Annie, Get Your Gun!

By: Renee Elysse

Chapter 1 – An introduction, and into the wayback machine we go!

Most of my friends and family know me as Mike Jacobs. What I now think of as my “male persona” involves being a successful executive, outdoorsman, handyman, and one of the “guys’ guys,” so to speak. I enjoy the company of beautiful women, wine, and song, as well as hunting, guns, cars, watching football, and playing hockey, among other things.

Little do they know that I also have a much softer, feminine side: my alter-ego, if you will, and her name is Renee. I’m about 5’8” tall and keep myself in really good shape, weighing in typically between 160 and 170 or so, with a lot of lean muscle - so I’m not overly bulky, but by no means effeminate looking when presenting my male persona to the world…in fact quite the opposite, especially in a power suit. My stature, such as it is, also enables me to enjoy all sorts of women’s clothing options, and as a size 12 and a ladies medium to large, I have built up a considerable wardrobe! I’m also fortunate enough to fit into a women’s size 9 shoe, or 39/40 EUR, and have also collected at least three dozen pairs of shoes, ranging from ballet flats all the way up to 5” Louboutins.

Over the years I’ve had many varied and wonderful experiences enjoying life as Renee. To take a step back as to why I have a second name, when I transform into “girl mode,” I look completely different, especially my eyes - and my energy even shifts from a masculine frame of mind, to a feminine one. This effect is so pronounced that I once bumped into a colleague at a bar I was visiting “en femme.” During a night out with a few girlfriends, I was perched on a barstool in a beautiful black cocktail dress, sipping an expensive glass of scotch, and showing off some serious cleavage and a generous amount of leg, simply because I found it enjoyable to display my assets. Now, I could vouch for him being straight as an arrow, having been to a number of strip clubs with him in guy mode. Granted, that night, he was definitely shitfaced, but nonetheless, he flirted with me shamelessly - even making a clumsy attempt to grab my ass at one point! He really had no clue who I was.
As I was saying, the guy most people know disappears, and a seemingly well-endowed, curvy in all the right places, and stunningly beautiful woman emerges from the shadows of the man most people see. I now think of myself as bi-gendered: A strong masculine persona, and and elegant feminine persona, both sharing the same physical body. I mostly present to the world as my male persona. That said, my inner lady sometimes needs to get out and enjoy herself; and I always make sure to set aside as much time as I can to let her take over completely. I find this special time immensely pleasurable, and quite sensual in a way that I never come close to feeling in “guy mode.”

When Renee comes out to play, there’s a multitude of wonderful feelings that wash over me as my energy and mindset shift from masculine to feminine, and just to name a few: that silky smoothness and softness of my shapely legs that comes from having them totally shaved; being able to wear a revealing top, or even a swimsuit with my chest and arms completely hairless and smooth; wearing delicate, sexy lingerie and looking just as good as the curvy model inspiring the purchase; being complimented by another woman on a beautiful dress; spraying perfume on my wrist and tossing my long hair over my shoulder; having doors held open for me (why on Earth do some women get all worked up over this? It’s awesome!); the sound of my stiletto heels clicking on the pavement, and just feeling extremely sexy overall from knowing that the sound is mine! Oh, and being wined and dined in girl mode, and enjoying all that goes with it, included being treated like a queen and tingling all over the whole time, is simply amazeballs!

I’m mostly attracted to women, and really enjoy dating them and being with them as a guy in a traditionally masculine, dominant sex role…but I’ll be honest. I have never felt attracted to men at all, ever, while in my male persona. And in most of my early years as Renee, I politely declined the attention of male admirers on more than a few occasions.

However, I’ve made an occasional exception for some incredibly wonderful, charming, and frankly well-built (and hung hehe) older gentlemen, who took an immensely active interest in pursuit of my feminine self, and treated me incredibly well. The further I got into discovering Renee, and how these handsome men felt about me based on the beautiful woman I was presenting to them, the more I was drawn to their flirting, and played along with gentle encouragement - rather than being repulsed by it as I would be in typical Mike mode. I learned to enjoy their attention and gifts from being something they desperately wanted, which gave me a special kind of intoxicating power once I accepted and embraced it. I found myself drawn to them, and their kind gestures, as things escalated and fully validated Renee’s womanhood, as a growing desire bloomed inside me.

Those experiences made me feel a whole range of things, from happy and secure while being held and letting them take the lead when we danced; the excitement that comes from being an object of desire and learning to enjoy the enticing nature of feminine sexuality itself, to all the resulting delights from being on the receiving end of so much unbridled passion.

Those stories are for another occasion though…the tale I am about to share with you all goes back in time about 20-odd years, to a fateful day when I was in sixth grade…

Back when I was a boy of about 12/13 years old, I was (and still am) very curious about the world and wanted to know everything about it. A gifted and bright student, I was in an advanced reading class with all the top kids in my sixth grade cohort. Growing up, I had moments when I would see things, or feel things, differently than most, on account of my high intelligence and inquisitive nature. I quickly learned how to hide most of these thoughts in order to better relate with the other kids, and learned how to live in my own little world while being a part of theirs at the same time.

One of the things I was often curious about in those days, given my budding interest in girls, was how they felt when they were dressed up in a fancy outfit - like dressing for a special occasion, and especially when paired with pantyhose. This was happening more and more frequently in sixth grade. Between our concerts, sporting events (which, starting in Middle School, required us to dress up prior to games), and various other competitions, the girls in my class wore some really beautiful outfits.

At that time, my buddies were mainly interested in video games, and girls as a concept; not so much what they wore or how they wore it. I was careful never to share how much I loved it when the girls in our class wore nylons, nor my observations of different styles and fashions, and knowledge thereof from occasionally borrowing my Mom’s magazines. My curiosity about how it felt to wear pantyhose with a dress or a skirt nevertheless still persisted. Oh, I should probably explain where that came from…

As a brief aside, when I was much younger, probably about five or so…I tried on a pair of my Mom’s pantyhose that were left on my parents’ bed, and absolutely fell in love with them. I was hooked from the get-go, and would sneak a pair to wear in a safely private place whenever I could. My nylon raids would often involve the dirty laundry, or seizing the opportunity whenever Mom forgot a pair in the bathroom.
Anyway, back to my sixth grade advanced reading class…

One day, my all-time favorite teacher, Miss Russo (who I also had a major crush on at the time) announced that we would be doing a special project: biographies of famous Americans, and when we were done writing them up, we would be presenting our book reports dressed in a costume to match with our American icons.

