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Jerimiah40 Member Since October 19, 2009

Babysitting Becomes Interesting, Part 3

Jerimiah40 on Taboo Stories

Now, for anyone who hasn't just recently read the past two parts, I'm going to back up a bit.  When our last story ended, the van had just arrived to pick up Katie, Rachel and Emily.  As I hurried to get them out the door and on their way, Jason was still sitting, naked, on the couch.  

    Once the girls were gone, I thought back to that.  I walked back into the house, and into the living room, where Jason was still sitting there, looking confused.  I pulled my clothes back off and went and sat down beside him.  I reached over and grabbed his cock and started pumping up and down on it.

    "Man, you got kind of a raw deal there," I said to him as I jacked him off.  He just moaned in response, making it obvious that he
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liked what I was doing.  I kept going, speeding up as I went along.  He started breathing heavier, and I knew that he was going to cum soon.  Teasing him, I stopped, and began lightly fondling the very tip of his dick.  As he moaned, a little bit of cum started dribbling out, at which point I grabbed the shaft of his cock and started pounding as hard as I could.  All of a sudden, cum was flying everywhere.  I stopped stroking him, and he sat up.

    "Fuck, man, you sure know how to give a guy a handjob."  "Man," I said, "It was the least I could do after a got your sister without you".  "True," he laughed.  "But, you know who else got a raw deal?  Emily.  She came late, so she didn't get to have even a single orgasm.  We should do something for her when she gets back"


Meanwhile, at the party....


    The van containing Katie, Rachel and Emily had just pulled into the driveway.  As they got out the woman driving them called out "Well, I'll see you girls later," and pulled right back out.
    
    Just as she was driving away, the host of the party came running out of the house.  Kennedy, who was the same age as the three other girls, had red hair and only the absolute beginning of budding breasts.  However, at the moment, she was wearing a long, loosely fitting sweater that completely hid them.  It also hid her ass, which was the most squeezable ass ever.  She was used to guys, especially older guys, noticing it though, and it was almost ritual for any guy who was near her to grab her ass as a greeting.  They never meant anything specifically sexual by it though, but it sure was nice.
   
    The four of them ran through the house and out to the back where the huge pool was.  Because the house was quite a ways from town, not only was there almost nobody around, there was plenty of space for a huge backyard with a pool, which was exactly what was there.

    As the girls expected, everyone in the pool was naked.  Kennedy pulled off her sweater, revealing absolutely nothing underneath.  Katie, Emily and Rachel followed suit, and pulled off their bathing suits. 

    "Fuck," said Emily, "I'm SO horny, and this isn't helping.  Somebody fuck me, now."  Only Katie and Rachel knew why, but Kennedy was happy to oblige her wishes.  As Katie and Rachel ran off to the pool, Kennedy and Emily headed off into the grass. 
   
    They sat down together on the grass, and Kennedy started rubbing Emily's pussy, which was absolutely dripping wet.  Without any hesitation, Kennedy stuck a finger in, then two, and then got three whole fingers inside.  She began ramming them in, while Emily screamed in ecstasy.  It wasn't long before Emily had a huge, gushing orgasm that sprayed fluid all over Kennedy. 


    Now, to the casual observer (and probably most people reading this story as well), this would have seemed incredibly odd, the fact that these two girls would so willingly sit down and start fucking.  However, there's a bit of background you need to know.

    These are four girls (counting Kennedy) who have known each other just about forever.  They went through everything together, and at this point, were going through puberty together.  Part of that process, however, involved learning about themselves, something that began one day in Spring.

    That day, it was incredibly cold outside.  The four of them had been planning to hang out outside for a while, but soon discovered that it was far too cold.  So, they headed inside to Rachel's house, where they were.  Since nobody was home, they started talking about the things that girls often talk about: guys, their bodies, etc.  Soon, the conversation came to breasts.
   
    They talked about breasts for quite some time, and eventually, they started comparing.  Of course, this involved removal of clothes, so that everyone could get a closer look at each other.  This soon lead to touching and feeling breasts. 

    Kennedy, being the one who was always the most outgoing, was the first to mention the vagina.  Earlier that day, in school, they had been learning about the female reproductive system, and although they always had their own to examine, there wasn't anything that could provide the same level of realism of seeing someone else's pussy up close. 

