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shingle Member Since September 29, 2011

Friday night and I have to Babysit

Kellyy on Taboo Stories

So the jest of the basics here is that I'm pretty much ready to go out for the night when the neighbour comes over and needs me to babysit.  You know, it's been over ten years since I babysat someone's kids.  Not that I didn't mind too much, but it had been weeks since I'd had some good sex.  I wanted to go out with my friends and hopefully find some guy to take care of my needs.  But this seemed to be an emergency so I said yes.  "I don't think I'll be home till tomorrow, so that's okay right?"

"Send him over, tell him to just come in, I have to make some phone calls"  Ok Deb said, I'll send him right over.  Jim was a pretty quiet kid from what I knew.  A bit of a geek but still a pretty good looking kid, his mom j

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ust dressed him in all the geek apparel.  I think he's 13 or 14, I know he is heading into High School next year.  I on the other hand am 26, jet black straight hair, long toned legs, with what I think is a nice tight ass and tear drop titties with big nipples that point straight up.  I love to wear tight jeans and short skirts just to watch the guys stare at me.  One time, I watched a guy walk right into a newspaper stand while watching me.  It was so funny.  Sorry guys but you are so 'one minded' when you see a body like mine.

I was on the phone when he came in with his gym bag knap sac thingy.  "Just set it down anywhere, the TV is in the other room, go ahead and help yourself" I said.  Continuing to talk to my friend Cindy I told her how I was a bit upset that I had to stay in for the night.  'I need to get laid bad too'  As I reached down and brushed my pussy a bit through my dress.  'I even bought this smoking dress too Cindy, I am dressed to the hilt with that nice perfume you like, no panties and arrgghh my pussy is already wet.'  Oh, you poor thing, tell me, you want me to take care of that pussy of yours if I don't find a nice hard cock to take home tonight? Cindy purred.  Cindy was always after me, she liked it both ways but I've just never taken her up on it.  "Oh Cindy, you know how I stand on that, but if you find two of them, come on over" I giggled still brushing my pussy gently.  Cindy laughed in her sweet way and ended the conversation with 'you don't know what you're missin sweetie' and then she hung up.

Cindy had been my friend for many years and I knew I didn't have to worry about her so I just laughed it off and hopped up from the stool I was sitting on and headed to the kitchen.  I opened the refrigerator looking for a pop or something to offer my guest.  Not much in here I thought, a gingerale, a half a box of milk, and some tomato and orange juice.  Well, I thought, I should probably ask him if he's hungry or thirsty or what.  We may have to eat out tonight.  With that I laughed to myself at the thought ' eat out ' and trotted off to the living room in my siletto heels.

As I walked into the living room I realized that I had left the satelite channel clicker unsecured to the adult channels.  You know how you can password protect that, well, I had not reset it to protect the channels.  Here was Jim, standing in the living room staring at the bigscreen on an adult channel of some chick going down on some guy.  "Oh, damn" I said startled the boy.  "I'm sorry" he yelped, "I just turned it on and clicked the channel button up a few times and this was on."  Well, why didn't you keep changing channels I asked.  No answer, he was still watching.  "Jim !!" " Sorry" he stammered rapidly clicking on the clicker to change the channel.  Finally hitting the power button.  He turned away from me and again said "I'm sorry, it's just, well, I never seen it before"  It's ok Jim, I'm sorry for not telling you I had that on there.  I just ordered the full channel package so I get all that too.  Listen, why don't we go out and get a bite to eat so we can forget about this.  "oh, ok" he said, still facing the other direction.

 "Well, come on now, lets go" and I walked over to the entrance closet to grab my purse that I had just set there 15 minutes ago.  I stood at the door for a minute or so and Jim was still in the living room.  Come on Jim, lets go I yelled.  "Be right there" I heard.  Now what could he be doing I thought.  Then I had my answer as he walked out.  "hmmmp" I snickered and turned toward the door.  I did my best to keep a straight face but I couldn't help but notice the bulge in his pants.  I guess he seen a bit too much, maybe I should ask him if he needs to use the bathroom before we go.  Actually, maybe I should just check my hair and off I went to the bathroom.  "I'll be right out, I just want to check my hair"  I heard a faint 'ok' in the back ground as I entered the bathroom giggling.  With my hand over my mouth, shaking my head I realized that  he wasn't the only one with something erect.  My nipples were pushing right through my bra and dress like I had nothing on.  I tried to get the twisted thoughts out of my head and calm down.  Soon my nipples returned to more to normal and I left the bathroom.

