Chapter 19 — Summertime Fun

 

Resigned to my fate, I tried to pretend the world of "Greg" was lost to me and I focused on pleasing my mother as best I could as "Pamela, my favorite daughter." It wasn't easy, though; there was a lot more at stake than just smiling prettily and doing housework.

For instance, I had to help redecorate my room, which consisted of putting most of my guy stuff in the attic, tossing the models on my desk and replacing them with jewelry boxes and perfume bottles, and adding the obligatory feminine bedsheets and covers.

I also had to force myself to not say a word when Mom took that ugly beefcake poster Rita gave me for my birthday and hung it up in my room. It really hurt to watch as my Atlanta Braves poster was torn down and thrown away, but even more alarming was the quartet of bare-bottomed musclemen on the wall opposite the foot of my bed, right where I'd see it before falling asleep every night. Mom thought it was hilariously funny, of course, and she made several snide remarks about this being payback for jerking off to my girlie magazines.

"Maybe now you know how disgusted that made me feel. Hiding pictures of half-naked girls under your mattress … you want to look at naked people? Then fine! We'll just leave that up and see how you like having 'the boys' keep you company for a while."

The smile on her face was evil. "Who knows, maybe you'll have more fun looking at them than you did with all those yucky girls."

I blushed as I remembered the dream I had … You can understand why I often thought that she could read my mind.

In addition to redecorating my room I also quit the ball team, which went practically unnoticed by the Coach. Between the scoldings and getting slapped around whenever I was late coming home, it just wasn't worth it. Then again, it wasn't easy, giving up baseball and fishing and running around with my friends for ironing and primping in front of my mom's vanity, but what choice did I have? Between my daily chores and my "lessons" and being confined to the house all the time, I was cut off from anything resembling boyish activity. Worse yet, my only forays to the outside world were our weekly mother-daughter outings and an occasional visit to the library.

While I hated being stuck in the house all summer, I had mixed emotions about "mother-daughter" day, which took place each and every Saturday. Mom would think up something fun to do — well, fun for her, at least — like driving across the city and seeing a movie or shopping or visiting a museum. Sometimes Dave would go with us, but most of the time he'd spend the day with a friend, leaving me at my mother's mercy.

With each trip Mom became even more bold, making sure I wore the prissiest outfits wherever we went and not caring who saw me: for example, the afternoon matinee or a shopping trip to the new mall called for a cute midriff top and a skirt and my hair tied up in "dog ears"; dinner at a fancy restaurant meant the aqua mini-dress and a mother of pearl hair clip decorating my locks; museums required me wearing that awful red suit, the one with the dress and jacket. Hose, heels, jewelry and purse were always prerequisite, of course.

My greatest fear, of course, was being seen by my classmates. Especially any of the guys I knew. I always figured if it ever happened it would be the end of the world. The very thought of all the humiliation and shame was absolutely unnerving ....

"What's the matter with you?" my mother fussed. "Get out of the car. For god's sake, girl, I don't want to stand here all day!" The car door was open and she was waiting impatiently for me to get out. The problem was that I couldn't.

"Please, Mom, don't make me do this. I look stupid. This dress ... it's awful. People are going to laugh." I tugged at my skirt and looked about for anyone who might recognize me. I glanced at the rearview mirror and saw my face painted with lipstick and mascara. It was going to be a long day.

"They will certainly laugh if they see me pull you over my knee and give you a good spanking," Mom said. Her face was dark with malice and her voice was growing loud enough to attract the attention of passersby. "Get out of that car right now before you make me angry! I'm not putting up with your foolishness, 'Pamela'!"

It turned out that most of the world couldn't have cared less that a boy in a dress visited the city museum that day. With my tresses parted in the middle and decorated with a silver hair band and my bangs fluffed out over my eyes, I looked pretty much like any of the other young girls wandering the halls with their parents. A little more dressed up, perhaps, in my bright red dress with its matching jacket, three inch white heels and matching purse. I thought my outfit was loud and obviously contrived, but Mom assured me that the color was fine, just perfect for her cute teenaged "daughter." The fact that she was similarly dressed in a cream colored suit, complete with hose and a white purse and heels just like mine made it all official: we were the perfect "Mother and Daughter" couple. Looking back I now realize that together that day we made a rather charming pair in our dressy ensembles; at the time, however, I was amazed at how people nodded and smiled at us as though we were looking to buy the place. It was all so very surreal, and I fought to keep from giggling out loud, I was so nervous.

