It All Started With a Dare Ch. 02

In the first chapter of the story we met Jim and Dina (a "mature" couple). Jim dared Dina to swim and then lounge in their backyard, naked. She was hesitant. He goaded her into it and they had explosive sex outside. One thing led to another and they found themselves in a nudist resort. Dina was nervous and drank too much, which led to some sexual touching in the resort pool with Walt, who along with his wife, Janine, invited Jim and Dina into the swinging lifestyle. The story picks up in Jim and Dina's room after they had sex, following Walt's touching Dina and the invitation to the couple to play together..

They were lying side-by-side, still coming down from their orgasmic high, when Dina said, "I need to sleep for a little while. I'm going to take something to try to ward off the hangover I suspect is coming. Then I want to nap."

"I'll get you some ibuprofen."

"Thanks, babe."

When he returned, she took the pills and lay back down. He said, "Before you go to sleep, Dina, are we going to meet Walt and Janine at 7:00, or not?" The question was pregnant with meaning. If they met the couple for dinner, it was the signal that they were open to having sex with them. If they were not interested, they would just order room service.

"I can't be the one who decides this, Jim. This is a big deal. WE need to decide this."

"Agreed. But YOU are about to go to sleep. What I assume will be a deep sleep. I need to know whether to wake you for a shower before going to dinner, or not."

She sat up slowly. "I told you already that what happened in the pool with Walt was very erotic. But in all our years together, I have never considered having sex with anyone else, until now. This seems too monumental for a snap decision."

"When you come right down to it, every decision is a snap decision. You can think about it for as long as you like. But at some point, the switch has to be put in the 'yes,' or 'no' position. And that happens in a snap. I just want to know what to do here, love. You know how I hate to leave things hanging. I like closure. Just tell me what your gut says."

"My gut tells me that I want to have sex with Walt." Her face and tone of voice became harsher as she continued. "And frankly, you not letting go of this thing tells me that you desperately want to have sex with Janine." Then her tone softened. "But, I really am frightened about what it could do to our relationship. You said yourself that you were feeling jealous when you thought you saw Walt touching me."

"A couple of things and then I promise, I'll let it go, and let you sleep." She nodded. "First, if the opportunity is presented, yes, I will have sex with Janine. And I bet that I will really enjoy it. But I am definitely not 'desperate' to do so. If I was looking for a sex partner here, she would not be at the top of my list. It is the eroticism of seeing another man interacting with you sexually that has me all keyed up. And second, there are no guarantees about how either of us would really react in this new situation. But know this, my anger completely dissipated when I saw how excited you were. And besides, you are here with me, and that's where you will end up, no matter who else you might have sex with."

As if he had not said anything, she said, "I need to pee and get the last of your cum out of me, so it doesn't continue to leak out while I nap." She jumped up and headed for the bathroom.

When the door closed, he heard her stream start and he noticed that his hands were trembling. He had no idea how she was ultimately going to respond, but he was excitedly anticipating something brand new. And at their ages, how many brand new things came along? He had to admit that he really did want this. Not just to have sex with the voluptuous Janine, but more because he wanted to watch Dina have sex with Walt. His whole body felt like a coiled spring, and he was getting another erection, just considering it.

Dina came back and plopped down on the bed. She looked at him and said, "I was sitting in there thinking about what tonight might be like. I kept wiping away your cum and then there would be more to wipe. Then I reached down barehanded and it dawned on me. That was not your fluid I was wiping away, it was mine. I am all wet and tingly again. And my heart is going ninety miles per hour. So... I think we should go to the dining room at 7:00."

+++++++

They were both as nervous as they'd ever been while they prepared for dinner. Dina had napped fitfully. And although her head was a bit tender from the alcohol, she didn't feel any horrible effects from the afternoon's activities.

Dina had finished her hair and was starting her make-up. Jim was pacing around the room naked, with a hard on bobbing in front of him. Since they were going to the main dining room they had to be dressed, at least by resort standards, and on top of being excited, Jim was not looking forward to putting on clothes again.

"It's about ten to seven, are you nearly ready?" He walked into the bathroom where she was finishing her make-up.

