Cyndi And Friends Ch 01 Popcorn

Cyndi's Story

A slumber party when you're nearly 30? Well, why not? Kate and Jacob invited me to one last weekend, and it was more fun than I've had in ages.

We've been friends since college, but we don't hang out as much as we used to. Work, life, (but not kids at least, yay!), all that stuff. So when they asked if I wanted to come over for an evening of movies and popcorn and staying up late and spending the night, of course I said yes. Then we decided to make it a full-on slumber party and have me stay the whole weekend! They would put their big futon on the floor in the rec room and we could spend two nights watching movies until we crashed.

I needed a break, and really wanted some time with them. Especially Jacob. I have a big crush on him. Have since we met. A whole weekend around him sounded great to me! We flirt and tease each other all the time, maybe a friendly touch on his arm or shoulder. Or his butt. He's got a really nice butt. He does the same with me, and the best thing is Kate's fine with it! She even joins in sometimes. They've been together as long as I've known them, and our flirting has never bothered her. Which is good, cause I had packed my sexiest PJs.

I showed up in a tank top (no bra) and tight jeans around 7:30 on Friday, an hour late as usual, and we hugged and kissed hello. Jacob grabbed my backside longer than usual as we hugged, and I felt my nipples poking his chest. After a very fancy dinner of takeout pizza and soda we all changed into our pajamas, grabbed a bottle of wine and three glasses, and bounced down the half flight of steps to the bottom floor to watch silent movies on DVD until we fell asleep. They still have a working DVD player! They also have one of those cinema style large screen TVs with the light behind so you can make the room real dark, however that works. Anyways, Jacob says it's great, and he's the tech guy. "Kind of cold down here," I said.

"Maybe you should've worn real pajamas instead of... underwear," Jacob laughed, looking me up and down. I was wearing a loose-fitting pair of dusty pink satin short shorts and a tiny camisole in the same thin material. It covered my boobs and not much else. My arms and belly were coming out in goosebumps, and my nipples were poking against the fabric.

"Says the guy in mini-boxers, look at you!" I answered. Jacob's shorts were barely longer than mine, and just as thin. Was I teasing him or was he teasing me? Kate's tall, muscular form was more sensibly but still seductively dressed in skin-tight athletic pants and top. The stretchy material accentuated her muscular frame, and the crease between her butt cheeks made her ass look nearly as yummy as Jacob's.

"Anyways, don't complain, you know you like it," I said to Jacob. He shrugged in agreement. "I just didn't expect it to be freezing down here."

"I'm not complaining!" he replied. "You can wear skimpy shorts around me any time you like." I wiggled for him, the loose edges of my outfit swishing daintily and my boobs swaying under the camisole. "Also a top like that," he added, "Especially in a temperature like this." I turned to give him a profile view of my tits. Kate rolled her eyes. Yep, this was going to be a night of serious teasing. Weekend. We had a whole weekend ahead. Flirting with Jacob was the closest I had been to sex since I broke up with The Last Guy, geez, over a year ago. And now a whole weekend of it? Might be more than I could take. But I was gonna try my best!

He interrupted my daydreaming. "But yeah, sorry about the chill, the heat sucks down here. We're having a mini-split put in as soon as our contractor can fit us into their schedule," he continued.

"A what?"

"One of those heat pumps that mounts on the wall," Kate answered quickly. "Jacob's been going on about them ever since he got back from Europe." Jacob grinned and shrugged. "It will be nice to have some heat down here."

"Plus it can dehumidify in the summer," Jacob piped up. "And they're super effi--"

"Hush! See what I mean? Here, have a blanket." She tossed me one. It was big enough for all three of us. Oh boy!

I poured us each a glass of wine and plopped down on the couch. Jacob turned down the lights and settled in the middle of the sofa with me on his right and the blanket over our laps. Kate started the DVD and crawled under the blanket on his left.

"Much better," I said, leaning lightly against Jacob. Kate snuggled up against him on the other side.

"Yeah it is." Jacob was in his happy place for sure. I liked the way Kate was so accepting of our flirting, even when it got physical like this. Honestly I was more interested in snuggling with Jacob than in watching the movies. Obviously nothing was going to happen, but there was a devil on my shoulder saying "what if" as I settled in. And isn't that what flirting is all about?