    So, before you knew it, they were all completely naked, essentially having a spontaneous all-girl orgy in the middle of the floor.  Although they didn't really mean it in a sexual way, it was at that point that they became extremely comfortable with each other naked.

    Ever since then, they took all chances to get together, and eventually progressed through various stages of fucking, until they were to the point where any of them would willingly fuck any other member of the 'group'. 


    Now, at this point, everyone had run into the pool.  There was some 'accidentally' brushing together in the pool, but other than a pool full of naked 13-14 year old teens, not a lot exciting happened.  So let's go back to the house, shall we?



    Back at the house, where Jason and I were cleaning up, we were still talking about what we could do for Emily when they came back.  The conversation turned to anal sex, and we wondered if she would be up for something like that.  Willing to try, they finished cleaning everything up, and got all set up in the bedroom with lube, vibrators, dildos, and all manner of other toys. 

    Time passed, and it was then around 10:00 PM.  We had received a phone call from Jason's parents, saying that they were staying for longer, and that they wouldn't be home until the next day at the earliest.  This was perfect for our plan.


    Anyways, just at that point, the three girls walked into the house, and yelled out, "We're home!".  Excited, Jason ran out into the living room, completely naked.  His cock was flapping around as he ran.  "Emily," he said, "Come here for a minute.  I've got something for you."

    Emily followed him into the bedroom, where the lighting was low, and there was a towel lying on the bed.  I was standing there naked as well, and instructed Emily to strip down.  "Listen," I said, "You got a raw deal earlier.  I'd like to make it up to you know, by showing you something you may have never tried before."
    She looked around, confused, wondering what it might be.  Seeing the confused look, Jason supplied her with the answer, "Anal Sex."


I think this part of the story has grown long enough, So I guess I'll end it here.  Although, you now know what to look forward too.  I appreciate all the kind words that have been said about my writing in the past, and I'd appreciate it even more if they kept coming.  When rating, however, keep in mind that the action is yet to come.

