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usafslut
08-01-2008, 02:15 PM
So I was babysitting for this cute little kid. This was my 4th Saturday night in a row. I didn’t mind as the kid was great and the parents were nice to me. I got to go out on other nights. It is the summer so I had plenty of time to spend with friends, girls and guys alike. I am 15 and haven’t been a virgin for almost a year, Oh I’m a girl, name is Sheryl and I pretty good looking. The night I am telling you about I was wearing a pair of jean mini shorts and a printed tee shirt, one of my favorite g-string style thongs, the kind my mom can’t understand.

So anyway the baby was asleep and after checking on him I went into their study. I had found on my second week that their PC has a bunch of porn on it and seeing as I only get these little clips when I am at my house, I was loving it.

I had been on the PC for close to hour. I had passed playing with my nipples and was fingering myself from the side of my pant leg with my right hand as I was using my left on the keyboard. I was pacing myself as I still had at least 2 hours to go.

I was in that great place just before cumming when I heard a man call “hello?” “Sheryl are you here?” I calmed down a little as the guy knew my name, but I was still in a panic as the guy sounded like he was already upstairs. I turned the monitor off quickly and pulled my fingers out of me at the same time.

I turned in the seat just as a man walked into the room. He was older than the parents of the baby and looked older than my parents, but he was a good looking and in shape, for an older man.

“I didn’t mean to scare you, I am the baby’s grandfather” he told me.

“How do I know that?” I asked. He told me the names of the family members and explained that he knew my name as he had had called his son and let him know he was stopping by the house with a gift he had in his hand. I finally relaxed.

Well, I actually only relaxed for a moment as I noticed that he was staring at my tits. I looked down myself and saw that my turned on nipples were still hard, and pushing through my tee shirt. I don’t have huge tits but I do have embarrassingly long nipples. To break the silence I , like an idiot, reached out my hand and said “glad to meet you?” He shook my hand and then rolled his fingers as I had transferred the wet from my pussy. I almost died and said quickly, “oh sorry I just finish eating a caramel.’ I was praying he would smell his hand, which he didn’t, but he saw the look on my face.

“Are you OK?” he asked.

“Sure, I guess I felt funny with you looking at my boobs” I replied.

“Oh, sorry. I’ve been divorced for about 3 years and I guess I just enjoy the female body.” he stated.

The guy was so nice and I couldn’t believe that I found him attractive. I mean I always looked at good looking older men and wondered about them in bed, especially this friend of my dad’s. This guy was just as good looking, plus I probably wasn’t thinking straight as I had been fingering about 5 minutes earlier.

I don’t know why I asked but I did ask him “so have you had many girl friends since you split up?” He looked back and said “Actually no. The whole situation took me by surprise and it took me more than a year to get over it and since then I just hang with some other friends who spend time on the golf course and in the gym.”

“Wow!” I responded, “But you’ve had sex somewhere in the 3 years right?”
He laughed, and I wondered where these questions were coming from, I felt like I was putting the moves on him.

“Yes Sheryl, I have had a lot of sex” he stated and continued after checking out my tits again “but it has all been with myself” and he put up his two hands, face out in front of him.

We both laughed. He held his hands where they were for another moment and
I reached forward and pulled them to my tits. “Here this will give you something to remember the next time you have sex with yourself.” I said as I giggled.

His hands closed around my tits and then his thumbs and forefingers squeezed my nipples. I made an involuntary moan and leaned into his grip. I really couldn’t believe I was doing this.

He looked at me and asked “Sheryl, I would love to take your nipples into my mouth, could I do that, it would be very safe and something I dream about when I see a woman like you with hard nipples?”

“Wow” I thought to myself, I don’t think I had ever been called a woman. I had already let him feel me up, so what harm could it be. Plus I really just thought he wanted to see my naked tits and this was his way of asking.
I said “OK” and took off my tee shirt. He took a long look and then leaned forward and took my tit in his mouth. He sucked gently and was flicking my nipple with his tongue. At the same time he was softly rubbing my naked back. Damn he was good. I wasn’t use to a guy being so gentle and caring as he sucked and played with me. He left one nipple and stared again at my now harder, longer nipple, and then he moved to the other and treated it the same way. I was so turned on I could feel my labia swelling and pushing against my tight shorts.