It took about 15 minutes for Jacob to finish his wine. He handed me his empty glass and I set it next to mine on the side table, pulling the blanket up to my neck. Jacob and Kate did the same. I was so happy to have them next to me. Especially Jacob. I know he's happy with Kate, and he and I wouldn't work as a couple anyway. He's so concerned about getting everywhere on time, for starters. That would drive me crazy. But I hadn't even been on a date all year, and he was warm and strong and smelled good. My crush was flapping inside my chest like a sheet on a windy day. I knew it was silly, with Kate right there, but between the wine and the blanket and the scenarios I had dreamed up the past couple weeks, I kept slipping into the land of imagination. A land with a lot of images of his fingers, and lips, and tongue.

Kate was leaning on his left shoulder and I was looking at his face, trying not to stare too obviously, enjoying his profile in the light of the screen. Not exactly hunky in a typical way, but there's something about him that I find hot. Mostly the way he flirts, I guess. Confident but unthreatening. And fun. He's always fun. Plus he has those long eyelashes, and his lips are so... Okay, no. I shook my head to clear my thoughts, and he turned to me with a half-grin. "Caught you looking?" he asked.

"No!" I blurted, before remembering the game. "I mean, yes. I was looking. I thought you liked it when I looked at you." I pouted, nearly recovering.

"Don't worry, you can point those beautiful eyes at me any time."

"Oh get a room!" Kate said with a smile in her voice.

I looked around in mock confusion. "Room? Sorry, we've just got this blanket." I was grateful once again that she takes our flirting so cheerfully. Also that she couldn't see the images in my mind. Those had progressed from fingers and lips to something a little heavier. That might go beyond her tolerance level.

Jacob smiled at me in the half-light, and I melted. I took a breath, and pressed my bare leg against his. His skin on mine was tender, warm, and inviting. He made a happy sound as our legs touched. I think. Did he? Did it even matter? Nothing was going to happen with Kate right there. Still, nothing wrong with a nice flight of imagination. And I had an entire airline worth of those. The blanket wasn't the only thing warming me up. Okay, stop. I needed to get ahold of myself. I sat up and concentrated on the TV.

But I kept my leg pressed against Jacob. And he didn't move away.

There was some motion under the blanket, and I felt Jacob's hand on top of my thigh. My eyes went big, and he grinned at me. Okay, more flirting. Settle down, Cyndi, he touches you like that all the time. It wasn't calming my state of mind though.

"Mmmm," I hummed quietly.

His hand started gently squeezing my thigh. Was he touching me in more than a friendly way? I tensed in confusion, then quickly relaxed so he wouldn't think I wanted him to stop. I didn't want him to stop. New images muscled into my brain. Images of Jacob. With no clothes on. Naked Jacob, the guy in all my recent dreams. His name even rhymes, how could I say no? Say no to what though? His girlfriend was right there, it couldn't mean anything. But... it was more than just a touch, wasn't it? Suddenly I was back in high school on the bus home from an away game late at night, wondering if a touch meant something, and what do I do. This couldn't really be happening, could it?

But it was. Something was. I decided to relax, enjoy, and see how far he would go. How far I would go. I took a deep, quiet breath, reached across my chest and put my right hand on his upper arm to show him I approved.

At my touch, he pulled his hand off my thigh. Rats, he misunderstood. I petted his bicep to make my meaning clear. Nothing. I found a combination of courage and foolishness, slid my fingers down his arm, took his big warm hand in mine, and placed it back on my thigh. Too much?

No, not too much. The gentle massage started again, his hand comforting and strong on my skin, my thigh muscle relaxing under his touch. And every other muscle in my body tensing. To clarify the point, I gently rested my left hand on his bare leg. Both of us had chosen well when selecting our pajamas. Yay us!

My brain knew this wasn't going any further, but my pussy was getting different ideas. I started dragging my fingernails slowly up and down his leg, from knee to mid-thigh, closer to his shorts each time. He did the same to me. This was definitely more than our usual flirting. The images in my mind were growing more explicit with every stroke. I slowed. He slowed. I took longer strokes. He took longer strokes. Would he follow anything I did? How far was I willing to go?

A minute went by, both of our touches light, down and back, so slowly. I grew more daring each time, getting tantalizingly close to... well, I didn't want to think about how far this would go. Would I really? Would he? A quick glance confirmed Kate was still engrossed in the movie. Okay then.

