Double or Nothing

All Characters are over the age of 18

Sorry about the long delay in writing a new chapter, I worked on a new series and then now I just went through divorce, but I thank my editor ScottishTexan as my editor and friend he helped me push on and now get this chapter out. The other problem I faced was deciding what to do with this series and finally got it planned. I will tell you now at max there will only be about 3-4 chapters of this story. I don't know what will come out next but it will come out eventually. Stay tuned and don't forget to leave a comment, that usually helps me keep the drive to write.

I woke up with a start. I twisted in my bed to find that I was the only one in it. My mind twisted and turned trying to determine if everything that happened yesterday was real or a dream.

It started to feel like a dream. How could my little sister and I have sexual fun and start to fall in love with each other? There was no way that was actually real, but something pulled on my heart. If that was a dream, then I was starting to fall in love with my own sister. My brain was trying to tell me what my heart wanted. My self inflicted panic was disturbed by the door to the bathroom sliding open and my sister stepped out, looking radiant as ever.

"Hey, sorry for leaving early this morning. Didn't want mom to find me topless in your bed or something." She smiled. Nope, not a dream. She walked over to the bed, sat down next to me and gave me a soft peck on the lips. "Are you okay? You look...disheveled." I shook the cobwebs out of my head before I replied.

"Yeah, for a moment there I was worried that everything yesterday was just a twisted figment of my imagination." I smiled back at her and came in for another kiss, which she gladly accepted. "Really glad that it wasn't a dream."

"Me too Mark, but I got bad news." My eyebrow raised, worried that she was going to say goodbye already or something. "I can't hold up the other part of the bet today." She pointed out the window, which I followed. The skies were grey and rain was pouring down. Almost as it was signaled, a bolt of lightning raced across the sky, followed by a rap of thunder. I looked back at Claire and scrunched my face.

"All day?" I asked.

"All day," she replied, matching my feeling of glum. A thought came to me, I snickered and she looked at me questioningly.

"You seem pretty bummed that you don't have to go swimming in your birthday suit." She started to blush a bit.

"Well I lost the bet so I wanted to get my payment out of the way as soon as possible." She tried to explain away, knowing exactly what I was going on about. I scooted closer to her, as she tried to look away.

"That's not it," I stated. "You we're looking forward to showing off in front of your big brother weren't you?" I whispered into her ear, sending a shockwave down her spine. But she quickly composed herself and turned back towards me.

"Actually I was thinking of ways to get you into your birthday suit as well." I was taken aback by her sudden burst of confidence. She pushed me to my back and laid next to me in bed. Almost like that burst was all she could muster before getting scared.

"What did you have in mind?" I replied, trying to soothe her and help her gain back that confidence.

"Well I was kind of hoping we could make another bet?" I smiled as I got what she was trying to say, playing off our "being fair" premise from yesterday.

"Well I already won a bet," I teased.

"Well how about double or nothing?" She suggested and my head went crazy thinking of what I could add onto seeing her skinny dip. I quelled any thought of something sexual as I didn't want to push things too far with her and ruin what we had already built.

"Okay lay out what you had in mind?"

"Well since this all started with skinny dipping, that would stay in our little bet, plus a little 'show' for the winner." I nodded along. " But if I win, I want you as my slave for the day..." an evil grin grew upon her face, and I snickered.

"Out of all the things you could get me to do, you choose for me to be your slave and do the chores?"

"Oh no, brother bear, as my slave you will do a lot more than that. You will entertain me, and satisfy my every need," she said in a mock sinister tone. "If I'm hungry you will feed me, if I'm thirsty you will bring me drinks, and if I'm..." she had a hard time saying the word. "...horny, you will scratch my itch." I was actually surprised by her sexual nature. I started to think a bit more about it.

"Okay sounds good but I want to add one more thing to the slave day." She looked at me, with a tinge of excitement in her eye. "The slave must be fully nude for the entire 24 hours." She looked at me like I had an ulterior motive, but she gulped unconsciously and held out her hand. I held mine out as well and we shook.

"Wait," she said. "What should we bet on?" That was a good question.

"We could use another baseball game," I suggested.

"No thanks, I don't have much confidence in my team at this point. Cost me a topless goodnight kiss." She giggled. I scoffed.

"Yeah like you didn't enjoy sleeping in the same bed as me." She smiled at me and rolled her eyes.