I remember thinking - wow, this could be really awesome! I could get one of the Presidents, or a famous actor like Kevin Costner, a rock star like Dave Grohl, or even Troy Aikman…the possibilities were endless.

The kicker was, we would draw our characters at random. I figured there was no way this could go wrong.
After sorting through my classmates in alphabetical order, I was called up to the front of the room, and stuck my hand into the top hat she used for us to pick our characters.

Miss Russo asked me as my hand shuffled around and drew out a name, “Well Mike, which of our famous Americans have you chosen?”
I opened up the little piece of crinkled up paper, my heart froze, and time stood still for what felt like forever:

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…

Chapter 3 – Never lie to Mom!

After we got home from the game, I decided to knock out my homework quickly so I could play my new Mario 64 game, which came with our Nintendo 64 that we just got. My buddies were always psyched when we invited them over to play Mario Kart 64, which we picked up a little bit afterwards. My brothers, Nick and Ben, both a few years younger than me, would love racing me as Mario and Bowser, while I typically played Wario as I got a kick out of his laugh, and his driving style clicked well with my gaming skills. We’d play that thing whenever we got the chance.
While I was running around taking out goombas and flying across the countryside while waiting for them to finish their soccer practice, in my mind I was going back and forth about the whole Annie Oakley thing.

On the one hand – it would be really weird!

On the other hand – Mom thinks it could be fun, and she’s an expert on that topic. Also, the girls really loved it when Jimmy and Tom got all dressed up for Halloween…even though the kids laughed when I pulled Annie’s name out of the hat, Jimmy and Tom had it made with some of the most popular girls in our class.

Even though I played hockey and was a pretty good defenseman, my friends tended to be the smarter, quieter kids, not quite the “popular” groups developing that would eventually be the typical jocks and cheerleaders…still though, this could be quite interesting, as I would finally get to figure out what it felt like to wear a skirt with nylons.

On the other hand – what would my friends think? Would they make fun of me, or worse, shut me out of our hockey team?

And of course, the giant Doozy that I hadn’t even considered: “What would Dad think!?!”

This could get seriously out of control!

I’ll see if Mom and I can talk together after dinner…

After we ate a wonderful home-cooked meal, I asked Mom if we could talk about a homework question. My Dad knew that I always went to Mom with the more difficult Math problems…while no slouch himself, he also appreciated that Mom was way better with numbers. Dad was our resident History buff, and really good with Science, so I usually went to him for guidance in those areas.

We went upstairs to my room and I shut the door.

”What’s got you stumped Mikey?”

“Actually it isn’t about Math…it’s Annie Oakley.” She could see the clear expression of worry on my face in the way that Moms always do, just intuitively.

“Oh, you’ve been thinking about that quite a bit, have you?”

“Yes, and while I’m thinking it could be a neat experience, I’m scared too and not sure if I really want to do it,” I said.

Mom came over and gave me a big hug. Isn’t it amazing how Mom’s hugs always make everything better?

“Mikey, you’ll always be my honey bunny and my wonderful, brilliant, handsome Son. I was thinking on the way home about how much fun we could have, going shopping for all the things I’d need to make your costume, buying some special clothes for you to wear, and doing something just for us, like the time you spend with your Dad fishing and hunting. And besides, I’ve always wondered what it would be like to have a daughter.”

Now I really needed to think hard on this. This really could be neat and fun, as she said. Then she threw me a curve ball out of left field.

“Mikey, do you like to wear my nylons?”

I froze again, just like in class, only this time my face turned bright red.

“Uh, um, Mom, uh, why would you think that? I don’t, well, I - never!”

“Mikey, I found a pair in your room a few months ago…you must have forgotten to return them to the laundry.”

Damn, she nailed me. And I thought I was so careful!

“Michael John Jacobs, don’t you lie to me! I won’t punish you or tell your father if you tell me the truth.”
Mom looked at me with that “stern” face of hers that made it impossible to do anything else but be totally honest.
I let out a huge sigh. “Ok Mom. Yes.”

“And why do you like to wear them?” she asked, raising an eyebrow and looking at me quizzically.

“I just really like how they look and feel on my legs. One time, when I wore your navy blue ones I pretended I was Superman! Plus they make my legs look like the girls at school do when they get all dressed up, and I love when they do that. And I really love it when you dress up too.”
My face was red as a tomato.

“Please don’t think I’m a wimp or a sissy!” At that point I was so overwhelmed that I started to cry.

“Oh Mikey, come here.” Mom held me while I bawled my eyes out.

“Mikey, you’re at an age where you’re going to start noticing things about girls that you never thought about before, and feel some things around them that you never felt either. Your father will tell you more about this very soon, but now I’m going to tell you a secret.”

I wiped my eyes and blew my nose. “What secret?”

“We women, and girls, even though we rarely admit it, really like it when guys notice how we dress, when we look pretty, and want to give us their attention. Sometimes I dress up extra nice just because I know your father loves it and I want to make him feel extra special. What you told me about the girls in your class doesn’t make you a sissy at all. Your father certainly isn’t. Do you like it when Miss Russo wears nylons?”
Now she really had me. I loved, admired, and deeply respected my Father, and the last thing I would ever want was to somehow fall short as his oldest son.

“YES! I love how her legs look when she wears them!!!”

“Mikey, that’s all part of becoming a man, and that’s what happens when boys start taking a more active interest in girls!”

Wow, that made a ton of sense. I thought I was going crazy over the last few months.

“Don’t worry about your Dad. You’re his oldest son and he loves you very much. He’s very proud of you.”

“I know that Mom! I just don’t want him to think I’m a sissy if I dress up like Annie Oakley!”

