FWB Ch. 01: Kaylee

It was the second week after graduating from high school and the parties, barbecues and other celebrations were starting to wind down. I'd been wise and had delayed starting my summer work schedule so I'd been able to attend pretty much everything without having to also squeeze in working. Surprisingly, I wasn't feeling burned out, but part of that was probably sleeping a lot and part was probably the fact that I didn't drink as heavily as some of my friends and classmates. I knew that there would probably only be a few opportunities once the graduation festivities ended to see such big gatherings of my classmates before we all headed off to college or jobs or whatever we had planned so I was trying to attend as many events and see as many people as possible. While I would be attending college, it would be locally, so I wouldn't be going away anywhere.

After seeing almost all the same people at most events, it was nice on this particular evening to see a familiar and friendly face that I hadn't seen in person in a while. Kaylee and I had known each other since we'd started preschool together but had only gone to school together through elementary school. She'd gone to a different middle school and high school but had also graduated a couple of weeks prior. This particular party we were at was being hosted by a mutual friend from back in elementary school so it was no surprise to see her there. We'd been in touch mostly through social media but I couldn't recall the last time I'd actually seen her in the flesh. We embraced, of course, and I realized that I liked feeling her body against mine and it wasn't just because, at eighteen, my hormones were running rampant. I momentarily wondered if, because she was eighteen too, her hormones were equally charged up.

We started catching up and eventually found someplace to sit but it wasn't like we were otherwise antisocial; we had a lot of people we knew join us at various times and each of us got up occasionally to use the bathroom or refill our drink or whatever. As the night wore on, there was definitely a contingent at this party, as there typically was at every party, who were getting as drunk as they possibly could. Mostly it didn't impact us but occasionally somebody pretty drunk would briefly entertain us. Eventually, though, as the crowd in general was starting to thin, they became less entertaining and more obnoxious. After we saw the first episode of puking, those of us who were still mostly sober started talking about leaving. When one drunk started to aggressively hit on Kaylee and I almost had to deck him, we were out the door.

I wasn't really feeling like there was any chemistry going on between us; the night had just been a nice reminder of what a great friend she was and why. Before we parted ways, we were talking about how we needed to get together a lot over the summer before she went off to college.

"I'm having such a great time hanging out with you again," she finally said, "why don't we just head over to my house and keep the night going."

"Your parents will be cool with that?" I asked.

"They're not around," she replied, "so I doubt they'll have any objections."

Again, there was no feeling at this point that something was going to happen between us. If she was thinking that, she was doing a great job of hiding it from me. It was just two friends going to hang out. We each got in our respective cars and I followed her, parking in the street in front of her house while she parked in front of the garage. It had been a while since I'd been inside her house but it didn't look like it had changed much. We went directly to the kitchen and I admit that, as I followed her, I took the opportunity to check out her ass. She was wearing a fairly short, flowery skirt that wasn't tight but it hugged her ass pretty well. It also showed off her thin legs and made them look longer. Her ass was definitely looking pretty nice but it still didn't cross my mind to put the moves on her. I did well enough with the girls and there was that saying about not taking a shit where you eat. Maybe that wasn't completely applicable but the gist was that it wouldn't have occurred to me to risk making an ill-conceived and likely poorly received pass, potentially turning a longtime friendship awkward.

We did a little snacking and made sure to hydrate, even though neither of us had drank very much at the party. It was kind of weird hanging around her kitchen in the middle of the night with no one else in the house; we didn't have to be quiet and she didn't seem concerned about keeping things neat. Eventually, she suggested we go hang out in her room instead, so I followed her down the hall and up the stairs. This time, as I was ascending the stairs behind her, I not only had her ass right there in front of me, but I could see a little more of her leg up under her skirt from below. Had I been invited up to the bedroom of just about any other girl, I might have reached forward and caressed the smooth thigh before me. The thought definitely crossed my mind but I managed to suppress it.

The décor of her bedroom was a bit more mature than it had been the last time I'd been up there, which was no surprise since it had been so long. What was a surprise was when she turned to me, threw her arms around my neck and kissed me. I was not so surprised that I didn't respond immediately, my hands going to her narrow waist as our tongues snaked into each other's mouths. My cock also became instantly rigid and I was initially hesitant to reveal this fact to her until it occurred to me that, since we were in her bedroom and she had initiated this, she shouldn't be surprised. I slipped my hands down to her ass and, as I caressed it through her skirt, I pulled her against me. My shorts were loose enough that she had to have felt the solid mass pressing against her abdomen. Despite being only eighteen, I was well aware that, if my cock was rigid, her pussy was probably dripping. I'd never really considered eating her pussy before but suddenly the thought was in the forefront of my mind. It wasn't going to happen standing there in the middle of her bedroom, so I picked her up and carried her to her bed.