Dina laughed when she saw his penis bobbing around. "I have never seen you like this," she giggled. "You are like the proverbial cat on a hot tin roof - only with a hard-on."

"Oh, yeah," he replied, "and you're just the picture of cool, calm demeanor."

"I have to admit that I've been having trouble sitting still in here. And doing my eyes with shaky hands has been a challenge. Do you really think we're doing the right thing?"

"Right?" He huffed. "What's right? I just know that we're about to have a brand new sexual adventure. And I'm excited about it."

"Well then," she sighed, "let's finish getting ready and get to the dining room. Put your clothes on. What are you going to do with that thing?" She grinned, pointing at his penis.

He laughed and said, "Do you think this is the first time I've had to tuck a hard-on into my pants? Back when we met my dick was hard for hours every day."

He slid on a pair of golf shorts and wrestled his penis into an acceptable position. Then he pulled on a golf shirt and sandals and he was dressed. Dina said, "Is that the best you can do to hide your penis? Maybe you need to wear a longer shirt." She was still laughing at him as she reached into a drawer and pulled out a pair of panties.

"Oh no," Jim cautioned. "You have to go commando tonight, just like me."

"If I don't wear panties, there is going to be a wet spot on the back of my dress when I sit down."

"Yeah well, if I get any more excited, I'm going to leave a wet spot on the front of my shorts as well. But I'm not wearing underwear and neither should you. I'm not even happy about wearing any clothes."

She wrapped herself in a semi-sheer sarong type dress. You couldn't exactly see through it, but if you tried you could definitely make out her nipples and a dark spot at her crotch.

Jim whistled long and low. "You look amazing. Let's go."

++++++

They sat with Walt and Janine, as planned. They shared a bottle of wine with dinner and the "hair of the dog," made Dina feel much better.

Janine dominated the conversation. She was clearly the member of the couple who was in charge. After the small talk about family and jobs, the conversation turned quickly to sex.

"Walt and I are really looking forward to playing with you two. Dina, Walt raved about your ass. He is an ass-man from way back. I took a look, and I have to agree with him that you have a great one. I promise you that at least once tonight, he's going to want to do the doggie with you. And Jim," she reached over, under the table, and squeezed his crotch, I cannot wait to get this thing in me. Now, let's talk about do's and don'ts."

They spent the rest of the meal talking about sexual likes and dislikes, in normal voices, not even speaking softer when the waiter came by. Both Jim and Dina were astounded. They had rarely had conversations like this with each other, much less with complete strangers. But they were both very excited by the talk. Over the course of the conversation, Janine had shared recent blood test results, indicating that neither she nor Walt had any STDs.

"I'm sorry, Janine. But we have not been tested for anything, ever," Jim told her.

Both Janine and Walt laughed. "We're not worried about you two. We sincerely believe that neither of you has had sex with anyone else for decades. So, in our world, you're not only virgins, you're the cleanest of the clean virgins. If you're okay not using condoms, we definitely are." With that, all the details were set.

Once they had left the lobby area, they all stopped in the hallway and took their clothing off. They walked into Janine and Walt's room. It was a double room, unlike Jim and Dina's king room. Instantly the room difference made sense to Jim. Each couple would have their own bed, cutting out the possibility of bumping into each other.

Almost before the door to the room was closed, Walt had Dina in his arms. He had dumped his clothes by the door and grabbed her, pulling her in tight. He kissed her deeply and cupped her ass cheeks with both hands. She pulled back and said, "Hold on, Walt. I need to move a little slower than this. Can we kiss a little more gently, and take some time?"

Walt smiled his most charming smile. "I apologize. You excite me and I let that excitement get the best of me. We will do this the way you want." He stepped back toward her and opened his arms. She tentatively stepped into his embrace and shivered as she felt his long, substantial dick against her belly. They kissed, softly at first, but soon growing more passionate.

Janine knelt in front of Jim. She took his cock in her hand and licked it from bottom to top. Jim shivered slightly but never took his eyes off his wife. "I can tell you want to watch them, Sugar. So for now, just let me do the work. She took him in her mouth and began to do things to him that he had never felt before. He looked down at her and watched his cock completely disappear in her mouth. He moaned and grabbed two of her long braids in his hands.

