Cyndi And Friends Ch 03 Hiking

Kate's Story

"Hi there!" I said as Cyndi appeared from downstairs. "Get enough sleep?" It was nearly 10 AM, and I was setting out dishes while Jacob whipped up some pancakes. She walked over, wrapped her arms around me and kissed me. Her lips were warm and soft.

"Good morning my loves!" she said. "I hope you feel as good this morning as I do!"

"I guess you needed that more than we realized," Jacob said from his place at the griddle.

"I needed it more than

I

realized," she answered. She was wearing her skimpy outfit from last night, but  with the sun streaming through the kitchen windows, on an unseasonably warm day, her nipples were at parade rest. Marginally less distracting than last night.

"Sorry again about not telling you what was happening. We should have asked you at the start." I remembered how upset Cyndi had been when she thought Jacob had cheated on me with her.

"Water under the bridge. What do you want to do today?" she asked.

"That wasn't water," Jacob muttered under his breath.

"Let's go for a hike," I answered. "Have we told you about the Red Rise Trail?"

"I don't think so."

"That's the plan then. It's a great hike, and we've never seen more than two or three other people on it," I said.

"Sounds great," she replied. "How long is it?"

"About five miles."

"Is that too long for flip-flops?"

I gave her the side-eye "Seriously? Yes, you'll want real shoes."

"Shoot. Can we stop by my house and get my hiking boots on the way? Maybe some better shorts too. These aren't really appropriate." She gestured to the tiny satin pajama shorts. The top wasn't ideal for hiking either, barely covering her boobs. And she was going to want a bra.

"These are fine with me, if I get to walk behind you," Jacob said. I snorted, although the thought of her parading around looking like that was making me tingle. But she was right. Also, was that really all the clothing she had with her?

"Didn't you bring anything else to wear?" I asked.

"Just the jeans I had on. And they're too tight for hiking."

"That's all you brought for the whole weekend?"

"You said it was a slumber party!"

"Did you even bring a bra?"

"I was in a hurry," she explained. I rolled my eyes.

"Fine, we can stop by your place," I said. "Pick up whatever you need for the rest of the weekend." Sometimes I wondered how she remembered to eat.

"Cakes up!" Jacob announced. We sat down for breakfast.

"So, everything's still good?" I asked around a mouthful of flapjacks. "You're not feeling weird about sleeping with your friends?"

"Feels surprisingly... normal?" she replied. "How about you guys? I know it's weirder for you, Kate. You still sure you're not a lesbian?"

I laughed. "Considering what Jacob and I did last thing before sleep, I guess not. Besides, I didn't even taste your bread pudding."

She laughed. "So, not 100% sure yet?"

"Well I guess I can't know for certain until we, uh..."

"Until you lick my pussy?" she finished helpfully.

"Yes," I replied. "Until I lick your pussy. And make you come," I added for good measure. I was determined to get over the not-a-lesbian-dammit phase I didn't know I was in until last night.

She smiled and jiggled her chest at me.

"Well I wasn't planning to have a hard-on for breakfast," Jacob chimed in. "But here we are."

"Ooh, that sounds delicious!" Cyndi exclaimed, before bringing us back to Earth. "We do need to talk about where this is going, though. Last night was amazing," she continued. "But we need a clear set of rules. What we each want, what we don't want. I promise you it's better to do that now."

"Of course," Jacob answered proudly. "We already made a set of rules."

"They might have been slightly under-thought," I added.

"Oh? What did you come up with?" she asked.

We showed her the list we had made before inviting her over:

1. No Penis-In-Vagina sex

2. Jacob makes the first move

3. After that, let Cyndi lead

4. No watching or joining in (unless overridden by rule #3)

"Oh, that's so sweet!" she said. "Thank you for letting me lead. It would have been better to let me know the plan up front though." She narrowed her eyes.

My heart twisted in my chest. "I know!" I blurted. "I'm so sorry!"

"Apology long since accepted," she said, laughing. "Consider it a learning experience. But, you did pretty well overall. Writing it down is a great idea. It does need some, uh, fleshing out." She grinned.

I rolled my eyes. "Like what?"

"Well for instance, according to the list, anal is okay. Is that what you intended?"

We both burst into laughter. "That's exactly what J said," I explained.

"Okay, that's funny," she admitted, "And...?"

"The rules say it's okay," I responded.

She raised an eyebrow. "Are you sure? Would you really be okay with Jacob fucking my ass?"

"Would

you

?" I asked.

"That's not the question," she replied. "I need to be sure you've thought about the consequences of your rules. You should ask yourself why you're okay with him fucking my ass but not my pussy," she said.

