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Babysitting becomes interesting

Taboo
2007-01-01

I suppose I should start off this story with a little bit of background.   I'm 18 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 18 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 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.

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    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.

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    She had a darker skin tone, long, dark brown (almost black) hair, and although she was also only 18 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.

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    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.

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    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.

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    "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.

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    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.

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    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".

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    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.

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  "  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 18 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.

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    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.

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    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. .

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