How I was Trained Pt. 05

How I was trained

My first anal

part 5

======================

When I got home I went upstairs to the bathroom to have a shower. While I was there I noticed my pink fingernails. I freaked big time. I didn't know how to get the nail polish off. I finished in the shower and quickly went to bed. I kept my hands under the blanket and pretended to be asleep.

My mom peaked in my room a short time later and closed my door again.

The next morning I had forgotten about my nails. I was downstairs eating breakfast when my mom stopped dead in her tracks.

With a mouthful I asked "What's wrong."

She laughed saying, "It's a nice color, but I'm not sure it is your color?"

Realizing my mistake I hid my hands quickly.

She laughed again asking, "Did Miss Baxter paint them?"

I turned red with embarrassment.

"Can I help to get rid of them?" mom asked.

"Yeah, can you do that?"

"Sure hunny, "she said as she retrieved a bottle of acetone and removed the nail polish.

"You should cut your nails before you go." But I would have been late. They weren't that long so I didn't cut them.

The whole week I thought about what could have made her so mad. I went over everything she ever said to me or asked me.

It sounded like she wanted me to be with boys but now I wasn't sure. I love dressing as a girl and girls have sex with boys! So I really was confused. I really like Tony! He treats me well and his cock is so delicious. It bugged me a lot.

I had to walk by her condo twice a day for school and everytime I did her curtains were closed.

Thursday was a half day so when I walked by I noticed her door was open. I stood there thinking I should go talk to her. I thought how mad she was and it upset me more. I was about to go knock on her door when Mike came out.

I thought well maybe she doesn't want to train me anymore. I sat on the curb and thought it through again. When I looked up again her door and curtains were closed again so I went home.

Friday I went to school but I avoided her place. I didn't want to wonder all day anymore. I did the same on my way home.

Summer break was only a week away. Well four more days actually. We were off at noon on Thursday. I was in a happy go lucky mood all day. I didn't think anything could ruin it.

When I got home, Miss Baxter was talking with my mom. Mom called me into the living room where they were and asked me," Do you want to sleep over again?" This way we could leave early for church again.

I gotta say I was quite surprised she still wanted to do that.

"I thought you had other plans?" I asked Miss Baxter.

"Nope! They fell through. So if that's what you want then let's do it she says."

"I guess so, but I thought you didn't, I mean, I didn't think you wanted to do that?"

She just smiled and asked again. "If you want to go then be at my place tomorrow night, say eight o'clock"

"Saturday night?" I said.

"Yes, I have a prior engagement during the day, so eight o'clock?"

"Okay," I sheepishly responded.

Miss Baxter got up and left. I went upstairs and laid in my bed.

What is she up to I thought! Are we gonna go to church and then come straight back home? At least I'll get to see Tony at church I thought.

The next day I woke up early without my alarm. What am I gonna do all day? I thought to myself.

I decided to go see my friends. I found them at the park as usual. We decided to go for a bike ride in the river valley. We were all having a blast then we went up this trail I'd never been on before.

Then I saw Miss Baxter sitting on her back step.

It turns out it goes right past her back door. There is a field and some trees that separates the path from her place, so I stopped. I told the guys, "I'll catch up later," and they all kept going.

I hid in the trees and watched her for a while. I don't know why, but I thought if I can see her then anyone could have seen us the other day. It kinda worried and excited me at the same time.

Eventually she went inside and I left. I couldn't find my friends so I just rode my bike in the back alley.

She saw me and waved me over to her.

"Hey Miss Baxter, how ya doing today?"

"I'm good, Lisa!"

My eyes got really big.

"Don't call me that when I'm not dressed," I told her.

"Isn't that rich? You give a guy head and don't want to be called a girl's name."

Thank god no one was watching.

"What are you doing?" I ask.

"Just pointing out the obvious sissy boy."

I got mad at her saying," you'd better stop that or I'm...,"

She stood up fast yelling, "OR WHAT? ARE YOU GONNA GET MAD?"

I was really shocked to say the least. I don't like seeing her this angry so I stepped back a bit.

"I OWN YOU! YOU DO AS I SAY! GOT IT!"

"Yes ma'am," is all I said.

She sat back down, flipping her hair away from her face saying, "good. Now that we have that straight, I'll see you in a few hours for your next lesson. I'm sure you'll hate this one but oh well."