"Um, well we haven't ever done anal," I said. "So it feels like it doesn't count as sex? And it's more about lust than intimacy anyway."

"Don't be too sure. Think about this: He would only be getting ass from me, while he gets pussy from you all the time. I'd be giving him something you don't. Is that a situation you want? I'm not saying it's wrong! But you should think it through. You can learn a lot by asking why you feel the way you do. What are your no-nos, your kinks, and so on."

"I guess I hadn't thought so far upstream."

"No hurry answering, just something to consider. So, you've never had anal sex?"

"We've played around with fingers there, but only a little. I want to do more, but I've been too nervous to try," I answered.

"Do you enjoy the fingering you've done?"

"Yes!" we answered in unison.

"Okay. Jacob, are you interested in exploring it further?"

"Me? Yeah, I am. But I don't want to pressure Kate," he said

"How about as the recipient?" she asked. "Do you think you would like that?"

"Wow, who's the professional sex counselor now?" I said.

"Not a professional. But I've taken some courses."

"Really?" I asked. Why had she never told me? Although... "Maybe that's good considering the... unexpected feelings I had... have."

"Yeah, I'm hoping I can be helpful," Cyndi said with a smile. "But we were talking about Jacob. So. Are you interested in receiving anal?"

"Oh, uh, I might. I like it when she touches me there. I've never thought about having a... something larger."

"Like a cock or a toy. You can use the words. And try to say 'asshole', not 'there'. Don't think of it as dirty if you want to have fun." Yeah, her training was going to be helpful. And she was clearly more experienced than I knew. "So, you both want to try it, but haven't done anything more than fingers. Do you have any toys? Butt plugs or dildos? Lube?"

We looked at each other. "No, nothing like that," I said. "Not even really fingers, at least not all the way in."

"Hmm."

"Hmm what?" Jacob asked.

She paused. "I was thinking about how to thank you for helping me with my problem. Maybe this could be a way."

"Your problem being no boyfriend?"

"My problem being no boyfriend," she agreed. "Or girlfriend. I mean, no

sex

is the... was the problem. I can live without a boyfriend. Or a girlfriend. But I've lost interest in one-nighters, so all I've had is my toys. I need some kind of connection, and it just wasn't happening. Until last night. I really... Thank you both. So I want to do something for you."

"What are you thinking?" I asked.

"I could teach you about anal sex. I know plenty, and seems like you could use some instruction."

"How much is there to teach?"

"Well, it depends on whether you want it to hurt or feel good." She grinned.

I rolled my eyes. "I mean, does it take a lot of training? Do you do it often? Do you like it? What do we have to know?"

"Okay," she said. "I guess you're interested. Yes, I do it, maybe not 'often', but... Well, not at all recently, but a lot in the past. Like I said, when it's good it's amazing, but when it's bad it's unpleasant. Or painful, if it's really bad. And most guys don't know how to do it well. Or maybe I picked a lot of wrong guys. Anyways, I'd pretty much given it up. I haven't done it with a guy in like five years."

"With a woman though?" Jacob asked.

She smiled. "Yes, I've had anal sex with women more recently. Women care more about doing it right. Probably because they're not concentrating on their own pleasure. Maybe men just aren't meant to fuck women in the ass."

"Hey!" Jacob said. "Hashtag-not-all-men. I mean, I hope."

"Well... that was my hope, too. And I have had good anal sex with guys. Well, one guy. Anyways, if you want to, I can teach you both how to do it right. Would you like that? I promise it'll blow your mind."

Jacob and I looked at each other. I knew I wanted to try, but I didn't want to suggest something he wasn't up for. "What do you think, sweetie?" I asked. "Would you like--"

"Yes."

Cyndi and I laughed. "Okay, we're going to do it right," she beamed.

"So what does teaching us entail?" I asked. "Do you have like, sex ed movies for us to watch?"

"No movies, just me. I can tell you what feels good and what doesn't, and give you some tips."

"More than just the tip, I hope," said Jacob.

"Hush!" we both answered in unison.

"If you do well on your quiz, you'll get to use the whole shaft," Cyndi said with a grin.

Jacob shifted in his chair. "Oh, there's a quiz? Like, a practical quiz?"

Cyndi looked uncomfortable. "I'm rushing you again aren't I? I'm sorry, no, of course we can just... I can just give you some tips."

"No, it's okay," I said. I took a breath. "What

did

you mean by quiz?"

She paused. "Okay. I was thinking we... I show him how with my body. So I can make sure he's doing it right." Another pause. "Now it just sounds like I want him in my ass."