My fingers reached the hem of his shorts just as his brushed the fabric of mine. My hand snuck around his leg and started drawing small circles on the inside of his thigh, inches from his... shorts. And then his fingers were on my belly, sliding along my lower abdomen to the other side. I gasped audibly, and tried to cover it with a yawn and stretch. A little awkward since my left hand was occupied, but I made it look pretty realistic. I think. As I settled back down, Jacob rearranged himself slightly.

"Getting bored? We could skip ahead to a different movie." Kate suggested.

"No, no, I'm fine! This is great!" I said, hoping it didn't come out too huskily or hastily. Jacob turned and waggled his eyebrows at me. Yup, confident and fun. Like god damn Groucho Marx. But he had me on the line, for sure. I was ready for whatever was going to happen. Or whatever I could make happen. I decided to see how far I could push things.

I continued scratching lightly with my fingernails on the inside of his leg. His hand moved down my right thigh, which responded with goosebumps. His fingers moved inwards.

I was determined to keep raising the stakes as long as he was, so I continued until my fingers were resting lightly on his inner thigh. His legs were spread wide to make room. I stroked in circles along his leg, feeling the muscles under his warm skin, slowly working my way closer to his body. His hand returned to my left leg and began mirroring my action. I still didn't know where this was going, but it was clearly going. I think I was looking at the TV, but my mind was focused on the sensations under the blanket. On the tingling in my fingers, the stimulating touch gliding up and down my thigh, and on the warmth growing between my legs. I was hungry and moist. His hand approached a tiny bit nearer every time it made the journey back up my leg. My hand drew closer to his shorts each time too.

After all these years of crushing and flirting, was I about to touch his cock? Was he about to touch my pussy? We were a finger length away, and getting closer. I had never been jealous of Kate, but there were plenty of times I imagined Jacob between my legs, or over me, or under. Particularly these recent few months, he had been a regular presence in my completely imaginary sex life. I didn't want to steal him permanently, but a quick borrow for a jump in the sack had been a regular fantasy to support my fingers during those personal moments.

And support them it did. My main thoughts of him lately were about fingers and tongues and nipples and lips and his enormous stiff cock. In reality I knew his cock was normal size (Kate and I cover lots of subjects in our Girl Talk sessions), but in my imagination it was extra. Not so big it would hurt, of course, just the right size. And now, was part of my fantasy happening in real life? The part with the fingers? With Kate right there? It didn't seem right. It didn't even seem possible. In my state what it seemed was inevitable.

Meanwhile his fingers were creeping closer to my shorts. Close enough that surely he could feel the heat radiating from my vagina. Inches away. Tracing slow circles on my inner thigh, closer, further, closer. Tempting, denying, gently gliding over my skin as I did the same to him. My pussy was leaking juices, wanting him. Another stroke, closer still. Brushing the fabric of my shorts, oh for god's sake Jacob touch me!

And, back down my leg. Not crossing that boundary. I closed my eyes and calmed my breath. I was likely to come instantly if he did touch me, and I would definitely be leaving a wet spot on their sofa. Oh god, can Kate smell my arousal? I ventured a look. Nope, still being entertained by the TV and nursing her wine. Thank heavens for a fruity bouquet.

I took the lead again. While he continued his little circles on my flesh, halfway down my thigh, miles from where I wanted him, I went back to dragging my fingernails back and forth along the full length of his. All the way up to the top, making contact with his shorts, across the top of his leg, right at the edge of the material, and... What I wanted would be a lot less awkward with my other hand. I turned toward him slightly and rested my right hand on his leg.

Kate looked over at us snuggling from her position on his other side. "You two are so cute!" she said, nuzzling up to him on that side. "You love this, don't you J?" He nodded enthusiastically. Kate laughed. "I'm so glad we decided to do this. How about you, Cyn? Are you having as much fun as I am?" All I could do was nod. Was I really going to have...? to touch his...? while Kate was right there?

Apparently I was. I was too far gone to stop. But then what? How could either of us orgasm quietly? Or cleanly? Not important! We'd figure something out. Maybe we would stop before we got that far. Reality hit again. Yes, of course that's what we would do. And I could go to the bathroom to finish myself off. Or in bed after they'd gone to sleep. Or both. Except shit, we were all going to sleep on the futon down here like a bunch of hippies. It had sounded like such a great idea earlier. A whole night sleeping next to Jacob! Now I was wishing for some privacy when we went to bed.

