Ay Wins a Bet

I had not been asleep for very long when I heard someone moving in the room. For a moment I thought someone had broken into my home, but then I remembered I was at my sister Kay's house, in her bedroom... and very much naked! I smiled at the memory of why I was naked and so relaxed!

"Ahh, it's about time you woke up! I was just about to leave you with no option!" Kay said.

"I just had the most wonderful dream in the world. I had been teased forever and then I got to fuck you." I opened my eyes and looked toward the part of the room where her voice was coming from. I realized I was becoming erect again, but this time it was a trip to the bathroom that was needed.

"Yup, and now it is my turn to fuck you!"

It took about 1.6 seconds after the sound to reached my fuzzy brain, for me to question whether I had really heard and understood what Kay was saying and then to open my eyes wide to confirm my fears! "What the hell....?" Kay was standing just a few feet away. She had some sort of male looking underwear up to her knees, but it was what she had in her hands that my mind was having trouble comprehending. It looked like a dildo...that had been welded in an almost V shape to another dildo... It was purple and she was lubing up the shorter branch of it and as I watched she began to work that glossy silicone up into her bare snatch! "What are you doing?!?" I asked, half afraid to find out.

"You didn't think I had you shit yourself royally for no reason did you?" She smiled at me angelically and then stood upright and without holding onto the phallus, shook her dong at me with her hips! "You like?" She asked quite pleased with herself.

"What is it?"

"It's called a FeelDoe. It is a double ended dildo intended to be used in a more conventional, missionary or doggie position than most of the old double ended toys!" Now she was absolutely bursting with pride over knowing something sexual that I did not know about.

"I have to go pee." I muttered as I stood up and shook my head. Kay's smile fell a little, so I stopped and grabbed hold of the part of the toy that was poking out lewdly from beneath her. Giving it a slight tug toward me she took a half-step before her nearly naked body collided with mine. Before she could protest, I leaned down and kissed her hard on the mouth. She resisted a moment and then I felt her decide to go on the offensive, taking over the kiss in a very aggressive manner.

"You better go pee," she managed to gasp as we both were following our tongues in plunging deeply into a resumption of hot and heavy lust. Giving her breast, which I had grabbed in my other hand, another squeeze I turned and shuffled into the master suite bath.

My mind was racing a hundred different ways suddenly. I looked at my watch and realized it was only 1:40 a.m! I had not even been asleep for half an hour! No wonder my mind was in a complete fog! Additionally, my cock was suddenly having trouble 'switching the piping over' from 'prepare to fire the cum cannon" to 'relieve this very full bladder' mode. Taking a couple of deep breaths, I relaxed and finally got things flowing. That was when the realization hit me. I was aroused by the thought of Kay fucking my ass!

Now, it is no big secret that my asshole has always been very sensitive and agreeable to being played with! Both my wife and Kay have known forever that running a finger over the starfish flesh of my bum will almost always push me right over the edge while they are giving me a handjob or blowjob. I have always loved that touch! And a little push against the center of it, increasing some pressure, along with rubbing the prostate through the taint. mmmmm, yeah, I am not afraid to admit to being at least curious about getting something pushed into and up my exit! But to date, it had never happened, and I really thought I might be a little more..nervous about it!

I shook out my last drops and squeezed out any remnants of urine into the bowl and washed my hands. "Hey, I have some orange juice in here for you to drink. You have pumped out a lot of... fluids this evening! Can't have you getting dehydrated and cramping up on me!" I laughed as I dried off my hands and walked back into her bedroom

Kay was standing there at the foot of the bed, big purple cock jutting out of black, skin tight latex men's underwear, a pile of pillows in the center of the bed and big glass of orange juice in her hand. "I aim to please." she said. Then she brought her other hand out from behind her back. It had a blue surgical glove and a large tube of lube!" She laughed as I stopped and stared at her. "Oh, damn. I wish I had my camera! That look was priceless!"

"Yeah yeah," I said. Sure, I had stopped dead in my tracks at the realization that this was all really happening! But I was not going to back down from my little sister! I took the glass of orange juice and started to raise it to my lips before I stopped and asked, "So what did you spike this with this time?" Kay looked at me completely lost and then burst out laughing.

"I'm sorry. I... I didn't put anything in it. You just have... how shall I say, put out a lot of energy tonight, and I want you to keep put out...lots of... energy!" she said before bursting back out in another fit of laughter. I watched her carefully for a moment more before lifting the glass to my lips and draining. I had not realized how thirsty I was!

I set the glass down and said, "Now that hit the spot."

Kay started laughing and grabbed her rubber phallus. "If you think That hit the spot, get up on that bed and lie over those pillows and I will show you a whole new meaning to 'hitting the spot'"! Kay, as usual, highly amused herself and she tried to keep from smiling as I stood, a foot taller than her, just looking at her as deadpan as I could.

