How I was Trained Pt. 02

How I was trained

My first chastity cage part 2

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All I could think about all week was how pretty I looked when Miss Baxter finished with my makeover last Saturday. I honestly couldn't wait for next Saturday.

I thought a lot about why what someone else thought about what I looked like while I was dressed in girls' clothes bothered me so much. I kinda got my answer when I wore a slightly pink T-shirt to school. Mom ruined my shirt in the wash but I still liked the shirt.

I got teased all day and decided I wouldn't wear it to school again.

It really bothered me. My path home takes me right past Miss Baxter's condo. She was standing at her front door. She saw me and asked how I was.

I mumbled something to the effect that I was ok or something. She asked me to come inside for a second so I did.

On the kitchen table was a shopping bag with a box in it.

It's for you. But you'll probably want to leave it here, she said.

I sat in the chair slouched over almost sulking really when she asked me if everything was okay.

Not really, I told her. I can see that but you'll have to tell me, I'm not exactly a mind reader you know.

I know Miss Baxter, it's just that everyone at school today was teasing me about the color of the shirt.

I think it looks just fine.

You would, it's a girl's color, I said.

No, no it is not a girl's color.

Then why did everyone bug me about it all day?

We're the girls bugging you or was it just the boys?

I don't know, I guess just the guys.

Well, boys will always try to make themselves look mucho in front of others. That's just the way it is.

Do you recall what you were feeling last Saturday when we sat in plain view of the world to see and you were relaxed while we sipped tea?

Yeah, but that was different.

How? How was it any different?

You weren't teasing me.

I wasn't teasing you, I was encouraging you to be something different. If you want to be the same as everyone else then why did you agree to be trained?

That's my secret side, no one's supposed to know about that side of me I said as a tear rolled down my cheek.

So why did you show me?

I don't know, maybe because I trust you.

And you don't trust your friends at school.

Not with someone like this, no way. They would tease the shit out of me, you know that.

You're right. I do know that but before last Saturday, you didn't know how good it could be to be fully you.

My point is, you can't allow others to tell you how to feel about your true self. No matter how embarrassing. You are you, all others be damned. Do you understand?

So what do I do about the guys making fun of me?

If you make fun of yourself it won't be as fun for them.

She hugged me and asked if I wanted to open my present now.

I wiped the tears from my eyes and reached for the box.

When I opened it my eyes lit up. Inside was a bra and panty set with a garter belt and pink stockings. A huge smile stretched across my face as I stood up and hugged her hard.

I'll take that as you like it, she says. Look under the paper.

Under the paper was a pink satin corset.

I love it, is it really for me?

Of course. I hope it fits.

I can't wait to try it on. We can be girlfriends all day.

She just smiled.

I gotta get home. Mom's waiting for me.

The rest of the week seemed to just fly by at warp speed. Nobody could ruin my mood.

Friday after school I walked past Miss Baxter's condo as usual but the curtains were closed. I immediately thought, was she with somebody else in there today?

It didn't really bother me that much so I continued home.

Saturday morning I was up and ready to go. As usual, Mom was working on her second pot of coffee, probably. She asked where I was going. I told her Miss Baxter and I had plans.

Plans? What kinda plans?

I'm not really sure. She gets me to help her move things around her condo. Gotta go now Mom. Love you, I'll be home later and I ran out the door.

I got to Miss Baxters a short time later and knocked on her door. After a bit of time went by with no answer, I knocked again. Confused, I looked in the window but didn't see anything out of the ordinary.

I walked around the building to the other door and found her sitting on the step.

Hey Miss Baxter I said as I walked up to her and sat beside her.

She didn't say or do anything. She just sat there.

Is everything okay, I ask?

Not really, was all she said. Sensing she was feeling down.

I bumped her shoulder with mine saying cheer up Miss Baxter. We are gonna have so much fun.

She just smiles and says maybe next week bud. I'm not feeling so hot today.

Are you sick or something?

No, I just want to be alone.

But I thought we had plans. We were gonna try on my new clothes, remember?

I remember. I tell you what, you go ahead and get yourself all dressed up and come show me how you did, okay?

She told me this with a bit of a Mischievous look to her.

She didn't have to tell me twice, I ran inside and straight to the basement. I sat in the vanity and applied my make-up as best I could then put on my new pink bra, panties, and stockings with a garter belt on. I stepped into the training heels and locked both locks. And then picked out a black and white maid's uniform. Last came the long blond wig.

I stood in front of the vanity mirror admiring myself. Although I didn't look as good makeup-wise as I did when Miss Baxter did it I was somewhat pleased.

I went upstairs to find Miss Baxter still sitting on the step outside. I stayed inside and asked her how I looked.

You're behind me she said.

Yeah, I know. Can you turn around and look?

How about you come out here so I can have a good look at you, she says.

Outside? I uhm. I don't know.

The sun is shining, no one is out here but me. Come on. You can do it.

I stepped closer to the entrance nervously looking around. She sat still, her back to me.

Are you sure I nervously ask again?

She looked both left and right and said, yes it's all clear.

I cautiously stepped out the door and looked all around.

Even more cautiously I stepped past her and down the two steps. I stood in front of her nervously looking everywhere.

She smiled and told me to never forget the feeling of being free to do things outside my comfort zone.

I'm not gonna lie, I was scared shitless someone was gonna see me. She stood up and took my hands, holding them to the sides. She says the maid's outfit? Interesting choice.