Babysitting becomes interesting

Jerimiah40 on Taboo Stories

I suppose I should start off this story with a little bit of background.  I'm 16 years old, about 6' tall, with approximately a 7" cock.  This story also mentions a good friend of mine, Jason.  He's also 16, and even taller than I am, probably around 6'2".  We have 'played around' a bit before (completely innocent, we're both straight), so I know he has about a 6" cock.
    This story, as so many do, began with a phone call.  At 1:00 on a Friday, I got a call from Jason.  Now, it started off perfectly innocently.  He had been asked to watch his 13 year old sister and her two friends who would be arriving later.  Later on that afternoon, they were to be picked up to go to a pool party, and they were all meeting there.  However, he had
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misunderstood what time they were leaving (4:00), and he had to go to work .  So, he called me to ask if I'd mind going over there to watch them for a while.
    Now, there were other things that I'd much rather do that afternoon.  However, he'd helped me out in the past, and there was no way he could miss work again (he'd been skipping out quite a bit, and his boss was starting to get pissed), so I agreed.
    I walked over to Jason's place, and arrived just as he was leaving.  I headed inside and saw that only his sister (Let's call her Katie) was there so far.  I said hi to her, then went to sit down on the couch.
    Now, although she was only 13, Katie was definitely what you could call good looking.  She was about 5'2" tall, with long-ish brown hair, and B cup breasts.  Despite the fact that I'm good friends with her brother (who she doesn't like much), I'm friends with her.  Now, I'm no pedophile, but I have occasionally thought about her in a sexual way.  However, I had never really considered actually doing anything to her.  At this time, as she was getting ready to go to a pool party, she was wearing a VERY skimpy red two-piece bathing suit, which really didn't leave much to the imagination, and didn't to much to stop my sexual feelings for her.
    She followed me into the room, and sat down on the couch beside me (rather close, I might add).  At this point, I instantly got a hard-on, which I tried to ignore.  I asked her what she wanted to do for the next couple hours before they left.  She told me that she had some ideas, but she wanted to wait for her friends to come by first before they started doing anything.
    We sat and talked for a while, and then the doorbell rang.  I got up to answer it, but she ran ahead of me.  She walked back into the room with the first of her friends, who I'll call Rachel.      Rachel was slightly shorter than Katie, at 5' tall.  She had a darker skin tone, long, dark brown (almost black) hair, and although she was also only 13 years old, she was drop-dead gorgeous, despite her complete lack of breasts.  She was also wearing a bathing suit, which was even smaller then Katie's.
    I went back and sat down on the couch, and they followed me, and sat on either side of me.  We sat there in silence for a while, and then Katie exclaimed "Oh my God Rachel, that is a beautiful bathing suit!" She reached across me, brushing my fully erect cock, and felt Rachel's bathing suit.  I thought I was imagining things, but I could have sworn Katie was rubbing Rachel's cunt through the bathing suit.  Rachel replied "I know, I got it last week just for this party.  Your's is really nice too". Katie replied, saying that it was really old and that she needed a new one, but Rachel insisted.  
    After a few moments of silence, Rachel said to Katie "So, we've got some time.  Want to try mine on?"  Katie agreed, and they both stood up.  Rachel headed towards Katie's room, but Katie went to the window and pulled the blinds shut.  She asked Rachel, "Where are you going?"  Rachel looked confused, but without replying, came back into the living room.  Katie continued "I'm sure Jay won't mind, this will just take a moment."
    And at that, without even bothering to turn away from me, Katie took off her suit.  After a little bit of hesitation, Rachel removed her suit as well.  They traded, but before they could put them back on, Rachel exclaimed "Holy shit Katie, you're beautiful!".  Then she, realized that I was still there, and began to blush.  Katie and I started laughing, as Katie said "Thanks, so are you".  
    Once Rachel realized that we were both totally cool with it, Rachel said "No way, not as beautiful as you.  I wish I had those breasts.  
    As they compared bodies, I just sat there staring at both of them.  This was almost like a dream come true.  I couldn't believe that they were both so fine with being naked in front of me.  Just as I started fantasizing about feeling them both up right there, Katie said "So Jay.  You're sitting there getting this free show," She looked down at my crotch, and continued, "and obviously enjoying it."  Her and Rachel starting laughing.  Then Katie continued, "Let's see what you're like".
    I hesitated for a moment, and then said "You want me to get naked too?"  Rachel replied, saying "Sure, why not?  Neither of us have ever seen a real cock before, and since you've already had this show, I think it's only fair."
    Now, I suppose I should probably go into a little more detail about myself.  I'm around 6' tall, as I mentioned earlier.  I've got short brown hair, and no facial hair.  I've got a fairly average build; not toothpick-skinny, but not overly large either.  I've been told before that I'm very good looking, however, I'm a nerd. In a way, I was sort of everyone's guilty pleasure.  I came from a school where status is everything.  As much as everyone stares at me, no one would ever admit it, because who would ever look at a nerd in that way?  That was the main reason that, before this day, I had never seen a real pussy before.  
    So, I decided that fighting this would be a losing battle, so I started to strip.  I took off my shirt, then my pants, then my socks.  I was sitting there in only my boxers, and Katie and Rachel were staring apprehensively. I very slowly started to pull my boxers down, and finally removed them completely.  They both stood there staring for a while, without a word.  I took the opportunity to stare at them both some more.  Katie finally broke the silence by saying: "Well Jay, I think this is your answer as to what we should do this afternoon."
    They walked towards me, and I threw my hands up.  I may be a horny teenager, but I was  a little bit hesitant here.  "Do you realize what could happen?" I asked them.  "Number one, if we do go through with this, you would never, EVER be able to tell anyone.  We could all get in a shitload of trouble.  Secondly, what if I were to get either of you pregnant?  How would you explain that?"
    Rachel replied first, saying "Look at me!  I don't even have tits yet, I haven't had my period before.  It's impossible for me to get pregnant!"  I replied, saying "Okay, but what about Katie?"  She said, "I know my dad has condoms in his bedroom.  I know it's not 100% safe, but it's better than nothing, right?"  I said fine, and then moved onto one final point.  "You two said earlier that you'd never seen a cock before, so that means you're both virgins.  Are you sure you want me to be your first time?"  They looked at each other and, without any hesitation, said "YES!".  
