The Question 6

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Readers : Please be aware that while this series of stories will get VERY dirty/kinky, some chapters will be milder than others. The specifics of each chapter will be listed in the preface so that you will know what the story contains. Constructive comments are always welcome, especially any from women as I'm always curious if I've captured anything that might remotely resemble a woman's thoughts/feelings.

This first chapter contains anal play/sex, somewhat mild D/S with a brief mention of watersports/scat play and of course, a Question! Hope you enjoy!

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CJ opened his eyes to see the spring sun streaming through the gap in the drapes and onto the bed. He recalled it was supposed to be nice today, with temperatures rising to accompany the brilliant sunshine. While they had no plans yet to take advantage of the nice day, he had a feeling that would change later... after The Question was asked. He looked over at the beautiful, sexy woman lying in bed next to him who was still sleeping - his girlfriend Lori. She faced away from him this morning, mimicking the position that she fell asleep in last night - mostly on her stomach with one leg pulled up. In fact it was the way she slept most nights they were together, so they could lock their bodies together in a modified 'spooning' position which they both enjoyed very much.

They had had sex last night, each being fully satisfied and having a wonderful orgasm - she with his fingers inside her pussy, rubbing away at her G-spot as he expertly licked her clit, making her scream in ecstasy. And he as he was plunging in and out of her tight ass as she skillfully squeezed him in exactly the right rhythm to make him explode deep within her. It was his favorite place to come, and it was her favorite way to make him come, as she thoroughly enjoyed the fullness of his cock in her ass. He had introduced her to anal sex when they first met and she took an immediate liking to it. She had been curious about anal play herself, but had never been with anyone to explore her interest. But that certainly changed when she met CJ and she discovered that she loves anal play as much as he does.

He looked over at the clock and saw that it was 8:13. A good time, he thought, not too early that they didn't get enough sleep, and not too late that half the day is already gone. Of course he had no plans on getting out of bed - it was the perfect time to begin the weekend morning ritual of waking his lover up. He smiled as he reached over and began gently rubbing her back through the tank top she was wearing. He loved how sexy she looked wearing that tight shirt, as her nipples would poke through the fabric and her breasts would gently sway back and forth as she walked. She didn't have large breasts, but her full B cups fit perfectly on her petite frame. He rubbed down her back until the tank top ended where he felt her warm skin beneath his fingers. She wore nothing else.. except socks.. always the socks. Her feet were always cold and as luck would have it, the one fetish he didn't have was a foot-fetish, so he didn't mind if she kept them covered all of the time. She was sans panties though, as she only wore them to bed when she was alone at her house. Anytime they were together he insisted on having unrestricted access to her body, to which she happily agreed.

From her lower back, his hand continued down to where her ass began as he rubbed and squeezed and massaged her soft, round cheeks. Her ass was the source of so much pleasure for both of them and he never tired of having it fill his hands. While it might not be as firm as a 20 year old's, being that they were both in their 40s, it was still a beautiful, sexy and shapely ass that would turn any mans head - and he absolutely loved it! His massaging continued, but still gentle enough that he didn't wake her just yet. He ran his hand over the curve of her hip, down to her thigh, then the back of her thigh and up over her cheek. His cock began twitching and getting hard, as he couldn't touch her for long without getting highly aroused.

With her one leg up, her ass crack naturally separated a bit, and his fingers slid down into it, glazing along the deepest part of her crevice, touching her crinkled anus and then her perineum to where it joined to her pussy lips. This was why this position was required - it gave him easy access to her entire genital area. He brought his fingers back up her crack noting that her skin felt a bit tacky around her anus. He smiled to himself as he recognized the remnants of the lubrication they has used for their anal fucking last night. They were both exhausted and save for a quick trip to the bathroom to pee, they had collapsed and spooned together before drifting off to sleep. But now this leftover lubricant would come in handy as it has in the past.

