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Up All Night

Disclaimer: This is a work of fiction concocted entirely within my imagination. Any resemblance to real people shouldn't be surprising since most of my stories are based on people I know. While I hope you enjoy this story and are compelled to provide feedback, I don't expect the subject matter will appeal to everyone who reads it. As such, I discourage venomous, nasty feedback full of violent wishes against essentially fictional characters in fictional situations. If this story does not appeal to you, there is undoubtedly one somewhere on Literotica that will, so your energy will be better spent on finding it rather than on vilifying me.

I had no idea why I was having so much trouble falling asleep; I was physically tired and hadn't consumed any caffeine, but I guess I just wasn't sleepy. Before I completely annoyed the guy I was sharing a room with by tossing and turning all night, I finally got up and just figured I'd hang out downstairs where I wouldn't bother anyone. As I made my way down the hall to the stairs, I could hear the snoring of what sounded like everyone else who was on the retreat. We were in a big, old farmhouse out in the woods and had spent the day doing maintenance and landscaping, a volunteer activity that most of us participated in at least a couple of times a year. The work had apparently worn out everyone except me, or so I thought. At the bottom of the stairs, I could see through the kitchen and into the living room, where somebody sat on one of the couches with a lamp on and her back to me. It looked like Karen and, when she turned to see who was crossing the squeaky floor, my suspicion was confirmed.

"What are you doing up?" she asked, once I was close enough that I'd be able to hear her whisper. I sat beside her on the couch, noting that she wore a white nightshirt with apparently nothing under it.

"Couldn't sleep," I replied, "and you?"

"I couldn't sleep, either," she said, "I felt as though I'd had an espresso with dinner...wide awake."

I could tell that the wheels were spinning inside her head; Karen was a modern-day hippie who saw a deeper meaning in every event, no matter how minor. While she figured out why we both ended up awake in the middle of the night, my eyes dropped to admire her body. She had pretty large tits, that appeared to be standing up pretty firmly despite the apparent lack of a bra, and though I couldn't see up under her nightshirt, I checked her hips and didn't see anything through the white material that suggested she was wearing panties. The idea of her being naked under her nightshirt was very appealing but I had to be careful that I didn't pitch a tent in my lounge pants. I doubted that she'd reach the conclusion that, if we were both awake, we might as well get naked and have some fun, so I was trying to think of how else I might get a peek at what was under her nightshirt.

"This may sound weird," she started, finally speaking again, "but I'm getting this strong feeling that we're meant to make a connection tonight, that's why we're both awake but no one else is."

I was afraid that meant talking and sharing our feelings until she pulled her nightshirt up over her head. I'm sure my eyes went wide and my jaw dropped as I tried to take in her luscious tits, topped with large areolas and hard, thick nipples, and her trim, dark blonde bush. As she lay back against the end of the couch, I started moving, pulling off my t-shirt and slipping out of my lounge pants, my rigid tool springing out. She reached out her arms to beckon me between her spread legs, so I moved up over her and guided my tool into her pussy as she wrapped her arms around me. We both moaned softly as I slid easily into her; she was pretty snug, but extremely wet. I started to slowly fuck her while I brought my mouth to hers and we started to make out.

I could feel her tits pressing against my chest and wasn't going to let this unexpected experience go by without getting my hands on them. For the moment, however, I was content to slide my cock in and out of her sweet pussy and feel her tongue exploring my mouth. Karen and I had flirted a bit before but, although I thought she had a hot body, I also thought she was too flighty to pursue for any sort of relationship. I was perfectly willing to accept her flightiness, though, if it meant lying naked on top of her with my cock buried in her pussy. She was raising her hips up to meet each of my incoming thrusts and was obviously fully invested in her assessment of the reason for our sleeplessness. I wasn't willing to accept a mere fifteen minutes or so of missionary sex as the whim of the universe, however, so I didn't even wait until I felt the first stirrings of an orgasm before I changed things up. I figured if she questioned my actions, I'd just say that I had a strong feeling that it was what I should be doing.

I slipped my cock out of her and pulled my mouth from hers, but she didn't seem put off as I moved up to straddle her and laid my cock between her luscious globes. She squeezed them together around my tool and I started to slide it in and out of her soft, smooth cleavage. Fucking her had felt great and fucking her tits certainly didn't disappoint, either. I was looking down at her tits, admiring the freckled skin and thinking about running my tongue around her areolas and sucking her hard nipples, while her attention was focused on the head of my cock as it repeatedly peeked out of her cleavage. She seemed pretty engrossed in watching it and I noticed that she was running her tongue over her lips and occasionally opening her mouth as though to accept my cockhead, even though it wasn't coming that close.

I didn't want to deny her needs, since she had thus far indulged mine, so after I'd savored the feeling of sliding my cock between her tits for what I felt was an acceptable amount of time, I pulled it free and moved up toward her head. She let go of her tits and took my cock in one hand, guiding it to her mouth as the other hand caressed my balls. I moaned again as her hot mouth engulfed my throbbing tool and her lips started to slide up and down my shaft. I relished the feel of her mouth for a little while, but it didn't take too much of her stellar cocksucking before I was starting to feel the first stirrings of an orgasm. I certainly wasn't ready to be done yet, so I eventually withdrew my cock from her mouth before it was too late and moved back down between her legs, this time with my face right before her dark blonde bush.

