This work of fiction is mine and is not to be copied without my permission, first time writing a story please keep comments positive or constructive, I don't condone incest which is why this is a work of fiction so please don't call me a sick pervert I have no control over what gets me horny and I can safely assume that neither do any of you. Be warned this story contains incest, anal, watersports, and enemas if none of this is your bag or any of it for that matter press back now, you have been warned.
Now lets start with looks thats how all of these start right, Anyway I will start with me, Jack, first I am 16 years old, 6'2'' and about 180 Lbs a little on the muscular side with a alright sized dick at 7 and a half inches but I have a good girth to it, I like to keep it well trimmed down there cause I figure if I like it on a girl they probably fell the same way basically I am as average as one guy can get even in the looks department just plain average.
My sister Carrie on the other hand is a knockout by anyones standards, 19, 110 lbs when dripping wet, about 5'7'' I think, and a perfect set of 36C tits (yeah I checked her bra who wouldn't) and when I say perfect good lord do I mean perfect I accidentally walked in on her in the shower once and they were perfect, her ass is also a great assets to say the least(if you have ever seen here in tight jeans you would agree).
Now lets get to the damn story already, It started on Christmas vacation me, my sister and my parents always go to our cabin for Christmas vacation for as long as I can remember, and it is a pain let me tell you, 4 hours in a car with my bitchy sister will make anyone in their right mind consider killing themselves or her, The cabin is nice though once you get there, its very private, one road in and out and its surrounded by endless forest the newrest town is a 30 minute rive in good conditions and we had been lucky every year going there to never get snowed in…&hellip.well till this year at least.
So after the "lovely" 4 hour drive we get there and are unloading the car, and my dad was already peeving out on my mom and soon enough it was just me and miss happy unloading the car so I tried to start up a conversation with her, God knows why I knew how it would end.
"another year in this crappy place huh carrie." I said "what the fuck climbed up your ass and died Jack, mom and dad go through a lot to make out here every year" Carrie "cheerfully" replied "fuck you,I know you hate coming out here just as much as I do don't try to pretend that you are on some saintly level above me" I shot back "whatever unload the car yourself asshole, I have to use the restroom anyway" she said and walked away "you know why you have to stay in the bathroom, is because you are so full of shit you know right" I yelled at her back as she walked into the cabin.
side note she does spend a long time in the bathroom, but only because she suffers from constant constipation, no one knows why my mom and dad have taken her to a few doctors and they all said basically the same thing, "she is normal as far as we know, but if she has trouble going she will need to take stool softeners or in extreme cases she may need to receive an enema to loosen her up." I finally finish unloading the car after 2-3 hours and not ten minutes later Cassie comes into the room and starts grabbing at the bags, at the time I figured she was going to start helping me put groceries away and seperate everyones stuff out to the correct rooms.
"thanks Cassie I am pretty beat after unloading the car, I am sorry about what I said I didn't mean it" I heartfully said in thanks. "fuck off Jack I am just getting my stuff then you are on you own you little shit" she responded as she started ripping the bags apart Boy was I wrong about that whole situation. "Jesus Christ Cassie what the fuck leave the bags alone its going to take long enough to get everything put away" I yelled at her.
"where is it, where the fuck is it." Cassie said to I assume herself. "what the fuck did you do with the rest of the bags Jack" "Those were all the bags in the fucking car Cassie if you don't believe me go check for your fucking self" I replied angrily "Whats missing I will fucking look for it when I put everything away" "Don't bother you are a fucking idiot and wouldn't be able to find it anyway you asshole" She stormed away as she said the last statement Anyway another couple of hours later after unloading everything my mom and dad finally emerged from their room freshly showered from their love making and my sister was already at my moms side, I assumed telling on me like the bitch she was, after a few minutes of hushed conversation my mom leans over to my dad and says "honey we need to run to town Cassie forgot something" "Alright looks like supper is up to you Jack." my dad says "what the fuck I just spent all day unloading for miss prissy and now I have to fucking cook for her too, this is bullshit" I angrily replied "fuck you Jack you should be happy to cook for me I am…&hellip." Cassie never got to finish her statement as my dad started yelling&hellip.
