Cyndi & 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.

"You're so wet," I said.

"Need more lube for the next step, though," she said. "Jacob, go get the pink tube from my bag and put some on her finger and around my asshole." He did.

"Now slide your first knuckle in slowly," she said when we were fully lubricated. I pressed against her opening and watched in wonder as the first inch of my finger slipped inside. "Yes, like that." She squeezed my finger with her sphincter.  

"Oh!" I exclaimed. "It's so tight!"

"Just giving you a hug," she said, laughing. "You can push it in another inch." I did. "Feel that now?" There was another constriction. "Push gently to get through the inner ring. Slowly." I pressed lightly until I felt it yield to my pressure, opening to let my finger deeper in. It was tight and warm, and Cyndi was humming in pleasure.

"I see why guys like this," I said. Jacob was watching in fascination as my finger slid into her.

"Wait till you feel it from your side," Cyndi replied. "I think it's even better for us. When it's done right."

"Am I doing it right?" I slid further in.

"Oh yes! Give me some in and out now. Slowly."

I slid my finger slowly back and forth inside her, feeling her insides open and adjust to me. The tightness was intoxicating, as were the sounds she was making. "Mmm, that's really good. Now it's time for a toy. Jacob?"

He pried his eyes away from the sight in front of him and peered into her bag. "Um, which one?"

"See the green rubber butt plug?"

"With the wide base?"

"That's the one. Bring it over and put plenty of lube on it."

I held it against her opening, circling it lightly. "Yes, tease me like that," she said. The toy was tapered, slightly thicker than my thumb at the widest point, narrowing to a smaller diameter before flaring out at the base. Jacob had slathered it with lubricant. "Now put it in slowly." 

It slid in easily, spreading her ass and slipping inside the tight hole. I watched her anus spreading, opening to the toy as I pushed it slowly deeper. When I got past the widest part her muscles closed on it, pulling it in the rest of the way. "Ah, that's why it's big at the end," I said.

"Yep. Nothing worse than getting something stuck up your bum." I laughed. "Okay, pull it out. Very slowly" I did. It held tight at first, but she urged me to keep pulling until it slipped past the wide part and emerged from her ass. "Back in." I slid it back in.

"This is so good," she said after several minutes of me playing with her ass. "I'm ready for the main course now. Jacob, are you?" 

He moved so she could see his erection. It was stiff and throbbing. She smiled. "Good boy."

I leaned some pillows against the headboard so I could watch. Cyndi lay on her side with her feet toward me, making sure I had a clear view of her ass with the bright green toy sticking out of it. "I like to do it in spoon position, at least to start," she said. "That way I can control his movement." Jacob sat behind her, his cock stiff and ready. He was about to slide it into her ass, and I was going to watch. A warmth spread through me at the thought.

"Put some lube on it, KDK," Cyndi said. I squirted a blob onto his cock head and took my time spreading it up and down his shaft. He looked at me with lust in his eyes.

I returned the look. "Do what she says, baby. I want to watch you fuck her ass."

"Pull out the butt plug, J. Slowly, like Kate did." I watched as he gently tugged on it, her anus holding onto it, stretching as he pulled, then releasing and letting it slide smoothly out. "I'm ready for you," she said.

He lay down behind her. I adjusted my position so I could see clearly. She reached back and grasped his erection, wriggling until her opening was pressed against the head. It was happening. "Push, baby," she said. "Slowly."

His hips moved forward, pressing his cock against her hole. I watched as it began to spread, allowing him inside. She moved her hand to his hip, guiding him as he penetrated her ass. The head of his cock was inside her now, his glistening shaft disappearing into her.  

"Hold there for a minute." She had a look of bliss on her face. "Can you see, KDK?"

"Yes," I breathed. My fingers were on my pussy.

"Ready," she said, tugging on his hip to guide him deeper. His hips moved almost imperceptibly, nudging his penis further in. "Yes, just like that." Another half inch of his shaft disappeared into her. "There, feel that?"

"Yes," he said.

