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Babysitting Perks

Babysitting Perks

Update: 2025-12-30
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Babysitting Perks



A Snowstorm leaves the sitter stuck at her client's house.



Based on a post by lily ann.
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I spent most nights of my senior year in high school
babysitting. It was my parent's fault, really. Apparently having a real job
would affect my grades too much, so I was stuck earning my money by spending my
nights in various houses, feeding Kraft Dinner and hot dogs to hyper-active
kids while their parents took a night off.



It wasn't terrible, by any means. In fact, I took it quite
seriously. I don't mind children, and at most places I had full access to the
fridge while I finished off my homework after putting the kids to bed. The pay
wasn't bad, either. I liked to play games with the kids and most of the time,
the kids asked for me back before their parents did. I had a pretty steady
clientele, most within walking distance of my house. It was convenient for me;
I had procrastinated getting my driver's license so long that I was 18 and
still only had my learner's license.



It was late February when Mr. Riley called the first time. I
gave my cell phone number out to my clients, and he was lucky enough to call me
on one of my nights off. I was in the bathtub when I answered.



"Hello?"



"My name is George Riley. I'm looking for Anna
Marchand," replied the person on the other end. I immediately liked his
voice. It wasn't too deep, but it was soft and smooth. I was almost tempted to
consider it calming, but he sounded slightly stressed.



"You've reached her," I said.



"Oh; hi, Anna.  I'm a friend of the Anderson's, and
they recommended you as a babysitter. I've got a few late meetings next Friday,
and my regular sitter isn't available. I was wondering if you'd be available to
watch my son."



I shifted in the tub, hoping he didn't hear the water
splash. "I usually take Friday nights off, but it sounds like you could
use the help."



"I really could," he said. "I'm afraid I
can't offer you more than your regular rate or anything;”



"It's fine," I interrupted. "I don't mind,
sir, really. I'd love to babysit for your son."



"Thank you so much," he said, sounding thoroughly
relieved. "His name is Kyle, and he's three. I would need you from around
five until pretty late."



"Not a problem," I said. I got the rest of the
details from him, and made a note of his address. He lived on the other side of
town, but I was sure my mom would be okay with driving me.



Friday came along and I went home after school. I had worn a
cute skirt to school and debated on wearing it to the Riley's, but decided against
it;  three year olds could be really active and I didn't want to deal with the
skirt. Instead I put on my favorite pair of jeans, dark blue and fitting
snugly, with a tight blue scoop neck t-shirt. I never tried to dress
provocatively when I went to babysit, but I did try to look fairly nice. I
rarely got to go out with friends or boys, because I always seemed to be taking
care of someone else's kids. Usually I was alright with it; not dating just
meant I didn't have to deal with all the drama my friends did, and there were
very few guys I knew that I was really interested in, anyway.



I knew there was a reason for it. I would never tell any of
my friends, but I found a lot of the men I babysat for much more appealing than
any guy my age. I babysat for a lot of babies and toddlers, so their parents
tended to be either late twenties or early thirties; not that much older than
me, at any rate. A lot of the men were good-looking, and more than once I found
my mind fixed on one of them while I got off before falling asleep.



I didn't know about Mr. Riley, though. The Anderson's were a
couple in their early forties, and since they had referenced me, I figured Mr.
Riley might be a bit older than the usual men I babysat for. Even still, I put
a little bit of effort into my outfit. The t-shirt clung nicely to my tits,
which were a nice size; 36 C, and fairly firm. I had a push-up bra underneath,
which showed just a hint of cleavage. It fit slightly looser around my stomach.
While I would never consider myself fat, I didn't have the hard, flat tummies
that all my friends seemed to work towards. I didn't mind, though. It was a
small price to pay for having great hips and a round ass. I knew that if I
tried to lose any weight, I'd lose those curves, and that was not something I
was willing to give up to have a flat stomach. After putting on just a bit of
makeup and brushing my long hair off my face, I grabbed my backpack and went to
ask my mom to drive me over.



My mom dropped me off at quarter to five. I walked up the
driveway. The house was in a fairly good neighborhood and looked pretty nice. I
rang the doorbell and waited patiently.