    So, I told Katie to go get the condoms, and told Rachel to come closer.  I asked her, "Do you know what sixty-nine means?"  She replied "Yeah, it's when a guy eats a girl's pussy and the girl sucks his cock at the same time."  Not bothering to ask how she knew that, I told her that was what we would do first.  I lay down on the couch, and she got on top of me.  She eagerly took my cock into her mouth as as I slowly started licking her tiny slit.  She struggled a little bit with my huge cock at first, but she quickly got a rhythm going, up and down on my cock.  I followed her rhythm, driving my tongue in and out of her now-wet pussy.  I could feel my balls tightening up, and yelled "SHIT, I'M GOING TO CUM!".  Rachel yelled back "ME TOO".  Just then, Katie  walked over and shoved a finger up Rachel's ass.  Rachel squealed with pleasure, and unloaded a huge amount of juice all over my face.  At the same time, I came hard in her mouth.  I started lapping up the juices off her pussy, and as I did, Katie came over and started doing the same.  Our tongues met over Rachel's pussy, and we started making out.  Rachel got up off of me, and started lapping up her juices off my face.  Katie said to her, "Shit Rachel, you taste good!".  Rachel replied, "If you like that, you should try Jay!".
    With absolutely no hesitation, Katie got up and kneeled down at my cock.  She was about to start sucking, when I said "Wait a second.  If you're sucking me off, I get to eat you too." So, she got up on top of me in the same position, and we went at it.  Katie tasted even better than Rachel had, but she wasn't as good at eating cock.  However, it wasn't long before we both came on each other.  
    We sat up, and looked over at Rachel.  She was sitting on the floor facing us with a finger in her pussy.  I whispered to Katie "Come on, let's give her something to really watch".  I drew Katie closer to me, and we started making out.  I reached down and started fingering her pussy as we made out.  She reached down and grabbed my cock, and we sat on the couch, rocking away.  We both came again, as Rachel came on the floor.  I said to Katie, "Damn, you've got a tight pussy.  Are you sure you want this thing in it?"  She said "Yes, definitely.  But first, I need a bit of a break.  Why don't you let Rachel take a turn with you.
    I agreed, and Rachel ran over and jumped on me.  She started kissing me with amazing force.  She stopped for a second, and said "Fuck me Jay, fuck me now".  She got off me, and stared at me with the cutest expression on her face I had ever seen.  There was no way I could say no to that face, and I told her so.  "But first," I said, "A few things you should know.  Firstly,  you're still a virgin, so you've still got your hymen fully intact.  You should know that it will hurt like hell when it breaks, but it will feel incredible after that.  However, you're also incredibly tight, so that will increase the pain at first, but it will make it even better for both of us  later on." After that, she looked quite a bit more nervous, so I said to her, "It's okay, it will be fine."
    With a much more confident look on her face, she said "Okay, let's go!" So, I moved to the floor and lay down.  Then, I began to instruct her.  "Okay, first of all, stand over my cock.  Now slowly, start to crouch down onto it."  She began to come down onto my cock very gently. As she came into contact with my rock hard cock, she shuddered a little bit.  Then, she started to push a little harder, groaning with a combination of pain and pleasure.  I told her, "Take it at whatever pace you feel comfortable with."  She stopped for a second as my cock slid into her pussy a little ways.  Then, with one deep breath, she plunged down hard onto my cock.  She screamed with pain as I felt her hymen break.  My 7" cock now all the way inside her pussy was all it took for her to have her 3rd orgasm in the past hour.  However, I wasn't done with her yet, so I encouraged her to keep going.  
    I reached forward to where she was still sitting on my cock, and started to tweak her tiny little nipples.  She started to bob up and down on my cock, which felt great.  I couldn't believe it, my fantasy was about to come true.  I was lying here, being fucked by my best friend's sister's 13 year old friend.  And the best part, Katie was waiting her turn to take a ride as well.
    As she was riding up and down on my cock, she started going faster and faster.  As she did, I started bucking my hips and ramming my cock up even harder.  I could tell that she was in pain, but that the extreme pleasure that she was experiencing was even greater.  She screamed, "I'M GOING TO COME".  That was all it took for me, so I unloaded a huge load into her tight pussy.  As I did, she had her 4th orgasm of the afternoon.
    She got off, and crawled over to my face.  She lay down beside me, and said "How was that?"  I replied that it was amazing, then I turned towards her and started kissing her.
    Then, Katie said "Hey, what about me?  I'm still waiting over here".  I sat up and looked at her.  She was holding a box of condoms, and looking very impatient.  I said to her, "Okay, you're next.  However, since I have to wear a condom, you're going to have to do me an extra favour.  Before I fuck you, you have to put the condom on me, using only your mouth."
    She looked a little confused, but she really wanted that fuck.  So, she unwrapped a condom and crawled towards me.  She put it on the top of my cock, and using her mouth, began to roll it down onto my cock.  I was starting to get a little tired, so my cock wasn't as hard as it was before, but it was still hard enough that Katie eventually got it on.  By the time she got it on me, I was so turned on that I could have just plowed straight into her.  However, I had to make sure she understood all the rules as well.
    "So," I said to her, "You heard everything I told Rachel, right?  About how much it will hurt at first?"  "Yeah," she replied, "But I'm ready.  I can take it."  I said to her, "Okay then, start off the same way as Rachel did".  
    But, the words fell on deaf ears; she had already began lowering herself down. However, this was no cautious start, she just rammed her pussy straight down onto my cock.  The sudden burst of pleasure of having such a tight pussy wrapped around my cock was enough that I came instantly, as did she.  I could see tears in her eyes, but she said "Always better to get it over with fast, that's what I always say!"  And, with no hesitation, she started to bounce up and down on my cock.  She was fucking me so hard, she was flying right off my cock on the upstroke, and my balls were smacking against my ass on the downstroke.  For a while, she winced every time she sank back down onto my cock, but she very quickly got used to it and started going at it HARD.  We both came 3 times during that little fuckfest.
    After the third time, she rolled off my cock and fell asleep right there on the floor.  I removed the condom, which was absolutely dripping with my cum.  I said "SHIT!".  Rachel came over and saw the condom, which was covered, inside and out, with cum.  I knew at that point that there was absolutely no way that some cum hadn't gotten inside of her.  So, I immediately whipped out my cell and called my uncle, who agreed to go pick me up some birth control pills that I could give her.  
    As I hung up, Rachel walked over to me, and told me to look at Katie.  "Isn't she hot, lying there naked?"  I agreed with her, and said, "You know what we have to do, right?"  She looked at me, confused.  So, I lay down behind her, and started licking her pussy.  Rachel came beside me and did the same.  "Wow," Rachel said, "You both taste great, but together, it's amazing!"  When Katie didn't wake up, we gave up pleasuring her and started making out.  Just then, as we were all lying naked on the floor, we heard the doorbell ring, and the door began to open.  


