That Empty Feeling

WARNING: Ridiculous amounts of cum and possibly hilarious cum physics are present in this story. If you are offended or dislike these, then I may right a more normal one soon.....or if it's just too arousing for your health. YOU HAVE BEEN WARNED (also might make a more exaggerated version if I get requests). Also this is INTENDED to be part 1 but there might be a pt2

For those of you who want to get right to the story, skip ahead but here's a bit of background on the characters for anyone who likes it.

*

Alex: 22

A regular guy but clever, intellectual and maybe a bit weird.

Also sweet and kinda shy but knows that he doesn't have to let others know he is. A small secret he keeps for "reasons" is that he sees and hears EVERYTHING around him (thanks to great hearing and strangely wide vision)

Jackie: 25

Alex's oldest sister and the softer of the two. She can be tough when

she has to but normally she's soft like melting ice cream and just as sweet. Smart as well but only book smart and almost innocent (barely more common sense than a little kid). Also a real hottie, that Alex has wanted to bang for the last 5 or 6 years. Of course, so did every guy and girl around. Even the "straight" girls probably have wet dreams over her.

Jordan: 23

The younger of the two sisters and only a few months older than Alex.

She really does act older than him but not exactly as smart. Not dumb

by far but more street smart than her siblings. Not nearly as soft as

Jackie and acts like a guy really, so Jackie and Alex almost forget that Jordan is still a girl. She's much more into sports than her book worm brother and school focused sister but knows her way around a classroom, too. Not like that dumb cheerleader that always has a "conference" with

the principle and nearly every one of her male teachers. Well rounded in general you could say but not as round as those huge tits and that ass is amazing. Any hotter and she might literally cause car accidents.

Now, on to the story

It was the middle of the day and everyone was really just chilling out. Kids still in school and most of the adults are using up the time they have left on relaxing, before the little monsters come running. I'm in my room as usual (I'm Alex by the way) and doing something even more usual for me, A BOOK! And a good one too. Jordan is away, being a guy again and by that I mean beating guys at basketball, because they can't take their eyes off her tits jumping around, as she runs. The ones who can't see them are fully caught by her ass, so everyone has to fight to keep it from jumping out of their shorts. To make matters worse (for them), she actually has serious skill and great fitness that gives her an advantage over almost anyone on the court. After the game, Jordan has to rub it in and says

"If you spent as much time balling as you do eyeballing my ass, you might have a chance." Before putting a jacket, very carefully around her waist, just to make sure it denies them the pleasure of watching her ass get farther and farther away. Back at home, my other sister (Jackie) is listening to music and walking around the kitchen, half naked. Kind of a 50/50 chance on her being fully dressed or not, but my door is closed and a book in front of me, so I have no idea what I missed at first. That is, until Jordan gets home and her first words alert me.

"Put on some damn clothes". At that moment I carefully (to avoid detection) bolt to my door, to see what she's wearing (or rather what she's not) and get a glimpse of her in nothing but some light blue panties and a t-shirt that shrunk a little in the wash. Not my proudest achievement, but I regret nothing! And I refuse to let myself forget that it was my hard work that got it to shrink just enough but not enough to be uncomfortable and gave me such a heavenly view. I'm not worried about being seen because I'm upstairs and looking through a gap in the banister, which I thank the designers for adding, and she could only see my face if she looked, but I have the perfect angle to see her. Dark brown, almost black hair. A slender figure that's a bit smaller than I would normally like, but she makes it so sexy. Long and smooth legs, nice and firm ass. Medium size and not perfectly round but still nicely shaped. Her breasts are about a handful and sag ever so slightly (pretty sure you can imagine why). Not perfect at all but no part of her isn't good and her face brings it all together. Her face is smooth and soft, with a motherly touch that makes you want to hug her (and then fuck her). A smile that lights up the room and a frown that makes you want to beat, whoever made her sad. Even her voice, soft and loving but womanly, in a way that only adds to her softness. In all ways, she is an angel.

