How I was Trained Pt. 09

How I was trained

Amy takes me shopping and we both had fun.

Part 9

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I love my new life. It doesn't feel like I'm pretending anymore. When I was in boy mode, I was always trying to fit in with friends and everyone really. Constantly trying to be like my friends.

With Amy it's way different. Yeah sometimes she might push me in a certain direction. Like the other day, I wanted to suntan on the back deck with nothing on. Even with it being late October, it was still quite hot. She said I should wear a two piece bikini. I didn't want to wear anything but she insisted. She handed me probably the skimpiest two piece I've ever seen, so now I have the sexiest little tan lines in the whole country. She was right again, as usual.

Time seemed to fly by. Before I knew it, Halloween was coming up.

Amy seemed to be extra excited about it but wouldn't say why. All she would say is this year is gonna be the best Halloween ever.

My breasts kept growing so much that Amy finally said we need to go shopping for new bras. That could only mean one thing. Shopping trip into the city.

The next morning we got ready to go to the city.

As usual Amy picked out what I'd be wearing.

She surprised me today. No bra! She said they don't fit anyway so why wear one.

I still wore black panties and pantyhose. White heels and a white tight fitting dress with a slight plunging neckline. My nipples showed big time but I love it. I also wore a small gold necklace with a cross pendant on it. My breasts looked amazing to me with the cross nestled between them. She told me I could have it if I wanted it. I gave her a big hug to say thank you. It really made my breasts stand out.

The drive to the city is usually boring, not this time. She kept asking me what kind of undergarments I preferred to wear.

Honestly I thought she was testing me. When she asked me point blank, "do you like to dress classy or slutty?" I had to really think about it.

"I guess I like both," I told her. "It depends on the situation."

"So give me an example of when you want to be classy?" Amy asks.

I blurt out, "Church, or going to dinner with friends. You know, when it's required."

"And slutty is when the clothes are coming off before the end of the night," I said but I didn't blush because I knew she would say 'awe look at you, you're so adorable'.

"She looked at me with a huge smile, "you really are a slut. Aren't you." She says! "What about casual wear?"

Now I know she's testing me. I've never seen her wear casual clothes, ever!

"Seriously," I asked.

"Yeah, seriously." she responds.

"Well I prefer to dress up, that's why I agreed to be trained to begin with," I said.

She just smiled.

When we parked the car and got out, we both stretched our arms into the air. My tight dress squeezed my breasts together even tighter, that's when Amy noticed a few teenage boys checking me out.

She smiles, yelling, "She's single if anyones interested!"

I blushed almost immediately but it also turned me on knowing the young men's cocks were probably hard as iron.

Confidentiality we walked arm in arm into the mall leaving the boys there drooling.

We probably went to every store in the mall that day.

The first store was a lingerie shop. A very pretty young lady with sizable breasts herself, maybe twenty-five years old, asked if she could help us. Amy has that look again. I immediately looked around for some hunky guy she was gonna try and embarrass me with but I only saw the three of us.

" Why yes," Amy said. "My daughter needs an accurate measurement for some new bras." knowing full well I'm still growing.

The young woman said yes of course. Right this way as she pointed me towards the changing rooms

I know amys testing me somehow but for the life of me I couldn't figure out how.

The young woman and I step into a large changing room. She asks me what size I normally wear. I told her I wasn't sure so she grabbed a paper measuring tape and asked me to take my dress off.

Now I knew exactly why Amy had that look she got. I suddenly felt embarrassed trying to come up with another way to only disrobe my top half

I tried pulling my arms in but the top was too tight. She stood there patiently watching me. I'm sure she was thinking what the hell is she doing.

"Is there a problem with taking your dress off? I'll only need it off for a few seconds or so." She says.

Feeling defeated I say, "No. I just..., nevermind and I pulled my dress off over my head.

As my panties came into her view I heard her gasp rather loudly. I kept pulling the dress off. When I saw the look on her face I knew damn well she knew I was born a male.

