The Awakening of Kristen Ch. 08byReggaeMan©
"I think we should do it," Mark said. "Come on, you know you guys want to."
Jason looked at Kristen eagerly and nodded.
"Are you sure you want to?" she asked Jason. "I've never done that before, and I have to admit, I'm a little bit nervous. Do you think it's safe?"
"Kristen," Rachel said, "we've talked about this. You're going to love it, and it will be totally hot."
The four friends were having dinner at a local bistro. Rachel and Kristen were best friends, and Jason and Mark were quickly becoming that way. The two men shared a lot in common, not the least of which was an appreciation for beautiful women.
Jason's wife, Kristen, was stunning. Her tall, muscular body, replete with surgically enhanced breasts, belied the fact that at one time, she had been seriously overweight. Her short, spiky hair and sea-green eyes gave her a mischievous appearance. Rachel, by contrast, looked quite a lot like Jennifer Aniston. She had straight auburn hair and a killer body. As Kristen's former personal trainer, she had a lot to do with her friend's toned appearance.
Mark and Jason were both attractive men. Jason, at a little over 6'2" was very athletic, and you would never guess he was 45. Only the slightest touch of gray indicated that he wasn't 10 years younger. Mark had the lean hard body of a cyclist, which he was. He routinely put 20-30 miles on his bike a day and competed in a number of iron-man events.
The four had gotten together to talk about a topic that had been on each of their minds for quite awhile.
Kristen was the only holdout.
"Are you sure we want to try this?" she asked again. "I've heard that people sometimes feel differently afterward ... and I don't want to do anything to jeopardize our friendship."
"Jeez, Kristen," Mark said. "You'd think we were talking about having a foursome or something. It's just a sailing trip for crying out loud."
"I know," Kristen protested, "but sometimes friends spend too much time with each other, and I couldn't stand it if we stopped hanging out together."
Rachel leaned over to her beautiful friend and put her hand on her thigh. She allowed her fingers to slide up the inside of her leg, bringing Kristen's rather short skirt with it. Kristen colored slightly at the liberty her friend took with her body, but it wasn't like she hadn't done a lot more.
"Baby, this trip is only going to make our friendship stronger. Trust me."
The two men watched the women, and although they couldn't actually see Rachel's hand on the inside of Kristen's thigh, they knew it was there, and the realization gave them both hard-ons. Mark looked and Jason. Jason looked at Mark. They gave each other shit-eating grins.
They were both thinking the same thing.
"How totally fucking hot was it to have two gorgeous women who were not only into their men, but also into each other."
The group had been talking about taking a weeklong sailing trip together to the Caribbean. Mark was a master seaman, having grown up spending his summers in the Hamptons and winters in Palm Beach. His banking family owned multimillion-dollar mansions in both places. Mark, who was worth millions, came by his money the really old-fashioned way — he inherited it, or at least the first $10 million. The fact that he had increased that to $110 million in the past 20 years attested to the fact that he wasn't just a spoiled little rich kid.
The best thing about Mark, though, was that he didn't act like a multimillionaire. Sure, he wore impeccable clothing, and he did drive a nice Beamer, but he was really down to earth. At least, as down to earth as you can be when you have your own corporate jet and a 40-foot ketch.
OK, so Mark was filthy stinking rich, but Kristen and Jason didn't hold that against him. Heck, they wouldn't have minded being filthy stinking rich too.
Rachel didn't even know he had money until he agreed to put her through cooking school, just a few short weeks after they started dating. Granted, they'd spent every night of those two weeks together, but it was still an unbelievably generous offer, and it fulfilled a lifelong dream of hers. Mark had already offered to set her up with her own restaurant when she graduated, but she told him she wanted to work for someone else for awhile to really learn the ropes.
"Alright," Kristen said. "I'm in, if for no other reason than it gives me a good excuse to buy a new bikini."
"Yes!" Mark said, pumping his fist in the air. "Then it's all set. We'll take off a week from Saturday and fly to the Keys. The boat will be provisioned before we get there, so we can set sail as soon as we get our gear stowed." "I'm looking forward to the private jet," Jason said. "Hey, Kristen, maybe we can join the mile-high club," he said winking.