I remember my lessons well and held my head high and my shoulders back, carefully taking short, mincing steps; to do otherwise in such a tight-fitting dress would have been impossible. Mom was so proud of how well I conducted myself, she literally glowed as she led me about, her arm locked around mine, chatting incessantly about the works of art scattered about as though I was her best girlfriend. Occasionally she would squeeze my shoulder or brush back my bangs, giving me a whisper of encouragement as she did so. In turn I would grin stupidly and pretend to listen as she went on about this portrait or that sculpture, but my thoughts were more focused on how uncomfortable I felt in my girlish disguise.

The practice I'd gotten from wearing dresses around the house came in handy as I managed myself without too much embarrassment; sitting and kneeling were my biggest challenges ... well, that and dealing with a pair of high heels that were a bit too tight. My main problem was feeling like I didn't have any pants on. Panties, girdle and hose are no substitute for a pair of good old jeans. I tried to keep from squirming, but it was difficult.

Then it happened. I'd gotten ahead of Mom and was just rounding a corner going from the major impressionist paintings to the main hall and a couple of boys came running the other way. One I recognized right away as being on one of the teams I'd played against earlier in the summer... the other I wasn't too sure about. Anyway, they were goofing around and stuff and the next thing I knew there was a collision and I was sitting on the floor. I was a sight , my purse twenty feet away in one direction, a lost high heel in another, and my dress all askew and mussed.

We hit so hard the wind was knocked out of me and for a few seconds I wasn't sure what had happened. When I finally did look up I saw one of the boys standing over me and the other sitting opposite me. Both were looking at me ... well, at my dress and where it had ridden high up above my knees. Confused, I just sat there, exposed underwear and all.

"Dang, sorry, 'bout that ...." The boy on the floor began. "Didn't mean to run ya down ...."

Before he could say anything else Mom lit into him like I'd never seen before. "You little hoodlum! I saw what you did, knocking my daughter down like that! You should be arrested, running in the museum like that." She looked around for a guard, rapping me on top of the head with her knuckles at the same time. "Knees together, 'Pamela.' No sense giving him a free show, too."

"Omigosh!" I clenched my legs tightly together. I had plenty to be worried about. It took me a second, but I quickly realized that I was showing off my slip and girdle to a couple of guys who would beat the crap out of me as soon as they figured out who I was. I wasn't sure if I was supposed to get up and run away, scream bloody murder or just sit there and hope to die a quick death.

Faced with the wrath of Mom, the standing boy looked down at my exposed undies, gave me a quick grin and then took off like a bullet. Imagine my confusion when the other boy — the one I knew from baseball — got up, dusted himself off, and then helped me to my feet. Apparently my mom was blocking his way, so he felt obliged to at least try and set things right.

"Here you go ... sorry about that ...." He gave a sheepish grin. "You're okay, right?"

It felt strange having him hold my hand like that, and even stranger as he used his free hand to press against the small of my back, right on my bra strap. His hand lingered there for a long time, but I was too speechless, too terrified to say anything. Why doesn't he start yelling and laughing? I kept thinking to myself. Can't he tell I'm a boy? Doesn't he recognize me? I thought about pulling away and hiding behind my mom's skirts, but that would have only made things worse. Besides, she was making a nasty enough scene as it was, and within a minute of the mishap the offender was gone ... but not forgotten.

Mom's reaction to our outing was nothing short of ecstatic. We were enjoying a treat at the museum café when she gloated over her latest success. "Now, see, 'Pamela,' isn't this fun? I knew you'd enjoy yourself if you just gave it a chance. I think we should do this more often, don't you, sweetie? Maybe next time we'll bring your brother. Won't that be nice?"

It was all I could do to keep from sinking into the floor and dying.

 

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While the trips to the city with my mom were nerve-wracking enough, going to the local library in a dress was the kind of thing that inspired nightmares. Funny, the first time it happened was my brother's fault. Dave had checked out some books and we got a call at the house saying they were long overdue. My brother was nowhere to be found, of course, so Mom pulled me from behind the ironing board and we drove over to turn them in.

"Here, take these to the librarian and give her this money for the fine. Be sure and get the change, all right? I'll wait out here in the car so we don't get a ticket."

I looked at my mother like she'd lost her mind. "Me? Go in? Like this? Mom, I can't go in there! Not dressed like this! Somebody will recognize me!"

