Playing With Herself While Babysitting

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Playing With Herself While Babysitting
What was the most inappropriate thing you have been asked to do or have done while babysitting?
Babysitter, nanny, and part-time kid wrangler · Author has 3.3K answers and 24.9M answer views · Updated 5 y ·
Originally Answered: What is the most inappropriate thing you have been asked to do or have done while babysitting?
Have you ever had sex with a minor as a babysitter?
What is the naughtiest thing you have ever done with an adult while you were still technically too young to be doing it?
I had sex with a boy while babysitting. How should I tell the parents?
Have any girls masturbated while babysitting?
What's been your most inappropriate experience as a baby sitter?
USMC [ret] pro gun, good guy. · Author has 503 answers and 3.1M answer views · 5 y ·
Have you ever had sex with a minor as a babysitter?
What is the naughtiest thing you have ever done with an adult while you were still technically too young to be doing it?
I had sex with a boy while babysitting. How should I tell the parents?
Have any girls masturbated while babysitting?
What's been your most inappropriate experience as a baby sitter?
Do you have photos of your babysitter naked?
What's the most inappropriate thing an adult has done to you as a teenage girl?
Being a teenage babysitter have you ever had sex with the father of your children you were taking care of as payment?
As a kid, did you ever have sex with your babysitter?
How did you convince your babysitter to have sex?
I'm 16 and I want to have sex with my babysitter. How can I do it?
What are the dirty little secrets of babysitting?
Did you have sex with your babysitter at 15?
Have you ever had sex with the babysitter?
Have you ever had sex with a minor as a babysitter?
What is the naughtiest thing you have ever done with an adult while you were still technically too young to be doing it?
I had sex with a boy while babysitting. How should I tell the parents?
Have any girls masturbated while babysitting?
What's been your most inappropriate experience as a baby sitter?
Do you have photos of your babysitter naked?
What's the most inappropriate thing an adult has done to you as a teenage girl?
Being a teenage babysitter have you ever had sex with the father of your children you were taking care of as payment?
As a kid, did you ever have sex with your babysitter?
How did you convince your babysitter to have sex?
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It was one of my regular jobs to watch 2 year old Bailey* and her brother while her parents had date nights. One night, her father told me this as he and his wife left for a sports watching party:
“Ok, so I may call you later, depending on how the team is doing. If we're doing badly, you need to put Bailey in front of the TV because she's our good luck charm. She doesn't have to watch the game or anything, but just keep her in the room for me.”
I probably looked about as skeptical as I felt, because he felt the need to add:
“I'm not, like, superstitious or anything. It's just that we always win w
It was one of my regular jobs to watch 2 year old Bailey* and her brother while her parents had date nights. One night, her father told me this as he and his wife left for a sports watching party:
“Ok, so I may call you later, depending on how the team is doing. If we're doing badly, you need to put Bailey in front of the TV because she's our good luck charm. She doesn't have to watch the game or anything, but just keep her in the room for me.”
I probably looked about as skeptical as I felt, because he felt the need to add:
“I'm not, like, superstitious or anything. It's just that we always win when Bailey is in the room, and I don't want to jinx it.”
I must have agreed, because an hour later he called me and I did indeed bring the toddler to the TV room. I muted the game while the child and I played with blocks.
When he got home, the father questioned if I had done as instructed, and I said I had.
I was never invited back to babysit. Maybe my mojo cancelled our Bailey’s lucky mojo, or something.
Marry their mother. That request from three little girls will scare the hell out of a single man. Oh, wow, will it ever.
My next door neighbor was a single mother with three daughters aged 11, 13 and 14. Really cute, really sweet little girls. Their mother got home from work much later that I did. After school the girls would come to my house and wait for me to get home, perhaps an hour later. My house was a “safe haven.”
They knew where the door keys were located. I told them to only use the back door and to try not to let anyone see them going in. I wanted them safe and secure until I
Marry their mother. That request from three little girls will scare the hell out of a single man. Oh, wow, will it ever.