Don't forget, these girls were getting picked up for a pool party.  As well, Katie's parents were out, who knows where?  If you want to know what happens next, leave me good feedback, and I'll get to work writing the next part.

Babysitting gets interesting, final

Jerimiah40 on Taboo Stories

Lets see, where were we..... Oh right, Anal.  In the last episode, the girls had just gotten home from the pool party, and it has been revealed that the guys (Jason and I) are going to show Emily the pleasures of Anal sex.

Jason and I led Emily into the bedroom where we had prepared everything.  She, completely naked, lay down on the bed.  Despite showing a certain enthusiasm, her face definately showed some apprehension.  "Don't worry," Jason said.  "This will be fun!  It'll hurt a bit at first, but we'll try to make it more fun than anything else."

Jason walked over to the table and grabbed the smallest dildo there, as I grabbed a bottle of lube.  I squeezed a bunch into my hand, and started massaging Emily's sw
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eet asshole with it.  As I did so, Jason started licking Emily's nipples to get her horny and ready to go.  As I massaged the lube into her ass with one hand, I started fingering her clit with the other.  She was moaning pretty quickly, so we began with the Anal.

I decided that her ass was sufficiantly lubed-up, so I started by poking one lube-covered finger in.  Despite all the lube, it still wasn't easy.  However, I managed to get it all the way in, which drew a slight whimper from Emily.  I leaned forward and licked her lips, and assured her, "It will get easier, believe me".  And with that, I started slowly drawing my finger out and then pushing it back in.  Pretty soon, I was finger-fucking her asshole, and she was loving every second of it.

"Fuck," she said, "That feels so good! Keep doing it!"  As I did, Jason started lubing up the dildo he grabbed earlier.  I withdrew my finger, and Jason came over with the dildo, slowly sliding it in.  As he did, Emily began to shiver and moan as she had her first ever Anal orgasm.  But Jason didn't stop there, he continued fucking her ass with the dildo, and she kept moaning right along.  