"thats enough both of you we will be back in an hour we will just bring something back and you guys can warm up your own suppers" Not even 30 minutes after they left the snow started falling and when I say falling I mean it was fucking coming down and even that might be putting it lightly. I then received an expected phone call from my parents telling me they were stuck in town and might not get back tonight and more than likely they would be stuck in town all week from what the forecast was telling them, they told me not to worry if the power went out they had the emergency generator stocked with gas before we came up and there was enough to last the storm.
So I begrudgingly climbed the stairs to my stairs to tell her the bad news I knocked on her door and received no answer so I opened the door and saw she wasn't there, I heard a noise from the bathroom so I figured she must be in there.
I knocked on the door and said&hellip.
"Cassie mom and dad just called they are stuck in town and can't get back tonight or at all this week from what the weather man is saying" "GODDAMMIT JACK!, give me some fucking privacy for fucks sake, how did you know I was even in here" I heard yelled from behind the door along with some shuffling "Jesus Cass I just wanted you to know mom and dad wouldn't be back and when I checked your room you weren't in there so I figured&hellip."I never got to finish my statement as the door was flung open and Cassie was in my face "You went in my fucking room, what the fuck is wrong with you you little fucking perv.
Did you go through my stuff too?" she asked angrily "no I just opened the door and…&hellip." I tried responding "whatever get the fuck out of the way, in fact stay out of the way and don't talk to me till mom and dad get back and even then don't fucking talk to me" she cut me off then pushed her way past me and shut herself in her room.
So thats how things went for the first couple of days, we made sure that neither of us had to talk or see each other for more than a few seconds at a time and snow never let up night or day.
Finally on the third night as I was laying down in my room reading and eating a hot pocket I heard a light knocking at my door, I knew it was my sister after all who else could it be but after 3 days of not speaking I had softened up a little so I said&hellip. "whats up Cassie is everything all right" She slowly opened the door looked around the room and her eyes landed on me finally, I could tell she had been crying, I assumed cause she missed my mom and dad.
I jumped off the bed and said, " Whoa is everything ok, go ahead tell me whats wrong" She sheepishly looked at her feet and said "I kind of have a problem and its kinda why I have been treating you like crap" I moved closer and hugged her as she started crying again, "go ahead tell me whats wrong I am sure I can help" "its not easy to say……" she said between sobs "I can't help if you don't tell me whats wrong Cass" I responded "Ok the reason mom and dad went to town for me was to get me stool softeners and an enema kit cause I am constipated" she responded and immediately burst into hysterical tears I knew at this point she must be in a lot of pain cause that was three days ago and I hadn't heard her flush in the bathroom (it was right next door to my room) "Ok well I am not sure how I can help here Cassie I mean I will look around and see if there is an enema kit or some stool softeners anywhere in the house." I replied while slowly stroking her hair "Don't bother I have check everywhere and there isn't even a tube that would suffice for an enema." she replied "well I really don't know what you want me to do here then." I said kinda looking around the room like an enema kit or some stool softeners would suddenly pop out of the wall or something She began shifting around uncomfortably again and I could tell she had something she needed to say "ok Cass tell me whats up I know you have something to say, tell me I promise I will try to help ok" I asked her softly "well Jack you know my friend has the same problem as me and she said one time when her and her boyfriend were stuck somewhere in the same situation, well he helped her by……well you know" she said while looking down at her feet the tears finally coming to a close "no I don't know Cass I have never had this problem before" I said questioningly "he peed in her ass to help her out" she blurted out in a hurry needless to say I was floored, my sister was asking me to give her a pee enema so she could relieve her pain "Cass I don't know I mean I am your brother" I backstepped away and kinda held her at arms length trying to look in her eyes and see if she was being serious and not playing another joke on me.
She looked up at me and I knew instantly she wasn't kidding around. "please God Jack I am in so much pain, please please please please help me" she said desperately I knew there was no way I could deny her, she was a bitch and tormented me but I couldn't let her continue in pain like this not to mention there could be serious medical side effects if she had to wait another 2-4 days for my mom and dad to get back.
