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A Real Gamble Ch. 01

By: crackerjack007



"Sue, I have to tell you something. I am so damn stressed out from that job that I am ready to go nuts. I don't know if I can take it any longer, so I am taking the next couple of days off." "Sweetie, why don't you spend the next couple of days with me in AC. I have a complimentary suite for a couple of nights, so why don't you and I go together."

The truth is that Sue and I have been having sex for as long as I can possibly remember. I don't really know when or why it started, but it never really bothered either of us, but it stopped cold-turkey when she got married the second time around. I was a little more than disappointed, because the sex was always available when I wanted it and it wasn't too bad, especially because I never had to wear a rubber.

Before I get further into the story, maybe I should describe Sue. She is about 5'3", 175 pounds, hazel eyes, light brown shoulder length hair, and tits that are the size of canteloupes. She isn't in perfect shape, but big girls need loving too.

We agreed that we wouldn't talk about work or anything like that while we were "away" together. We got to the casino around 8 PM and checked in. Somehow, she managed to get us a suite on the 25th floor. It was a very spacious room and had a lot of luxuries. It had two king-sized beds and a big comfy couch.

We decided to throw our stuff down and freshen up before we headed down to the gaming floor. We went down to the floor and agreed to meet up at 11pm, so that we could get some shut-eye. I headed for the tables, where I was going to spend some money, while my sister decided to spend her time play the machines. 

At 11pm, we met up and decided that it was the right idea to go back upstairs. We were going to be there for a few more days and spending all of our money on the first night wouldn't be a prudent thing to do. I actually won a decent amount of money on the tables, but I would never tell her that.

We go to the room and I tell my sister to have a drink, while I go to draw a bath for her. I went into the bathroom and filled the tub up with warm water and some bubbles that were supplied by the casino. I lit some candles that my sister had brought. Sue thought that it was nice of me to do this for her, but I knew that she needed to relax, because she was all stressed out and I had other motives.

She stayed in the tub for the longest time before coming back out. She smiled sheepishly as she admitted to me that she forgot to bring her nightwear with her into the bathroom, so she had to come back in to get some clothes. She wore a very short nightshirt-I didn't know that women in their 30s wear nightshirts, but I guess they do.

We continued talking about different things, as the TV played in the background. The conversation was pretty mundane. We were ready to fall asleep and I had a brainstorm, of sorts. 

"Sue, would you like to make an easy $25?" My sister, was very interested in this idea, especially because she likes to gamble and it would be more money for her to do such. "Sue, I am going to be pretty lonely in my bed tonight, so why don't you let your baby brother share a bed with you."

Sue thought about this for what seemed like forever. She was a little unsure, if she was willing to do this, but I assured her that it was perfectly legit and that it would be fun for the both of us. She finally relented and let me get in bed with her.

Sue's eyes widen when I got out of my bed and strolled over to her bed wearing only a pair of boxers that showed my hardening shaft get more and more solid with each step that I took. I slid under the covers with her. Sue's body was nice and warm from the bath, so I was a little more than happy to snuggle right up against her.

I hadn't had my sister's tits that close to me in a long time, and I wasn't complaining that they were that close, again. After a few minutes of lying in the bed with sis, I said, "Would you like to double your new found money?" "What do you have in mind," Sue said very softly. 

"I was thinking that it would be a lot more fun, if you were to sleep nude with me." My sister was a little uneasy with this, because she was married, and she probably remembered all of the times that I banged the hell out of her in the past. On some level, she probably wanted me inside of her pussy again, but she wasn't sure, if it would be right. 

I guess I have a way of convincing people of things that they wouldn't normally agree to. She relented to sleep in the nude with me. Sue is a big girl, but for a big girl, she has a great body. A body that needs loving, rubbing, and fucking, and it would only be appropriate, if it were coming from her baby brother.

She told me that she was getting a little cold, so she snuggled even more close to me. I could feel her tits rub against my chest, and her hairy pussy rubbing against my thighs. If she was a little bit taller, her little cunt would be getting plugged by my cock-that is how close she was to me. I wrapped my arms around her in a tight embrace, because I wanted her closer than she already was and I wanted her to feel the growth in my pants.

After embracing my sister for a few moments, I allowed my right hand to slide down to her plump ass. Sue has a big ass, but believe me, when I have given it to her up the ass, her ass consumed my cock whole and it came back spent. I slid my hand up and down her ass cheek with my finger tips, because I figured that it would send chills up her spine.

She must have liked what I was doing, because I could hear groans coming from her mouth. I rubbed the other cheek and I took my index finger and slid it down the crack of her fat ass. She started to squirm a little when I started to tickle her asshole.

"I don't know if this is right, bro," she exclaimed rather unexpectedly. "It is alright, sis, because the safest sex is sex between brothers and sisters." I let it slip out that I wanted to fuck her and that was my whole intention of getting in bed with her.