"You do, don't you?" I smiled. Still, the thought of watching his cock slide into Cyndi's ass made it less intimidating. Also it was making me wet. Okay, that's new. "Y'know what? That actually sounds like... yeah. I'm down with it if Jacob is. What do you think, J?" It was obvious from the look on his face that he approved as well.

"Okay, I'll pick up some supplies when we stop by my place," she said, with a combination of relief and excitement.

"Oh! You mean this weekend!" I said. I was surprised at how fast this was happening, and shocked at how excited I was getting.

"Unless you'd rather wait. No rush." The thought of Jacob's cock in her ass, and then mine, was tugging at my clit-strings.

I looked at Jacob. "Yeah, okay. Jacob?" I said questioningly. I didn't want to push him too fast.

"Oh hell yes!" he said. Why did I keep thinking he might want to go slowly?

"Awesome," Cyndi said. "I promise you'll love it. Both of you."

And so will you, I thought to myself. Win-win-win. "Okay, let's go pick up your stuff and get hiking."

Jacob's Story

The trail leveled off after a mile of scrambling. I had forgotten how steep the first part is. I suppose that's why we're always the only people hiking it. Cyndi had changed into a pair of running shorts barely longer than her pajama bottoms, and a ribbed tank top. Kate was wearing a racerback hiking bra, and had zipped off the legs of her convertible pants. I brought up the rear, wearing the day pack with lunch. It was a warm fall day and the trees were starting to turn. My attention was alternating between Cyndi's well padded ass and Kate's athletic calves. The strenuousness of the climb was the only reason my cock wasn't hard.

As the trail leveled off and Kate's muscular backside was no longer directly in front of my face, I reflected on how my life had changed in the last 24 hours. Yesterday I was in a simple relationship with a beautiful woman who is perfect for me. Happy and comfortable in our lives, with plenty of sex, ranging from very good to excellent. How could it get better than that? Now our best friend was also our... what? Lover? Friend with benefits? At least, but it felt like more. And where was it going? Was this only for the weekend? We had started that discussion in the morning, but got distracted by talking about anal sex. Was Cyndi our sex counselor now? Tutor? Some linear combination of all of the above, I suppose. We just had to figure out the coefficients.

I laughed out loud at my thoughts. "What?" Kate asked.

"Nothing, just nerding out over where this is going." I waved vaguely at all three of us.

"We never did finish that discussion this morning, did we?"

"Got distracted. Speaking of which, did you see what she has in the bag?"

"Nope, it'll be a surprise I guess." She moved closer to me as we walked. "I've been imagining what's in there, and it's making me wet. I'm going to be a wreck by the time we get back."

"Concentrate on the scenery," I suggested.

"I am," she answered, glancing toward Cyndi. Another way our lives had changed. In one day my monogamous, completely straight girlfriend had become unmistakably eager to fuck our friend. Although they hadn't yet gone beyond fingering. Maybe Kate wouldn't enjoy licking pussy, and it would never go further. Of course she would, don't be silly.

"I'm hungry, when's lunch?" Cyndi interrupted my thoughts.

I studied the map for a moment. "Another half mile or so. There's a hidden glen that's a perfect lunch spot."

"I still can't believe you printed out a paper map," she said. "AllTrails not good enough for you?"

"What kind of service are

you

getting?" I asked.

Cyndi pulled out her phone and stared at it for half a minute. "Oh," she said.

"See this is why planning is good."

We got to the lunch place 15 minutes later. "Right behind that rock." I pointed up the trail to a large boulder the size of an enormous boulder. "There's a gorgeous hidden clearing behind it."

Kate led the way, squeezing between two trees. I followed, with Cyndi right behind me.

Kate stopped us and put a finger to her lips. "Do you hear something?" She whispered. There was a rustling on the other side of the rock. "Probably just a deer, but we saw a red fox last time. Quietly."

We crept around the corner. It wasn't a fox, it was a person. No! Two people. Fucking. A woman was facing away from us, naked from the waist down, kneeling over a guy. She was riding him hard, and we could see his shiny cock sliding in and out of her. Her hands were on his chest, and she was moaning in pleasure. We froze in surprise. "Oop!" Kate blurted as we backed away.

"Shit!" the woman said, turning toward us with eyes wide. She jumped up and off her boyfriend and ran past us, stark naked, eyes wide, leaving his penis waving in the air and her pants on the ground. He grabbed their clothes and chased after her, his erection bouncing as he ran.

"Sorry!" I cried, "Don't mind--" But he was around the corner and out of sight. "Rude!"

