The nanny's new baby.

Chapter 1
Arival

Chapter Description: A nervous Penelope discovers what may be the home of her dreams, with a few strange caveats...

I don't think I've ever been more scared in my life. Let me explain a little. See, I'm a girl, but not really. I was born as a boy, but I don't like being that way. I hate my... genital area. It feels like a cancerous growth between my legs. I can feel a weird tingle where my breasts should be, it really hurts sometimes. So I bought some women's clothing. A skirt, some panties, and a pair of short shorts. I loved it. I felt so cute in them! I was like a real girl, a perfect little princess! Then Dad walked in. He screamed at me and came pretty close to hitting me. He and Mom immediately looked for ways to "fix" me. Then Mom stumbled upon this person. They wouldn't tell me where I was going, they just put me on the plane and sent me off. 

It's probably going to be horrible. But, I'm 18 now. I can run away once the plane lands. I can feel the whole thing shake as it touches down. I got off the plane, taking what little luggage I had with me. Mom told me that this person would provide clothing, which I could only assume meant a uniform of some sort. I carried the small bag of essentials off the plane and walked out through security. As I walked that way, I felt like I was going to pass out from nerves. I wanted to go home. I wanted to crawl into the loving arms of someone who understood me and have them tell me they understood me. I was shaking and shuddering as I walked into the meeting area. I saw someone with a sign that said "Green" on it. It was a muscular woman with long black hair. They where dressed in plain looking street clothing, and it didn't seem to fit them. I walked over to them and nervously greeted them.

"Uhh... Hi." 

"Are you Green?" Asked the woman.

"Nope. But that is my last name." I said. I wasn't sure if she got it. I felt a bead of sweat run down my forehead. The woman laughed a second after I said the joke.

"Ha! Mistress likes a student with a sense of humor. Come on now, let's go meet her." Said the woman. The two of us walked out of the airport, and got into a modest looking car. The backseat was massive, with two rows and enough to fit around six people. Where there others? Would I be able to talk to them? I felt my eyes well up with tears as we began to drive. The woman didn't seem to talk much notice. I remained silent as we pulled up to a large house at the end of a cul-de-sac. We walked inside, and sat down. Well, I sat down. The woman left, presumably to fetch the "mistress." I wanted to sink into the plush folds of the sofa and hide there forever. The shiny wooden floors and homey decorations where doing nothing to cure my anxiety. I was about to make a break for it when the muscular woman walked back in, wearing a maid outfit. The other woman was a tall, imposing woman with a business uniform on. She looked like a strict teacher, and carried herself like a drill sergeant. 

"This is her mistress." She said, curtseying to the "mistress." Wait, her? She called me a girl! 

"Thank you Lucy, I'll take it from here. Mrs Green, what's your name? Your REAL name." Asked the woman. 

"Penelope Ma'am." I told her.

"Penelope. I'll probably be calling you Penny then. Your Mother sent me a very strongly worded email about you not being a real woman. I intend to fix that. By the time I'm done with you, you're going to be a proper, obedient lady." Okay, so she had some weird hangups about gender roles, but I could work with this! She was going to call me by my real name! I wanted to run over and hug her, but I just sunk into the chair out of relief. "I won't be going easy on you. Especially since you're new here, I know I'll need to set you straight fast and hard. Stand up Penelope!" Said the woman. I immediately stood at attention. I was both giddy and nervous now. She called me Penelope! I am never going to get sick of that. "Lets go over the rules first. Are you listening Penelope?" Asked the woman.

"Yes Ma'am." I said.

"Good. First rule is this: I am in charge here. Lucy is below me, but she is above you. Anything Lucy or I say to do, you will do without question. Understood?" So listen to everyone here? Okay, I was expecting that. 

"Understood."

"Second rule. The privilege system. I decide wether or not you have been good enough for something, or are properly suited to it. If you do not have privileges for something, you will not interact with it at all. Understood?" Thats a little weirder, but I can accept it.

"Understood." 

"Lovely. There will be no cursing, or dirty language in my house." Normal rule again. Fine with me. She went through a few more rules that where expected. No "self pleasure", no screaming or yelling, no hitting. Normal rules. It was the last one that really made me raise an eyebrow.

"Final rule: Punishments. If you are disobedient, then you will be taken over my lap for a paddling. Other punishments include timeouts, early bedtimes, and punishment plugs."

"Punishment what?" I asked.

"Punishment plugs. Buttplugs of varying size that I will leave in your anus for various amounts of time as a punishment. Since you where born into the wrong body, chastity cages are not off the table." Said the woman.

"Lady, that's... can we not do that?" I asked.

"I will punish you as I see fit. You will call me Mistress. I will answer no other name." Said the woman. Okay, Mistress. This is weird. Like its designed for someone younger than me. If you took out all the sexual stuff, these rules would work pretty well for a five year old. But I was still grateful that this wasn't just conversion therapy, so I would play along for now. "Now then, take off your pants." 

"What!?" I asked in shock.

"You are a lady. Ladies wear either skirts or dresses, never pants in my house." 

"You're wearing pants!" I shouted at her. 

"No shouting. I am a woman, not a lady. There is a difference. Now, pants off. You do not have pants privilege." I was embarrassed and confused, but I didn't want to make her mad. So I pulled off my sweatpants, my face turning red as I realized that I had worn the only pair of panties that I had managed to save from my parents.

"S-sorry..."

"You do not have panty privileges. Off." 

"No! Not happening!" I shouted. Mistress snapped her fingers, and Lucy came back into the room. She was carrying a large wooden paddle, a grey school uniform, and what looked like a thick pair of pink underwear. I gulped at the sight of the paddle. I took off my panties and handed them to her. She stepped aside and let Lucy take them. I stood there, my face beet red, covering my crotch. 

"Oh do calm down, I've seen more than enough boy bitties in my lifetime. All the rest, now." Said Mistress. This was getting very fucking weird. But I obeyed. I handed off the rest of my clothing, and Mistress passed me the clothing that Lucy had brought in. I was about to put it on when Mistress held up her hand. "Underwear first Penelope." She handed my the thick pink underwear that Lucy had carried in. It crinkled as I held it. It had a childish cupcake design on the front, with little sprinkles on it. Everything was pink, the cupcake and sprinkles being a soft purple. "Do you need help getting dressed Penelope?" 

"What! No, no I don't!" I shouted, stuttering. I felt the paddle strike me harshly on the butt. I let out a little yelp as Mistress hit me.

"Indoor voice Penelope. Now then, get yourself dressed." Not wanting to incur the wrath of Mistress any further, I pulled up the strange underwear. It was padded with a softish cloth on the inside. These where for bedwetters, I realized. She really didn't trust me at all. It was embarrassing, but I could probably get back to adult clothing soon. I put on the rest of the outfit, and Lucy pulled closed a door with a full length mirror on it. I let out a squeal of excitement as I saw myself. I looked so cute, I looked so pretty, I looked so... ugly. Oh god, I have the start of a beard. I whimpered a bit as I stared intently at my little bit of facial hair. 

"You look lovely Penny." Said Lucy. I blushed and did a little twirl, letting the skirt rise into the air a bit. Lucy snickered as my pull-up was shown off from under the spinning skirt. 

"We should get started Penelope. Follow me." Said Mistress. She opened the door with the mirror on it, and I followed her through. The pull-up was strange, as where the rules, but her first impression of me had been from my angry Mother. This would be gone soon. As I walked through the hallway, I noticed a large pacifier lodged behind a book.