He let go and stood up and looked at what he had done and said “They really get long and hard.” The comment made me think of something else, and I looked down between HIS legs. He was wearing dress pants and there was a outline of what looked like a big cock. I said “I don’t think they are the only thing long and hard”.

I had seen 4 cocks in my life to this point and a 17 year old guy I gave a blow job to once was the biggest by far to the other 3, obviously when I fantasized it was always this cock I envisioned. But what was in his pants looked bigger, I just had to see it.

"You got to see my tits I want to see your cock it looks big" I said to him, not believing I had the guts to say what I just did.

" No” he replied, "let me just make you feel good".

" Hey I have had sex a few weeks ago, you haven't in years, besides wouldn't you like someone else's hand to get you off tonight?” I said, not having decided if I was going to do more than jerk him off.

I could tell he was still unsure so I continued "I will take all my close off if you will and you can see my young pussy!"

That did the trick. "Ok" he said "I will undress you and then you can do the same to me."

He came up to me and played with my nipples for a moment and then ran his hands slowly down my belly taking his time, which turned me on even more. He reached my jean shorts and undid the top button, I could feel him looking for the zipper but he found another silver button, he undid that one and the next and then the final one. He worked slowly which was driving me nuts.

He pulled my shorts down exposing my skimpy thong. "Wow. That is really sexy" he said.

I walked out of my shorts and did a little sexy turn letting him see my ass with the thin strap tight between my ass cheeks. He said "stop” as I was about to turn back to face him.

He put his hands on my hips and I felt him get down on his knees. I thought he was going to pull down my panties, but instead I felt him kiss one of my ass cheeks and then the other. I then felt his tongue up by the waist strap, then he curled his tongue under the strap that went down, and started inching down. Being only 15 I haven’t really gotten into anything anal and I felt this tickled more than it was sexy.

He continued down and I said with a giggle “watch out you are getting to my butt hole.” The next thing I knew he was there and started licking it like it was my pussy. I wanted to stop him, but it felt really nice.

“Put your hands on your knees” he requested.

I did what he asked, and suddenly I felt his tongue enter my ass. “Um, it may have been a while, but you are in the wrong place” I said.

He replied “No I don’t think so, I have always wanted to do this, my wife never let me touch her back here, I always wanted to be with a beautiful woman who would let me do this.” Shit this guy knew how to play me physically and mentally. I just let him go at it, and I was feeling great.
He did this for a few minutes and then pulled away and pulled down my panties and I stepped out of them. I turned around and he was still on his knees. I could see he wanted to eat me out, so I took a step back. He looked up at my face and said “I have never seen a shaved one before.”

I was almost feeling sorry for the guy, but at this point I wanted to see his package. I looked at him and said “well I haven’t seen a big cock either, it’s my turn.”

He stood up and I walked up to him and unbuttoned his shirt and took it off, I reached down to his belt and undid it, then I went to unbutton them. I realized then that I had only undone boy’s jeans, I didn’t get the hook and button and contraption he had. I reached my hand in his pants a little to undo things and my fingers rubbed against the head of his dick. “Wow, it comes all the way up here?” he just smiled, then he helped me out and undid the inside button.

I unzipped him and pulled his pants down. He was wearing boxers. I got on my knees and helped him step out of his pant. I took a breath and then pulled his boxers down. His cock almost hit me in my face. It must have been 8 inches and thick. It was probably twice as heavy as the guy I use to fantasize about.

I wasn’t sure what I wanted to do, but I figured “what the fuck” and put one hand on his shaft and took the head into my mouth. It took me a minute of two but I finally got more of him in my mouth and started sucking him off.

The first words out of his mouth were “oh my, you know it has been over 30 years since I have gotten one of these.” I kept working the huge pole and thought to myself “the last time this guy got a blow job was twice as long as I have been alive- sick.”

I was sucking for a few minutes when he tugged me under my arm pits and lifted me off him and up to my feet. He looked into my face and said “you are making me feel great, but I would really like to make you feel good tonight.” He walked me over to the dresser that had the baby’s changing pad and stuff. He moved some of the items to the side and then helped me up. I sat there with my legs open and dangling over the side. My pussy was right there for him to see. I was totally wet and puffy down there and smiled as he spread my legs further apart.