"You can go now Lisa." She said as she looked away from me.

I went home to my room.

A little while later my mom woke me up saying, "if I was going to Miss Baxters, I'd better eat and get going."

Looking at my alarm clock, it was already 6:30.

"I guess so," I say to my mom.

"What's wrong hunny?" She obviously saw I was bothered.

"Did you ever do something that felt so right? Then find out it wasn't."

"All the time honey. That's what growing up is all about. You make mistakes and you learn from them! Then you move on." mom said.

"Even if it felt so good? It didn't feel like a mistake! I mean I know some people say it's wrong but it sure didn't feel wrong!"

"Is this about Miss Baxter?"

"No, not her, But she's kinda really mad at me and I don't know how to fix it. I really like Miss Baxter. She's great and all but I wish she could see it the way I do."

"Then explain it to her in your words. Use your heart and I'm sure she will understand. Now let's go eat." she said.

"Okay mom. I'll be right down." She went downstairs and I went to the bathroom. I was pretty much used to sitting to pee now so it was quick and easy now.

When I got to the kitchen table, dad was already done with dinner, he was in the living room smoking. I hate the smell of cigarettes.

I sat down and ate dinner with my mom and brother. Mom asked? "Why do you like church all of a sudden?"

I told her, "I like spending time with Miss Baxter and she likes going to church so it just works I guess."

My brother laughed saying you got a girlfriend. He kept bugging me by singing some stupid song about kissing and babies or something.

I got angry and was about to punch him when my dad yelled at him, "Shut your trap or I'll shut it for ya."

We all shut up for a bit.

I finished eating and had to wash the dishes before I left, so I got to work. As soon as I was done I told my mom, "I'd better get going." She gave me a kiss and told me, "Behave yourself and mind Miss Baxter."

"Yes mom. I promise," and out the door I went with my duffle bag of clothes.

I got to Miss Baxters a little early. She was sitting on her front step. I sat beside her.

"I need you to understand something," she said.

"I do what I do for a reason! It's not all about you here. I get something from what I teach you. It's hard to explain but I need to teach boys like you, to train you my way. So when you go do things that are ahead of my schedule, it infuriates me to no end."

I wasn't exactly following what she was getting at. The confused look on my face told her that.

"You sucked Tony's dick! I wasn't ready for you to do that yet."

"Obviously you're more gay than I thought, but I'll figure something out."

I just stared at the ground.

"Let's go inside and talk, okay?"

"Okay." I said.

We talked for a few hours.

I told her everything about what happened.

How I felt.

How he tasted.

How he smelled.

How big he was.

How I didn't feel too tight in my cage.

How nothing else mattered.

How his jizz tasted.

Then she asked me what I thought he would do to me if he found out I was a boy.

My stomach sank. I hadn't thought about that at all.

"That's part of the reason I was so angry at you! Another reason was I want to be the one that teaches you everything you'll ever need to know about sex, whether it's with a woman or a man."

"Do you remember what we did together last weekend?"

"Yeah. I remember. It was great."

"It was great for me too, you know! Then you dropped me as soon as you saw Tony's cock.

I looked down in shame. "I didn't. You know I didn't mean..,"

"I know, but now you do. So what's next?" She asks.

I shrugged my shoulders saying, "I didn't know."

"Are you gonna suck Tony's cock if he wants you to again?"

"I want to but what do you think he'd do if he found out I'm not a girl?"

"Good question. He may be okay with it, then again he might not. If he's not then he might get really violent with you."

"How do I find out without? you know, Getting beat up."

"You'll have to ask him in a sneaky way. You'll have to trick him into wanting to be with a sissy boy like you."

"I might have an idea but it's gonna take some time to set up. For now, try not to do anything sexual with Tony! Let him do the chasing and you do the denying." she told me.

We went inside, she made me tea and told me to drink up.

Strange but she didn't have any.

"It's getting late, so we better get to bed, don't you think?" she suggested.

"Yes ma'am." We went up to her room. We took our clothes off. Of course I was staring at her the whole time.

She handed me a little nightgown to wear and she put one on too.

We then got under the covers and she snuggled up to me.

The cage was mighty tight let me tell ya.

The alarm woke us up at five am.

I still felt so tired but I followed Miss Baxter's instructions and got in the shower.

When I got out I went to the basement. She had everything picked out for me. She told me to get dressed and make sure I put my butt plug in. She went up to shower.