As I approached Jim I noticed that the bulge was still there a bit but not nearly as big as before.  Jim kept his head down the whole time, must have been a bit ashamed but never the less we left the house and headed down the road.  I own one of those nice 'T' top camaro's  and I've had it for what seems like forever.  My dad taught me how to look after my vehicals so it should last me a long time.  But when you get into it in a short dress like mine it tends to help the dress to ride up.  Since I normally ride along to work and such, I didn't pay much attention to it until we had driven many blocks.  I tried asking Jim questions to help him feel more comfortable with me but he kept his head down.  Then I noticed he was glancing over at my legs.  Hmmmm, I thought, now this kid is gonna get another boner so maybe we should go through a drive through.  Sure enough, he adjusted himself in the seat a few times trying to get comfortable and cover the growing bulge in his pants.  I was beginning to think that even though it might be a bit cruel of my, I could tease him a bit more until we get back home then see if I can get him to take a 'bathroom' break if you know what I mean.  I remember all those early years hearing of the boys on dates that had to beat themselves off because of their woodie wouldn't go down.  Maybe Jim needed it.  Hey, why not, give the kid a little thrill now and then let him see just enough to deserve a good jerk off.  He'll tell all his little friends that he caught glimpes of his neighbour and for a little while, he'll be the 'cool kid'.

"Look over there, what are they building there I wonder" I said pointing out his window to get him to look.  As he looked, I hiked up my dress a bit more, well, almost too much. But I just kept talking like I hadn't done anything.  "I don't know" he said looking out the window.  "Well, looks like it's gonna be pretty neat huh" I exclaimed, keeping the conversation going.  "Ya, maybe... " as he turned toward me he noticed my skirt hiked up higher and more tanned leg and lost his train of thought.  " ah, ah, maybe ah big mall or something" he managed to get out.

Oh, I kept this boy talking, so I could hear his voice stammer along, and make it seem as though I didn't know my skirt was so high up.  We went through a fast food drive through and told him "when we get to the order mic, you have to tell them your order"  I just wanted to see him look past me.  We pull up to the place to order and I told him to go ahead.  He turned my way and I leaned right back for him, he looked right across my boobs with wide eyes and took a quick look down my dress top.  I then slid down in my seat a bit because I knew he would look down.  And sure enough, he did.  I watched him take a big breath, swallow and squeak out the words " I'll have a double burger, loaded, with fries and a large coke."  I just grinned as he slowly looked away.  I slid back up in my seat, leaned toward the window and this is what I said, " and I'll have a cheese burger, fries, and a large cock too." that's right, I couldn't believe I said it.  Jim turned to me with a huge surprized look on his face.  I just ignored it because I knew I couldn't correct myself, I just had to look as though I hadn't made a mistake.  The guy that took our order repeated it back to us with a bit of a laugh. "so, that's, a double burger, loaded, a cheese burger, two fries, and two large 'cokes' (he said slowly and clearly).  "Yes" I replied. "That'll be $12.54, come on around to the window.  As I drove around to the window, I could see Jim had a bit of a grin on his face, but my plan worked.  Even though I had made a bit of a blunder on words, I could see his pants had a big tent to them.

