Kay Wins a Bet Pt. 01

Stunned, I watched as Kay laid down several sets of cards and then played the rest of the cards before smiling at me smugly. My cards were obviously going to put me over the top. "Cheer up big brother! You know that while I am good at Rummy, I am even better at other things!" She laughed and I pushed back from the table, taking in the glee of her countenance.

Kay is three years younger than my 60 and looks even younger these days. Her round, brown eyes were almost giggling at my discomfort. Since we were teens, we have always been both close and competitive. We hate losing to each other but would rather lose to each other more than anyone else. Since entering into the "empty nest" phases of our marriages we had reconnected and at times, butted heads, but over the last decade... let's just say we have become... closer once again.

"You win. So, what will it be?" I asked in a resigned fashion. The week before I had had to put on a dress (she provided) and do her dishes and laundry and get her snacks for almost 3 hours!

She locked eyes on mine and dipped her chin in challenge. I swallowed because having known her all of my life, I knew exactly what that look meant. She was about to make a declaration in which I had two choices: Accept and make her happy or reject and really piss her off! She barely blinked as she continued to stare at me. Her fingers rose to the top buttons of her husband's flannel shirt that she had thrown on when we had returned from dinner. Without rushing at all, she undid one button, and then the next, while daring me to allow my eyes to dip down to see how much of her prodigious cleavage she was revealing!

"How horny are you, big brother?" she asked the question quietly and there was more of a threatening edge to her tone than a teasing joke. "Tom has been gone a week and I still have another week to go before he comes home and you know how I hate being a sex camel!"

I swallowed what seemed to be dust in my mouth. I allowed my eyes to dip to see how her large, heavy breasts now showed quite a bit of deep cleavage. My wife was on an outing with some of her friends and would not be back until Monday... It was Friday evening. Early on Friday evening! "Damn it, Kay. Am I ever anything less than horny when you are around?"

Kay smiled, a very satisfied smile and got up from the table and walked over to a cabinet. I collected the cards on the table, stacked them neatly as I listened to her first open first one cabinet and then a second and pour some water. I was just putting the playing cards back into their box when she walked back to the kitchen table and stood very near to me. Her shirt was now unbuttoned all of the way down. Her breasts were covered, but just barely.

"Here. No questions, just take them." She put the glass of water on the table and beside them; 2 small whitish round pills.

I looked from the pills up to her face and back down to the pills. I was about to say no, but as my eyes went back to hers, they moved over the creamy flesh of her stomach, the rounded sides of her breasts that formed her sensual cleavage...then her eyes that were full of challenge. I had seen that stare before. It was the stare of ultimatum. In the past, when I had not complied there had been dire and irreversible consequences. When I had complied...we had gotten into trouble on more than one occasion, but we had also had a hell of a lot of fun on others.

I reached down and popped the pills into my mouth and washed them down with a large gulp of water.

"So, may I ask what I just took?" I asked. I tried like hell to keep my eyes on hers, but... with her standing a bit over 5 feet in height and me sitting down... her boobs were like a siren's songs to me.

She hesitated for a moment and then said, "Baby aspirin." She smiled big and placing a pill bottle on the table she added, "These are Sildinafil, I think you know them as generic Viagra. You have a choice to make, as the loser tonight. One: you can spend most of the day tomorrow cleaning out the chicken coop for me, and it will take you most of the day or Two: You can take two of those pills and then one more, every two hours for a total of 5 pills...."

"Why would I need Viagra?" I asked. It was true, there were times...more frequently lately, that I needed some pharmaceutical assistance in the bedroom, especially staying hard, but....

"Because, what I have planned is the opposite of a 'wham, bam, thank you ma'am' romp. I am thinking 10-12 hours of me working out my sexual frustrations and kinks. "Tommy cannot take these any more. He gets migraines from them, so... He takes good care of me in other ways in the bedroom. But if you choose option two, you will be filling my pussy, over and over again and not emptying a bunch of chicken shit tomorrow."