She was still professional all though now she was somewhat red faced and took the measurements under my breasts and over my nipples.

She excused herself to go get a few bra choices.

I sat down on the little bench thinking well I don't think I could be more embarrassed than I was at that moment, boy was I wrong.

Amy and the young woman came in together, each had an assortment of bras for me to try on.

The first few were choices of the young ladies. They fit nicely and fully covered and supported my breasts very well but Amy said, "you know I think those are just too casual," a grin pointed my way.

I could literally feel my face turn red.

The first bra was a satin red quarter cup underwire bra. It literally made my breasts look twice as big as they were and showed three quarters of my breast including all of my nipples.

"Ah yes, we'll need five please, two in red, two in pink and a purple one please," Amy proudly orders.

Somewhat red faced the lady says, "Perfect. No problem." as she writes the order on a piece of paper.

Next she had me try on a pink half cup underwire bra.

I smiled, saying, "well at least this one covers more than the last one."

Amy raised an eyebrow at me saying, "You're the one that said you didn't want casual my girl."

The lady laughed out loud just for a second.

Amy told the girl we would take five in pink, purple, red, blue and yellow.

Again she wrote the order on the same paper with a smile.

Next bra was a see thru mesh bra. It also had underwires in it. I liked this one for some reason.

"I don't know," Amy says, do you think it's too casual?

I turned towards the mirror and clearly saw my entire breasts through the garment. "You think this is casual?" I questioned

I think it will let her breasts breathe a lot better, well er.. Better than some that is." the young lady says.

Amy aggref and ordered five of this one too in the same colors.

"Yes ma'am," the lady said as she added to her list with an even bigger smile. "I think you should wear the bright red satin quarter-cup bra under your pretty dress today. You really do look hot in it, she suggests.

Amy smiled, saying, "what an excellent idea, hear Lisa!" she hands me the bra saying put this on my girl! Emphasis on girl!"

I was thinking we were done but then the woman suggested I should get panties to match all my new bras.

Amy had a mischievous smile on her face instantly saying, "You must have read my mind."

The two women ran off to pick out panties and tell me to stay put. Amy told me as she left the changing room to have the panties I was wearing off by the time they got back.

I put the bra on as Amy told me and removed my panties too. I sat there looking at the chastity cage thinking maybe Amy's right, I don't need this cage anymore.

It took the women about ten minutes to pick out an assortment of panties for me.

Of course Amy had me try on crotchless panties. The young clerk was having a shit ton of fun at my expense and of course I couldn't do anything about it because Amy was having just as much fun.

The young clerk held the panties legs open and had me step into them, she pulled them up as far as she could then I took over.

She patted my chastity cage saying, "I simply must get one of these for my boyfriend."

Amy spoke up saying, "Keep in mind, sometimes they don't want out of them so make sure you have a stud handy."

They both laughed.

Amy introduced herself and I and they exchanged phone numbers.

Amy paid the bill and we left.

I swear, every warm blooded guy in the mall was staring at my tits the whole time I was there after we left the store. Of course my nipples were hard and my bright red bra was extremely visible in the white tight fitting dress.

To be honest I really loved the attention I was getting and I think Amy liked it too.

We bought a whole bunch of new undergarments, dresses, skirts and various tops and went back to the car in the parking lot.

I swear there were a lot more boys and it even looked like maybe a few dads were on the edge of the parking lot where the boys were before.

Everyone of the we're drooling and their eyes didn't blink even once as we loaded our purchases into the car.

Amy looked hot as fuck in her new tight black leather mini skirt and white satin blouse she had tied just under her beautiful breasts. Of course she had the top three buttons und done, showing a lot more skin then I did.

I wore a new red short sleeved cut top that showed my entire belly and my new belly button piercing and a tight fitting pink mini skirt.

We left the boys in puddles of drool, then went back to the farm for the night.

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Thank you for reading.