Win or Lose

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Win or Lose[Authors note: This story has a dual ending. You can read through the whole story, pick your preference or if you’re feeling adventurous, grab a quarter and play along. Each outcome starts at either “*** I Won!” or “*** I Lost!”. Enjoy.]My wife has the most incredible ass. Firm, round, with just enough padding to make it wiggle when she walks but splays open enough to show me her tight little pucker when she’s bent over. I’ve been trying to slip my cock in that entrance since our honeymoon. She always resists and resorts to any alternative to satisfy my anal desires. Today, it looked like she had enough…I was sitting on the couch watching TV when she walked up to me. In her left hand was a long rubber, realistic looking dildo. I was a surprised. We always go to sex shops together and she shies away from that area of the store. I was getting hard just watching her hold it.She stretched out her other hand at me and opened it flat. In it was a quarter. “Ok, you’ve wanted to fuck my ass forever. Now you might get your chance. Heads or tails. If you win, I’ll let you but if you lose, I get to fuck your ass with this.” shaking the big rubber dong in my face. I sat for moment thinking, then took coin from her hand and threw it in the air. “Call it”, I said, catching the quarter in my fist. “Heads!” she shouted and I opened my hand…*** I Won!I found a double headed quarter years before we got married and always kept it hidden in the top drawer of my nightstand. I caught my wife looking it over one day. I replaced it with a regular quarter in case she ever tried to use it on me.She had a look of horror as I revealed the tails side of the coin. I got up from the couch, grabbed her gently by the wrists and pulled her into me, then slid my hands around her back to those two tight mounds. “Honey-Honey” she said with a look of fear in her eyes, “You have to be careful”. I reached for her wrist and slowly pulled towards the bedroom. I didn’t say anything in response. Of course I was going to be careful. I wasn’t about to screw up any future chances.I guided her onto the bed on her hands and knees, then a slid the little shorts she wears around the house down as far as they would go. I pushed her shoulders down firmly to the bed, stepped back and took in the view of my wife submissively posed, ready to give me her forbidden entrance.“Be gentle” I heard her say, muffled face first in the bed. I put my hands on the side of each cheek and parted them slightly then lowered my head until her locked anal passage was in line with my mouth, then just rested the tip of my tongue on her entrance. She gasped a bit but made no attempt to move. I started working my tongue in just a little, testing her slowly. She continued to sit quietly and didn’t say a word. I invaded a little deeper, feeling the tight muscle of her sphincter relax until I could almost get through the entire length of the muscle. She let go, allowing more and more of my pointed tongue into her back passage.My constant soft prodding seemed to be working. With a slow undulating motion I could feel her hips start to rotate into my tongue, asking for just a bit more. I knew it was time for the next step.I backed away, stood up and headed for my nightstand. Getting my “wishful thinking” lube I had kept there. Walking back around the bed I stopped to take another look at my wife’s wonderful round bottom with her tiny pucker showing, now shiny with my saliva. I opened the cap and smeared a thick glob of the clear sticky lube on my first finger. Then reached down between her cheeks and started to slowly rub around her pucker. Again, her hips started to move as I circled around her little anal hole.Given the tongue warm up, my wife’s little hole seem to give easily, allowing me to slide my finger to the base. I wanted to give her as much pleasure as possible so reaching under with my other hand touched the pad of my thumb to her exposed clit, gently rubbing it in a circle. Her hips began to move more noticeably. My finger slid in and out her ass in even rhythmic motions, matching the speed of her hips. Her sphincter wasn’t fighting me anymore and seemed to almost suck on my finger as it moved in and out, as if trying to give it little blow job.My hard cock, still trapped in my pants started to strain. It was time to move to the main event. I slid my finger out. I heard a little whimper from my wife once the probing stopped. She was liking adana escort it! I grabbed for my belt and frantically tried to remove my pants. My instincts told me to move quickly before she had a change of heart. I nearly fell over trying to get them around my feet while still standing.With my cock now freed and standing at attention, I looked down at my wife’s round little bottom and glistening little anal hole. It appeared she didn’t want to wait for me and assumed responsibility stroking her swollen clit, slowly circling it with two fingers. I stepped forward and with two fingers, pressed against her opening. There was resistance as her little puckered ring tried to adjust. “Breath, relax and push a little” I said. She complied and with a long exhale, her passage seemed to ease up and swallow my two fingers. I was rock hard and ready to go but wanted her to gradually adjust before moving on. My fingers moved more freely in her bottom, and her hips started moving again to meet the thrust of my hand. The pace picked up a bit along with her elevated breathing. It was time…She kept moving even after my two fingers slid from her ass. Stepping forward I lined my rigid cock up with her shinny lubed hole. Pressing the tip in just a little and let her hips control the penetration. At first she just bumped the tip before recoiling her hips. But with each push back applied a bit more pressure. My cock slowly started to sink into her ass, inch by inch with every gyration. Finally, my shaft bottomed out the base.I