Cyndi And Friends Ch 04 Choices

Cyndi and Friends Ch. 4

Jacob's Story

I looked at the clock. "Holy shit, it's 10:30. Why didn't anyone wake me?" I sat up and looked around. "Oh, right." Kate and Cyndi were asleep beside me on the bed. Memories of the previous night scampered into my head. It had been nearly midnight by the time Kate had come enough that she let me empty my balls in her pussy, and after 1 AM by the time we stopped cuddling and got to sleep.

They looked adorable lying there among the rumpled covers. Kate, my dear girlfriend, was on her side with her muscular butt peeking out from under the sheet, while our old friend/new lover Cyndi was on her back, one shapely breast demurely hidden and the other delightfully exposed, rising and falling with her breath.

I snuck out of bed and downstairs to the kitchen, not bothering to put on any clothes. "Waffles," I told myself. "Never cooked waffles naked before." I started the butter melting, got out the eggs and milk, and set the waffle iron on the counter. I stared at it for a moment. Right at cock height. I put on an apron.

Kate's Story

As soon as we finished breakfast we went right back to bed. Nothing ike waking to the smell of waffles and bacon and being greeted in the kitchen by the sight of your boyfriend's bare ass peeking out the back of an apron. I doubted I had any orgasms left in my body, but the way he moved when I reached between his legs to fondle his balls, I figured it was worth a try.

Cyndi was wearing only Jacob's unbuttoned shirt from yesterday when she joined us. Between that and Jacob's full and eventually frontal nudity, I felt overdressed in my low-rise panties. The waffles were good though.

Back in the bedroom, we considered what to do for the last day of our weekend. My pussy was still recovering from the night before, so I suggested we start with something not involving penetration.

"Or we could do something totally nonsexual," Cyndi suggested.

"Nonsensical!" Jacob said.

"Agreed," I agreed. "We can't even go for a hike without ending up fucking. Might as well admit it's orgy weekend."

Jacob laughed and continued. "Orgy weekend at Kate and Jacob's. Come for the movies, stay for the come."

Cyndi chuckled. "Okay then, what sexual but non-penetrating activities would you like to try?"

"What is there other than fingering and licking?" Jacob asked.

"Oh Jacob." Cyndi looked disappointed. "There's so much I have to teach you." Her expression turned to excitement. "How about I show you a few new things and you tell me what you like?"

We both nodded. I had no idea what she had in mind, and that realization was making me warm.

"Or don't like," she added. "You can always tell me to stop. What do you want for a safeword?"

"Safeword?" I asked.

"Oh my g--" Cyndi caught herself. "Sorry, just surprised you don't know. A safeword is a word you say if you want to stop."

"What's wrong with 'stop'?" I asked.

"Well depending on what you're doing you might want to

say

'stop' but not really mean it. Like during tickling, or bondage."

"Oh!" I said.

Bondage

.

She must have seen terror in my eyes. "Nothing you don't want to do!" She said assuringly. "It's better to have a safeword to start, in case things progress faster than expected. It's like carrying a condom even when you're not planning on fucking. So, what would you like to use?"

"Can it be two words?" Jacob asked.

"Sure, if you want."

"Teams meeting."

Cyndi and I laughed. "Why that?" She asked.

"Cause it's something I always want to stop and is guaranteed to kill the mood."

"Okay, 'Teams meeting' it is. Say that if you want to stop for any reason."

"Okay, so," I said. "What do you have in mind?" I had sudden images of her riding Jacob with a whip in her hand. "Uh, do we need to discuss... You mentioned condoms. Should we have that conversation?" I wasn't sure I was ready for it myself.

"You said no PIV. Are you changing your mind?"

"I... not... maybe?" I said.

"Okay, that's a no," she said. I was relieved and disappointed. I think she saw that on my face, because she got serious. "If you're hoping I'll make that choice for you, sorry. That's your decision. You and Jacob."

"Okay. Um, thank you I suppose. Do, uh, would... Oh! Does that mean you're a yes if we decide to?"

"Like I said, your choice. For the record I have an implant and a clean STD screen from a few months ago."

"Okay," I said, trying not to let my trepidation show. It could happen. Jacob could fuck her for real with no worries. Other than emotional. And who cares about that, right? I mean, why did I still care after yesterday?

Jacob interrupted my reverie. "And we haven't been with anyone else since we got tested back whenever that was."