“Let me worry about explaining this to your Father. You worry about getting a good night’s sleep.” Mom kissed me on the top of my head and gave me another big hug.

“And Mikey – from now on, if you want to wear my nylons, just ask my permission. They really do make your legs look and feel nice and energized, and I can see how you might like that same feeling too. You know…if you decided to dress up for your book report, you could definitely wear them as part of your costume.”

Now that really sounded kind of…well I didn’t really know how to process it, but I felt these strange butterflies in my stomach when I imagined what it might be like…

“Ok Mom, I won’t steal your nylons anymore. I love you!”

“Love you more Honey Bunny, sweet dreams!”

Chapter 4 – Preparing for a shopping trip with Mom

The rest of the week turned out to be pretty normal. School, homework, video games, and family dinners. Well, that and the decision I was wrestling with. On Saturday, after breakfast when my brothers went out to play in the back yard, and my Dad went to have some specialty engine modifications done on his antique car (a 1968 Plymouth Fury), I decided to help my Mom clean up the dishes.

“Hey Mom, I can’t stop thinking about what it would be like to dress up as a girl completely, and I think I’d like to give it a try.”

“Really, Mikey? So you want to present your book report in character, as Annie Oakley?”

“Yeah!”

Mom’s face lit up with a big smile, and she leaned over and kissed me.

“After your baby brother Ben was born, your father and I knew we weren’t going to have any more children, and I always wanted to have a little girl to share some things with that typically pass from mother to daughter. We’ll have some special time together, just for me and my oldest.”
I naturally had mixed feelings about this. On the one hand, I was really starting to notice girls in a different way from ever before, and was all kinds of curious about them. On the other hand, I had no desire whatsoever to give up being a boy and spending time with my buddies on the hockey team. Mom seemed really excited about this though, and her energy was quite infectious. That got me just as amped up.

“OK Mom, I’ll do it!”

“Wonderful! I think you’re really going to enjoy this. This will be an experience that will give you a perspective on all kinds of things that very few boys ever get to benefit from. When you start dating girls, I think you’ll have a new appreciation for them too, that will be well beyond most other boys your age.”

What in the world was I getting myself into?

“Why don’t you go take a shower and get dressed. But before you get fully dressed, I need to take some measurements, so just put on a t-shirt and your undies. Then we’ll take a shopping trip and get you a nice biography of Annie Oakley and some of those Star Wars books that you like, along with a few other things we’ll need to make your costume!”

“Right Mom! I’ll let you know when I’m done.”

At that time, I stood about five feet tall and weighed around a hundred pounds. I took a shower and got dressed in my underwear and t-shirt so she could measure me, then called Mom in to let her know I was ready.

She came in with her measuring tape and rolled it across my arms, legs, chest, waist and hips, double checking each.

“Let’s see…26 inch waist, 30 inch chest…we’ll need you to try on a few different things to get the sizing just right but I think you’ll be a perfect size 2!”

I really had no clue what that meant and why she seemed so excited by that idea, and stared at her somewhat dumbfounded.

“Ok Honey, I’m gonna write these down and then we’ll head to the mall!”

I threw on a pair of jeans and a hoodie, and caution to the wind. Off we went!

Chapter 5 – Shopping and seeing myself as a girl

Going to shop with Mom to buy girls’ clothes was like an out-of-body experience. As we walked through the usually forbidden ladies’ underwear section of the store, with all those delicate materials and girlish colors, I couldn’t help but feel more than a little self-conscious. I had never noticed how many different styles of underwear girls had to pick from, versus the boxers or briefs I was accustomed to. They also had lacier and silkier “briefs,” and bikinis, “boyshorts,” and something called a thong. Mom saw me ogling that one just a bit, and said, “You’re a bit too young for those…maybe when you’re older,” and then winked at me and proceeded to pick out a few pairs of silky looking briefs in white, black, and pink. I shuddered to think what that might mean!

As we continued through that area of the store, I watched Mom pick out a couple of bras in white and black, and she remarked on the size – 30A.

Without really thinking about it, I asked "What size do you wear Momma?"

"34D, sweetie," she answered. " I was originally a"C" until I gave birth to you and your brothers." She also found me a pink babydoll nightie, along with some sheer L’eggs pantyhose in nude, suntan, and black, in size A, along with a pair of navy blue tights. “These will fit you a lot better than mine,” she teased with another wink. I blushed, at a loss for words.

Then we moved on to the makeup section, and she carefully selected a couple shades of lipstick in red and pink, blush, an eye shadow palette, mascara, and foundation. It was a bit wild knowing all of these typically “verboten” items for boys were all for me, and it was giving me goosebumps, along with a growing set of butterflies in my tummy.

She then threw me for a loop when, after finding the right skirt, button down shirt, and fringe-sleeved rawhide jacket combo to simulate Annie Oakley’s style of dress, she continued buying more clothes - a few different styles of skirts, cashmere sweaters in navy, black, and pink, a cream colored silk blouse, a black “sweater dress” that looked like a super long turtleneck, and an incredibly beautiful royal blue a-line dress, covered in all kinds of silky looking lace, with a fluffy looking ruffled skirt! I couldn’t imagine wearing something so distinctly feminine!

“Mom, why are we buying all these extra things on top of my Annie Oakley costume?” I asked.

“Well honey, I thought you would benefit from getting used to wearing girls’ things before you go to school dressed as one…and who knows, you may even want to indulge your feminine side again in the future!”

At the time I thought that sounded crazy, but in retrospect, I had no idea how right she was.

