Sirs R&R

Literotic asexstories – Sirs R&R by whiterabbit0117,whiterabbit0117
I pulled up to Sir’s house exactly five minutes before my designated arrival time that Saturday morning. I slipped off my short dress and walked in my five inch heels to attach my leash to a hook and kneel on the side porch, naked except for my heels, a chain collar with Sir’s initials, and a medium sized stainless butt plug.

I am a 32 year old divorced owner of my own successful company. I am 5; 4″ tall, weigh 125 pounds, and work out in my home gym four days a week. I am also Sirs: girlfriend, slut, slave, toy, and anything else Sir wants me to be.

I am kneeling at Sir’s door every Saturday at precisely 9:00 AM. About the only time I know what to expect that weekend is if children are going to be present which requires me to be dressed more modestly. Otherwise, it may be a quiet day with Master, a weekend road trip, serving as maid and pool toy for pool party of a dozen people, serving as fluffer while Sir entertains one of several girls on his booty call list, a jet trip to Jamaica or Paris, or whatever else Sir has planned. I love it all except the weekends when I am the designated babysitter for one of Sir’s more vanilla events. As Sir says that stretches my masochistic tendencies.

Sir is old money. Besides the corporations he owns, he sits on several corporate boards, as well as on the boards of several philanthropic organizations. He runs non-stop all week, jet setting around the world, but manages to be home almost every weekend for R&R. That is what he calls me, when he isn’t calling me his slut. Sir is also a dominant sadist to my submissive masochist. Sir is 6′ 4″ tall, 220#, quite fit, with black hair with silver highlights. He doesn’t discuss his age but is somewhere around 40. Sir has never been married.

At precisely 9:00, Susan opened the door, took my leash and led me crawling inside. Susan is Sir’s secretary, housekeeper, and live-in slave. Susan informs me that today is a pool and play party for a local BDSM group and that Sir is waiting for me upstairs in the master bedroom. She unsnaps my leash allowing me to walk upstairs. At Sir’s I crawl when on the leash or when Sir tells me to, but otherwise I am free to walk, usually in five or six inch heels.

Sir is walking naked from the shower as I enter his bedroom. I am greeted by Sir in all his naked glory. Master pulls me into a hug and a kiss, his tongue exploring my mouth. As soon as he releases me, I kneel unbidden and kiss Sir’s cock, looking up into his eyes. I see Sir smile and I attack his cock, kissing, licking and sucking. Master takes a double handful of my hair and starts fucking my face. He stays shallow at first, letting me adjust and get him truly wet before he starts enjoying the tightness of my throat. We are soon in a rhythm that I know well. Sir will be in my throat until he knows I desperately need a breath, and will retreat into my mouth for me to explore his cock with my tongue. He occasionally changes his rhythm, only fucking the entry to my throat, I have to breath in that rhythm, in on one stroke, exhale on the next. I trust Sir is not going to break me, so I don’t panic as my lungs start to burn.

It is always Sir’s choice where he will cum. When he fucks my face, Sir may shoot down my throat, fill my mouth, or he may paint my face or tits. The only given is regardless of where Sir fucks me, I will lick and suck his cock clean when he is finished. That day Sir withdrew out of my throat and filled my mouth with his cum. I opened my mouth to show Sir his gift and when he nodded swallowed it all before licking and sucking Sir’s cock clean.

That earned me my first “Good girl” of the day. Master continued, “I assume Susan told you that we are hosting a pool and play party today. You will help Susan get the house ready, greet my guests at the door, meet any and all of their needs. Once my guests are here, you will be serving snacks, liquid refreshments, and entertaining our guests. The dungeon is closed until after dinner. Any questions?”

I replied, “No Sir.” Sir’s instructions included a couple of code words. Meeting “any and all of our guest needs” meant that guests were free to use me sexually, while “entertaining our guests” meant I would be totally obedient to whatever our guests asked of me. The dungeon being closed meant that while I could be hand spanked, groped, pinched and otherwise physically abused, that crops, floggers and paddles would not be used until after dinner. Of course, my hope was that when the dungeon opened it would be Sir using me.

Sir helped me to my feet, took me across his lap and spanked me. He started out lightly rubbing, stroking and lightly swatting my butt, but the spanking became heavier and heavier until I was crying, sobbing, and almost incoherent. Sir finally stopped, pulled me up to him, hugged and kissed me and said, “That should hold my slut until after dinner. Now go help Susan.”