My eyes slid down from hers and in response, she took a deep breath, widening the gap of her shirt. Just the hint of an areola peaked out and I could see both nipples hardening and lifting the fabric out. My own body was having its own responses. I forced myself to also take a deep breath, as the infrequent shallow breaths had my head spinning (at least that is what I will blame it on!). Lower, at the base of my torso, my balls were beginning to "rearrange the furniture" as my manhood was also beginning to chafe at the confinement it now experienced. I picked up the pill bottle, slid two small pills into my palm and then looking Kay in the eye, I popped them into my mouth and picked up the water and washed them down.

Kay stepped back from the table as I stood up and she pulled her shirt closed. "The rules are, whatever I say are the rules, for tonight."

I moved toward her to take hold of her hips and pull her to me, but she put her hand on my chest while still holding the flannel shirt closed. "You go take a shower, and make certain you have removed every hair from down there! If you don't, I might just have to remove every stray hair with tweezers... one at a time!" I thought seriously about just pushing her against the wall and taking her. Being a foot taller than she is, more than 100 pounds heavier and a lot more strong than her, I knew I could take her....

I got out of the chair, turned and walked down the hall to do as she had ordered. She had 'plucked my pecker' once before when we were both in college and... I knew I had better be very thorough!

------------

I normally keep myself rather "well groomed" down there, but.... I took my time and made every effort to get every single hair. I was just finishing up when the door to the bathroom opened. "Here's a little extra gift for you." Kay said as she walked into the room carrying a small brown bag. The bag barely caught my attention. She had changed into a white tank top wife beater and black panties that left little to the imagination! She looked over at me as she set it down on the counter and smiled at me. I was naked and suddenly very aware that her appearance was having an effect on me all by itself! "Maybe you are right.... maybe you really didn't need those pills." She smirked as she turned to go out the door. At the last moment, before she turned up the hallway toward the master bedroom she added, "But you will need that...every bit of it!"

I stepped out of the still dry shower (I find it easier to do my "manscaping" in the shower) and looked into the bag. It was a premixed enema bottle! I turned and looked at the now empty doorway and for a moment thought about asking what the hell she had in mind. But then I knew. "Fuck...." I swore softly as I pulled the plastic bottle and nozzle combo out of the bag and threw the crumpled bag into the trash can. "I guess she wants me clean, inside and out." With a sigh, I lowered myself to the floor and assumed the head down, knees and feet on the floor, butt in the air position that I had had to use a few weeks earlier for a colon screening test.

Suddenly, Kay stepped back into the room just as I had lined up the nozzle and was starting to push it in. "Mind if I give you a hand?" she asked. I started to turn around but she grabbed the bottle with one hand and my wrist with the other. She then stepped up beside me and 'mounted' my lower back facing away from my shoulders! She allowed me to help guide the offending plastic into me and then removed my hand. I could already feel the room temperature liquid dribbling into me. "Let me know if I get going to fast." she said with a laugh and then I felt myself get full quickly! After a moment she slapped my ass hard; first with one palm and then the other! I jumped! "That's it! Shake your ass for your sister, big brother! Work that stuff deep into you, I want you ready, willing and able for anything!" She then reached over my ass and grabbed my nut sack and pulled it back and up toward her! I jumped again and immediately felt the liquid sloshing in my bowels and spilling further up into me.

Fingernails, slaps, and ball tugs were punctuated with her grinding her pussy on me with only the thin cloth of her panties separating us! She would croon and tease and then push more of the diabolical fluid into me. It was probably no more than a minute though it felt like an eternity before I felt the first gurgle and roll deep within my bowels. As I squirmed from all of the things that Kay was doing to me, including grinding her wet pussy on my back, I was also stirring my own innards into a frenzy.

With a hard, double hand slap to my bottom she got up off of my lower back, pulled the nozzle out of my ass and tossed it into the trash. "Don't make a mess of my bathroom, but I do hope you will hold out until you are really completely and thoroughly cleaned out!" And with that, she hit the exhaust fan on her way out the door.