Lastly, we headed to the shoe store. Mom deftly explained to the saleslady that I was taking part in a school play, and would need to try on a couple pairs of girl’s shoes for the part I landed, along with some western style boots for an upcoming trip we were taking. Dang that was embarrassing, and I blushed again. The associate was all professionalism as she had me start with the boots, and handed me the nylon footies I would need to try on the heels, and proceeded to measure my foot. I came in at a women's size six in those days. We bought a pair of awesome cowboy boots that reminded me a lot of Doc Holliday’s in Tombstone…or I guess cowgirl boots (hehe!), and a couple pairs of heels - two inch brown penny-loafer style heels with a blocky looking heel, and a 2” pair of black pumps with pointy toes, like Mom would wear to work. I was surprised when Mom also picked out a delicate-looking pair of nude heeled sandals with all kinds of straps. I didn't walk around in any of the ladies’ shoes yet, as I was in boy clothes, so she discreetly slid them on, felt my toes and heels to make sure they fit properly, and quickly slid them off without too much fanfare.

After the mall, we drove along an unfamiliar route for about a half hour to a wig shop. I would come to learn that the store catered to a very special clientele that included include drag queens, crossdressers, and brave women undergoing cancer treatments. After browsing the different lengths and styles, we selected a beautiful long, flowing brown hairdo with some blonde highlights – very similar to my own natural hair color.

On the way home, Mom told me that she worked out a plan with Dad to take Nick and Ben to visit our uncle's cabin up in Maine to help him winterize it, which resulted in us having the house all to ourselves for the next couple of days.

When we got home, Mom instructed me to run a bath, as opposed to my usual shower. I had some early leg hair starting to grow, which would look “just awful” under the nylons according to Mom, so she handed me a bottle of Nair and told me to cover my legs in it. She also said to let it sit for about ten minutes before getting into the tub. That felt (and smelled) really weird, but after my bath I was amazed at how soft and smooth my skin felt. She even got me some girls’ flowery deodorant to use, and some really nice vanilla-scented body lotion to cover myself in. She also made sure I covered my chest “like a proper lady” with the towel!

When I saw my first outfit laid out on my bed, a navy blue cashmere sweater, accompanied by a dark green tartan plaid skirt, and all the underthings beside them, not to mention the high heeled penny loafers next to my bed where my Air Jordans would typically be, the reality of my situation set in. I felt an incredible rush of feelings mixed together like I had never experienced before in my life. At first I was incredibly nervous and wasn’t sure what to do. Mom instructed me to start with the panties before taking a brief exit, and returning once I was “decent.”

Sliding the white silky panties up my now hairless and scarily girly looking legs was a strange sensation at first, but I was amazed at how nice they felt.

Mom helped me out with the bra since it was my first time wearing one, but she insisted I master the technique of reversing the bra to hook it, and then flipping it around. “When you get really good at it, you can clip it behind your back without looking, just like me!”

“When would that ever happen,” I thought to myself.

We then stuffed it with two bunches of tissues. As we did that, Mom enlightened me that it was a common trick used by girls my own age, as they were developing.

“Why would they do that?” I asked.

“You have no idea how competitive we are with each other Mikey, and I remember this little item being particularly intense when I was growing up!”

Next she handed me the sheer nude pantyhose and instructed me to roll them up first, and slide them up to my knees one at a time before pulling them up the rest of the way. I imitated Mom’s usual technique for doing this perhaps a bit too well, because she was surprised at how good I was rolling them up my legs. She even complimented me with an “Atta girl!” after I instinctively straightened them out as I pulled them up over my thighs.

I thought they felt good before, but putting them on over my freshly hairless and well-moisturized legs was indescribably great. I was a little embarrassed because I developed an erection!

“Oh my, you really do like nylons!”

“Sorry Mom, can’t help it, they feel amazing!”

Then I first stepped into, and then lifted up, the plaid-patterned green, blue, black and white skirt, zipped up the side, and quickly noticed that it had a silk lining inside that felt very nice against my pantyhose-covered legs. It came down to a few inches above my knees, and the pleats flared out just enough so that I wasn’t outwardly showing what was happening under my panties and nylons. It was a strange and also pleasurable sensation to see my lower half in a skirt and pantyhose for the first time…and just like a lot of the girls in my class.

I then put on the blue cashmere sweater, which was way softer than anything I had ever worn up to that point, and slid on the penny loafer style heels. They made my nylon-clad ankles and feet look incredibly feminine.

I was tempted to check myself out in the mirror but Mom insisted we wait until after my makeup was done.

After putting on some Olay facial moisturizer, a light coating of foundation, mascara (which tickled quite a bit!), a bit of brown-hued eyeshadow with some gold highlights, blush for my cheeks, and the pink lipstick, we lowered the wig onto my head. I couldn’t believe how nice it felt to put on the lipstick!

I was completely unprepared for what happened next when she told me to turn around.

When I saw the beautiful, stunning girl in my mirror it took about five seconds to realize that the beautiful face, lips, and shapely legs all belonged to me.

I looked like a younger version of Mom!

“Oh my God, I’m pretty!”

“How do you feel Mikey? Although based on your current look Mikey just doesn’t have the right ring to it…”

“How did you…how can I…look so beautiful?”

“Great genetics Honey Bunny – you look a lot like me!” Mom then set her own pretty face next to mine while I stared at the mirror dumbfounded, and kissed the side of my head. She was positively beaming.

That was a bit weird because most people thought I took more after my father in the looks department. I guess the truth was that I really did have a number of wonderful attributes from both of them. A lot of people thought she resembled the lead actress of the Will & Grace show, Debra Messing, in her prime, in case you're wondering what I might have looked like ;).

“Let’s get you some jewelry! A pretty girl like you should have some nice accoutrements!”

Mom had me hold her hand as I got used to walking in heels, and followed her to large the bedroom she and Dad shared, and was enjoying the sound of MY heels clicking the wooden floor of the upstairs hallway.

They had a late 70s-era big dresser with a mirror that spanned its entire length, and I was immediately greeted by my feminine image again. While I could feel every step on the heels and was really enjoying the sensation of my nylons and skirt brushing together, I was still having a hard time believing I could look so incredibly gorgeous.

Mom reached into her jewelry box and pulled out a beautiful gold necklace, a couple of bracelets, and some clip on dangly earrings.
She then pulled out her Chanel No. 5 bottle and told me to put out my wrists towards her, facing up. She spritzed it on both, and then behind both knees, which surprised me, and tickled my pantyhose just a little.

“Oh God, I smell just like Mom does,” I thought to myself.