"Slow again. Go ahead."

He moved again, penetrating her further. Half of his shaft was inside her. My fingers danced across my clit.  

"More."

"It's so tight, Cyn. It feels so good." Another half inch vanished.

"Yes. Keep going." She pulled him toward her. "All the way in." He was. Her eyes were closed in pleasure, her mouth open and breath ragged. She removed her hand from his hip and lifted her knee, exposing herself to me fully. Her pussy was wet and puffy, her clit swollen, peeking out from under its hood. Her beautiful soft glutes framed the sight of Jacob's cock embedded deep in her ass, his balls draped over her lower cheek.  

She moved her hand to her clit. "Start moving. Slowly." He rocked his hips and an inch of his shaft reappeared out of her anus. Another inch, and he reversed, pressing inward. Her fingers began moving across her clitoris as he stroked slowly.

She guided him with her words. "Take it all the way out and play around the opening." "Put it in slowly." "Speed up." "Deeper." "Slower." "Faster."

"I wanna be on top," she said after a while, tilting her hips forward. His shaft emerged slowly from inside her, wet and stiff. No worries around how hard he was. Her hole closed up as the tip of his cock slid out.

She rolled him onto his back and climbed aboard. Reaching between her legs, she positioned his rod against her tight hole and gently leaned back. I couldn't see her face, but I could hear her pleasure as the head of his cock disappeared inside her. She held halfway for a moment, then with an agonizing slowness lowered herself onto him all the way. My fingers stroked my clit hard as she sank his penis inside her bowels.  

"Oh, yes, J. You've opened me up so well," she moaned. "I love when I can get it all in like this." She started rocking back and forth, the motion I like when I'm on top. I imagined her clit rubbing against his pubic bone as she moved, and how good it must feel. My fingers moved faster. I was going to come.

"Oh baby, yes!" Cyndi cried. "Here it comes. Here it comes. Oh god. Keep going just like that!" 

"Me too!" Jacob gasped. "I'm gonna come."

"Yes!" 

"Oh god! Ahhhhh!"

"Ohhh!"

"Mmm-hmmm!" My orgasm surged through me as Cyndi's body convulsed. Jacob's hips thrust upward, driving his cock deep into her. Her legs twitched, her toes curled as she cried out her bliss. We were one orgasm crashing over three bodies, voices crying out in joy, faces flushed, cock thrusting deep, anus contracting in waves, fingers kneading hard against clit. I lost sight of them as my eyes rolled back and I gasped for breath. Cyndi's arms gave out and she collapsed on Jacob's chest.

I opened my eyes and tried to focus. Cyndi was jerking and gasping, then sobbing on Jacob's chest.  

"Baby, what's wrong?" he asked.  

"Not wrong," she got out between sobs. "Just hold me."

He wrapped her in his arms, his cock still buried in her ass, shrinking and gliding out little by little as her body jolted with each breath. After a minute it slipped out completely, and the whimpers mixed with giggles for a moment. She rolled them onto their sides, still clutching each other. I sat there not knowing what to do. She put her hand behind Jacob's head and pulled his lips to hers, still gasping. She kissed him for what seemed like hours, snuggling in his arms. I watched.

"Whew," she said when she could breathe again. "I forgot how emotional I can get after an anal orgasm." She wiped her eyes and kissed Jacob again. "Although I have to say, that was the most intense one I've ever had. Intense and intimate. Thank you, J. You're wonderful."

"I did good?" Jacob asked.

"Oh J, so much more than good. Where have you been all my life?"

Jacob's Story

"He's been right here," Kate said, with a hint of annoyance. Was she jealous?

"Don't worry, baby, you're next." I rolled away from Cyndi and looked at my cock. "Although not for a while. I think this is the first time all weekend I've been completely flaccid!"

"She really drained you, huh?" She was jealous.

"Hey, baby," I replied. "I'm not... I just need a break."

"Intense for you too, huh?" she asked.

"Not in the same way," I answered. "But..."

"But what?"