That was a good possibility. The short white pleated skirt and the thin yellow "Barbie" top I wore while doing the household chores didn't look much like anything I'd ever worn into the library before. I was absolutely sure I'd never make it out alive; if any of my buddies saw me dressed like that, especially with my hair up in twin ponytails and ribbons and my face painted in my girlish makeup, I'd be forever branded in shame. None of that compared, of course, to the rigid look on my mother's face.

"You have a choice, 'Pamela,'" she said, her voice cold as ice. I winced as she reached over and gave a harsh tug on one of my ponytails. "You can either do this simple thing for me and make me happy, or I go cut a switch from that tree over there and wear out your bottom right here and now. Or maybe you'd rather I take you to the park where your friends are probably playing ball? I'm sure they'd love seeing you in your girlie clothes."

The tears in my eyes did nothing to move her. The next thing I knew, I was clip-clopping up the marble steps, books in hand, skirt tugged down about my legs. I remember taking a deep breath and shyly approaching the librarian help desk. Except for my voice squeaking from feeling so nervous, I managed to turn in my brother's books and pay his fine without causing a scene. The look on my mother's face as I click-clacked down the front steps belied how happy my little performance made her.

To make a long story short, this was the first of many such visits to the library. It turned out that very few, if any, of my regular friends wasted their time at the library during the summer. There were a handful of older teens, mostly summer school and college students doing research, but they had better things to do than bother with a teeny-bopper running around in training bra and ponytails. Realizing that the library was a fairly safe environment for me, Mom decided that I would make regular trips there, whether I liked it or not.

"I want you to go to the library this afternoon and get some things for me," my mom informed me one day at lunch. She'd finished up the chicken salad sandwich I'd fixed and was touching up her lipstick before going back to the clinic. She gestured to a piece of pink note paper on the dining room table. "Here's a list. There are a couple of textbooks I need, plus I've included some books I want you to read this week as well. Something to keep you out of trouble while I'm at work."

I brushed back a braided pigtail and fidgeted nervously. The flowery sundress I wore had been driving me crazy all morning with its short hem and skimpy design, and the little ribbons that hung from my short braids kept tickling my bare shoulders.

"This afternoon? Oh, Mom, can't I wait until this evening, when you get home? You can take me down after supper, can't you? I don't want to go by myself"

"Not tonight. The library closes early and I'm going to a Tupperware party. You'll have to go this afternoon. I can drop you off if you want a ride. The walk back will do you good."

I dropped my eyes for a moment and considered the bright silken material that covered my body. I never could get used to how my breasts made such interesting curves beneath the clothes my mother insisted I wear; I wasn't fat, she kept telling me, just pleasingly plump.

"Can I change clothes first? Please?"

Mom paused in her tracks, looking from her makeup mirror to me with an air of suspicion. "Absolutely not. Why do you want to do that? You look fine the way you are. I know what you're going to do. You think you can put on your boy clothes and go sneaking off with those idiots you call friends, that's what."

"No, Mom, that's not it. I promise, that's not it at all. I just don't want people seeing me dressed like this. Everyone's going to laugh at me."

My mother went back to her lipstick. "That's not my problem. You should have thought about stuff like that before you decided to become a liar and a pervert."

I remember feeling my face turn bright red. The very thought of going out in public in my new sundress was mortifying; going it alone was incomprehensible!

"Can't ... can't I at least wear some shorts, then? Or maybe my capris? This dress is awful ...." I struggled to think of the proper word.

"Oh, it's not awful, it's cute! That's what it is." Mom grinned as she finished up her lipstick. "You look very sweet in that dress, 'Pamela.' It's a shame you're just pretending to be a girl. I think you really fill it out quite well."

I looked down at the fairy pendant resting between my breasts and shivered. "But, Mom, please ...?"

"I won't hear another word about it. Now, touch up your lipstick and get your purse, girl. I'm due back at work in a few minutes. I've just enough time to drop you off."

The visit to the library that day was a traumatic event for me. I trembled with fear from the moment I stepped out of the car and began that perilous journey up those marble steps. Fighting to keep from crying, I managed to find my way inside the building and into an empty study cubicle in record time.

I hid in the cubicle for a little while, sitting and waiting for someone to come up to me and yell, "Why Greg Parker, what in the world are you doing in that dress?!!! What a cute little fairy you've become!"

That never happened, thank goodness. In fact, as I worked up enough nerve to venture out among the stacks I got more than my share of pleasant smiles and nods from several of the library patrons. A man from the library staff made a point to check on me quite often, which was actually very nice. I noticed that he treated me a lot better as "Pamela" than I was used to as "Greg."