"Uh uh, Sugar," she said when she took her mouth off his cock. "Don't ever touch a black woman's hair without specific permission. Feel free to fuck my throat when it's in there. It has to be hands free, unless you cup my cheeks in your hands. But for now, just watch and enjoy." With that, she swallowed his cock again. But this time, she held his balls in one hand grabbed his ass cheek with the other.

Walt had one of Dina's breasts in his hand. He was tweaking her nipple and squeezing the soft flesh. His other hand was on her pussy. He was exploring her inner folds and stroking alongside her clit. Dina began to moan. She had Walt's cock in her hand and was stroking it slowly. His hips began to move with her strokes, just as her hips were bucking against his hand. He slipped a finger into her burning hot pussy and a trail of her lubricant squeezed out and down his palm. He spread it all around and began to finger fuck her while he pressed on her clitoris with his palm.

Dina knew that she was not going to last long. The situation was just too erotic. She broke their kiss and said, breathlessly, "Please keep doing that. I'm almost there." He did. And she orgasmed. She threw her head back and groaned loudly as her body started to shake. Her knees almost buckled from the intensity of her orgasm and the near-epileptic shaking.

When Dina orgasmed, so did Jim. He had never seen anything as sexy as this. He grunted hard as he shot rope after rope of semen. Janine pulled off him as his orgasm started and stroked his shaft, aiming the cum into her mouth. He gave her a mouthful before his orgasm ended. She stood up and showed him his work.

Jim was completely shocked when Janine kissed him and shared his cum with him. He recoiled, but she held tight, shoving her tongue and his cum into his mouth. He relaxed and kissed her back. When he was a teenager, he had often masturbated and licked his cum off his hand if he didn't have anything handy to clean up with. But this was next level stuff. He and Janine shared their sloppy kiss for several minutes, while his hands pulled on her incredible nipples. She moaned into his mouth.

Janine broke their kiss and said, "My turn, Sugar. One good turn deserves another." She lay back on the bed and opened her legs. "Have you ever eaten a black woman's pussy?"

"No," Jim said as he knelt next to the bed. "Is there something different about it that I should know? Like, don't touch your pubic hair?" He grinned up at her and she laughed heartily.

"No. Feel free to touch anything you want while you're down there. But rather than have you hunt around for things I might like, I'll just tell you. I like to have my clit licked with the flat of your tongue. Press down pretty hard. I want two or three fingers in my pussy. And when my juice is flowing real well, use some of it to lube up my ass and put a finger in there as well. When I really get going, you'll be moving fast. So pace yourself."

Jim shook his head in wonder. He had never met a woman like Janine before. He went to work on her pussy, trying to remember all the jobs she had given him to do. Soon, as she had predicted, Janine's pussy was flowing with juice. She smelled and tasted very different from Dina. Not better or worse. Just very different. He enjoyed her. And he loved how unbridled her responses were. She had her tits in her hands and was pulling and twisting her nipples roughly. She was bucking against his face and hands. And she was talking to him non-stop.

"Oh shit, Jim! That's it! Lick my pussy! Fuck me with those fingers. Harder. Deeper. Get that finger deeper in my ass! That's what I like! Make me cum, Sugar. Make me cum!

When she finally orgasmed, it was a show. She squirted harder and farther than Jim would have thought possible. It was like a fountain coming out of her. He literally drank from her. Her pussy spasmed so hard around his fingers that he feared for their safety. When she was finally finished with her full-body cum, she relaxed back onto the bed. Jim struggled to stand and then turned at the sound from behind him.

Walt had Dina on her knees on the bed. He was buried in her pussy and was fucking her as if there would be no tomorrow. Like Janine, he too liked to talk.

"Dina, you have some wonderful pussy! I love it! I'm going to fuck you like no one ever has."

Dina was moaning non-stop. And with every hard stroke, a little grunt escaped her. Her eyes were closed and she had a look of deep concentration on her face. Her fingers were busy on her clit and Jim knew from experience that she was about to orgasm again.

She came with a deep series of grunts. And that triggered Walt. "Oh yeah! I'm cumming! Fuck my dick, Dina! I'm going to fill your cunt with my cum!"