Several minutes later, I arose from the porcelain throne, uncertain whether the sudden stillness within me was the quiet before yet another storm or the proclamation of my body that my tonsils could now be seen from my ass! I have had to do the 'Royal flush' before, for medical reasons but whether it was the unexpectedness of having to go through the process or it was the additional agitation from Kay, I have no idea, but I felt completely hollowed out as I flushed the toilet one more time and stumbled into the shower to thoroughly cleanse my outside to match my insides!

I felt totally rejuvenated once I had stepped out of the shower and toweled off. I pulled my toothbrush out of my toiletries bag and brushed and gargled before contemplating putting at least my underwear back on. "Why waste the time," I muttered to myself and set out to the Master bedroom to see what my sister had planned next!

She was sitting on her bed, back against the headboard, filing her nails. She now wore only the thin white wife-beater which did little to restrain or hide her large breasts and hard nipples. "Oh good! I was afraid that you had followed yourself all of the way down the toilet!" I bit back the retort that zipped into my mind as I tried to remember that she was going to hold my future as well as some other rather important items to me in her hands over the next few hours. "Could you go into my bathroom and get some warm water in the bucket I have in there and bring the other things out?" I started to say, "Sure, what are they for?" but I figured I would find out soon enough. Instead, I turned and went straight into her en-suite to retrieve her items and water.

A few moments later, when I returned, Kay was now lying on her back, knees just at the edge of the bed, and a pillow covered in a towel under her hips. Her pussy was on full display and even before I came to stand between her knees it was obvious that she was already wet! I sooo wanted to reach out and touch her... "Take the wash cloth and wash between my legs. And then, just make certain I am clean shaven down there, would you please? And you better not nick me or there will be hell to pay!"

I have never been afraid of a pussy before, but as I knelt down and put the bucket, razor, shaving cream, washcloth and baby oil on the floor next to me I have to admit that there is a first time for everything! Kay has the most beautiful pussy! Her lips retract normally and maybe a only a half inch of them is visible when she is calm. But when she gets excited, they puff up and their rubbery texture stretches and forms the most inviting places on the earth to explore! Wet as she was now, she had already been touching herself and when she suddenly opened her legs wider I nearly said to hell with what I was supposed to be doing and dove face first right into her! Taking a steadying breath, I soaked the wash cloth, wrung it out and cleaned her up before spraying out some shaving cream and then smearing it all around her inviting sex!

I took my time and in a stroke of diabolical genius, I turned the tables on her a bit. I pinched her labial lips and pulled (and massaged) them as I 'examined them for and stray hairs' and took my time cleaning every nook, turn, twist and fold of her nether regions! By the time I had worked my way back up to the hood of her clit, she was moaning and the dew was now beginning to flow.

Which was good, because my cock was now at full attention. It's tip had released several singular drops into the bucket that I had strategically moved to directly in front of me. As I wiped the remnants of soap, water and the few hairs I had found, off of her now oiled and shiny pussy, it was all that I could do to stay on the floor and not stand up and ram myself balls deep into her excited flesh!

"Alright, alright. Get up on your feet and face the wall." She said as I finished patting her dry with a hand towel. I did as I was told. She picked up a hand mirror and checked my work as she then instructed me to take all of the things I had been using back to the bathroom. When I returned she was standing beside the bed and peeling herself out of the shirt! Immediately I was on full alert. She motioned for me to come and stand in front of her which I was more than glad to do! She leaned over the bed and reached under the pillows she had been leaning back on and produced a pair of stainless steel police issue handcuffs. "Hold out your hands."

My heart was suddenly a set of timpani pounding in my chest and head! I had trusted Kay with nearly everything my whole life, but the one thing I had always been able to do was overpower her, if I needed to. She raised her one eyebrow and gave me the look of, "Don't tell me you are going to challenge what I am telling you to do?!?" But still, if I let her put those manacles on me, I was going to be completely at her mercy and that was something I was not ready to do... at least not lightly.