I looked at Jacob. "I'm sorry I'm the one who isn't sure. I don't know why exactly--"

"Kate, shh. KDK, I mean," he said with a smile. "I don't need to... put my penis in her vagina. This weekend is already amazing. Let's see what other things she has in mind."

I felt a rush of heat. Desire? Fear? I couldn't tell. But he was right; we didn't have to ask the question yet. And my panties were damp. "Right!" I squared my shoulders. "What do we try next?"

Cyndi's Story

They were ready for some more experimental fun. I suggested three-way oral. I had tried that once and it didn't quite work, so I wanted to try again. We arranged ourselves on the bed with Jacob's face in Kate's crotch, her head in mine, and me ready to suck Jacob's sweet cock. The bed wasn't big enough, but we did our best. My legs had to hang off the edges, and Kate's were shoved against the headboard. It took some rearranging to get in place.

"I can't reach your pussy. Move your hips closer."

"Slide this way a little."

"I can't get your dick in my mouth."

"Hang on, first we gotta get these panties off you."

Jacob tugged them down Kate's legs. "Okay, KDK, kick 'em off!" She gave a mighty kick, whacking the headboard hard with her heel.

"Ow! Geez! Lemme try that again." The second try missed the headboard and ran straight into the bedside lamp. It rocked menacingly, but didn't topple. Her panties were still around her ankle.

"Stop laughing, I got this!" she insisted. "All I have to do is adjust my aim."

She swung higher, missing the lamp and swinging her panties over the top of it. Almost. One leg hole caught on the finial and sprung off her toes back onto the bed, simultaneously pulling the lamp onto the floor. It didn't break.

"Hooray for LEDs?" Jacob said.

"These panties are

cursed

!" Kate shouted.

"Well, they're off at least. Scoot down so I can lick you."

"How's this?"

"Now I can't reach your cock."

"Hang on. This any better?"

"Let me try this."

"Ow! It doesn't bend that way."

"How about if I move over here?"

"Now my neck is twisted all wrong."

"Maybe if I--"

"Ow! My nose!"

"TEAMS MEETING!"

"Okay, that's not exactly what that's meant for, but in this case I agree," I said. "Apparently there was a reason this didn't work the last time I tried it."

"Sorry we don't fit," Kate said.

"No worries," I replied. "I have plenty of other things to try." We were all naked and giggly, and ready to try something else. I went to my bag and got my hand and ankle restraints. "Have you ever tried light bondage?"

Jacob's Story

My stomach fluttered when Cyndi pulled out the handcuffs. "Oh! Um, I volunteer?" We hadn't ever done anything like that, but I had occasionally thought about it, and those thoughts were pretty hot. "How does it work?"

"Help me slide the straps under the mattress," she said. "We can adjust the length so they're comfortable. You want to be my first victim then?" I swallowed and nodded.

"Wow, Cyn. I didn't know you were into this," said Kate.

"I don't tell you everything!" Cyndi said with a grin. "I've had these since college. They've seen some use."

I lay down on the bed and she and Kate wrapped the velcro sleeves around my wrists and ankles. I lay there spread-eagled and nervous as the two of them looked me over.

"You lie there and think about what you've done," Cyndi said.

"Um, what have I done?"

"Made both of us come a lot."

"Is that bad?"

"I didn't say this was punishment! I just said to think about it." I laughed and thought about it.

Kate's eyes wandered over me, from head to toe, lingering at midfield, while Cyndi maneuvered herself into a black leather body harness. Straps criss-crossed her belly, wrapping over her shoulders at the top and through her crotch at the bottom, covering nothing, defining and outlining her body. Her boobs, her patch of pubic hair, her belly, the lips peeking from between her legs.

"What do you think?" she asked.

"Holy shit," I said. "That's hot."

"It's gonna get hotter." She turned around, giving me a view of her bouncing ass, framed by the leather straps. She reached into her bag and pulled out something that looked like a feather duster. "Are you ticklish anywhere?" she asked.

"On his sides," Kate volunteered.

"Thanks a lot!" I said as Cyndi approached, tickler in hand, with an evil grin on her face. Kate smiled.

Cyndi padded toward me, a vision of sensuality. Her breasts were framed by triangles of leather, outlining and emphasizing their fleshy roundness, an erect nipple protruding from the center of each. Below them more straps enfolded her belly, pressing gently into her flesh to reveal its softness. Two loops disappeared around the inside of her thighs, exposing her curly bush and accentuating the puffy flesh of her outer lips. She held the tickler erect, advancing across the floor with a mischievous grin on her face.