Sue gave me a look that only can be seen from a deer caught in headlights. "Sis, I am sorry." Sue replied, "No, it is just that my husband doesn't take care of my needs, any longer." "I promise to make you feel very good after I get finished with you."


I laid Sue on her back with a soft, but forceful motion. Her tits were beaming straight up in the air, as were her nipples. I got over my sister in a straddling stance. I bent down towards her tits and took her nipples inside of my warm mouth.

I sucked on her nipples, only the way, that a baby could do. I sucked and sucked her titties like crazy, hoping that I could get some milk or something out of them. "You are going to make the other one jealous, so you better start sucking on the other one," Sue said. I was happy to oblige her request, or was it a demand-I didn't really care.

After sucking on her nipples for a little while, I reached over to the nightstand next to her bed. I took my hand and grabbed a piece of ice from her cup of Diet Coke. She thought that I was going to take the ice to her tits, but I mixed her all up when I started rubbing the ice on her pussy. 

I rubbed it gently up and down on her pussy. After a few moments, you could feel that her pussy was starting to cool off from the temperature of the ice, so I took the ice in my fingers, and slid it inside of her lovebox. She probably jumped off the bed, 6 inches. I kept the ice inside of her and rubbed it all throughout her warm pussy. She later admitted to me that no one has ever done that to her before and she thoroughly enjoyed it.

After the ice had melted from her internal temperature, I pushed myself off the bed, and slid my boxers down and threw them off. I lowered myself back down onto her with my cock only a few inches from going deep inside.

I lifted Sue's legs up a little bit, so that they were around my waist. I took my rock hard cock and rubbed the outside of her pussy with it. She was starting to beg me to put it inside of her. I took my cock in my right hand and put my left hand on her shoulder. With one forceful motion, I pumped her pussy with my cock.

Sue's back arched up and her legs tightened around my back. I started to increase the speed of my thrusts into her wet pussy. I must have been pumping pretty hard, because my balls started to slap against her skin, which just gave me more motivation to pump her harder and harder.

"Sue, I am going to keep pumping your pussy, until I cum like a mad man. You are going to like it, because you love your baby brother, and you want to make him very, very happy." She continued to moan louder and louder with each thrust. It was only a few more minutes, before I could feel the explosion that was coming from my cock.

The strength of the cum must have been powerful, because my sister's back arched up and she started to relax after a few minutes. I started to pump her again, although it wasn't as hard as the last time. It only took her a few minutes of my pumping her pussy and pinching her nipples, that I could feel the muscles in her pussy squeeze my cock. She was having the "Big O" and she was loving it, because she claimed that I am the only person who can give it to her.

She decided that she wanted to be on top of me for a little while. I rolled on my back and my sister got on top of me. She faced the opposite way, so her back was towards me. She lifted herself off the bed and guided my cock inside of her pussy. She rocked back and forth, and I was able to grab her shoulders and help her with some extra motion. 

After a little while, I could feel her pussy muscles squeeze my cock, as she was exploding to her second orgasm of the night. The strength of her pussy muscles were so strong and tight that it made me cum, as well. 

She soon fell asleep and it was with a smile on her face. That is something that I haven't seen her have in a long time, and I am glad that I was able to give her the smile.

**BE SURE TO STAY TUNED FOR CHAPTER 2 IN MY STORY**

A Real Gamble Ch. 02



A few hours later, I woke up, lying next to my sister, nude. I started to grin, as I remembered all of the fun that I had last night with her. I wanted to wake her up in a way that I knew that she would enjoy.

I decided that I would wake her up with a tongue licking at her pussy. I went under the sheets and spread her legs apart. I took my left hand and opened the pussy lips apart, before burying my face into her pussy. I licked away like I was some sort of pro at this, and I have only done this once before and it was to, my mother.

I could feel her squirm around the bed, as my tongue lovingly worked her pussy. I could feel her pussy tightened as she started to cum. I went up to her and gave her a good morning kiss that was full of her sweet juices. 

"That had to be the best wake-up call that I have ever had before," Sue exclaimed. "I am glad that you liked it," is the only thing that I could manage.

I laid on my back as she arose from her sleep. She took her hand and started to rub my cock, in what started as very slow strokes, but increased to a pace faster than a NASCAR race. I didn't know how long I would be able to take it, before she just stopped all together. I was kind of pissed that she just suddenly stopped stroking me, especially because I was getting ready to finish off.

I was a lot happier when she went down and gave my rock-hard cock, a long wet kiss. She ran her tongue down the side of my shaft before landing on my sack. She licked the ball sack before lifting it up and licking the underside of my ballsack. She started stroking my cock again, as she continued to lick my balls and underneath them. After I few minutes, I came all over the place. 