The combination of everything I was experiencing up to that point was soooooooo good. I felt warm and tingly all over, and also…Girly…Feminine…and also vulnerable with my heretofore budding machismo completely vanished. I reminded myself of the prettiest girls in my class while I looked into the mirror, and then thought that I might be becoming a sissy, or gay, or turning into a girl and leaving my masculinity behind forever. Suddenly I got really scared and started to form tears in my eyes.

“What’s the matter Honey?”

“Mom I’m afraid … I really like how I look and feel as a girl, and does that make me gay? What if I want to dress like this again? I don’t want people to think I’m a sissy!”

Mom wrapped her arms around me in that magical way that only Moms can do, and instantly made everything better.

“Oh honey, the clothes you’re wearing won’t make you gay…you still have a crush on Miss Russo, right?”

I sniffled as she handed me a tissue to wipe my nose. “Yeah, but what if the boys think I’m hot and start hitting on me?”

“Well that would actually make them gay, wouldn’t it?”

That made me start giggling hysterically. Incontrovertible Mom logic is a wonderful thing.

“That’s better sweetie, now let me fix your makeup.” Mom had me sit down at her makeup table while she touched everything up. I started to feel really special sitting there, after watching Mom get herself ready for work so many times in my younger years.

“And besides, what you’re doing take a lot of guts…I’m sure most of the other boys in your class wouldn’t have the courage to try this!”
“You’re right Mom, and I bet most of them wouldn’t look half as good as me!”

“Now THAT’s the spirit! Let’s go make some popcorn and watch a movie, and then we can have our very own fashion show!”

Since we were having a mother / daughter night, little did I know that she rented “Clueless,” starring the very beautiful Alicia Silverstone, who I immediately started crushing on heavily. It felt really good to be dressed similarly to the girls in the movie. We had so much fun laughing through some of the really funny parts, like when Cher was learning how to drive and had a great line for the instructor, “you try it in platforms!” And of course there was the infamous scene with the “underwear dress.” Both parts of which, based on my newly acquired attire, I could strangely identify with. At one point without realizing how I looked, I took my shoes off and sat on our leather sofa like a young girl typically would, with my legs curled up against my chest, and thoroughly enjoying the feel of it through my pantyhose covered legs and the nylon covered soles of my now almost-bare feet. Mom even snuck a picture of me like that! I watched my first “chick flick” totally dressed as a girl - and survived!

Mom then taught me all the important things to be aware of when wearing a skirt, like how to smooth it out before sitting down, to cross my legs either at the ankles or knees, and to take smaller steps in the heels. I was amazed at how I naturally started swaying my hips when I walked, and REALLY enjoyed the sensation of my legs brushing together, and the swishing sound of the skirt and nylon, when I strutted my stuff like a glamorous model.

This was turning out to be a lot of fun!

Chapter 6 – Another new experience

Later that night before Mom and I got into our fashion show, I had a little time to myself while she cleaned up, and headed up to my room after putting my heels back on. I promptly shut the door and sat down on my bed, and stared at my legs, marveling at how they looked and felt, all smooth and clad in nylon. Without even thinking about it, I started rubbing them together, then leaning back on my bed and scissoring them back and forth, like you’d see in those Jane Fonda exercise videos. Then I walked over to my mirror and crossed my legs across one another while standing, imitating a pose I had seen in numerous fashion magazines. I bent at the waist and began sliding my hands all over them, and then the two little mounds on my chest…I thoroughly enjoyed watching myself feel up the gorgeous looking girl in the mirror, and felt more than a bit strange, as I could feel all the softness of what I was wearing and the wonderful sensation of my hands through it all while I did it. It was pure sensory overload, and I got completely caught up in the moment.

I loved the sensual nature of having my legs massaged, and in turn the feel of the silky nylons covering MY legs in MY hands, and I began feeling positively euphoric. I was tingling all over, my stomach was fluttering like crazy, I started to shake everywhere, and then for what felt like forever, was a sense of total bliss and joy unlike anything I had ever experienced. My heart started to race. While I could feel the waves of bliss radiate out from a pulsing right behind my balls to under my stomach, up to my chest, then down to my nylon covered toes and up to my ears, all of a sudden out of nowhere, I got weak at the knees, saw flashes of light and started having an absolutely earth-shattering orgasm, and then immediately plopped down on the floor as my legs turned into jelly. While I was being totally consumed by all of those very intense feelings, now all at the same time, I started moaning, continued to shake uncontrollably, and felt wave after wave of shorter and more intense pleasure everywhere. At some point while all that was happening after I landed on the carpeted floor of my room, I began spurting wad after wad of warm, sticky wetness into my panties and pantyhose, all while holding onto the floor for dear life. I could feel the spurts continue as I was panting and gazing back through my hazy eyes, and now messy long hair, at my completely feminine looking silken legs and my feet in the heels.

I think Mom heard me land on the floor, because no sooner did I stop shaking and start coming back to reality, that she was knocking on the door to check on me.

“I’m OK Mom, just need to go to the bathroom!”

I quickly regained my strength, pushed myself up off the floor and ran past her, my block heeled penny loafers making an incredible noise echoing all the way down the hall, and shut the door behind me, locking it in one fluid move. I kicked off my heels and immediately pulled everything off below my waist, (though carefully enough not to cause a run in my new pantyhose), and frantically wiped away the cloudy white mess I made in my panties, which was starting to soak through. I was confused at first about what happened; and then remembered back to a sex-ed class we did at school, and some subsequent periodic experimenting I had previously done with Dad’s Playboy magazines, when it all “came together” (hehe no pun intended)…but those feelings were nowhere near intense as all of these were.

I was so embarrassed and ashamed at first, and needed a few minutes to get my bearings again while I tried to figure out what just happened. Then I remembered that we still had our fashion show coming up, and Mom was encouraging me to enjoy every minute of it. That brought everything back into focus, and helped me catch my breath.

