The Babysitter
Chapter 1

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

Desc: 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.

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.


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.

"I'll get it!" Sandy called out. Her mom was still getting ready for her class.

At the door Amanda gave her a package and said, "As soon as your mom goes, start with this pink nail polish and eye shadow. Then put on your first new outfit and come downstairs. I'll wait for you in the family room."

Sandy raced upstairs with the cosmetics. She said goodbye to her mom and went to work.

"I may be a little late tonight. Is that ok?" Mrs. Berensohn asked Amanda.

"I think so. How late is late?"

"Probably 10:30."

"Yeah, that's ok. I brought plenty of homework. Does that mean Sandy should go to bed before you get home?"

"Oh, yes, if you can see that she's in bed by around ten."

"Sure," Amanda said.

"One more thing. The first workshop that I mentioned is the weekend after this coming one. Can you stay here then? I'll pay you three hundred dollars if you could be here right after school on Friday and stay 'til around three on Sunday afternoon. Of course there would be food here stocked for the weekend."

"Yes, I can do that." One of the attractions to the job even before Amanda knew Sandy's age was the money she would make on these weekends of babysitting.

"Good, then it's settled. Have a good evening."

"Study hard!" Amanda said pleasantly.

No sooner had Mrs. Berensohn driven away then down the stairs came Sandy. She bounded into the family room twirling and showing off. As she came to rest, Amanda took in the transformation. She had put on a pink, pleated satin skirt and a white, short-sleeved cotton blouse. Her nails looked nice with the outfit, but she'd hurried through putting on her eye shadow. Still there was great potential here, thought Amanda. Now she had to get her used to this next part.

"You look nice!" she said with real warmth. "Did you get any new underwear like I asked?"

"Oh yeah!"

"Let's see. Just unbutton your blouse part way." Amanda said it in such a nonchalant way that Sandy didn't hesitate. She was excited to show off her fancy new bra.

"Wow, did you get it at Victoria's Secret?"

"Yeah, I got all my undies there!"

"Let's see your panties, do they match?"

Sandy lifted up her skirt. She had chosen a matching cotton floral bikinis and triangle bra set.

"Cool! Now let's go up and work on your makeup some." So they spent the next hour in front of Sandy's mirror. Amanda was jealous of her having her own bathroom. Amanda had brought her whole makeup collection and very patiently showed her secrets with eye shadow, mascara and lipsticks. She also made Sandy write down supplies she should get to have her own collection.

After the hour, they both looked in the mirror. Sandy was starting to look very dreamy, thought Amanda. "It's so important to go to bed though with your face absolutely clean. So don't forget to write down those cleansing supplies too. Now let's see what else you bought."

Sandy started to show her, but Amanda said, "No, you have to model them for me. I'll wait downstairs."

This time she was wearing a black short and rather tight skirt and a leopard print top. The top was tight enough to accentuate Sandy's breasts. With the addition of her makeup she was starting to look hot, Amanda thought.

"There's something missing..." Amanda started.

Sandy's face fell, but Amanda said, "No, don't get me wrong, this is a great outfit. You're looking so grown up. It's your legs. They're bare. Come here," and Amanda motioned her to come next to her. "Let me feel your legs," and she did before Sandy could react. "Just as I thought. Ok, you have a lot to do for Thursday. First, what's missing is hose. You need to be wearing hose. Black would look so great with this outfit. But you're going to need to shave your legs. Have you ever done that before?"

"Yeah, but not in awhile. I was mostly just messing around," Sandy said a little embarrassed.

"Well, from now on, you need to keep your legs silky smooth. I'll give you some stuff that will help. For Thursday just make sure to soak yourself in a nice warm bath and use a new razor, ok?" Before Sandy could answer Amanda continued, "And you need to get some nice sheer pantyhose. Can you go to Victoria's Secret again? Before Thursday?"

"Sure!" Sandy quickly said.

"Good, now show me your undies."

This time Sandy didn't hesitate to pull off her top. she really wanted to show her this pair. She skimmed out of her skirt as well and stood in front of her babysitter. She wore a boy-cut brief and matching bra in black satin.

"Wow, these are fantastic! How do they feel?" Amanda noticed that the satin briefs were nice and tight. "Turn around for me." As Sandy turned her tight ass shown in the lights on the glossy underwear.

"They feel so good!" Sandy replied.