Sue grabbed the sheet and wiped both of us off. She took my now-deflated cock in her mouth. She worked her mouth up and down my cock, while she took her hand and massage my balls. She would go all the way to the top of my cock, and in one swoop, have the whole cock inside of her mouth. Her face would be touching my skin. 

After I got rock hard, real good. She stopped and assumed the position. The position being doggy-style. I have always told my sister that I wanted to do a woman doggy-style, but I could find a woman who would allow me to do it.

Sue put a couple of pillows under her stomach, so that she was propped up from the bed by a couple of inches. Playfully, she took her hands and grabbed her ass cheeks pulling them apart, and said, "Fuck my ass, now."

Sue didn't have to tell me twice. I got behind Sue, and put my firm hands on her waist. I took my cock and shoved it inside of her pussy, so that my cock could be lubed without needing lube. I gave my sister a couple of good pumps in her pussy, before I took it out and rubbed it outside of her asshole.

Sue started to sway side to side, so that was my clue that I needed to get it in. I shoved my cock in her ass, very hard. I didn't want to give Sue the opportunity to re-think her offer.

I placed my hands back on her waist and pumped hard. This time, you could hear my balls slapping her ass. I decided to spice things up a little bit, by grabbing her stringy hair. Her head arched back and she screamed, "FUCK ME, YOU BASTARD. FUCK YOUR SISTER." I continued to pump her ass with my hard cock while I would occasionally pinch a nipple or rubbed her pussy.

I came inside of her pussy and kept my cock inside of her, as my cock deflated, as it was spent from all of the hard pumping that I did. After a few moments, I pulled out of her ass, and gave her a kiss before I went into the shower.

While I was in the shower, I could hear a knock at the door. I wasn't going to jump out of the shower, so I yelled for my sister to get the door. I washed up and wearing only a towel, I came back out of the bathroom with a huge smile and yelled to my sister, "I hope that you are ready to get fucked again by your baby brother, you cock loving bitch."

You can only imagine how I felt when I saw that my Mom was sitting on the bed with my sister. I was speechless...

To be continued...



A Real Gamble Ch. 03



I didn't know what to say. The only thing that I could stammer was, "Uh, uh, hi, Mom. What brings you here?"

I turned as red as a Jersey tomato, because I knew that I was pretty much screwed since my sister can't keep a secret. 

"Come here, right now, mister" demanded my mother in a rather stern, but sexy kind of a way. I wemt over to the bed to see what she had wanted. "Drop that towel, right this second and don't ask any questions."

"But, Mom, what is going on" "Did I tell you not to ask me any questions, why would you feel the need to ask me a question, young man." 

With that, mother tugged off the towel that was covering my lower body and turned me around, so that my ass was in her and my sister's face.

"Bend over that bed that you were suppose to sleep in last night, now." I obliged, because I didn't want to get into any more shit than I already had found myself to be in. The next thing that I know, mother was smacking my bare ass with her high-heeled shoe that she had been wearing. 

She smacked me about a half-dozen times and it seemed like it was getting harder and harder with each sound of heel touching skin. My mother handed the shoe to my sister, who did the same thing as mother had done, only moments ago. 

My mother demanded that I stood up and face the two of the them. I stood up, standing at full attention with my hands behind my back, rubbing by now red backside. My cock was hanging there it started to get hard, especially because it was only a couple of inches from both of mouths.

"Your sister told me what you did to her last night." (The truth is that a couple of weeks ago, mother and I had fucked like two teenagers when we went on a trip of our own).

I was a little hot under the collar about this, because I figured that not only would I never get any more "play" from my sister, but my mother would definetely cut off the fringe benefits.

"I think that there is only one way for you to redeem yourself, son."

My mother stood up and demanded that I undressed her, so that is what I did. 

First, I took my mother's white shirt out from her skirt's waistband and unbuttoned one button at a time, as I stared at her beautiful busom. Underneath, she was wearing a white lace bra that held her beautiful tits up into a perfect offering. I left her bra alone, as I slid my right hand behind her and found the zipper to her black skirt, and pulled the skirt down to see white lace panties. I undid mother's bra at this time, and pulled down her panties. 

My mother went to the bed that I was suppose to sleep in the previous night and laid down on her back with her legs spreaded way apart. She told me to help my sister up off the bed and to undress her. My sister was only wearing a white robe that the casino had provided, because we were fucking like rabbits not too long before. I took the ends of the knot that she had placed into her robe and pulled at both ends, so that the robe dropped to the floor after I slid it down a bit.

At this point, my mother's fingers had found their way to her pussy. She started to work her fingers, in and out, of her pussy. 

As if she were directing a scene in a movie, mother started to call out different action sequences to the two of her children, who were standing nude only inches apart from one another.

"Lay your sister down on the mattress, in a very soft manner." 