It felt like we had done a lot in a short time already, and maybe it was just because I was overly anxious, so I decided to spend some quality time licking her pussy if she'd let me and hopefully bring her off as she'd come so close to doing for me. I kissed her smooth inner thighs as she reached down to run her fingers through my hair. I glanced up to see that her arms were squeezing her tits together and, even though I'd already fucked them, I was still savoring the opportunity to see what I had admired so often before; I made a mental note to also see how her bare ass looked before she covered it up again. I ran my tongue up her slit, tasting the abundance of pungent juices that was collecting there and causing her to moan softly. I smiled because it pleased me that something I was enjoying so much was giving her pleasure as well. I slowly ran my tongue up her pussy, tasting her nectar and causing her to writhe about.

When my tongue contacted her clit, she sucked in her breath, but I continued to lap at her entire pussy until I knew she was good and worked up before focusing on it. I slipped a finger into her and started to slide it in and out while licking, then sucking, her clit. She initially let out a moan that was a bit louder than she'd anticipated, so she put the corner of a throw pillow in her mouth as she rocked her hips toward my face. With the hand that wasn't holding the pillow, she held the back of my head as if to make sure that I didn't decide to leave before I'd finished the job. I had no desire to be anywhere else and was pleased that I'd been granted access to her sweet pussy, so I continued to enjoy eating her while simultaneously bringing her closer and closer to, what appeared to be, a pretty intense orgasm.

Her pussy was becoming even wetter and more engorged around my probing finger as her body also started tensing up. The pillow barely muffled the noise that slipped out when she started to cum, the tension leaving her body but several powerful shudders passing through it. I continued to lap at her clit as she came, her juices drenching my finger, then slipped my hand free and sucked my finger clean. As soon as she was able, I told her to turn over, which she did, her ass up in the air for me. I took the time to admire it, running my hands over it, kissing it and tonguing her asshole before kneeling behind her and guiding my cock back into her hot, dripping pussy. We both moaned again, careful to keep it low, as my cock filled her and my hips tapped against her awesome ass. I took her by the hips and started to fuck her, starting off slowly but, as she started pushing back against me, clearly still very worked up from her recent orgasm, I picked up the pace.

As I slipped my hands down to fondle her swinging tits, she reached back between her legs to stroke her clit as I fucked her. She was pressing her face against the couch cushion but I could still hear her moaning as she quickly approached another orgasm, right on the heels of the first. Her pussy felt heavenly sliding up and down my cock just as her tits did in my hands, but it sounded as though she was enjoying herself even more than I was for the moment. I moved my hands back up to her hips, thinking I could give her deeper penetration that way and, after a few full thrusts deep into her hot pussy, I felt her body tremble as she came once again. I continued to fuck her until I was sure she'd finished cumming, then pulled out and sat in the middle of the couch. She straightened up and moved around to straddle me, sitting on my rigid tool with her luscious tits right in front of me.

As she started riding up and down, I caressed her tits, gently tracing circles around her large areolas and stroking her thick, hard nipples. While her pussy felt absolutely outstanding, I sort of lost myself in her tits for a while after so much time of stealing glances at them wrapped in a tight t-shirt or sweater and now having them right there in front of me. My own orgasm was slowly starting to build up again, but I was raising Karen's tits so that I could run my tongue around her areolas and suck her hard nipples. As I felt myself getting closer to cumming, I ended up leaning back and watching her tits bouncing while reaching around to run my hands over her ass. I was pushing up into her, enjoying the increasing levels of pleasure I was experiencing thanks to her hot pussy. She must have been able to sense when I was about on the verge, because she stopped riding me, climbed off to kneel on the floor and wrapped her lips around my tool.

With one hand around the base, stroking as she sucked, Karen slid her hot mouth up and down my throbbing tool as I relaxed against the back of the couch, watching. She was a talented cocksucker, not just bobbing her head up and down, but doing whatever she could to draw the pleasure out longer, though I got the impression that this was not just for my benefit; she seemed to be getting as much out of sucking my cock as I was. I started to run my fingers through her dark blonde hair as I got closer to cumming, though I resisted pushing my cock any deeper into her mouth as she was doing an outstanding job of bringing on my orgasm without my assistance. My cock started to swell even more as I was right on the verge but Karen never let up, even as I exploded with a soft grunt into her mouth. She swallowed my load and continued to nurse my cock until I was completely spent, then let it fall from her mouth and smiled up at me.

"That felt right," she finally said, "what do you think?"

"I think that was absolutely outstanding," I replied, "the best remedy for sleeplessness I've ever tried."

"I think I can probably sleep now, though," she said, "but maybe we should stay together down here just in case we wake up again."

We got dressed again and pulled an afghan off the back of the couch, lying together under it as we finally drifted off.

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