"Did you get anything else?"

"Just some more underwear," Sandy said.

"He he he, ok, let's continue with the underwear modeling!"

The rest of the clothes that Sandy modeled for Amanda were nice though not as striking as the black satin set.

"Didn't I ask you to get some thong undies, too?" Amanda asked as Sandy turned to go.

"Uh, yeah, and I did, but I was a little embarrassed to show them to you."

"Oh, come on, I'm your 'fashion adviser', there should be no secrets from me!" Amanda chided.

"Ok, I guess," and Sandy went to change. When she came back she was wearing her nightgown.

Sensing her hesitancy, Amanda said, "Ok, just pull up your gown and I'll check 'em out."

Sandy did what she was told, albeit slowly.

"Hmm," Amanda said. "Now turn." The thong looked good on her, really good, thought Amanda. Her butt cheeks were full and round. The thong fit tightly and disappeared into the crack of her ass. But Amanda soon saw why Sandy was hesitant. "More homework, Sandy," she said with a grin. "You'll have to trim your pubes. Then these will look great and feel better too."

"My what?" Sandy asked.

"Your hair down there, your pubic hairs." Again Amanda was so matter-of -fact that Sandy accepted her direction immediately. "Just use some sharp scissors. It'll be good for when you wear a real bikini anyways. Ok, now off to clean your face, brush your teeth and into bed. Your mom will be home really soon, and you were supposed to be in bed fifteen minutes ago!"

Sandy dropped her gown and gave Amanda a big hug. "Thank you so much for tonight! It's been so much fun!" Then she gave her babysitter a big kiss on the cheek and ran off to bed.

Amanda had just settled in to some history homework when Sandy's mother drove up.

"Everything ok?" Mrs. Berensohn said as she came into the family room.

"Everything's just great!" Amanda said. "I'll see you Thursday."

By Thursday Amanda had done some shopping as she well hoped that Sandy had. When she rang the doorbell she not only had some supplies for Sandy to use on her legs but some hose in Sandy's size and a few surprises as well. She wanted to get on with this dressing of her 'protege'.

Sandy answered the door, excited as ever, and Amanda gave her some purple sparkly nail polish to use for tonight. Sandy said goodbye to her mom and went straight to her room to dress for Amanda. After Mrs. Berensohn drove away, Amanda came up and gave Sandy the stuff she'd promised to bring.

"I'll wait downstairs for your entrance," Amanda encouraged.

Sandy had worked on her makeup constantly since Tuesday. She'd chosen a striking blue eye shadow, and, upon seeing the nail polish that Amanda had given her, a lipstick that was purplish to match her nails. She took longer this time and the effect was dramatic as she made her entrance.

She was wearing the pink pleated skirt again, but this time with black fairly sheer pantyhose and a black top. Her makeup just set off the whole outfit.

"Oh my, you look divine!" said Amanda. "From now on you will always wear hose for me. Come over here. I have some surprises."

They sat down together on the couch and Amanda pulled out what she had bought for Sandy.

"These are stockings, several different colors, and here is a garter belt which should fit you. These feel so nice sometimes. I bought them extra sheer so be very careful when you put them on--they're awfully easy to run. In fact on most occasions I use gloves to put them on. They're expensive, the more sheer they are, and gloves like these work really well." She handed Sandy a pair of sheer nylon gloves. "Now I don't want you to try them on tonight cuz I want you to use the supplies I brought you for keeping your legs very smooth. Ok?"

"Yeah, sure," Sandy responded, amazed at how much she was learning from Amanda. "Where did you get these stockings?"

"I ordered some of them special cuz they're hard to find in regular stores, even Victoria's. I'll give you the addresses. Some you can order online. Will your mom let you do that?"

"Oh, sure, she's already let me get stuff online."

"Good. But there's also one place in the mall. Remember 'Wet Seal'? Well, right next to them is a place called 'The Company' that gets in nice stockings especially from Europe. That's where you should go."

"Cool!" Sandy was feeling so grown up.

"Do you have any heels?" Amanda asked.

"Well, I have two pair. Do you want to see them? My mom has so many pairs of shoes!" Sandy said almost as an afterthought.

"Oh, really?" Amanda perked up. "Can I see them?" Amanda loved shoes. She was secretly hoping they would fit her.

"Sure, I'll get mine too."

