How I was Trained Pt. 04

How I was trained

Sex as a boy vs Sex as a girl part 4

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I hadn't asked my mom anything about going with Miss Baxter on the weekend by Wednesday. I wasn't sure she would let me, even at my age, to be honest. So when I got home from school and Miss Baxter and Mom were in the living room talking, I was pretty surprised.

Hey kiddo, Miss Baxter says to me. I thought I should introduce myself to your mom seeing as you spend so much time with me lately.

My mom was just sitting there with a smile.

I told your mom how much we love going to church and wanted to know what you felt about it.

Looking at my mom I told her I really liked going to church with Miss Baxter and I was hoping she would let me keep going.

My mom has always told me she believes in God but doesn't go to church, probably because of my dad. He is a non-believer.

Then she said she had no problem with me going to church if I wanted to go.

Thanks mom. I said as I turned to go outside.

Miss Baxter has asked if you can sleep over at her place on Saturday nights so you two can get an early start on Sunday. I wish the church was a lot closer but it's an hour away from the city, mom says.

So what do you think? Can I?

I don't see a problem with it, but you better be on your best behavior, my mom said with a stern look.

I had no idea Miss Baxter was thinking that but it made me happy all the same. I ran up to mom and gave her a quick hug and kiss to say thanks mom, you know I will. Then I ran out the door.

The rest of the week flew by with a blink of an eye.

Saturday morning had me up early as usual. Mom had breakfast ready for me so I ate while we talked.

She seemed happy I was helping Miss Baxter so much. I told her she helps me a lot too. I almost slipped up but I caught myself. I told mom she helps with lots of things.

She handed me a duffel bag with clothes in it and told me to behave myself.

I got to Miss Baxters condo just after nine. She was downstairs, is what the note on the door said.

After closing and locking the door I went down.

She had an outfit picked for me and spread out on the bed.

Today I was to wear a red bra and panties. A white long sleeve blouse and a long dark pink skirt. The skirt didn't give me much room to walk in. And speaking of walking, I'd be wearing a pair of pink open toe heels.

I didn't see the small little pink thing on the bed. It had a pink jewel type thing on one end. She picked it up and said, you forgot this.

She handed it to me, I studied it for a while and asked, what is it?

It is called a butt plug.

I didn't know what it was for but Miss Baxter would show me.

She had me bend over the bed and told me to relax. She was gonna push her finger in my bum.

I felt her fingers softly glide over my backside then I felt a cold liquid being squirted at my bum. Then very slowly she pressed at my bum hole. My little dicklet was trying hard to get free but it was no use. The cage held me tight.

Slowly she managed to get a finger inside.

She commented that I was extremely tight but she would make it feel wonderful and it did.

She pulled her finger out and then pushed it back in a few times. The more she did this the better it felt.

Then she pulled her finger out and I felt the soft yet hard plastic plug at my bum. She pushed it in and it kinda got sucked into the base. She wiped my bum with a wet napkin and I pulled my panties back up.

I got up and she told me I did fantastic. She was very happy with me.

It kinda felt like I had to go poop but different at the same time.

I asked why I wasn't wearing any stockings or pantyhose.

She got that mischievous look again and said you'll see.

I always get nervous when she says that.

Miss Baxter applied my make-up and placed my wig on then handed me a little white purse with lipstick and a small tube of lube, let's go.

I knew better than to ask so I just followed her upstairs.

We got in the car, it felt a lot different having the plug in when I sat in the car. We went to a place that does nails.

We both got manicures and pedicures. That's why neither one of us were wearing stockings or pantyhose. My fake pink nails weren't too long but they were longer than I usually keep them and my toes looked fabulous in the open toe shoes. We drove to a park and walked the paved paths for a while.

She told me she was very proud and impressed with me. Most boys wouldn't let a woman do even half the things she's done to me. But there was lots of work still to do.

She told me with summer break coming in three weeks, she was working on a big plan to get me ready for sex. As a girl!

When I asked her what that meant, she got the mischievous look again.

Don't worry Lisa, I'll take very good care of you.

You will start changing soon enough, she told me.

We headed back to her condo.

That night she took my chastity cage off and removed the but plug, she had me take a bubble bath and she shaved what little hair I had on my body. She told me to finish bathing and then come into her room

To be honest it felt really good to be free of it but I didn't really notice it too much in my everyday life.

When I was done in the bath I dried off and went to her room.

She was wearing a very revealing nightie. All I had was a towel wrapped around my waist.

My little rocket stood at attention right away.

Jump up here she said as she patted the bed.

I honestly could not take my eyes off her beautiful breasts.

Tonight you become a man, if you want. If you don't want that, it's okay too.

I looked up into her soft green eyes. I didn't know what to say or do really. I was pretty much frozen in fear, of course my little dick was super hard and it hurt.

Do you want to touch one she asks? Meaning her breasts. The lingerie she was wearing left absolutely nothing to the imagination.

With a shaky hand I reached over and held her left breast for the first time. My God did it feel so wonderful. She laid back and told me to do whatever I wanted to her.

