Babysitter Sex Stories

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Note : This story is completely fictional!
I had been babysitting Joey and Laura for about two years. The Smiths were
my favorite family to work for, since they payed twice as much as my other
employers. Besides, Mr. Smith was a pretty good looking guy and it gave me
food for thought. Even at age 11, Joey still needed a babysitter. Why,
when I was 12 I was watching kids. Still, I was 18, 7 years older than
Joey, so I was able to exert the needed authority over him. Joey's twin
sister, Laura, seemed less in need of a sitter, she was rather mature.
On new years eve, when the Smiths wouldn't be home until late the next
morning, I figured I could really explore their big house. Kids were in bed
at ten and I was starting to get bored. I walked into the basement and
found a box of old porno rags. I flipped through one took a look at some
of the pictures. There was one with a woman spread legged and her vagina
shaved. She held a vibrator close to the pussy lips. Another picture
showed a woman sitting. Between her legs were two penises, one in her ass
and one in her cunt. A third penis was in front of her face and her tongue
grazed the top. Another magazine showed pictures of nude women performing
sexual acts, oral, anal, vaginal, on one another. The idea of me being
with another woman sexually turned me on a bit, but I dismissed it when I
heard some sounds above. I carefully but quickly returned the magaizines
to their place and slipped upstairs. I could hear talking of some sort
coming from Joey's room. I walked down the hall and peeked slowly opened
the door. There, in his bed, was Joey. He was naked and straddled over a
life size doll. In fact, it was a doll that I remember seeing in Laura's
room. His hand was rubbing his penis, which was larger than I would have
expected to see on an 11 year old. It stuck out from a reasonable thick
bush of pubic hair. Alas, this boy who needs babysitting had the prick of
a man. I watched quietly as he picked up a plastic sandwich baggie and
placed it over his cock and wrapped it around. He then took the wrapped
penis and put it between the doll's legs! He slid up until his pubic hair
touched the cloth crotch of the doll. He then started to fuck it. He
bounced up and down and slid back and forth on it. He rubbed the two small
cloth mounds that make up the doll's fake breasts. I thought about my
first time. I was 16 and was under pressure from my friends to do it.
Turns out, none of them ever had and they called me a slut after I did it
with some guy I met at a party. Funny, I enjoyed it. But because of the
name calling I got, I never went all the way with a guy after that. Joey's
plaything made me think of all I've done to get rid of sexual stress. I've
fingered myself, used objects like bananas, and the like. Joey's use of a
cloth doll made me think of the penis that I had constructed from some
velvet and pillow stuffing when I was 17. I would slide the soft pillow in
and out of me while pretending it was Mel Gibson or someone of the like.
It would get yucky with my lubrication, so I would make another. Each
time, it would be a little bigger and with more stuffing.

"I'm going to come in you baby," moaned Joey. He was bucking his hips
faster and faster until his butt clenched. He was exhausted and placed his
chest against that of the doll. He rolled off after about a minute. The
plastic bag stuck to his cock. He carefully pulled it off, white goo
sticking to the bag and he prick. He picked up a tissue and wiped off his
penis. He pushed the dirty tissue into the baggie and wrapped the plastic
into a a paper bag and put the paper bag into his backpack. He then picked
up the doll and, still nude, came over to the door. I was able to move
into a doorway just in time. He slipped into his sleeping twin's room and
returned without the doll. He went back into his own room, put on his
PJ's, and went to sleep.
I was horney as Hell by this point. I remembered seeing a bowl of fruit in
the kitchen. Lucky me, there was a banana. I took it in my hand and
slipped into the bathroom. I lowered my jeans and panties and sat on the
toilet seat. With my legs spread, I slowly pushed the yellow fruit into my
crack and pumped it while I dreamed of being fucked by a faceless man with
a huge cock. I came quickly. I pulled out the banana and looked at it.
Covered with my female cream. I took a paper towel and wiped if off.
Perfect! I put my pants back on and put the fruit, no worse off than
before, in the fruit bowl.