"Baby..." She saw the look on my face.

"Sorry. I'm sorry," she said. "I'm okay, really. But I need to know how it made you feel. What was the 'but'?"

"The butt? That's where my dick was!" 

"Ha ha. What were you going to say?"

"Sorry! Just... Cyndi was right about it being intense."

"As intense as in the vagina?"

"Maybe more, in some ways?" I said, unsure of how much I should share at that moment. "Like, well, it did feel very intimate." I searched for words. "I guess it's the feeling of trust? Like I'm putting my dick somewhere that could be painful? Y'know, she's stopped doing it because people hurt her, and she trusts me enough to let me in. And then when she ended up all verklempt afterwards, it's sort of, I don't know, even more fulfilling emotionally than physically. Does that make sense?"

"Yeah, I guess so."

"I promise you'll feel it too. When you're ready," Cyndi said. "Right now I need to clean up. You do too, Jacob."

"You wanna come shower with us, sweetie?" I asked.

"No," Kate said. "You two go ahead."

"You sure?" I asked.

"Yeah, I'm fine. Go." We climbed off the bed and headed to the bathroom.

I warmed up the shower as Cyndi sat on the toilet. "I'll join you in a sec," she said. "As soon as I shart out all your cum."

"Well that's a sexy thought," I said as I climbed into the shower and adjusted the temperature.

"Sex is messy," she said. "Anal sex especially so. No point being pretentious about it."

"Fair enough," I agreed. "So uh, should we wash our own selves? I don't want Kate to have any reason to feel worse."

"You understand why she feels that way, right? You and I shared something a lot more intimate than she expected, and it's going to take her a while to process it. But I know her well enough that I know she'll be fine."

"Yeah," I agreed. "You did try to warn her."

"I did," she said with a wry smile, stepping in beside me. "And she'll realize it eventually. Plus it'll be her turn next, and hopefully she'll have the same kind of response. I'm sure she will, once she has this buried in her ass..." She grabbed my cock with a soapy hand, "When that happens I think she'll understand. And we'll all be closer to each other. Anyway there's no point wasting a good two-person shower washing by ourselves." She stroked my penis. "Oh, looks like you'll be ready again quicker than I thought."

"Just get me clean," I said with a grin. "I'm saving the next erection for her."

We washed each other platonically, sticking entirely to what was necessary for hygiene. I was no more than half erect when she finished cleaning my dick, and I barely enjoyed the feel of her bouncy ass cheeks in my fingers as I soaped them carefully on all sides. The two or three minutes I spent washing her butthole was strictly for sanitary purposes, as was the detailed attention to the rest of her pelvic area. And her hands all over my ass were only because the lube had gotten everywhere and needed to be fully cleaned off. The five minutes I spent on her boobs may not have been absolutely necessary.

Cyndi's Story

"Let's play hooky tomorrow!" I suggested. Kate had not said much during dinner, and I hoped another day together would improve her mood.

"Okay," she replied, less enthusiastically than I had hoped. "You guys okay to skip work?"

"I have nothing on my calendar," I said. Jacob gave a thumbs-up.

"Let me send an email," Kate said. A minute later she called out "Aw, shit!" from her laptop.

"What?" I asked.

"I forgot I have a meeting at 9 that I need to attend. I can't stay home."

"Well, ass!"

"That's what I was hoping for," she said. "Now I have to sit in a conference room instead." 

"Well that sucks," Jacob agreed. "And not in the good way."

She thought a second. "The meeting should be done by noon. I could still take the afternoon off."

"Do it!" I urged. She typed some more and sent the email. "Great. What do you want to do tonight?"

"Board games?" Kate suggested. Not ready for more sex. No problem.

"Okay," Jacob said. "Catan?"

"Sure, haven't played that in a while. But... Can we talk first?" I asked. "About how you're feeling."