Kristen blushed again, and Rachel and Mark laughed. "Everybody has to do it at least once," Mark said.
"You mean you and Rachel have done it?" Kristen asked.
"Uhhh, yeaaah," Rachel replied as if Kristen had asked the dumbest question in the world. "Of course. When I found out he had his own jet, I told him he had to take me up in it so I could fuck his brains out," she laughed.
"Mark, I bet that baby has gotten you laid a lot," Jason said enviously.
Mark looked slightly uncomfortable. As a very rich, very good-looking man, he was considered one of America's most eligible bachelors, and it's safe to say that he hadn't been leading a monk's life before he met Rachel, but now that he had, he was off the market.
Rachel saw her boyfriend's discomfort at the question, and reached over into his lap to give his cock a reassuring squeeze.
"Don't worry, Baby, I know you used to be a bad boy. Why do you think I love you so much?"
Jason was feeling slightly left out.
"Hey, everybody's getting felt up around here but me," he pouted.
"Poor baby," Kristen cooed, reaching over to take his package into her hand. "Is this what you wanted?"
"Uggh, yeah," Jason said, surprised at his wife's forwardness in public in front of friends, but Kristen had definitely changed over the past few weeks. It was as if she had awoken into a new sexual reality — one that included a bisexual relationship with Rachel and a renewed willingness to try "new things" with Jason.
The group continued to discuss their upcoming trip and how great it was going to be. They settled into an easy camaraderie of friends who had been together their whole lives, yet, under the surface, there was a sexual tension that all of them felt.
Kristen licked the cum from her lips as she climbed up beside Jason and kissed him deeply. He could taste himself on her tongue, but he didn't mind. He couldn't believe that his wife had just blown him.
Sure, she's sucked his cock before, but she would never let him cum in her mouth because she didn't like the taste. She had attacked his cock as soon as they had returned from dinner, both keyed up by the aura of sex that permeated their night with Mark and Rachel.
"My God, that was incredible!" Jason said holding her tightly. "Thank you!"
Kristen giggled. "No, thank you!"
"What's gotten in to you?" he asked. "Not that I'm complaining, but you were never willing to do that before."
"I know," she said, "but I also know how much you have wanted me to, so I did it for you. I admit it's not my favorite flavor. I'd prefer piña colada," she joked.
"What? You mean you don't like penis colada?" he replied, and they both laughed.
"Jason, I love you so much, and I want us to explore every aspect of our sexuality."
"Every aspect?" he asked devilishly, caressing her toned bottom.
Kristen shuddered, knowing what was running through his mind.
Jason was fascinated with her ass and had made no secret of his desire to take her that way. They'd tried a few times, but their awkward attempts had been painful for Kristen, and she had been reluctant to try again.
She would occasionally urge him to put his finger in her ass while he ate her, but that hole was off-limits for his big thick cock.
Kristen buried her head in his chest. "Is that what you want?" she asked meekly.
"Baby, more than anything, but we don't have to do it if you don't want to."
"I'm afraid it will hurt," she said, "and ... that it will be 'messy,'" she said.
"Honey, I've been reading some information on anal sex and how to do it to minimize the pain and maximize the pleasure," Jason said.
"Where do you find that kind of information?" Kristen asked incredulously.
"Literotica.com has a whole section on "How To," and I did a little research in case ... well, just in case," he said sheepishly.
"I know that past attempts were clumsy, and I'm sorry I hurt you. Based on what I know now, though, I think I can make it so we both enjoy it ... if you're willing to try again."
Jason's heart beat wildly as he waited to hear Kristen's response. He had never fully expressed to her how important this was to him because he didn't want to pressure her into doing something she didn't want to do, but to Jason, there was nothing more exciting than anal sex.
Kristen had questioned him once about his "obsession," and he had tried to explain it to her. It was more than just the incredible feeling of being in a woman's ass. Sure there was a certain amount of excitement generated by the "forbiddenness" of the act — the shear outright naughtiness of it — but it was also the expression of trust between two lovers. And yes, he had to admit that there were slight elements of submission and dominance involved as well.
Kristen could feel Jason's heart beating quickly, and she knew that he desperately wanted her to say "yes." For Kristen, it wasn't just about the pain, although, that was a big part of her reluctance. Frankly, Jason's cock was on the large size, and her butthole was on the small size — at least when it came to taking Jason's penis inside her.