I paid for our order, received our change and we drove off.  We only drove a block or two when I pulled over in a small parking lot over looking the river.  We watched people walk along the river as we ate.  We both ate our fries first and almost at the same time we bit into our burgers.  My burger had a lot of ketchup on it and it began to drip onto my hands.  I held it out a bit and it dripped right onto my left leg.  "Get a kleenex, hurry" I exclaimed.  I don't want it running down my leg.  Oh, it was warm from being on the burger, my hands had all the ketchup all over them.  I was licking all the stuff off my hands still holding my burger when I felt Jim simply take a kleenex and reach between my legs and wipe up the ketchup.  A chill ran over me.  He folded the kleenex and kept wiping but now he was doing it ever so slowly.  It's as if he did in on impulse and now, his boyhood was taking over.  I quickly set my burger onto the wrapper I had set on the dashboard and reached down to his hand.  He looked up at me and snatched his hand away.  Grabbed his burger and filled his face.  I made a short 'huh' kind of laugh and said "sorry about that, I didn't mean for you to do that, just to get me a kleenex."  He didn't say a word.  "But, you did a good job so thank you".  Still nothing.  We ate our burgers in silence while sipping on our drinks.  Jim is one of those guys that has to move the straw in and out and make that "squeekie sound".  "Jim, stop that, it drives me a bit crazy.  Well, lets get going as I took the last bit of my burger and 'plop', right on my dress top.  Rolled down my breast to my skirt. "ah crap, get me another kleenex"  Jim handed me one this time.  I quickly wiped up the ketchup but it was too late.  "Now we have to go" I said.  Starting the car.

We arrived at my house and I told Jim to bring the pops and garbage into the house because I had to get the stains out of my dress before it sets in.  I quickly got into the house and into the backroom where I do the washing.  I closed the door (at least I thought I closed it) and stripped off my top.  I began by adding some water then spraying it with a stain killer.  I added water to my skirt and sprayed it too.  Then I turned toward the door to see it had come open and Jim was standing there watching me with a large pop in each hand and an obvious boner.  There I was, in one of my sexiest bras with a young teen boy watching me.  I reached out and closed the door.

Grabbing a towel and wrapping it around my chest, I took off to my room.  As I passed Jim I said "Go to the living room and watch some TV" then I added, " NO PORN either".  As I skipped up the steps in my stilettos I found myself getting turned on.  This was just wrong.  All I wanted to go was give the kid a thrill.  Not turn myself on.  As I changed in my room, I decided to get into a more relaxed outfit.  I put on some ladies sports boxers, a sports bra and my long nighty shirt.  It goes to my knees.  I checked the mirror before I left and all looked well.  Downstairs I went to find no Jim in the living room.  The pops were there, the TV was on, but no Jim.  I looked to the bathroom door, then back to the back room.  The light was on.  I went to check and there was Jim, holding a pair of my thong underwear to his nose and one hand down his pants.

"So, you gonna take it out of your pants or cream in your undies?" I said softly.  Jim jumped, threw the thong and pulled his hand out of his pants so fast that I think he forgot to let go of his cock.  He bent over in what looked like pain.  "You okay Jim?" I asked.  "Listen, come to the living room, we need to talk right now."  'Give me a minute' Jim exclaimed. "NO, NOW" I demanded.  As Jim followed me into the living room my mind raced to figure out what to say to him.  I wasn't sure wha tto do.  All I know is that I had to fix this strange course of events.

I sat down on the couch and patted the seat next to me saying "sit here".  That's when I saw it.  I could tell that his cock must be huge in length.  I mean, I know he is young but it was no longer a bulge in his pants, it must have come out from under his undies and down his leg.  When he sat down, he couldn't even sit up straight.  He leaned back and placed his hands over himself to cover his obvious hard on.  "Oh, my" gasped.  "Sorry" Jim said, "I was, I.. I... was curious".

I didn't have any words for him.  In fact, I was so hot.  I mean, I was hot for this kid.  I gues it has been a long time.  What am I thinking, oh my goodness, this is stupid.  I want to see this kids cock and.... NO.  I have to stop.  I reached for the clicker and turned on the TV.  And of course, what channel do you think it was on.  Some chick is just riding some guy.  I was glued to that chick riding that cock.  She was moning and moning things like "ewww, yes, yes, fuck me, yes fuuuuck mmmeeee".  I just couldn't take it anymore, I looked at Jim.  He looked at me, dropped his eyes to my breasts.  My nipples were so hard and just itching for pleasure....  I was burning up.  For a kid, oh, man what was going on, I just can't do this.  I can't no, I just can't..................................................................................................................