Beginning to feel left out, I started fucking her pussy with two of my fingers.  She yelped a little bit at the sudden penetration, and then started moaning even louder.  As she came for the second time, Jason pulled out the dildo.  "Okay," I said, "Time for something a little bigger", as I started stroking my cock.  Pretty soon, however, it was hard as a rock, and ready to go no place any cock has ever gone before..... Emily's tight ass.  

Jason passed me the lube, and I squirted some onto my cock.  As I did, I began giving Emily some instructions.  "Okay, I want you to turn over, and go down on your hands and knees, okay?"  She did as I asked, and I got up behind her on my knees.  Very carefully and gently, I started pushing my cock into her ass.  However, after being warmed up from all the other activities, it wasn't too hard to get it in.  However, as I started going in further, even further than the dildo had gone, she began screaming with pleasure.  It wasn't long before her ass had sucked in my entire cock, and I started sliding it back out, still very slowly.  As I did, Jason stuck his head underneath and started to lick her clit at the same time.  

Meanwhile, I was beginning to speed up, pounding harder.  Her ass was like a vise on my cock, and it felt so good.  I yelled, "Fuck, I'm going to cum in your ass!"  As I did so, I could feel it squirting out, coating her ass with my cum.  She screamed from the extra sensation, and came shortly after.  I pulled my cock out, and Emily rolled back over and lay down.  "Wow," she said, exhausted, "that was great!"

Jason then got up onto the bed, and lowered his cock over Emily's mouth.  Emily reached out with her tongue and started licking the tip.  As they did that, I went and found Katie and Rachel, in a 69 position on the couch in the living room.  They didn't even notice as I walked in, so, my finger still covered in lube, I walked over to where they were standing.  Sensing that they were about to cum, I stuck my finger into Rachel's ass, which caused her to scream into Katie's pussy.  As I did, she came.  Hearing Rachel cum caused Katie to come as well, and they both then collapsed onto each other.  

"Hey there, pretty ladies!" I said.  "Come to Katie's bedroom, I think it's time you guys got some action."  So, they followed me down the hall to where Emily and Jason had just finished up.  "So, I want some pussy," I said.  "Katie, you up for it?"  However, before Katie could reply, Jason said, "No way.  I want my sister next!"  They lay down on the bed together, and Jason began pushing his cock at Katie's tiny pussy.  It wasn't long before he was pounding into her harder than I'd ever seen anyone pound, and I've seen some pretty tough stuff.  Katie was screaming the whole time, mostly in pleasure, but with some definate pain mixed in.  Jason was loving every second of it, and soon he pulled his cock out and blew his load all over Katie's chest.

As this was going on, I lay down on the floor with Rachel, and began massaging her breastless chest.  I leaned my head over and we started making out on the floor as I massaged her.  I sat up, and looked down at her pussy.  It was dripping like a leaky faucet.  "Rachel, you're leaking a bit down there!" I remarked.  "Let me get that cleaned up for you."  As I said that, I moved my face down towards her cunt and started lapping up her sweet, young juices.  She moaned with pleasure, as I stuck my tongue straight into her pussy.  I started wiggling it around in there, which made her come almost instantly.  As she did, I got a facefull of liquid!  "Rachel, I didn't know you were a squirter!  That's SO HOT!" I stood up, and with only a few strokes of my cock, I was cumming all over her face and chest.  As Rachel was licking all the cum from around her lips, I commented "You know, I should probably be getting home pretty soon.  Anyone want to come take a shower with me?"  Katie jumped up immidiately, and followed me to the bathroom, where we got into the shower.

We started the water, and started soaping up our bodies.  As we did, I asked, "So, did you have fun this afternoon?"  Katie replied, "Hell yeah!  There's just one thing I want to try..."  I looked at her as her voice trailed off.  After a bit of silence, she said, "Can you show me anal sex?  Like you showed Emily?"  "Okay, " I replied, "But only once.  First, I guess this soap will do for lube.  Start rubbing it around your ass."  As she did, I kneeled down on the floor of the shower, and started poking at it with my finger.  It was easier, because she had a slightly looser asshole than Emily had.  Soon, I was fucking her with my finger, and she was moaning away.  As she came, I stood up.  "Now, " she said, "I want you to stick your cock in my ass."  As she said this, she lathered up some soap on her hands, and started rubbing it onto my cock.

