The next couple weeks leading up to the book report were pretty normal, aside from my new wardrobe options. As the day I would make my debut as Annie Oakley at school drew nearer, I started to anticipate the event and harbored a mix of anxiety, excitement, and hope that my decision to go “all-in” would be well received. As I finished typing up my report, I had a little bit of trouble concentrating as I thought about all of this, but ultimately buckled down and got it done.

Mom had me practice my presentation with her, and even gave me a few pointers.

The night before, Mom had me set my alarm for 5:30AM, just like my dream! I would need to start getting ready a full hour earlier in anticipation of the much more elaborate process of dressing in girl mode, versus my usual morning routine of jumping out of bed, brushing my teeth, showering, and throwing on whatever outfit looked convenient to wear.

Mom had me Nair my legs again before taking a bath, which I was now a pro at. She even got me more of the wonderful Vanilla body lotion from last time, and showed me how to properly wrap my towel around my chest, just like a girl would, and also like I experienced in my dream. I was a little disappointed in my short hair though when I saw myself in the mirror. She also made sure that neither my Father nor my little brothers saw any trace of the girl I was becoming before we headed out the door.

When I got back to my room, my Annie costume was laid out on my bed: a women’s button down shirt, a really nice fringed brown rawhide jacket, a blue-jean skirt which came down to just above my knees, suntan pantyhose, the matching black silk bra and panties, and the awesome cowboy boots and hat, which I would get to continue wearing as a boy.

Getting ready brought back all the amazing and fun things I felt the very first time I was completely dolled up as a girl. The panties and bra came first, which I instinctively stuffed (followed by an approving smile and nod from Mom), and then took on my next feminine task by carefully rolling on the suntan pantyhose, which felt a little bit softer than I remembered for some reason.

After getting dressed, I went with Mom to put on very light makeup touches - a bit of foundation, clear lip gloss, and a light coating of mascara.
Walking out of the house dressed as a girl was terrifying, but once I got used to the wind rustling my skirt, the swishing of my nylons, and the sound of my boots, I started to relax a bit.

As I opened up the door of the Cadillac, I was reminded of my dream as I smoothed out my skirt before sitting down sideways, then swinging my legs around as I shut the door.

“Where did you learn how to do that?” Mom asked somewhat admiringly.

“I don’t know, it just felt right to do it that way!”

“Nice job Honey Bunny!”

Driving up to school was a bit terrifying as I gazed down at what I was wearing, and as I stepped out of the car I was scared of immediately being made fun of our of the gate.

“Knock ‘em dead, girl!”

“Thanks Mom,” I replied somewhat half-heartedly.

But something quite unexpected happened.

No one recognized me!

I could hear the kids asking about the “New Girl” in the background, while I walked down the sixth grade hallway, as we were all in costume of some form or another.

In an interesting twist of fate, I was greeted by none other than Christina B!

I whispered to her when she asked me where I came from, “the same place as you – I’m Mike Jacobs in character as Annie Oakley!”
She had the strangest look of confusion on her face as she processed what I said, and then was extravagantly praising my look.

“OMG get out of here! You look incredible! No one will believe it’s you!”

“Wow thanks Christina!”

“Hey I have an idea,” she said. “Let’s pretend that you actually are a new girl until we go to homeroom! I bet no one else from our group will recognize you.”

“Sounds fun, I’m game!”

Sure enough, Christina introduced me to her crew of “popular girls,” as “Annie from Dallas, Texas,” and none of them recognized me. Being invited to sit with them before heading to homeroom was like an out of body experience similar to how I felt at the mall buying girls’ underwear. Any typical guy, even one they considered cute, wouldn’t be allowed anywhere near their table. At that point in my life it was the most exclusive club I had ever heard of. I had now achieved the elite level of status that Jimmy and Tom enjoyed from their Halloween escapade as ballerinas.
When the bell rang for homeroom, the jig would definitely be up as I walked to my usual seat. The room sat in stunned silence and Christina was loving the prank that she pulled on the rest of her crew, giggling uncontrollably, as I sat at my desk.