 

Jim, do you want to touch them?  He was still staring at my nipples. Yes.  Then touch them. I reached down and picked up his hand and placed it on my left breast.  It was so hot, he was so gentle, he caressed my breast and rubbed over my nipple through my nightie and sports bra.  The sounds of the TV had taken me to another place.  

"Jim, this is your lucky night.  All you have to do is say no and I'll leave the room.  But if you want to find out what a woman wants, I'll show you" I breathed the words right into his eyes.  "Show me everything" he said quietly.

"Come with me" I got up from the couch, turned off the TV, led him all around the house shutting off the lights.  Then to the stairs where I told him to follow me up.  I know how to make my ass look good so after just a few steps, noticing he was looking down, I said "hey, my ass is up here, you may want to watch it work it's magic".  Jim looked up and a small grin appeared on his face.

I led him to my room, over to my bed and told him to stand in front of me and take off his shirt.  It only took a second for him to rip it off.  "slow down tiger, you don't need to go home till morning."  I heard a small hehe escape his lips.  "Now, the pants and remember to do it slowly" I figured that at his age he wouldn't last long so I didn't want him to disturb my enjoyment of watching his first come.  As his pants fell to the floor and he stepped out of them I realize that this was no ordinary kid.  "You have a monster in there don't you Jim?" I whispered to him.  "Now, kick your pants to the side and just watch me undress a bit for you.  And no touching the monster either."  I watched him take a big breath, then swallow as I removed my nightie.  I watched him almost tremble as I removed my bra.  "Now listen Jim, I don't want you to make a mess in your undies, and I don't want you to make a mess all over the carpet, so I need you to remove your undies carefully.  Do you think you can do it without exploding??"  I said in a very sexy tone.  "I don't know, I'll try."  "Okay" I said, "Now, if you think you can't hold back just make use the word 'yes' and I'll know you can't make it.  You see, I want your first come to be all over me.  Now are you ready to try?"  "Just a sec" as he took a number of deep breaths. 

Jim slid his undies down to his feet, kicked them to the side, looked at me and smiled knowing that he had done as I had asked.  His cock was very long, not very big around but very long.  In fact, it was over 11 inches.  I mean, it was almost as long in inches as he was in age.  This was going to be a very fun night.

"Sit on the the edge of the bed, lay back, and close your eyes" I ordered.  Jim did as I said, and quickly to boot.  I knew I didn't have much time and I wanted that come badly.  I bent over and inhaled his cock.  He jumped, it was so hot, so hard, so smooth.  I fell to my knees, his legs opened wider.  I used both hands, one caressing his balls, one stroking his cock and I sucked greedily.  I don't think he lasted 30 seconds.  His come was boiling in my mouth.  I swallowed once, twice, three times.  There was so much.  A fourth time I swallowed his come.  He was wailing with joy.  His body was so tense, then shaking, trembling, then tense again.  Then, just as he had jumped when I first inhaled his beautiful cock, he relaxed.  His cock began to soften.  I knew he needed a break but I needed that cock hard.  I needed to get off too.  I kept sucking, slurping, licking, and stroking.  And as if by magic, his cock came to life again.  Rock hard.  I looked at him, smiled and said: "I hope you don't mind but I need to fuck so bad and you have just what I need"

 Jim almost looked a bit scared but smiled and said: "I've jerked off so many times just watching you at night through your window that I can come 5 times."  So, I slowly crawled on top of him, I let him suck on my hard nipples and moved so that his hard cock was right on the entrance of my pussy.  "Jim, I want to watch your face, lay back"  As I slid down on his rock hard cock I watched exstacey roll through his eyes.  In one long push I impailed his entire cock.  Just as I hit bottom, he erupted again.  I could tell he was the longest cock I had ever had in me.  This young teen age boy with the big long dick has been the deepest.  Now he was shooting hot come all inside my pussy.  I didn't move.  I just watched him come in me.  He jerked and spasamed like I had never seen before.  All I could think about was could he keep it hard long enough for me.  I love to come but I need to get off 4 or 5 times.

 

.....  So, have you like my young adventure?  If so, vote it up.  I'd be happy to tell you the rest but right now I have to go take care of this pussy.  I'm soaked and I can't take any more.  I'll check back in a few weeks.  If I see enough interest, I'll finish the story.