She hugged me tight for a while then sat back down. She patted her hand on the step so I sat beside her.

She asked what I was wearing underneath the dress.

I told her my new lingerie.

She smiled and asked if I had the same problem with the panties as I did last time.

A quick thought and I told her no. I didn't. Of course, now that I was thinking about it my little boner started to stretch the fabric of my panties.

Miss Baxter somehow noticed and told me she's gonna have to do something about that if I couldn't.

Like what I asked as I turned red.

Oh, I have my ways, don't you worry about that.

I slowly stopped worrying about being seen outside dressed after a while.

Miss Baxter told me hardly anyone ever comes out this side of the condos. They Are more like row housing. Six units to a building. Each with three floors. She lived in one of the four inner units. There's an open field with a bunch of trees at the far end.

We talked outside for quite a long time then she asked if I was hungry.

Yes ma'am I said.

Good, seeing as you're in the maid's uniform, you can go make us some lunch. You'll find everything in the kitchen.

I was a bit surprised but thought okay, I guess I'd better make lunch then.

I went inside, I made little sandwiches like she made last time with a slice of ham and a small piece of cheese. I made tea and when everything was done I brought it outside on a tray. We sat on the step and ate. She didn't seem to like the tea too much but it was the first time I'd ever made it.

When we were done I took everything back to the kitchen.

She followed me and told me I'd better clean this mess up as I was in the maid's uniform after all.

She went upstairs and I got to work.

I was almost done when the doorbell rang. I almost shit myself hoping no one saw me.

Miss Baxter came down and answered the door.

I could hear her talking to someone but couldn't quite make out what they were saying.

Then, clear as day I heard my friend Mike say he wanted to come in.

I couldn't get out of the kitchen because of the layout of the condo. He would have seen me.

Miss Baxter told him no in a very stern voice. Then it seemed as though they were whispering.

I heard the door open and close, then Miss Baxter entered the kitchen.

She smiled and told me I did a great job cleaning up.

She saw how scared I looked saying you can relax now. He's gone, she assured me.

That was Mike I told her.

Remember your promise? You promised not to tell anyone, Miss Baxter asked.

Yeah, I know but Mike? He's one of the older kids in the neighborhood. I've known him forever. There's no way he likes this as I slid my hands down my sides.

Remember, I also promised not to tell, she said.

How long has he been dressing up, I ask.

She stays silent.

I'm gonna ask him then I told her.

You can't ask him without revealing yourself, my girl. I don't think you want to do that. Do you?

She smiles and says do you feel that? That's jealousy. That can get you in more trouble than it is worth so stop it!

I can't and won't tell you anything about him or any other boys that I've trained.

Wait, there's more?

She put her hands on her hips and sternly told me to stop or I would not be allowed to come by any longer.

Not wanting to stop dressing up I bowed my head and mumbled yes ma'am.

Excuse me? I can't hear you!

Looking up I say yes ma'am a bit louder.

She smiles and says, that's a good girl. Now downstairs with you. I have something that you'll have to wear from now on.

I went downstairs. She followed. She told me to take my panties off and cover my face with a pillow.

The thoughts running through my head were mind-boggling. Of course, by now my little boner was at full attention, all inch or two of it.

What was she gonna do to me?

A short time later I felt her get on the bed with me. She didn't say anything. Then I felt her hand on my inner thigh.

She slowly slid her hand up closer to my dicklet. There was no way I could stop it. It just went off all by itself. Shooting little bits of cum all over. She covered my little penis with her hand and then wiped me clean with a cloth.

There, that wasn't so bad was it she asks.

I went to take the pillow off but she stopped me saying no, I have to keep the pillow in place until she says so.

Okay, I said.

She massaged my tiny little balls and squeezed my dicklet a bit then wiped it off again.

Then I felt something hard on my balls. I felt a squeezing feeling, then it felt like my dicklet was being pushed into my crotch. I felt a squeezing on the head of my dicklet and a pulling feeling.

I asked her what she was doing, she said she was almost done.

Then I felt my dicklet being pushed in again. Then she pulled on the skin on my balls and said there. All done. You can put your panties on again.

I took the pillow off my face and sat up. My tiny little penis was in a pink gadget.

Confused, I asked what it was.

She smiled and told me it was a chastity cage and from now on, I was to wear it at all times!

I didn't understand at the time what it was for. All I knew was she handled my dicky and that's all I cared about right then.

I got up and put my panties on. I couldn't feel the silky feel on my penis anymore but the feeling on my tiny little balls was out of this world. I could feel my dicky trying to get hard but it couldn't. The ring around my tiny little balls got a bit tighter but that's it.

She told me this will help me feel more like a girl.

So you feel like this I ask.

No, not exactly. I'm a woman so I feel like a woman. You're a boy so you'll have to be trained how to feel like a girl.

I was confused but didn't care at the same time. A woman had held my penis for the first time in my life.

She asked me to sit in the vanity so she could fix my make-up.

When she was done we went back upstairs. She had me practice walking in high heels again. I was feeling much more confident as I strutted my stuff.

It was getting late so I changed back into my boy clothes and she washed my make-up off but she told me I needed to keep the cage on.

Confused, I ask how do I pee with it on?

Just like a young lady does, you sit. Oh, and you can come tomorrow at 6 Am. I have a surprise for you.

Six?

Don't be late. Trust me, you're gonna love it.

I headed home wondering what she had planned for me