Babysitter Fantasy Stories

Babysitter Fantasy Stories
Stories from days past, you can find masterposts for series here about older stories, you can also post your favorite older stories here as well, be sure to credit the author.
More Stories wrote:
Jacked Off by the Babysitter by More Stories

When I was a teen my little brother and I had a babysitter watch after us when my parents went out. I personally felt like I was too old to have a babysitter, but since I was known for being a troublemaker, and I was stuck with a younger brother (11) too I was condemned to being babysat even at my age. Fortunately, we had a hot looking babysitter named Nancy, who was 18 with big firm boobies, green eyes and beautiful auburn hair. In front of my parents she always acted all calm and proper, but when my parents weren’t home she was a very different person. She would let us do a lot of things that my parents would never approve of like stay up and watching grown up programs on cable that had bad words and nudity, eat junk food, and even teach us dirty words. She knew I was a horny little devil and liked to tease me in different ways.

One night when babysitting us we were playing cops and robbers with my little brother to entertain him. We would take turns, one person being the policeman, and the other being the robber wearing a ski mask. We used the whole house, and with the lights off the robber would have to sneak into rooms and steal stuff putting it in a pillowcase without being caught. The police person would go through the house one room at a time looking for the robber. If you didn’t listen, and hide really good the policeman could find you and arrest you. We had these cheap handcuffs that were actually made from metal, but had a little hidden safety latch on them. Funny thing is it was really hard to reach the release latch if you were the one handcuffed.

One of the times when I was playing the policeman, and she was the robber, I caught her in the den hiding behind the couch. I got to arrest her and “play” search her for anything hidden on her or in her pockets. She let me reach under her shirt and feel her breast through her bra, and reach into her jeans pockets. I even tried to unbutton her pants and got as far as unbuttoning and unzipping them before she stopped me saying that was far enough. Seeing the top of her little white panties with a red elastic waistband and little colored dots on them made me really horny. Her smooth skin and flat tummy drove me wild. I wanted to do more but she would not let me.

We had been playing for a while so around 9:30 she told my brother it was bedtime. He didn’t want to go to bed and was being a brat about it. She ordered him to get into his pajamas, but said I could stay up longer. She put my brother to bed, and I went to change. She was sitting on the couch watching TV when I came out a while later in my lose-fitting pj’s with stripes on them. As soon as she saw me she started laughing poking fun at my pajamas. Feeling belittled I threw a fit and jumped on her trying to overpower her. I was trying to pin her down to the couch but she was stronger. In all the struggling and wriggling around together I got excited. I wasn’t wearing any underwear and with all the close contact I got a raging hard-on in my pants. Then she rolled me over on my stomach and managed to handcuff my arms behind my back! With my hands behind me I could not reach the little release catch. I was stuck handcuffed with a hard-on grinding against the ground now! I mean it got rock hard. She said she was going to spank me like a little baby if I kept misbehaving. I didn’t care. Then things got even worse (or better depending on how you look at it). When she rolled me over again to talk to me the head of my erect penis popped out of my pajama fly! I was so embarrassed that my face became hot. She stared wide-eyed at my helpless twitching penis as I lay there powerless to do anything and reached down and grabbed it by the shaft. I guess I have a pretty big dick for my age and she seemed to be very impressed with it. “Oh my!” she said with a sly tone in her voice. “Well we are a very bad boy aren’t we?” I was really embarrassed but really turned on too at the same time and just stood there speechless. Forcefully she pulled me over her lap on the couch with my shoulders propped up on the end of the couch. She pulled my pj pants all the way down and reaching underneath she started stroking my super hard dick with one hand, while spanking my naked butt with the other. “Bad boy!” she kept playfully saying while she lightly spanked my butt and stroked my dick. My dickhead now got wet with precum that she used as lube to stroke me ever further. She spanked and stroked me as I moaned in ecstasy till I arched my back and jutted my hips forward spurting all over the couch pillow! I was really embarrassed after, lying there handcuffed and bottomless with spooge all over me & the couch. She made me promise to not ever say anything about it or she would never baby sit for me again. I eagerly agreed. The she cleaned the couch off and flipped the cushion and told me I needed to go to bed.
Janienudiepants wrote:
Babysitter by Janienudiepants