"I'm fine," she said, obviously not fine. "You guys had anal sex, like we planned." I sat quietly, waiting for the next part. Jacob took a breath to say something, but I gave him a glance and he kept quiet. "It's just..." Kate continued. Here we go. "It wasn't what I was expecting. I thought it would be hot and sexy and orgasmic, but... Well, it was that, holy shit. But... You said it was more emotional than sexual," she said to Jacob.

He nodded. "Yeah. I wasn't expecting that either, if it helps."

"Does that make you feel jealous?" I asked.

"No! It's fine."

"Fine?" I asked. "Can you find a more precise word?"

"I don't know. It is fine. I'm okay with it. I want you to have that connection. I guess it was... you two got this powerful emotional bond and all I had was an orgasm." 

"A good orgasm, I hope?" I suggested.

"Yeah, actually amazing." She laughed as she said it. "Sounds stupid when I say it out loud, doesn't it?"

"Not at all," I assured her. "Think about yesterday. How did you feel after we got done eating each other? Was that nothing more than an orgasm?"

She laughed and actually blushed. "That was like twelve orgasms! But okay, yes, it was more than that." She thought a moment, her eyes fixed on mine. "Yeah, a lot more. Oh Cyn, I... Is that how this felt to you?"

I nodded.  

She took a deep breath. "Okay, yeah, I'm being silly. I need to... I don't know what I need."

Jacob looked at her longingly. "I still love you as much as ever. Maybe more."

"I love you too." Her eyes were wet.

He went to her, knelt beside her chair and wrapped his arms around her.

"Isn't that uncomfortable?" she asked.

"Loving you?" he asked with a gleam in his eye.

"Your knees, silly!" she said, laughing despite herself.

"Don't care," he replied, pulling her to him for a long kiss. "I love you always."

"Thank you love," she said. "I'll be okay. Now get up off the floor before you hurt yourself!"

"So. Catan then?" I asked.

"Yeah," she agreed. "Anyone got wood for sheep?"

Jacob's Story

An alarm started ringing somewhere in my dream. I figured out what it was, that it was real, where it was, smashed the off button, and looked around. Right! Two women in my bed. I crawled back under the cover and snuggled up behind Kate. "Good morning loves," I said. "Thanks for a lovely game night."

"Good morning you two."

"Morning, wood." Kate snuggled back into me, pressing my erection between her cheeks. I wriggled against her.

"Time for breakfast. And then you've gotta go," I said with disappointment.

She rolled over and put her hand on my cheek. "There's something I want you to do while I'm gone." She looked nervous.

"Anything, baby."

"I want you to fuck Cyndi."

I was shocked. "You mean to say... as in..."

"I mean to say. In her vagina. With your penis."

"If she wants me to, you mean," I added.

"I want you to!" she called from the other side of the bed.

"And if you want it of course," Kate added. "You do, right?"

"Well yes, of course. If you... If you're sure."

"I had a lot of time to think about it while not sleeping last night. Cyndi is right; she and I already had the same connection you two had yesterday. It's ridiculous of me to be jealous; you were downstairs making us dinner while she and I were, um, making that connection."

"To be honest, I was feeling kind of left out then," I admitted.

"Well you didn't show it anyway."

"You guys sucked my dick right afterwards! Together! It was hard to stay grumpy."

"That wasn't the only hard thing!" Cyndi piped up.

Kate managed to restrain her laughter. "We're trying to have a serious conversation here." She turned to Cyndi for a moment. "Do you want to get laid or not?"

"I'll shut up."

Kate turned back to me. "Anyway, yeah. You've been so loving and kind this whole weekend. It could have been an emotional nightmare, and I had no idea how fraught it was when we started. I can't imagine doing this with anyone else but you. I love you, J. So much. I want this to be more."

"Why while you're gone?" I asked.

"Well, it'll keep you entertained, for starters."

"True. But I could always lose another game of Catan," I ventured.

She laughed. "You are good at that! But also, I had that alone time with her. While you were making dinner. I want you to have the same." She paused. "There is one thing though."

"Anything," I said.

"You're only allowed to come once. When I get back I want you hard enough to fuck my ass. Can you do that for me?"