My new grown up friend also took up the habit of putting his hand on my bare shoulder or on my arm and calling me "honey" every time he saw me. And a couple of times he even touched me on the knee, though he always acted as though that was an accident. And if being touched like that felt kind of weird, I really got the shivers when I saw how he kept looking at me from across the room. (When I mentioned all this to my mother that evening she said, "Get used to it, sweetie. Men do that kind of thing all the time." When I told her I didn't like it, she laughed for the longest time. From to look in her eyes I had a feeling I'd be spending a lot of time at the library that summer ….)

Anyway, back at the library it didn't take me long to find the things on my mother's list. Like she said, two of the titles were for her, some sort of psychology books, part of the night schooling she took to get a better job at the clinic. The others were a variety of girls' books; a Nancy Drew mystery, the classic novel "Little Women" and a teen romance novel that Rita apparently recommended. There was also a book on ballet, which got me to wondering if my mom might be thinking about making me take lessons. I certainly hoped not; my life was certainly complex enough!

When it came time to check out I discovered I had an embarrassing problem. My library card said "Greg Parker," not "Pamela." It took me several minutes of stammering and stuttering to explain that I must have gotten my brother's card by mistake. The librarian was very understanding, actually, and within minutes he set everything right.

I walked home in a daze. I couldn't believe it! Oblivious of the passing cars and the sounds of the other children playing along the street, I was trying to make sense of what happened. I don't know if it was the combination of being trapped in nail polish and a dress in full public view or the agony in my feet from walking such a long distance in a pair of ill-fitting high heels, or what ... all I knew was that I felt like I was drunk.

No ... yes, it was true, all right. In just a few seconds that kindly librarian made a huge, significant difference in my life. You see ... thanks to his efforts, as far as the public library system was concerned, my name was "Pamela." "Pamela Parker." Aged 14. Brown hair. Blue eyes. Currently residing on Crescent Avenue.

Just like it said on the little card with my picture on it!

 

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Probably the most shocking event for me that summer took place the day the Johnstons invited us over to swim in their pool. Wary that this might not be such a good idea, I whined and hinted and made all sorts of excuses why I should stay home. Mom, of course, wouldn't hear a word of it.

"I don't know what's gotten into you, but stop it! We are going to visit the Johnston's and we're going to have a nice time and you're going to like it! Do I make myself understood?"

To my horror, I quickly found myself heading for the front door, clad in little more than my new "Valentine's Day" bikini bathing suit and a pair of high heeled sandals. Oh, don't forget my newest purse and my daily application of lipstick and mascara. My mom sure didn't forget!

I felt like an idiot, of course. That stupid little bikini was about as modest as the bra and panties Mom made me put on every morning under my punishment clothes, only I was expected to wear this thing outside where everyone could see me. Granted, I didn't have the most masculine body, especially where my babyfat gave me curves in all the wrong places — for a boy, that is — and with my hair tied up in little bunches with brightly colored elastic scrunchies, I looked just exactly like a fourteen year old girl, or so my mom told me about a hundred times that morning. Needless to say, I was convinced that I looked more like a silly boy running around in girls' underwear! Nevertheless, I had my orders and I knew I'd catch hell if I didn't do as I was told.

Before we left the house I lost track of the times I stopped in front of the dressing mirror and stared at myself. As disgusted as I was with how I looked, I was also strangely fascinated. The top acted like a little push-up bra, gathering up my ever-swollen breasts and squeezing them together to give me a rather unboylike profile. A little heart pendant nestled in my cleavage only added to the illusion; I had to be careful not to touch myself for fear of getting caught.

The skimpy bikini bottom was just as bad; made of similar stuff as my panty girdle, it held me just as tight, hiding any sign of my poor privates under a flat elastic panel. The cut was rather sparse, the little triangle of hearts and lace leaving most of my abdomen exposed in the front and barely covering my cheeks in the rear; plus, the little strings that held it all together on the sides didn't exactly inspire confidence. I found myself constantly tugging the edges of the bikini panties over my bare bottom and checking the ties to make sure they didn't come loose.

Combined with my silly hairstyle, makeup and the hoop earrings Mom made me wear all the time, well, I guess I did look more like a girl than a boy. A girl about to burst out of her skimpy clothes, bashful and vulnerable and trembling with nerves. The fact that Rita had worn the suit before had not escaped me, and the very idea of being so close to her voluptuous body gave me so much pleasure it made my head hurt.