Even in the midst of her orgasm, Jim saw Dina flinch slightly when Walt called it her cunt. But she clearly had a wonderful orgasm. As Walt fell off her onto his back, she went face first into the bed.

Jim sat on the bed next to Janine. Now that Dina was resting, he turned his full attention to Janine, who was slowly, languidly masturbating. Here eyes were closed and she was moaning softly. Jim shifted around and leaned down to take one of her giant nipples in his mouth. Her eyes fluttered open and she smiled at him.

"Welcome back, Sugar. You ready for some serious fucking? I'm definitely ready to get that big dick deep inside me. Come over here."

She got on her knees and put her head on the mattress. She reached behind her and spread herself lewdly. "Come on, baby. Get up in here."

Even though he had just spent an extended time with his face buried in this pussy, he still paused to gaze at it from a different angle. Janine looked back at him over her shoulder. "What are you waiting for? Start fucking me. I want it right now!"

"Yes, ma'am!" He chuckled. He moved behind her and pushed his cock into her slowly, not wanted to cause her any discomfort. But she pushed back against him almost hard enough to knock him off balance. He grabbed her glorious ass to stay in position. She leaned forward and then slammed back against him again. The message was clear! Jim moved her hips slightly, to get better leverage, and then started ramming his cock into her ferociously.

"That's the way, baby! Fuck that hungry pussy! Give me that dick! Give it to me good! Hit that pussy hard! Make it yours!" With every hard stroke, Janine's pussy was expelling air in a series of 'pussy farts' that she seemed to be enjoying greatly. "Yes, make it talk to you! Fuck yes! Don't you stop! Don't you fucking stop! Right there! Right there! I'm gonna cum!"

With her last shout, she orgasmed. This time, instead of squirting, liquid gushed out of her, soaking the sheet beneath her, and Jim's thighs. She bucked and cursed and shook her way through it until he had to take a break from all the exertion.

She purred, "That was some good fucking, Jim sugar. I thoroughly enjoyed that. Now there's only one more thing you need to do. I'm glad you managed not to cum just now. Because I'm really in the mood to get my ass reamed. You want to fuck my ass?"

Although Jim wasn't sure how much energy he could muster, his cock was still hard and he really did want to put it in her big, beautiful ass. So they both got back into position and she handed him a bottle of anal lube from the nightstand. "Lube everything up good, Sugar. Your dick is big enough that we need to be careful. But don't let that scare you. Lots of lube and then fuck me hard, like you just fucked my pussy. But go slower with my ass. I like it hard, but slow."

Jim had never heard anyone talk as much during sex as Janine did. Even in porn he had never heard anything like it. He chuckled at her as he was working the lube into her back door. Then he noticed that Dina and Walt had come back to life. They were lying on their sides, in the spoon position, watching him prepare Janine's ass. Walt whispered something in Dina's ear. She seemed to consider it for a minute and then nodded.

"Toss that lube over her please, Jim. We're about to see what we can accomplish in this comfortable position." Jim's eyebrows raised at the request. He tossed the lube across to the other bed and put his cock at Janine's asshole. He pushed forward and the head popped right in. He pushed a little harder and was soon buried in her.

As he started to long stroke her, putting a little extra 'umph,' into each stroke as he bottomed out (pun intended), he looked at his wife, whose ass was at that moment being very effectively fingered.

"I thought one of your 'don'ts' was anal?"

"It was. But I changed my mind. He promises to be gentle. And what you're doing looks like fun."

Jim said, "Would you raise your top leg when he puts it in? I want to watch him fuck you."

Dina's face colored red, but she nodded. She was now feeling some lovely feelings that she really wanted to concentrate on. So she didn't feel like talking. Jim was fucking Janine in a slow steady rhythm. Instead of shouting, as she had before, she was just loudly moaning and grunting. Her fingers were working on her clit.

Dina raised her top leg when she felt Walt's head at her anus. Jim sped up some and fucked Janine a little harder as he watched another man's cock slide into a place that his wife had only allowed him to enter a few times. He felt a little jealousy, but mostly he was excited and just wanted to watch.