Besides the pain, though, Kristen was worried about "dirtiness." After all, that hole was used for some rather disgusting things, and Kristen was rather compulsive when it came to cleanliness.
Still, her newly awakened sexuality had led her to some amazing new sexual highs. Just a few short weeks ago, she never would have imagined herself eating another woman's pussy, and tonight she had just swallowed Jason's cum for only the second time in their relationship.
Her pussy tingled at the memory. She had to admit that it was an incredible turn on to have him quivering like putty as he unleashed his load into her mouth. She loved the feeling of control and reveled in the knowledge that she had brought him to that state. Her mouth. Her tongue. She had done it, and he had loved it. And you know what, she had enjoyed that feeling of power over him. Now, she asked herself, was she willing to give him the power over her?
"Will you be gentle?" she asked quietly.
"Yes," he said huskily, but with barely contained excitement.
"If it hurts too much ..."
"Then will stop," he said.
"OK. How do you want me?"
"Whoa," he said. "Not so fast. That's why it hurt so much the last time we tried. We — I — rushed into to, and you weren't prepared."
"OK. What does this preparation involve?"
"Come here," Jason said, and Kristen raised her face from his chest and looked into his eyes.
He kissed her tenderly at first, their lips teasing each other; their tongues lightly parting each other's lips.
"Are you sure?" he asked, desperately hoping she wouldn't back out now.
"I want to do this," she said, "for you."
She leaned in next to his ear, her voice a sexy whisper. "Baby, my ass is yours. Fuck me."
Kristen's words were so unexpected that it took Mark a couple of seconds before he fully processed them, but when he did, a big grin came over his face, and he looked into the eyes of his beautiful wife, who had just offered up her ass to him despite her fears about anal sex.
He kissed her deeply, their tongues darting in and out of each other's mouth, and his hands roamed freely over her back and buttocks. She held his head close as they kissed, her fingers playing with his hair. She could feel her husband's large organ hardening against her lightly furred mound, and she ground her pelvis against him.
"So," she said, "tell about this preparation, you mentioned."
"Well, I know that you're concerned about the 'messy' factor, so we're going to start by taking a shower to relax you and make sure you're clean back there."
"Mmm, sounds nice. Lead on, McBuff."
Jason turned toward the shower, and Kristen playfully slapped him on the ass as he walked away.
"Oooh, you're going to get it," he threatened.
Kristen turned her butt toward him and wagged it while looking over her shoulder at her sexy husband. "No, you're going to get it," she said teasing him.
"Get that sweet ass in the shower now, woman!"
The pair stepped in to the large shower, laughing and groping each other as the warm water cascaded over their naked bodies. Kristen's large breasts pressed against Jason's chest as they kissed. Her nipples hardened as the water flowed down her sloping mounds.
Jason turned her so that she faced away from him, and she felt his hardness press between the cheeks of her butt. Thinking he was preparing to enter her, she placed her hands against the shower wall and prepared herself.
Instead, though, Jason grabbed the shampoo from the shower rack and poured some of the fragrant gel into his hand. Running his hands through her hair, he massaged her scalp and Kristen groaned. Few things felt as good as a head massage.
The shampoo flowed down her back, over her buttocks and down her crack. Jason's cock now slid easily up and down that groove as he washed her hair. She pushed her buttocks back into his crotch.
He turned her around again so that she could rinse her hair. With her head tilted back to rinse, her breasts were uplifted, and he couldn't resist the temptation to take her left nipple into his mouth. The left one was his favorite. He didn't know why, but it was. It probably had something to do with being breastfed as a child.
The soap was gone from her hair, but Kristen liked what he was doing, so she stayed in that position, reveling in the attention she was receiving.
Jason disengaged, taking the fluffy and shower gel to wash her body. He started with her front, soaping and lightly scrubbing her, being careful not to be too rough with her sensitive breasts, and avoiding the delightful spot between her legs all together.
Kneeling on the shower floor, he began working his way from her feet up her legs. Kristen stretched her arms out to brace herself against the wall. Again, he avoided the juncture between her thighs, and Kristen felt a twinge of frustration.