"I can do almost anything with an incentive like that!"

Cyndi's Story

After breakfast, Kate kissed us both and headed off to work. It felt like a TV show domestic scene, if TV shows had happy throuples living a suburban life. Not that we were a throuple. Yet. Were we? I didn't feel like I was in control of anything any more.

"Wanna come up to my place?" Jacob asked. He had worn the usual attire for the weekend, which is to say a shirt. His penis was visible between the tails, not hard but thick and heavy. My god how I wanted it in me. Had wanted it for years, and it was finally happening. He was taking me to bed. His erection rose as he looked at me, adding to the warmth growing between my thighs. He took my hand and led me up the stairs to the bedroom.  

Standing in front of me, he slowly undid the shirt I was wearing, one button at a time. When the last button was open, he silently pushed the shirt off my shoulders. My breasts emerged as it fell away. I stood naked, ready to give myself to him.  

I opened his shirt, brushing against his cock as I undid the final button. We stood there naked and aroused, nipples engorged, penis erect. I was nervous. Nervous! How many times had I seen him naked in the last days, touched his cock, swallowed his ejaculations? He had come in my ass, for heaven's sake. Why did this feel different?

I knew why. It wasn't about Jacob, it was about Kate. This was her red line, and she had chosen to cross it, giving her boyfriend to me and trusting him to maintain his love and desire for her. And trusting me to leave enough of him for her. I suddenly felt an enormous wave of love for Kate. Funny how letting Jacob fuck my ass brought me closer to him, and letting him fuck my pussy brought me closer to her. Love is a strange beast.  

Love? Shit. Is that what was happening? And what did that even mean?

I was lying on the bed facing Jacob when I came out of my reverie. He was brushing my hair back and looking at me. "Tell me what you're thinking," he said.

"Oh Jacob," I replied, ruffled by my own thoughts. "So much. Where this is going, what is happening to us."

"What do you think is happening?"

"It's hard to tell. It's all so fast, I need more time to figure it out." 

He slid his arm down mine and took my hand in his. "Well, what do you want to be happening?"

I thought for a moment. What did I want? I took a breath and let it out. "I think... I think what I want is for this to continue."

He smiled like a kid in a candy store. "Can you be more specific? What do you mean by 'this'? I mean, obviously having sex with us, but..."

I finished for him. "There's more to it than sex, isn't there? Have you, y'know, caught feelings, as the kids say?"

"Mm, I don't know if that's the right way to put it. I've always had feelings for you, y'know. I just kept them on a low simmer, cause, well... everything."

"Kate?" I suggested.

"Yeah. But also, being your friend, and not wanting to risk that. And y'know, I never figured you had any feelings for me. More than friendship, I mean."

"All those years of flirting and you thought I only liked you as a friend?" I asked with a smile.  

He smiled too. "I mean, it was mostly that I'm with Kate. And I figured the flirting was just friendly, uh, fun." 

We lay there a while, staring into each other's eyes, enjoying the moment. I removed my hand from his and ran it down his side. "So, not caught feelings, but, what? Grew them?"

"Engorged?" he suggested. I laughed and moved my hand to his cock.

"Yeah, definitely that," I agreed. I stroked lightly up and down his length with the back of my fingers.

"Sorry," he said. "You're trying to have a serious conversation. I shouldn't be so flippant."

"That's one of the reasons I like you."

"So what do we do next?" he asked. "Like, with exclusivity? Do you want... What do you want?"

"I think it's too early to answer that. Which I guess means we're not exclusive, doesn't it? Are you okay with that?"

"Yes. Absolutely," he answered. "At least, I think so? I'll probably get jealous if you sleep with someone else, if I'm being honest. But of course, this was all meant for your benefit, so it would be shitty to put a claim on you. So yeah, that's fine. Hopefully Kate feels the same. Guess we better ask her."

"Yes," I agreed. "And we need to see how things go before making any big decisions. But..." I took a breath. "Right now, I don't want anyone else. What I want is to be with you all the time. You and Kate. Whenever we can."