After about the tenth time in front of the mirror, I snuck into the bathroom and undid my bikini bottom and proceeded to masturbate. I knew I'd catch hell if my mother caught me, but I couldn't help it. I was so excited from looking at the little girl in the little heart-sprinkled bikini I was literally about to pop; seriously, if I hadn't done it I would have made a mess anyway and who knew what kind of trouble that would have gotten me. Don't ask me why things worked this way; even though I knew it was me, well, the figure in the mirror looked so cute, so helpless and so naked, I couldn't help myself. The orgasm that followed was so intense it hurt.

I quickly cleaned myself up and gathered my composure. When I emerged from the bathroom my mother gave me a funny look. She knew what I'd done — I could tell from the way her eyes pierced through me — but she didn't say anything outright. She just stared at me for a few minutes, smiled, and nodded.

"Come along, little boy," she finally said. "You can admire yourself some other time."

Following my mom out of the house, I felt so weird. It was like she expected me to react this way. I mean, the idea of a fourteen year old boy running around in bikini panties and a bra was completely laughable, and to be trapped in such a revealing thing was my worst nightmare. There was hardly anything for me to hide behind, which made the job of deception all that much more humiliating, and my mom knew that. Boy, did she ever! Either I looked like some fairy boy and would never able to face my friends for the rest of my life, or I'd look — and act! — like a proper young girl and never be able to face myself. I wasn't sure what I wanted except to get through the next few hours without making a complete fool of myself.

Just driving over to the Johnston's was a near disaster in itself. We hadn't been on the road for five minutes when the family car pulled into the local market. Mom had offered to bring lunch and there were snacks and drinks to be purchased. Grabbing my hand, she dragged me out of the car and inside we went.

I felt practically naked, walking about pushing a grocery cart while wearing that ridiculous bikini and carrying my little purse. I'd the foresight to put on my sunglasses, thinking that maybe that would make it at least a little harder for any of my friends to recognize me. All that did was draw even more attention to me. We weren't there two minutes when it became obvious that a couple of boys my age seemed taken with the image I presented. Mom pointed them out to me, her smile almost as unnerving as their gawking. I recognized both boys from school, one from a couple of classes I had. It didn't matter; it would only take one blabbermouth to ruin me forever.

As I minced about the store my audience watched my every move, not even trying to pretend they weren't. I stayed close to my mother in case they tried to speak to me. A lot of good that did.

"Don't I know you from school?" One admirer managed to maneuver himself between me and my mom. Great. It was Gary Lowe, the one I had class with. He looked me up and down and grinned with delight as he questioned me. "Didn't we have social studies together last year?"

I was so scared I could hardly speak. The truth was, we did have gym together, not social studies, but I certainly wasn't about to tell him that! I pulled my sunglasses snug against my face and forced a smile. "Um, I'm pretty sure we didn't," I managed to croak. "I'm just in the seventh grade," I lied.

"No way!" my friend said. "You look like you ought to be in high school!"

To my shame, his eyes were all over me , like invisible fingers, curious and bold. I thought about what my mom had said about boys and the thoughts that went through their minds when they saw a pretty girl. The way he fidgeted about made me uncomfortable, and I wondered if he was going to jerk off later that evening while thinking of me.

What do I care? I wondered. The images in my mind disgusted me as much as they roused my curiosity. Do real girls think about this kind of stuff?

Confused and panic-stricken, I wanted to cry out for help, but Mom just stood by and ignored the situation, leaving me to fend for myself. She really seemed to enjoy my misery. I squirmed and stammered through a largely one-sided conversation for at least ten minutes while she stood nearby thumbed through a fashion magazine and studied the cosmetics.

The one thing I remember was how both boys focused their eyes somewhere between my breasts and my bikini bottom, only looking me in the eye occasionally; oh, how I hated that! I fumbled with my purse and tugged at my earrings to keep from punching them both in the nose! By the time my admirers left I'd nearly broken out in a rash, I was so upset. Mom, on the other hand, was nothing but smiles.

"You really had that one boy eating out of your hand, girlfriend!" Mom teased as we stood in the checkout line. "I think that shy little 'Miss Priss' act you do so well really caught his attention."

"It's not an act! It was horrible! Oh, Mom, please, don't make me do that again. I was terrified he'd figure out I was a boy."

"Is he anyone you know?"

"Ummm ... he was in one of my classes last year. I thought for sure he was going to recognize me."

My mom grinned. "But he didn't, did he? Imagine that. I wonder why?"