The door was opened a few moments later by a man who, I was
surprised to see, looked to be in his early thirties. He was good looking,
about 6'2'' and fairly toned, with deep brown eyes and dark brown hair. He was
wearing a nice suit, but looking slightly frazzled.



"Mr. Riley?" I asked.



"Yeah, you must be Anna?"



I smiled. "Nice to meet you, sir."



He smiled and opened the door. I turned around and waved at
my mom, who had been waiting to make sure we had the right address. Mr. Riley
led me into the house and offered to take my jacket. I smiled and gave it to
him, looking around the house as he put it away. It was nice, but a little
messy. There were toys everywhere and I could hear a TV playing a kid's show in
the next room.



"Sorry about the mess," Mr. Riley said, returning
without my jacket. "I haven't had time to clean anything up."



"It's fine," I said, smiling.



"No, it's embarrassing." He smiled at me
apologetically. I grinned. He was very attractive, especially when he smiled. I
was glad I had put a bit of effort into my outfit, and briefly let myself
wonder what he was like in bed.



My thoughts were interrupted by a little boy rushing into
the front hall. Mr. Riley turned and lifted the boy.



"This is Kyle," he said. Kyle looked at me shyly,
but he was smiling. He was absolutely adorable, with big brown eyes just like
his father's, and lighter brown hair that fell in his face. He had a smudge of
dirt across his cheek and his father wiped it off tenderly.



"Hi Kyle," I said. "I'm Anna. I'm going to be
here with you tonight."



"Say hi, Kyle," Mr. Riley said, nudging the little
boy.



"Hi," Kyle said quietly.



Mr. Riley put him down and Kyle ran back into the other
room.



"I've got to finish getting ready for my
meetings," he said. "If you wouldn't mind watching Kyle?"



"Of course," I replied, "that's what I'm here
for." I walked into the other room and sat on the couch. Kyle looked up
from the floor, where he was playing with some cars. I smiled at him, and he
stood up, picking his toys up and walking over to the couch.



"Wanna play?" he asked softly.



By the time Mr. Riley poked his head in to tell me he was
leaving, Kyle and I were playing cars. Kyle hardly noticed his father leaving,
making my job easier. Kids always hate it when their parents go.



He was a good kid, and very talkative. We played cars until
I decided it was time for him to eat. Over dinner, Kyle told me about his mom.
I wasn't exceptionally surprised to find out that his parents were divorced,
but I was shocked to find out how much Kyle knew about it; especially how
easily he told me about how his mother just walked out. It's surprising how
much information kids can absorb, and I felt so bad for the poor kid that I
gave him an extra scoop of ice cream for dessert.



It was probably a bad decision on my part; the extra sugar
hyped him up so much that I had trouble getting him to bed. By the time he
finally fell asleep, it was an hour and a half past his bedtime, and I was
exhausted from chasing him around. I felt bad for disobeying what Mr. Riley had
asked, but figured I could explain it when he got home.



After Kyle was asleep, I tidied up the den and kitchen
before settling myself on the couch. I turned the TV on and started studying.
It didn't take me long to finish my homework, so I spent some time channel
surfing and reading some magazines that Mr. Riley had on the coffee table,
checking on Kyle every once in a while. I was so tired that I must have fallen
asleep at some point, because I was startled awake when I heard the front door
open.



I sat up and a magazine fell off my lap just as Mr. Riley
entered the room. He smiled at me. "Did I wake you up?" he asked.



I yawned. "I guess so," I answered, laughing.
"I didn't even realize I had fallen asleep."



He laughed and entered the room, bending down to pick up the
magazine I dropped. "Did Kyle wear you out?"



I smiled at him. "Well, it's my fault, really." I
blushed. "I felt kind of bad for him, so I gave him a little extra ice
cream after dinner. He went to bed a little later than you said. I'm
sorry."



"Oh, that's fine," Mr. Riley said. "It's rare
that he likes babysitters, so a little extra ice cream might have been
okay." He frowned for a moment. "Why did you feel bad for him?"



I bit my lip nervously. "Well, he just started talking
about; about his mom; and I just;”



Mr. Riley smiled, holding a hand up to

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