I got up and started downstairs, still crying, my ass on fire, but hoping Sir’s words meant he planned to be the one using me in the dungeon. As soon as I found Susan in the kitchen she said, “Your makeup is a mess. Go wash up and then come back we have work to do.”

After cleaning the destroyed makeup from my face, I returned to Susan. She sent me to the dungeon to clean the equipment and make sure everything was where it should be. As I entered the room I had to stop and catch my breath. Every piece of equipment in the room had memories of me being attached or laid across them while Sir or someone else used clamps, crops, floggers, whips, vibrator, dildoes, and paddles inflicting pain and exquisite pleasure to the point that I couldn’t tell one from another.

I mixed up new antibiotic solution and cleaned all the instruments that had been left out around the room. All the surfaces on each piece of furniture got the same treatment. I found a big wet spot on one of the horses, obviously where Sir enjoyed Susan earlier. I should have been jealous, but I share Sir with Susan and his other submissives and have no claim to him. I finished by vacuuming the room before heading back downstairs.

Ice had been delivered. I distributed the 40# bags to the various coolers out around the pool, and deck. Not easy to do in five inch heels, but in my time with Sir I have gotten much more agile in high heels. Four inch heels are now the standard for my work dress, and five, six or ballerina for my weekends. Carrying the ice bags in my arms meant they were laying against my tits and my nipples were soon so hard they hurt. Their piercings took the cold straight into their core.

Back in the kitchen I help Susan transfer the snacks from the supplier’s boxes onto serving trays and place them in one of Sir’s massive cold boxes. I came out of the cold box with rock hard nipples again, to come face to face with one of the caterers, bringing items to fix later for dinner. It was over a minute before he made eye contact. I took his package, and he followed me as I carried it into the cold box. Without thinking I bent over to place it on an available lower shelf, flashing him with everything I own. I realized what I had done when I turned and found him standing there with his mouth wide open and a noticeable bulge in his trousers.

As we came out of the cold box, we met Sir who had come down to check on how the prep work was going. He noticed the caterer’s bulge and turned to me and asked, “Did you do that?”

I saw no purpose in trying to explain, “Yes Sir, I bent over in front of him storing his stock.” I saw the look in Sir’s eyes and went to my knees in front of the caterer.

Master smiled at the caterer, “I’m sorry for the distress my girl has caused you, please let her address your issue.”

I didn’t wait for a response. I unzipped the man’s pants and fished his cock out. It was nice sized, circumcised, and grew rapidly when I started licking and kissing it. My goal was to get him off as quickly as I could. I started sucking, licking and bobbing my head rapidly on his cock while maintaining eye contact. From the corner of my eye I could see Sir standing there watching, smiling. It did not take long for the caterer to groan and cum, filling my mouth to overflowing. He apparently hadn’t cum in awhile and I had trouble swallowing fast enough so some dribbled out of my mouth and fell onto my tits and the floor.

I cleaned the man’s cock, gently put it back in his pants, apologized, and thanked him. I took my fingers and wiped the cum off my tits and sucked my fingers clean, before leaning over and licking up what I had spilled onto the floor. As I knelt, I saw that Sir looked pleased. Sir and the caterer discussed dinner details for a bit, while I knelt in front of the man’s crotch. Sir finally helped me to my feet and told me to get back to work. As soon as I turned to do that, I saw the big smirk on Susan’s face. She enjoyed my work.

At 11:30 Susan said we needed to get ready for the pool party. I followed her up to her room. We showered together helping the other with the two enemas, checking for and dealing with stubble, and washing each other’s body. It is a strange relationship, we share Sir, though neither of us claims him, there are no signs of jealousy, and we are more like incestuous sisters than anything else. When we shower together there is lots of groping and kissing and some body parts get much more cleaning than others. While we each have our own rooms in Sir’s house, we often sleep together when Sir is otherwise occupied.

After we dried off, I put my heels back on and walked to the next room which was mine. I needed to redo my makeup and put on the apron I would be wearing until someone removed it. It barely covered my tits and while there was a flap in front that covered my cunt there was also strap underneath that went through my crotch to attach to the waist belt in the back. Laid out with the apron were the dildo and plug that the strap would help hold in place. My cunt was wet enough for the dildo to slide in easily. I used copious amounts of lube in my ass before inserting the plug, knowing the plug would not be the only thing needing lube in my ass that day.

