The Babysitter - Cover

The Babysitter

Copyright© 2012 by jenny rosario

Chapter 1

Coming of Age Sex Story: Chapter 1 - An older teen with fashion sense counsels a younger teen on how to dress and look her best. An awakening story.

Caution: This Coming of Age Sex Story contains strong sexual content, including ft/ft   Reluctant   Lesbian   First   Babysitter   Transformation  

Amanda took one last look in the mirror. At seventeen, Amanda had a definite look. She wore her raven-colored hair shoulder length and straight usually parted nearly down the middle. Her hair complemented some would say her rather striking hazel eyes. Color came easily to her cheeks, so often she had a healthy pink glow even without any makeup. She did like to dress up and would often highlight her eyes and lips. She was average height and a little skinny. She stepped back to check out her profile and was pleased to see how much her breasts stood out even in this conservative top. It wasn't like she had a huge bust, 34Bs, but on her frame she thought she looked good!

She decided she would wear a little bit of makeup but otherwise she would keep on the just above-the-knee skirt and matching top with her pantyhose. After all she was just going to be babysitting some little brat and she didn't need to impress anyone. Her mom's friend had called up at the last minute desperate for someone to look after her daughter Sandy. Apparently the mother was starting some night class and her usual babysitter had been confused over the dates. If things went well tonight Amanda might have a regular job, two nights a week and an odd weekend, looking after this Sandy girl. Amanda didn't really like babysitting little kids, but the mother was willing to pay very well. That was another good thing; though it was just the mother and daughter, they were very well off. Amanda thought that that couldn't be a bad thing. Unless the little girl was really spoiled.

All these thoughts were going through Amanda's mind as she finished her makeup and prepared to leave.

"You call me if any problems arise," called out Amanda's mother. They lived just a couple blocks apart--another positive, thought Amanda.

"Ok, Mom, I should be home around ten," Amanda said as she breezed out the door.

When she got to the house, her first surprise appeared at the door. Sandy was not some little kid but a teenager or at least she looked like one. She was shorter than Amanda by a good four inches, an average weight though, not skinny or heavy. Like her name she had sandy-colored hair that was a little longer than Amanda's, kind of wavy, which she parted down the middle. Amanda noticed her blue eyes and full red lips. But what drew her attention most was this girl's body. Though she looked young (was she still in grade school, wondered Amanda), she definitely had a mature figure. She had curves that showed even under the jeans and sweatshirt she was wearing as she stood at the door.

"Hi, I'm the babysitter, my name's Amanda."

"Oh, hi, I'm Sandy," she said shyly. Then she called out, "Mom, Amanda's here!"

Sandy's mother strode up to the door. "Good, hello, do come in," she said in one breath. "I'm running late so I'll let Sandy give you the house tour. I'm so glad you could come on such short notice. I hope this works out. My class is over at 9:30, so I should be back by ten easily. The emergency numbers are on the fridge. Help yourself to any food. Sandy will show you. Any questions?"

"Bedtime?" Amanda asked, then she immediately wished she hadn't when she caught Sandy's eye.

"Oh, I think Sandy's old enough to still be up when I get home. I wanted you to be here--I just didn't think she was quite old enough to be alone in the evenings. After all she is only thirteen. You do have homework, don't you, dear?"

"Yeah, I have some, but not a lot tonight," Sandy replied. She was looking with great interest at Amanda.

"Ok, I've got to run. Have a nice night."

After the mother left there was an awkward silence until they heard the car drive off.

"Shall I show you around?" Sandy asked somewhat timidly.

"Sure. What grade are you in?" asked Amanda.

"Seventh."

Sandy gave her the full tour. Amanda noted the swimming pool in the back yard and the fully stocked kitchen. She liked the spaciousness of the downstairs. There was a family room with a huge entertainment center.

Then Sandy took her upstairs. Sandy's mom's room was large with double walk in closets. One of them was open and Amanda saw that it was packed.

"Wow, your mom has lots of clothes."

"That's not all of them either!" Sandy exclaimed. She opened the other closet. "Mom's crazy over clothes and shoes." Amanda's eyes opened wide. "And you should see her makeup! In here," Sandy called. It was a bathroom off of the master bedroom.

"You get your own bathroom?" Amanda asked.

"Yep," Sandy responded happy to impress this older girl.