was completely in her ass for the first time ever. It so sexually charged I could have cum right there. So I just stayed there buried deep inside her anal tunnel, taking in the sensation of her soft anal walls massaging my rock hard shaft, the sphincter still tightly gripping the base. Looking down at her face there was no sign of pain or discomfort, just the sweet look of pleasure.I hadn’t noticed before but she still had the big rubber dildo clenched fist. Her face turned in its direction. She slowly brought it up to her lips and wrapped them around the mushroom tip, then proceeded to suck on it. “Mmmmm” came from her lips, like she was sucking on her favorite candy.I backed out and pushed in slowly. “Mmmmm” escaped her lips again as I watched her slide more the big rubber cock deeper into her mouth, forcing it back till she gagged a little. Her hips seemed to be in lock step with mine. Every increasing thrust was matched while she pumped the rubber dildo into her mouth. That big rubber cock was getting the wettest blowjob she ever gave. She pumped it with more speed and suction, as if hoping it would somehow blow a big sticky load into her throat.She released the dildo from her grip and let it just sit there embedded in her lips, and brought her free hand down to assist her other hand on her pussy. Leaning her full weight on her shoulder and arched her back to meet my thrusts. I moved faster and with more ease now, every thrust seemed to heighten her arousal. I could feel the need for release build up and increased my strokes a little more.My prudish wife was having her first anal experience and loving it. The whole sight of my rigid cock sawing into her tight hole along with her sweet lips wrapped around that big rubber cock was more than I could take. I started shoving uncontrollably and with enough force that it shoved her forward a bit with every thrust. The rubber cock popped out her mouth and a string of words I’ve never heard before escaped her lips. She started shouting…“Oh yeah… baby fuck me. Slam your hard cock deep into my asshole. Fuck my shit-hole. Stretch it out and go deep. C’mon shove it in. Pump my asshole deep. I want you to flood my poop-hole with her hot cum”. Listening to my conservative, shy wife obscenely beg for more anal pummeling was more than I could take. With a final thrust I penetrated her fully and my hard cock swelled with the first throb. I accommodated her filthy pleading and shot the first sticky jet of cum deep into her anal canal. She moaned and pushed back hard against me. “Aaaaaaaa” she screamed as her own orgasm started. We were both locked together, fighting to get my cock deeper while the next wave cum blew into her insides.I couldn’t tell how many times my cock throbbed and shot stream after stream of cum into her ass. I started to feel a slickness around my cock and looked down to see my cum leaking out around my shaft. I was escort adana filling her anal passage completely.The waves of orgasm started to subside a bit and our motions slowed, still in sync with each other. My cock softened but her anal passage still had enough tightness to keep it in place. We were both entirely spent.Slowly and reluctantly I pulled back. My soft cock flopped out of her open hole. Her sphincter instinctively clenched, forcing a stream of my cum out of her pucker and down her leg. I had no words. Just stood there and took in the whole sight.She lifted up and looked over her shoulder at me and grabbed the rubber cock in her hand again. Then with a little grin on her face said “Next time, you get to try it.”*** I Lost!It appears my wife found my double headed quarter in the back of my closet. I should have hid it better.A big grin swept over her face as I took a closer look at the dildo she was shaking in her hand. It was long, at least eight inches with big veins that ran from the base of the shaft to just behind the pink bulbous head. It had large balls at the base with little realistic looking ribbing. I was concerned about the prospect of my wife getting that to fit inside my virgin ass. She pulled on my hand, indicating she wanted me to get up. I stood and let her take me by the hand to our bedroom. “Take off your pants and get on the bed. Hands and knees please” still smiling and shaking the big rubber shaft in her hand. I lost fair and square so I complied.I closed my eyes and waited for what I expected would be a violent assault on my tight asshole. I felt her finger touch my puckered entrance before gently trailing down my balls and hanging shaft, then rubbed lightly in little circles around the head. The sensation made my cock stir and I could feel it start to get hard. She tossed the big dildo on the bed beside me and picked up a tube of lube she had on her nightstand. Resuming the tickling on my now hard cock with her fingers, she flicked open the lube and put a healthy glob on my tight backdoor. It was cold, causing my pucker to wince.“I’m going to warm you up a little first”, she said, now gripping my cock and giving it a squeeze. She then touched the tip of her first finger on my shinny little opening. She kept slowly stroking my cock, now fully hard and pointing forward as she started to swirl the lube around my opening in little circles. The sensation actually felt great. Now my cock was bulging. Looking down between my legs I could see a drop of clear liquid run down the tip of my shaft. Her finger started to penetrate my tight sphincter.With her finger pointed straight she made a slow deliberate advance into my hole. “Push a little” she said. I did and her finger slid smoothly in to the base of her hand. Still looking underneath me at my cock, the shiny clear fluid started to run a bit more. A long strand started to drip towards the bed. Slowly her finger began to move in and out of my ass. With her other hand she started lightly scrapping the underside of my cock all the way up and over my balls with her finger nails.From behind me I heard a