Chapter 21 — Getting Ready

 

When the afternoon before the big day came, I arrived home to find the usual hot bath waiting and I just resigned myself to make it through the next thirty hours. While in the bathtub, Mom brought in a razor and shaving cream, telling me that she was going to remove the fuzz from my legs and underarms, not that I had any to begin with. By the time she was finished, both my legs were satin smooth and Mom said that was necessary because tomorrow, I wouldn’t be wearing any stockings with my outfit.

I dried and went to my room to find my usual bra, panties, and girdle waiting for me on the bed. After putting them on, I asked Mom what else to wear and she said whatever I felt like, except she wanted me in the red high heeled sandals. So I put on a white pullover and a pair of red print capris, put on my face and went to find her in the kitchen ironing what turned out to be my costume. The top was a red polka dot sleeveless blouse that had ties in front for the front just under the bust line, thereby bearing the midriff. To my relief there was no skirt; instead, I saw a pair of cutoff denims made into short-shorts with loose threads. The outfit was what Mom felt Sadie herself might have been wearing that day in cartoon history when she went chasing off after a husband.

Mom put down the iron and draped the top over a hanger already sporting the full cupped bra that I’d be wearing. "You look very nice," she commented. "Get your purse and let’s go."

I didn’t know exactly wear we were headed, but I can’t say I was really surprised when we pulled up in front of the place where I’d gotten my hair done earlier in the summer. When we walked in the front it was obvious that Phyllis was expecting us. She gave me a big smile and complemented me on my appearance remarking that I had grown even cuter than last time she’d seen me. I was directed to sit in her chair and make myself comfortable.

"Oh, Gregory, I’m just so thrilled that you agreed to let me work on you for your special day tomorrow," she started. "You’ve taken such good care with your hair and it looks so long and pretty, I promise you won’t be disappointed with the results." I wasn’t really sure what she was talking about, but I suspected that Mom had given her instructions on what she wanted done. I was just going to grin and bear it until it was over.

She started by wetting down my hair and then combing it down from a part in the center of my scalp. With the front combed forward down covering my face, she began trimming across at the level of my eyes. "Don’t worry," she consoled me, "With the proper amount of curl, your bangs will hang well above your eyes." Good grief; curls no less.

When she was done trimming, I was subjected to the expected shampoo and then told that she was adding some tint to "bring out my natural highlights." What followed was my hair being systematically segmented into strands that were then wound on rollers, which in turn were secured tightly against my scalp with bobby pins. Setting lotion was applied with its ever so pungent odor and a drier was lowered in place and set on hot-high. The accompanying roar of the drier effectively drown out any further conversation.

Next came attention to my nails. They were washed, brushed and soaked. Following that, nail extensions were glued in place and allowed time to set before being coated with bright red lacquer. If I’d thought that my nails were obvious with red polish earlier that summer, these by comparison were now like flashing neon signs. My sandals were removed so that my toenails could receive the same treatment. With cotton balls separating the toes while the polish dried, I looked down and understood why Mom had chosen the open toed design for my heels. Even while just wearing the capris, super sexy was the signal they were broadcasting.

My face burned as I realized I was getting an erection from just looking at my feet. Talk about being confused!

I hadn’t expected what came next, but Phyllis then turned her attention to my eyebrows, telling me she was shaping them for a more refined look. When I finally got a look at them, I was relieved to see that at least they weren’t the extreme fine arch that I had feared. More of a well defined clean tapered appearance with somewhat of an angle near the center.

Finally the timer on the drier clicked off and the hood was removed. Phyllis removed the rollers and then brushed out the curls. I could feel her preening the bangs on my forehead and then she brushed the rest of my hair back into the familiar ponytail, only this one had a tight wave to the portion beyond a cinched red ribbon.

The final effect was devastating when she turned the mirror for me to see. Where was the boy who had started high school in September? Was there any trace of him left? None that I could find. I was looking at a pretty young girl instead.

When Mom and I left, she tipped Phyllis generously and complimented her on my marvelous transformation. As I was trying to buckle my sandals, I got my first taste of how restrictive my nail extensions were going to be. How on earth did anyone fasten such small buckles with my half inch protrusions jutting from their finger tips? My fumbling efforts finally paid off, but not before providing Mom and Phyllis with a pathetic source of amusement.

"Cheer up, love," Phyllis comforted. "You’re not the first young lady to find that it takes patience to master having pretty nails."

On the way to the car, the pavement echoes of my heels attracted my attention and looking down all I noticed that my nails now matched the color Mom had chosen for my sandals. Color coordinated toes, shoes and fingertips I thought. How feminine. As if reading my mind, Mom remarked that she had gotten me a fresh lipstick in the same color as my new nails to use tomorrow. I could add it to my collection.