Putting everything back on and feeling all the wonderful sensations that accompanied the nylons going back up my smooth legs made me feel a lot better, and get back into the fabulous swing of things. I borrowed a couple of Mom's brushes to get my temporary flowing locks back in order, unlocked the door, and headed back out. She never asked about what happened, but somehow I think she knew...or at the very least sensed, how much I was enjoying everything.

Mom got herself all dolled up too, changing into a beautiful black evening gown with a flowing long skirt and a beautiful pair of exquisite coffee-colored silk stockings that felt way different from the pantyhose I was wearing – a lot more silky, soft, and delicate. She then explained to me that she would wear them for extra special occasions, and walked me through the mechanics of wearing a garter belt, which sounded quite complicated.

“You’re still a little too young for these, but maybe we can get you some stockings when you’re a little bit older!”

What had I gotten myself into?

We continued modeling all of my other outfits, including the "distressed" denim skirt with the black cashmere sweater, which I liked because I could see my nylon covered thighs through the ripped parts. Next came the cargo-styled skirt with the pink sweater. For our next outfit, Mom had me change into the black pantyhose and handed me the charcoal dressy-type skirt, which came to just below my knees, and the off-white silk blouse. I put on the black pointy-toed pumps and enjoyed wearing the same shoes I saw Mom wear to work on numerous occasions. Despite the modesty of what I was wearing, those pantyhose somehow felt naughtier, and therefore sexier, to me, as I suddenly thought of all the girls I saw in music videos wearing them. I shuddered a bit standing there in my heels, marveling that the bottom part of my legs looked a lot like theirs. She even put my hair up in one of her hair clips, and said “with that look you could join me for take your daughter to work day!”
After the blouse and skirt, I put on the black turtleneck dress, which was shorter than anything I had worn up to that point. I loved how my legs looked wrapped in the black pantyhose, and the black heels perfectly complimented the overall ensemble. I started to get the butterflies and goosebumps again when I sat with my legs crossed.

Last was the lacy a-line royal blue dress, which Mom had me switch over to the suntan pantyhose for. It was incredibly girly looking with its lower-cut neck and non-existent sleeves, which made my exposed arms look eerily delicate and feminine. The flared ruffled skirt, which came up to my mid-thigh, also made my legs look even more girly than the prior outfits I wore. Mom helped me buckle my feet into the 3.5” nude heels, which was both scary and exciting. As I looked down at my feet in these incredibly sexy looking shoes, I had another new sensation, like I was becoming a more mature girl, or even a young lady. I felt like a princess, and I loved it! Without thinking, I sang out “Man, I feel like a woman,” like Shania Twain, and we both laughed really hard at that.

I was very wobbly when I tried to stand up the first time in the much thinner and higher heels, resembling the movement of a baby deer (which Mom didn't hesitate to mention) and struggled a bit walking in those and almost fell, until Mom helped me get the hang of the right technique. She had me take the shoes off, and showed me how to walk on the balls of my feet, "toe to heel," while taking smaller steps. When I put them back on, I was able to stand much better, and soon got into the right rhythm with the heels. This caused me to naturally sway my hips a bit more dramatically than before. She also taught me that girls lead their steps with their hips, rather than shoulders, like guys do. I was so proud of myself once I was able to do it. We went up to Mom and Dad’s room so she could have me demonstrate my “catwalk” in their full length mirror opposite the dresser. I noticed that the higher heels made my legs look even better than before. Mom even complimented me on that!
“I think most of the girls in your class would be jealous with how amazing those legs of yours look, Honey Bunny!”

I couldn’t help but blush. “Thanks Mom, this really IS a lot of fun! I had no idea!”

We eventually got to the Annie costume - the instigator for this wonderful evening. We even took a couple of pictures, just for us, of me in my western style jacket, button-down shirt, knee length denim skirt, and boots, while holding my 20 gauge shotgun! As all good things eventually come to an end, well into the night and much later than she’d ever previously let me stay up, Mom finally said it was time for me to start getting ready for bed, and I reluctantly agreed.

I was sad to take off my makeup and almost disappointed to see “boy me” emerge from the cocoon of femininity I was immersed in. After getting washed up and re-moisturized, mom reminded me of my special pajamas, and I slipped into the pink babydoll nightie and matching pink panties that she bought for me earlier. OMG – a whole other amazing set of feelings came over me as I lifted the thin straps into place over my shoulders, wearing such a delicate, feminine garment. The silky softness of it was out of this world fantastic. Below the neck I looked and felt like a teenage girl, and once again felt that same mix of unsettling but also delightful butterflies in my tummy, and tingles in all kinds of places, as I did earlier. Deep down, I absolutely loved how I looked and felt.

I was still on a high from all the things I got to experience that day, and it took me awhile to fall asleep. After a bit of tossing and turning, and also feeling the nightgown rustle around against my smooth legs and chest under my sheets, I eventually slid into a restful, deep slumber…

Chapter 7 – Discovering the girl within

The strangest thing that followed my fashion show / “mother-daughter night” was my second to last dream, as I slept in a beautiful pink babydoll nightie that evening. As it began, I woke up in my room to my radio alarm at what was apparently 5:30 in the morning, and I was wondering why I set it so early just to get ready for school. The Juice Newton song "Angel" was playing on the oldies station it was set to. Everything seemed normal at first, except...I felt a strange weight on my chest when I got out of bed. I had apparently grown breasts during the night! As I shut my alarm off and the fog of sleep cleared, I knew I had to get ready for school. As I opened my closet, instead of all my usual clothes being there - shirts, jeans, jackets, and hunting stuff, I had a totally girlish wardrobe – dresses, skirts, sweaters and blouses, and oddly enough, also hunting stuff…and based on the cheerleader uniform that was hanging in the closet, apparently I made our town’s varsity cheer squad. I was also taller than I remembered in the mirror. Wow, I must be in High School!