"I don't know!" I fidgeted between crossing my arms over my breasts and holding my hands together in front of my privates; either way was inadequate, and standing around like that in the middle of the supermarket only made me feel even that much more exposed.

"I didn't like the way he was looking at me. Didn't you see him? It was like I didn't have any clothes on."

Mom gave me a harsh pinch under my arm and laughed. "Well, what do you expect, princess? Boys only have one thing on their minds. You, of all people, should know that. I just want you to know what it's like being on the other side, so get used to it, sweetie."

I wasn't sure what upset me worse, the way I'd been treated by that boy or the delight my mother was taking in that whole situation.

When we arrived at the Johnston's Mom put me to work right away, fixing the food and serving drinks. Rita and her mom seemed quite impressed, I think, the way I dove into my chores, fixing cups of ice and pouring lemonade and preparing the pimento cheese sandwiches. Mrs. Johnston laughingly referred to me as her "slave for a day."

"Too bad you won't come over and help out around the house more often," she said. "Having such a pretty child around really lights up everything! You'd make a wonderful little maid, you know."

"Maybe I should go get him a little lace apron," Rita teased. "With those heels he'll look the part!"

My face must have been ten shades of red, judging from the smiles I saw before me.

Rita offered to help, but I said I would manage just fine by myself. The truth was I was terrified and I wanted to keep busy, to keep my mind off my worries. In a way I was relieved; if anything, I surely didn't feel like undergoing one of Rita's interrogations. I was having a hard enough time just managing myself in my lingerie-swimwear.

I spent as much time in the water as I could that day and I actually had a pretty good time. Mom and Mrs. Johnston even joined in the fun, splashing and playing like children themselves. For once I felt happy as I played with my mom, like this was the way things were supposed to be.

The late afternoon was spent lazing in the sun. Mom pulled out the lotion and called me over to where she was sitting. Following her instructions, I knelt before her and let her cover me up with the sticky white stuff, listening ruefully as she preached the evils of "too much sun." I about panicked when she pulled the shoulder straps off my suit and tugged down the front, completely exposing my swollen breasts. Even though I was a boy, I was still pretty self conscious about my body and I wasn't too crazy about letting just anyone see me like that; I mean, even as "Greg" I rarely let anyone see me without at least a t-shirt on. Rita and her mom laughed good-naturedly as I crossed my arms over my partial nudity. Mom just rolled her eyes and lathered me up with lotion like it was an everyday occurrence.

In turn, I was then tasked with putting lotion on my mother. Following her example, I squeezed a puddle of the white goop in my palm, smeared some on my other hand, and went to work. Ever the perfectionist, Mom told me where she wanted me work, guiding my every move with the same precision and firmness that she established when teaching me how to do my chores at home. Almost immediately I realized that there was something exciting about touching a woman's body, especially when being controlled by a woman like my mom.

Mrs. Johnston was next. I felt my mouth go dry as I knelt down next to where she lay. Smiling at me with those bright red lipstick painted lips, Mrs. Johnston was as particular as my own mother in telling me where she wanted me to put the lotion. She didn't move a muscle as my fingers danced across her skin. I tried desperately to avoid certain areas that I thought were off limits, and when I did I could see her mouth twitch, grinning at my inexperience and caution. I thought I would croak when she undid the back of her suit and let it fall forward; she laughed and said it was all right, it was "just us girls." She bade me to put lotion on the tops of her breasts to keep them from getting burned. My stomach dropped as I felt something tingling down between my legs. Glancing at my mom, I could see her watching me carefully. I didn't say a word, but I've no doubt that the blotchiness on my own chest had nothing to do with the sun.

By the time I got to Rita I was a nervous wreck. She had me start at her feet and work my way up. At nineteen years of age, she had the body of a movie star and I relished the chance to touch her in ways that few, if any, boys had done. I about died when I got to her thighs and she casually took my hand and guided it all the way up to the edge of her suit; I mean, here I had my hand between her legs, mere millimeters away from her crotch, and everyone seemed to accept it as naturally as the clouds that passed overhead.

Like her mother, Rita also dropped her top. I had to look away to keep my eyes from popping out. Seeing my shyness, she put her hands on mine and guided them to her breasts, helping me work the lotion into her skin while I fought to keep from having a spasm. I remember my mom looking at me with a raised eyebrow, as though she was judging my performance. I couldn't breath and my face was hot and my body trembled so. Even worse, I could feel my erection straining against the tight elastic of my bikini panties, so much that I was practically in pain; I wanted desperately to jump in the pool to conceal my shame, but that would have been impossible to explain. The look on Rita's face let me know that she was fully aware of what was going on.