little snicker. Obviously my wife was enjoying the site of her finger penetrating my ass. And given my rock hard, pre-cum dripping cock, I couldn’t deny I was too. She backed her finger out and I started to feel her press two fingers in this time. I gave up and relaxed, trying to adjust to the new size. My anal muscle started to swallow both digits. Her fingers slipped in with much less resistance now. She started a slow sawing motion from the tip of her nails to the base of her hand. This went on for several minutes until she could stuff my anal passage at whatever speed she wanted. I reached down with one of my hands to give my cock some attention. She reached underneath and batted it away “A-Ahhh”, that’s mine to play with. My cock throbbed in the air as if begging to be touched and another strand of pre-cum dripped out from the tip. She slipped her fingers out and reached for the dildo. It disappeared behind me. Then grabbed the tube of lube. I looked around and watched my wife squeeze a big dollop of lube on the tip of the rubber head. She then lined it up with my asshole, planting the tip flat against my pucker. Slowly she started to push. I could feel the outer muscle stretch wide as it tried to swallow the massive invader. I looked under me again, watching my neglected throbbing cock arch adana escort bayan a bit. The tip shiny from the pre-cum, a strand connected from the tip all the way to the bed.She pressed forward and pulled back, every forward thrust pushing a little deeper. My stretched asshole gave up and the head of the rubber cock passed the tight muscle. With one smooth gliding motion she slid the entire length into my ass until I could feel the big rubber balls pressed flat against my backside. She held it there for a moment before slowly extracting it until the big head nudged the backside of my anal muscle. Then pushed it back in to the hilt.I was completely stuffed full. My anal walls stretched to accommodate the intruder, and the feeling was fantastic! My poor rock hard cock throbbed uncontrollably, as if furious with the lack of attention. Seeing this and with a cruel streak, my wife reached down raked her nails gently over my balls, leaving my neglected cock to bob and suffer. Another drop of pre-cum spewed from the tip in protest.She started to back the rubber cock out. I could feel the bulbous head adding a bit more stretch, as if making room for the long shaft. The slick lube made it glide easily until the head bumped the back of inner sphincter muscle, then smoothly pushing in all the way in to the balls in a single deliberate motion. All the while she tickling my balls with her nails and let my cock dance for attention.She continued like this. Picking up more speed but still giving me full strokes. I started moving my hips in rhythm with her hand. Impaling my ass on the shaft to the balls then driving forward with my own rigid cock, humping into the air with no relief. She kept up the sadistic streak, now just lightly scrapping my ball sack with just two fingers, tickling them. My entire manhood was screaming for attention. Any stimulation was welcome and needed. My cock continued to throb in torture, pre-cum flowing in a slow regular stream out of the tip.She started to pick up the pace with the dildo. Sliding fully in and out. The walls of my ass no longer fought to grip the big rubber cock and just surrendered, allowing it to invade freely. I was completely in her control to do what she wanted. Completely helpless with torment and pleasure. Wanting desperately for her to grab my shaft and finish me off.With one slow gliding motion she impaled me to the base and took her hand off the rubber cock, then began patting the base with the flat of her hand. Each pat sent a little electric shockwave of pleasure through my anal walls all the way to the base of my shaft and balls. I could feel the sensation to blow start to build. With one finger, my wife began running it up and down the length of my shaft, then to the dripping head and rubbed the tip.She kept this up. Patting the base the dildo in my ass and rubbing my pre-cum around the very tip. I could feel the need to burst build. My cock no longer needed anymore stimulation. It was going blow in pure defiance of the neglect. She sensed this and pulled her finger back but kept up the patting.The first wave hit. My anal muscle clamped down on the rubber cock and my own cock throbbed violently, causing a jet of cum to shoot all the way to my chin. My wife backed away and watched.A second wave hit causing my cock to throb with more force. Shooting another jet of cum far enough to hit my cheek. I fully in the throes of orgasm. The only stimulation was the pressure of the big dildo shoved fully up my anal pipe.Another jet of come. My cocked bobbed violently, hitting my stomach and painting my chest with white sticky fluid. My hips thrashed back and forth, pumping my bobbing cock into the air and spewing jet after jet over the bed below me. All I could do was helplessly grunt and continue pumping at the empty space.After what seemed like a full minute of bobbing and thrashing, the orgasm started to subside. Looking down at my cock, I could see a long line of cum dripping from the tip to a pool on the bed. It had nothing left to give but still convulsed angrily. I could feel my anal muscles start to relax and the dildo began to slide out slowly until my sphincter caught the big round head, keeping it inside me. My wife walked up and with a gentle tug, the rubber head popped out.Completely spent, I fell forward into my own sticky mess on the bed. I could feel my breathing becoming more regular again and I started to come to my senses. My wife bent down and started to climb up from the back. I could feel the points of her nipples dragging up as she got closer to me. Her lips touched the back of my ear and in a breathy whisper said “Next time it’s my turn.”-Otherside

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