As I looked in the mirror, I at first thought I had a wedgie, and looked at my derriere, and saw that I was wearing a pair of those thong style panties we saw at the mall. When I realized what I was wearing, the feeling was not at all unpleasant as it tickled my butt and showed off my ass and shapely thighs nicely. I also grew an incredible thick mane of long dirty blonde hair, a few shades lighter than what I had now and tied behind my head in what was left of a very messy French braid. It was basically a much longer photo negative equivalent color of my current hair. Even with no makeup, the girl in the mirror wearing nothing but a white camisole and tropical flowered thong was stunningly beautiful. She had an incredible shape, accentuated by beautiful curves. My calendar on the wall beside it indicated we had a game tonight, so I would need to look really good at school.

Typically before a game, all the cheerleaders would dress up in really nice clothes, and I was no exception.
After I instinctively sat down to pee, I couldn’t help checking out my incredibly sexy bare behind as I stood up in front of the mirrored vanity in our bathroom. I let my gaze linger at the beautiful rear end and legs of the girl in the mirror, and expected to sprout a woody. As I looked down at my manicured, painted toenails and saw nothing between my legs, I was shocked. The mound of fur I saw there in place of my dick was a bit scary, but far more intriguing, as I was reminded of what I saw and also enjoyed in Dad’s Playboy magazines.

I stepped into the shower. As the water started to rush over me, I felt a lot more sensitive to every little sensation than I can remember ever feeling before. My long mane of hair was now glued to my back, and the little water droplets running along my shoulder blades, down my now bulging chest, then to my soft and tight tummy, and all over my incredibly smooth legs all felt like they were caressing and massaging every inch of my new womanly body. I gazed down over my sensitive breasts at my belly button, which now appeared a little larger than I remembered it. I felt wonderful as I started to delicately explore what was between my legs with my fingers. I immediately arched my back as I felt an explosion of pleasure shoot out to my breasts and nipples. After a nice long moan, I instinctively then took some body wash off the shelf and used my very own loofa on my arms, belly, backside, pussy, and legs, before shutting the water off. I then covered my beautiful legs with women’s shave gel, and began carefully shaving them all the way up to my waist, and then did my armpits. I then turned the water back on to completely rinse off, and decided to give some extra attention to my buxom chest. Washing my sensitive breasts with the body wash and an extra soft facecloth that I found caused a number of strong, positively electric tingles to course through me and radiate all over my body.
When I got out of the shower, I gently covered myself in a lavender scented Victoria's Secret body lotion. I then grabbed two towels, one to wrap my hair in, and one to cover my lovely breasts in. After letting my hair set for a little bit, and sifting through the latest edition of “Cosmo,” with my beautiful smooth legs crossed in front of me, I took full advantage of the moment to caress and massage my thighs. I unraveled my hair from the towel, blow dried it while combing it the rest of the way, and heated and twisted the ends just a bit, so I would have some curls in the front and extra waves on the sides.

Back in my room, I took off the towel that was covering my breasts, and took a few more seconds to enjoy the incredible beauty that was staring back at me. I opened up my underwear drawer and picked out a very sexy looking pair of high-cut black bikini-style lace panties, and took my time drawing them up my exceptionally smooth legs. They totally show off my thighs! I was very pleased that they sat perfectly on my curved hips and felt wonderful against my mound. I then picked out a matching lace bra, which I noticed was size 36C. I marvelled at how big I was relative to most of the other girls on the squad -even our captain, Christina. I then reached over to my collection of nylons and stockings, and picked out a pair of sheer suntan pantyhose to wear.

I then took a beautifully sewn and embroidered beige sweater dress out of my closet, and selected a pair of 4” black suede heels from what was clearly becoming a fast growing shoe collection to accompany it.
Putting the bra on over my breasts and using the mirror to clip the back was a wonderful feeling – almost like a wholeness I never knew that I was missing before. The nylons gliding up my smooth legs felt absolutely incredible. I was a little annoyed though that the dress made my hair just a bit frizzy, and had to fix that again! I adjusted everything into place, and was delighted that it came down to mid-thigh, and my shiny nylon covered legs were beautifully highlighted. I carefully slid on my heels, loving the feel of my nylon-clad feet slipping into them. As I stood up, I could see that the hemline of the dress was about 4” up from my knees. The sexy high heels made my legs look even more spectacular than what I saw earlier. My silky, nylon-clad legs were nicely toned, while also quite shapely and elegant looking.
I quickly moisturized my face, patted on some foundation, did some quick smoky eyeshadow, eyeliner, mascara, blush, and powder, and was just about to apply some lipstick when Mom called me.

“Renee, hurry up! You’re going to be late!” I looked down at the clock on my radio, and it was 7:20.

“OK Mom, I just need to finish my lipstick!”

I picked out a really nice shade of red to match my slightly vampy, ok for school, but not slutty, look. After finishing my makeup, I was a total goddess. I then spritzed on some slightly floral, almost spice accented perfume from a fancy looking bottle that said "Agent Provocateur" on it onto my neck, wrists, behind my knees, and onto my nylon covered ankles, and then took one last look at myself in the mirror while I smoothed my dress and tossed my hair back over my shoulders, which now cascaded to two thirds of the way down my spine.

I was blown away by the raving beauty that looked back at me, and started feeling a fluttering in my belly, tingles, and incredible warmth flow over me. Something like meeting the girl of my dreams for the first time, but it was actually me! I then grabbed my uniform out of my closet, slung my backpack on, and headed down the stairs, careful to take one dainty step at a time in my towering high heels.

The prettiest girl in my class, Christina Baldassare, was apparently my new best friend and was driving me to school today.
“Damn girl, you’re a complete knockout!” Christina looked impressed as she hugged me, and we kissed each other’s cheeks. “I think the rest of the team might get a little catty with you today.”

“No way - you’re like a total goddess…love those boots!” I responded, in a beautiful contralto voice that reminded me of Mom's, but a little bit fuller and deeper.

She was wearing a beautiful pink cashmere sweater, red plaid-pattered skirt, off-black pantyhose, and an expensive looking pair of knee-high stiletto heeled leather boots. I was a bit jealous after noticing what had to be a slightly higher heel than my shoes, and a slightly shorter skirt than the hemline of my dress. Instead of growing a woody, I felt blossoming warmth in between my legs, and a little wet spot started to form in my panties. We both exchanged a mischievous look and turned to make our exit.