"Look, I'm not sure I'm..."

Her humor dropped like a cement block off a building... "Like hell!" She declared. "You told me years ago that the one thing you wished you had let me do to you back when we were both living at home was when I wanted to fuck your ass and you said, no! You told me that probably 15 years ago and you have no idea how many times since then I have thought, 'Well, hell, I still want to fuck you!' Don't you even think you are leaving me hanging again!"

"So,... What do you want me to do?"

"On your knees and suck it, Bryan. I want to look down at you the way you have so many times. I want you to show me that you worship me. That you will do whatever I want just because you want me that much." Staring daggers at me she grabbed my balls and in a threatening whisper she added slowly, "So I want you to get on your knees and suck my cock...now!"

I slowly sank to the carpet and looked up at Kay. Seeing her face, bracketed by those huge, heavy hanging tits, her eyes on fire with lust and desire... there was no way I could resist. I leaned up and took the cock and put it between my lips and sucked it into my mouth. Kay had used a strawberry flavored lube on the cock. She reached over and grabbed her phone off of the dresser. A moment later I felt the vibrations somewhere down low inside of her begin buzzing my lips. Her eyes glazed as she took a deep breath and tossed the phone onto the bed. Looking back down at me she blew me a kiss and slowly began thrusting her hips in and out of my face.

I could not help myself. I have never considered myself gay or even bi-curious, but I began making love to Kay's cock. Looking up into her face for approval, I licked its length and sucked on it and around its head. She scooped her right breast into one hand and lifted it to her own lips as she stared down at me. I watched as she began sucking her own nipple and her eyes fluttered closed as she lost herself in the sensations washing over her body. I reached around and grabbed her ass and guided her slow thrusts into my mouth!

My knees were getting tired as was my mouth when her heavily lidded eyes opened and she said in a husky voice. "I don't know about you, but I am ready to fuck you now. Get up on the bed." I did not hesitate, I immediately crawled up onto the bed and rested my belly across the pile of pillows in the center. "Ass up, head down!" she said with a chuckle!

I heard the squelch of the goop being pushed out of a tube and then the click of a top being closed moments before she climbed up on the bed behind me. The gel was damn cold and I let out a short oath. Kay told me to stop being a bitch and then gave a chuckle. A moment later, a single finger of hers slipped into my ass.

I don't know what I expected, but... there was a lot of pressure, and then I felt her fist against my cheeks. Her finger tip began stroking something inside of my near the very root of my cock and without thinking I groaned. "Oh, I love that! You sound like a little whore. Do it again!" she said as she continued to explore my insides. There was a jab at one point that hurt like hell and she knew it, but soon I felt myself relax and then a second finger joined the first. The lid on the lube opened again and I heard her squeezing out more of it just before the icy mass slid all over my sphincter.

"Look the other way, to your right," I heard her say. I did and I realized I could see Kay, mounted behind me. "I want to watch your face when I put this into you." I heard her say in a voice that was so full of lust that I almost did not recognize it. I smiled at her and I watched as she looked down and pulled her fingers out of my butt and quickly wiped them along the shaft of her phallus and placed it against my asshole. "Back into, my brother. Take it, take it all!" I took a deep breath and as I let it out slowly I relaxed backwards against the thickness that was pushing against me.

It surprised me, because the moment the mushroom entered me, another couple of inches of the shaft slid in as well. I went from feeling oddly empty with her fingers gone, to feeling pressure way up into me! "Easy... easy.... I'm in! Just relax." she crooned. I could feel the slight vibration of her toy buzzing my circle of flesh and I tried to relax. I watched as she leaned forward over the hump of my ass and kissed my shoulders and back. Instantaneously, the hairs on my back stood on end and I shuddered. "Oh my! That was mmmmm do it again!" she whispered as her lips moved over my flesh, her nipples barely touched the dip of my spine and the vibrations intensified as she pushed into me. She got what she asked for as I shuddered and moaned.

Kay reached over and changed the settings on her phone. Now the vibrations began rising and falling in intensity. Then she squirted a large glob right into my crack, which she then smeared over my anal region. I watched as she then stood up, legs spread to either side of my hips and slowly sank down, pushing the whole length of her cock into me. "Come up." Kay said. "Lift your shoulders." she clarified. I did and a lot of the pressure that had felt like she was going to rip the top of my ass disappeared. It had evidently relieved pressure on her too, because I saw her face relax. And then it began.

Leaning forward and resting her palms on my shoulder blades, Kay began to slowly fuck me for real. In and out she slid and with each penetration I relaxed a little more. soon, the tip was gliding back and forth over that spot deep inside of me that felt...mmm so good. My own cock was being driven into between two pillows, so I was fucking the bedding as she fucked my ass at an ever increasing pace. "Yes, take it Bryan! Take my cock! Oh yes!" She was slowly building up speed and losing herself in it all.