He saw Walt's long cock go into his wife's ass up to the hilt. Then he watched it come sliding back out, only to disappear again. After a minute or so, Dina moaned and said, "This feels amazing, Walt. Please go a little faster." Walt immediately increased his pace. That made Jim increase his speed as well.

Janine said, "Are you getting ready to fill my ass with cum, Sugar? Or is watching your sweet wife taking it in the ass causing you to speed up?"

"Yes!" was the only word that escaped Jim's mouth. Both things were true, in equal measure. He could feel his orgasm building. And he couldn't take his eyes off Dina and Walt.

Dina said, "I'm getting a leg cramp, Walt. Let me get on my knees."

They switched positions and Jim was treated again to the sight of another man's cock sliding into his wife. Now Walt really picked up speed. "Tell me if it's too much, Dina."

"No!" Dina snapped. "That's wonderful. Use some more lube and do it really hard. Yes! Just like that!"

Jim couldn't stand anymore and his orgasm overwhelmed him. He stared at his wife as he grunted his way through filling another woman's ass with his cum. He gripped Janine's hips, trying to keep his softening cock inside her. But it slipped out with an audible plop, just as Dina came.

Her whole body seized up and she couldn't move a muscle. It was like the orgasm had locked her up. But the amazing sensations in her anus and pussy washed over her repeatedly, wave after intense wave.

"Shit!" Walt yelled. "She's gonna cut off my cock!" He had to rip his cock out of her, mid-orgasm, because she was squeezing him so tightly. He stroked his cock several times and then spewed cum all over Dina's beautiful round ass.

They all collapsed and laid there, stunned into silence. Janine naturally was the first to speak. "Well, I guess there's not an orgasm for momma this round." Her tone was huffy, but she was smiling.

After a few minutes, Dina finally spoke. "Jim, I think we should go back to our room. I have had about all the 'play' that I can stand for one night. In fact, I'm not even sure I can walk back to our room. Both of my holes are pretty tender, and my legs have little left in them."

Janine sat up and pulled Jim to her. She kissed him gently and said, "You did a wonderful job tonight. I've been fucked by a lot of guys half your age who couldn't do what you did. Thank you. I'd love to fuck you again, any time you'd like."

Walt helped Dina gingerly get out of the bed. He kissed her cheek and said, quietly, almost in a whisper, "I loved every minute of this. I hope you did too. No matter what... believe that you are an incredibly sexy woman. And know this... I've had sex with over 75 women. Not one of them was a better sex partner than you. You would be in a tie with some of them, my lovely wife included in that small group, but I have NEVER enjoyed sex with someone more than I enjoyed this."

Jim and Dina thanked them both and gathered their clothes and walked slowly back to their room. Jim drew a cool bath and Dina sank into it. He called room service and had them bring ice and a plastic bag. When it arrived, he made his wife an ice pack. She got out of the bath and into bed. He helped her find a comfortable position and wrapped the ice pack in a towel. She slid it between her legs and sighed as the cool relieved her discomfort.

"I'm sorry if this turned out to be too much, Dina."

"Please don't apologize, my love. I absolutely enjoyed every single minute of tonight. It's just that my... pussy... and my... ass... have no experience with this amount of action. And they are reminding me of that fact. I bet that tomorrow I will feel much better. Thank you for pushing me to do this. The nudity, the sex, the whole thing. Even with all the discomfort, I still feel some excitement. I feel much younger than I have in decades."

Jim slid into bed next to her and said, "Can you lie on your side and still keep the ice where it needs to be? I'd really like to cuddle for a while."

He molded his body to hers and put his arm across her, just under her breasts, holding her close enough to be able to feel her heartbeat. In that moment, they felt like two who were one. "Dina, I know that you were worried about what would happen with us if we had sex with Walt and Janine. I just want you to know that I have never loved you more than I love you right now. You are the best thing that ever happened to me, and I adore you." He lightly kissed her neck.

Dina snuggled back into him, removing what little space existed between them. She squeezed the arm that was draped across her. She felt safe, secure, and loved. "I love you so much, Jim. You are a wonderful husband and lover. And even if we try something like this again, no one else will ever -- or could ever -- take your place in my life, or in my heart. And by the way..."

"Yeah?"

"Thanks for daring me to go naked."