Role Playing With My Sister and Her Daughter


For a little background to my story, I need to mention my upbringing a little for clarification. When my parents were married, my dad was a bit of a playboy. My mom knew this, but it never came in to play with their marriage until my dad messed around on her sometime between my brother's birthday and my own. We were only a year apart. So, my dad had two kids on the way at the same time with two different women. It was practically a race between my half-brother, Darryl, and myself as to who would enter the world first. Naturally, this created havoc in my parents' relationship from my birth onward. By the time I was three, they split up. My dad moved away from California to Alabama, remarried, and soon thereafter had another baby with his second wife. My half-sister, Sara, was born and raised in the southeast and I in California. Growing up, I had a few short phone talks with my half-sister, but I had never met her. Now, living in Washington thirty-five years later with the glory of the Internet, I was able to get to know my sister a little better through social networking sites. We shared photos of our families, etc. I am divorced and have a grown son and daughter just leaving my household to begin their own lives. Sara has a grown daughter, Lisa, still living at home with her. Her ex-husband, Mike, had been in the military, so they had moved around a lot as Lisa was growing up.

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  Mike went off to the war in Iraq and at some point had grown attached to a woman on the base there. He wrote home to let Sara know that he was leaving her for this woman he met while overseas. I could tell Sara had lived on the rougher side of life and was now living out the consequences.

So, as fate would have it, I found myself with an opportunity to visit my sister's hometown on a business trip to Florida. She was living in a small town near Jacksonville, so I contacted her to set up a time to meet her and Lisa in person for the first time ever. This is where my story begins.

After doing my business in Orlando, I traveled north to my sister's town to spend the weekend with her. After knocking on the door a couple times, the door opened and my eyes suddenly beheld one of the most beautiful women I had ever laid eyes on. For a moment, I thought this must be Lisa, but she invited me in and gave me a big hug and introduced herself. My sister looked nothing like her pictures on Facebook and I told her that immediately. I didn't recognize her at all. She laughed and said that she had colored her hair and bought an "upgrade," to which she proudly placed her hands under her boobs and lifted them high. I chuckled. She HAD come from the other side of the street, I thought to myself. Her hair was dyed a bright red (almost orange-red) color with dark streaks perfectly placed throughout her long waves.

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  Her eyes were gorgious, her lips were perfect, her smile was amazing, and she wore tight jeans that revealed a perfectly shaped ass. "WOW!" I thought to myself. I was guilty of checking out my sister's ass in broad daylight. But then, I had to admit to myself that she didn't exactly feel like a sister. After all, it wasn't like we grew up together. So I let myself off the hook.

She offered me something to drink and we made small talk for a while. She then asked me if I'd like to go out with her that night so she could introduce me to some of her friends. I happily said yeah and before we knew it, we were off to a party at a place not far down the road. On the way, I asked her about Lisa, and she replied that she was out with some friends but would be back before we got home later that night.

At the party, there was a lot of getting to know everyone, drinking mixed drinks and playing card games. We were having a blast. Quite a few of her friends were married and it seemed like all the women she introduced me to that gave me a rise in my jeans were there with their husbands. Nevertheless, her entire circle of friends were stunning. She was living a pretty good life, I thought to myself.


  With a bit of booze in me, I began to flirt a little with some of the women at the party, even the married ones. Sara was encouraging it at first, even helping through a few flirts, but then almost began to act jealous. I realized she wanted to have me more to herself and get to know me a little more, so I cooled it a bit and tried to visit with her more.

Eventually, the night had gone on long enough and Sara asked me if I was ready to go. With a few more drinks in me, I was feeling rather fine and had that sense of urgency that grasps you while away on a trip. I felt terrible about it, but I was suddenly more interested in having a road affair with one of my sister's friends than I was in going back to Sara's house to get to know her better. Whenever I'm on a far-away trip, I get horny for some "secret" action, similar to that saying "what happens in Vegas stays in Vegas. "I was wanting some action more than I could have realized, but then I came to my senses and realized I better just make this a "family affair. "Little did I know then that the fling I was hoping to have while traveling would soon become a "family" affair.

