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!