For the rest of the evening, everything I did seemed to reinforce that fact that my hand movements could no longer be taken for granted. Picking up a paper clip or a piece of paper took on a whole new dimension. Holding my fork or pen required a totally different grip.

Touching my face or other sensitive areas required a special attention to gentleness, as I discovered when I went to the bathroom; wiping myself was an uncomfortable and humiliating ordeal, and I made sure to wash my hands extra good. (Yuck!) Afterward I wondered what would happen if I tried to masturbate; the very thought of those long nails against my tender skin gave me the shivers! Was this another little way Mom had of curbing my boyish appetites?

I finally understood Mom’s snide comment from what seemed a long time ago about managing my bra with nail extensions. It was like having to learn it all over again. At least she wasn’t there when I was struggling or I might have had to under go the on-off exercise I did when I was first introduced to the peculiarities of female undergarments.

Sleep that evening was another confused struggle between feelings of apprehension over appearing at school fully feminized and anticipation of an unwanted excitement I didn’t comprehend. More than once I awoke to the odd sensation of my newly exaggerated finger nails, only to be reminded that in the morning I’d being parading about in with bright red toe nails displayed atop four inch heeled sandals.

Suddenly Mom was gently shaking me awake and then I was jolted back to reality as I remembered where I was and the significance of the day.

"Come on, sleepyhead, time to rise and shine," she coaxed. "We’ve got a lot to do before you leave for school today and not a whole lot of time to do it."

I muttered something about feeling ill, but a quick look from my mother told me that probably wouldn’t be a good idea. The memory of what happened last time I tried faking being sick flickered in my mind, prompting me out of bed in record time.

"Start out by showering and then meet me in my room. Now off with you." She seemed in an unusually good mood for so early in the morning. I showered as usual except for the plastic cap I had to wear to protect my curled hair. I then returned to my room where she had laid out a pair of panties and a short panty girdle. I slipped on the panties and then tugged the latex garment up into place, leaving me girlishly flat in front.

When I got to her room, she gave me one of her frillier robes to put on and had me sit at her vanity table. She then proceeded to do my makeup in an overly elaborate fashion. First came a thick coat of pancake, then the rouge, followed by blush, plum colored eye shadow and dark eyeliner. I was told to do my own lipstick and mascara. I used my new tube of red lipstick and applied it as I had been taught.

"I want you to keep it looking fresh throughout the day," she said. "I’ll know if you do or not, but you won’t know how."

Then she brushed and teased my hair until it was a mass of curled bangs in the front and a tight ponytail at the rear of my head. I could watch as she worked, and the look she created was not of an innocent fourteen year old boy, but of a mature teenaged girl, teetering on the edge of womanhood, on the prowl. I was definitely going to be attracting attention.

My mother produced a pair of very large gold hoop earrings — a pair that I'd never seen before — and secured them to my earlobes. I couldn’t believe the added heaviness compared to the light gold hoops I had worn up until then. They felt like they weighed a ton and I knew that they were going to be a constant distraction all day. With each turn of my head I could feel not only the tug on my lobes, but their light brush against my face. It also occurred to me that it was suddenly going to be obvious to everyone who saw me that I had my ears pierced. There was no way to pretend I was wearing Mom’s clip-ons.

My fairy pendent was secured about my neck and Mom gave me some gaudy bracelets to slip over my wrists. They were loose and tended to fall over my hands when I dropped them by my side. "Keep your hands higher than your wrists and you won’t have any problems," Mom coached. She didn’t add that holding them such caused me to assume a naturally feminine posture, which made me feel stupid. I figured that once I left the house, I could just push them up my forearms but I found later that they didn’t want to stay there, sliding right back down over my hands. I decided that once I was out of the house I’d stash the unwanted bangles in my purse.

Next I was allowed to don my bra. Mom watched proudly as I slid out of my gown and into my new brassiere, stopping me just long enough to examine my pudgy breasts. "Very nice," she said, her expression one of delight. "It looks like they are still growing, doesn’t it? Imagine that."

I shrugged my shoulders. She was right; ever since summer they’d grown considerably, for whatever reason. By this time I could almost cup one in each hand. Of course, this wasn’t something I was particularly proud of and I didn't feel much like talking about it. Anyway, with my bra in place and pulling my breasts together I appeared to have a rather noticeable valley above the supported mounds now decorating my chest.

Then Mom handed me the top and showed me how to tie the loose ends under my bust. The shoulder straps were not very wide and I began to worry that they wouldn’t conceal my bra straps. Mom wasn’t very reassuring, saying that I should check from time to time to see that my straps were concealed beneath my blouse. I hated wearing sleeveless tops and to say I felt exposed was an understatement.