I was trapped on the bed, spread and open for her inspection. My heart was beating fast and my cock was fully erect. She placed the tickler against my balls, jiggling it lightly on the sensitive skin. "Do you like that?" she asked.

I nodded mutely. She teased it along my length. A drop of precum was already leaking out as she worked the tickler back to my balls and leaned down to lick the fluid off my cock. I twitched as her tongue slipped over the tip. A gleaming string trailed behind as she raised her head and licked her lips. "I love how you always have so much of this for me."

Without warning, she poked the tickler into my side. I squirmed and cried out, jerking away from it. She moved quickly to the other side. I jerked the other way, giggling, my whole body tensing and flailing from the overwhelming sensation, tugging at my restraints. Back to the first side, and I squirmed again, tugging harder on the cuffs. With a tearing sound my right arm came free. I twisted to see what had happened, and the left arm tore loose as well.

Cyndi dropped the tickler and burst into laughter. "Hang on, let me retighten this." She took one look and shook her head. "Oh balls. The seam is gone. I guess I need better restraints!" We were all giggling now.

"I could hold my hands here as if they were still tied," I suggested.

"That is not how it works, trust me."

"Okay, yeah, obviously not, or I wouldn't have broken them huh? Sorry about your, handcuffs? What do you call these?"

"I don't know, restraints I guess," she answered.

"Well, sorry anyway," I said.

"It's okay, I can get new ones for 20 bucks on Amazon. Or if you want, we can go shop for serious ones sometime."

"Yeah, we can definitely go shopping later," I said, then added, "We're not doing very well this morning."

"Yeah, it's kind of a clown show, isn't it?" she said. "I have another idea, if you're still in the mood." She glanced at my penis. "Looks like you're still in the mood."

"I'll stay in the mood as long as you keep wearing that outfit," I said. She smiled and gave me a thumbs-up.

Kate's Story

Whipped cream! Cyndi suggested whipped cream. I thought that kind of thing only happened in movies, or that Herb Alpert album Jacob's parents used to like. But we had a can of it that was never going to get used because Jacob likes to make it fresh. And it sounded safe against failure, other than being messy. Okay, if it was going to be whipped cream I was going all out!

I leaned against the headboard, spread my legs, and asked Jacob to kneel between them. I pointed the nozzle at my pubis and pressed. With a pfththptptpt it covered my mound. The sight was silly but exciting, the can aimed between my legs, spraying white foam where my pubic hair had been a few days earlier. Back and forth I went, building up a thick merkin of sweet cream. By the time I stopped it was two inches thick.

"Time for dessert!" I whooped, and pulled Jacob's head into my foamy lap.

The splatter covered the bed, reaching the headboard, wall, and floor. He pulled back, blinded by whipped cream. With a loud "foof!" he blew away a blob from his mouth. Straight into my face and the pillows. He wiped most of the rest out of his eyes and right onto the bed covers.

Cyndi collapsed on the floor laughing, flesh jiggling between the leather straps. Her laughter caused me to giggle uncontrollably. Jacob tried not to laugh but I saw his mouth twitching into a smile.

"Welp," I managed to gasp, "I guess it's a true clown show now that someone got a pie in the face!"

Cyndi's Story

It was noon by the time we finished cleaning the sheets, headboard, wall, carpet, and ourselves. Lunch was leftover pizza from Friday night, which we ate while giggling about the morning's adventures.

"I'm no longer sure all this trying new things is such a great idea," Kate said.

"

I've

never had problems that bad before," I replied. "Must be you two!"

"Well I'm gonna sulk then," Jacob said. "Um, but first hand me another slice of the veggie."

"I'm still horny," Kate announced. "Anyone else want to keep trying?" Jacob raised his hand. I nodded vigorously with a mouth full of pepperoni.

There was one area that hadn't been overworked yet. I decided to give them the lesson I had promised. It was time for them to learn about the joys of anal sex.

"Like I said yesterday, when it's good it's really amazing. But when it's bad it's terrible," I told them.

"Like sushi!" Kate added.

"Uh, sure. Yeah, I guess so. Anyway, that's why I haven't done it in a long time. I want to show you the right way so you can enjoy it."

"And so you can enjoy it?" Jacob asked with a lifted eyebrow.

I had to admit he was right. "I promise you'll enjoy it too. And then you'll have something amazing for the future. But yes, I do plan to enjoy grading your practical exam. It has been a long time."

"You said you've done it with women," Jacob said.