Shortly after, I told her to turn around, and put her hands on the wall and lean forward.  As she did, I pointed my cock at her ass, and started poking.  She giggled a little bit, and I continued pushing.  It wasn't long before, *pop*, it was sucked in.  Katie gasped loudly, and then started rocking back and forth on my cock.  Soon, I came in her ass, pulled out, and watched my cum dribble out of her ass.  Using my finger, I then began wiping some of the cum out of her ass, which caused her to come as well.

"Now, " I said, "We really have to clean up."  So, we began lathering up soap again, concentrating on locations where there was evidence of sex.  As Katie started washing her pussy, I couldn't help but reach out and touch her tits.  I started lathering them up with soap, which felt absolutely fantastic.  Touching those wonderful little titties almost made me cum again, but I managed to hold it in.  

The rest of the shower was fairly uneventful, so when we were both clean, we went back to the living room to retrieve our clothes.  When we arrived, we found Rachel, Emily and Jason lying on the floor having a three-some.  I announced that I was leaving, after I got my clothes on, and that I hoped to do this again.  However, I had the feeling that it probably wouldn't.


Well, that's the end of the story.  Hope you all liked it.  I've got a few stories in progress right now, although I'm not sure if either of them are going where I want them to.  Got any requests for stories?  Mention it here, although I'll be much more motivated by good feedback.