The cutoff jeans Mom handed me didn’t cover much either. These were extremely tight, cut from a pair of hip huggers at least a size too small for me. When I finally got them buttoned up the front I was worried when I saw how much of my belly button and my midriff were exposed. With the low waistband they barely covered the top of my panty girdle, and they were so short that I had to poke and tug to keep the white lace and elastic from being seen through the leg holes. My smoothly shaven legs ran a long way down until they came to my feet with the bright red toenails.

Putting on the red high-heeled sandals remained a struggle as I still hadn’t adapted to the long fingernails. Between my manicure and the constricting girdle it was a challenge, but I finally got them buckled. When I stood up I was chagrined to find that the top button of my shorts had popped open. It took me a minute to refasten it and I realized that I was going to have to be careful if I didn't want to embarrass myself when I got to school.

When I finally looked in the mirror, the reflection was such a shock it nearly took my breath away. There I was, the picture of a seductive young woman, made-up and dressed to go on the hunt for a man. But instead, I was heading off to school where I would be seen in my feminine glory by all of my friends.

As if all that wasn't bad enough, I started getting an erection. The image before me was so sexy, so powerful, I couldn't help squirming. Oh god! I remember thinking to myself. I'm never going to live this down! I'll be lucky if I don't get the crap kicked out of me before the day's over.

I was thinking about crawling back into bed when I saw Mom coming up behind me. An unwelcome tingling sensation shot through my body as I felt and smelled the perfume she was dabbing behind my ears.

"Give me your wrists," she said and proceed to place some there also. "You’re going to smell like a lady today, also."

I shivered as the cool mist was sprayed between my breasts and behind my knees. I prayed my arousal wasn't noticeable; that would be the end of me for sure! I guess I shouldn't have been surprised when Mom gave me that knowing look of hers and grinned. "What's the matter, sweetie? Got ants in your panties?"

We went into the kitchen and I ate breakfast, noticing for the first time just how "in the way" my new bosom was going to be. Suddenly I was helpless to keep the milk that spilled from my spoon from dripping onto my clothes. Bending forward was a futile ploy. My breasts remained in the target zone. Special care in eating was going to be required or my top would have more than just polka dots spotting it.

"Greg's got boobies, Greg's got boobies," Dave said more than once. Mom shushed him, saying that little boys didn't say "boobies." I didn't mind that as much as I that idiotic giggle he made every time he looked at me. I couldn't say much, though; I would have done even worse if he had been the one Mom was torturing.

I was already dreading my fate when it came time to leave. Mom handed me my purse along with my books, wishing me a pleasant day. She smiled and gave me a kiss on the cheek.

"Oh, ‘Pamela,’ you look so lovely." Her eyes gleamed with, well, I wasn’t so sure it was happiness as much as it was mischief. I thought about giving her a kiss back, but I didn’t want to smudge my lipstick and have to reapply it. And with that I was out the door and on my way to the corner, my heels clicking with each step, earrings dangling stiffly from my ears and leaving a trail of syrupy aroma in my wake.

In my hurry to just get out of the house, I hadn’t calculated that I was going to have extra time standing alone waiting for the bus. There I was, loitering at the corner, bedecked in this outrageous attire. In addition, autumn had arrived, making for a chilly day; and there I stood with short-shorts and a bare midriff and naked shoulders when I should have been wearing long pants and a coat. Nonetheless, I think I shivered as much from anxiety as from the cold air. If it hadn’t been for my holding schoolbooks and the time of day, I feared I would be mistaken for a lady of the evening. The ten minutes I waited seemed like an hour. And then I caught sight of the yellow bus turning the corner four blocks away and heading toward me.

 

Chapter 22 — The Ordeal

 

When the bus door opened, I negotiated the steps carefully in my heels and looked around to see if anyone else was participating in the spirit of the day. Thankfully there were other kids also dressed for the occasion and it really didn’t make much difference to me right then if they were boys or girls. At least I wasn’t going to be made a total fool standing out alone at school. Still, I had to endure a gauntlet of smiling faces and whistles as I looked for somewhere to sit. I made my way down the aisle and took a seat next to Kathy Wade, one of the girls I’d known since junior high. I gave her a furtive smile.

"My mother’s idea," I said in answer to what I knew must have been her unspoken question.

"Very nice. You make a very convincing girl," she came back as she returned my smile. I was startled as she leaned close and sniffed carefully. "And you smell the part too. This must have really taken some doing. I’m impressed." Her tone wasn’t sarcastic but more of fascination or curiosity.

A polite "Thank you" was all I could return.

"So how do you like having to wear all this stuff?" she continued, not letting me off the hook.

"Well, as I said, it was my mother’s idea to have me dress up for Sadie Hawkins. I guess she went a little overboard."

She ran her fingertips over the tops of my thigh, sending a familiar shiver through my boyish region. "A little overboard, huh? Permed hair, shaved legs … pierced ears? You know, your ears don’t look like they were just pierced. Just how long have you been wearing earrings?" she pressed forward.

