Babysitter Masturbation Stories

Babysitter Masturbation Stories

By Bethany Ramos | March 6, 2014

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Way back in the 90s, I was a professional teenage babysitter. I remember that I couldn’t wait until I turned 13 so that I could start making my own money.
In retrospect, 13 seems pretty young to babysit a whole gang of children. I vividly remember babysitting a child as young as two when I was a 13-year-old that couldn’t drive. While I’m sure that the toddler’s parents got a steal of a deal since I only charged $4 an hour, I don’t think I would ever put my kids in the care of a 13-year-old today.
But alas, my 13-year-old self babysat all the time. I loved babysitting. I couldn’t get enough of it. It was the only time that I felt like a grownup with a house to myself, without parents or siblings breathing down my neck. I remember I would beg to babysit with my friends because it felt like a special night out. If parents let me and my best friend Jennifer babysat together, we would only charge one hourly rate of $4, meaning that we both made $2 an hour just to hang out together. It was so worth it.
Teen babysitters mean well, but they’re still pretty naÃ¯ve. Here are some of the most RIDIC things I did as a teenage babysitter that make me cringe today:
1. Ate Everything I Could Find In The Cabinets.
When parents said, “Help yourself,” they meant it, right?
Macaroni and cheese and microwave dinners exclusively.
I am ashamed to admit that I did this, but I was CURIOUS. Can you blame me?
4. Watched Bad TV Shows In Front Of The Kids.
After watching an episode of Friends , one four-year-old girl said to me, “What is a bitch?” FAIL.
5. Counted The Hours Until The Kids Went To Bed.
The joy of my babysitting experience happened when the kids went to bed, and I was allowed to watch TV all by myself and control the remote.
I did fuck with thermostats a lot because I was never allowed to use the thermostat at my own house. Sweet, sweet freedom.
This is a complex story that is hard to explain, so don’t judge me, all right? The short version is that I was babysitting two hellions over the summer because they couldn’t be trusted to be left alone. I thought they were out riding bikes all day, and I was relieved. Turns out they were locked in a closet crying all day long, and I couldn’t hear them because I was watching TV so loud. Bad babysitter.
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We all love hearing about awkward situations, especially when they happen to someone else. Some are fairly innocent others were more disturbing.
Being a parent can carry its own awkward situations. If anyone remembers the show “kids say the darndest things” or has kids of their own, they will know what I’m talking about. Kids have this lovely trait that causes them to have no filter on the things they say, which can make for some awkward situations. They also have no sense of shame, so they aren’t above running out of their room, naked, while you have dinner guests over. But, we love it about them, it’s how we get a laugh out of this parenting gig.
When you become a parent you start saying things you never thought you would ever say. I have told my toddler more than once not to eat the furniture. And we take these awkward situations and turn them into funny jokes to share later. We all love hearing about awkward situations, especially when they happen to someone else.
It's a different story when you add a babysitter to the mix, who finds themselves in the center of some pretty awkward situations. From troubling kids, naked kids and even some really inappropriate parents, they’ve seen it all. The difference is they are getting paid for it, some not enough. One online reddit post asked babysitters to tell them their most awkward situations, and boy did they deliver.
Some were fairly innocent, while others were more disturbing. The next 15 posts are some of the most awkward situations babysitters have been in.
Babysitters not only have to deal with children when they take a job, but they also sometimes have to deal with the parents. Whether they are strict, weird or just downright out there. It’s a hidden line on a babysitter’s job description.
Our first babysitter’s awkward story is one that actually sounds quite terrifying. She stated that the mom and dad came home drunk, and fighting. The dad went outside to walk the dog, when the mom locked him out but the babysitter in. The mom kept saying “shh”, while the dad screamed from outside. The mom started saying, “He wants to kill himself instead of being with me.” The scared babysitter tried to reach for the lock to get out, when the mom pulled her hand back saying, “no, leave him for a while.” She waited for a bit and then bolted out the back door.
To make the situation even more weird, the babysitter stated that the couple had a pretty nasty break-up (duh) but ended up getting remarried to each other.
When you take a babysitting job, you also have to deal with bathroom situations. One babysitter was watching her boss’ daughter, who was four years old and happened to be constipated. The little girl went to the bathroom, but after she had been in the bathroom for 15 minutes, the babysitter went in to check on her and she was, of course, sitting on the toilet straining. The babysitter went to leave, but the little girl asked her to stop and squish her.