When I was done Mom told me to lay down and catch a little sun. "A little tan will do you good as long as we're careful. This is one of the best parts about being a girl."

I had just made myself comfortable, laying on my back, when I felt a pair of hands tugging at my bikini bottom. I looked up to see Rita — still topless — bending over me, a great big smile plastered on her face.

"Here, 'Pamela,' it looks like you missed a spot," she said, her eyes sparkling with mischief. "You don't want to get burned, do you?"

She then began rubbing lotion on the tops of my legs and up under my bathing suit bottom. The next thing I knew the ties on either side came loose and half of my suit was off. Quickly and desperately, I rolled onto my stomach, and by not before everyone got a look at what I'd been hiding between my legs. I glanced up and behind me to see my tormentor holding my girlie bikini bottom over her head like a trophy of some sort.

Mom and Mrs. Johnston both laughed and clapped their hands. It was like I was trapped in some silly, girlish ritual, something that went on between sisters or girlfriends, not unlike the horseplay that goes on between the guys. In this case I just happened to be the little sister, the quiet, younger girlfriend who had a lot to learn about hanging out with the big girls. In keeping with that role, I couldn't help but cry — well, just a little — and beg for my bikini bottom to be returned. Rita held it behind her back and grinned.

"Come and get it, 'Pamela' darling. I dare you!"

Well, needless to say, I wasn't about to get up and do anything. Instead, I kept the front of my body plastered against my beach towel and fussed and whined about how "it's not fair!" This prompted a scolding from my mother to hush up.

"Oh, Greg, honestly! Don't be such a crybaby," she warned me. "She's just having a little fun with you. I can't believe how you're acting!"

"That's right, sweetie, just a little fun." Rita grinned. "I'll tell you what. I promise to give it back if Kevin and his buddies come back. We wouldn't want those old boys looking at your little bare bottom, would we?"

And so I remained bottomless, as well as helpless to do anything about it.

The rest of the day was spent lazing in the sun, browsing through magazines, napping and sipping iced drinks. I dozed off and on throughout, waking up long enough to pull my towel over my exposed bottom every once in a while; likewise, Rita — or Mom or probably even Mrs. Johnston, for all I knew — would tug the towel down, leaving my bare buns exposed to the hot sun. The next day I'd have the strangest suntan; a red and aching butt, contrasted with the white lines on my shoulders, back and chest from wearing a girl's top.

What a way to end the summer ....

 

 

Chapter 20 — Back to School

 

When I went back to school in the fall, it was like having a new start. I was entering high school and there were over 2000 students on campus and only a few of those from last year would be in my classes. Everyone had a clean slate and unless I made an issue of it, I believed that my sissy image was a thing of the past.

A few things stood out like Mom insisting that I not get a haircut. It would ruin my teenage girl look for when I needed correction. In addition to dressing up around the house, there were a number of episodes where I again had to wear lipstick and girls’ clothes out in public, but they lasted only a day or two and I was allowed to resume my normal routine. When these occasions did occur and we were out, Mom would frequently buy me little bracelets or charms to wear.

Just before dinner one evening Dave was excused to go to his room, and Mom and I had a long talk.

"I know just how embarrassing this will be for you if I make you go to school like this," she started. I looked down at myself and nodded. Wearing a pink mini-skirt and a short silk t-shirt with a fairy embroidered on the front at the time, I agreed that I probably was in violation of the school dress code. At least as far as boys were concerned. "And while part of your punishment is to be shamed, I certainly don’t want to place you in any danger. So I have an alternative that I want you to consider. That is, unless you do want to wear lipstick and dresses to school."

Eager to hear her plan, I shook my head from side to side; the twin ponytails dangling from the sides of my head reminded me of how much was at stake. Anything, I thought, is better than going to school dressed like a total geek.

"That's what I thought. Here's the deal. You can go to school in your boy clothes … for now. I don't really have a problem with that. As long as you stay out of fights and keep your grades up and don't steal anything, I won't try to embarrass you. Well, not too much. However, you will continue with your chores and duties here at the house, and you'll do them in your girlie clothes, just like we did this summer. That seems to be the only way I can make sure you're not running off and getting into trouble with your friends."

"But, Mom …." I started to complain, but a sharp look from her told me to keep my mouth shut. Like I said, I wasn't completely stupid.