"My mom had them done last summer," I honestly admitted. I didn't know what else to say, so I just sat there with my sheepish grin.

My remarks were intended to divert her attention, but instead they seemed to whet her appetite. "And you seem to maneuver quite well in those heels as you got on the bus. You’ve worn heels before," she declared. It was a statement, not a question.

I told her that Mom made me wear them around home for the past week or so to get use to them. "I think she always wanted to see what I’d look like if I’d been born a girl and this was her big chance. She even had a name picked out. She likes to call me 'Pamela'." It was only part of the truth, but there was no way I was going to tell her the full story.

"Say, you got anything interesting in there?" She pointed to my purse. "I have to keep mine cleaned out weekly or I lose all kinds of things that I forget I even have."

"Only what my Mother has stocked in here for me," I replied.

"Mind if I take a peek? I’d love to see what she packed."

"Sure, help yourself." I handed her the maroon clutch that I’d been given to carry. I tried to remember what exactly I had in it, but it was too late

The first thing she found were the bangles I’d hidden away.

"You’re not going to wear these?" she asked.

I shrugged my shoulders. "They’re a pain. They keep falling off unless I hold my hands up like a fairy." I felt funny saying the word "fairy" while dressed as a girl, but as far as I was concerned, it was the truth.

Kathy gave me a curious look and then smiled. "Well, I think they’re neat. I can't believe you're not wearing them. Let’s see them on you."

I felt like I was putting on a pair of handcuffs as she slipped the collection of gaudy bracelets over my hands. She spent a moment or so arranging them and then made me hold my hands out so she could get a good look.

"See what I mean?" I dropped one hand and a bracelet almost fell off. I raised my hand back up in a girlish manner and rolled my eyes as I realized some of the other kids were watching.

Kathy shrugged her shoulders. "They don't look so bad. Why don’t you wear them? For me? Please?" Blushing deeply, I nodded. My new friend looked me straight in the eye, as though to challenge me. "Promise? Say you won’t take them off. I’ll know if you do, and then I’ll get upset."

"Okay, I promise," I finally said. A cold chill went through me. She sounded just like my mother. "I won’t take them off." I felt like an idiot as I held my hands up to keep the bracelets from falling off. I couldn't help noticing one of the girls across the aisle mocking me, holding her hands out in a limp-wristed fashion like she was gay or something, prompting her friend to giggle out loud. I felt like reneging on our deal, but faced with a smile like that, this was one promise that I would have to keep.

"You’re sweet," Kathy said with a wink. "Let’s see what else you have in here."

I felt my face turn red as my new friend produced the lipstick and mascara that my mom made me carry with me. She seemed especially impressed by the little bottle of perfume, saying that her mother had the same exact one sitting on her dresser at home.

"Do you do your own makeup?" she asked. I looked around to see if anyone was paying attention to us. The girls across the aisle giggled with delight, as were the two boys sitting behind us. The nod I gave could hardly be seen.

"I’d like to see that," my new friend said with a giggle. I heard the other children laughing in reply. She dug into my purse again. "Oh, my … look at this …."

Kathy’s face lit up. Her smile went from ear to ear as she carefully produced a familiar pink and white packet about the size of a candy wrapper. I blinked in disbelief as she waved the tampon under my nose. I grabbed at it, but she pulled away, her eyes wide with mischief.

"And just what do you think you’re doing with one of these? Do you even know what this thing is for?"

"Please, Kathy … somebody might see." I tried to contain my concern, but it was difficult considering the circumstances. The giggling around us turned to laughter, and my mouth went dry as cotton.

"Answer my question. Do you know what this is for?"

My face burning with shame, I lowered my eyes and nodded. Kathy nudged me in the ribs. "You do know what it’s for, don’t you? Did your mom tell you, or did you find out about it on your own?"

"Uh, my mom …." I could barely bring myself to say the words. "You know …. She told me all about it. I guess she put it in there as a joke."

"Sounds like you two are pretty close." Kathy looked at me carefully. "That’s neat."

When she finished searching through my purse Kathy handed it back to me, saying that it was practical inventory but not very imaginative. I took it back and wondered she thought I could be carrying.

She pushed forward with more questions. "Do you like the way you look, all decorated like a Christmas tree? Do your heels hurt? Did your mother shape you eyebrows, too? Well, what do you think of all that girls go through to look pretty? By the way, your bra strap is showing. Let me adjust it for you," she offered.

I shrugged my shoulders, blushing as her fingernails traced a line on my bare skin. "I guess it’s all right, dressing up like this, I mean. I’ll let you know when I figure it all out. But you’re a girl. How do you like having to spend all the time it takes to get ready every time you want to go out to some place nice?" I prayed that maybe I could turn the conversation back towards her and away from me.