I was invited back to sit the next weekend. You know, those post new years
eve parties. Anyhow, I was really excited about going because I now knew
about the porno rags. Besides, the fact that I had fucked myself with a
banana and then put it back where someone, maybe Mr. Smith, would eat it.
Sure enough, the banana was gone (it would have been black and mushy
anyway). At ten, Joey went upstairs to take a bath. Laura had just gone
to bed. When I heard the water stop, a quietly crept upstairs. From
within the bathroom I could hear water gently splashing. I very quietly
opened the door a crack. There, standing in the tub, was Joey. Once
again, he was naked and had that beautiful stiff cock. In his hands was a
bar of soap, which he was lathering. He then lowered the sudsy bar to his
penis and started to rub it, covering it with the rich lather. He coated
his pubic hair with the white suds. When his groin was totally white, he
dropped the soap into the water. He then stroked with his hand along the
slippering rod between his legs. I was turned on. I really wanted a fuck.
So I did the amazing. I shouldn't have. He was only 11. I stepped
inside.
"You know, you don't need to fuck your hand when you have a real woman in
the house," I said in calm voice. Very natural. He quickly dropped down
into the tub and covered himself with his hands.
"Don't worry... I won't tell. Well, that is if you help me." He looked
confused. To demonstrate my point, I kicked the door closed. Quietly
enough so as not to wake Laura. I then pulled off my sweater and tossed in
near the door. I slowly opened my top and tossed it along with the
sweater. Joey was looking at my chest, covered with a bra. I'm neither
big nor small. I unsnapped my jeans and pulled then down. Here I was,
standing in front of an 11 year old boy wearing only my bra and panties. I
must have been crazy.
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...continued... I'm secretly watching my gorgeous wife, Katie, sunbathing in the garden - she has just agreed to let one of a troupe of hunky, young builders from next-door rub sun-oil into her back...
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I was driving home from work the other day and I saw my 11-year-old babysitter walking down the street. I live in a relatively isolated rural area and she was walking on the side of the road. She is the most beautiful little girl and she was walking slowly on the roadside facing traffic in a sexy outfit.
She has shoulder length dirty blonde, almost brown hair that was tied in pigtails, and she has braces. She was wearing a gray, form-fitting top that was showing her tiny boobies that were beginning to grow and was not shielded by any bra today. She was also wearing a little gray and white skirt with stripes that were short but not too short. I slowed down as I drove past her and she looked up and saw me looking at her and she smiled and waved at me as I pulled up and stopped rolling down the window as I stopped the car.
She bent over to talk to me through the window. When she did that the top she was wearing fell forward showing me her tiny developing titties that were hiding underneath. She smiled and said, “Hi Mr. Michaels!”
“Hi Amy, how are you doing?” I said admiring her swollen nipples that she was exposing to me. I had on dark sunglasses and was sure she could not see my eyes as I ogled her young body but it was obvious she was not intending to show me her goodies. “Do you need a ride somewhere?”
“Oh thank you, Mr. Michaels, that would be great! I walked all the way from Wally World!” She said as she opened the door and jumped into my car and closed it. She smiled at me and said, “Let’s go!”
I smiled and drove off slowly towards our neighborhood. “So Amy what did you buy today?”
“Oh I can’t show you, they are kind of personal.” she replied blushing.
“Where did you get the money for the new items Amy?” I said knowing I had just paid her for babysitting on the weekend and expected it may have been from me.
“Well Mr. Michaels, it’s from the money I earned at your house last weekend.” she said smiling at me.
“If I gave you the money, you kind of owe me to at least show me what my money is buying for you,” I said.
“Okay Mr. Michaels, but don’t say I didn’t warn you!” she replied taking the first item out of her bag. “I needed a training bra. My boobs are starting to get bigger and my Daddy said it was time for me to get one last night,” she said. She took out the plain tan training bra and I looked at her smiling as I decided to pull over the car so I could pay more attention. She reached in again and took out three pairs of nylon panties and showed them to me. “I made enough on Saturday to buy some new undies. I love these nylon panties; they feel so good when I wear them. Do you like them?” She asked as she held them up and showed them to me pulling them against her chest with a big smile on her face.