Jacob's hand started its long trip back up my leg, and I jerked back to the present. I wasn't going to stop. Not yet. My right hand on his thigh began moving, a slow but direct path sliding my fingertips up to his shorts. It was time for the next step, and see how he reacted. I slipped two fingers under the fabric, tracing across the top of his thigh. An inch from his cock? Less? His hand stopped, squeezed my leg, waited. But didn't withdraw. I slid my fingers out from his shorts, across the top of his thigh, tracing the lower edge of the cloth slowly down between his legs. I felt him twitch. Further down. He was holding his breath. I kept going. Further still, slowly, until I felt warm flesh on the back of my hand through his shorts. My mind collapsed into the sensations in my fingers. Creeping further, I turned my hand around. I was holding his balls.

It was happening. I started gently massaging him through the fabric, intoxicated by the feel of his warm scrotum in my fingers. My mind was twisting into knots. After all these years of dreaming, I was touching him. Was this supposed to happen? Had I gone too far? He answered by putting his hand on my shorts. He pressed down softly, tickling my mound through the silky material.

His balls squirmed in their sack as I traced my fingernails over his flesh. His hand crept lower, I spread my legs further, and three fingers reached my pussy, separated from it by only a thin layer of damp fabric. He pressed inward, and one finger slid between my wet outer lips. My juices were seeping through the material, coating his finger as he slid up and down.

My hand stole upward from his balls, finding the base of his rod. It was firm and hot, and felt as thick as in my imagination. I caught it between my thumb and forefinger and squeezed lightly, caressing the root of his shaft with slow, short strokes, while his finger slid up and down over my shorts, pressing them between my dripping labia. Down to my opening, then back up to the top. He started tracing little circles around my clit, and fire flashed through my body. Down my legs to my toes, up my belly, to my nipples, to my face. I was glad it was dark, because surely I was flushed. I needed him to touch my skin.

As if hearing my thoughts, he moved upward, drawing a trail across my belly with his slippery fingers. Tracing the top of my shorts back and forth, warming and tickling the bottom of my exposed belly. I expanded my motions on his cock, dragging my fingernails across the fabric of his shorts. He made little circles around my navel, and back down. It felt glorious, but my midriff was not where his touch was needed. I took his hand and pushed it downward until his fingers were at my shorts. I pressed it gently against my plump belly until it formed the delightful gap between skin and waistband that would allow him in. Under the elastic he went, slipping gradually downward. I needed his fingers on my clit, between my lips, inside me. Slowly, achingly he crept on, exciting my skin, titillating the upper edge of my bush. Edging so slowly toward my desperate vulva. I squirmed as Tim Curry burst into my head talking about antici...

Jacob's Story

The night was going better than I had expected. I hadn't been sure how Cyndi would react to me massaging her leg, but she was evidently enjoying it. We'd been playing friends-with-flirts for years, and lately she had been getting a lot more physical. Lots of touches on the arm, making contact when sitting next to me, rubbing my shoulders while standing behind me. It had been nearly a year since she broke up with her last boyfriend, and I think she was feeling the lack of intimacy. She's always been keen on physical contact, and I had to assume a year without sex was hard for her. Honestly I was worried about her, and was hoping as her best friend to supply some of that missing physical touch.

I had mentioned my thinking to Kate a month or so ago, but we hadn't come to any decision at the time. Kate is the love of my life, and has never been jealous about Cyndi and me flirting with each other like randy high-schoolers. It's all in fun, and has never extended to anything physical. Maybe an occasional touch on the arm or shoulder squeeze. Or butt-grab. Cyndi does have a butt that's soft and full and perfect for grabbing. Okay, so a little physical, but nothing overtly sexual.

Kate and I fit together almost perfectly, and she knows Cyndi would drive me nuts as a permanent partner. And she knows I know it. Cyndi is a lot of fun and a good friend, and I while wouldn't kick her out of bed if I caught her driving my nuts, she's no threat to Kate and me. Even during the last few months, as she had become more physical with me, it had still been friendly teasing. But she clearly needed more of the human touch. And I wanted to give her what she needed, if that's what she needed. But in terms of details, I didn't know what should or would happen.