My next door neighbor was a single mother with three daughters aged 11, 13 and 14. Really cute, really sweet little girls. Their mother got home from work much later that I did. After school the girls would come to my house and wait for me to get home, perhaps an hour later. My house was a “safe haven.”
They knew where the door keys were located. I told them to only use the back door and to try not to let anyone see them going in. I wanted them safe and secure until I got home. “Keep the doors locked and only open them for your mom, me, or [ ], my girlfriend.” That wasn’t the best of neighborhoods.
I would often cook dinner and feed them, of course their mother after she got home and my girlfriend. Those girls were very innocent, guileless. They made it very obvious that they preferred evenings where it was their mother, them and me. No girlfriend.
One evening, when they knew my girlfriend wasn’t coming over they had decided to make a romantic dinner for me, their mother and them. Conniving little wanna-be match makers. Spaghetti and a bottle of wine! Romantic!
When I got home all three were sitting at the kitchen bar with the stovetop in it throwing spaghetti at the refrigerator across the kitchen. They had heard that when spaghetti was done if you threw it against a wall it would stick. They were sticking spaghetti to my fridge from across the room.
They had planned ahead and opened a romantic bottle of white wine to go with the pasta for mom and me. The wine was half gone. They were half gone, too. They wanted a heart to heart talk. “When are you going to marry mom?” On and on until mom finally got home. Then they clammed up. Mom didn’t know they were going to do this. I opened a bottle of red wine for mom and me. I needed it.
Dinner was good. They had cooked about two pounds of dry spaghetti so even with what they had stuck to the fridge there was more than enough to eat.
To draw this story to a close their mom and I didn’t marry. She married an exceptional man who legally adopted the girls. I was at the wedding. The girls were so happy they cried. I got something in my eye.
My girlfriend and I didn’t marry either.
If this has happened today the first night when I got home with those teen and preteen girls in my house is the night I would have gone to jail. It’s sad that because of the actions of some, some humans cannot be human. There has GOT to be a very special Hell for those who prey on the innocents ruining things for the rest of humanity.

Babysitters have to deal with a lot: high energy kids, cleaning up after the kids and more. Here are some of the most inappropriate things they have to deal with.
“I once babysat just one night for these strange parents. The children were two five year olds, one was adopted. The parents told me that their biological son, X, was allowed to play Grand Theft Auto in his bedroom for as long as he wanted and that they had a stash of candy for just him and there were no restrictions. Yes, he was a brat. But then the parents told me about Y, who they adopted a few months prior. They actually told me ‘he’s not allowed to leave the living room, because he’s adopted.’ And that was their only reasoning. It was shocking and to this day I can’t fathom or understand those people’s reasoning. Also, I can’t imagine what else he was denied or how else his treatment was altered just because he was adopted.” Source
“We’d just moved to a new town in rural Ireland and I got part time work experience in a local school. John, only 11, one day asked me on behalf of his mum if I did babysitting. I said usually no but if she needed help I’d help out. So eventually I met her and she asked me a specific day. I said yes. So I get there and the mother is just on her way out the door. ‘Ok the younger ones are in bed, it’s just John and Sarah you have to look after. And if John asks, could you make a run to the shop to get him some tobacco and vodka. There’s some lemonade he can mix it with don’t worry.’ It turns out little John was an alcoholic. At 11. Twice later that year teachers caught him with beer in his bag and even had to call the police when he gave an 8 year old a sip of Guinness. Turns out John’s parents used to use vodka and even whiskey to shut him up when he was loud (it’s later been discovered he had ADHD).” Source
“When I was 11 my sister and I were frequently watched by the same sitter. A 17 year old girl. I thought she was hot. Like many 11 year old boys I was subject to frequent unwanted erections. One Saturday night my sister was asleep and I was watching Are You Afraid of the Dark with our sitter. Thats when it happened. BOING an erection showed up. I was embarrassed and unsure what to do, I started to squirm a little and try to formulate a plan. I was too late, my sitter glanced over and saw the erection. What she did next blew my 11 year old mind. She started to stroke it over the fabric. Then she reached in and pulled it out. She proceeded to give me what was my first, and by far my most memorable hand job. All the way to the happy ending. I was hyped. I was stoked. I was a legend in my own mind. She only watched us once or twice after that and there was no repeat of the event. It took me close to twenty years to realize that what she did was COMPLETELY F–KED UP. The boost to my ego, and the way it affected my opinion of sex and women was not great. I came to expect sexual satisfaction, I became the type to ‘whip it out’ at my first chance alone with any female and see what happened. All in all, I think it warped my perception of women, sex and relationships very much and was a contributing factor to many years of having very little relation in my mind between sexual activity and emotional connection.” Source