CJ brought his left hand up to his mouth and licked his fingers before bringing it back down under the sheet to her ass. His fingers went into her crack, and he began massaging her soft spongy hole, his saliva fully re-engaging the KY's lubricant properties. He knew her asshole so well he could almost count out the ridges as he slowly circled around the outside. His pointer and ring fingers were now separating her cheeks slightly to open her hole a little more for his middle finger to rub and touch. He felt his cock twitch and pulse, as if it was jealous that 'he' wasn't rubbing against her beautiful anus. But he just has to be patient, as his time will definitely come.

As his finger continued to caress her little rosebud, he slowly started dipping the tip inside, then back out and around again. He continued the massage, slowly sliding his finger in a bit deeper each time, feeing the tightness of her anal ring begin to soften and relax. Of course this was the whole point of the wake up ritual they had. He would try and see how far his finger could go up her ass before she fully awoke. Usually at the second knuckle she would begin to stir, as at that point the tip of his finger was at her second, internal sphincter which had to be slowly coaxed open to allow his finger to pass through. Being an involuntary muscle it did not respond the same as the outer one to his fingers intrusion.

CJ continued the internal and external massage as he thought about how much he loved playing with her like this. He loved that the first thing she felt in the morning was something being stuck up her ass, and he loved even more that it never ceased to excite her which usually got them started on a wonderful sex session. It was their perfect way to start a weekend day, although today would be different, due to The Question that needed to be asked.

He wanted to have a discussion with her - a sex discussion that would lead to The Question, which was something that could change the entire dynamic of their sexual relationship. But he wanted her aroused first, not to take advantage of her altered state, but to ensure she was in the right frame of mind. And there was no better way to get her excited, than to wake her up with his finger in her ass. So the massage and gentle penetration continued, the warmth of her ass enveloping his finger as it made its way deeper into her with each pass. Her outer ring was fully relaxed now, allowing his finger to glide easily inside with almost no resistance at all. Just as he reached his second knuckle and his fingertip pressed into her inner ring, he felt its natural tightening reaction which made her stir.

"Mmmmm...." she moaned in a sleepy voice, slowly turning her head and opening her eyes. "What are you doing back there you naughty boy?"

"Good morning baby... and you know exactly what I'm doing."

"Mmmmmmmm... yeah.... I guess I do" she said lazily and laid her head back down on the pillow.

With that she stretched and arched her back, which pushed has ass more towards him, which drove his finger deeper into her ass, which she knew would happen.

"Yeah... that is what you are doing..." she smiled.

"And it feels good, doesn't it?"

"Mmmmmm... yeah, it does" she replied, arching and stretching further. "You know I love when you put things inside me."

"So you love my finger inside you... inside your ass?" he smiled and questioned.

"Mmmm.. yeah, I love your finger."

"And you love my tongue up your ass?"

"Oh yeah, definitely love your tongue."

"And my cock? You really love my cock up your ass?"

"Oh god yes. I really love your cock!"

"Where?"

"Up my ass!" she said, with a smiling smirk on her face.

"Mmmmm... that's my girl..." he said smiling as his finger continued to probe around deep inside her.

He liked talking with her as they played, making her say and admit dirty, naughty things. And although they have done some of the kinkiest things together, she was still a little embarrassed about saying it out loud. But it not only turned him on to hear it, it turned her on that she was 'forced' to say it.

"You are just so damn sexy, honey...And I love it... and you." he said as he reached his head over and kissed her on the cheek.

"Mmmmm.. I love you too babe..." she replied and closed her eyes again, enjoying his internal anal massage.

He lay his head down on the pillow next to her and snuggled a bit closer. His finger was still buried in her asshole, not fucking her slowly anymore, but just rotating around gently inside her rectum, massaging all her delicate internal walls. His ring finger was now pressed into her pussy and was covered in the wetness and slickness of her juices. He loved feeling and verifying her arousal, knowing that just a finger in her ass made her pussy dripping wet.