Very nice story. I babysat a lot for my mom's divorced friends as a teen. Mainly single moms, occasionally everyone else. I dreaded some kids, and others I lived to die for, they were so cute. One pair of boys were four and seven, a bit like you, and cute as h*ll. At bedtime one thing you knew for sure who had a "hard-on." Their little flagpoles stood out of their pj tents once they found the hole. Of course, little boys button pjs have a huge hole in front -- they never button them, and their little d*cks found it all the time in tickle fights, wrestling playing around with them before bed or just sitting with me snuggled up watching TV. I grew up with the impression boys always had a hard-on.

I always enjoyed the cute little kids and what I saw. I imagine their mom played with them like I did. They weren't shy pulling each others pj bottoms down at all -- it was all great fun. They had such cute bottoms! And of course, they shouted with glee whenever they could pull something down from me!

lol
still enjoy remembering...
Janie
A board for stories about girls pantsing and stripping others or getting pantsed and stripped

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by PhilMarlowe » Mon Mar 02, 2020 2:58 am

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Printed from https://www.writing.com/main/interactive-story/item_id/2184305-Babysitter-gets-babysat
Rated: 13+ · Interactive · Other · # 2184305
Created: March 3rd, 2019 at 11:30 am
Modified: May 31st, 2022 at 7:23 pm
A babysitting gig goes wrong! This is an interactive story containing 60 chapters . Each chapter tells part of the story and often ends with multiple choices. Make a choice and move to the next chapter in your story. When you reach a chapter that hasn't been written yet, don't be shy... make an addition!
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Please assume this story MAY contain graphic language, sexually explicit text, violence and/or any other displeasing topic you can or can't think up! To be certain you don't encounter textual content that may be offensive, you should leave this area and not continue on within this item .
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You're a 17 year old boy or a girl, who takes a week long babysitting job but the tables get turned and soon you end up being the one who's babysat. No sex scenes or killing any character.

Characters:

Kyle: The male babysitter
Jessica: The female babysitter
Amanda: Aged 11, the older of the kids you'll babysit. Thinks she's too old to be babysat and does her best to humiliate and make life difficult for her babysitters.
Josh: Aged 6, Amanda's younger brother. He still wets the bed which means there's a big stock of diapers, Pull Ups and Goodnites in the house.