"ok Cass I will help you but we can't tell anybody, not even mom and dad" I said much to her relief "well obviously we aren't going to tell anybody do think this is something I am looking forward to tell anyone" she said playfully It was nice to see her smile after this, so I grabbed her hand and we walked to the bathroom together "so Cass how should we do this" I asked genuinly puzzled "well the tub obviously this is probably going to be messy" she said laughing so we moved over to the tub and climbed in together, she started taking off all her clothes when I stupidly said.
"whoa what are you doing, you don't need to be fully naked just take your pants off" I said hurriedly "no fucking way I don't want to risk getting piss on these clothes this is my favorite shirt, you should take yours off too it will be hard to explain why you have piss on your clothes to mom and dad" she said as she was stripping off her final piece of clothing. Well obviously I was hard, chances were I would need to be for this anyway, so I hesitantly started taking my clothes off.
I got as far as my boxers before I stopped in embarrassment. Cass was staring at me and noticed my embarrassment, "go on Jack its not like I haven't seen you hard before" I was shocked I asked, "when did you see my hard on" Cass kinda smiled and said,"well Jack you aren't exactly quiet when you are jerking off and I was curious so I kinda peeked at you once" Once again I was shocked, but I knew she was right cause I could get quite loud when I got near climax, so I finally stripped off my boxers and revealed myself in all my glory to my sister Cassie's eyes got huge and she said"What!?!
this isn't going to work when I peeked you couldn't have been more than 5 inches how the hell are we going to get that thing in me" "well I am guessing you were peeking at me when I was younger and obviously it grew some Cassie, don't worry I tried anal with my old girlfriend and I know its going to hurt at first but it will fit and you will be fine" I replied smiling inward, it was nice to know my dick was enough to scare her She seemed to be battling with herself before she finally bent over and said,"be gentle its my first time alright." I reached over behind the toilet and grabbed a bottle of ky gel I hid there for when I was well shaking hands with my little man.
I lubed up my dick and started inserting a finger in her ass when she stopped me and asked…… "what the fuck are you doing, this doesn't require you to finger my ass" "Cass this will hurt like a motherfucker if I don't loosen you up a little" I replied She bent over again and I started putting the first finger in again, I got the first one all the way in and was starting to work it back and fourth for a minute or so before I started inserting my second finger.
Cassie suddenly moaned,"oh my God thats good" "are you getting horny from this Cass" I didn't really need to ask it was obvious she was getting turned on by how much her pussy was dripping "just keep join alright I want to get this over with as fast as possible" She replied with a slightly flushed look on her face So I started working my two fingers in her ass back and fourth while she continued to moan under her breath trying to hide her arousal, she was doing a pretty good job right up till I inserted my third finger then she really started to moan I started sawing my fingers in her ass until… "OHHHHH FUCK YESSSSSSSS THAT IS FUCKING INCREDIBLE" she screamed out as she orgasmed for the first time that night, I also noticed her pussy had started releasing more fluids onto the floor of the bath and I took a little pleasure in knowing I had brought my up to now bitchy tight assed sister to orgasm by fingering her ass.
She was starting to come down from her orgasm when she asked in a kind of embarrassed voice, "I am so sorry Jack I just couldn't hold back, am I ready now?" I felt kinda bad I really didn't need to saw my three fingers in and out of her ass till she came so I said, " its alright Cass it was my fault I got a little carried away too and I…well I was going to hold this over your head for awhile but don't worry lets just get this done and forget it happened ok" She smiled at me and said " I can't blame you I have been a little bitchy to you over the years, but yeah lets get this over with now" I pulled my fingers out of her ass and stood up slightly and got ready to insert my full length into her when it kind of hit me that I was about to put my dick in my older sisters ass and piss in her and I kind of hesitated.
as if Cass was reading my thought she said "Jack its alright, I really need your help please help me" That was all the encouragement I needed and I slowly started to insert my dick into her ass, I noticed that a look of pain kept crossing her face and I stopped and asked… "Cass are you alright I can stop, I mean I can try going now if its too much" I said genuinely concerned but she said.
