Babysitter Challenge

Some girls just need a little kink in their lives and Amy is one of them. For the last couple of weeks she's been going to an online chat room and getting naughty challenges from online strangers. Most of them have been either really tame like going commando or else way too extreme like getting "Sperm Bank" tattooed across her face. But every once in a while she finds a good one and accepts the challenge.

This one is particularly good because she ended up talking to the person for like 3 hours getting to know her before the challenge was issued. By the time the stranger finally challenged her he or she really knew a lot about Amy and knew what a good challenge would be. it was more extreme than most of the ones she had done and there was a lot more risk of her getting caught but it was so perfectly tailor made for her that she couldn't turn it down.

19 year old Amy babysat for her neighbors, the Andersons, about once or twice a week for $20 an hour. It was a nice family with an 8 year old boy and a 5 year old girl. She'd been babysitting for them for about 4 years now so she was very comfortable with them and the kids love her. She's nervous about the challenge but she's committed to doing it. She doesn't want to chicken out after agreeing to do it.

The dare was fairly simple but devastatingly embarrassing if anyone were to ever find out about it. And she'd most certainly get fired for it and she really needed the money from babysitting.

The next time she babysat she would act normally while the kids were awake. But when she puts the kids to bed around 10PM things would change dramatically. She was supposed to steal a pair of the little girl's underwear. After that she was to go back out to the living room and strip completely naked and squeeze into the stolen panties. After that she was to neatly fold her clothes and put them by the front door. She'd spend the rest of the evening wearing nothing except the 5-year-old's underwear. Only when she hears the garage door open can she get re-dressed. She MUST get dressed in front of the door, no running into the bathroom for privacy. And finally she could not take the stolen panties home so she'd have to sneak them back into the girl's room.

Since she'd only have a few minutes between hearing the garage and them coming in the risk of getting caught was huge. And if the kids woke up they'd see her and they'd be sure to tell their parents if they saw that.

She was planning on a fun night so she decided to dress up just a little. She wore a pink thong and decided to forgo wearing a bra to save time when she got dressed. A nice pair of jeans and lavender top completed her outfit and then a little makeup and she was ready.

At first it was a perfectly normal evening of babysitting. Nothing out of the ordinary happened as she played with the kids and ordered pizza for them. Around 9 PM she sent the boy in to take a shower and get ready for bed and once he was out of the shower she ran a bath for the little girl. By 10 both kids were in their PJs and ready for bed.

She tucked the boy in and gave him a kiss on the forehead. The boy had recently developed a small crush on her and she knew he'd like it even though he said he didn't. Then she went to the girl's room where she'd picked out a book for Amy to read her to sleep. Amy tucked her in and read her to sleep before putting the book away and turning out the light to her room.

Only then did Amy's evening start to get interesting. With the lights off Amy went to the little girl's dresser and using her phone as a flashlight she found a pair of her My Little Pony underwear. The elastic looked very worn out on them so Amy thought they might fit a little better.

She crept out of the bedroom and back into the well-lit living room. She briefly considered turning on the TV so the kids wouldn't hear anything unusual but then she realized that she wouldn't be making much noise anyway and she'd rather hear them coming if either kid woke up.

Amy stripped down completely naked. And folded her clothes and put them in front of the front door on the floor with her thong right on top for quick access. That was the easy part. Now she had to do something that was more taboo than anything she'd even done as part of a challenge before. She stepped into the 5-year-old's panties and started sliding them up her legs. They started to get tight and she had to struggle with them about a quarter of the way up her thighs but after a little struggling and wiggling she managed to get them all the way up.

They didn't really cover anything though. The top half of her butt along with most of her cheeks were completely exposed and her neatly trimmed bush spilt out the top and sides of the front. It wasn't really comfortable but after a few minutes she got used to the pressure of the elastic digging into her skin.

After that though the next 2 hours went surprisingly normal; she tidied up a little from the kids' mess and eventually worked up the courage to watch some TV with the volume very low so she could still listen for the garage door. Neither child woke up and Amy was thinking that she'd gotten away with it and everything was going to be smooth sailing.

Then around midnight, she suddenly heard the garage door start to open. Amy immediately jumped off the couch and bolted for the front door to get her clothes. She slide the little girl panties down and kicked them off her foot where they slid across the smooth floor for a few feet. Then she grabbed her thing and yanked it all the way up in one smooth motion. The back of her thong got twisted on the way up but she had no time to stop and fix it now as she grabbed her jeans and started pulling them on. That's where things took a turn for the worse. She she tried pulling her jeans up she was still standing on the pant leg. While trying to correct that she ended up falling square on her butt. She gets up and finishes pulling on her jeans and buttons and zips them. she grabs her top and quickly slides it on. Amy glances at her shoes and socks but decides she probably won't have time for them but that she doesn't really need them either.

She still hasn't heard the garage door close so Amy thinks she still has some time as she looks around frantically for the little girl's panties. She spots them a few feet away and goes to grab them and take them back to the little girl's room. But she only manages a few steps before the front door opens and Mrs. Anderson mom walks in.