Sir stopped by as I was finishing dressing to make sure I was ready. He tightened the crotch strap two more buckle holes, pushing the dildo deep into my cunt. He also pulled a remote out of his pocket at turned the dildo onto a low steady vibration. He swatted my still sore ass, told me to greet people at the door, and went to check on Susan.

I was met at the door by Roy, one of Sir’s employees. He was dressed in a tight well filled out speedo and was there to offer to help greet the ladies and to take any equipment bags from Sir’s visitors to the dungeon. He is straight and provides services to some of Sir’s female guests. We had met before and while he loves to enjoy looking at me, he treats me with respect, and we get along fine. He also helps with any heavy lifting during the day, though where was he when I was handling the big ice bags?

Susan joined us just as the first of Sir’s guests arrived. This was Sir’s BDSM group and both Susan and I knew most of them quite well. We greeted each of them with an offered kiss and received gropes and swats in return. There was an overwhelming negative reaction to the belts through our crotches which tended to act as chastity belts keeping stray fingers out of out cunts and asses. I thought it might have been Sir’s intent because it did tend to keep things moving in the small reception area.

When most of the expected guests had arrived, Susan left to start taking care of drinks and other services for the guests. One of my favorite couples arrived soon after. She hugged me and gave a deep long kiss while her partner nuzzled tight against my ass, reached around and abused my nipples, pinching and twisting them, causing me to moan into his partner’s mouth to the delight of them both. As they released me, she commented, “We need to talk to the Lord of the House and put in our reservation for this one.” The Lord of the House, and my Sir’s name is John, aka Sir John, aka Master John. I call him Sir which is his preference for me to use.

The young man helping with the bags to the dungeon had a RSVP list and told me everyone who had replied was here. We closed and locked the front door. Anyone who showed up without doing a proper RSVP would have to text and talk to Sir before being admitted.

As I moved to join the party, I met Sir at the bottom of the stairs. He was dressed in a swimsuit and a Hawaiian shirt. I told him all the guests had arrived and Susan was tending to them. Sir asked if there were any issues and I told him about the guests being unhappy about our crotch straps acting like chastity belts, frustrating their enjoyment.

Master laughed and said that was their function, as well as keeping Susan and I on edge. He pulled the remote out of his pocket the vibrator in my cunt stepped up two speeds. I found out later that Susan’s did the same. Sir explained that the caterer had prepared a tumbler of punch for each guest. It was a rum punch and would be the only alcohol served today due to the scheduled open dungeon. Each guest was to receive their tumbler and no more. If someone declined theirs it was to be returned to the caterer.

I got the first tray of tumblers and started distributing them. Most of the guests had shed their clothes and were naked, or nearly so. I noticed Susan had a tray of canapes and was offering them around. Both of us were receiving lots of touches, gropes and swats on our asses as we made our way around the group. I emptied my tray and went back for the second one. Out of the twenty guests only four declined the punch, which I returned as directed.

When I got back to the kitchen Sir unbuckled my crotch strap, removed my apron and handed me a tube of sunscreen. Susan and I had already applied sunscreen to each other after our shower, but Sir said to take it and have someone apply a thorough coating, he didn’t want to beat sunburned asses.

I took the sunscreen and immediately found my favorite couple. I knelt at their feet and begged them to please apply the sunscreen for me. They almost fought each other over the sunscreen, before agreeing that he could take my front and she would do my back. I stood and soon had four hands caressing my body. He started with my arms before moving to my chest as she started at my calves and worked her way up to my ass. I kept having to spread my legs wider as she worked.

I wasn’t sure he was ever going to be done applying sunscreen to my tits, though she spent an equal amount of time making sure my ass didn’t get burned, at least not by the sun. She worked up by back and did my shoulders before repeating what he had done on my arms. He worked down across my abs and spent quite a bit of time making sure I didn’t get burned on my cunt though the dildo frustrated him, by not allowing him to apply any internally. Once he finished my legs, he sat back down in the chair.

She turned me so I was standing, straddling his legs and facing away from him. She told me, “Let me do your pretty face, I don’t want it burned either. Sit down so I can reach it easier.”