We'd continued making out and she'd wrapped her legs around me so, once I'd laid her down on her bed, I was laying over her with my cock now pressing between her legs. I didn't intend for us to dry hump, mainly because I was afraid I might end up shooting off a load in my shorts, but our groins subtly started grinding together the longer we were making out. Fortunately, before things went too far, she rolled me off to the side then onto my back as she straddled me. She did start to hump the bulge in my shorts as she leaned down to slip her tongue into my mouth again, but only briefly before she started moving backwards down the bed. She went to work on getting my shorts open and I figured she was going to ride my cock with both of us still mostly clothed. To my pleasant surprise (once again), once she'd slid both my shorts and underwear down, releasing my throbbing tool, she knelt between my legs, took my cock in her hand and engulfed it in her hot mouth.

The moan that I let out left her no doubt that what she was doing felt absolutely incredible. Even more incredible was looking down and seeing her face down there with my cock disappearing repeatedly into her mouth. I propped my head up on her pillows so that I could watch her. She had a grip on the base of my cock and was gently pumping it as her lips slid up and down my shaft. Her long brown hair framed her face and she would occasionally look up, smiling around my cock. Despite being only eighteen, I'd had my share of blowjobs, some of them less than noteworthy, so I knew that Kaylee was a skilled cocksucker. I wasn't even thinking about how she had gained those skills; I was just feeling grateful for the opportunity to experience them.

In addition to her skilled cocksucking, the combination of the situation and the brief dry humping had my orgasm building rapidly. I absolutely didn't want to be done enjoying this spectacular blowjob but I didn't try to hold off cumming because I knew that my recovery time would not be long. While I was recovering, and to aid in that recovery, I intended to make her cum at least once if not more. In order to do that, I was guaranteed to get her at least partially naked and that in itself might be enough to have my cock stiffening again. In fact, just thinking about undressing her and seeing her naked had me right on the verge of cumming. My cock was swelling more the closer I got but she never hesitated. The pleasure just continued to build as she remained focused and when I grunted and started spewing into her mouth, she swallowed my load and continued sucking my cock. Only when I was completely spent and starting to soften did she release my cock and crawl up next to me.

"That was outstanding," I told her.

"Really?" she asked, "Good, I'm glad you liked it because I enjoyed doing it."

"Well I'm going to make sure there are a lot more things for you to enjoy tonight," I said and, as I started kissing her again, I ran my hand up her smooth inner thigh and under her skirt. She positioned herself so that she could spread her legs as I started to caress the front of her panties, feeling the coarse texture of her bush through them. She was starting to writhe just from that so I slipped my hand into her panties and over her trim bush. I found her pussy practically overflowing with juices and easily slipped a finger inside. I pumped it a few times as she moaned softly, then gently caressed her clit, which caused her to moan even longer and louder. She wasn't the only one with a bit of experience so I knew what worked well pretty universally to make the girls cum.

I was alternating sliding my finger in and out of her pussy with stroking her clit and she was rocking her hips as I did. We stopped making out when she needed to moan more continuously which was fine because I wanted her to be as focused on experiencing the pleasure she was feeling as she had been on providing pleasure to me. I noticed that her pussy was getting even wetter and seemingly more engorged the longer I was stimulating her which I knew was a good sign. When she started to tense up a little, holding me tightly, I figured she was right on the verge and just hoped that she was experiencing as much pleasure as it appeared. She stopped moaning because she briefly held her breath before letting out a cry as her body started shaking. I kept up what I was doing though I don't know if that extended her orgasm or increased her pleasure. Only once she had gone completely still and had let out a sigh did I slip my hand out of her panties. I tasted her juices on my finger which only reinforced what I was planning to do next.

"That was so good," she finally said, her eyes still closed.

"And that was just the beginning," I replied. Without giving her much time to recover, I got up on my knees and moved down between her legs. I pushed her skirt up around her waist then lowered my head and kissed her smooth inner thighs before starting to slide her panties down. She raised her ass then brought her legs together, pointing her toes toward the ceiling. I slid her panties off, tossing them aside as she brought her legs back down. Her brown bush was neatly groomed and trimmed within the faint tanlines from her bikini bottom. I could feel the blood beginning to return to my still-flaccid cock as I admired her pussy while lowering my face toward it. I kissed around her bush before running my tongue along her slit, tasting the pungent nectar that was accumulating between her lips. She moaned loudly and ran the fingers of one hand through my hair while the other hand gripped the comforter.

I slowly lapped at her pussy, slurping up her juices, before slipping a finger into her and licking her clit. She surprised me again when she gasped and her body started to tremble but I didn't stop; my goal had not just been to make her cum. I continued fingering her pussy while licking and sucking her clit as she came and after she'd finished. Although making her cum was one of my goals, the primary one was to provide her with a significant amount of pleasure. I'm sure that first orgasm was pleasurable but I knew that I could help her feel even more. Of course my efforts weren't entirely selfless, however; as much as I loved eating pussy, I really loved eating a new pussy. While I'm sure there had been times during our friendship when I'd considered what Kaylee might look like naked, I don't know that I'd ever thought about eating her pussy. So this was pretty exciting for me, too, having her skirt pushed up, her panties cast aside and her trim pubes tickling my nose.