"Yeah, I haven't had a dick in my ass in, mmm, five years? But I've done anal with three or four women since then. Let's see, Deneen, Margot? No, she was earlier. Zoe. I guess that's all. Two women."

"Better than guys?" Kate asked.

"Well, better than the last few guys. But it's not the same. There's something about a real dick that feels more... real, I guess. At least for me. It's more intimate. Anyway, I've had good anal from a guy, and it was amazing. And this weekend has made me realize how much I want that again."

"Well, no pressure!" Jacob said.

"No no! No pressure, really. It's... you don't have to do anything special other than follow my lead. Just pay attention and let me tell you what to do," I assured him. "Just follow directions!"

"He can do that," Kate said.

"I know he can," I replied. "That's why I want to do this." I looked at Jacob. "With you. You'll be great, J. I promise." I looked back at Kate. "You're

sure

you're okay with it?"

"Yes. Hell, at this point I probably wouldn't mind you doing PIV. Totally fine with anal."

"Okay," I said. I didn't believe she fully understood, but my needs were getting the better of me. One last caution. "Don't be too sure that it's purely sexual." There, fair warning. I needed him in my ass, emotions be damned.

"Got it. I'll be fine. Plus the point is to teach him so he can do me," she said. It was true. My conscience was clear, and my pussy was warm.

We moved to the living room for the lecture portion of the lesson. We were all wearing loose half-buttoned clothing, and the privates and chests were a distraction, but I did my best.

"We're all clean, so that's good. First thing is to make sure you don't have to poop, obviously," I said.

"Do we need to use an enema or something?" Kate asked.

"Some people like to, but as long as I don't feel like I gotta go then I've never bothered. You can if you want though. I have supplies in my bag."

She looked surprised. "Oh. Oh!"

"You can decide about that when it's your turn." She took a breath. "Okay, there are two main things that make for good anal sex. First, go slow. You have to give your ass time to open up before shoving a cock in there. I like to start with a finger, then move up to a toy, and then it's stretched and ready for a dick. In fact, before you start you should be warmed up sexually. Lots of foreplay, so you're relaxed and eager."

"Okay, that's one thing. What's the other" Jacob asked.

"Lube," I replied. "However much lube you think is enough, go ahead and add more."

"And you brought some, right?" Kate asked.

"Three kinds, baby! I'm always ready with the lube."

"You're the queen slut!" she grinned.

"Damn right!"

"So is that all there is to it?" Jacob wondered.

"We'll get into the details during the practical part," I grinned. "Oh, it's also important for you to be good and hard." I glanced between his shirt-tails. "Good, you're getting ready already." He grinned at me. "If it's not fully hard it doesn't work well. Oh, and since we start with fingers, your fingernails should be nice and short."

"All set there," Kate said. "It doesn't sound very complicated."

"It isn't," I agreed. "And yet, it's amazing how many guys can't do it right. You just gently press your cock against my ass and let it open itself for you." I was getting wet. "Okay, let's go to the bedroom! You can start by licking my clit, KDK."

Kate's Story

Another chance for my tongue to enjoy Cyndi's delicious pussy. How had I lived this many years without that pleasure? I circled her clitoris, licked up and down her lips, and tongue-fucked her until she was squirming.

"Lick my ass!" she said.

Oh!

I hadn't planned on that. She lifted her legs and wrapped her arms around them, holding herself up and open for me. "Just touch it with your tongue." There it was, her cute little butthole right in front of me. She saw my hesitation. "Put your tongue in my pussy and lick downwards." Oh, why not? It was a weekend of discovery; maybe I would like it. I leaned in and did as she suggested. Her pussy was warm and flowing, her slippery juices coating my lips. I slid down, out and over the bottom of her vulva, down further, until I felt my tongue slip into the crinkled depression below. She was clean and fresh, and it was fine.

"Yes, that feels great," she murmured. "Now swirl it around." I did. She moaned in pleasure. I kept going, delighting in how I was making her purr. I could get to liking this. "Yes, like that! Mmmm. Jacob, come over here and rub my clit." I love how she knows what she wants and isn't afraid to tell us.

We continued like that, Jacob softly massaging her clitoris while my tongue swirled around her anus. It tasted of the pussy juice leaking down from her slit.

"Stop licking and put your finger on my asshole," she said. I hadn't realized I was going to be such a big part of this lesson, but I wasn't going to let her down now. "Rest the tip of it on the opening." I did, watching in wonder as it clenched and released in response. "Press lightly on it. Little circles." I continued with my finger what my tongue had been doing, lubricated by the juices flowing down from her pussy.