"There is one condition to all of this, though. Every now and then, you'll probably end up at school in a dress, just for fun." I felt a shiver run through my entire body. Mom noticed and smiled. "Like it or not, sweetie, that's the way it's going to be. For example, in two weeks your new high school is having a Sadie Hawkins Day celebration. If it's like when I went there, they dress up during the day and have a dance that evening. On Sadie Hawkins Day some of the boys dress up as girls and vice versa. So, here's the deal. If you’ll let me dress you up for Sadie Hawkins Day anyway I choose, then I’ll let you wear your normal clothes to school tomorrow and thereafter. You’ll just be considered one of the ones who have gotten into the spirit of the event. You shouldn’t stand out like last year."

I started to say something, but got a finger stuck in my face instead.

"But before you agree, I want you to agree to let me have full license to do whatever I want to make you look like a real girl. You think about it overnight and then you decide how you go to school in the morning. Just remember, that if you go in your normal clothes, you’ve committed to letting me dress you fully two weeks from now. Understand?"

I agreed that I understood, but the whole situation had my head spinning. Was she kidding? I already knew which choice I would be making in the morning.

Next morning I dressed for school as usual, sealing my fate for two weeks from now. Mom came into my room and saw me in my regular clothes.

"Hold on a minute," she said. "While I’m not going to make you dress outwardly as a girl you’re not getting off completely free. Here, wear these," she instructed as she pulled out a pair of panties and one of my long legged girdles. "Your jeans will cover them and you won’t have PE since it’s raining."

Grudgingly, I removed my pants and jockey shorts, put on the panties and girdle and redressed in my jeans. To my chagrin I noticed that the garter tabs could be clearly felt through the denim material, and if you looked closely they were just barely visible. At I didn’t have the sensation of the stockings pulling down on them.

As I was headed out the door on my way to school Mom stopped me and commented that I might want to remove my earrings before I left.

"Oh, god." I thought. I remembered just a few weeks ago when I got caught wearing lipstick to the ball field, "What if I’d worn my earrings to school?"

Mom helped me take them out and then put a touch of makeup over each hole and assured me that they weren’t noticeable. I wanted to believe her, but what choice did I have really?

That year I was taking the district bus rather than riding my bike, as the high school was across town. As I ran down the street to the corner were I caught the bus, I had to stop and pull the edges of my panty girdle down along the rear of my leg. Great. Something that I’d gotten used to while wearing my dresses was now a source of major embarrassment in my boy clothes. Was this going to be going all day? If so, would I have to put up with it lest someone notice what I was doing?

As the day progressed, I found that I could hide my actions beneath my desktop by smooth out the girdle’s edges after I had taken my seat. Those damn tabs were there every time. My terror had somewhat resolved itself by lunch time and I did my best to keep from fidgeting with my earlobes. All and all, I managed to get through the day without anyone seeming to notice.

Mom heard me come in the back door and called, "Greg, is that you?"

When I answered "Yes," I was directed to my bedroom. There laid out on the bed was an ensemble of clothes for me to put on, including my yellow sheath, stockings and high heeled shoes. I removed my school clothes, donned the selected garments and then find my Mom to have her button me up. She saw that I wasn’t wearing my makeup, I was sent off to apply it and then report back to her.

"Now, ‘Pamela,’ just because you’re going to school as a boy doesn’t mean you can skip your responsibilities." She gave me a warm, motherly smile. My knees went weak as she handed me a list of chores that would have made a brigade of maids tremble with fear.

I spent nearly two hours working on the laundry and the ironing, hand washing a huge pile of lingerie and pressing one nurse’s uniform after another. After that I had to vacuum the carpets and then dust the living room and dining room. Only then could I start my homework.

As much as I hated my summer vacation, it seemed that high school was going to be even worse.

For the most part, the next two weeks was pretty much a carbon copy of this first day after school. I made sure to conduct an inspection each morning before leaving the house, just to make sure all my lipstick was wiped off and I wasn’t wearing any earrings, and I learned that if I wore the panty briefs I didn’t have to deal with the legs rolling up. I also fell into the after school routine without having to be nagged through it daily.

The only really new twist came on Monday of week two, when a new pair of bright red four inch heels magically appeared on my bed after school. They were open toed and of a sandal-type construction with only a small ankle strap to hold them on. Mom insisted that I wear them as often as possible to get used to how they felt. Indeed, they presented a significant challenge in walking compared to the three inch pumps, but by the third day I was maneuvering quite well in them also.

 

Continue on with Chapter 21 of "Lipstick Discipline"

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