He then leaned in and started to eat me out. He was slow and gentle like he had been with my nipples, only this was really driving me crazy as I wanted his finger or even that big cock inside me. He pushed me back a little so my back was up against the wall and he lifted my feet so they were on the dresser top. He started licking me again and then went south and started licking my butt hole again. My pussy needed to be filled and this guy was back to licking my ass, but it really felt good too.

His hands started to massage my legs down by my butt and then he moved his mouth back to licking my pussy and his thumb moved over to my butt hole, it started to circle the hole and then I felt it slide into me. I wanted it in my pussy, but it actually felt good where it was. I was totally on fire and I lifted my ass off the wood a little. I could actually see him smile as he was eating me.

He had his thumb totally in my ass and he was pushing in hard circling his last joint in me , I think it was like having two fingers inside. I couldn’t believe it, the only thing I ever had up there was a thermometer.

He moved his mouth over my clit and started to suck on it. No one had ever done that to me either. It was outrageous and more then I could handle. I started bucking against his mouth and I was panting and breathing loudly. I brought a hand up to my mouth so I wouldn’t wake the baby. I was cumming wildly.

The guy used the fluid pouring out of cunt to lube his fingers and my other hole and the next thing I knew he had two of his long fingers deep in my ass. He was pounding his finger in me like it was my pussy. I couldn’t believe they fit, nor how good they felt. I was still cumming and my body wasn’t coming down. He was licking me all over and sucking my lips and clit as well.
He moved his mouth off me a minute later and slid his thumb into my cunt. He now had three fingers in me, in two different wholes, I was still cumming. He looked around the table and then leaned into one of my tits and started sucking. I thought I was going to scream I was in such a fucking great place.

I looked to where his other hand was moving and it was searching for something on the table. He finally grabbed a bottle of baby oil and brought it down between my legs. I couldn’t figure out why, but then again my brain was somewhere else at the moment.

I heard the cap flip open and suddenly I felt the fingers in my ass sliding in much more freely and I could feel the oil outside and then inside my hole. A moment later I felt more pressure inside my butt as I think he added another finger. I finally spoke and asked “do you really have all those fingers inside me?”

He moved his head away and sure enough I was looking at his thumb in my pussy and his other fingers in my ass. He looked at me and said, “you have one of those asses that was made for fucking, it loosened right up and it seems to want more than my fingers.”

It took me a moment to resister what he was saying. “are you saying you want to put your huge cock in my ass?” He looked back and me and said “look beautiful one, I have 4 figures in your ass, that’s wider than even my errection, and your body is sucking them in wanting more.”

I couldn’t figure out how he knew that, but he obviously had a lot more experience than I did, I couldn’t tell that my body wanted more. All I knew is that I wanted to be fucked and didn’t want to stop cumming.

“What should we do now? I asked.

The man took his hand out of me and lifted me off the dresser. He put me on the floor and then grabbed the bottle. He grabbed one of the pillows that was sitting on the dresser as well and put it under my butt. He was like an expert and I was going along with it. I looked again at his cock and right now it looked huge knowing where he wanted to put it.

He got between my legs and licked my pussy again and sucked my clit till I was squirming. I heard his pop the cap again and I yelled out “wait, I need to feel it in my cunt first, please, please.”

He moved up my body and started to suck on my nipple, somehow he had moved up and had my ankles over his shoulders. As he moved further up and was kissing my neck, my body had shifted and my butt was hardly on the floor. I felt his cock up against the back of my thigh, rubbing up and down, it was hard and big.

He shifted his hips and the heavy dick landed right on top of my pussy. He backed off a little and I felt the head at the opening of my cunt hole. He moved forward and I felt the head slip into my very wet hole. He moved slowly and I could feel my cunt lips spreading and the stretching as inch after inch moved into my cunt. I think I started to cum again before he was even half way in. As I started to cum he started to pump inside me. I was so filled as I felt his balls hit my butt.

He was fucking me for only a couple of minutes when I heard the bottle cap open again on the oil. I felt the liquid being spread by a finger and then it pushed into me. I felt more liquid and then another finger. His fingers in my ass seem to make my pussy lips even tighter around his meat.