One look at her gorgeous body had me ready to run down the stairs and take her, even with my other sister watching. Of course, me being shy and smart, I wait until the right time and when they're together is NOT a good idea. Instead I just listened to them chat about Jackie not wearing enough (much to my pleasure) and Jordan beating everyone, as usual. From listening to them talk, I learned that they've both been without any good action in months and Jackie being the horny one gave me the beginnings of a bad idea. She also happens to be the most open minded, so all I have to do is wait until she gets horny and that's not hard to know at all, given her open admittance that she's horny. I continued to listen for any disturbances that may stop me and all I heard was good news. Jordan would be either gone or asleep most of the time for the next two weeks, due to basketball practice and other athletic activities that take a lot of time and energy. Not to mention, she has to study for her college entrance exam, BUT Jackie would be home with me a lot. Now that I had all the information I needed, I stayed out of sight until the conversation ended and when Jordan came to see what I was doing, I decided to see what would happen if she saw me with a raging boner. So I was already lying in bed on my side, with a book open next to me, so it was obvious I had fallen asleep reading. The one thing out of place was my dick on my thigh and sticking about halfway from under the blanket. I tried to lay there and do nothing but breathe and I was pretty surprised when I felt the cover coming off of me.

Did I just not put it all the way on my bed or was she pulling it? To test, I just moved a tiny bit and suddenly the cover stopped. Now I was certain she did it and as it came past my waist, I was suddenly self-conscious about what she would think but I still didn't move and soon heard her speak.

"Wow that's big" she whispered and just stood there a moment, probably in shock. Again she spoke and said "She won't believe this until she sees it herself."

Of course I was overjoyed by hearing that and all I could think for a moment was "JACKPOT" and wanted to get up to see the look on her face but I had to be patient. It was getting hard to keep pretending so I faked waking up a little and heard a panicked step away from my bed. "Just a little more and she'll leave" I thought but before I could do anything I felt her pull the covers over me again and kiss me on the cheek. While she does this I'm kinda thinking "weird" I mean she can be caring toward me but sweet and gentle? Maybe I got their voices mixed up?

"Jackie has to hear about this." Is all I heard, as she silently crept out of my room and closed the door a little more than I had left it. For a while I tried to lay there in case she actually didn't leave and when I couldn't anymore, I got up and stretched to look around. Empty, save for me and my belongings. Guess I'm not getting any tonight, but that was totally unexpected anyway. I got up and went over to my desk to get my laptop and just remembered that my dick was still hanging out.

"Oh what the hell!" I think, I mean I'm alone and Jordan already saw it so no need to hide now. When I sat down, I turned my laptop on and was very grateful that I have Windows 8 so no long startup time. It was time to get started and I had to do it all carefully, so my intentions wouldn't be exposed until the right moment. I took a deep breath and let out a happy sigh, then I said to myself

"First order of business, start my list of temptations and wait for her to fall into the first trap." Which I immediately scolded myself for saying out loud and with me being paranoid, I had to look into the hallway and see if anyone heard me. Luckily they were both asleep and I was embarrassed with myself for not thinking about the fact that I knew Jackie was asleep before and just heard Jordan get in bed. At that point I had to quietly punch myself for being careless and could only say "real smart Alex. Almost got yourself caught." But of course I was careful to be quiet this time. Now I sat down at my desk again and started a new text document to keep my plan for tempting Jackie.

1.Misplace something near her dildo, something I gave her and that should be enough to get her thinking about me and sex at the same time.

2.Ask a few inexperienced little brother questions, about sex and what I have to do to be good at it.

3.Casually bring it up again and shift it to her experiences.

4.When a few bad ones come up, simply tell her how I would do it different.

5.Give her a few days to let it set in and to help it along, let her catch me jerking off or watching porn.

6.Last, when she starts getting more open to it, give a little suggestion about "demonstrating" something.

After that, it's all up to a bit of luck and serious need of a good fuck, from a guy with a big dick. I'm not full of myself but I know I have a big dick, so if she sees it then I can remind her later, somehow and she'll be mine when the wetness hits. Now it's time to put my plan into motion. Although she happens to be asleep so I better wait until morning.

The next morning I waited until Jordan was almost ready to leave and came down, only to eat breakfast with her and Jackie, but I did take a few minutes to really wake up. Once she was out the door I shyly turned to Jackie and told I had a question to ask. Of course I was being shy on purpose but also kinda nervous at what might happen and her reply relieved me.