When Amanda had seen Sandy's shoes, she said, "Those are cool. We need to get you some more pairs, with higher heels and I like open toes."

"Ok," it seemed like Sandy was agreeable with whatever Amanda suggested.

When they got to her mom's room, Amanda gasped at the selection. She jumped up and down when she saw that they were her size. This made her curious about the rest of Mrs. Berensohn's wardrobe. But that could wait.

"Let's do some stepping out!" Amanda said.

"Huh?" was all Sandy could say before Amanda had tried on a pair of Mrs. Berensohn's shoes and headed downstairs to the stereo.

"What music do you have?" Amanda asked.

Sandy wanted to impress her so she got her favorite CD and put it on.

"All right!" and Amanda started dancing. She had worn a short skirt and hose to encourage Sandy. With Mrs. Berensohn's heels she felt especially hot and pulled Sandy in to the center of the room to dance.

Sandy was glad to join in and she soon let the total experience--being dressed up, made up and in the presence of this cool high school girl--wash over her as she danced.

After they'd danced awhile, Amanda stopped the music. "It's getting close to the time your mom will come home. You look so cool! Don't forget what I told you. Now over the weekend can you find some shoes like I described?"

"Yeah, I love trying on shoes!"

"Good. You know that we will have a weekend together soon? I'm really planning on us doing a lot for your 'look' over that weekend. Ok?"

"I can't wait!" Sandy had been thinking about it ever since her mom had told her.

"Good! So go get ready for bed. Make sure you clean your face super good. You can leave the nail polish on. It looks really good. You're getting to be quite a professional already!"

Sandy was so happy when she heard that. She loved pleasing Amanda.

Not long after Mrs. Berensohn came home. "So we're all set for next weekend?"

"Yes, I'll be here Friday afternoon."

"Good. Tell me, dear, what food you like so I can be sure to have it for you."

Amanda gave her some things she really liked, but she was thinking of other treats she might get that weekend.

On Tuesday afternoon, Amanda called ahead to Sandy to tell her to have her nails done before she got there. "Your mom is not saying anything this week about you wearing nail polish, is she?"

"Nope, she hasn't noticed," Sandy answered.

"Good, then you should do your nails before hand. You remember that I want you to wear hose when I am there, right?"

"Oh, god, yes," Sandy said quickly. It was all she could think about. It was so new to feel the silky sensation and her legs so bare. She loved it!

"Ok, I'll bring another surprise tonight. See you soon!"

For the first time when Sandy presented herself to Amanda after Sandy's mom had left, Sandy looked properly dressed. Her makeup was very subtlely done and she wore a great pair of pantyhose with a short skirt and her other heels. She strutted and vamped for Amanda who felt almost underdressed for the first time. Then Amanda gave her the surprise--six packages of thigh high stockings, the sheerest kind she could find, in black, red, purple, white and tan. Two pairs of black ones of course. She gave her all kinds of instructions on when it was best to wear pantyhose, thigh highs or stockings and ended her instructions with saying, "Unless I say differently you should just assume that you should wear pantyhose for when I am coming over."

"Ok," Sandy said.

For Thursday Amanda made her change into the garter belt and stockings. While Sandy did that Amanda had time to go into Mrs. Berensohn's closet and check out her wardrobe. There were many dresses that Amanda was interested in trying on. She also checked Mrs. Berensohn's drawers of underwear and was amazed to see all kinds of sexy things. Then she peeked into her rows of shoes and realized this coming weekend would be a great dress up weekend for the both of them.

"Ok, so I'll be here tomorrow when you get home from school. The first thing I want you to do when you get home is take a shower and get all shaved and smooth. Then we'll have a modeling session like you wouldn't believe!"

"I can't wait!" Sandy said.

"But you mom mustn't know about any of this! Ok?"

"Yeah, this is cool!" Sandy said.

"You look great in these stockings, by the way," Amanda said as she stooped down and felt Sandy's stocking covered leg. She went so far as to bring her hand up to the place where the hose was attached to the garter belt.

For a moment Sandy was dizzy from the caress. It was the most sensuous thing she had ever felt!

Before she could say anything though Amanda said, "You better go get ready for bed, your mom will be home soon."

And that was the last Sandy heard from Amanda before the fateful weekend began.

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Story tagged with:
ft/ft / Reluctant / Lesbian / First / Babysitter / Transformation /