“I came home from work one Friday to find my wife babysitting a neighbor’s child, probably 18 months. I was told they were out for the evening and would be coming back late, probably picking him up Saturday morning. By Monday, I wasn’t sure if I should call COPS or just start raising him. From the moment I got home Friday, I took care of him, played with him, fed him, changed him. I’d heard him crying every day from their apartment; he’d be left to cry himself to sleep at night. When I put him to bed the first night, he started crying as soon as the light was off. We’d put his playpen next to our bed for him to sleep in, so I laid down on the bed and put my hand on his back and talked to him quietly. After a few minutes, he fell fast asleep. Saturday, Sunday, and Monday night, all I had to do was lay him down, put my hand on his back, and say ‘See you in the morning.’ I did not have to stay in the room, he’d fall asleep with no crying or fuss. He just wanted to know that he wasn’t being abandoned. They came back Tuesday. We’d been knocking on their door and calling every day. They acted as if nothing were wrong, and only paid my wife for one day. After they finally showed up and got him, I could hear him crying in their apartment again. It seemed to anger his mother when I told her how I got him to sleep quietly every night. Shortly after, they moved.” Source
“The family had two boys, about 2 and 8. The older boy was very mischievous, and didn’t like to go to bed when he was told. The younger one would follow his brother around, so it was a pain getting them both to sleep. The parents told me to deal with this by locking them both into their rooms, and to ignore them if they cried. I felt really uncomfortable locking them in, knowing that if there was a fire or any emergency I might not be able to reach them in time and they would be trapped. I also felt that it was cruel to ignore a crying toddler in my care. I instead played with them until they were really tired, put them to sleep, and sometimes sat right outside their doors to make sure they stayed in bed.” Source
“When I was 17 years old I babysat for a couple that lived about 15 minutes from our house. Dad was invariably the one who drove me home. One evening he started stating what he considered facts: ‘You’re tired of all those 17 year old boys. You’re ready for a real man.’ I answered awkwardly, slowly understanding where he was going with this. The drive ended and I hurried out of the car. The next time they asked me to babysit, I thought about it, and thought maybe I was just overreacting and went back. That night he and his wife were accompanied by his younger brother. Dad and younger brother drove me home. They lit a joint and handed it to me. I partook while they began to dream up schemes to hang out with me outside of the babysitting gig. I never went back after that. In hindsight, I can understand why the mom was always so frustrated that their sitters would never stick around.” Source
“It was the early 70s and I was babysitting occasionally. Jobs were posted on a dorm bulletin board. I arrived at an apartment full of stoned people, including the parents, getting high for a concert. The kids were asleep already. They offered me a hit. At first I was gobsmacked that they wanted me to watch their kids while high. And then I thought they probably smoke around them all the time. Then one of them said, ‘So, you goin’ to the concert?’ ‘No. I’m babysitting.’ ‘Oh, right, man.'” Source
“I did a bit of baby sitting and had asked to look after a baby, so I rode my bike about 15km to get to their place. The kid was a lot younger than I had been used to looking after. The mom left and didn’t really say when she was back, so I fell asleep on the couch, woke up a few times and checked on the baby. It was the 80s so no mobile phones and I just sort of assumed this is what I was supposed to do. She turned up about 8am the next morning, thanked me for the babysitting and I sort of waited awkwardly till I realized I wasn’t getting paid, so rode back home. In retrospect, that is some next level irresponsibility, even by 80s standards. I also still don’t get how she thought that it wouldn’t be paid.” Source