“I love them. But isn’t that one a thong?” I asked pointing to one of them.
“Oh yes. I love thongs. My butt looks so much better in some of my clothes when I wear a thong. I’m wearing one right now Mr. Michaels and look…” she said as she unbuckled her seat belt and turned over in the seat and aimed her ass towards me showing me her perky butt. “If I wasn’t wearing a thong right now you would be able to see my panties! Isn’t this better?” she said smiling at me teasing me with her body.
“Amy, I’m not going to lie to you. Your ass looks spectacular in that skirt. So whatever you are doing! Keep it up!” I said smiling at my underage babysitter.
She turned around and leaned over and kissed me on the lips, then she buckled her seatbelt and giggled. “Thanks, Mr. Michaels.”
“My name is Paul Amy. When we are alone you can call me Paul. Okay?”
“Sure Mr… I mean Paul.” She said and she giggled again. I was so turned on by this little nymph and I had a full hard on as I put the car in Drive and went back down the road. I shifted uncomfortably and she looked in my lap and she reached up and adjusted her glasses and smiled at me and said, “Oh Paul, did I do that to you?” she said pointing at my hard cock.
“Well… Amy… to be blunt yes you did.” I said as I continued driving.
“My Daddy said that when a boy gets all hard like that he is excited and wants to have sex with you. Do you want to have sex with me, Paul?”
“Why yes Amy, you look really sexy today and you just showed me your new underwear so yeah you made me horny,” I said looking at her body. “And your body is so sexy and you are so cute how could I not?”
“OMG Paul, my Daddy told me I needed to get a training bra today or things like this would happen. I didn’t believe him but now I do!” she said. “I’ve had a crush on you since I started babysitting for you…” she said smiling at me.
I pulled the car over to the side of the semi-deserted road and turned and looked at her. “Oh yeah, Amy? I didn’t know that. So what are we going to do about this? I asked the pretty girl hoping I wasn’t pushing too hard.
“My Daddy isn’t coming home until late tonight. Are Max and Julie at their Mom’s this week?” She knew they were since they weren’t in the car with me. I nodded and she giggled. “Can we go to your house?”
“Pizza?” I asked as I dialed the pizza place. She nodded and I ordered a pizza for delivery and finished the drive home. I had a hard on the rest of the way home that was mostly silent. She gave me a few goofy glances and I could tell she was as excited about the possibilities as I was. We got to the house that was only a few minutes away from her house and I pulled into the garage and closed the door behind us giving us privacy from the street. We unbuckled out seat belts and she turned and looked at me smiling from ear to ear.
I smiled back and said, “Can I kiss you?”
She nodded enthusiastically and said, “My best friend and I have been practicing together!”
“Oh yeah? Does that make you horny when you kiss your best friend?”
“Uh huh, we get butterflies in our stomachs but then we aren’t sure what to do next.” She said smiling at me as I moved in for a kiss.
I kissed her cute sexy little mouth and her hair was in our way. I moved her hair back tucking it behind her ear.
I slid my tongue into her mouth and she took it in willingly and kind of sat there not knowing what to do. I went after her tiny tongue and she reacted as I found it not knowing what to do. Her innocence was such a turn on. I circled her tongue and she began copying my movements. She was holding her breath and after a minute, she broke our first kiss and was gasping for her breath.
“Let’s go inside sweetie and get comfortable on the couch!” She nodded and we went into the house me in the lead and I had her by her hand leading her into the house. She was so tiny. I pulled her inside and she took the lead into the kitchen and I admired her tiny cute ass as she walked inside. I pointed to the sofa and told her to make herself comfortable. I walked to the big window that was open and I closed the curtains and smiled at her as she waited for me to finish. I did and I joined her on the couch and she reached for my face and kissed me again. “Ok, some pointers, don’t hold your breath. Breathe through your nose and just do what I am doing and enjoy the kiss.”
