How I was Trained Pt. 07

Story Info
I had to find out if Tony would like me. Amy has some fun.
2.6k words
4.65
6.1k
10
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

How I was trained

I tell Tony what I am & Amy becomes my mistress.

Part 7

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

We slept in the next morning but at least we didn't have to drive for over an hour to get to church.

Amy picked out our clothes as usual.

Today I was wearing a pink lingerie set but with a corset bra combo. I love the tight feeling. Stockings, garter belt and cute g-string panties followed. I wore pink open toe heels and a yellow sun dress. Amy handed me my little white purse and said I should never forget this.

Amy looked beautiful as always in a blue sun dress and heels.

We got to church just in time. I sat next to Tony and Amy sat beside me.

Tony and I held hands almost as soon as I sat down.

He said Amy and I both looked beautiful then the sermon started.

When church was done Amy invited Tony and Ann back to her place, I guess our place now. They accepted and followed us there.

I hadn't actually gotten a good look at the surroundings so when we got there I asked if Tony and I could go for a walk.

Amy handed me my purse and told me to be careful. It's been awhile since she was here last. I changed into running shoes and put a big pink sun hat on.

Tony and I walked around the place and found a small creek with some trees covering some of it. We went down and sat on a fallen tree in the shade.

I had to find out if Tony would accept me as a crossdressing sissy boy.

"So Tony, tell me. Do you like all kinds of people?"

"Sure, why not?" he replied.

"Oh I'm just asking," I say inquisitively.

"Do you like boys as much as girls?" I ask.

He quickly asks, "What kind of question is that?"

Defensively I say, "Well I like boys and girls."

Tony sounded confident saying, "Really, what do you know about girls?

"Oh I know quite a bit about girls. I like how soft they are, how nice they smell and taste and how they make me feel inside." I say.

"Yeah, I see what you mean," he says. "Sounds like you're a bit of a lesbian! "

With a sly grin I say, "Maybe, But I also like boys because they are strong and powerful but they can be gentle and soft too. Some guys like to take control. And they almost always smell great."

"Now you sound like a normal girl." he says with a grin of his own.

"Oh I'm not a normal girl Tony! I'm far from it."

Confused, he asks, "What does that mean?"

"Well, tell me something. Would you ever kiss a boy?" I Inquire.

Disgusted, he says, "No. That's a stupid question."

Somewhat angry, I ask, "Why not?" knowing the answer already.

"Because that's gay." he says."

"So what!" I say as I pump my chest out just a little.

"Would you ever kiss a girl?" I asked.

"Yes? Of course, I kissed you didn't I." he says confidently.

Thinking back to that beautiful day I sigh, "Yes you sure did and I kissed you back."

"Yeah that was nice," he says then asks, "have you ever kissed a girl?"

Looking up and twisting my right foot on my toe I reminisce, "oh yes, I definitely have kissed a girl."

He looked a bit surprised but still looked like he was interested.

"Haven't you ever been in the locker room at school when you went to public school and wondered about what the guys' bodies looked like and how they felt?" I asked.

"Yeah I guess so but not in a gay way." he says.

Pressing for a better answer I say, "What's a gay way? It sounds like your hung up about gays in general."

"No, I don't care if anyone is gay or not. I just don't think I could do something with a guy!" he tells me as his voice raises a bit.

"What if you didn't know?" I press.

"I would know, trust me." he says with confidence.

Pressing still I ask, "Are you sure?"

With a bit of attitude he says, "Yeah, I'm sure."

Somewhat confident myself I say, "Because I have a secret to tell you!"

He just looked at me with a puzzled look. "What are you saying, you're a guy?"

"What do you think?" I ask hoping he doesn't get violent with me.

He looked me in the eyes confidently saying, "You sure as hell don't look like any guy I've ever seen."

"Well I guess you'll never know then will you." I whimper.

Realizing I was upset but still firm in his conviction he asks, "What does that mean?"

"It means if you can't accept me for who I am then you'll never accept me." I told him as I started to cry.

"Listen, I like you a lot and not just because of that time at my place. I just want things to stay easy between us." he says.

"Okay, no problem," I said angrily. "Easy it is and I stomped off for the house.

He was trying to keep up but I was walking very fast. He grabbed me by the arm saying, "will you listen for a goddamn minute already."

I stopped and crossed my arms saying, "go-ahead."

"What's got into you? You start this crazy talk about liking boys and girls alike and hey that's fine but what's that got to do you me?"