"What's up little bro?" she asked and gave me that totally innocent look that says she has no idea what to expect but trying to figure it out (always failing badly might I add).

At that point I could only say "it's about sex" and try not to stutter. She was always cool and open about most things so I half expected a response like

"Uh oh, what is it?" and a worried look, but instead she said "you can ask me anything you want." With my plan in my head, I could not pass up this opportunity and decided I can rearrange it a bit if I have to or maybe skip steps if it goes faster than I think it will.

"Ok then, have you really had much sex? I mean I don't want to ask stupid questions and I really don't know what you have done." I heard her having sex a few times but I honestly didn't know what went on in her bedroom and I wasn't exactly having enough to know a lot about sex myself.

"Lol plenty." I like it when she speaks in text, like I'm reading the words. It's cute to me and she knows it, but I had to keep my goal in mind so I quickly asked

"can you tell me what to do, in general?" no surprise at what came next.

"Well what exactly do you want to know other than make it feel good? There's a lot to know and I know you read a lot so you have to know something already." Followed by "Are you a virgin?" and I almost couldn't answer but honesty was best here, so I said

"No, I've had sex but I don't think I did that well and she definitely didn't have an orgasm." Jackie must have known I was a bit insecure because she swiftly said

"Most guys can't just fuck a girl to orgasm on the first or second try".

"So what am I doing wrong? How can I make my girl cum? I mean, when I actually have a girlfriend." I said and then her swift, experienced answer

"Well you have to get used to her. What turns her on, what turns her off, what to touch that makes her scream, like fuck me harder and don't stop".

"Honestly you're giving me a solid erection" I said back, which I meant for sure after hearing her say that.

"Sorry bro, I get too into it when I talk about it sometimes" was her answer but I really hadn't thought she would be into it at all. I had to know how serious she was so I asked

"do you really like talking about sex?".

"YES!" was the first word from her mouth and I imagine a bit more excited than she meant to sound. "I mean yes but you know it feels good so I get excited when I talk about it and start thinking about getting some" she said, clearly blushing. At this point I'm comfortable and ready to speak freely (mostly) and I relax in my chair, before an idea hits me.

"Want to finish our conversation on the couch or in my room? I want to get comfortable" and she agrees, so after she gets up and heads toward the stairs, I follow, waiting to get a great view of her ass but she catches me by the first step.

"Oh no you don't, I know you want to watch me going up the stairs. You first" and of course I had to do it or risk ending the moment, so up I went and then realized that she's 5'6 and I'm 5'9 so I get a good look at her ass from only a few steps below her and that means if I get a step or two more ahead of her then she should be able to see the way my pants move, when my dick swings as I walk.

Sure enough, I heard her say "dang" under her breath and when I asked if she said something, she looked up quickly and said "nope". Guess I already got her attention.

By the time we got to my room, I just got careless and loose, knowing it would go nicely from here if I just act natural. I flopped on my bed without thinking about it and she walked in behind me, just as I hit the bed, so she saw my cock bounce under my thin pajama pants and her face showed her surprise.

"You sure you don't want to cover that?" she said and I looked down at my bulge to see how obvious it was.

"Only if it bothers you" I said and she obviously had to consider her answer first

Then she said "No I'm fine" but never fully looked away from my throbbing member and the attention was certainly keeping it at least half hard at all times. So to get it going again, I asked a simple question

"So what's it feel like to have a guy shoving his tool in you?" and she nearly burst into laughter at my wording but went along with it and said

"To be honest it's been so long I can't even think about tools. I need power tools to handle this." and I'm fairly certain about what she means but my curiosity would kill me for not asking.

"I think I know what you mean but tell me anyway" I said and she told me the solid truth

"I need something big and hard in me and I don't want to get a boyfriend then fuck him a week after we meet, but this is killing me". I wanted to really lay it on thick, so I asked her about the size she meant, but with a great excuse.

"I'm kinda wondering if most guys are bigger than me." I say, sounding rather serious about not knowing

So she tells me "They are not as big."