She nodded and I leaned in to kiss the girl again. This time, she did as I said and she was kissing me better than before. I moved her off the couch and put her in front of me and patted my lap guiding her to straddle my lap and she ended up on top of me. She looked down at me with her pigtails hanging in my face and we kissed some more. It was making me hornier and I moved my hand on her back rubbing her and I slid my hand up her skirt from behind rubbing her ass. She moaned as I touched her and soon she was really kissing me deeply going after my tongue savagely. She was learning fast. Suddenly the doorbell rang.
“Oh no!” she said gasping and looking at the door with a worried look in her eyes. “Who do you think that is Mr. Michaels?” She dismounted me and sat on the couch looking scared.
“It’s okay Amy, it’s just the pizza we ordered, I said walking to the door. It was then I noticed her nipples were hard under her top. She looked as erotic as any girls ever have before. I opened the door shielding her with the door so the pizza guy couldn’t see her.
“Hi!” he said as I opened the door. “$12.50,” he said handing me the pizza. I took the box and turned and put it on a small table by the door and he reached in and pushed the door open more. I think he wanted to see who was with me. The same pizza boy has delivered to be before with various women on the couch. I’m a divorced man and I frequently have sexy women over and pizza is a good way to introduce food when I want to fuck and not cook! He peeked in and saw sexy little Amy sitting on the couch in her little skirt, tight gray shirt with hard nipples poking thru and her hair in cute pigtails. She sat on the end of the sofa smiling at the boy and I turned back and noticed that he saw her. He smiled and nodded at me I’m sure he figured out that she wasn’t my daughter and he knew what was going on.
“Keep it,” I said handing him a twenty. He smiled and motioned his gratitude on the big tip and ran down the sidewalk to his beat up Honda Civic. I closed the door and said, “Do you want to eat?”
“Uh uh,” she said shaking her head slowly smiling at me as I closed the door. “I want to kiss you some more Mr. Michaels.”
I put the pizza box on the kitchen table and returned to her. I sat next to her and she immediately got up and straddled my thighs again mounting me the same way she had done before. It was very hot. She was extremely excited and she was ready to play more. “I like you calling me Mr. Michaels too so you can continue. I want to define some rules before we go any further okay?” She nodded waiting for me to speak. “I will teach you all about sex. I will show you things that you have only heard of and you will receive more pleasure than you have ever known before. I only ask a few things in return.
“I’ll do anything you want Mr. Michaels.” She said cupping my face with her hands kissing me again.
“That’s good because that’s one of the rules. Whatever I say you do, you have to do it. Second, I am in charge. What I say goes and you do anything I ask without question. You also have to promise me that you will never tell anyone anything about what goes on here. That is very important. If anyone heard that I was playing around with my 11-year-old babysitter, my bitch of an ex-wife would have me thrown in jail and take my son and daughter away. So it has to be our little secret. Do you understand?”
She nodded and reached up and sexily crossed her chest with her index finger pointing to her little boobs. “Yes Mr. Michaels, I cross my heart and hope to die. I’ll never tell a soul!”
“Good!” I said as I reached up and pulled he to up exposing her swollen pink nipple exposing the young girl’s developing titty to me for the first time. She watched as I exposed her nipple smiling down at me. I moved in and took her nipple into my mouth and sucked it gently. My tongue rolled around the hard nub in the middle and she gasped feeling her flesh being treated so gingerly. She pulled my head into her chest more and I put my hands on her back pulling her closer too.
I pulled back and looked up at her as I did the same to her left side and pulled the top down over her nipple, this time, I pulled the top all the way off and tossed it on the floor. Now she was completely exposed to me and she pulled my face towards her second nipple. I took it into my mouth and treated it with the same pleasure as I did before. This time, I rubbed her naked back as I did. This gave her goose bumps on her back and I knew she was enjoying my gentle stroking.
I moved my hands up and down her back and ended up again at the top of her skirt and this time I slipped my middle finger into the crack of her ass sliding it down as far as I could. She squealed as I did so and she pulled my face off her breast and kissed me again deeply. I kissed her for about a minute then I stopped and I led her off my lap and I stood up from the couch and looked down
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