Amy stands there like a deer in the headlights in her hastily donned clothes and holding the little girl's underwear. At first she's too scared to say or do anything but after about 10 seconds of staring at each other Amy stammers something about finding the daughter's underwear on the floor and she was just going to throw them in the laundry.

Mrs. Anderson isn't fooled though. She knows a lie when she hears one. She tells Amy that her husband is dealing with something in the garage and that she better tell her what's going on right then and there or else Mr. Anderson would be in and he wouldn't be as inclined to listen.

All of Amy's self-control and resistance vanished with that and she broke down crying. She told Mrs. Anderson everything so fast and high pitched that Mrs. Anderson could barely understand her. But she got the jist of it and when Mr. Anderson walked in his wife told him she needed to talk to Amy alone. Mr. Anderson was concerned with finding his babysitter sobbing but trusted his wife and went ahead to their bedroom to give the girls some privacy.

Mrs. Anderson brought Amy onto the kitchen and made a pot of hot tea as she let Amy cry herself out. Once Amy finally calmed down a little bit Mrs. Anderson gave her the tea and asked her to tell her the whole story again. Amy started crying again as she told Mrs. Anderson the whole story again. This time Mrs. Anderson can understand her.

Amy knew that once she was done talking she'll be fired and that if Mrs. Anderson tells anyone she'll never be able to find another babysitting job. Babysitting is the only job she has time for with her busy class schedule so she really needed to make Mrs. Anderson sympathetic enough to keep it to herself.

Lucky for her Mrs. Anderson seemed very understanding. She even told Amy that she herself had done a few questionable acts in her younger day. Amy was starting to hope that she might get out of this easy when Mrs. Anderson told her that there would still be consequences for her actions.

She told Amy to stay in the kitchen and finish her tea while she decides what those consequences would be. Mrs. Anderson grabbed her daughter's underwear from the table where Amy had left them and walked out leaving Amy alone. Amy thought about trying to just run away then but knew that it wouldn't really help her situation and would actually probably hurt her.

A few minutes later Mrs. Anderson comes back into the kitchen holding an envelope which she handed to Amy. She told Amy that she'd written out Amy's consequences. She told Amy not to open it there but to wait until she got home. Amy was going to have a choice, either accept the consequences she'd given her, or never work as a babysitter again.

She told Amy that she wasn't being fired and in fact they'd need her to babysit again in a few days.

Amy thanked her profusely thinking that she'd gotten off a lot easier than she could have even hoped for. Then she walked home.

Amy went straight for her bedroom and opened the note to see just what these "consequences" would be. She expected something like half pay for the next month or something like that. Her heart sank as she read the note and realized that she was not actually getting off easily. In fact it was worse than she'd ever expected and she considered just walking away from the job and learning to live without any income.

Amy, you may continue to work for us as out babysitter but there will need to be some major changes for that to happen. For one thing you will be at my beck and call for the next month and babysit anytime we need you. If you had other plans you will cancel them and come babysit for us. You will not be paid at all this month. You will work for my husband and me for free.

As for wearing my daughter's underwear that is a completely different matter and a far more serious one. I understand your need to take on naughty taboo challenges, I was a bit kinky in my younger days as well, but that went way over the line. The fact that you would be willing to steal underwear from a 5 year old just to get some sort of sick sexual thrill shows a complete lack of maturity. Frankly I'm tempted to simply fire you for being so immature but I've decided to give you an opportunity to prove your maturity. But you'll have to earn it in my eyes.

Your underwear from now on will reflect that. From now on when you babysit I expect you to wear pull-ups. I suggest Disney Princess patterns because that's what my daughter wore and it might garner you some sympathy from me. And yes I will be checking to make sure you wear them. Once I think you've matured enough I will promote you to wearing little girl panties just like you did tonight. Eventually you may even earn your way back into big girl panties but don't expect that anytime soon.

I won't force this. You always have the option of quitting. But know that if you do I will make sure everyone in the neighborhood knows what you did and I guarantee you'll never find another babysitting job. If you keep working for me and I find out you've broken even the tiniest rule I set for you I will demote you to diapers and hire someone to babysit YOU along with my children. Your only option that allows you to keep your job is to obey every rule I set and do EXACTLY as I say. Tomorrow you will call me and tell me what your decision is.

Amy didn't get much sleep that night as she weighed the options in her head. She tries to look at it from every possible angle and eventually manages to convince herself that this all must be some sort of sick joke. No way would Mrs. Anderson actually make her wear pull-ups, would she?

She woke up bright and early the next morning and called Mrs. Anderson to ask her if she was serious. Mrs. Anderson told her that she was very serious.

Amy was terrified of what was about to happen but she knew she couldn't afford to lose the job. Even if she wasn't paid for the next month she'd still need the money when the month was up and she started getting paid again. She agreed to Mrs. Anderson's conditions.

After that all she had left to do was figure out what size pull up she would wear. She was in for a rough few months.