I pretend to be skeptical about her opinion, but full well knowing the truth about my size. "How do you know if you never even saw mine?"

"Bro, you know......fuck it, I know you don't believe things like this without proof. Pull your pants down."

"Really? That's not weird for you, like it is for me?" I said and half meant, but she knocked the idea of it being weird right off.

"You're talking to your sister and asked about what I want inside me. You made it normal already".

Which I had to admit was true so "good point, there's no use being shy now" and with that, I stood up, put a little pause in like I was deciding and before I moved Jackie said "just pull them down already" and I complied instantly.

A swift and somewhat shocked "O M G. It is huge" came and I had to honestly question now.

"What? You say that like you heard it from somebody". And the look she gave me, straight up said she was busted or I figured out a secret she was supposed to keep.

"Yea, Jordy (our nickname for Jordan) came in your room last night and said she saw you sleep, with that big ass dick almost hanging off the bed". She said and I didn't know when she said it but I found out pretty soon, that Jordy said it at breakfast, when I was getting ready to come down.

I questioned "Big ass dick? Haha is it really?" and I knew it was but she gave an answer that threw me off a little.

"Uuuuh YEAH, duh. That is a power tool and you better be careful not to hurt anybody with that. Especially not me."

Now she had given me the idea that I didn't have to convince her to have sex but care was still needed and I almost shot myself for answering before I thought about that. "So what are you saying you want me to be gentle?" I asked and she said

"Mhm". Then my second question for the moment

"On you" raising an eyebrow as I asked.

"Oh um I did say that, didn't I?" which was pretty evident now and I couldn't hold my laugh, as I fell backward onto my bed, loudly saying

"Yea you kinda did, but that's none of my business". In response to my tease, she got up and flashed her tits, to shut me up (worked pretty well). When I got back to reality, I had to mess with her so I grabbed my "power tool" and waved it at her, saying "you're just jealous that I have this all to myself."

Then in one swift motion, she dropped her shirt over her boobs and slapped me right on the head. I knew she would but she got the head I had no clue was in danger and it stung badly too. She gave a little "oops" and covered her mouth. I sat there holding some four letter words at bay and she kissed me on the cheek. "Sorry baby bro, I really didn't mean to hit you there"

With that, she ran off to the bathroom. After a moment she came back with the softest towel she could find and pulled my hand away, to gently rub the head of my aching cock, with a towel I now noticed was wet with cool water and I instantly relaxed.

While she was rubbing she said "I only did this because it was my fault but I'm not about to play with it and I don't think you will for a while". She was right, it still hurt a little but she did help the sting go away.

Now it was about noon and we continued our talk but she told me "be careful you don't get hit again" and I sure was careful. She may be just about harmless normally but will not tell a lie for no reason, so she can step past that when it comes to backing up a threat that she really intends to be idle. After that, we decided to watch a scary movie together and it started getting colder outside before we noticed. We ended up just talking about movies, which went on for a few hours and we both fell asleep for about 3 and a half more.

In Chicago the cold can hit faster than a bullet and without the heat on, it was creeping through the house until it hit us so hard we instantly grabbed a blanket and cuddled on the couch, while we watched our movie. After that one, we were in a joking mood so we put in "Scary Movie" as a joke on having just watched an actual scary movie.

Just as it started, Jordan walked in and Jackie screamed "JORDYYYYYY!!!" as she hopped up, across the room and instantly onto her sister, like a little kid welcoming mommy home and it was fucking adorable.

Jordy being such a tomboy just held her up and looked at her, saying "what you want little girl?" with a stale and sassy tone but even more stale look on her face. That moment forced me to jump over and turn that odd sibling hug, into a family dogpile.

None of us know how but Jordan basically became our temporary mom, while the real deal, Susan was out of town and staying with my aunt. After talking about her day and a bunch of crazy things, we finally got up and watched the movie, which had us all dying laughing. After the movie, we were all tired and didn't feel like moving so we all slept where we were. Me in the middle of the couch, with my arm around Jackie who was cuddled up to me and laying with her head on my lap. Jordy was leaning back, flat across the couch with one leg over the arm of the couch and the other on the floor.