He turned her, this time working on her back and shoulders, gradually getting closer and closer to the object of his affections. However, he skipped her butt and instead dropped to her feet and began the journey back up her legs.
When he reached the top of her thighs, he didn't stop this time, using the fluffy to lather her ass. Taking the fluffy in both hands, he squeezed it at the top of her crack, wringing the suds from the fluffy and allowing them to cascade down her ass. Standing at her side, he slid the fingers of his right hand between her cheeks. She flinched slightly as his fingers brushed across her tight butthole.
Jason leaned next to her ear, his lips brushing lightly against her earlobe.
"Relax," he said. "You can tell me to stop anytime you want to. You're in control."
She nodded her head, her eyes closed and arms still braced against the wall.
His fingers continued to probe between her buttocks, the slippery suds allowing his hand to glide across her wet skin.
Jason's index finger zeroed in on its target, lightly circling Kristen's orifice, insinuating itself into the tight opening.
Kristen willed herself to relax. She'd had Jason's finger up her ass before, but she knew this was different. She knew that soon she would have something far thicker trying to penetrate her in her most private spot.
Jason was gentle with her, not wanting to frighten her. His finger wormed its way up her back passage, the soap suds easing the way. In a little and back out, in a little farther and back out. As she accepted his digit a little deeper each time, she began to relax, and he gently rotated the finger inside her.
"We've got to get you all nice and clean, don't we?" Jason inquired.
She nodded again, not trusting her voice.
Jason continued to probe her rectum as he added his left hand to the mix by fingering her pussy. He began to masturbate her, and she felt the familiar excitement begin to build between her legs, distracting her from the mild discomfort she felt in her rear.
Jason had done his homework. He knew that by stimulating her little clit while probing her ass, he was associating pleasure with anal stimulation. All Kristen knew was that what he was doing to her felt good — really good.
He momentarily robbed her of the finger in her ass, leaving her feeling open, and she whimpered slightly at the absence. He plucked a bottle of baby oil from the shower shelf. Kristen coated her body with the oil after showering to moisturize her skin, but Jason had another use in mind for it tonight.
Popping the top, he extracted his left hand from her pussy, this time eliciting a moan of frustration from his heated wife, but it was only temporary. He squeezed a good amount of the oil into his hand and immediately began to spread it between her cheeks, paying particular attention to her anus. He squirted another pool of oil into his hand and made sure his fingers were well-coated.
Setting the bottle back on the shelf, his hands returned to their respective spots, and he went back to work pleasuring his wife.
His oil-slick finger now easily slipped up her ass, and she realized that she no longer felt any discomfort. In fact, combined with the ministrations of his left hand on her clit, she was starting to like this dual penetration.
That's when she felt a second finger begin to slip inside her butt. She momentarily tensed, and Jason halted his movement, allowing her adjust to this new sensation. Again, she willed herself to open up to him. He could see her relax, and she was surprised when the second finger joined the first, stretching her opening.
There was a slight burning sensation.
"Easy," she said, her breath hissing through her teeth, and Jason gently began easing his fingers out of her.
"No, don't stop, just go slow," she said.
With two fingers buried in her ass up to the first joints, he concentrated on her pussy, bringing her closer and closer to orgasm.
Her excitement grew, and she started to pant as her climax neared. She was completely unaware that Jason was working the two fingers in her ass deeper and deeper. He was almost up to the knuckle, knowing that if she could take his knuckles inside her, there was no reason why should couldn't take his cock. The shaft of his cock was only slightly wider than his two fingers side by side.
Kristen started to shudder and her knees went week as she started to come. Her body convulsed, and she drove her hips backward forcefully, inadvertently burying Jason's two fingers deep inside her ass. She groaned at the full invasion, but she was too far into her orgasm to care. Jason felt her rectum constrict around his fingers, threatening to crush them. He thrust them in and out gently as he continued to work her clit.
"Oh God, Oh My God!" she screamed, bucking against his hands.
The contractions finally began to subside, and Jason allowed each convulsion to push his fingers a little further out of her ass until she completely expelled him from her body.
Her once-tight butthole now gaped slightly, and she could feel the cool breeze on an area that didn't normally feel cool breezes.