean, and I returned the favor. We kissed and fell asleep in each other's arms.

When the morning sun streaming through the windows woke us up, I learned from Susan that two couples had split. The two ladies taking Roy to Susan's room and the two male partners sharing Susan in one of the other rooms. Like me, right before Sir's two AM curfew both had fucked her, then one carried her to join me. It occurred to both of us that had been Sir's doing and instructions to the couples he shared us with.

We shared my bathroom, giving each other our morning enemas, and showering together. We skipped makeup, put our heels on and otherwise went naked down to the dining room. We found Sir enjoying breakfast, with one of our female guests under the table serving Sir. We both fixed plates in the kitchen from a small buffet of scrambled eggs, sausage, bacon, waffles and large cups of coffee.

We politely asked Sir about the lady serving under the table. Sir said he wasn't sure which one she was. When he came down that morning, she was cooking breakfast in the kitchen. Sir wasn't sure if she was a leftover or her partner was still sleeping somewhere, but otherwise he didn't seem to care.

Sir asked, "Did you take good care of each other last night? I assume my guests did as I asked."

Susan and I looked at each other and giggled before Susan answered, "Yes Sir. We both provided the necessary clean up and aftercare, after a wonderful evening."

Master nodded and said, "both of you stand up, turn around and bend over." After a minute we heard, "You may both sit down. I'm pleased to see that my instructions were carried out properly.

We had compared our stripes in the shower. While I had ten nice bright evenly spaced red stripes across my ass, Susan seemed to have more, but not nearly as well defined as my bright red stripes.

Roy wandered up from the basement dungeon and showed Sir his stripes before going to the kitchen to fix his breakfast. Roy's stripes were similar to Susan's, not as sharp and bright as mine, but quite a few more. Roy sat down at the table. I saw Sir reach under the table and a few seconds later saw Roy react. From the feet under the table, Sir had passed the under table server over to Roy.

Sir asked Roy if he knew who she was. Roy answered, Last night when the two ladies went to leave, one of them got left behind so she spent the night with me. I don't know if her partner left alone, or the two men took the other lady with them both." Sir just shook his head.

As sir finished his breakfast he said, "I'm going to shower and clean up." He turned to me and said, "We are going for a ride, get dressed, do your makeup, nice and slutty, then come to my room." "Roy and Susan, see if you can find a home for our lady friend. Until she leaves, she can help you two clean up."

I took my plate to the kitchen and headed back upstairs. A ride with Sir can be about anything. Driving is one way that Sir unwinds. We could ride on a twisty road for a few hours and wind up back at his house. We could wind up at a favorite restaurant somewhere two hours away. He could drive up to a remote mountaintop, bend me over the hood and fuck me, before driving back home. On rare occasions we wind up at one of his friend's house and they double team me. On rarer occasions he has something on his mind that he wants to talk about. I've learned not to ask questions, just sit back, enjoy the ride and experience whatever Sir has in mind.

I have a complete wardrobe in my room at Sir's house. Mostly chosen by Sir to suit his taste, which is primarily to show me off as much as legally possible. I put on a short wrap dress, a size too small to better show my tits and cause me to flash more than intended. Make up was not excessive, I started with sunscreen incase Sir took the convertible, otherwise mostly accenting my eyes and of course Sir's favorite "please fuck my mouth" shade of red non-smear lipstick. I have a gold chain necklace that is not removeable, it has a pendant with Sir's initials to mark me as his.

Once ready I go down the hall to Sir's room. He is sitting on the bed and motions for me to kneel in front of him. He wants to hear how my session with the couple went. I give him the highlights including the time with Susan. He smiles and tells me the couple gave him a glowing report on my performance as they left. They want to borrow me some weekend, but don't realize that Sir doesn't loan out what is his.

Sir checks and seems disappointed with the plug in my ass. He chooses a larger glass one from his collection, lubes it and works it into my ass. It has a ring that protrudes outside my ass, and I know from experience that riding on it is going to be an issue.