As I started to sit on his lap, I felt the plug pulled from my ass, and as I slowly sank into his lap he guided his cock into my ass. I kept sinking his cock going deeper into my well lubed ass until I was sitting on his thighs, my legs spread outside his knees. She leaned in and kissed me before starting to carefully apply the sunscreen to my face. As she was working his hands came down and explored my cunt around the dildo and ran his fingers around and across my clit, before palming my tits and starting to abuse my nipples.

With her caressing my face, his cock in my ass pressing the vibrating dildo hard against my G-spot and his hands teasing my clit and abusing my nipples I was on edge and about to have a very vocal orgasm. She sensed this, slapped my face, and muffled the resulting scream and orgasm by sealing my mouth with a kiss, her tongue deep in my mouth. I’m still sure my orgasm was noticed by most of the group. My body went rigid, my hands formed fists, and I moaned loudly into her mouth as the hard contractions ran up and down my cunt.

Between feeling the dildo vibrating against the tender bottom of his cock in my ass and the strong contractions of my orgasm through the thin membrane separating my cunt from my occupied ass, I felt him swell and pulse after pulse as he unloaded deep in my ass. As he came, he pinched and twisted my nipples even harder, resulting in another round of moans into his partner’s mouth.

I sat on his lap trying to recapture my breath as he strummed my newly bruised nipples and kissed my shoulders as his cock slowly softened in my ass. His partner was beaming with pride at what they had done with me. She leaned, gently kissed me and whispered, “Good girl.”

As I felt him slip from my ass, and replace it with my plug, I slid down onto the deck turned and gently licked and sucked is cock and balls clean as I looked into his smiling face and eyes. I heard him say to his partner, “We need to get first claim on this for the dungeon tonight.” I kissed his cock and balls and as I stood, got another deep kiss from his partner.

I walked back to the kitchen to see what needed to be done. Sir was there and said, “I see you are taking good care of my guests, good girl. Take off your heels, they need a toy in the pool.” He pulled the dildo out of my cunt and the plug out of my ass, giving both to me to lick and suck clean.

Being a pool toy is a free for all on the toy, lots of hands, lots of cocks and a few cunts enjoying the toy. The trick is to go with the flow, mostly it is just being passive and enjoying it. If it is in your mouth lick and suck it. If it is to your lips, kiss and lick it. If it is in your hand stroke it. If it is in your cunt or ass, ride it. Only resist if you need to come up for air.

There seemed to be more ladies in the pool than usual. It kept my tongue and fingers busy while my tits were groped, my nipples abused and either my cunt or ass continuously occupied. It was fun but exhausting. After about an hour Sir showed up with Susan in tow and helped me out of the pool. Susan got a cheer as Sir pushed her into the pool. Sir put his arm around me and led me back to the house and up to the master bathroom. He had me kneel on the floor while he filled my ass with an enema, before helping me onto the stool to release it and flushed my cunt with a cold douche. The water in the stool looked like milk by the time he finished. He eased me into the warm water of the bath and told me to relax. The bath warmed my body, helped my muscles relax, and washed all the juice and cum from my skin and hair.

Sir returned as the water was starting to cool, took a washrag and had me stand as he washed my entire body. Then took a towel and carefully dried me off, noting the bruises on my tits, ass, thighs and elsewhere. He wrapped a towel around me and walked me to my room and told me to take a nap. I was exhausted from my time in the pool and fell asleep almost immediately.

I woke up to find Susan naked in bed with me. She had apparently gotten the same treatment from Sir when her time as a pool toy was up. I spooned up against her, wrapped my arms around her and held her tight. We slept that way until Roy came in and kissed me awake.

Roy said, “Time to get up, dinner in half an hour. Your clothes for dinner are on the chair.” Roy then kissed Susan awake and repeated the message, telling her that her clothes were in her room. Roy left, I kissed Susan and headed for my bathroom. I used the facility and did my makeup, dark like Sir likes it with bright red, non-smudge lipstick.

The clothes for dinner were classic kajira, a single piece of cloth with a hole in the middle for my head and a rope to tie around the waist to hold the two halves in place. There was also a set of wrist and ankle cuffs and a heavy leather collar. A set of six inch stilettos finished the clothing. I met Susan at the top of the stairs, and we descended holding hands.

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