Mom came over and kissed my head as I leaned down, now a bit taller than her in my heels, and warned me not to forget my pocketbook after I threw on my current boyish looking winter jacket, which seemed a bit out of place with everything else I wore.
“OMG Duh!”

I grabbed it off the kitchen chair it was hanging on and reflexively opened it. I noted that I now had my own makeup kit and lipstick, in addition to my keys and wallet in there. And right behind my wallet was, Omigod, TAMPONS!

"Mom looked at me with a beaming smile, and said "you're gorgeous Hunny Bunny. Knock ‘em dead!"

I have her a big hug and said "Love you Momma," as I blew her a kiss, and closed the door that connected our kitchen to the garage behind me.

As we were heading out, I listened to the sound of our heels clicking against our garage floor and then our driveway. I could then feel the warmth of the sun on my face and lips, a breeze gently massage and tickle my hosed legs, and my breasts bouncing up and down as I walked with immense confidence. I felt utterly amazing. I could hear that 80s song "Ain't Nothin Gonna Break my Stride" playing in the background.
We walked together to Christina’s Jeep, briefly holding hands, and then I opened up the passenger door after loading my things into the back. As I carefully sat in the car sideways and slid my legs around to avoid exposing myself under my dress, we both turned and stared at each other for about thirty seconds, and then kissed! The wet spot between my legs was spreading across my bottom, and I felt all the feelings from yesterday evening return as we probed each other with our tongues, and our breasts touched for few explosive seconds. As the wetness and warmth between my legs spread out from under me and Christina let her delicate hands roam around on my back, I suddenly woke up after I broke away for a brief second to pull the door of her Jeep closed – I was a hot, wet mess, and couldn’t believe what I was just dreaming about.
Apparently during my dream I had a “nocturnal emission,” and needed to get that taken care of.

“What in the world was happening to me? Am I turning into a girl? My name was Renee? This is so weird,” I thought to myself as I got out of bed and headed to the bathroom. I felt a bit chilly, and shivered; and was suddenly reminded of what I was wearing as I felt the silky material swish around my chest and the tops of my thighs. After I got my panties off, I decided to sit down to pee before cleaning myself up the rest of the way. When I pulled up my panties, I instinctively tucked myself away so I could see more of the girl from my dream when I looked back in the very same mirror before showering. I “catwalked” down the hall back to my room, swaying my hips every step of the way while barefoot, just like I did earlier in the high heels.

All of these sensations were very confusing, but also strangely pleasurable. I wondered where this was all heading as I fell back asleep. As I would eventually discover, I was being welcomed into a wonderful new world of sensuality, where I could experience a far greater range of feelings and emotions than a typical guy would. I would get to enjoy a whole bunch of amazing “en femme” days and nights, seeing and being seen by the world as a beautiful woman - All of which would provide a delightfully rich, and incredibly fun, aspect to my life beyond anything I could have imagined at that tender young age.

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…

I developed a much closer bond with my Mom after our special “mother-daughter” time together.

On the following Sunday morning, I came downstairs early, knowing that she would be preparing a big breakfast while my father and younger brothers slept.

She was lost in thought and clearly surprised to see me so early, and I startled her a bit.

“Goodness!” She exclaimed. “Oh, Good morning, Honey Bunny!”

“Morning Mom…I was wondering if I could help you get everything ready for our breakfast this morning?”

“Wow Mikey, I would love to have a helper. Of course you can. Why don’t you start by peeling the Oranges?”

I had just clipped my fingernails, so Mom’s technique of using her nails wasn’t going to work.

I then decided to go get my Swiss Army knife that Dad bought me for my birthday last year to open them up.

“Good thinking my boy!”

“Thanks Mom!”

As I peeled the oranges and thought about the whirlwind of feelings, emotions, and incredible fun I had just experienced, I decided to ask Mom some questions.

“Mom, where did you put all those girl clothes you bought for me?”

“In one of my steamer trunks, why?”

“Well, I really enjoyed wearing all the different styles of clothes, and I was wondering if we could do a fashion show again sometime.”

“I really enjoyed our special time together too, Honey.” Mom then leaned over from the sizzling bacon pan to kiss my head.

“It was a lot of fun for me to take you shopping and have a nice night together, just the two of us. I have always wanted to do something like that, it made me so happy!”

“It made me really happy too, Mom.”

Mom looked back at me with a huge smile.

“Sure thing Honey Bunny. And any time you want to get into your special clothes, all you have to do is ask.”

“I would really like to do it again soon. The silky nylons and everything was so different from my usual clothes. The cashmere was especially soft, and made me feel all kinds of amazing things.”

“Oh I understand, at your age your tactile senses are really in full swing.”

“What’s tactile mean?”

“It’s your sense of touch. Yours are apparently highly attuned. It’s a very special gift to have!”

“Wow, awesome! Mom, what if I turn into a girl?”

My mother burst out laughing hysterically.

“Mikey dear, wearing different clothes is not going to interfere with what Mother Nature has already set in motion. You’re going to grow into a strong man, just like your Father. And the fact that you enjoyed the look and feel of everything you wore simply means you now have an appreciation for us ladies that you wouldn’t have otherwise had. I’m so proud of you for being courageous enough to overcome so many negative stereotypes about women and girls, and deliver an outstanding report about Annie Oakley. Miss Russo gave you an A+!”
I thought about that a bit.

“Can we still do mother-daughter time if I grow bigger?”

“Of course Honey. I want you to always be happy with who you are. No matter what, you’ll always be my baby boy…except for when we pretend you’re also my baby girl too,” as she giggled and teased my hair.

As we finished preparing our breakfast, I loved my mother more than ever, and gazed at her with a feeling of incredible admiration.
I continued to enjoy dressing up in everything she bought me as long as I could, until my freshman year of High School, when I outgrew the last of my skirts. It was October, Halloween was rolling around, and a few of my friends decided to do something totally crazy: Dress up as cheerleaders! More shopping trips, and more than a few shenanigans, were in the cards…but that’s for next time.

“Fin”