Master puts a studded leather collar around my neck and surprises me by attaching a leash. I'm normally allowed to walk in Sir's house, but when on a leash I crawl. I'm hoping I haven't somehow disappointed Sir.

I crawl following Sir downstairs. We learn that the partner is coming to retrieve the left over lady sometime after lunch. Her partner had left with the other couple and is still busy double teaming that lady with her partner.

Sir leads me out to one of his Porsches and helps me stand and crawl in before strapping my belts tight. I quickly recognize that we are heading towards one of Sir's favorite twisty mountain roads. I sat back, relaxed and was thankful I kept breakfast light. Sitting on the protruding plug is not very comfortable, but I squirm to Sir's delight until I find a reasonably comfortable solution.

Sir is a masterful driver so even as he races around the curves I relax and don't worry. I start to reminisce about how I got here as Sir's. My company was doing well, growing, profitable, with a good management team under me. Our product was well made of consistently high quality. Sir came into the picture one day when he realized we were the sole supplier to several of his companies. He asked several of his purchasing people why that supply wasn't diversified and was told by each one of them that ours not only had the best price, but the fewest quality issues, and delivery was always on time. Sir became concerned about the situation and approached me about acquiring my company. Sir is powerful, charming and not accustomed to being told no.

He was shocked when I turned down an offer that was probably three times what my company was worth. He threatened my stock, there wasn't any. He threatened to take his business elsewhere and I asked, "So you are going to tell your purchasing people to pay more for lower quality and uncertain delivery? The final resolution was eventually, I kept my company, and he got me, though it was far more complicated than that.

Like many male and female high end business executives I had trouble letting go. Always in control, never showing weakness by allowing my submissive side show. Sir allowed me to release and enjoy that predominantly submissive side of me without losing the tough dominant business leader. Sir reminds me from time to time that I am free to leave his service at any time. He knows I'm not; I could never find elsewhere what he gives me every weekend, holiday, and vacation day. Frankly, we are both amazed at how obedient I am to his wishes, when my company is not involved.

I wasn't paying attention to where Sir was taking us until he pulled into one of his favorite cliff top restaurants. Sir parks and comes around to help me lift my butt out of the ridiculously low seat. He adjusted my dress, revealing more cleavage and took my arm as we entered the restaurant. The manager greeted Sir by name, and they shook hands and did that guy hug thing while the manager checked out my tits.. Sir whispered something to him, and I had to smile as he went over and changed a padded chair for a solid wood chair, before leading us to that table. Of course, Sir smiled as he watched me fidget, trying to get comfortable sitting on the plug.

Sir asks if I enjoyed the party. I told him I did for the most part. Freezing my nipples distributing the ice was not a favorite. Being the pool toy is fun but exhausting, but I thanked Sir for only leaving me there for an hour.

Sir commented, "You got along very well with the couple who had you for the evening. They asked to take you home, but I said no. I think the next weekend I'm not available I will send you to them. "

I was shocked that Sir would lend me to another couple. He had always said no before. I was also surprised that he didn't ask me, though it was probably pretty obvious that I would have said yes, but I did wonder if I would have had a choice.

We had a delightful dinner and watched the sunset over the mountains. As we got back to the car, Sir untied my belt and slipped the dress off my shoulders, leaving me standing there in my heels, collar and plug. Sir helped me into the car and threw my dress into what passes for a backseat in the Porsche. Sir was not as exuberant driving home in the dark as he had been earlier. Part of it may have been his hand high on my thigh when not on the shift knob.

When we arrived back at Sir's house, he again helped me out of the low seat. He kissed me, bent me over the warm engine compartment of the Porsche and fucked me. Just a quick, no frills fuck claiming me as his, as if I could forget. I felt him swell and shoot deep in my cunt. He leaned over on top of me and whispered, "Mine."

As soon as he stood up, I dropped to my knees and cleaned his cock before looking up at him and replying, "Yours." He helped me to my feet, retrieved my dress from Saturday morning from my car and helped me slip it on, before opening my car door, kissing me and slapping my ass as I got in.

He was still visible in my rear view mirror as I drove down his long drive, when I started crying from missing him.

Sirs R&R Jamaica