Today I was wearing a white lingerie set. Push up bra. String panties, later I found out they were called G-string but I didn't see where the G was. Oh well. Stockings and garter belt. I really like this more than pantyhose. White heels and a white short tight dress that was like a turtle neck with a bow at the neck. It fit very tight in the chest but loosened at the waste into a pleated bottom.

The long blond wig always makes me feel more girly when it's in place.

Miss Baxter came down and did my make-up and painted my fingernails pink again then handed me a little white purse with lipstick, lube and a couple condoms.

She told me, "This is just in case but you can't show him your front. You'll have to bend over if he insists."

She then asked me to show her my plug so I bent over.

"Good girl." She said with a big smile. Then she bent over to show me she had one in too.

Seeing she had one in her ass made me so happy!

We got in the car and started driving.

She then asked, "Why didn't your nails have any nail polish on them?"

"Funny story, I explained that my mom saw them the next morning. The way she acted made me so embarrassed."

"She took the polish off and told me I needed to cut them but I didn't."

She laughed, then asked "why was I so embarrassed.

"Well I'm a boy, I mean I wasn't..,"

She laughed again.

"I see we still have work to do with you, my little Lisa girl."

I commented that, "we'll be early at this rate."

She smiled, then a few minutes later she pulled into a parking lot. It looked like a restaurant. We got out and went inside and sat in a booth. A guy asked," what would you ladies like?"

A short while later we were eating breakfast. Miss Baxter was flirting with the guy a lot. Then she told me," you stay here and pay attention, this is my next lesson."

She went into the back. She was gone for a while. I was wondering what she was doing. I watched out the window.

Then she sat beside me. She grabbed my face and kissed me. She forced her tongue into my mouth then pushed a liquid into my mouth. I recognized the taste. It was jizz. We shared it back and forth then I swallowed it. She pulled away saying," Your such a very good girl!"

Then she moved to the other side of the booth. I looked over to the door to the back and the guy was standing there with a huge smile on his face.

I looked back at Miss Baxter as I raised an eyebrow.

She laughed as she told me, "you weren't the only slut here!"

We got up and left without paying the bill.

We were just leaving as I asked, "do you know him?

"Nope. I never met him in my life."

"But, you sucked his cock?"

"Sure did! Wanna know what the difference is between what you did to Tony and what I just did?"

"There was no difference, I said."

She looked at me with a weird look. "Of course there is! I shared the reward with my best girl."

I just smiled thinking does she want me to share Tony with her?

We got to church a bit early so we walked around the back. There were a bunch of benches set up so we sat at one. Miss Baxter instructed me to sit up straight and push my chest out. She showed me how and even though it kinda hurt my back I did it.

She told me, "You need to walk the same way."

We practiced back there until the church opened.

We sat in the same place, even though there were lots of other places to choose from. Again the plug made me fidget as it was being pushed in further. Miss Baxter held my hand again.

Tony and Ann finally got there. Tony sat beside me and Ann sat on the outside seat. Tony quickly took my hand. I was sitting up straight and pushing my chest out just like Miss Baxter showed me.

I know this got Tony's attention. He kept stealing looks at my chest.

After church we went to Tony's farm but when we got there Miss Baxter told me to come inside as it was a bit hot today.

Reluctantly I said, "yes ma'am." We went inside and Miss Baxter sat on the loveseat leaving the two armchairs and one spot beside her.

Miss Baxter asks, "Tony, would you sit beside me please."

I was so angry, it felt like she was trying to steal him away or something.

Ann asked me, "would you like to help me with lunch?" I really didn't want to leave Tony with Miss Baxter but I really didn't have much choice.

It only took about fifteen minutes or so to make lunch. We called Tony and Miss Baxter to the dining table to eat.

It took a bit for them to come but when they did, Miss Baxter sat beside me so Tony sat beside his mom.

We ate lunch and made idle chit chat then Tony got up saying he had work to do. I stood up saying, "I'll help."

He smiled and said," No, your mom's right! It's pretty hot outside and you didn't have a hat."

He then put a cowboy hat on, tipped it at me and said, "I'll see you next week." He went out the door.

I felt so rejected, so mad. I didn't know what to do.

Ann and Miss Baxter talked about everything under the Sun it seemed. I stopped listening quite a while earlier. All I could think about was Tony.