A minute later he pulled his cock out of my pussy. I looked down and it was soaked in my cum, he squirted oil on it which made it even wetter. He positioned it over my ass and pulled his fingers out. He quickly replaced his finger with the head of his cock and pushed it inside me a couple of inches.

Even with all the lube I got this shocking pain from my ass to my head.

“Take it out it hurts” I yelled.

“Quite, you’ll wake the baby” he replied.

“Fuck the baby, take that thing out of my ass.” I yelled again.

“You have to relax, it will feel good I promise, but you have relax, your body will take it even if you don’t but it will get there quicker if you help it.” He said calmly. He rolled forward to get my ass off the floor more, but in doing so his cock went me even deeper.

“What that fuck are you doing you crazy old fuck” I didn’t get a chance to finish as he put his mouth over mine and started kissing me for the first time. I put my head back to get away from him to continue yelling, he had me pinned in this position and I couldn’t push him off. As his head moved down to stay linked to mine the damn cock when in another inch or so.

I was really pissed and about to bite his tongue when I felt the muscles in my ass unclamp his cock. It was wild they were tight and I was in pain one second and the next I felt like my ass just became this big deep hole like the inside of my cunt.

“There, you see.” He said, obviously he could feel the clamping muscles relax to. He didn’t wait more than a few seconds and he started to pump me. He was pulling out a little and then in deeper. Feeling him rubbing inside me felt great, I couldn’t believe it. He leaned in and kissed me again and this time I returned the kiss. He was fucking my ass like it was my cunt and I loved it.

A few minutes later I got this great feeling and suddenly I was cumming from my ass. I was screaming to him to fuck me fuck fuck me- and he reminded me to quite down. I tried by burying my mouth into his shoulder. I was cumming hard, it was different but I was still cumming.

Not much later, he was moaning and stated “I am going to cum, Sheryl, I need you to know I cum a lot.” I was still cumming and panted out “Are you going to cum in my ass?” I never had a guy cum in my pussy without a rubber and wasn’t sure about my ass. I loved when I jerked guys off as I loved playing with their cum.

A moment later he said “no not inside you.” He then pulled his cock out of my ass, his hands were still on the floor with my legs over his elbows. I lifted my head the best I could and saw the thick head of cock point right at me and then, without even touching it; his cock started to spit out his cream. The first shot hit me right on the chin, the next my neck, and it just kept spurting, I don’t know if he was doing it with his muscles or the dick was doing it on it its own, but it was bouncing and then firing, he just kept doing it and before I knew it he had shot about 10 shots of white cum all over my body. I couldn’t help but lick the one of my chin so I could taste him.

I was in heaven. He finally stopped and moved so I could move my legs to the floor. His dick hole was still dripping with cum. I grabbed the pack of wet ones that was in reach and wiped his cock, except for the head and then I took it into my mouth. I sucked on the head and got about a half a mouthful of the cum left in his shaft. He wasn’t kidding about cumming I was covered. I put the wipe on the floor for a minute and used my hands to rub his cum all over my body, I rubbed it on my tits and belly.

He saw how turned on I was with all his cum so he helped me out and drove two fingers back into my cunt and within a minute or two I was cumming again. He got me off for a few minutes and then pulled out and stood up. He looked at me on the floor and said “I have never done that before.” I asked “done what?”

He said “had sex in that hole.”

“Bullshit” I replied, “you knew exactly what you were doing with the oil and everything?”

He smiled and said “all from reading” I laughed and said “You have to get me that book!”

We both got dressed. I used a ton of the wipes to clean up so I didn’t drip his cum and after he left I actually showered,

What a night of baby sitting, one I hope will get repeated.

Sheryl

(check out my blog)

davesmistress
08-01-2008, 07:45 PM
Thanks for the addition

dribblensqirt
08-21-2008, 08:57 AM
Such a great story. Reminds me of when I used to babysit.

manjuice
08-22-2008, 08:57 AM
good effort

Sadistic
09-15-2008, 04:26 PM
That was really freakin' hot. The way you describe the scenes without rushing.. take notes

Luckymann
09-15-2008, 07:38 PM
Loved the Babystiiting story USAFslut. It brought back memories of when I used to vistit my babysitting GF. The same girl in My First Lover. She and your babysitter were horny young sluts. I too enjoyed your slow progression. It added to the excitement of your story.

hornyslut
09-15-2008, 07:52 PM
Loved it!

aaronakafidel3
09-15-2008, 07:56 PM
I really enjoyed it, like I do all your stories...keep up the great work!