"Sometimes it’s really neat. Other times it seems a hassle. But then that’s the advantage of being a girl. You get to choose. You know where girls’ choices are more restricted? It’s when it comes to asking boys out on dates. Girls normally aren’t supposed to do that, are they? But today’s an exception, isn’t it?"

To make a long story short, Kathy’s fascination with my appearance caused her to ask me if I had a date for the dance that evening. I couldn’t believe it!

She was actually asking me out!!!

I didn’t know what to say. I'd never been on a date before and I was torn. On any other day I would have felt like the luckiet guy in the world. But … well, shoot … I was wearing a panties and a bra!!! How do you think I felt? On top of that, I was more than a little worried about what my mom would think when she found out. Taking the conservative route, I tried to act cool about the whole situation.

"Well, I’d love to go with you, but I have to check with my mother first to make sure she can drive. Let me have your phone number and I’ll call you and let you know. If she says ‘yes’ then you can give me directions to your home."

Looking the way I did, I couldn’t believe a girl would actually be interested in asking me for a date. Especially not with me looking like some sort of fruitcake. But Kathy had. And from the look she kept giving me, she was more than interested in what she saw.

"Don’t worry about having to pick me up. My mother can drive if your’s can’t. But I must admit," she confided, "I really want to meet your mother."

Call me paranoid, but instead of being elated that I’d been asked out, I was immediately wondering if she really had an ulterior motive. What did she mean about meeting my mother? Why would she want to meet her? Was there something about my dilemma that excited her? I could only speculate, which even caused me further worry.

The bus was pulling into the school turn-around and I had her number copied into my folder. We were picking up our books and binders when her parting comment left me speculating all the more.

"Now be sure you come as ‘Pamela’," she advised. "You promise?"

I wasn’t sure I heard her right. I made a face and swallowed. "Uh … as ‘Pamela’? Y-you want me to come to the party … dressed as a girl?"

My new friend nodded. "Absolutely! I think it’ll be fun. Remember, it's the Sadie Hawkins dance, so there’ll be other guys dressed up, too, right? So why not?"

I squirmed in my seat. My girdle was already killing me, adding to the discomfort of our conversation. "Ummm, no reason, I guess."

Kathy seemed to enjoy my confusion. She blew me a kiss and then winked. "Great! Then it’s a date! Don’t forget, ‘Pamela,’ all right? I want my little brother to meet her. It'll be lots of fun!"

Well, perhaps this has something to do with her little brother instead of me, I thought.

Once at school, I was relieved to see that besides girls, there were several other boys dressed for the day. Way less than half of the boys decided to join in, but it was better than nothing. You could divide them into two general groups. The vast majority were mere parodies of girls, and then there were those who actually could have passed as real misses. The first group had hairy legs showing beneath their nylons, grossly over-stuffed brassieres, garish makeup and were acting loud and obnoxious. Some just had makeup and a scarf on, the cowards.

The second bunch of boys, a much, much smaller group and the one to which I obviously belonged, looked rather feminine, acted demure, and presented a more quiet comportment. I made a mental note of who these boy-girls were, thinking that in some way I shared a common bond with them. I knew that I would eventually want to ask them what had led them to this point. If only I made it through this day.

Needless to say, my mother’s costume design attracted a good deal of attention. More than one girl complemented me on my appearance and commented on either my hair, smooth legs, nails or how well I managed in my high heels. Several seemed amused by the attention to detail in my costume, making sure to tease me about things like wearing a bra and having my hair permed.

The guys were another story. Those who didn't know me gave me a careful look and a smile and went on about their business. If they thought I was a boy they didn’t make a big deal about it, just a curious grin, a remark and that was about it. Those who knew I was a boy had to look at me twice to make sure of what they were seeing, and some of the comments weren’t very nice.

"Wow, Parker, you look really hot!" one of the more rambunctious guys commented just before our first class. Todd Haggarty and his friends had refused to dress up for the day, and they’d been harassing several of the younger ones who had. "Not bad for a little faggot. Maybe if you’re nice to me I’ll get you a date with one of the guys on the football team. I’ll tell’em you’re my little sister so they won’t be too rough on ya."

"That won’t fly, dude," another boy shouted. "He’s too pretty to be your sister! Damn, that little fairy looks better than most of the real girls in this class!"

That got a laugh all around the room. Even from the girls. I felt the color rise in my face, but I said nothing. Trapped in my prissy costume, all I could hope to do was get through the next few minutes.

Todd stepped up close to me and flicked my fairy pendant with his finger. "Fairy boy! That's a good one! That's what we'll call you … Fairy Boy! Where'd you get the pretty necklace from, fairy? From your mama?" He then elbowed me pretty hard, knocking my textbooks on the ground. "Uh-oh, Fairy Boy … you dropped somethin'. Better pick it up."