The confused babysitter asked what she meant, and the little girl responded by saying, “When I can’t poop, mommy and daddy always squish my tummy, so you have to squish me!” She then shows the babysitter how exactly to squish her. The babysitter does proceed to squish her and is able to help the little girl out. I hope she charged extra for squishing time.
Talk about an awkward situation, when a babysitter walks into a home and realizes that she knows the kids from somewhere. Turns out they were kids that had been featured on the show Nanny 911. If anyone is not familiar with the show, it portrayed families at their wits end. It usually involved parents who had out of control children and needed the help of a professional nanny to straighten the kids out.
Anyone would think this would be a great babysitting job, as the kids should be well behaved since the family had the assistance of a professional nanny. The babysitter was asked after her job if the kids were well-behaved since they had been on this show. The babysitters reply was “I liked the dog better, frankly.” I don’t think she will be babysitting for this family in the near future. She may be open to dog-sitting though.
When someone babysits for a family, they sometimes will get a ride home from of the parents. It is a nice thing for a parent to do after someone has just watched their children for them. One babysitter had a normal babysitting job, but an extremely awkward car ride home from dad. She babysat two brothers, aged 9 and 12, and after one job, the dad and two brothers were driving her home. During the car ride, the 12-year-old randomly said, “hey dad, don’t sleep with this babysitter.”
The dad’s reaction was to immediately stop the car and yelled at his son to apologize to the babysitter for making her feel uncomfortable. Later, the dad explained to the baby sitter that his son was making a reference to a movie he had seen. She stated that she was still not sure if she bought this excuse. I don’t think she will be babysitting for this family anytime soon.
One babysitter had the unfortunate luck to be hired to babysit for a toddler who was in the middle of potty training. Like most children, he was fine to go number 1 in the potty, but number 2 was another question. The babysitter could tell the little boy had to go to the bathroom, and kept asking him if he wanted to go to the potty. He repeatedly replied no. Then came the moment, the moment when the little boy could not hold it in anymore and started frantically running around the house holding on for dear life.
I should also mention that he did not have any pants or diapers on at this point, as the babysitter was trying to get him to the potty. The babysitter was desperately trying to corral him, but she was too late. He squatted in the middle of the kitchen floor and found relief. If you are babysitting a potty training little one, don’t fight it, just use the pull-ups!
One of the great things about kids is that they are not embarrassed easily. They have so much innocence about themselves and their body that they want nothing more than to run around in their birthday suit. When they are infants and toddlers it is the cutest thing to see them run around all free. It starts to get a little more awkward when the kids are older.
One high school student was a babysitter to an 8-year-old boy and his 5-year-old little sister. Every time she babysat them, as soon as their parents left the house, the sibling duo thought it was hilarious to get buck naked and jump on the couch, no matter how much she begged them to put some clothes on. She never was able to tell the parents, as she didn’t know who to bring it up, who would. Maybe the family is just free spirited!
Children are very smart and observant. They pick up on things so easy, and they love to mimic. They will mimic what people say and what they do. They are always watching, that is why a lot of parents, and babysitters, have to be extra careful in what they expose children too. No one could have seen this next one coming.
One babysitter found herself in probably one of the most awkward situations. She was babysitting for 3 little girls. One was 4 and then there were 2-year-old twins. They were all playing together when suddenly they all got naked, sat on the kitchen floor, and the twins started to “nurse” from the 4-year-old, who was pretending to be their mother. The older girl had obviously seen her mother breastfeed the infants, and I guess just wanted to help out. Still awkward for any babysitter, I wonder if she told the mother, and how that conversation went.
There are no words for our next poor babysitter. She explains that she had to babysit a child who had really bad eczema. The family had a pool in their backyard and after he would go swimming his skin would get really dry and scaly. It was also really itchy so he would scratch all the time. One day, after swimming, the babysitter was unable to find him. She finally found him way underneath his own bed, where she couldn’t reach him. She stated that he was just relaxing under there … eating his dry skin flakes.
That seems so creepy to me! He was just staring at her eating his own dry skin. I don’t know if this is a true story or something out of a horror movie. Maybe he was just hungry, or maybe it’s the birth of a strange addiction (have you seen that show?). I probably would have just laughed it off and informed the parents after. You can only do so much!
Another poop story. When one babysitter was 12, she used to baby sit for two little boys, aged 5 and 2. The 2-year-old was fully potty trained and independent in the washroom, or so the parents said. During the day, the little boy stated that he had to go to the bathroom. After ten minutes, the babysitter goes up to check on him and he says he’s not done yet. She leaves him to it, but then another 10 minutes go by, so she decides to jimmy the lock and get in.
