This took way too long to finish, and it's a little short -- I blame a new job, life, etc. It'll probably be another two or three parts until we reach the initial introduction. I make no promises on the time frame. (My apologies in advance -- work sucks, eh?)
Where were we? Ah, yes, I'd left off right after my sister walked in on me at a very inopportune moment. Sam hung around a while longer that night before heading home. I didn't see Kimmy again until the next day, she went to bed early and Sam left a bit late. Now that my orgasm-induced indifference had faded and I'd had more time to reflect I was feeling increasingly embarrassed at being walked in on. Sure she should have knocked, but that didn't absolve me of awkward feelings about my sister seeing my naughty bits, especially when they were so assiduously demonstrating their function.
I could have let things play out naturally and gone through a few weeks of awkward conversation and averted gazes, but that just seemed stupid. So she walked in on me, big deal. I wanted to thank her for sending Sam my way and I was going to do it, awkward or not.
When I came down to the kitchen the next morning Kimmy was sitting at the table with a bowl of cereal. She looked up at me as I entered the room but looked away just as quickly. She was wearing a rumpled flannel robe and her hair was a mess, not that I was one to judge, I didn't look any better in the morning.
"Hey," I said, sitting across from her.
"Hi," she said, pushing grain puffs around in her milk with a spoon. She still didn't meet my gaze.
"About last night..." I started.
"None of my business," she said quickly.
"Well... yeah, but... um, alright, I'll say it, I'm weirded out. And... I'm sure you are too, so... sorry? Can we pretend it never happened?" I asked hopefully. At this she did look up at me.
"That's… really not something I'm going to forget," she said.
"Damn," I replied.
"Damn," she agreed.
"You're not traumatized, are you?" I asked.
"Oh shut up," she said, giving up on the last few pieces of cereal and indelicately slurping milk from the bowl.
"What? I can't be a concerned brother?" I protested.
"Maybe, except that you would be the one that traumatized me," she said as she set the now empty bowl down.
"Was it as bad as all that?"
"No... it's just, well that was the first time I saw a guy... you know. Well, in real life anyway," she said, her gaze avoiding mine once more.
"Ah," I said, wondering what I could possibly say to that.
"Really, I'll be fine, don't worry about it. I'm glad you and Sam hit it off... I meant that non-sexually," she quickly amended.
"No, yeah, I got that. I wanted to thank you, Sam is nice. Honestly, if it weren't for you I'd be dateless and a social outcast," I said.
"Whatever, you would have gotten a date, I was just helping Sam," Kimmy said.
"Deny it all you like, it's true. This time three weeks from now I'd be living in a cave wearing nothing but a dirty loin cloth. You saved me, you have my eternal gratitude," I said and grabbed her hand earnestly.
"A loin cloth? Well as long as you have something covering your junk."
"Now, now, it wasn’t that bad. For a first... seeing you... it wasn't bad," she said. Before I could even begin to think about how to respond to that statement she got up and put her bowl in the sink. After that she headed back upstairs without so much as a backward glance. I reached up and closed my hanging jaw. Maybe I was the more experienced one between us but she certainly had a way of leaving me at a loss for words.
The next couple of weeks passed without any new major incidents. Sam and I had a couple more dates as time allowed, though they were far more traditional dates as far as that went. Certainly not in my bed, that was a special kind of first date. Something told me that she was holding out and trying to keep my interest, which was fair enough, I wasn’t going to press her.
The dance loomed large on everyone’s minds. Desperate last second plans were being formed and dashed wherever I looked. Those without plans declared themselves by the way they moped about. Kimmy, unfortunately, was among the dateless. I was honestly surprised by this. Yes she was my little sister, and yes she could be annoying, but from an objective view point she was attractive. And as much as it galled me to admit it, she was also smart – smarter than me if grades were anything to go by.
After she’d set me up with Sam I’d been determined to return the favor and find someone to take her. Maybe I couldn’t come up with something on the same romantic scale, but at the very least I wanted to get her an arm to hang on as she strolled onto the dance floor.
Despite my best efforts, I failed to find a single friend who would take her. It wasn’t that the guys disliked her, it was just that they had dates already. I was short on favors too, so I couldn’t even strong arm someone into a last minute date change.
It was Wednesday night, the last week before the dance. I’d been at school late working on a group project for my American history class. My backpack thudded as I dropped it in its customary place by the door. Two flicks sent my shoes rolling next to my bag and I climbed up the stairs two at a time. With a socked foot I nudged my bedroom door open.
I stopped dead in my tracks. Kimmy was sitting on my bed. Crying. Man, you hug your sister once and suddenly you’re a shoulder to cry on. Her hair was wet and its curls had tightened in to sleek dark red spirals. A fluffy pink towel was all that covered her.