She suddenly pitched her whole weight down the length of my back, pushing us both to the bed. She continued to fuck my ass, but at the same time I felt her teeth and lips biting and sucking my shoulders, back and neck. "Kay, stop!" I said, but she laughed and kept on both pounding her hips against my ass and the rubber cock into my belly. Her fingernails began raking my flesh and my protests dissolved into moans of surrender. The intensity of her every touch, from her hips, to her fingers to her lips to her nipples to her legs bracketing mine all felt divine!

Then she pulled out of me and rolled over onto the bed. She was hot and covered with a sheen of sweat. I turned and immediately started sucking on the nipple closest to me. She wound one of her fists into my hair and crushed my face to her as I sucked and tongued her nipple. I love the way that Kay's nipples swell and elongate, hardening and changing shape with nearly every slurp, tongue slap and bite! "Stop. Hang on." I heard her pant. She started to shove the pillows off of the bed and I helped her as she then took one pillow and leaned it against her headboard. "Come up here," she commanded as she leaned back on the pillow and caught her breath. I moved immediately to kneeling in front of her and started to lean over her to suck on her nipples again, but she stopped me. "Get on your back and put your heels on the wall."

At first it did not make any sense and then.... I quickly scrambled to get my ass up close to her as I laid on my back. "You are such a butt slut! If I had known this...."

"If I had known it, you would have gotten to do me all those years ago!" I finished. She laughed and slapped the insides of my thighs before slowly bringing her hands together around my straining cock. When she asked for the lube, I quickly found it and her phone and passed them up to her. I think she turned off the vibrations, but she also lubed up the shaft and re-entered by ass. Then she looked down on me and said, "I think this might be the best of all worlds for you!" I had to agree as I could slowly fuck myself on her cock, look up at her and those incredible G-cup boobs.... and then her hands began to stroke me.

Now, my wife has stroked me to get me off 90% of the times we have played in the last dozen years since she started into menopause. It has simply been about all that she has been comfortable with doing! But as many times as she has stroked me, she never once did it like Kay... Oh my God. First, her little hands just wrapped around my cock and balls so perfectly! But the way she used her thumbs in a milking motion and then would rub her slick palm over and over the tip of my dick... It was divine! And yet, she brought me to the brink no less than a half dozen times and then would pull her hands away, only to slowly start my torment all over again a minute or two later.

It was almost 3:00 a.m. when she grabbed one of my legs, and pushed me up and off of her cock. I watched as she pulled her panty down and then slowly eased the FeelDoe dildo out of her red and irritated cunt. Without any ceremony she rolled me onto my back and took my throbbing cock that had been denied far too many times to count up into her. Leaning forward she pushed a nipple into my mouth before quietly saying. "Fuck me now, Bryan. Fuck me and we both can sleep! But you have to pump me full of your cum! I want it all!" Then she shuddered as she lowered her hips over mine and I slid into her.

Neither one of us were in any shape for a marathon at this point. It really was not even frantic. It started off a little aggressive, but when her arms grew weary and she fell onto my chest, we both slowed. We were no longer fucking, we were not even screwing. I made love to my sister, possibly for the first time. Our tongues played, fingers roamed...and my cock danced inside of her ever tightening pussy. I could feel her juices and the lube running over the base of my cock, over my balls and down the crack of my ass onto the bed. It did not matter. All that mattered was we were each slowly getting to something that we had wanted for a very long time.

Her tightening down at the very start of her climax sent me thundering over the edge and into the abyss. She flooded me with her juices and I pumped over and over into her pussy, so much of me that I was certain I was going to turn inside out, right through the end of my cock! For several minutes, we triggered aftershocks, tremors and giggles through one another before I finally softened and slid out of her. It was like I had uncorked a bottle of something, because our cocktail of cum sluiced out of her and she intentionally slid quickly up my body, painting me with it all.

"Looks like you need another shower!" She proclaimed with a giggle as she finally dismounted from my upper chest and dropped back on the bed.

"I don't think I'm the only one!" I shot back.

"True, but I have to strip the bed and get the pad off of it." A few minutes later, we were both laughing as we pulled the soiled sheets from the bed and I took them and the pad downstairs as Kay remade the bed.

The great thing about showering with Kay in her master suite is that you could literally have four or five friends join you! We laughed as we washed each other and then toweled one another off.

It was 3:33 a.m. when I looked at the clock as I climbed into the bed. "Why does your bed crinkle and feel...like this?" I asked as I rolled over to make room for her.

"Oh, that's the pad, you know. To collect any of the extra mess we might make."

I raised my eye brow and looked at her. "You want more?" I asked almost too drowsy to care.

"You never know!" she said back before yawning and turning out the light. She rolled into bed next to me, kissed and rolled over.

We both were surprised, as my cock found a its own pillow... between her butt cheeks!