"Whenever you want."

I kissed him. Our tongues met and danced. I reached for his butt and pulled him to me. His erection pressed against my leg. "Hello there, Captain Horny," I said, wrapping my fingers around it. "I guess we should stop talking and have sex before your girlfriend gets back."

He nodded. "I agree! But first, can I ask you a favor?"

"Of course."

"I haven't tasted you yet. Can I lick your pussy?" He sounded like a little kid asking for candy.

I felt myself getting wet. "Oh god you're right! I've swallowed your cum twice and you've never tasted me." I unwrapped myself from his arms, rolled onto my back, and spread my legs. "Show me what you can do!"

"I was hoping you would tell me what you like," he said as he settled himself between my thighs and slowly looked me over with lust in his eyes.

I smiled. "I can do that. Start with my toes."

Jacob's Story

She lay naked before me, legs spread and knees up. The look on her face said it all. The red in her cheeks, her gaze meeting mine, the smile in the corners of her eyes. Her full lips parted, the tip of her tongue snuck out and licked her upper lip, retracting wetly as she bit her lower one. The corners of her mouth turned up in a devilish smile. "Start with my toes," she said.

I let my focus drift down her body. Her bountiful breasts swayed enticingly, rising and falling with each breath, her nipples firm little pebbles as always. How is she so different from Kate and still so beautiful?

Her belly, soft and curvy, the perfect indentation of her navel in the middle, bordered at the bottom by the triangle of her pubic hair. I held my gaze on her bush, short and neatly trimmed, pointing inescapably to the delicious snack between her legs.  

Her pussy entranced me. With her legs spread like this, her inner lips were revealed, petite and inviting. At the top, a small gathering of flesh daintily covering her clitoris, at the bottom a drop of wetness slowly dripping down to her tight brown anus.  

My eyes drifted onward to her thighs, soft and tempting. I touched her. Starting from the fold where thigh meets body, I traced a path down the insides, her flesh yielding under my fingers, smooth and warm. I reached under her left knee and brought it toward her chest, opening her sex to me further. But as enticing as her pussy was, she wanted toes. I brought her foot to my face.

"Suck them," she said. She moaned happily when I put her big toe in my mouth and circled it with my tongue. "Yeah, like that."

I let her guide me in pleasuring her. "Squeeze the other ones." "Run your fingers up my legs." "Tickle my foot." 

"Wait, really?" I asked.

"Yes. Hold it tight, I'm gonna squirm." She twisted and giggled as I ran my finger along the sole of her foot. "Ooh! Hee hee! Keep doing that." 

After a few minutes of wriggling and laughing she took a breath. "Okay, stop and nibble on my toes again." Her eyes rolled back as I dragged my teeth across each toe in turn. "Now do the inside of my thighs." I trailed my fingernails down the inside of her left thigh, starting at the knee and slowing as I approached her crotch. "Keep going." Her breaths were getting short.

I continued slowly, letting my fingers brush against her outer labia, then did the same to her right leg. "Oh yes!" I nibbled her toes some more, lightly stroking the crease between leg and body. "Keep going"

I ran my fingers through her bush, enjoying the soft curly hairs against my skin. I began making gentle circular motions on her mound. The hood of her clitoris moved side to side as my fingers circled past it, never touching it directly. She began squirming again, lifting her hips toward me. "Touch me."

I snuck downward until my fingers were brushing her nubbin, teasing it with delicate strokes. "Suck my big toe like it's a cock."

"I've never sucked a cock though."

"You should try it sometime, it's lots of fun. Especially when it comes in your mouth."

"I don't think your toe is going to do that," I said.

"Stop talking and suck!" 

I complied. She moved under my hand as I stroked her button, her leg twitching when I sucked her toe. In and out of my mouth, my tongue circling it, teeth nibbling gently, two fingers working her clit, stroking it like a tiny cock. Her hips began to writhe as I played with her, twisting and lifting for more pressure. Her breathing was rough, her eyes closed.  