I took a deep breath and held out my hands. Kay gave me one of her smirks as if to say, "I knew you would cave" and promptly locked them and set them so they would not tighten any further. "The reason I am handcuffing you is it has been about an hour since you took your pills and I am going to take my shower now. I want you to watch me shower, but I don't want you to touch yourself, so.... Handcuffs." And with that, she took hold of the chain links that joined the cuffs and led me into the bathroom. She tossed a folded towel down onto the marble tile and had me kneel down facing the shower.

She was right to have me restrained! I watched as she walked around naked, getting ready for her shower and within moments, the whole scenario of kneeling in the middle of her bathroom, both of us naked, was erotic to say the least. I could not help but think back to watching her grow up. I remember looking at her before she understood why I would peek in on her taking a bath or the times playing in the small backyard pool we had the one year where I was continually pulling on the strings to her top... just to catch a glimpse. Then later, as we both developed... We had grown up together and had taught each other a lot.

But the woman that moved around me was different. Not much taller. But it had been more than 5 years since I had last seen Kay naked. She had been a full figured woman then and now... her breasts hung down more, her hips were a little bigger... and my cock was growing more hard with every minute that I waited for her to enter the shower. Before stepping into the shower, she had me put my hands on my head "as a precaution." She had then stepped into the warm spray and begun to wash her long hair. In a very real way I wished she would invite me into the shower to help her wash her hair, her back... her ass and tits.... But she took her time showering, holding up first one breast into the spray so that I could see it glistening in the water and then the other. She lifted the second breast to her mouth and tucking her chin, sucked in the whole of her nipple in and I could see her jaw, and tongue moving the muscles in her face as she sucked on her boob and stared into my eyes. Staying on my knees was sooo fucking hard!

By the time she was done, there was a small puddle of pre-cum on the floor in front of me, as my rigid cock danced unabashedly in front of me, pointing at her. It was almost as if the one eyed monster was also seeking to look at her curves, rolls, handfuls and more... She smiled at me and turning back into the shower, grabbed her washcloth and tossed it so that it splatted against my chest and fell in front of me. "Clean your mess up and then go lie down on the bed." Then she stopped and walked to right in front of me.

"Suck me" she said as she held out one of her G cup breasts for me. I immediately rocked up higher onto my knees and eagerly wrapped my lips around her nipple! I have always loved Kay's breasts, but her nipples have always been my favorite nips in the entire world! When they get hard, they get long, thick and as you nurse and suck on them they continue to grow, tighten and change from one moment to the next! Sucking on them when they are so responsive is only made better by the fact that she loves having them sucked and once even confessed that she had had many incredible orgasms just from having them sucked on!!

I made it my mission to make this, one of those times. She reached behind my head and brought my hands forward to hold the breast I was sucking. Then I watched as she lifted her other breast so that she could suck on it as well! Our eyes locked for a moment and she shuddered before closing her eyes and concentrated on the sensations she was having!

The sensations that I was having were... no less intense but not nearly as wonderful! I was harder than I had been in a very long time and my balls felt as if they were ready to draw all of the way up into my torso! I tried to move so that my cock might touch her knee or shin or... anything, but she was careful not to allow that and so I sucked on her breast as she sucked on the other. Suddenly one of her hands went to the back of my head and she pulled my face hard into the pillowy luxury of her wonderful womanly endowments and she swore and told me to never stop sucking, right before she slipped into growls and unintelligible grunts and cries.

With as sudden a movement, she shuddered and I thought for a moment she might fall down, but instead she pulled me off of her nipple and then stumbled a step or two back into the glass side of the shower. Her complexion was going from flushed red to almost a pale as she dropped her breasts and fought to stay upright. She stood there before me, feet spread slightly apart and a single silvery thread of a thick fluid held in suspension from her wet and very obvious labia. It was like a primal call to the core of my being to take her and use her! But instead I waited.

"Clean up the floor and go lie down on the bed and wait for me." Kay finally said before opening one eye and adding, "If this keeps going this way, neither of us are going to get any sleep tonight!"

I reached down for the washcloth and silently wished that I was a few years younger... and more vigorous!!