"How about Trivial Pursuit?"

"Ahh hell no," I replied, flashing back to our teenage years where she would trounce me every time. "I'm not falling for that trap. That's like me saying we should play a round of HORSE for the bet."

"True, true," she replied. We sat there for a moment trying to think of what would be the most fair. Then like a light bulb it came to her. "I got it!"

"Spill it," I replied.

"Hold onto your pants, or don't," she snickered. "You go get cleaned up and meet me downstairs." With that she gave me another quick peck on the lips and she was gone without letting me protest. I stretched, and finally got up and out of bed. After emptying my bladder, and washing my face and teeth I stood looking at the mirror. I tried to think and think about what Claire had in store but I trusted her to be fair. That was what all of this was right? Playing these games as a way to explore our love and sexuality in a safe but fun way. I dried up my face, got changed, and headed downstairs where my mother and sister were sitting at the breakfast bar. Our mother was applying the last of her makeup for work and Claire was eating a bowl of cereal.

"There you are sleepyhead," my mother commented as I grabbed a bowl for myself. "Now you two please don't throw any parties or kill each other while I'm gone okay?" I looked at her with pure confusion on my face, unsure what she was referring to. Our mother rolled her eyes as my sister giggled softly. "Dear I am going to be leaving for a very important conference tomorrow morning and will be gone for a few days."

"Oh yeah," I replied, feigning remembering this conference. With that our mother gathered her things, kissed us both goodbye, and was off.

After finishing our breakfast and cleaning the dishes, I went to the back door and just watched as the rain poured down. I was slightly startled as someone grabbed my hand and held it. Claire looked up to me smiling. I couldn't help but smile back.

"So what are we betting on?" I brought it back up.

"Still a surprise, but you will soon see what I have in mind." I scratched my head, still unable to figure it out. As I was thinking, I noticed something sitting out on our patio table being pelted by rain, my favorite pair of sunglasses. With that a devilish thought popped into my head.

"Claire," I started, with her pulling her gaze from the pool area back to me. "What would it take to have you strip down completely and go grab my sunglasses off the table right now?" Her jaw dropped, unsure if I was serious or not.

"Are you crazy? It is pouring buckets out there." She replied.

"Thus why it would be even better if you were naked as a jaybird." I negotiated back. She thought for a moment.

"You really want me to do it?" She asked, and I nodded. "You have to pay for lunch, no matter where I want to go, and I can order whatever I want." I was actually shocked. I expected her to want me to go streaking or something else that included me disrobing. I held out my hand and she shook it. She took in a huge breath and quickly started removing her clothes. Soon her large beautiful breasts were exposed, and then she turned away from me as she slid her jeans and panties down in unison. This was the first time I had seen her ass, which was apple shaped. But as she was bent over taking the clothing off completely, her pussy lips were on perfect display for me. I was instantly hard, seeing this beautiful sight. She quickly stood up straight and muttered to herself, "can't believe I'm doing this." And with that she slid the door open and dashed out. For a split second I thought of closing the door and locking it like the usual cliche, but the soft sound of thunder out in the distance reminded me that I didn't want to put her at risk of danger. She was quickly to the table, grabbing the item I requested and was sprinting back to me. She used one arm to cover her pussy, which also held my sunglasses, as the other arm was barely doing anything in front of her big breast as they bounced up and down. They were juggling up and down, and as hard as I could I couldn't turn reality into slow motion like the movies and she was back in the house laughing her head off.

"Did...did you get them?" Was all I could reply with. She tried to maneuver so she was still covered up but saw it as a losing battle. She kept her pussy covered as she handed me the sunglasses. Her breasts were on display for me once again. I stood there staring unable to move. She finally coughed, pulling me from my gaze. I took the glasses and shook the water off.

"Can you please get me a towel? I'm soaking wet and don't want to drag it into the house." I turned and quickly went to the downstairs bathroom and grabbed a few towels. One for her and one for the floor under her. When I returned, she was still standing there, now covered up with both arms. I had one more idea to savor this maybe 2 minute span of having her totally nude. I held out the towel with my hands and extended my arms. I walked up to her and she gave me the look of "I see where you're going with this you turd." She took in a breath and let it out, then she removed her arms and held them up high. I could now see her fully nude front side for the first time. She allowed my eyes a moment to devour her body with my eyes. Her fully shaven pussy was the first thing I stared at, then climbed up her tight tummy to her big full breast that I loved more and more every time I saw them. I walked up to her and wrapped the towel around her body. I took the chance to kiss her on the neck in appreciation. I placed the other towel under her and she started to dry off.