Back at my sister's house, we walked in the front door to discover Lisa sprawled out on the couch with the t. v. blaring. She was wrapped in a thin flannel blanket, curled up and facing the entry way, fast asleep. In that half-drunk manner of trying to be quiet while giggling our way deeper into the house, my sister shut off the t. v.

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   and then remembered that she had left her purse in the car. She went out to retrieve it. As the door shut, the sound startled Lisa enough to cause her to flip over on the couch so that she was facing the back of the sofa. In doing so, her blanket went part of the way with her, revealing a bare back and her incredibly sexy figure. She had SWEET young feet and long silky smooth legs which eventually led up to an incredibly delicious ass covered only by the thin string of her thong underwear. Once they landed on Lisa's hot ass, my eyes could not keep to themselves. Just then, I realized that the curtains behind me were slightly opened so that my sister might be able to see me watching her daughter. "Yikes!" I thought. So I withdrew myself and stood up to walk into the kitchen. Then my sister came back in. The opening and closing of the door again then caused Lisa to finish waking up and she flipped over and sat up.

"Oh. . . You must be Uncle Ray?"She said in a half-awake tone.

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  But I was too stunned to mutter anything. This sweet twenty-year-old had let her blanket drop down below her nipples, revealing her tits to the world, and I was the entire world at least for a moment. My eyes were glued to them, as if they had never seen breasts before. I shook my head a little and looked at my sister. Sara then explained, "Oh don't worry about it. She does this all the time. I swear she has the neighbor boys peeking through the windows practically every night. "As she spoke, Sara began that magical act that only women know how to do and somehow managed to unlatch her bra from under her t-shirt and pull it out through her sleeve. She then rubbed her boobs with the palms of her hands to wipe away the remaining bra friction, allowing her nipples to harden and vividly appear through her stretched white shirt. Tearing my eyes away from Lisa long enough to notice my sister, I fixated on those incredibly sexy wrinkle marks that appear in a woman's t-shirt when stretched tightly from one hard nipple to the other. She noticed me looking, but only chuckled and then waved to me to follow her. "Come on, I'll show you where you'll be crashing tonight. "

I followed her downstairs to a finished basement, decked out with an entertainment system and full wet bar. She grabbed some bedding from a nearby closet and threw it all on the big cushiony sofa. Then she flopped down and began to rattle on about how Lisa carries on, flaunting her body all over the place.

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  She said she only had herself to blame, though, raising her in the atmosphere she raised her in. This explanation eventually revealed that Sara had led a life of sex, drugs, and rock-n-roll like no other. I knew she had walked on the wild side, but it was becoming apparent that I really had no clue as to the depth of said wild side.

After a few non-detailed confessions to me, she said "So to really get to know one another better, I think a sister and brother would have to tell each other these kinds of things. Stuff like crazy sexual experiences and what not. That's when you really get to know what someone is like, and besides, that's the stuff that only siblings share with one another, right?"We were still buzzing pretty good from previous drinks at this point, and as Sara was still talking, she grazed around the wet bar and began to mix up another. She finished up with "So what is the craziest thing you've ever done?"There was a long pause in the room. "Sexually, I mean. What's the nastiest thing you've ever done?"

"Hmmm," I said. "I would have to say. . . . "I rambled on about mine and my ex-wife's adventures in fuflilling a secret fantasy of hers to be with another woman. And then about catching my sister-in-law masturbating at my father-in-laws cabin.

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  And then about my intense night with my ex-wife's best friend when we were snowed in away from our home town. (All of the stories above, I'll share in more detail in other writings later. )Nevertheless, I could tell my shared experiences were beginning to arouse my sister the more I spoke. We laughed and jeered and began to trade stories more throughout the night. She told me more detail about her ex-husband. He would be away for long periods of time and she would host intense swinger parties at her house. As Lisa was growing up, she would be put to bed and then the "fun" would begin. In addition to the parties, Sara would sometimes have one guy over, sometimes two, and a few times three or with a couple, all from the base they would be stationed at. Mike only knew of a couple guys Sara had been with, but she said he had no idea about the swinger parties. She mentioned that she quit doing it all when Mike had left her because of a few incidents that took place involving Lisa.