"Let's see your room," Amanda said.

Sandy had a room almost as big as her mom's with clothes spilling out of closet and dressers. "I need to clean my room," was all Sandy said.

Amanda wanted to see the kinds of clothes Sandy had. "You sure do," she said. Amanda was very careful with her own clothes. "Why don't you do some now? I'll keep you company."

"Ok," Sandy said surprisingly cheerfully.

Meanwhile, as they talked about school and boys and music as Sandy picked up a dress here, some jeans there, Amanda was thinking. This could be kind of fun. Sandy had all these clothes and probably could buy whatever she wanted. She had what Amanda was guessing was a very curvy body for a thirteen-year-old. It would be fun to dress her in the latest styles and she what she would look like. Maybe get her to wear a little makeup. Maybe even get her to buy some more grownup things. She could be Amanda's Barbie doll! A living doll for her to dress up.

Things were turning out better than what she'd thought just an hour ago.

"Show me some of your favorite clothes," Amanda said. Sandy was only too happy to have her babysitter's attention. She didn't get too much attention from her mom, her being so busy with work and now the evening classes. Sometimes she was home alone after school every day of the week.

She pulled out some tops and jeans, a couple of skirts and one dress, none of which impressed Amanda all that much.

"Put on that blue skirt for me," Amanda said, "I want to see how it looks on you." It was pleated and Amanda thought it might hang nicely over Sandy's hips. Instead it was too long for Amanda's taste and ended up looking kind of old-fashioned. She wrinkled her nose. Sandy noticed.

"I have this other one," Sandy said pointing to a pink skirt that looked like it would at least fall above the knees.

"Ok, let's see that one."

It was better as it was more form fitting and came to about an inch above her knees.

"Sandy, what if I gave you some tips on what clothes to buy?" Amanda pushed forward. "On Thursday, we could head out to the mall and look at some things. You'd have to get your homework done before I got here."

"That would be super!" Sandy said. She was somewhat in awe of this high school girl.

"Do you have any money to buy clothes?" Amanda asked.

"Oh, yeah, my mom gives me whatever I need. In fact she's been after me lately to get some new things."

"Good. When I come for a weekend to babysit, we'll really have some time to work on your wardrobe. Until then I will ask you to get some things on your own. Now, let's see your undies."

"What?!" Sandy exclaimed.

Laughing, Amanda said, "No, not what you're wearing, silly. Your undies drawer. What a girl wears underneath is just as important, maybe more so, than what she wears for every one to see."

"Oh, ok," Sandy was relieved and moved to her chest of drawers. All kinds of things were still spilling out.

"Why don't you tidy them up as you show them to me?"

First Sandy pulled out her panties and showed them to Amanda. As she expected they were white or pastel cotton, mostly briefs, though Sandy had a few bikini panties with little designs. Then she held up her bras. They were all just one step away from training bras, cotton or nylon, and very supportive. She had one jogging bra, Amanda noticed.

"What size do you wear?" Amanda queried.

"32C", Sandy said. Amanda was impressed.

"What kinds of tights or hose do you have?" Amanda asked.

These were in the bottom drawer. Sandy pulled out mostly leggings and knee socks. She had one pair of pantyhose--"I wear these for dress up occasions"--and one pair still in a package.

"Hmmm," Amanda was thinking. "We have a lot to do. From now on when I come to babysit you, I want you to dress for me. Wait 'til I get here and your mom leaves. I want this to be a surprise for her. But you can get ready by showering and doing your nails. Yes, we're starting from scratch! For this Thursday, just put on some clear nail polish and your skirt and top that you like. Have them ready for when I get here. Also, and again, do this after I get here, put on a little lip gloss. Then we'll zip on over to the mall and start looking at all the possibilities. We won't have much time to buy anything cuz we want to be back by 9:30 when your mom gets home. But it'll be a start. I'll make sure to borrow the car, and maybe I'll dress to show off a few things for you. How does that sound?"

"Oh, Amanda, this will be so much fun!" Sandy said.

At that moment they heard a sound from downstairs. "Yoo-hoo," it was Sandy's mom. The whole evening had passed.

"We're in my room," called Sandy.

"Well, I am impressed!" Sandy's mom said as she entered her daughter's clean room. "You will come back on Thursday?"

"You bet!" Amanda said as she turned and winked at Sandy. They both smiled thinking about what was to come.