"Can you close your eyes now?" She asked, seemingly embarrassed to ask. I gave her a very confused look. I literally just saw every inch of her body. "It was part of the bet, now I'm a little shy, please Mark?" There was an edge in her voice saying that the adrenaline in her had worn down, and now she might be having second thoughts. I smiled at her and placed my hands over my eyes, not peeking once as she got redressed. I waited and waited, until my hands were pulled away from my eyes. There stood my fully dressed sister smiling down at me. She leaned down and gave me a huge kiss on the lips. "Thank you, let's get going."

"Where to?" I asked.

"Still a mystery, but once we are done with that you owe me a meal of my choosing" she replied.

"That I do, and it will be worth every penny I spend on it." We gathered our jackets, personal belongings and jumped into the car we shared while we were home. Claire volunteered to drive since she was the only one who knew where we were going. We pulled out of the garage into the rainstorm and we're on our way.

As we drove I tried to pry the info out of Claire but she wouldn't spill the beans. It was only when we pulled into the local mall that I finally figured out her plan. Our local mall had all the usual shops and stores, from your Macy's, to JC Penny, or your Spencer's Gifts to your FYE. The one thing we have always had as well that stood out was an indoor putt putt course. It was low budget and was adorned with black lights throughout the place to make things look less bland. But ever since we were kids the two of us would battle one another at putt putt. We never kept count, even though I had accused Claire of doing so, but neither of us was better than the other. We were evenly matched throughout the years so it made the perfect competition for this huge bet we had between us.

"Ah putt putt it is," I commented. I looked over and saw her smiling.

"Yup, it seemed perfect."

"Well I totally agree, this will be our Masters." Claire giggled as she pulled into the closest spot to a door we could find. We ran out of the rain into the mall. It was weird to imagine that I had just seen my sister do the same thing but completely nude only about a half an hour earlier. I wanted to pull her in close, but I quickly remembered that we were at a place that people who knew us could actually be. In a moment my mood somewhat changed, I realized if I wanted this relationship I had to keep it a secret to the whole world. I looked over to Claire who must not have realized the same thing as I did, as she smiled at me with that perfect smile. I smiled back at her and in that magical second, I knew it would be worth it. We were still drying off in that little area between the mall and the outside, and I looked around and saw no one. I leaned down and kissed her again, which took her off guard. Then I whispered in her ear.

"I love you Claire." I pulled back and her eyes were large. She didn't say anything back for a minute. I started to move to enter the mall but she pulled me back.

"Did you say that just to get into my head before this bet?" She asked honestly.

"I said it because my heart told my brain to relay the message to you," I smiled back. I went to enter again and she pulled back again.

"I love you too." She said softly. We kissed one more time and entered the mall finally. We walked past our favorite spots and finally made it to the putt putt place. The place was pretty much empty with one worker almost in a coma behind the counter and two kids finishing up on the last hole. We paid for our 18 holes and grabbed our very important scorecard.

The first couple of holes were an even affair. But hole 6 is where things got very interesting. The usual windmill hole, had been "updated" to be a slow moving propeller of a drone, and the mill part now looked like a downed drone. I hit my ball perfectly and was awarded with a hole in one. Claire on the other hand kept hitting the blade and suddenly had a 6 stroke lead. I could see she was discouraged but she kept chipping away at my lead that at one point was as high as 8 strokes. But then my luck started to run out as I kept leaving putts short, or the ball would swirl around the cup and come back out. On the 17th hole Claire went for it all and sank a ball after bouncing it off an iPad case that had been repurposed as an obstacle on the course. I did not do as well and now Claire was only one stroke behind going into the last hole. Claire had the better hole last so she got to go first. She lined up and tapped the ball down the hill past numerous obstacles leaving the ball about 1 foot short of the hole. Then it was my turn. I took a huge breath in, really not wanting to lose this bet, especially since I had won the other bet fair and square. I agreed to the double or nothing to get a little bit more and here we were. I lightly tapped the ball but mine had a different trajectory than Claire's as it banged off many of the obstacles, and to my horror laid rest behind a small rock that was painted to resemble Dwayne "The Rock" Johnson. My ball was about 5 feet away from the hole directly but with the rock in the way I was screwed in getting my 2 shots and would at best tie Claire. I signaled her to finish her round and she did with a curtsy. I lined up to try and bounce it off the outer wall and get it close so I didn't actually 4 putt and lose entirely. That was until Claire called over.