 

Without saying a word, I knelt down and gingerly picked up my books. With my high heels and the skimpy top and skintight shorts, I had to be extra careful not to tip over and fall flat on my face.

 

Several of the boys hooted and made rude noises. "Did you see that? He even squats like a girl! Man, what a little queer!"

I could feel the tears welling up in my eyes, but I was determined not to cry. I knew from the very start that this kind of thing was going to happen. It was inevitable. As angry and frustrated as I was, I really couldn't blame the guys; I'd have probably done the same thing in their shoes. It was probably a good idea to keep my mouth shut, being that I wouldn’t have stood a chance against any of the bigger boys, even without my high heels and delicate clothes to impede me; with my nails so long I couldn't even make a fist! But that didn’t make things any easier.

All day long I had to endure similar whispers behind my back. Most everyone either ignored me, thinking I was either just another girl or assuming I was really into the spirit of Sadie Hawkins Day. But all it took to make me miserable were those one or two bullies. I don’t know which hurt worse, being called "fairy" in front of my classmates or having my ponytail pulled and my earrings flicked by some jerk every time our teacher turned her back.

Mom would just love this, I remember thinking to myself at one point. "That's what you get for being such a stupid boy," she'd say if she could see me now….

Aside from the occasional teasing and bullying, I had other problems, too. Throughout the day I was constantly reminded of how restrictive my nails had become as I had to adapt a whole new technique of managing myself. In addition to writing and turning pages in my textbooks and manipulating the combination lock on my locker, I had to worry about little things like poking myself in the eye whenever I scratched my face. Small objects continued to present a challenge and I found that lightly rapping my nails on the wooden desktops provided an entertaining new sensation.

By lunchtime I was exhausted. Between keeping my hands bent up at the wrists to prevent losing my bangles and balancing myself in my high heels, I was worn to a frazzle! I was so tired, in fact, that I didn't bother eating. To make matters worse, my stupid shorts kept coming undone at the waist and I was afraid if I did eat anything I'd never be able to fasten them back. Instead, I opted to drink a carton of milk and share part of a dessert with one of the girls I had classes with. Leslie thought my predicament was hilarious, and she enjoyed hearing me complain about my tight shorts and my feet.

"Now you know what we girls have to go through, girlie-girl," my friend teased cruelly. "Having to watch your girlish figure and tripping around in high heels! Oh, Greg, you look so ridiculous with those silly breasts … they're almost as big as my sister's! Imagine if you had to wear a skirt and had to worry about showing your undies. Now that would have been really funny!"

This went on for the entire lunch period. Leslie had her reasons for being mean, I guess, since I'd given her a hard time when she'd first developed her figure. More than once I'd teased her about her boobs and snapped her bra. And now she was having more than her share of fun at my expense!

I was in too much pain to worry about such things, anyway. I had to go to the bathroom something terrible, but I didn't dare, not dressed the way I was! Going to the boy's toilet in such a feminine outfit would have just been asking for trouble; it was bad enough getting stared at in the hallway, I didn't dare imagine what someone would say if they saw my red toenails and those gaudy high heels peeking out from underneath a stall door. And slipping into the girls' restroom was definitely out of the question. As a result, I just had to hold it in until I got home, no matter how miserable I got. And believe me, that was pretty miserable!

My clothes continued giving me fits throughout the rest of the day. Even with my panty girdle on my shorts were so painfully tight I ended up leaving the top button unfastened. Fortunately no one seemed to notice it. What a relief that was! I just had to make sure nothing else came undone!

Then there were those stupid sandals. What a pain they turned out to be! I would have been slipping off my heels off each time I wasn’t standing if I could only have unbuckled those tiny clasps with a little more dexterity. By fifth period, my feet were killing me and at the risk of not being able to get them back on, I had to get out of those shoes. Beneath my desk I kept one foot in one sandal, held the other sandal in one hand and used my free hand to massage my aching foot. Then I’d slide my sandal back on and duplicate the operation for the opposite foot. At the end of that period I managed to refasten the buckles and make it the final assembly of the day. Finally, the end was nearing!

Unfortunately I had one final hurtle to overcome. During the last hour the entire school gathered in the auditorium for announcements and awards. We were supposed to be grouped with our home rooms, so I had to watch carefully to make sure I didn't sit anywhere near any of the boys who'd been teasing me earlier in the day; I was near the breaking point and another flick of the ear or getting tripped or pushed one more time would have surely set me off on a crying binge. I made a point to sit next to a couple of the student teachers who'd looked at my cross-dressing adventure with smiles and kind words.