“Well, it seems Mike has pulled out all the stops on his biography costume - you look great!” Miss Russo was effusive in her praise. She was also my homeroom teacher, and looking back on it, knowing I would start the day with her subconsciously provided a measure of comfort.

My buddies were shocked to say the least.

“Hey Mike, you look like a girl!” one of my good friends, Jason Williams, remarked.

“Yeah, that’s kinda the point - I bet you wish you could look this good!” I responded.

“Haha, no way Dude!”

“Did you get invited to hang with Christina?”

“Oh, well uh, no. Damn, that was cool.”

The best part was when Christina chimed in.

“Oh yes, Mike, or well…Annie, will definitely be joining us for lunch today.”

That pretty much silenced the peanut gallery.

Standing in line with the girls was really cool, while the older boys passed by with a mixture of looks on their faces, ranging from outright fear to animalistic lust. Knowing who I really was made that more than a bit unsettling.

"Hey, check out the new girl!” one of them shouted.

Christina whispered in my ear with a forcefulness well beyond her thirteen years.

"We don't talk to them, just pretend they're clowns, or cartoons or something!"

When we sat at our table, I was immediately given the third degree in what in was wearing, from where I got my boots, and all the way down to the color of my underwear and what brand of pantyhose I was wearing. Christina asked me if I had Instant Messenger, and we exchanged screen names: I was Sk8erBoy, as a homage to being a hockey player of course, and hers was ChrissieBoo85, which I thought was kinda cute.

The rest of the day proceeded pretty much as usual, except for me now being an honorary member of Christina’s little club. Fortunately we didn’t have gym that day, so I didn’t need to worry about changing …and therefore anyone seeing my panties and bra. I was given permission to use the teacher’s restroom given that my appearance would have been a bit unsettling to the rest of the boys, should they happen to walk in on me touching up my lipgloss.

Being “one of the girls,” and seeing things from their side of the world, the good and the bad, was simply an amazing experience. What was previously shrouded in mystery suddenly became very real, and also a lot of fun. Fortunately, I was warmly welcomed by them, and the way they made me one of their own felt so nice. We were able to relate to each other in a way I never could have before, and that in turn gave me a new found appreciation for all that they do to maintain their overall appearances. They were naturally curious about everything I was wearing, where I got my jacket and boots, and got the giggles when I told them about some of the more difficult aspects of what I had to endure to become Annie (e.g., Nair).

“Wait until you have to try shaving, that’s a lot harder!” Christina said. “The first time I learned how to from my Mom I got a couple of really bad cuts, and had to wear jeans until my legs healed."

“That doesn’t sound so terrible, I wear jeans all the time!” I responded.

The girls then broke into hysterical laughter.

“Oh girl, you have no idea how frustrating it is not to be able to dress up before a game when we cheer, just like the high school girls!”
Christina’s friend Erin then chimed in.

“Yeah, like, being the only one not wearing a dress or a skirt, like totally blows.”

I secretly glowed inside when I thought back to my dream.

“I think I know what you mean,” I said, after we all had another giggle fit.

After lunch, I was really excited for the afternoon, when we delivered our reports and had a little party for everyone. When my friends Jason and Tim saw all the attention I was getting from the girls, they began to appreciate why I was “crazy” enough to come to school dressed as a girl…though they were not overly enthusiastic about ever trying it themselves.

Thanks to my Dad and some very old family traditions, I had already learned a lot about hunting and marksmanship…so while bringing anything related to firearms to school was a definite no-no, I was still able to relate some of my skeet shooting knowledge and experience to some of the really neat trick shooting Annie herself was famous for, and made the story really come to life in the eyes of my friends.
After my day as Annie, things pretty much returned to normal for me and my life as a precocious 13 year old.
I continued to hang with my friends, roughhouse with my brothers, and remained close to my family.
That said, there were a couple things after that were different…