She started rocking her hips toward my face while going back to moaning as I continued to devour her. This time I could tell she was building toward another orgasm because she was gradually starting to tense up. When she finally went limp, her body started shaking immediately as she came again. Of course I didn't stop this time, either; I continued eating her pussy through this orgasm and even through one more before raising my head and slipping my finger from her pussy into my mouth. My cock was nearly hard enough to roll on a condom by that last orgasm, which was by no means her last orgasm. I straightened up on my knees as she was catching her breath and finally removed my shirt so that I was completely naked. The next thing I wanted to do was to get her in the same state, which I knew would get my cock fully rigid.

I took her hands and pulled her into a sitting position as I sat back on my heels. I reached for the bottom of her blouse and pulled it up as she raised her arms. My focus was on her bra as I let her blouse drop off the side of the bed. Her hard nipples were pressing out so I ran my hands over them before reaching behind her to unfasten it. This put our faces close together so we kissed briefly then I slid her bra down her arms. Her tits were on the smaller side but perky with hard nipples that I couldn't resist leaning down to lick and suck. She moaned and ran her fingers through my hair as I stimulated her nipples with my lips and tongue. When I straightened up again, we kissed some more and I caressed her tits and nipples with my hands.

All that was left was her skirt, which I wasn't sure how exactly to remove. I didn't think there were any fasteners so I thought it would just slide down and I ended up being correct. It had an elastic waist so, as I grasped the hem and started pulling, Kaylee lifted her ass up and the skirt came right down. She looked great naked and I was correct that my cock was fully rigid again as I gazed upon her bare body.

"Do you have a condom or do you need me to grab one?" she asked.

"I've got one in my wallet," I replied, looking around for my shorts. Spotting them on the floor, I stepped off the bed, grabbed them and found the pocket with my wallet in it. I took my wallet out, extracted the condom and, after dropping my wallet, tore open the wrapper. I rolled it over my cock as I turned back to the bed but Kaylee was not lying on her back in the middle of it.

"You get to be on the bottom," she said, kneeling off to one side. I had no issue with that and thought, in fact, that I could probably last even longer if she was on top. I was still checking out her naked body as I climbed onto the bed and lay in the middle. My focus did not waver as she moved to straddle me and guided my cock toward her pussy. We both moaned as she lowered herself onto it, her snug pussy gripping my rigid tool. She sat there for a moment as I continued to admire her physique while relishing the feel of her hot, snug pussy. Eventually, she started to move up and down on my cock, slowly at first but gradually increasing her pace. My hands started out resting on her thighs then moved up to her waist as I watched her tits slowly bouncing. Of course they found their way around to caress her ass as it moved up and down which felt even nicer in my hands than it had looked through her skirt.

The feeling of her pussy moving up and down my shaft was absolutely incredible even through the condom. I was savoring the pleasurable feeling because I knew, despite having cum once already, that I wouldn't be able to last very long. I hoped I'd be able to help her cum again before I did and, based on the sounds she was making already, I thought it might be possible. She was moving up and down on my cock, her hands planted on my chest, as I continued to caress her ass while watching her tits bouncing. When she leaned forward, planting her hands beside my head, this put her tits closer but, as she was moving forward and back now on my cock, they were swinging more than bouncing. I brought my hands around to caress them and pushed up slightly each time she came down on my cock. I could feel my orgasm building more quickly, in part due to this subtle thrust but mostly because, the longer we were fucking, the hotter and more slippery her pussy was feeling. When she pushed back and stayed there, my cock fully embedded inside her, then shuddered while gasping, I was pleased to have helped her cum once again.

With the self-imposed pressure of getting her to cum before I did removed, I was focusing more on my own pleasure when she started to move up and down on my cock again. I was pushing more deeply into her each time she came down while also savoring the pleasure provided by the increased lubrication resulting from her orgasm. Fucking her felt absolutely fantastic even with my cock wrapped in latex so my orgasm was steadily building the longer she was riding my cock. My hands were back on her ass so that I could sort of pull her down as I pushed up into her, giving her as much of my cock as I could. I was watching her tits swinging with an occasional glance up to see the expression of pure pleasure on her face. I was happy to share this mutual pleasure with her but, as my cock was swelling even more as I approached my orgasm, I was not expecting to be able to help her cum again.

I'm not sure if it was because my cock had swelled even more right before I came but, as I finally started to spew into the condom with a moan, before I'd finished cumming, Kaylee let out a cry and I could feel her body trembling. I continued thrusting into her for as long as I could and, by the time my cock was starting to soften, I was certain that she'd finished cumming. She climbed off of my cock and lay beside me, catching her breath.

"I'm so glad we did this," she finally said, "It's going to be a fun summer."

When she'd recovered enough, she took the condom and wrapped it in Kleenex while handing me a few to clean off my cock. She tossed the condom in her trash can then shut off the light and we snuggled in her bed, quickly falling asleep.