"Yes, dear, is anything wrong?" Mrs. Berensohn, Sandy's mother, had just been been put through to her daughter.

"No, Mom, I was just wondering how to do a load of laundry. You showed me once but I forgot," Sandy said blithely.

Though initially she was surprised by the question, Mrs. Berensohn breathed a sigh of relief that her daughter was alright. Or was she? Wanting to do a load of laundry? She quickly ran through the steps before Sandy changed her mind and hung up still shaking her head in disbelief.

It was Wednesday afternoon and Sandy was making sure to be prepared for tomorrow's visit from her babysitter. She laundered everything she would need as per Amanda's request.

On Thursday Sandy could hardly concentrate on school work. As soon as she got home she showered, and, dressed in her robe, worked on her nails. Then she dutifully did her homework and was just finishing when her mom got home and heated up some dinner. She was still in her robe when Amanda arrived. With a kiss from her mom she was left with her babysitter.

"Ok, I want to see you dressy and ready in fifteen minutes!" Amanda announced. Sandy bounded up the stairs and got ready. This gave Amanda a little time to check out the family room. Big screen TV. VCR. Nice stereo system. Even, it looked like, a video camera system.

"I figure we need to find you some good places to check out regularly at the mall. I want to look for skirts and tops tonight. But we'll also go into the Victoria's Secret shop as well. That'll still leave shoes and we haven't even begun with makeup yet. What are your favorite colors?" Amanda quizzed her as they were driving to the mall.

The first shop they went to was called 'Hot Topic' and they looked at the array of short skirts and hip huggers. There were racks of stockings and tights, fishnets and body stockings. "There may be some things I'll want you to get here. This won't be the main place."

The next place was called 'Wet Seal'. Here they spent a long time. They had a great selection of animal prints, skirts of all kinds, even some dresses that Amanda admired. "Why don't you try on a few of these skirts? We want you to go home tonight with something!"

They ended up with a tight black skirt that came to about three inches above her knees, a paisley, filmy skirt that was fuller but also short and a purple satin stretchy skirt that came to mid thigh.

"So, what do you think?" Amanda asked as they walked out.

"I love them!" was all Sandy could say. She was in kind of a daze of excitement.

"Uh-oh, we've got to hurry," Amanda sped up. "We have time for one more stop and it has to be the lingerie shop."

When they got there Amanda said,"It's time you completely changed your undies." Amanda had this way of making announcements that caught Sandy off guard.

"Oh, you mean I need a new wardrobe of underwear?" she said after a few moments.

"Yes," Amanda said immediately. "You need these over here," taking her to a table of satin bikinis. "And some of these," holding up a pair of thongs. "And don't be afraid to get matching sets of panties and bras. And as for bras you have to get several Wonderbras--your figure will really be enhanced with them. And some sheer ones with and without underwire. And at least several demi-bras. They will look fantastic on you!"

Sandy's head was spinning but she took it all in.

"So you know where to go? I'm giving you an assignment for over the weekend. You've got to come here because I want you dressed in your new clothes top to bottom next Tuesday. Ok?"

"Yeah, sure," Sandy said.

"Look at the time! We've got to get you back home," Amanda said as she drug Sandy out of the store. They zipped home just in time to put Sandy's purchases away, bound down the stairs, and greet her mom as she returned from her class.

"See you next Tuesday!" Amanda said to Sandy as she scooted out the door.


Amanda called Sandy the next afternoon. "You know that when you shop for panties they need to fit you very well, so if you're wondering, go with the smaller size." Amanda continued with shopping instructions for her new charge. Sandy for her part was thrilled to have this attention; she hadn't expected to talk to Amanda today. Her call got her to planning her shopping trip tomorrow in even greater detail.

After hanging up, she told her mom, "I'm going to need some money for clothes. I want to buy a bunch of new stuff!"

"All right, dear, how much will you need?"

"Three hundred maybe will cover it. I want to get skirts and underwear."

"Ok. If you need more call from the store and I'll see what I can do," her mom said. Sandy was all set.

In the end Sandy did have to call her mom from Victoria's Secret. Since her mom had an account there arrangements were quickly made, and Sandy came home with bags of new things.

When Tuesday finally arrived she had tried everything on at least twice and had it all laid out for Amanda's inspection when the doorbell rang.

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