My hands felt her breasts all over. I felt the softness of her skin and the hardness of her nipples, all the way down her flat stomach. I froze when I saw her pussy.

Then she took one of my hands and pushed it down between her legs. She reassured me it was okay.

She felt hot. Like fire hot down there. She allowed me to explore her pussy for a while then she put her fingers inside.

I just about shot off right there.

She told me to relax. That this is what true pleasure feels like. That to be a woman, you have to slowly build up the pleasure to the boiling point. To try your best to keep it at that point without pushing it over the edge. To enjoy the tease as much as being teased.

Then she sat up and said how about I show you how fast you can be pushed over the edge then I'll show you how going slow is so much better.

Okay I said.

She told me to lay back and cover my face with a pillow. So I did.

Then I felt something hot and wet on my boner. It felt like my dicklet was being stroked by something.

I peaked from under the pillow to see my dick in her mouth. I shot off right away. She held her mouth on my dick until it stopped but it didn't go soft. Then she did it again. Oh the feeling was so intense. I don't think she slid up and down ten times and I shot off again. Then she looked up to see me watching. She slowly slid down my little dicklet while keeping eye contact with me. When I tensed up, she stopped. After I settled down a bit she started sliding up and down again.

Every time I was about to shoot she would stop. She did this for a long time.

It got to the point all I wanted was to shoot. The exciting feeling and then being backed down again, then back up. Then she pushed a finger in my bum and I shot off a lot more than usual. I saw stars and then nothing.

I laid there thinking I had died or something. It was like hearing someone from a distance then getting closer until I opened my eyes to see Miss Baxter's breasts and then her face. She was asking if I liked it.

The huge smile answered her question. She laid beside me and asked if I thought I could do that.

I don't know, I said.

Do you remember what you were feeling when I was sucking your cock.

Oh yeah. I'll remember that for the rest of my life. I'm sure of that.

She laughed saying good. One day I'll have you prove it to me.

I just smiled.

I want you to lick my pussy now. Do you think you can do that?

Would you feel like I did just now?

Probably pretty close I think.

Will you show me what to do?

Of course I will.

Now get down between my legs.

I did as I was instructed.

She pointed to each part of her vagina telling me what it was and how to arouse her.

She had me lick certain areas softly and other areas more aggressively. But she never told me how good it was gonna taste.

I honestly thought it would taste like pee but it tastes like the sweetest nectar on the planet. The pure silky feel on my tongue was so good I didn't want to stop. My jaw was starting to hurt by now but I kept going anyway. Then she screamed out and made a low deep groaning sound. Suddenly there was a heck of a lot more sweet silky nectar to lick up and I did just that. She held my head tight and ground her pussy into my face. It really did feel like her pussy was trying to eat me instead of me eating her. She pulled me up and told me to put my dick in her pussy now. She was very aggressive.

I did what she told me. My dick slid in as she was still shaking. All inch and a half went in. It felt very wet like there was too much liquid but I pushed it in and held it there.

She told me to pull it out and push it back in again over and over. I think I got to do it twice and the third time I shot off, some inside her and some outside.

I collapsed beside her. She was playing with my hair as I fell asleep.

The next morning she woke me up and said we need to have a shower.

I was pretty tired still but got up and showered. As I was finishing she climbed in. She told me to dry off and wait for her in her room.

When she came out she put the smaller chastity cage on me. It was pink and looked kinda like a pussy. The hole where I pee from lined up perfectly. Next came the small butt plug. This time it went much easier and faster.

We went to the basement and she picked out a silky pink corset, bikini panties and garter belt with nude colored stockings. My pink toenails showed nicely in the open toe pink heels. She helped me tighten the corset to the point I could barely breathe then let it out just a bit. It really pushed what little fat I did have into my chest making it look like I had nice little titties.

Then came a beautiful blue dress that went down to the top of my knees. It showed my small cleavage just a little bit. It's a little shorter than usual but very nice all the same.

Miss Baxter put on an almost identical outfit but her heels were a slightly different shade of pink and she showed a lot more cleavage.

We got in the car and drove to the church.

We sat in the same spot, Ann and Tony were already there. Tony was checking us both out big time. We made some small talk then the sermon started.

I think the priest was preaching directly to Miss Baxter and I when he said conservatism must prevail if man is not to be seduced or something like that.

The but plug was much more noticeable sitting on the hard pews. I caught myself fidgeting more than a few times.

Tony put his hand on mine to calm me down. At least I didn't screech this time.

I know Miss Baxter noticed but she didn't do anything. It felt nice holding Tony's hand. I knew he liked me and I know I like him.

At the end of the sermon we all went back to Ann and Tony's farm.

The first thing I did was change out of the heels and into pink runners Miss Baxter got for me.

Tony and I said we were going for a walk. Ann reminded Tony about a hole in the fence so he grabbed some tools and we headed for the field.

Tony complimented me on my dress saying it made me look so pretty.

I thanked him and said only a gentleman would notice.

He smirked and said I don't know about that. Every guy at the church was eyeing you and Miss Baxter.

I just smiled and said well when you got it flaunt it.

Just then we got to where the hole in the fence was.

We talked a bit more while he started fixing the fence.