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The sun had risen on another beautiful Saturday morning and Alex was slowly starting to get out of bed with memories of the previous day. Friday afternoon after school Alex was walking home from school with Natalie and they where talking about what people where saying about them and the rumors they where hearing about them and the other captains. The talk about them was flying everywhere like airplanes and bombs in a war zone and was spreading like wild fire. The latest was that Emily was so disgusted of how she got on the basketball team she quite the team and went to another school. Some say she went to a whole different state and others say she left the country but since no one could get a hold of her they couldn’t confirm it. The other captains stood their ground staying on their team and took all the heat of the student body talk. But talk about them didn’t last long as on Monday was the last day of school for them all and many where talking about skipping or just saying they want the weekend to be over with and how glade they be done with this school year. As Alex and Natalie came close to the spot where they part their ways Natalie quickly asked Alex something. Natalie: “hey umm Alex can I ask a favor of you?” Alex: “maybe?” *eyes her suspiciously* Natalie: “well I want to go out with some friends tomorrow night and my parents are going out with my aunt and uncle. So my aunt and uncle need a babysitter and the one they have is out sick so they need someone.” Alex: “and they want you to baby sit their kids?” Natalie: “exactly! But I don’t want to baby sit them. So I thought….” Alex: “that I baby sit them for you.” Nataile: “yes! Will you do it? Alex: “no!” Natalie: “wh… what? Come on pretty please? Alex: “find someone else to do it. You know that I watch anime Saturday nights and don‘t like to go out.” Natalie: “I know that but my parents said they only let you be my replacement. Besides the bra…. Huh angles are quite kids who just play video games in my room all night.” Alex: “………. I don’t know? What do I get out of it?” Natalie: “well my aunt and uncle will pay you 30$ a hour and they will be gone for about 4-5 hours.” Alex’s eyes lighted up immediately with dollar signs and said yes and after they parted ways Alex just had a bad feeling about doing it. ------------ Alex got out bed still unsure about taking this babysitter job and she walked over to her door and opened it up and walked down stairs and into the kitchen. Alex poured herself some cereal and milk and ate it quickly while watching Saturday morning Cartoons. Once done Alex went back up to her room and took off her light blue camisole and put on a lavender blouse. Alex removed her loose purple shorts and her white thigh high socks revealing her white panties with a small golden star on the front of it and quickly put on dark blue skirt with lavender knee high socks. She brushed her bed head hair and went on her day as normal. At 5:00PM Alex ate supper and cleaned up a bit and headed towards Natalie house. Alex had met Bryan and Sarah a few times when their parents where over at Natalie’s house but without the eyes of a parent around how would they act wondered Alex? That was a long time ago and by now Bryan had to be 12 and Sarah must be 11. Alex knocked on the front door of Natalie’s house at 5:30PM and Natalie answered who was dressed in a black t-shirt, denim shorts, white ankle socks and black clog shoes. Natalie: “hey Alex. They just arrived and I’m taking off. They already had supper and they are in my room playing video games and they know your babysitting them. Well see you later and good luck.” *giggles* Alex got a little freaked out from the giggling from Natalie but shrugged it off and entered the house and took off her brown clogs revealing her socked feet. She herd the noise coming from Natalie’s room and headed towards the t.v knowing they would be busy for a while. The time went by fast and it was already 7:30PM. Just 30 minutes more and Naruto will be on. Luckily last week she had tapped it and she was tapping it this week as well along with blue dragon, bleach, death note, and code geass just incase the kids wanted to play a game with her and Alex was right. About 7:45PM the kids came down and stared at Alex who was staring to nod off to sleep. Once Alex realized she was being watched she sat up and looked around and saw the kids looking at her. One of them was boy with dark blond hair with blue eyes with a light blue t-shirt with tan shorts and black flip flops on. The other one was a girl with blond golden curly hair with glass and green eyes and had on a pink sleeveless shirt with blue shorts and pink socks. Alex: “hey there. What can I do for you?” Bryan: “do you want to play a game?” Alex: “I don’t know? What kind of game is it?” Sarah: “just a game, do you want to play it?” Alex stared at them for few seconds knowing they where up to something and a mind of little kids where full of tricks and pranks to be played on people like her self but against her better judgment she took the bait. Alex: “sure I guess.” Both kids giggled and ran away out of sights and Alex just sat there confused. Alex just decided to sit there and wait for them to come back just so she wouldn’t fall for anything they got planned. It was 7:55PM when Alex herd a soft noise coming from down stairs and she immediately sat up a little spooked. She knew it was either the kids or someone else like a burglar. Alex ran over to the steps leading down to the basement and opened the closed door and listened for a sound and she herd something but wasn’t sure what. Alex flipped the light switch to the basement, but when she flipped the light switch the light did not come on. Now Alex was frighten but she was still determined to go down into the basement to find out what was going on. Alex went over to a drawer in the kitchen and pulled out a flash light and went back over to the steps and turned on the flash light and slowly made her way down the steps. When Alex was down in the basement she didn’t hear anything and she flashed the flashlight around to see nothing. Alex went into a room to her left which was a small family room with the only window in the basement and was opposite of where Alex was standing and she saw that it wasn’t broken and that the stuff sitting in front of it hadn’t been moved in a while. Confirming that a burglar hadn’t broken in Alex just decided that something gave out and fell over or a
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