"Yes. Keep going. Harder. Slow down. Not faster, just harder."

Keeping my fingers on her clit, I pressed between her pussy lips with my thumb. Sliding it up and down her slit, sucking on her toe, my other hand lightly brushing through her bush.

"Oh! I'm gonna come!"

I nibbled harder on her toe, pressed my thumb into her opening, and watched her orgasm erupt across her face. Her eyes opened, rolled back, then closed. Her mouth opened and her cheeks flushed. Her face scrunched and her head arched back as she cried out wordlessly. Her hips thrust upward as I drove my thumb into her, squeezing her clit tight between my fingers.  

As she came down I shifted my hand off her clit and slid my thumb further inside her pussy, still sucking on her toe. She continued writhing, opened her eyes and smiled at me. "Yes, keep going. Make me come again." 

I pulled off her toe with a plop and moved to her other foot. Nibbling on it, I moved my free hand to her breast, circling her nipple. "Squeeze it!" she demanded, arching her chest upward when I did. I reorganized my other hand to slide two fingers in and out. Pinching her nipple, finger-fucking her pussy, nibbling her toes, watching her writhe in pleasure, her eyes staring at me. "Clit!" she called out. I moved my fingers back to her clit and another orgasm surged through her body.  

"Oh! Oh yes!" Cries of joy, spasms rocking her hips, her toes slipped out of my mouth as I stroked her. I drank in the sight of her O face for the second time in as many minutes.  

She came down from this one more quickly. "I thought you wanted to eat me," she suggested.

I removed my fingers and shifted position, bringing my face a few inches from her pussy. I could see the wetness dripping from it, smell her arousal. "Like this?" I asked.

"Closer."

I moved closer. I was sure she could feel my breath on her. "You smell delicious," I whispered.

"If you'd ever taste me you'd--"

I pressed my tongue against her clitoris.

"Ahhhh!" She moaned and thrust her hips against my mouth. I licked in circles around her clit, slowly but firmly. Then down between her delicate inner lips, penetrating her briefly before licking my way back up to her pulsating nubbin.  

Up and down I licked, slowly, relishing the taste, the scent, the feel of her lips on mine, the way her hips moved when I circled her clit with my tongue. I slid a finger into her and curled it upward, sucking on her button as I did.

"Oh god! Oh Jacob! Don't stop! Don'tstopdon'tstopdon'tstop!" Her juices flowed as her orgasm washed over her. Crying out, clutching the sheet, hips thrusting into my face, my head clamped between her thighs. I kept licking her until she pushed my head away, panting and exhausted. "C'mere," she said.

I crawled up her body. She pulled me to her and kissed me, my face soaked with her juices. I felt my engorged penis brush against her wet labia.  

"It's time," she said. I raised my hips. She reached between us and grasped my erection, sliding it up and down her slit and leaving it aimed at her opening. She placed her other hand on my butt. "Fuck me, Jacob." She pulled me into her.

Her pussy was wet and warm and slippery. I slid all the way in with a single stroke. "Oh Jacob," she whispered. "In me at last." She gazed into my eyes and wrapped me in her arms. I held there, my penis buried in her vagina, enjoying the sensation of her flesh enveloping me, warm and tight. Years of flirting and teasing, and now I was inside her. I couldn't believe the feelings of satisfaction and love flowing through me.

"Fuck me," she repeated. "Or are you just going to soak there like a Mormon?"

I smiled and laughed. "Sorry Cyndi. Cyn. Your pussy feels so good, if I move I'm going to come."

"Yes baby, do it! Come inside me."

"What about you? I want you to--"

"I don't need to come again! I need to feel you filling me with your cream. Come in me J. Squirt your jizz inside my pussy." She put her hands on my butt and rocked me against her. "Fuck me, baby."

I started moving. I pulled all the way out, leaving the tip of my cock nestled between her labia. "Oh, Cyn. So good." I slid back into her, grinding against her pubic bone. Then back out, and in, her hands pulling me deep, her hot flesh opening to my penetration. Squeezing me, milking my cock.