"You can't be that blind, I'm sure," I yelled, then turned and went back towards the creek by mistake but I was so upset I didn't care. He caught up to me again grabbing my arm again.

This time I hit him on the chest. He hugged me and held me tight.

I sobbed into his chest as I told him, "I really like you a lot more than I should Tony, but we can't do this because you would never approve."

He told me, "all I could think about was what I made him feel at his place. No girl had ever made him feel that way."

I broke away from him screaming, "a girl didn't make you feel that way, and the fact that you liked it so much must mean you're gay." Then I ran home.

He just stood there shocked I assumed, but now he knew.

I ran inside and up to the bedroom. A little while later I heard their car leaving.

Amy came upstairs and put her hand on my back as I cried into the pillow.

"I guess it didn't go that well with Tony," she stated.

I got up and hugged her, she held me tight and told me it would be okay.

I told her everything. She smiled and told me to give him some time. She thought he might just change his mind. We would wait and see. She held me for a while longer as I calmed down.

We had a bite to eat over some tea of course. By the time we were done I felt a lot better.

"Do you think I can call you Amy from now on?" I asked.

She smiled saying, "of course Lisa."

I smiled when she called me that.

"How about we go look around town to see what's changed since I lived here all those years ago," she suggested, so we put our heels on and headed for town.

I was listening to the sound of our heels on the road, the feel of the slight breeze on my skin and the heat of the sun on my face. Not really paying attention to Amy as we walked. She stopped but I hadn't noticed, then she said, "hey you!"

I stopped, snapping back to reality as I looked back saying, "what?"

"Where are you?" she asked.

"I'm here. With you." I said with a smile.

Amy smiled, "No you are not! I don't know where you were but it certainly wasn't with me."

"I'm sorry," I said. "It's just the sound of our heels on the road, the feeling of being me out in the sun. I just love being Lisa."

She smiled at me and said, "WOW, you surprise me every single day."

"How so," I asked.

"Only a woman would pay attention to the sound of heels on the road Lisa."

I laughed and said, "well I have a great teacher."

"Thanks kiddo, I really appreciate that." she smiles as she takes my hand.

We walked hand in hand into town. It wasn't a big town that's for sure but she pointed out every building and told me who used to own it and where her boyfriends lived and even her girlfriends.

She showed me where she went to school and where she got her first kiss.

We had a great day together.

"So how do you feel about Jake and Adam," Amy asks as we start to walk back home.

I confessed, "I like Jake but Adam scars me. If Jake hadn't of been there I think Adam would have raped me."

"I think you're right about that but he had been drinking too so maybe to give him some slack." she tried to explain.

"I guess I will but only if you or Jake are there," I insisted.

"Okay sweetie," she said.

When we got back Amy showed me the basement. It was close to the same as in the city except it was bigger and had a lot more things down there.

She had what's called the cross which looked like a big X with hand and leg restraints.

She had a padded bench that had restraints too.

She had something called the stocks where you get your head and hands locked in it.

"Oh I like the stocks." I confessed to Amy.

She asked, "Do you want to try them?"

"Sure do," I said. She lifted the latch and raised the top up. She had me put my head in and my hand on each side. Then she closed it and latched it tight. I pulled my hands out rather easily.

She laughed, "You're quite an escape artist, aren't you."

I laughed as I said, "Even Houdini had a wife."

She had me put my hands back then put handcuffs on me with a long chain. "I'm stuck now," I said.

"Oh that you are my girl, let's see your Houdini get out of this. You're not going anywhere now."

I could hear her doing something behind me but I couldn't see.

"You know Lisa, you have fucked me with your pathetic little girl penis and I think it's time I fucked you with my not so pathetic toy! What do you think?"

Smiling, I said, "whatever you like."

I felt her hit my bum with something that made me jump. More so because I wasn't expecting it.

She lifted my dress up and hit my bare bum the second time.

I yelped when she did as it stung.

"Down here my pretty you will call me mistress, do you understand." her demeanor changed to a much more dominant one.

"Yes mistress," was my quick response.

"Very good. Now let's see what we have here."

She pulled my g-string panties down. She gasped as she asked, "where exactly is your plug young lady?

I could tell she was not pleased and stumbled with my words to tell her, "I forgot it." I have to admit, I actually sounded quite girly.

She hit my bum with something saying, "You mustn't ever forget it." She hit me two more times, "do you understand me? " she yelled.

Yelping in pain I cry out, "Yes mistress, yes I understand. Please don't hit me again!

