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Babysitting gets interesting, final

Taboo
2007-07-26

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 sweet 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.

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    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.

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    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.

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        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.

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        "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.

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        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.

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        "  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.

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          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. .

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