1bigduke
09-16-2008, 08:03 PM
Was a wonderfully erotic story. Got hard before than the grandad did..

Great story.

kookiekittie
09-20-2008, 10:39 AM
That is a wonderful story. Had me dripping wet from the get go.

dr.bob
09-23-2008, 01:32 PM
an excellant story...thanks for posting

peajay2k
10-10-2008, 09:05 AM
another great story

kmakaz
10-12-2008, 06:15 PM
excellent - loved it!

littlestormy
10-15-2008, 11:49 AM
babysitting can be so rewarding,and a hot little babysitter with a cute little ass is even better.

hornknee1
10-16-2008, 09:55 AM
Let me tell you that was one great story. makes me want to have kids just so i could get a babysitter and maybe something like that might happen, again great story :)

swurvy
10-29-2008, 04:54 PM
Another great story! I loved it! Great work as always!

hotlvr
10-30-2008, 10:17 AM
to bad I did not have a very good babysitter. I would have kept her

ruamano 1331
11-02-2008, 04:16 PM
Usafslut, the way you write is amazing, I swear, I could damn near smell her pussy juices wafting up into my sensitive nostrils. I need to taste slippery and thick creamy pussy again today. Thanks.

s_n_t4fun
02-19-2009, 02:09 PM
I have always thought the babysitter would be fun

jollyman
02-27-2009, 03:16 PM
Good story

NaughtyOne
02-28-2009, 08:06 PM
Great story, thanks for sharing

member37
03-01-2009, 11:56 AM
Thank-you very much. sexy story.

twojustfourfun
03-01-2009, 12:12 PM
Great story! Is it just me, or do these type of stories get me hotter because I'm older?!? :)

Bindncuftite
03-01-2009, 12:16 PM
Geez, what a story. Where were you when I needed a babysitter for my kids. Well done.

frankjohnmoore
03-04-2009, 09:30 PM
grate story, had me going

PrinceTroll
03-06-2009, 12:08 PM
Lucky old guy...

TNTrp
03-06-2009, 05:52 PM
Wow, super Story!

Ricey
03-07-2009, 01:51 AM
Great story, very hot and steamy

pdiddystonec
03-10-2009, 01:57 PM
wow that was a great story

cookinguy
03-17-2009, 03:36 PM
That was a really great story. Really got me going, if you know what I mean.
;fireball

icqwerty
04-13-2009, 11:50 AM
great story

lucidmez
04-20-2009, 02:48 PM
Wow, another hot story. There hasn't been one I didn't like.

sydneycd
06-05-2009, 10:18 AM
really great story, left me a bit wet

comsmith22
06-05-2009, 07:26 PM
Good story ... really hot ... thanks again for another one of you amazing story
:hwl:pengy::fade

wadave
06-08-2009, 08:19 AM
you can sure write a great story.. hot and sexy all the time thank you

pedro
06-09-2009, 10:48 PM
That was great, thanks a lot.

saltydip_50
06-11-2009, 02:16 AM
amazing story ... more please

txsurfer13
06-12-2009, 11:50 AM
Damn sheryl, that was incredible! One of the best I've read here... thanks!

NaughtyOne
06-12-2009, 04:27 PM
I really enjoyed your storie...keep up the great work! and thanks for sharing

ohiomikep
07-20-2009, 05:25 PM
wow - that was smoking - love those babysitter stories - wish I had babysitters like that!

ironeagle2
07-21-2009, 07:31 PM
good one

SUCKmyCL1T
07-30-2009, 10:02 AM
Another great sory Sheryl! Always love to read your posts. They leave my pussy dripping xoxo

redvis57
08-01-2009, 09:46 AM
Oh yes, babysitting stories can produce some mighty fine memories and fantacies. Thanks.