He thought for a moment about how lucky he was to have found her. She was a remarkable lover and her openness and willingness to try anything continuously amazed him. She hadn't had any experience with kink in the past, and now they made kink - real hard kink - a permanent fixture in their intimate lives. After introducing her to anal sex with such good results, he would bring up kinkier and kinkier things to do and she would smile, say 'OK' and then be brought to an explosive orgasm during the new activity. Most of the things they did were new experiences for him too, as he had only seen them in porn or read about them. The breadth of his interests was wide as his mind was completely open to just about anything so their exploration went in many directions. He had started her off slowly at first, like making her wear sex toys out in public, such as a vibrating egg in her pussy while at a restaurant, or a butt plug during a walk in the park. They also played with bondage, domination and spanking - with her being tied up and at his mercy, 'tortured' with multiple devices for a long while before finally being allowed to release her pent up tension in an earth shattering, explosive orgasm, the likes of which she had never known before. After that he started exploring dirtier kink with her, watching her intimate bathroom activities and eventually playing with her pee and scat all the while making her feel comfortable and sexy enough to continue exploring the kinds of activities that would make most people shake their heads in disgust and revultion. But they were having a wonderful time together and were enjoying every minute of it.

All along this journey into depravity she just smiled and laughed and came, never questioning nor quashing any of his ideas. She trusted him and he always kept her safe and satisfied. Although they lived a few hours apart, they were together every weekend and as every Friday approached she would be wondering what he had in store for her; what outrageously kinky scene did he think up and plan for them in the 5 days since they had been together. He also had been sharing some of their exploits through stories and pictures on a kink website, carefully cropping out her face to remain anonymous, and she was always enjoyed reading the huge outcry of support and compliments from all over the world. Neither of them had ever been so open and intimate with another person - it truly was something special that they shared, and it went way beyond just the sex and kink. As he thought about this and smiled, he wondered how or if their situation would change after this morning; after The Question was asked. It would certainly take their relationship to a new level that he thought would be amazing. He knew it would be a big day and it started now, with his finger up her ass, stimulating and exciting both of them.

Her asshole was fully relaxed now. Even her involuntary inner ring finally succumbed to the slow gentle massaging that eased all its tension away. He was working her body now as he had so many times before. She was so sensitive in her ass that she could almost come without being touched anywhere else on her body. Now with one finger sliding between her pussy lips and another buried deep in her rectum her heartbeat raced as her excitement built. Her hips began a slow rotation as they began moving in tune to the swirling finger inside her. On every circle of her hips, she arched her back and pressed hard against him, so that his finger would delve in to its deepest point.

As she pushed back she felt the tip of his cock up against her lower ass cheek. It was hot and hard and wet as it gently stabbed into her. She lifted up her torso and shifted her position just enough to slide her right arm underneath and behind her so she could grab his cock. It throbbed and pulsed in her hand as she found the exact right spot to massage and hold him. He moaned as her fingers encircled his cock, squeezing and sliding up and down over his shaft.

"Oh. God, babe... that feels so good!" he moaned into her ear.

She smiled to herself - she loved pleasing him and feeling how excited she made him. They each thrived on knowing how they affected their lover, and that fueled their passion and excitement even more. His cock throbbed and twitched in her hand, each stroke seeming to make him bigger and harder. She knew his cock almost better than he did and was an expert at manipulating it with her hand. She alternated her strokes, first up and down running her fingers along the most sensitive underside, then all the way down and holding and squeezing tight at the base. She could imagine how wonderful his purple throbbing head looked and wished she could turn around and slide his wet cock into her warm mouth. But now wasn't the right time for that. She pulled on his cock harder, making it drip precum onto her hand, which provided perfect lubrication for it to slide deliciously between her clenching fingers. He never produced a lot of come during his orgasms, but he made up for that by continuously leaking copious amounts of precum, enough to fully wet her hand and almost as much as her own pussy produced.