“When I was 11, I babysat for a couple that lived 8 blocks from my house. They had one child and both parents were doctors. They were nice people and I baby sat for them almost every Saturday night. When they got home, they would pay me to the quarter hour. No rounding up for good measure. The worst part? The husband would ask me if I could walk home by myself. He was always tired and not in any condition to walk or drive. What was I supposed to say? No? So I would bolt home, scared s**tless. If my parents were home, I would call my dad to come get me. Sometimes he was sleeping and he had to get out of bed. The docs would make me wait out front for him, too. They needed their sleep. This made my parents furious but this went on for about 6 months. Finally, my mom had enough. The next time the Drs. called me to babysit she scolded them saying, ‘Listen, my daughter is no longer going to babysit for you if you will not drive or walk her home at the end of the night. My husband and I don’t think it is our responsibility to pick her up. We raised 3 daughters and had plenty of sitters over the years. We always gave them rides home or put them in a cab. Always. You need to step up and take this responsibility.’ I was floored. My mom was full of calm, but righteous indignation. It was beautiful to witness. ‘And for the record, I know this is your first child so you may not know these things, but it’s customary to round up when calculating the pay. The quarter hour payment is ridiculous. Especially because you’re not driving her home. Surely you can spare a few quarters for your son.’ Mrs. Doc apologized profusely and thanked my mother for letting her know. I continued to baby sit for them until HS. Then I got a life.” Source
“I would babysit for a friend of my parents when I was between 12-15 years old. The parents were pretty big partiers, but I actually liked the fact that they stayed out late because I was paid by the hour. They would come home pretty drunk and eventually the father started asking me to drive myself home. He would sit in the passenger seat while I drove and drive himself back to his place after dropping me off. I’m sure he thought this was a safer alternative to him driving me home while completely drunk, but not only was I under age, but not a particularly good driver. Unfortunately, years later his wife did kill herself in a single car accident involving alcohol.” Source
“I used to babysit for a couple who I’ll call John and Jane. One of the things I noticed early on was that they were having marital problems, which I concluded from marriage counseling papers left on the countertops. It looked like mostly some kind of worksheets where they wrote down everything they didn’t like about their spouse. Their son could read and obviously so could I. I tried to ignore it, but I’d be in the kitchen making their son a sandwich next to a piece of paper that said ‘John does not care about my sexual satisfaction’ and things like that. So the situation was awkward enough, but then it got weirder. John always got home from work before Jane, and he would usually just drive me home immediately. One day John arrived home as usual, and asked me to come talk to him for a minute. I figured I’d done something wrong so I was freaking out. What he did say was ‘Would you mind taking (son) out to play in the yard for a few minute before I take you home? I want to jump on the computer and whack one out before Jane gets home.’ Me being 11 and immensely relived he didn’t yell at me for anything, I just said ‘Sure.’ Some time later John drove me home. It was one of the most awkward car rides I ever had in my life.” Source
“When I was only about 11 I was asked to babysit twin 6 year old boys, both who were in special classes for behavioral problems. Since I frequently babysat my brothers, I apparently thought I was capable of doing this. I was wrong. The most standout memory of this was: Twin 1: Look, I can climb out my bedroom window to the roof. Me: OK cool, but please DON’T do that. Twin 1 starts to open window. Twin 2: Can I go to the bathroom? Me, while wrestling twin 1 away from window: Yeah, of course. Twin 2, waving from outside the window, on the roof of their two story house: Look, we can go out the bathroom window too! Twin 1: Yeah we do this all the time with our mom Me: And she doesn’t think its dangerous?? Twin 1: No she does, sometimes she just ties us to our chairs so we don’t do this. I guess the inappropriate part is thinking a sixth grader could watch your kids when they had such severe behavioral problems.” Source
“When I was 15 we lived next to 3 divorced women who each had a child around 3 yrs old. I babysat for them a lot as they liked to go out partying A LOT. They told me if the kids wouldn’t go to bed to just put some cream de cacao in their bottles. One time I called one of the ladies and told her I was going to do LSD for the first time and didn’t want to do it at home. She said I can probably figure out somewhere to go. Upon leaving the house with me and her child knowing full well what my plans f
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