"Nobody comes here, eh?" Cyndi laughed.

"Well, neither of them did, anyway!" I answered.

We all burst into laughter. "That was unexpected," Cyndi said.

"And kind of hot!" added Kate.

"Oh?" Cyndi responded. "Hmmm."

"What hmmm?"

"Nothing."

"What? You didn't think it was hot?"

"Oh I sure did." Cyndi seemed pleased with herself.

I interrupted the self-discovery. "Well we have the place to ourselves now." I started unpacking the sandwiches. "I doubt they'll be back here for at least, uh, ever."

"Depends on how much they like being seen," Cyndi said.

"Didn't seem like they liked it very much," I replied.

"You'd be surprised what some people realize later," she answered with a glance at Kate. "But let's eat. Too bad we don't have a blanket. We could have a proper picnic."

Kate and I smiled at each other. "Ahem. Planning!" I said, pulling a mini picnic blanket from my pack. "Would you like to share this with us, ma'am?"

We sat cross-legged, knees touching, with the food in the middle: pickles, soft pretzels, grapes, and sandwiches. Surrounded by two beautiful women, my girlfriend and my I-wasn't-sure-exactly-what-but-damn-I-liked-whatever-she-was-becoming, it was the most delicious sandwich I've ever had.

"Have some grapes," Kate handed a bunch to Cyndi, who set them between her legs, returning to the pickle she was nibbling on. My eyes followed Cyndi's hand as she set them down.

"Um. Cyndi?" I said.

"Something wrong?" Cyndi said with a pickle-eating grin on her face.

"You're not wearing panties!" Her tiny shorts had shifted to the side, and I was staring at tender lips and wisps of curly hair.

Kate glanced down and grinned. "Oh my god, you're such a slut!"

"Took you long enough," she said with a smile. "I'm not wearing a bra either."

"Now

that

I had noticed. Isn't that painful for hiking?"

"This top has some support," Cyndi replied. "And it was worth it to keep you amused."

"Are you going to tease us all day?" Kate asked.

"I promise I'll make it worthwhile. I have an idea."

"What?" Kate and I said in unison.

"You two are adorable! I'll tell you when we're done with lunch. I think you'll like it." I had visions of what she was planning for tonight. The possibilities were intriguing. I rearranged my shorts to get comfortable. What did she have in mind? She had the bag of stuff she'd picked up. Toys and lube, she had said. What else? She and Kate hadn't eaten each other yet, so that was a possibility. But that didn't count as a new idea, did it? Did she have a friend she was going to invite? No, things were just getting less weird with the three of us; she wouldn't invite a fourth. Yet. Besides, if she knew someone else she wouldn't have needed this whole weekend. We finished eating in expectant silence.

"Okay, done!" I said, stuffing the trash back into my pack. I turned to Cyndi, trying not to stare between her legs. "What's your idea for tonight?"

"I didn't say tonight," she said. "I think you two should finish what our rude neighbors started."

"What?" Kate said in shock.

"I think you two should fuck."

"Here? Now? What if someone comes by?" Kate's flabber was completely gasted.

"We haven't seen anyone on the whole trail," she pointed out. "Other than the couple here. And they won't be back. What are the odds that someone else comes by?"

"Weren't you saying you thought they liked it?" Kate asked.

"I said they

might

. And even if they did, it's going to take at least one long discussion before there's any chance they'll try again. They won't be back today. Probably."

"Probably?" I asked.

"It's pretty unlikely. What do you think, Kate?"

"I don't think so. Someone else might come by." Her eyes were big.

Cyndi persisted. "I could keep watch. Would that help?"

Kate thought a moment. "Yeah, I guess. I mean..."

"You want to, don't you?" Cyndi was getting her coquette on. "I see the way you've been looking at my pussy."

Kate swallowed and started to blush.

Cyndi looked straight into Kate's eyes and put a hand on her knee. "How horny are you, KDK?"

She looked at me, then back at Cyndi. "Pretty horny." Kate held her gaze and said nothing. "Okay. Very horny. We could... What do you think, J?" She glanced at my shorts.

"I don't know..." I offered, knowing I was going to lose the battle.

"I'll send away anyone who comes by," Cyndi reiterated. "Won't it be nice, here in the open, with the air on your skin, surrounded by nature?" She brought her hands up to her chest. "Look how hard my nipples are from thinking about it." Kate's face was red. "Looks like you're excited too."

Kate was beyond logic. She looked at me. "We could have a quickie? With me on top. You lie there and enjoy it." Her hand went to my crotch.