What she finds is something you only see on TV, the little boy had squatted in the middle of the floor and relieved himself. After he was finished, he then proceeded to give the bathroom a new paint job. When he was done painting, he decided to run up to the babysitter and give her a big hug. Needless to say, she called the parents and asked them to come home.
Because kids can say the darndest things, at any moment, babysitters can find themselves in some pretty tricky situations. Parents themselves are always dreading the birds and the bees talk, so I can only imagine how awkward and uncomfortable it would be for a babysitter.
I am going to try my best to portray this next story in the most kid-friendly way possible. A babysitter was watching her teacher’s 8-year-old son. The boy went outside to play with a girl neighbour when suddenly he stopped playing and frantically ran over to the babysitter.
His “little friend” had gotten excited and he wanted to know what it was doing. The babysitter did not know what to say, so just told him to ask his mom later. It is a hard line for a babysitter to cross, so the best thing to do is divert it back to the parents, and then maybe go in the bathroom for a good laugh.
Sisters, I’ve found, can either be your best friend or your worst enemy. They can be someone you can confide in or someone who knows all your secrets. One babysitter has a sister who is 3 years younger than her, and during their teen years they would fight endlessly. The older sister was scheduled to babysit the best friend of her sister on a Friday. The day before, they had gotten in a fight and the younger sister had snapped her glasses in half. The girls’ mom had the idea to send them both to babysit as the older one could not see very well with no glasses.
The little sister had held a grudge and told her best friend to lock her older sister out of the house. The babysitter spent an hour threatening, pleading and banging on the doors. She eventually had to walk across the street to find a payphone to call her mom for help. The younger sister sounds like quite the trickster.
One babysitter was watching an 8-year-old boy, when all of a sudden he came out of his mom’s room in high heels, his mother’s best dress and his best attempt of smeared lipstick and mascara. He then calmly asked the babysitter if she thought he was beautiful. We live in a great, modern world that accepts people no matter how they classify their gender, but it is an extremely awkward situation for a babysitter to handle.
Again, it sounds like a creepy situation you would only expect from Norman Bates. But, you got to go with the flow and accept whatever happens. I say, strap on your own outfit and enjoy the impromptu game of dress-up. I do hope she told the boy that he was beautiful though. This babysitter obviously has no luck, at a different job, she states that she was paid in bananas. I think she either needs a new job, or start looking in a different neighbourhood.
We still seem to have gender stereotypes where we think that girls are easier to care for than boys. I have a one year old girl, and I can say it is not always true. She is a handful. But, I do still feel for this next babysitter who was asked to babysit three brothers one summer.
Their ages were 8, 4 and 2. As brothers do, the older two had gotten into a fight. As the babysitter was trying to break up the fight, she didn’t notice that the 2-year-old had walked into the room with a large butcher knife. The babysitter states that she has no idea how the toddler got a knife out of a drawer with a safety lock. Can you imagine seeing a toddler coming towards you with a butcher knife! Again, sounds like something out of a horror movie. The best you can do in that situation is to remain calm and hope you can get the knife away from him without a trip to the ER.
Sometimes pets come with a babysitting job. One babysitter was watching such a family of three kids who had recently gotten a pet hamster. They all wanted her to bring out the hamster so they could all play with it. When she went into get it, she was horrified to find that the hamster was dead. She did some quick thinking and told the kids that the hamster was sleeping and she put it in their parent’s room so they wouldn’t find it for the rest of the night. I am impressed with her quick thinking at handling the situation. I may have panicked and taken them to the pet store to buy another one.
It sounds like the babysitter did the parents a favour. When the parents got home, the babysitter told them what had happened, and the father quickly responded, “oh, thank god, it was impossible to handle that thing without it biting someone.”
Some kids are just more work than others. One babysitter was watching 4 kids; ages 12, 10, 6, and 3. Things seem to be going pretty well, the eldest was playing his play station and the 10-year-old was in her room playing Barbies. With everything seemingly sorted out, the babysitter decided to play hide and seek with the younger two. The babysitter was hiding in the closet, when she started to smell smoke. She ran into the kitchen, where smoke was pouring out of the microwave.
At some point, the 10-year-old had decided to put all her underwear in the microwave and cook it for 10 minutes. While the babysitter was in the middle of removing the underwear with a pair of tongs, the mother walks in. The babysitter grabbed her pay and ran out of the house. She never did get an explanation on why the 10-year-old decided to put her underwear in the microwave.
Ashley is a Stay-At-Home mom to three beautiful children. She loves to write, read and dive into a Pinterest craft (or two).

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