She caressed my bum gently telling me, "my girl has a very nice ass, you know that?"

She kissed my smooth hairless stinging ass cheek as she played with my tiny balls. The cage got a little tighter but not too bad really. She probed my budding hole with her tongue and got me good and wet. I could hear her moaning as I moaned with her, then she pulled away leaving me yearning for more.

I felt cold liquid dripping on my backside.

"Relax my girl, I'm gonna stretch that tight little ass of yours now."

I didn't say anything.

I felt something hard pressing at my ass, she slowly worked it past my sphincter, once it was in, she slowly pushed it in deeper and deeper.

It wasn't very big but it hurt a little all the same.

She slowly worked it in and out of my ass saying I was such a good girl.

A short time later she pulled it out. It was replaced with a bigger one and she held my hips as she worked whatever it was in and out again.

She asked, "Can you feel it my girl?"

"Oh yes mistress, it feels wonderful." I blissfully acknowledged.

"Is it big enough for my sissy girl's pussy?"

I laughed at her calling my ass a sissy pussy but she must have thought I was laughing at the size because she pulled it out fast which hurt a bit.

Soon something much bigger was being worked into my backside.

Once she got the head in I moaned loudly.

"Is that better my little sissy slut?" She sounded a lot more confident.

"Oh god yeah mistress."

"Oh I like the sound of that baby girl." she whispers.

She took her time to slowly work it in and fucked me nice and slow.

"I own you now Lisa, you're all mine to do with as I please."

She fucked my ass a bit harder with every sentence she spoke. "You will do whatever I tell you whenever, wherever and with whomever I say. Do you understand me?"

Hearing this along with the hard sissy pussy stretching I was getting, I simply agreed.

She slapped my ass hard as she thrust in deep asking "what did you say."

Snapping back to reality I stuttered the words, "yes ma'am ah mistress."

She laughed saying, "Your so fucking adorable Lisa!

I just smiled, as I moaned, "thank you mistress."

She only stopped when she saw the puddle on the floor from the steady dripping of my caged little penis.

She unlocked the stocks letting me go and told me to lick up my mess off the floor.

I got on my hands and knees and licked it all up.

When I was done she ordered me, "Eat my pussy baby while you stroke my toy cock."

I love eating her pussy so I jumped at the opportunity.

The toy was a big bright red strapon dildo. So I stroked her as if she had a big huge cock as I ate her pussy.

She was soaking wet before I got down there. She held my head tight almost the second I got down there and flooded my face. I licked up what I could but there was so much.

She pulled me up to her and we kissed.

We cleaned up and put everything away. "I think we should go rest outside, what do you say Lisa?" Amy asked.

Most certainly mistress. I said back to her trying to sound like Sherlock Holmes.

We went upstairs and out to the deck. We sat there in the shade and just enjoyed each other's company. Then we made dinner and tea, ate and went to bed.

She had me wear a sexy little nightie and she wore one too.

She played with my chest, more so my nipples saying, "They were coming along nicely, don't you think?"

I had a pretty good idea what she was talking about but wondered how at the same time so I just smiled as I went to sleep.

Please comment as that's how I'll know if i should continue.

Thanks for reading my stories.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
13 Comments
AnonymousAnonymous6 months ago

I love Amy’s turn to the dominant side! Lisa is really getting an education!

AnonymousAnonymous10 months ago

AWESOME, THEY HAVE ALL BEEN AWESOME

AnonymousAnonymous11 months ago

Your pacing is excellent both in the way Lisa is being brought along mentally and physically. It’s so much fun to see how they each think. I hope you continue since I can’t wait to see what happens.

AnonymousAnonymous11 months ago

This is awesome more pls

AnonymousAnonymous11 months ago

Does the last paragraph about her chest "coming along nicely" mean she has her on hormones?

Show More
Share this Story

Similar Stories

Pleasing Mr. Wilson A summer job at the cottage leads to unexpected duties.in Transgender & Crossdressers
Eric or Erica? Pt. 01 Eric is saved from near death but his rescuers are different.in Transgender & Crossdressers
Fishnets / French Maid He wears his ex-girlfriend's lingerie - accidentally fucked.in Transgender & Crossdressers
My White Boy Sissy Pt. 01 Black football star makes white boy nerd his sissy bitch.in Gay Male
The Man That Converted Me A young man is snowed in & turned out on a mountain getaway.in Transgender & Crossdressers
More Stories