"Come for me," she repeated. Another stroke, and I felt my orgasm building.

"Oh yes," I whispered. "Here it comes."

One more stroke. "Yes, baby. Come inside me." My shaft tingling, balls drawing up, breath getting short. "Yes, yes." Out. In. "Now baby. Now!" I tensed, balanced for a moment on the edge, and came. Thrusting all the way in, crying out my pleasure in gasps. I felt my semen rushing through and out the end of my cock into her tightness. "Yes! Come Jacob. Come in my pussy!" She thrust her hips against me as I drove into her. Another pulse of cum gushed out. My body trembled. Her arms wrapped around me and her lips met mine. Another spasm, and another, more cum, more joy. Her hands back to my butt cheeks, pulling me deep inside as I poured out my orgasm deep in her belly.

Finally we were still.  

"Hi guys!" Kate was back!

"Hi KDK," Cyndi said.

"That was beautiful," Kate said with admiration. "How long have you been at it?"

"About a minute," Cyndi replied.  

"What?"

"Or 20 minutes if you count the oral sex."

"What have you guys been doing this whole time?" Kate sounded shocked.

"Talking, mostly," I said. "Entirely, I guess."

"Like friends do," Cyndi added.

"Yep, just being friendly," I agreed, pulling my dick out and rolling off her chest.  

"Not falling in love?" Kate asked with a smile.

I took a breath. "Maybe a little," I admitted. Cyndi nodded.

"Good, cause I think that's what I'm doing too. So did you have fun?"

Cyndi rolled over and wrapped her arms around me. "This guy knows how to make a girl come!"

"He does," Kate agreed. "You two look so adorable, but..."

"What?" I said, worried.

"Well, aren't you... y'know... hungry?"

I laughed out loud. "I guess so. What time is it?"

"12:30. Let's have lunch so I can have my ass fuck!" She started unbuttoning her shirt.

"Can I..." Cyndi interrupted herself. "Hang on, I should get a tissue or a towel or something." A blob of semen was oozing out of her pussy and onto the sheet. Kate grabbed a tissue and handed it to her. "Thanks."

"What were you going to ask?" I asked.

"Oh right. It's very distracting how much of a mess you made inside me." She continued as she cleaned up. "I was gonna ask, can I come over next weekend?"

"Yes!" we both started.  

"Oh wait," I said. "Next week we're going camping." My eyes lit up. "Join us?"

"I don't have a sleeping bag," she said. Then, enthusiastically, "But I could get one!"

"We can go shopping with you!" Kate gushed, wriggling out of her sleeves and unbuttoning her pants.

"We'll need a bigger tent too," I noted.

"REI run!" Kate and I whooped in unison.

Cyndi grinned and grabbed my penis. "Given what's going to happen in that tent we should probably go to Dick's instead."

"Ha!" I said. "But no. REI is right down the street, and they have better stuff. Tuesday night shopping run?"

Cyndi shook her head. "I'm busy Tuesday night. Wednesday?"

"That works," Kate said. "And... it's so far back to your place. You could sleep here after the shopping." She batted her eyelashes and let her pants slide to the floor around her feet.

Cyndi smiled. "I'll pack a bag."

"With more than just tiny lingerie I hope," Kate snickered as she undid her bra.

Cyndi rolled her eyes."Yes, I'lll bring work clothes for the morning."

"Great! It's a date!" I said while Kate peeled off her panties.

"Okay," Kate said, slipping into one of my shirts. "Let's eat, and then," she grabbed my penis. "it's time for a chocolate churro. Are you up for that?"

My half-erect cock grew three sizes. I smiled and gave her a big thumbs-up. "Yes," I said.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Here ends the story of Cyndi, Jake, and Kate (for now, anyway). I hope you enjoyed it. I spent forever letting it age and going back to edit. There are more stories to write, in this world and others, which I'll post when they escape my brain. Thanks for all the kind words, and I'll be back soon.