Chapter 6

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On Friday night of the weekend before the end of the school year, Mom took a bunch of measurements of me. She said she was going to buy me an outfit, a brand new girls outfit, just one.

She said I would need to have something to wear when I got to Aunt Jill's. She explained it would be much easier to go clothes shopping all day with Aunt Jill and cousin Kelli if I already had an outfit of my own to wear instead of having to go as a guy.

I was afraid she was expecting me to go to the mall with her to shop for these clothes, but to my relief, she assured me that if I didn't want to go I didn't have to. There was one condition though. If I didn't go, that meant I wouldn't get any input into what she bought and I couldn't complain about it later.

She really wanted me to go and she explained that it could be discreet, no one else would know we were shopping for me.

I thought about it for all of half a second before I told her I'd pass on the offer to go and that she had a deal, I'd wear whatever she chose. I told her I trusted her decision.

Inside however, I feared I'd regret that decision later, but at the same time I knew going and risking being seen by someone from school had the potential to be much worse. Besides, if it was hideous, I'd only have to wear it one time.

Saturday morning, mom gave me another opportunity to change my mind and go with her, but I stuck to my decision. In my mind, the risks outweighed the reward.

She didn't say anything else about it, but I could tell she was disappointed when she left, which kinda made me feel bad for not going, but I just couldn't risk it.

I told myself I'd try it all on for her as soon as she got home. Hopefully that would make up for not going.

That afternoon, when mom returned from the mall she emptied the shopping bags on my bed and excitedly showed me everything she had bought.

There was a lace trimmed, tiny little black bra: she called it a starter bra, and a simple pair of plain white cotton panties. I tried to tell her they were way too small. I could tell just by looking at them.

She chuckled and assured me they would stretch a lot when I put them on and were supposed to fit snug. She said girls underwear was designed to disappear under your clothes and not be loose fitting like guys undies are.

Also in the pile of feminine things was a long, thin, ruffled bohemian skirt, and a matching blouse with cutouts at the shoulders.

Mom picked up the skirt and held it out so I could get a good look at it. At the same time I removed my t-shirt and began unbuckling my belt.

"What are you doing," she enquired.

"Well, I need to try it all on to make sure it fits, right?"

"You don't hav--, okay, sure, if you want to," Mom replied, a little too excitedly.

After first watching me struggle with the bra, mom finally helped me get it fastened. She then laughed when I got the boyshorts on.

At first I didn't understand what she was laughing about, but then I looked down and my face flushed. The snugness of the panties not only emphasized my bulge, I was about half erect.

Throughly embarrassed, I attempted to keep my manhood covered with my hands while mom held the skirt out for me to step into it.

With my nether regions now concealed by the busy pattern of the skirt, I was able to relax a little and looked at myself in the mirror.

To my surprise, everything fit perfectly and I had to admit the clothes were much better than what I had feared she might choose.

I asked her if I could wear the outfit for a while, I was starting to get excited and wanted get used to it, but she advised me to go ahead and remove it since dad would be home any minute. She reminded me that just because dad had agreed to this didn't mean he was ready to see it yet.

Once I had changed back into my boy clothes, Mom had me place my new outfit in a small overnight bag. She said I would have to put them on in the car, once we left the house headed to Aunt Jill's. That way I could arrive looking like a girl and not tip off any of Aunt Jill's neighbors.

These clothes were the only things I would be taking with me aside from one more bra, a pack of panties, the modest makeup kit I had been practicing with for the past several weeks and several of the teen girl magazines Mom had bought me, each with pages I had dog-eared for later; hairstyles, makeup techniques and clothes styles I wanted to discuss with cousin Kelli.

As I packed my new outfit I began to feel a nervous excitement that, up until now, I had not experienced in response to what I was about to do. I didn't know if it was from the unexpected arousal I had experienced seeing myself in the mirror dressed as a girl or what but I wasn't dreading it like I had been.

Then, at that moment the reality of my impending experience hit me full force and I couldn't believe in seven days I would be leaving my masculinity behind for the entire summer.

The entire summer!

That's when I was suddenly struck with fear and a darkness consumed my mind.

Oh, shit . . . I don't know if I can do this. Is it too late for me to back out?

The panic rose up inside me like bile, threatening to choke the words from my throat. My heart raced, my palms grew sweaty, and I felt like I couldn't breathe. I glanced around wildly.

My mind flashed back to the conversation I'd had with my parents. How they'd seemed so sure of themselves, so confident that this was the right thing for me. And yet, as I stood there in my room, surrounded by my old life, I felt anything but confident.

The panic continued to rise, threatening to consume me entirely. I took a deep breath, trying to calm myself down. I couldn't just back out now. Not after everything that had been done. But still, the fear was overwhelming.

I glanced around my room, searching for some sort of anchor, some reassurance that I could make it through this. My eyes landed on a small wooden box on my dresser. It was engraved with the initials "KW" - my late grandmother's. I'd found it when I was cleaning out her attic last year, and she had given it to me just before she passed away.

Inside the box were a few mementos from her life: a worn photo of her as a young girl, a locket with a picture of her parents, and a small, handwritten note. I'd read the note before, but now, feeling so lost and scared, I opened it and began to read it again.

Dear Kylie, it began, As you navigate through life you're going to go through tough times. Life can be hard, its not going to be all roses, and sometimes it'll feel like there's no way out. Just remember, you are stronger than you know. You have the courage and resilience within you to face any obstacle and  overcome anything.

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