I was pretty much in a daydream as the assembly got underway. I remember thinking about all I'd been through that day and how I was going to answer Mom when she quizzed me on my experience. I contemplated lying to her and saying "Oh, nothing," when she asked me how things had gone, but I knew I'd end up telling her everything. I always did. When I got home she was definitely going to have a field day at my expense. It wasn't something I was looking forward to.

Next thing I knew, a dozen hands were poking at me and one of my teachers was pushing me out of my seat, saying, "Come on, prettyboy … they're calling your name." Looking up, I realized that the principal of the school was pointing at me from where he stood on stage, just like the host of a television game show.

Oh, god … now what? Oh, no-o-o-o-o-o-o …!

As I made my way up to the front of the auditorium I realized in horror what was going on. There were at least four other kids on stage, all dressed up in country girl costumes. Apparently I'd been nominated for the Sadie Hawkins lookalike contest and didn't even know it! I glanced back at the kids in my homeroom and saw Leslie and Mark and some of the others waving and blowing kisses at me. I later found out that they'd all gotten together and convinced Miss Allen, our teacher, to put my name up for grabs. Miss Allen apparently found my predicament about as entertaining as did my so-called friends.

I don't remember much of what actually happened on stage. I do remember standing there like an idiot in front of more than two thousand kids, trying to act like wearing lipstick, heels and earrings was the most natural thing in the world for me to be doing. I was so nervous I dropped my purse at least twice, and I was so self conscious when I stooped to pick it up; a wave of giggles swept across the auditorium each time and I could just imagine that Todd and his gang were having a field day saying nasty things about me!

There were two other boys among the finalists, thank goodness, one a senior football jock wearing a potato sack over his jeans and a straw hat with a plastic flower and a tacky makeup job, making him the hit of the event. There was another boy, looking rather feminine sophomore in an old-fashioned country-style dress, his hair and makeup giving him a definite girlish appearance. Of the two girls on stage, one was a junior with a pair of funny glasses and had a tooth blacked out, while the other, a senior, looked like she stepped right out of a fashion magazine, clad in a skimpy top and short shorts almost identical to my own. If I wasn't so miserable I might have thought the whole thing interesting and fun.

And then there was little old freshman me. My name was called — my boy name, of course! — and I minced out to the podium and stood there grinning like an idiot. The principal was savvy enough to know what was going on and he played up my girlish appearance while acting as though he didn't know I was a boy. I do remember him winking at me as I thanked him for calling me up on stage (Yeah, right!) and then dipped slightly at the knee. My girlish actions set off another wave of giggles, and I fought the desire to kick off my high heels and run off the stage.

In spite of the applause and laughter I garnered from the audience, I didn't win, thank goodness. The fashion model came in first while the jock won second place. The girl with the glasses and missing teeth came in third. I placed fourth, though, which was enough to set of a wave of laughter and wolf whistles among my classmates when I stepped forward to accept the little trophy I'd won. The shy sophomore boy came in fifth, by the way. Funny, I thought he looked rather cute, but hardly anybody applauded for him. Between you and me I sort of felt bad for him.

I was so glad when the final bell rang. Between having to go to the bathroom and all the teasing I'd endured, I was worn out and ready to go home. Unfortunately for me, two of the boys who'd harassed me at the beginning of the day just happened to catch me on the way to my bus.

I felt a chill down my spine as Todd and his partner, a tall black boy named Joe something-or-other, stepped along either side of me, as though they were walking me to the bus. Instead, however, the two ninth graders forced me into a dead end hallway, alone and far from the other kids.

Todd put his arm around my shoulders. It was a weird feeling as he put his mouth up to my ear; I felt sick as the warm air tickled the side of my neck. "Hello, Fairy Boy! How's it going, honey? You really looked good up on stage, sweetie-pie!" I clutched my books against my bosom, as though to protect myself.

Joe took his cue. He poked me in the side with his finger, just under the ribs, tracing a line all the way around to my bare belly button. "She sure did, man." I felt his fingertip travel up to the knot tied between my "breasts." Fighting panic, I bit my lip and stood perfectly still. "Did you notice, she even walks like a girl. Man, that's sad. I bet this little girl wears her high heels all the time. Shows off that little butt when she does."

Todd laughed a mean laugh. "Come on, faggot, tell us the truth. Do you wear high heels at home? You like showing off your little ass?" He was working on making me cry, and I knew he could do it, given enough time. "You want to show us your pretty ass, Fairy Boy? We won't tell anybody."

I decided to at least make an attempt at getting away. "C'mon, guys, it’s just a stupid costume. Please, let me go. I'm gonna miss my bus. Please ….?" I tried to step past my tormentors, but they were faster in their sneakers than I was in my high heels. Joe knocked my books and trophy out of my hands and gave me a hard look, daring me to pick them up. Todd reached around and grabbed my ponytail, laughing cruelly.