When Lisa was just sixteen, Sara explained that one of the guys at one of her swinger parties had managed to sneak his way into Lisa's room upstairs and coerse her into playing around with him. Lisa was curious about what she had witnessed sneaking through the house in those days while her mom would be hosting a get-together. So, naturally, Lisa gave in to her own curiosities at a young age and began to snag a guy for herself from time to time. Soon, it would become somewhat of a regular habit at these swinger parties. Sara told me that in her drugged up state, she actually began to enjoy watching some of the men, especially the well-hung ones, fuck her daughter.


  She even said that Lisa took a noticeable pleasure in knowing that her mom would watch her with a guy. . . a couple times even two men at once.

Then Sara changed the attention of conversation away from Lisa. She told me that at one of her parties, there were quite a few people present and a complete orgy broke out, so to entertain everyone beyond just the obvious sex they invented a role-playing game of sorts. They would be watching hardcore porn on the bigscreen and, during the game, they would take turns copying whatever was going on on the t. v. in real time. Whoever's turn it was would get to choose who participated in the act. Right after telling me this Sara smiled and turned on the t. v. She changed the channel to a PPV channel, typed in a passcode and bang, full-on porn was playing in front of us. I couldn't believe it, but there I was watching incredibly hot porn with my sister in her basement. Needless to say, my cock was stiffening like a flagpole in my jeans.

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Sara mixed us each one more drink, took a sip of hers, and then put it down on the end table beside the sofa as she handed mine to me. With a tug from the bottom up, she then began to peel off her shirt. "I hope you don't mind," she said, "but Lisa kinda takes after me in that I don't like wearing much of anything in the house either. Clothes are sometimes just too uncomfortable to keep on all day. "She smiled at my instant approval. "I bet you'd like to get more comfy as well?"To that I replied immediately by removing my jeans and shirt. Then I sat back on the sofa in only my Calvin Klein boxers and a mixed drink.

Focusing our attention on the screen, we watched as a woman entered the room where a workhand was fixing something in her house. She came on to him quickly and, like in most porn films, in no time had dragged him into the nearest bedroom and was zipping down his pants to reveal a monster cock. She took him in to much-appreciated moans from the lucky movie man. Sara then rose up off the sofa and knelt down in front of me. She smiled up at me as she began to tug at the top of my boxers and rub my cock through the thin material. "Want to play the game?"She asked in the most seductive voice imagineable.

I didn't even have to say anything to agree. She pulled the top of my boxers down and began to cover the head of my cock with her beautiful lips.

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  She has those sexy, puffy Angelina Jolie type of lips. I was at a complete loss for words and had no fight in me. I was turned on big time by my sister sucking my dick with plans on doing everything we were about to follow on the screen. I quickly began to focus on the t. v. set in order to expand on the excitement even more, wondering what was next in store. I knew at some point very soon, since we were following a porn movie along, I was going to have the intense pleasure of fucking my hot half-sister hard, and my cock could hardly wait for it. Then it happened, the hot t. v. porn model stood up and pushed the workman backwards on to her bed. He happily fell back and watched her turn around and lower her sexy ass down over his huge cock. She let out a huge sigh as his cock entered in to her. I felt the same warmth as my sister turned around, dropped her panties and steered my throbbing hard-on into her soaking wet pussy lips. She moaned loudly as my cock sunk deep into her. Oh, I've always loved that position, but watching my sister's arching back moving up and down over my cock was more of a major turn on than I could have ever dreamed.


  I grew harder by the second, stroke after stroke of her soft, hot pussy, up and down, out and in, out and in. This went on long enough that I was having a really difficult time holding back an intense orgasm.

Just then, in the background of the movie, a maid appeared, dusting through the house. She kept glancing at the show's two stars going at it in the adjacent bedroom. Ahh, "This could get very interesting," I thought to myself. The maid kept getting closer to the room where the fuck scene was occurring. With heavy panting and moaning blasting from the t. v. speakers, the maid finally maid her peeping eyes to the edge of the door, where she was caught watching by the woman getting stud fucked. With a wave of her hand the woman invited her maid into the room to join them. My sister looked over at the movie and stopped for a moment, pondering on the possibilities. She looked back at me and started to laugh out loud. "Hmmm," she said. "What are we going to do about this?I guess we'll have to use our imaginations a little bit, huh?"