At the sound of the door opening she looked up at me. Her eyes were red and puffy. I sighed and all my annoyance fled. Sometimes you’ve got to be a good brother and this was one of those times. I sat down next to her.
“Nothing…” she said unconvincingly while trying to stifle her sniffles.
“Says the half-naked girl sitting in my bed crying.”
“I’m not even a quarter naked, jerk. And I’m not crying.”
“Now you’re just in denial. Unless you’re wearing a flesh-colored leotard I’m pretty sure you’re a good way towards naked,” I said while prodding her towel. “And you’ve still got tear streaks on your face…”
“I…” she faltered and then put her arms around me and cried some more. Well, so much for cheering her up. I really needed to work on my routine.
“I still don’t have a date,” she said between sobs. “Why don’t boys like me?”
“Whoa, slow down,” I said. “Not getting a date doesn’t mean boys don’t like you.”
“Well what does it mean, then? I tried so hard…”
“Hey, stop that, we’ve been over this. If they don’t ask you out, it’s their loss. Remember? Perfect boobs,” I said pointedly.
“Ugh, I hardly even have boobs. Maybe that’s my problem.”
“Boobs aren’t everything,” I said, though I doubted the words even as I said them. Granted my perspective as a sixteen year old male probably wasn’t the most worldly, but that didn’t stop me from speaking such profound wisdom.
“Yeah, right, that’s all you guys care about,” she said accusingly.
I raised my hands in supplication. “Don’t attack me, I’m not even on the market, I have sibling immunity.”
“Whatever, you’re still a guy, and just look at these!” she said with disgust as she yanked down her towel, revealing an admittedly small pair of perky breasts. Despite their size, they were perfectly tear drop shaped with small pink nipples. I think at that point my brain stopped working. There was some massive disconnect going on where half my brain was completely absorbed in staring at the live, soft breasts hovering so close and the other half was desperately telling me to look in another direction because those breasts were clearly my sister’s. The breast loving half, of course, held sway and I continued to stare.
“See?” She said and hiked her towel back up. When I didn’t respond, still waiting for my brain to reboot, she prepared to storm off. Before she could I grabbed her arm.
“No,” I said.
“You were right, you do have perfect boobs,” I said solemnly.
“Oh, shut up. I don’t want your pity,” she said.
I shook my head vigorously. “It’s not pity. Perfect boobs. Really.”
She sat back down and hugged me, thankfully not crying this time.
“Now if only all the boys at school knew that,” she said wistfully.
“Well, we could take pictures…” I said, already bracing for the smack I knew was coming.
“Shut up,” she said as she slapped my arm, but she continue hugging me, only now I was very aware that only a thin towel was separating her breasts from my arm. “And the only guy I have staring at my chest is my brother, what’s wrong with that picture?”
“Well, they’re covered back up, for one, that makes it really hard to stare,” I said.
Kimmy stood up and stared at me, the crying girl had vanished and my cocky, somewhat annoying sister had returned.
“Oh please, you get a hand job and suddenly you’re some smooth operator?” She pulled her towel down so that her breasts popped out again and straddled my lap. “Trust me,” she said, “you wouldn’t know what do with them.” Her breasts were only inches from my face, I swear I could feel heat radiating from them.
I don’t really have a defense for what happened next, all I can say is that I was sixteen years old, and boobs. Before I knew what I was doing I had wrapped my lips around her left nipple. Kimmy stiffened for a moment but then cradled my head, pulling me closer. I kissed from left breast to the right, exploring every inch of her soft, pale skin. She gasped as I sucked on her right nipple.
Not to be outdone, I felt her reach down and grab my stiff cock through my jeans. My lips found hers and we kissed. I felt her fumble with my zipper and suddenly my cock was free and in her bare hands. She stroked me up and down. I ran my hands under her towel and grabbed her ass. The towel was bunched up now and I got a view of her shaved pussy hovering above my lap as she rubbed my cock. She kissed down the side of my neck, biting lightly. I gripped her hair and kissed her deeply, my tongue twining with hers. She reached her other hand down and began rubbing her clit.
As we kissed I could feel her breath grow ragged as she rubbed herself, and my cock, more vigorously. She broke off the kiss and put her head against mine, moaning softly as she shook with an orgasm. It was more than I could stand, my cock grew rigid in her grasp and I gasped as I came. I looked down to see a spurt of hot cum shoot over Kimmy’s hands and pussy. She kept stroking until I finished and then got off my lap. I could see beads of cum running down her thigh.
I didn’t know how to feel about what had just happened. I mean handjobs were a good thing, but there was the whole sister aspect, not to mention that I felt a little guilty about Sam. Kimmy didn’t say anything, though, she gave me a peck on the lips and went back to her room.
Sometimes you have to be a good brother, I had no idea what that meant anymore.