"Spread her legs apart." 

"Kiss her on her lips, and make sure that you use tongue."

"Suck on her tits." 

"Rub her pussy."

"Eat your sister's wet pussy. I want you to lick her thighs, first. Lick the outside of her honeybox before sticking your tongue inside."

I took the directions that my mother had been giving me, but I added some of my own things. I pinched her nipples as I ate her pussy. I licked the crack of my sister's ass, which drove her absolutely hog-wild. All the while, mother was lying on the other bed, rubbing her pussy.

After a few minutes, my sister's body started to shake like crazy. I knew that she was nearing orgasm, so I quickened the speed of my tongue. Sister grabbed my head and pushed me further into her wet snatch.

"Oh, fuck, brother. Oh, fuck, I am gonna cum, and I can't control myself. I am gonna cummmmmmmm." With that, my sister started to cum like crazy. I watched her pussy as she came, and after I was confident that she had finished cumming, I licked all of it up. After I was finished licking her pussy, I moved up to her lips and kissed her in a very loving manner, because I love my sister.

After I finished with my sister, I went over to the bed that my mother had been lying on. I started along her thighs and licked all around the outside before I ventured inside of her pot of gold. When I was about to go inside, I took my hand and stuck it on my mom's ass, as I tickled her asshole with a free finger. She was squirming all over the bed as I was doing this. 

I loved eating out my mother, because although she was older, she still had it in her. She tasted so good and she moaned like crazy as I was eating her out. 

"Sue, we have to return the favor to your brother. It is only fair, because we don't want to give him a case of blue-balls." 

My mother whispered something in Sue's ear, and the both of them started to giggle like little hyenas. I didn't know what was going to happen next.

Sue found my belt on the floor and took her belt, as well as two towels from the bathroom. Sue tied my legs to the bed, as mother tied my arms to the bed. 

The two of them started to give me a great massage. I have never had two women give me a massage before-it was one of the most incredible things that I have ever felt in my entire life. They squeezed, caressed, kissed, and licked all over my body. I started to groan in a low manner, because it felt so good and I was about to cum, just thinking about these two cock-loving bitches doing this to me.

After a few minutes, they stopped giving me a massage. They both went down towards my huge cock. Mother started kissing my shaft and licking it with her tongue, as my sister watched on. Sue followed suit and did the same thing. It was as if my mother was teaching Sue what to do.

I thought that I was going to bust a nut, right then and there, but I knew that I couldn't, so I started thinking about weird shit. My mother started to give me head-up and down, head to base in one swift motion. All the while, my sister was kissing my balls and taking them in her mouth. She rubbed my balls with her hand, as Mom continued to give me head. After a little bit, they switched places.

With age comes great things, I suppose. Mother licked the crack of my ass and played with my ass, as well as sucked on my balls and ball sack. Sister gave some really good head, as well. She stroked my cock and her head bobbed up and down, as if she was bobbing for an apple or something.

"I am going to bust a nut." After all of this, I couldn't hold off any longer. The two of these broads took my cock in their hands, and jerked me off. When I was about to cum, they pointed my cock towards their mouths. I had so much cum built up inside of me, I was able to fill both of their mouths with hot, sticky goo. They both swallowed!! I laid there with a huge grin on my face. 

The two of them stood up in front of the bed. Mother took sister's breasts in her hands and sister took mother's pussy in her hand, as the two of them gave one another a long, deep, French kiss. I started to spring a woody again, but it was back to life, as soon as they went to the other bed and started to 69 one another.

My mother was on the bottom and my sister was on top. It was a glorious sight. The two of them looked like they were having the time of their life eating one another out. I could hear the both of them moaning as they were doing this. What amazed me the most was that they both started to cum at the same time.

After they had finished, we all took a nap for a little bit. I had some pretty crazy dreams, but when I woke up, I was really ready to go again.

I woke the two of them up and told them that I wanted to fuck. I had my sister, Sue, get up on all fours. I grabbed her waist and shoved my cock deep into her pussy, as my mother got underneath and licked the underside of my balls. I pumped her pussy so hard that I thought that she was going to cry. It didn't take me all that long to cum inside of her, but I couldn't leave out mother.

I had mother assume the same position that my sister had been in. I wanted to take my mother up the ass, but I didn't have any lube, so Sue sucked on my cock to make it wet, so that it would go in smooth. I took my cock and gently put it into mother's ass. She let out a loud moan as I did this. I smacked her ass as I pumped her full of cum, as my sister was doing the same as mother had done-lying underneath licking my balls.

THERE IS NOTHING LIKE GETTING YOUR BALLS SUCKED AS YOU FUCK A CHICK!!!!! Afterwards, I fucked both of them in missionary style, as the other watched. 

I don't think we went out of the room the rest of the time that we were there. It was quite a memorable trip to say the least.