She had barely finished her sentence, however, when Lisa inched her way around the corner. At first, thinking of the stories Sara had mentioned earlier, I thought maybe they had actually planned this night out, but I would soon learn that it was just Lisa who had become overwhelmingly curious about what her mom's plans were for the evening.

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  She was all too familiar with her mother's ways in the past, so she couldn't help but wonder if she would go so far as seducing her own half-brother. She had been watching and listening to us around the corner, and knowing what we were up to with the role-playing game and where the movie had led to, she saw the timing as a golden opportunity to add herself into the real-time portion of the game. But this scenario introduced a real-time difference. I guarantee that the maid on the television was not even related to the woman inviting her to join in on the fun, let alone her own daughter.

Lisa came in to the room wearing only the flannel blanket she had over her shoulders and extremely sexy thong underwear. She was already soaking wet from fingering herself in the stairwell. Without even saying a single word, my sister went back to fucking me. Sara was under the impression that Lisa just wanted to watch her this time, like Sara had done to Lisa so many times in the past. Then, following the film a little deeper into the plot, Sara spun around to face me and climbed back on my cock. Her tits were beautiful, perfectly round and sized just right. And they were right at my lips. My tongue grazed them as they passed by, up and down, up and down. But I had to look at the t. v. screen.

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  Were we still playing the game or was this getting to be a bit too much for Sara to consider?

On the screen, the maid had moved well into the storyline. She began to kiss the woman on the lips and rub the palms of her hands on the woman's bouncing boobs. The pumping up and down slowed and the movie turned to that slow-motion musical effect that porn films love to do. The break in the full-speed action provided the perfect moment for Lisa to move in on us. I couldn't believe it, but she must have just been too turned-on to hold herself back any longer. And Sara was feeling way too good to deny any further sinful pleasures this night might offer. Lisa began to cup her mom's breasts and slowed their bouncing. Sara looked at her daughter in very a seductive way. Suddenly there was no relationship present between these two sex-crazed women. The only thing that existed at that time was the heated passion of two women and a man who wanted to experience anything lust could bring our way. It was now about capitalizing on a forbidden pleasure that is only exciting because it's not supposed to happen. It was essence of "naughty. "

"That's it baby!Suck on mommy's titties. . .


  Suck on mommy's titties, honey. "Sara pulled Lisa in closer to her breasts. My cock grew even harder inside Sara. She moaned as she noticed the difference and as her daughter began to suck on her right nipple. This was a pleasure she had not even felt in the sluttiest moments of her past. Knowing she was about to have passionate sex with her own daughter brought on a forbidden passion she had never experienced before. She had gotten pleasure from watching her daughter fuck men in front of her, but nothing had ever been like this. And at least for the moment, she was loving it.

The guilty pleasure increased tremendously as the woman on the screen turned to the maid and began to peel her outfit off from her incredible body, revealing the most perfect set of tits I have ever seen. But that was on t. v. The realtime version found Sara peeling the blanket from her daughter's shoulders and fluffing up her tits. In perfect synchronicity, the woman on the screen and Sara both began to suck on their young maid's perfectly formed nipples. Lisa's tits grew harder as her mom's lips sucked on both of them, moving side to side as if she couldn't get enough of her daughter quickly enough. The woman on the t.

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  v. gently nudged her maid to the bed behind her, dropping her backwards on to the feather soft mattress. The workhand moved around to the back of the woman and plugged himself into the picture once again. He grabbed her ass and began pounding harder than before. The woman leaning over the bed was taking it in hard from behind from the workman, while gently grazing the inside of the legs of her now fully naked maid. She began to move up the leg of the maid, her tongue stopping to taste the sensual skin of the youth and softness of her maid's inner thighs. Oh, she could practically breathe her in. She smelled as delicious as she looked. My sister felt so good inside from behind, as I continued to fuck her hard like the handyman on the t. v. I was really enjoying this role-playing adventure. I still could hardly believe it was even happening.