Ann excused herself to go to the bathroom and Miss Baxter said, "I know you're mad! You have no reason to be. You know I couldn't let you be alone with him! Not yet anyway. I told him he's a nice boy but you're a bit naive and to be patient with you."

A little while later we left without seeing Tony again.

The ride back to the city was very quiet.

When we got to her condo I went straight to the basement and sat on the bed. She went upstairs I think.

A few minutes later she came downstairs. She sat on the bed and said, "I know you're upset but you have to trust me here. I know how you feel. You feel let down."

A tear rolled down my cheek as I told her, "I didn't want to share Tony with her."

"Sweetheart, I don't want Tony! I want to protect you. Have you ever had sex with a boy before?"

"No, no I haven't." I shyly said while tears rolled down my face.

"It can be beautiful and it can really hurt too. Do you trust me?" Miss Baxter asks.

"Yeah. I trust you." I sobbed.

"Good." She hugged me for a bit as I calmed down.

"Better." She asks.

"Yeah."

"Good, then come to my room. I want to show you something.

I followed her to her room.

When we got there, Mike was on her bed.

He didn't say anything, he just smiled at me.

"Mike has agreed to help you with your first time if you want. I'll supervise to make sure he does it right but you have to want this. Do you want this?" She asks me.

Mike was naked. His cock was in plain sight. He wasn't as big as Tony but he wasn't hard yet either.

Miss Baxter sat in a chair off to the far side of the bed. She watched to see what was gonna happen next.

Mike asked, " Do you want to sit down and think about it?

Without thinking I just walked to the bed and sat down.

You could have heard a pin drop while I thought about what Miss Baxter wanted me to do.

I felt ashamed and embarrassed but my little penis was straining really hard in the cage.

I thought back to what I did to Tony at the farm. My cage seemed to get tighter. I thought about what Miss Baxter did to the guy she didn't even know. It got even tighter.

Miss Baxter came and sat beside me. She put an arm around me and hugged me tight.

"See what I mean? It's not all fun and games! There's feelings to deal with too."

"It hurts, "I whispered to her.

"I know sweetheart, I know."

"No, my cage hurts." I whispered.

"Oh," she says. "You know what that means, right?" As her voice rises.

Shaking my head No, I said, "I don't think so." Obviously confused.

"It means you're excited about what Mike can show you." She said excitedly.

I looked up to her, she smiled and told me. "Go enjoy yourself and Mike but remember he has feelings too."

I smiled as she wiped my tears away.

We stood up and she helped me take my dress and panties off. When I looked at Mike again his cock was hard.

"You have a very cute cage, how long have you been wearing it?" Mike asks

I told him, "a couple of weeks now."

Miss Baxter took her dress off too. Then she went and sat in the chair again.

"Mike, lay flat on your back sweetheart." Miss Baxter told him

"Now Lisa, climb on the bed at his feet and slowly crawl up to his cock."

"Kiss his thighs as you slowly work my way further up. Sit between his legs and use your fingernails to lightly tickle his thighs and stomach but don't touch his cock just yet." she explained.

"Move your head closer to his cock, but don't touch it. Breath on it lightly." As I did his cock twitched.

"Now kiss each side of his groin. Taste him. Let him feel your hunger. Feel his excitement as you move closer and closer."

I couldn't take it anymore so I licked at his balls.

Miss Baxter said, "Yes that's it darling." She sounded excited for me. "Enjoy him, "then she went quiet.

I licked at his balls for a bit, savoring the taste and smell. Then I licked up the base. I'd stop from time to time to kiss and taste him some more.

By the time I got to the top his cock was glistening in my saliva. Clear liquid was seeping from the small slit at the head of his cock onto his belly. I flicked my tongue at the top but didn't bring it in my mouth just yet. I looked up at him. We made eye contact and then I slowly brought his nectar into my mouth.

He tasted sweet, very sweet. He kinda gasped as I moaned. I licked the little puddle on his belly next.

"Suck my cock baby." He pleaded.

My chin was pushing down on his cock as I slid down until the tip was in my mouth.

I could hear Miss Baxter moaning in the chair and Mike let out a long sigh.

Mike took sharp breaths as I sucked the tip and was rewarded with more sweet nectar.

I swirled his sweet nectar around his cock head with my exploring tongue then slowly slid my mouth down. I kept going until I felt his cock head at my throat. Then came back up.