He was almost done fixing it. Then he asked me to hand him one of his tools. As I reached across a wet spot in the field he leaned in closer and kissed me.

At first I was like what just happened then he came in for another. I stood there and actually kissed him back.

He broke the kiss saying I'm glad I got that out of the way. He finished fixing the fence and we walked hand in hand much slower now. Once we were behind a bunch of trees he kissed me again, this time with a lot more passion. He put his hands on my bum and pulled me to him lightly. I did the same to him. I could feel something hard between us. We continued kissing the whole time. I could feel my little dicklet getting stuff. I stopped and stood there saying I'm sorry. I realized the hard thing was Tony's penis, I didn't mean to.

He stopped me saying it's

okay. We don't have to do anything.

I apologized again saying I know I caused him pain.

He laughed. Pain? That's pure pleasure, he told me.

I remembered what Miss Baxter told me about pure pleasure and turned back to him. He kissed me again, this time holding my arms and pulling me closer to him.

He slowly worked me down to my knees then stood up. He looked down at me while I looked up at him. My hands slid up his thighs and converged on his snap of his jeans. Then I slowly tugged the zipper down. He pushed his jeans down revealing his boxer shorts. My hands pushed up into the fabric feeling his manhood.

I'm not gonna lie, the size scared me a lot but I so wanted to pleasure him. My hand explored his cock in the fabric. Then he slid them down revealing the first cock I've ever seen in real life, other than my own and it was much smaller. It was WAY bigger than mine. Fear took over temporarily but I fought through it. I reached up with one hand and grasped the shaft.

The first thing I noticed was the hardness then the weight of it. Then the heat as I moved my face up to be closer to it. He moaned slightly through tight lips. My face is so close now I can smell his musky manliness. Using my nose I nudge at the head a bit. It responds with a jerking motion upwards. I moved closer to his big balls. My hand crept up to caress them. They're heavy and tight.

My mouth opened slightly, my tastebuds were going wild tasting the air then my tongue licked his tight balls. They respond by pulling tighter. His cock jumps again.

I slide my tongue up the underside of his beautiful cock. Tasting every inch I can. The hunger I felt at that exact moment was unbearable. While I held his big balls in one hand my mouth was working its way to the tip. The world ceased to exist at that moment. The only thing I wanted, no need to do was pleasure him with my mouth and salivating tongue.

My tongue left a wet trail from his balls all the way to the tip. Once I got there I licked the head all over. It tasted different, softer. More like a smooth sponge. I had a hard time getting his head in my mouth. But I did it. I remembered what Miss Baxter had done to me, so I did the same to Tony. I slid my mouth up and down his cock.

I couldn't get it all so I stroked his shaft with one hand and played with his balls with the other. Tony's moaning got a bit louder as I slowed down. As he calmed a bit I picked up my sucking again.

I did this over and over again. The taste just got better and better. Then he held my head while he pushed in further. I let my hands drop to the ground. Then I was choking as he filled my mouth with a salty yet sweet taste. I swallowed everything I could. To feel him pulse in my mouth was the ultimate feeling. I kept sucking and licking until he went soft and slipped out of my mouth.

He pulled up his boxers and jeans and helped me up off the ground. He kissed me passionately. Then took my hand and we slowly walked back to the house.

Ann and Miss Baxter had some lunch ready but I really don't remember what it was.

Miss Baxter kept staring at me, almost as if she knew what happened or something. She was a little quiet too. Ann was doing most of the talking. She loved that we looked like twins. Tony and I held hands almost the whole time, but it felt different somehow.

We got ready to go, Tony gave me a little kiss to say goodbye. Miss Baxter raised an eyebrow at that.

We agreed to meet up again next weekend but Miss Baxter said only if we don't have other plans. That confused me. What other plans could she have?

The ride back to the city was awkward to say the least. She hardly said a word.

Then she asked if I swallowed?

I was a bit surprised by her forwardness but said yes with embarrassment.

That just seemed to make her more angry. She called me a slut, and a whore. She told me she would teach me a lesson I'd never forget.

She was scaring me. I tried pleading with her but she would have none of it.

We got back to her condo and ran to the basement to get undressed.

She followed me saying if I wanted to be a slut then she would treat me like a slut.

I took my dress and shoes off but then she forced me down on the bed. She sat on top of my back and handcuffed my right hand first. I tried to get away but she held me down. Then the left hand was handcuffed to a post. She spun around and got both legs locked with ankle cuffs.

I was crying like crazy. Then she pulled a mask over my head. I couldn't see anything. I was still pleading with her but it seemed the more I pleaded the more I was restrained. She then forced a ball thing in my mouth and strapped it in place around my head.

Now all I could do was sob.

I couldn't hear anything. I didn't hear her go upstairs so I knew she was still here. We stayed like that for a long time.

Then I felt the butt plug being pulled out. A wet wipe cleaned the area.

Then I felt my ankles being freed. The ball in my mouth came off next and then the handcuffs. I took the mask off myself. She was sitting in the vanity.

I got out of the girls clothes and into my boy clothes. She handed me a wet nap to clean the make-up off my face. I left without saying a word to her.