Finally, the woman on the screen reached her maid's wet and wanting pussy lips. True to form, Lisa's pussy was shaved smooth like the maid on the screen. "Oh! Honey, you taste sooo good!" Sara sunk her tongue into Lisa's pussy lips and deep up her hot canal, as far as her tongue would reach.

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  Lisa was hooked. Sara was hooked. Sara began to lap away, following the queue of the woman on her maid. My cock was only a distant pleasure at this point. Sara had lost herself in the naughtiness of the beautiful young pussy in front of her. She soon lost track and strayed from the movie, staying at her daughter's clit much longer than the woman with the maid.

A good several minutes had passed with Sara licking her daughter and the film had long since moved on to the maid being pounded by the workman. But we eventually caught up in real time and continued the game. The maid then climbed on to the bed and dove down on to the woman. The man followed her and began to lick the maid's pussy from behind. The maid was in a perfect doggy position, her back arched so beautifully. Her ass was sticking out there for the taking. It was becoming more and more difficult to follow the film. I could tell we were all beginning to desire taking it in our own individual directions. The maid began diving on to the woman's pussy lips and licking all over around her hot and sexy cunt.

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  The woman was lying on her back on the bed, and the maid lifted her boss's sexy legs high into the air and then pushed her curvy feet back towards her chin. The maid then rested her arms down on the back of the woman's legs and began to thrust her tongue deeper into the woman's pussy. Following the role, this was the first taste of another woman's juices Lisa had ever tasted. And Sara was perfectly happy to allow her daughter to practice on mommy. The camera panned back to reveal the workhand behind the maid's perfect ass, his tongue going wild on her pussy lips and his nose snuggling into her hot ass cheeks. I could feel Lisa's asshole grabbing at my nose as I lapped her all over from behind. I wasn't sure where the movie was heading at this point, but I knew I wanted a taste of twenty-year-old ass badly. I moved up slightly and began to rim her hole with my tongue. She moaned in a brand new excitement. She was gaining new experiences with every breath. Tasting her mom's juices in front of her and her uncle licking her asshole from behind. This girl was having the orgasmic time of her life. Sara reached down and began to pull Lisa's head in tighter.

"Yes!Lick me you beautiful thing!Suck on my clit, baby!Mommy loves the feel of your tongue and your lips. Suck my clit, Lisa baby!"Sara was having orgasm after orgasm and didn't want it to end.

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  My tongue had loosened up Lisa's ass. She was panting and moaning through orgasms herself, one after the other. I then climbed up on to the bed and eased my cock into Lisa's hot pussy. Oh, she was so nice and tight. Sweet, sweet thing!I was about to lose my entire load of hot liquid into my niece even though I had just stuck my dick inside of her. She just felt way too good. I had to pause long and hard to keep from cumming. I held it back long enough and allowed only a few shots to sneak out. This lubed her up even more, and my cock was slimy with a small amount of cum still dripping from the end. I rested it on Lisa's asshole and rubbed back and forth a few times, lubing her up with my leaking cock juices. Once I had Lisa's ass nice and slick, I snuck my cock up her crack and wiggled it against her asshole. While still licking Sara's clit and fingering her g-spot, Lisa reached back with her left hand to spread her ass apart a little more for me. She was wanting to go the next step, regardless of the movie role. She wanted to feel my stiff cock in her now cum-softened asshole. After fingering her ass a bit for a couple minutes or so, I eased my head into her outer rim and stopped to play a little while there.


  She moaned louder. I eased in a little more. Lisa was in total ecstacy. She loved it. She began to back up on to my cock. She wanted me deeper. So, I obliged and gently, but forcefully, thrust my cock deep into her fine ass.

"OOOHH!" she screamed in delight. Pure pleasure had overtaken her senses. She rocked back and forth, asking for me harder and then harder again. Lisa began to shout at me, "Fuck me, Uncle Ray!Fuck my asshole harder. Let me feel that cock deep in my ass!Yess!Yesss!"

We all knew we were getting extremely close to the most intense orgasm any of us had ever experienced. Sara, knowing that she only had a few more moments of intense naughty fortune left, spun herself around one more time. She began to climb her way underneath her daughter, who rose up a little to allow for Sara's sexy figure to make it's way. Mom and daughter were now in a 69 position on the sofa and I was behind Lisa, still fucking her in her beautiful ass.