"You're not goin' anywhere, faggot! We want to see just how much of a girl you really are. We wanna see some more of that ass. I bet she’s wearing panties, right now, Joe! Whatchu think?"

"Hey, man, I think you're right. Look here." I winced as the smirking black boy pinched me on a tender spot just below my ribs and then slipped a thick, rough finger inside the waistband of my shorts. He tugged at where the top button had come undone and started fiddling with the next one. Closing my eyes in shame, I could feel it coming loose. I could also smell the aroma of his cologne. It reminded me of something I smelled at the barbershop. Funny, the things you remember when you're under stress.

Anyway, while I was praying for a miracle, Joe was busy tugging at my waistband. "C'mon, man. She's already popping out of them pants. Let's give her a hand."

I tried pulling away, but couldn’t for fear of my shorts coming undone. Tears welled up in my eyes and I was having trouble breathing. That really got Todd going. "The little fairy's cryin’, just like a little baby. Cool. Let’s see some more tears, you little faggot crybaby! Undo them shorts, Joe. Let's see some panties!"

Joe grinned really big. I felt his hand slide into the front of my shorts and I was about to cry out for help when a loud voice shouted out, "Hey, what are you three doing down there? Get out here and head for those busses. Come on, you know the policy. No loitering in the halls. Let's get a move on!"

It was, of all people, Mr. Landon, the vice-principal. He had a terrible reputation for a bad temper, but at that particular moment, I never was so happy to see his scowling face. I almost gave him a hug, I was so relieved! His expression told me he was in no mood for any more foolishness. He probably thought I was one of the boys' girlfriends or something. Not wanting to make a scene, I knelt quickly and grabbed my books and things, and then skittered along the tile floor toward my bus, my heels clip-clopping all the way to safety.

"Hey, pussy!" Todd hissed as I rushed away. "Don’t think you’re getting away with anything. You’ll get yours … I promise!"

A few minutes later I was climbing back up the steps of the bus that would deliver me home. I sat there in my lone seat, clutching my books close and hoping that Kathy would come sit next to me for the return ride; my biggest fear was that one of the meaner boys would try and give me a hard time all the way home. I was overjoyed as she appeared shortly after me and sat down next to me. Here I was, worn to the bones from my experience, desperate to go to the bathroom … and she was looking refreshed and energized in her white collared shirt and blue jeans, the choice of the day for most girls.

"I loved it when you were at the awards ceremony! That was so much fun … Can I see your trophy? Hey, what's the matter, sweetheart? Have you been crying? Your mascara's all smudged and stuff." The look on her face made me melt. I was so entranced, I almost forgot why I was upset.

"Um, I'm all right. Just had a long day," I said, my voice husky with emotion.

For the umpteenth time that day I remembered what Mom had said about keeping my makeup fresh and I figured that I’d better at least show up at home with my eyes done right and my lipstick freshened. Heaven knows what would happen if they weren't! I opened my purse to remove my compact and lip color and then proceeded to repair the afternoon's wear and tear. It didn’t go unnoticed by Kathy how I held the mirror and cap in one hand as I applied the lipstick with the other.

"You do that just like you’ve been doing it all your life," she joked. "Can I borrow your lipstick after you’re done? I didn’t bring any today and I can feel my lips getting chapped."

 

 

"Sure, here you go." I said as I handed it to her and pulled out a tissue to blot my own lips.

"I’ll need that too." She indicated as I started to return the tissue to my purse. She took it from me, blotted her lips and then stuffed it in her pocket. "Souvenir," she said with a smile.

I nodded. How humiliating, Kathy was using her pockets, while all I had was my purse.

"I missed wearing lipstick today," she commented. "Somehow I just feel kind of naked without it, but you probably wouldn’t understand that, would you?"

I just shrugged my shoulders and grinned sheepishly. I could feel Kathy watching me as I pulled out my mascara; I hated to put on a show in front of her like that, but I knew it wouldn’t do for me to face my mother with my eyes looking smeared and sloppy.

"Neat," Kathy said as she watched me touch up my eyelashes. "Most boys wouldn’t have the slightest idea how to do that. I wonder what else your mother taught you to do?"

I smiled mysteriously and put my makeup kit away.

When the bus came to my corner, I started to get up, but Kathy pulled me back by my arm and gave me a peck on the cheek. "See you tonight, sweetheart," she said. "Don’t forget. You’re coming as ‘Pamela,’ right?"

I nodded. "Sure. I mean, if that's what you want."

"That's what I want," she said with a smile worth dying for.

"'Bye, 'Pamela,'!" some of the other kids called out. Some of the boys whistled while the girls giggled. "Don’t forget your purse!"

Blushing warmly, I nodded, then made my way off the bus.

 

Continue on with Chapter 23 of "Lipstick Discipline"

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