They lay there together, almost spooning, touching and fondling each other and building their excitement together. Both of them were breathing heavier now, with a few moans and groans escaping from their mouths as they used all their tricks to drive the other crazy. Her hips were rotating on his fingers, both still buried within her two holes, while his hips naturally began thrusting his cock into her hand. They could seemingly keep each other on the edge of orgasm for hours, driving each other wild with pleasure. Her hand gripped him like the tightest vagina or ass that ever existed, squeezing him so that his head was purple and throbbing. His middle finger easily slid deeply in and out of her ass, which was practically sucking it in now, wanting to feel his fingertip reach the back wall of her rectum, while his ring finger was being drowned by her frothing pussy juice as it slid two knuckles deep into her vagina.

Before long they were both aching to feel his cock inside her taking the place of his fingers. CJ slowly slid them out of her holes and brought his hand up to his nose where he took a long sniff. They were slick with her juices and he inhaled deeply, moaning as he smelled her pussy and ass which made his cock twitch even more in her hand.

"Baby... look at me," he said as she turned her head to look back at him.

He brought his fingers to her nose so that she too could smell the scents from her excitement.

"Doesn't that smell wonderful? Your pussy... and your ass?" He asked, smiling at her, as she took her own deep smell of her sex.

"Yeah" she said sheepishly, knowing it was a very erotic smell but still somewhat embarrassed to say it.

CJ then separated his 'pussy' finger and aimed it at her mouth. She looked at him as she opened her mouth and took the finger inside. As her mouth closed and she began sucking off her slick pussy juice, she felt his cock throb and twitch even more in her hand. She knew he loved seeing her taste herself, especially while their eyes were locked onto each other. She swirled her tongue all around his finger tasting her sweet flavor before he removed his finger. Of course, the 'ass' finger was next as her tongue recognized the difference in flavor, adding a slight bitterness to the mix. She sucked that finger clean as well, watching him the whole time, feeling his cock engorge in her hand even more than it was.

"Mmmm.. .you're such a good girl," he said smiling at her.

With his fingers clean, he put his hand on her hip and leaning back, separating their bodies a few more inches.

"Put me inside you. I want to start in your pussy."

"Mmmmn" she moaned as her hand released his wet slippery cock and pushed him down, sliding the head down her ass crack, lightly grazing past her anus and then to her slick lips. She barely pointed him correctly when he thrust forward, knowing that the slickness and openness of her pussy would easily guide him inside.

"Ohhh... oh.. God!!!' she groaned as he was fully engulfed in her with one thrust.

"Mmmmm... babe.. God I love your pussy!" he moaned at her, as he kept his hips thrusting forward so his cock could remain fully buried within her warm, wet pussy.

He purposely stayed there, flexing his cock, making it twitch inside her, feeling her walls grip him, as she squeezed alternately to his twitches. This had taken some practice over their relationship to get the rhythm right, and when they did, it was exquisite for both of them. She pushed back on him, meeting his thrust to keep them in place with his cock buried so deep it bumped gently into her cervix. He then released his thrust, slowly backing his cock out guided by his hand on her hip. She relaxed her pussy, feeling it slowly empty before feeling him thrust into her again, filling the temporary void that was left.

"OH!!" she grunted in pleasure as his hips bottomed out smacking into her ass.

He alternated a few slow delicious thrusts with a few hard forceful thrusts, each one eliciting a squeal of delight from her. They continued enjoying their joined bodies for a short time, because although this was heaven, he knew it was time. He needed to be in her ass, and he needed to begin the discussion. This assfuck would be like no other.

"Put me in your ass" he told her as he pulled back allowing his wet throbbing cock to slide from her pussy.

She reached back and grabbed his soaking wet cock again. Her asshole was already covered with juice that had oozed out of her pussy, and combined with his precum, and a little bit of leftover KY there was no need for any additional lubrication. Her ass was completely relaxed and prepared by his finger, so she simply rubbed his head against her anus once or twice before pushing back onto him. He held steady and only moved his hips forward slightly, allowing her to gauge the speed at which he entered her ass. He loved when she was the one that put him inside - it was an extra thrill for him, seeing her impale herself, knowing that she desired his cock in her ass just as much as his cock desired to be inside her.