Babysitting becomes Interesting - Part Two

Jerimiah40 on Taboo Stories

    So, when part one of the story ended, the doorbell had rang.  NOT the kind of thing you want to have happen while you're lying naked on the floor with two underaged girls, who are also naked.  Me and Rachel panicked, as Katie slept.  Whispering, I instructed Rachel to drag Katie out of sight somewhere, while I quickly got dressed.  However, staying hidden was futile from the beginning, as the unknown guest was already in the house.
    As we were frantically trying to hide, a female voice came from the entryway, "Hello?  Is anyone home?"  Rachel gasped, and said "It's Em!"
    When she said 'Em', I instantly knew who she was talking about.  It was Emily, the third girl who was getting picked up for the pool p
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arty.  I knew her fairly well, as we had gone out once.  She was taller than all the rest of them, around 5'5" or 5'6".  She had breasts on the large side of a B-Cup, and had blonde hair.  
    She wandered into the main part of the house, where we were all naked.  Emily just stood and stared for a second, before asking "What's going on in here?"  For a while, nobody spoke.  Then, Rachel timidly said, "umm....... we were bored."
    As we laughed, Emily continued staring at us as if we were all insane.  With the sudden noise, Katie began to wake up.  However, as soon as she saw Emily, she jumped up right away. "Shit," she said, "Em, what are you doing here!?"  She replied that she was here for the party, of course.  After an awkward silence, Katie asked "So..... what do we do next?"  They looked at Emily, who was still in her bathing suit.  Without requiring any further cues, she peeled off her bathing suit.  Katie and Rachel looked surprised, as they looked from me, to her, and back to me.  Emily said "What, it's not like it's anything he's never seen before."  Katie and Rachel looked at me, shocked.  
    I had never mentioned it to anyone, but the one time that me and Emily went out wasn't just one time.  That 'one date, as friends', quickly turned into another, and another, and eventually turned into us being naked, alone in my basement.  There was no actual fucking, but we did get quite an opportunity to closely examine each other.
    Emily told us her story at that point:
    About 2 months ago, her parents had gone on vacation, leaving her brother (who was my age), in charge.  The first night they were gone, he held a party at their place, after which many drunk teenagers had needed a place to stay.  Knowing that his parent's wouldn't be home for a week, Jon (that's her brother), let them sleep on the floor in the living room.
    Now, she assumed before her brother had woken up, a small group was already awake.  They came up the stairs, and quietly entered Emily's bedroom, where she lay, still asleep.  However, after seeing that sexy, almost-nude body lying in the bed, all thoughts of carefulness left them.  They quickly ripped off the blankets, and began stripping her.  Of course, she woke up and began protesting, but to no avail.  
    One of the guy's began grabbing and sucking her tits, while another one started jamming fingers in her pussy.  Her screams of pain were just encouragement for the guys to continue.  It finally ended with one of them fucking her hard in the pussy.
    After that event, she talked to her dad, without revealing any of what happened.  She posed the question as a what-if someone tried to rape her some day, and convinced her dad to get her birth-control, without the knowledge of her mom.  Ever since that day, she had been on the pill.
    Which leads me to the whole basement scene.  After a date, she came into my house with me, where we headed down to the rec room in the basement.  We started watching some dumb movie, but mostly just cuddled on the couch.  
    At one point during the proceedings, Emily told me the whole story of what happened.  She said that, although it was extremely painful, there was definitely pleasure too.  She said that she wanted to know what sexual contact with a guy felt like, but not in a forced way.  So, that led to us naked, feeling each other, but, as I mentioned earlier, no actual sex.
    Which brings us back to the main story.  Emily said, "So, that's why I don't mind seeing him naked."  She looked at me, and said "Well, how about it, do you have one more fuck in you for me?"
    It was probably the hardest thing I had ever done, but I had to admit that I probably was done fucking for the day.  However, I told her that I'd do anything else she wanted with her.  
    I lay down on the floor, and Emily came over and lay beside me, her pussy right beside my face.  I saw that her pussy was absolutely dripping, took it as an invitation to dig in.  So, I started licking her pussy, as she played with my cock a little bit.  Before long, my cock was starting to get hard again, which she also took as an invitation.  Pulling away from my face, she told me to get up.  She kneeled down on the floor in the 'doggy' position, and told me to go ahead.
    So, I did.  Moving behind her, I started filling her pussy with my cock, thrusting with all the strength I could still muster up.  As this was going on however, I heard the door open.
    At this point, there was a major battle going on.  On one hand, there was nobody else who was supposed to be here, and I knew that this would  not be a welcome sight for anyone walking in.  However, there was NO WAY I was going to give up my final prize, the girl who I had dreamed of fucking ever since our first date.  
    As I thrust one last time, as hard as I could manage, I came one last time.  I instantly pulled out, and told them to hide.  However, it was too late, as I heard a familiar voice coming into the house.
    As Jason walked into the room, he was obviously mad.  "The stupid fucker fired me!  He fucking fir......"  He had been yelling, but he trailed off as he looked up and saw the 4 naked people in the room.  "What in the fuck," he said, starting quietly, progressing to a full out scream, "IS GOING ON IN HERE!?"  He looked around, seeing me, his naked sister, and her two naked best friends.  "And more importantly," he continued, "Why was I at work when I could have been here!?"
    With absolutely no hesitation,  he stripped down, ran to the couch and flopped down right where Rachel and Katie, his sister, were laying.  Katie was obviously somewhat disgusted, but Jason had absolutely no second thoughts.  
    As we all stared at him, Emily finally spoke up. "Umm.. Jason..... I got here kind of late, and Jay didn't have much left in him.... could you....," she trailed off, gesturing at her wet pussy.
    Jason didn't need any coaxing, after that invitation.  He told Emily to come over to where he was, and sit on him.  She did just that, and began slowly.  After a while though, she started actually standing up and slamming back down on his cock.  
    As this display was happening, I looked at the clock. The time read 5 minutes to 4.  "Umm.... guys....", I said to them, "I hate to break this up, but your car's going to be here in 5 minutes.  Everything suddenly stopped.  Nobody spoke, until Katie broke the silence with a single word.
    "Shit."
    As they started running around frantically, I took back my role as the babysitter, and started barking orders.  "You three, go shower.  You smell like sex.  Don't worry about taking turns, God knows you've seen enough of each other already, I think you can manage.  Just worry about the key areas.  Make sure you don't stink.  Then, get your bathing suits back on.  Me and Jason will clean up."
    Just then, I heard a horn honk from the driveway.  Jason was still sitting on the couch playing with his cock after being left so abruptly before cumming.  I quickly got dressed and ran outside, knowing that they'd leave if they thought nobody was home.
    So, I headed outside and told the driver that they were on their way, and that they had forgotten to pack a few things.  I headed back into the house to tell them that their ride was here, and to hurry.  Fortunately, the shower was over, so they headed outside and left.  But, as they left, I called out, "We'll have to do this again some time."  


So there, everything turned out fine in the end.  However, is this really the end?  Who knows what could go on from here.  I've got some thoughts, but there's no point putting them down if nobody's appreciating my work.  So, if the good ratings keep coming, so will our main charactors!