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  I had to pull my cock out a couple time to prolong the moment as long as humanly possible. As much as I wasn't ready to shoot my load yet, I also wanted to feel the orgasm that was about to happen more than anything else imaginable.

I decided to prolong it for a little longer and pulled out of Lisa and swung around to the other end of the sofa to watch Lisa licking her mom's pussy. I stood up and was jacking off beside the couch for a moment just so I could take it all in. Watching mother and daughter in a 69, enjoying the taste of one another, the pure passion of the forbidden nature of it all, and then the simple pleasure of how good it feels. . . It was magical. Then Lisa asked to know what it's like to be on the bottom, so the two switched places. Lisa looking up at her mother's sexy ass as she licked her from below. Lisa began pulling her mom's pussy closer to her mouth to suck on her clit. Sara did the same at the other end, pulling Lisa's ass up and towards her kissing lips.

I couldn't take just watching it any longer. I jumped behind my sister, lick my fingers and began to poke her asshole, first with one finger, then with two. Sara's asshole quickly invited my cock, and so I stuck my re-stiffened dick into her asshole.

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  I leaked a little more in the overwhelming excitement of fucking my sister in the ass and also the known fact that I was about to shoot sticky goo into my sister. What an amazing and inexplicable turn-on that was. I began pumping her ass harder and harder and we all began to pant and moan louder and louder. We were there, and we all knew it. There was no holding back and no returning to innocence. We were beyond ecstacy and into a completely different dimension of sinful pleasure. The ooohs and awwwes filled the room as liquid began to flow. Suddenly, I lost it. The delight was more than I could bear any longer. I found myself literally spewing my totally liquified cum into and then back out the rim of Sara's asshole. There was too much for her to absorb that quickly, and so it was shooting back out and running down the crack of her ass. I pulled out and finished shooting the last of my wad on Lisa's lips below.

Sara then sat up slightly and Lisa began to lick the cum from her mom's crack. Sara used her right hand to masturbate Lisa, rubbing her clit faster and faster. Lisa pulled Sara's ass down on to her mouth, Sara sitting upright a bit more, dropped on to Lisa's face.


  Sara continued to reach out and rub Lisa's clit with her middle and ring fingers. Lisa's tongue was going wild as she lapped Sara's ass crack and hole all over. Then Lisa began shouting out "I'm cumming. . . oh my god, I'm cumming!"Her tongue kept wandering around her mom's asshole and sucking in any cum she could taste left over. Sara bent her head back and moaned a loud moan. The feeling of her daughter's tongue poking into her asshole to fetch my cum was putting her far over the top. She backed up and pulled Lisa's mouth over her soaking cunt once again. Then Sara dropped her own mouth back down to fulfill the 69 position once again with her daughter. Lisa's tongue had barely even touched Sara's pussy again when she lost it. Sara both finished licking her daughter into the perfect orgasm and screamed out her own while creaming her daughter's sucking mouth. After they had both finished a long and immense orgasm together, we all snuggled together and kissed each other on the lips passionately. Hands were still wandering amok as we were winding down from an excitement that none of us had ever experienced before.

Speechless and finally back down to earth, Lisa rose up and headed towards the stairwell, announcing she was going to bed.

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  "See you in the morning, Sweety!" Sara shouted back to her. As Lisa disappeared upstairs, Sara and I soon followed her up, grabbed our toothbrushes and necessities and headed for the shower. After getting cleaned up and ready for bed together, we collapsed into her bed for the night, kissing until we fell asleep. The next morning, I woke up to Sara taking my cock deep into her steamy mouth. My sister and I spent most of that following day in bed together, and then Lisa joined us again that next night. What an amazing experience. And the funny thing was that I felt like I was on cloud nine right up until I was literally in the clouds at 30,000 feet on my way back home.

When I got back to my apartment in San Diego, I poured myself a drink and toasted to the hidden and forbidden pleasures of life, the craziness of how far we can go when we allow ourselves to travel so far from home. . . even when it's within our own mind's eye. Then I toasted to the simpler things. . . to being fixed and to my half sister and her daughter for being so incredibly beautiful.

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  . . and naughty enough to share everything with me.