Chapter 2: Decisions, decisions…

“Uh, Miss Russo,” I muttered and stammered, “I uh, well uh…”

“It’s OK Mike, no need to get all nervous! Who did you pick?”

“Annie Oakley?” I answered sheepishly.

Just about the whole class busted a gut laughing. I wanted to end it all right there and disappear into the deepest, darkest hole I could find.
“Settle down kids, settle down!”

My classmates didn’t want to get on Miss Russo’s bad side, so they hushed up pretty quickly. She was a formidable and yet also quite beautiful woman, standing about 5’10” in stockinged feet, and she routinely wore high heels, so just imagine how scary she could look from our still relatively young perspectives!

She dressed quite elegantly, always adorned in something that modestly accentuated her great figure and long dark hair and olive complexion, and from first sight I was absolutely smitten with her as a young boy in the midst of becoming a man.
“Mike, you have a couple of options, and it’s up to you to decide which way to go,” she said.

“This could be a really wonderful opportunity for you to display your maturity, and develop a brand new perspective from what you’ve experienced until now; or, if you decide this is too uncomfortable, then you can opt out of dressing in costume when you present your report.”
“PHEW!” I thought, “That could have been rough!”

Class picked up where we left off and resumed, and as I gazed at Miss Russo and how beautiful she looked in her blouse, skirt, nylons, and heels, I couldn’t help but wonder what dressing up as a girl completely would feel like now that I was given the opportunity.

WTF? Where did those thoughts come from, am I losing it? Dammit, get it together Jacobs!

The rest of the day went pretty much as a normal day would; lunch, recess, science class, math class, and final homeroom to make sure we had all our homework assignments listed.

My Mom arrived right on time at 3:00PM to pick me up that day to bring me to a hockey game. When I started middle school, I rode the bus, and one of the things I missed after graduating elementary school was riding home with Mom. Because of their schedules, Dad typically drove me in the morning, and that time was always special in its own way too, and another thing that I gave up after graduating from Elementary School. This was time that I really enjoyed, just her and me, talking about all kinds of different things as we drove wherever we needed to go together. Sometimes we’d even stop at our nearby convenience store for a Slushie on the way!

I hopped into the front seat of her adriatic blue Cadillac Coupe de Ville, complete with beige leather interior and the vaunted “gold package,” and like clockwork, Mom asked, “So Mikey, how was your day today?”

“Ah, pretty good I guess…and a little weird too.”

“Oh? Weird, how?” she asked, as we pulled away from the school and moved down the street.

“Miss Russo assigned us a new project in our reading class today. We’re doing biographies of famous Americans, and when we finish our reports, we get to dress up in a costume and present as our assigned character.”

“Wow, what a wonderful idea! What’s so weird about it?” Mom asked.

“Well, I uh, we had to pick at random, and I got Annie Oakley,” I blurted out.

“Annie Oakley? As in ‘Annie get your gun,’ the famous trick shooter?”

“Wait – what do you mean trick shooter?”

“Mikey, Annie Oakley was one of the most famous women, if not the most famous, women of the old west! It was often rumored that she was a more accurate sharpshooter than Wild Bill Hickock himself!”

Now that was really interesting to learn…I had just fired a gun for the first time with my Dad the previous winter on a hunting trip, and became fascinated with guns after spending the Spring learning how to target shoot both skeet and trap clay targets. I also enjoyed some of the new cowboy movies coming out in those days, like Tombstone, with Kurt Russell and Val Kilmer as Wyatt Earp and Doc Holliday. And those guys were definitely awesome.

“Wow that’s really cool! The only thing is, dressing up as a girl would be, well, I dunno…kinda gay and weird! I’m not sure I’d ever live it down.”

“Oh, I don’t know about that Mikey…didn’t a couple of your classmates dress up as ballerinas for Halloween just a few weeks ago?” Mom asked. “And Robin Williams dressed as a woman in Mrs. Doubtfire!”

“Yeah, but that’s acting, and Halloween…and it was still weird! The girls really liked it though, because their Moms made them really take it seriously – with makeup, tights, leotards, and everything.”

“And they got quite the write-up in your school newsletter too,” Mom said, and added, “This could really be a fun experience for us both if we play our cards right. Besides, by presenting in costume as your assigned character, you and your classmates will all be acting!”

My Mom was always thinking…that’s where I got a lot of my book smarts from, especially advanced math. She was great with numbers and computers, and really successful in the business world. I really looked up to and admired her, as despite her position, she managed to always carve out time for Dad, me, and my brothers when we most needed it. She could be really fun and creative too…my brothers and I really enjoyed playing board games with her, and she sometimes even invented her own games for us to partake in.

As I looked over at her, she had that whimsical look on her face whenever she was planning something fun for us to do. That probably spelled big trouble for me…