M of Cheshire
08-03-2009, 04:44 AM
You certainly know how to write a good fantasy

Kojack1978
08-04-2009, 11:30 PM
Good story, please keep up the good work

burral3
09-27-2009, 12:52 PM
I need a babysitter like her. Loved the story

randy66
09-27-2009, 08:12 PM
good story but seems to need more

kaptainkaos
09-28-2009, 07:08 PM
wow great story!! thanks for sharing that with us!

latino 07
09-28-2009, 08:56 PM
now that a story with heat wish i could find a babysitter like her

am_cutie666
10-02-2009, 02:48 PM
thnks for the story.....really good...

lazystoner
04-28-2010, 07:02 PM
great story, hope to read more. Thanks

missingrandy
05-07-2010, 07:40 AM
dripping wet

Drake1965
05-07-2010, 09:18 AM
Wish you would come and babysit for me!! Great story!

12sam
05-08-2010, 05:59 PM
Great story!!!

ssixg
06-12-2010, 01:47 PM
Sweet story, thanks for posting!

Styleshbk
06-16-2010, 09:50 AM
Great story

Purple_Monkey
06-19-2010, 08:22 AM
I really enjoyed the story

youngandwet17
07-09-2010, 10:40 PM
this story is so damn hot

twistedinsomnia
07-10-2010, 03:50 PM
Very interesting! Nice!

dingo
07-18-2010, 05:37 PM
great story! got the juices flowing

Tanaka271
07-19-2010, 04:46 PM
nice story!

lovelqqkn2
07-20-2010, 06:08 PM
Very Hot story. I love the grampa angle instead of the father, makes the story even hotter.

theatreslut
07-30-2010, 10:10 AM
very wicked

LordDarkStar
09-07-2010, 03:29 PM
Marvelous story, USAFslut. Really love your stories that I have read.

Nomad
09-08-2010, 11:12 PM
great story, thank you for shring, looking forward to some more adventures fromyourself

PonderaXD
10-17-2010, 09:28 PM
Hot. Very, very, hot.

dumbo
10-18-2010, 02:46 AM
excellent story, keep typing!!!
REally enjoyed it

storyboy69
10-18-2010, 03:26 AM
great story, really liked it......thanks...

reckless33
10-19-2010, 08:12 AM
goood story

reckless33
10-19-2010, 10:08 AM
hot story

the_mad_am
10-19-2010, 01:06 PM
simply delicious!!!

Schnepfe
11-24-2010, 01:33 PM
Nice reading! Thanks

easyboy
11-29-2010, 04:23 PM
Another superbly hot story.

sexibibabe
12-02-2010, 12:40 AM
I wish I could have had a babysitting job like that one!!!

davidbannano
12-30-2010, 07:44 AM
great story

ScorpioStud
03-14-2012, 06:14 AM
WOW! great story

D0ggy
11-23-2012, 10:16 AM
Great, i´m hard...

kingwolf
11-23-2012, 09:22 PM
would of liked it more if there was more pussy action. but decent story i suppose.

Bella 25
12-26-2012, 12:40 PM
Nice story. I should have babysat more.

hillbillyrednek
12-26-2012, 05:02 PM
wows

Geno
03-12-2013, 12:50 PM
You have a wonderful gift of storytelling. I wish I could do half as well

hawkoftheknight
03-15-2013, 02:35 AM
Great story!!!!

hippeh
04-10-2013, 03:58 PM
amazing story and so well detailed

PaulTheTeacher
06-07-2013, 02:51 AM
mmm makes me wish I had kids of my own just for the sitter!

actionmaster6
07-14-2013, 07:42 PM
Wasn't expecting it to be the grandpa. But a good story none the less.

Youngatheart
07-05-2014, 08:16 PM
Really enjoyed your story. Thanks so much for sharing with us.

megan
07-31-2014, 05:11 AM
I managed to get the babies daddy to fill me up when he drove me home the second time after I sat for him. A week later I was asked to sit again but this time it was to babysit him and his wife. That was the first of many big threesome nights with them. We had a few more threesomes which were wonderful after that. I cheated with his wife al couple of times as she loved girly sex as much as I do.

BadPops
01-13-2015, 05:40 PM
New here and I'm glad I read this one. Very hot and I hope someday to have this fantasy. ;)

ironeagle2
11-02-2015, 02:01 PM
still a great read

scotty2hotty
06-13-2016, 05:47 AM
as always.... great story