"No Jack I don't want to have to do this again so please put the whole thing in" I was about halfway in at this point and slowly started to insert the rest of my length into her, I finally got all the way into her after a few back and fourth pushes into her when I realized that I was way to turned on to even think about peeing at that point so I figured I had a problem and I need to take care of it, so I started working my dick back and fourth into her ass until at maybe my 5 stroke inwards Cassie wises up and asks&hellip.
"What the fuck are you doing Jack I am in real pain here and you are taking advantage of the situation and fucking my ass you know what I will tough it out till mom and dad get back" she said as she started to pull away from me I stopped her by grabbing her hips and said "Cass its not what you think I just can't piss when I am this turned on, please I am worried for you too I don't think its good for you to hold it in much longer I just need to take care of my problem before I can take care of yours ok" She just stayed still for a minute before saying" ok Jack I should have been thinking about you too this must be really hard for you to do when you are are&hellip.well you know…hard" She started working her ass back and fourth on her own now so I took that as my cue and started to hump forward as she pushed back, we continued like that for about 10 minute when Cass had another orgasm… "HOLY SHIT(no pun intended) FFFFFFUUUUUUUCCCCCCKKKKK MMMMMMMEEEEEE" she screamed out in pleasure I slowed my thrusts while she came down form her high.
"christ Jack are you close yet?" she asked after she had come down "yeah Cass I am close just keep going" I replied as I picked up my humping motion She was getting better or maybe it was involuntary but her ass muscles kept clenching and unclenching trying to get me off, and my God was it working cause after just five minutes more I finally peaked and started cumming buckets straight into her rectum just as she was having what must have been her most intense orgasm of the night.
As she was orgasming her ass muscles clenched down so hard all my thrusting motions were instantly stopped, I noticed what sounded like a hose or something and looked between us and noticed she was cumin so hard that she was squirting all over the floor of the bathtub. I just couldn't resist so I reached under us and started rubbing her clot&hellip. "FFFFFFFFFFFFFFFFUUUUUUUUUUUUUUCCCCCCCCCCKKKKKKKKKKKKKKKK" she screamed as she blacked out from all the pleasure and collapsed on to the floor of the tub.
I gently stroked her hair till I noticed she had lost control of her bladder and was peeing all over herself and me, I expected to be grossed out but I realized that it was kind of turning me on and that was making my dick hard again, so I made no effort to readjust out of her gentle and warm stream of urine running over both of our legs.
She gently stirred and asked'"did you already go is this your pee, oh my God are you hard again I don't think I could do that again?" "No you lost control of your bladder when you blacked out don't worry I think I can go just don't move" I replied So we sat there for long enough that the pee and squirt fluid from my sister had cooled enough to be considered cold when finally&hellip. "Ahhhhhhhhhhhh" I exclaimed as my stream finally started up from my dick into her ass, I swear it must have been at least a gallon and it felt so good I swear it was nearly as pleasurable as cuming in my sisters ass She must have felt the same way cause she was making similar noises as I was as I sufficiently filled her ass with my piss.
When I was done we just layer there awkwardly for awhile till we both fell asleep with my dick and piss still in her ass. I was awakened by Cassie pulling off of my and grabbing me up and pushing me out the door&hellip. "trust me Jack you don't want to see this part" she said as she slam me the door and dashed for the toilet. I heard an audible "Ahhhhh" as I walked away to go make us something for us both to eat So after another couple of awkward days the snow finally let up and mom and dad were finall able to come back and basically round us up for the ride home.
It was on the ride home were my thoughts finally caught up with me and I felt more than my fair share of guilt over what we had done, it was after my third time for mentally kicking myself that my older sister must have realized that I wasn't alright and she leaned over and whispered "Jack you have nothing to be ashamed about I needed your help and you helped me thats all" "But Cass what about the other stuff, you know when I fucked you in the ass" I whispered back "Kinda hard to forget that part Jack" she replied I silently laughed at that (I really don't think my mom and dad would have gotten the joke) "Besides I can't have you all worried, after all the next time we do it I expect the same treatment"She said with a sly grin It took me a second for the words to sink in"You mean you want to do that again?" "Hell yeah, after all it was a lot more fun than when I usually get an enema"………&hellip.