"Poor Mark, won't be able to see these again anytime soon," she said, as she lifted her shirt and bra, exposing her large breasts. I looked over to see no one else playing and the worker behind the desk out cold in his chair. She was being so cocky, and I loved it. Not just because her breasts were out in the open, but it showed she was very confident with her body and with me right now. But if I was gonna go down, I was going to do it spectacularly. I readjusted my aim, and was now aimed right at the rock in front of me. Claire lowered her shirt and crooked her eyes. I pulled the putter back and drove it quick and low to the ball, and the ball popped into the air, and was headed right towards the hole. I just needed it to have enough speed behind it, and it grew closer and closer to the hole until it dropped. I had won. Claire's jaw dropped as well, unable to comprehend what I had just pulled off.

I walked over and bent over, to pull the ball out of the hole. I looked around to make sure no one had joined the course and walked over to Claire and gave her a peck on the cheek.

"I guess I get to see them in all their glory a few more times," I whispered into her ear. We returned our items to the desk quietly, not wanting to wake up the worker. We entered the mall to see that it was almost empty like a ghost town. Many people were either working or not wanting to leave the house during the storm. I convinced Claire to walk around a little bit, even though she was upset by losing the bet. We window shopped here and there until we walked by a store Claire loved to shop at. She didn't stop but I pulled her arm.

"Don't you want to go in there?" I asked.

"Nah, I don't have the money and I don't know, just don't feel like it." I frowned, she was really taking this loss hard. We walked more and more until we came to a famous womens garment store for underwear and things of that nature. I saw Claire look into the store and saw a glimpse of wanting to enter the store. I took her hand and pulled her into the store. She acted like she didn't want to go inside but once inside she started to shop around. She found a few things she liked but put them back.

"What are you doing?" I asked.

"I told you, I don't have the money," she replied. I pulled her back softly, as an idea lit off in my head.

"I have a new deal for you." She looked at me questioningly.

"I'm not going streaking through the mall," she laughed. I stifled a laugh as well.

"No, goofball, grab all the things you want to try on, go try them on, and for each thing you want, send me a picture of yourself in it and I'll buy it for you." She looked at me, trying to think.

"No limit?" She finally asked. I laughed to myself.

"Keep it under check, don't forget that I'm taking you to a fancy dinner tomorrow." I revealed. Her eyes went bonkers.

"All I asked for was you to buy lunch, it doesn't have to be super expensive and fancy." She tried to explain. I put a finger on her lips to shh her.

"I know but if we are going to be together then I'm going to show you how a man should treat a girl." I smiled. She gulped subconsciously and without a word went and grabbed a few different items.

"Deal, now go find somewhere to sit and make sure it's your eyes only. I would never do this for anyone else. You're lucky I love this brand and that I love you." Before she left ear shot, I sent back.

"Love you too." I found the usual "boyfriend wait here" zone and took a seat. I was the only one there so I didn't have to keep watch on any wandering eyes. She was trusting me to this, but she must not be thinking. Why would I 1. Show her off to a stranger or 2. Share underwear/lingerie pics of my sister to someone I knew? Then I thought to myself, should I keep them? Did I have permission to keep them? If I did keep them should I hide them? My thoughts were interrupted by my phone going off, possibly with my first reward. My shaking hands reached into my pocket and pulled out my phone. I opened up the message to see my little sister in a pink frilly bra with matching panties. The message attached to the message said "4UR EYES ONLY!!" I laughed to myself and saved the picture to my memory card. I waited and waited until the phone went off again. I opened the message again to see Claire wearing a dark blue piece of lingerie. The item covered both her breast and her pussy, but was connected to each other like a one piece bathing suit, but the stomach area was cut out and in her hand was some type of frilly tail. Her breasts were almost too big for the suit as a massive amount of underboob was escaping in the opening in the front. Her message on this message,