Chapter 8 – Let's Play Pool Princess
I woke up from a bad dream the morning of my first day back in sixth grade. I had been standing in front of my old class at school giving a report when suddenly I realized I was wearing nothing but lacy anklet socks, pearl white patent leather Mary Janes, and a pair of white cotton panties decorated with lavender flowers. I looked at my fingernails and saw them painted in matching lavender polish. I was holding a bouquet of purple flowers in one hand and a fancy, old fashioned doll in a prissy lavender dress in the other. I reached up to my hair and felt it tied up in a pony tail with a ribbon and I could tell my face was made up as well. The entire class was pointing and laughing at the tent in my panties. I reached down to cover myself up with the flowers and the doll but they only laughed harder. I wet myself in fear and the urine ran down my leg to the floor of the classroom before I burst awake from the terrible fantasy. The humiliating warm wetness, however, was real. I could feel the flow stopping as I awoke.
I rolled out of bed and stood, my legs wobbled. In a numb haze I started to walk from my room. On the way I passed my prissy lavender back-to-school dress as it hung on the door of my closet, ready and waiting. I knocked quietly on Mother's door before entering. I realized I was up half an hour early. I sat down on the bed beside her and started to cry. In a few moments I felt her stir awake and put her arm around me.
“Samantha, what's wrong?” Mother asked.
“I'm wet again. I don't wanna go to school. I'm just a big bed wetting baby. I want to stay here with you,” I whined.
She comforted me for a few minutes until my crying and whining subsided. She looked over at the clock and realized it was early, “Samantha, did you wake up when it was happening, dear?
Ashamed of myself, I nodded, “Yes, Mother.”
She smiled and tried to encourage me, “Well, that's progress, Samantha. It never happened before. You almost made it through the night and you almost woke up in time! Your bedwetting days will be over soon, trust me! You're not a baby and you ARE going to school today. If it doesn't work out I told you I will homeschool you but you made this decision and you have to see it through. Now go and get ready.”
“Yes, Mother,” I replied with a pout.
A little while later I was glumly helping Mother make breakfast. My apron covered my back to school outfit to keep it bright and clean. I wore a lavender reverse knot ruffle dress. The fabric was soft and light and the print was accented with jewels and crowns and tiaras, emphasizing what a pampered little princess I had become. There was a white ruffle at the hem with purple polka dots. I wore a white cardigan and white tights and lavender canvas Mary Janes with a white flower on the buckle.
The french braid in my hair had grown long over the months and it hung down over my shoulder onto my chest where I saw the lavender bow that tied it off. I wore my pearl necklace as usual, clip on gold earrings with a purple stone, and Mother had given me two thin white gold and diamond bracelets to wear. She warned me they were expensive and that I had to be very careful not to lose them. I was only half listening as I admired the small sparkly diamonds, but if she had told me how expensive they really were I probably would have been too afraid to leave the house with them. In truth, with my expensive dress and jewelry and pink designer bookbag my entire ensemble was worth more than my old family's ancient beat up used car. It hadn't entirely dawned on me yet how privileged I had become.
Just as we finished preparing breakfast the phone rang and I picked it up. I answered as I had been trained, “Hello, Donovan residence, this is Samantha.”
The line was silent for a moment.
“Sa..who?” I heard a deep female voice say in confusion.
“Hello?” I asked.
“Is my...is Mrs. Donovan there?” the voice asked nervously.
“Whom may I say is calling?” I primly inquired.
“I'm her...I'm Cameron,” the voice replied. “Who are you?”
“I'm her...daughter,” I replied, to silence. With a shrug I turned to Mother, “Mother, someone named Cameron is calling for you.”
Her face turned white. She ordered me to take my breakfast up to my room. I figured it must have been an important call about her design business. Of course, that didn't explain the muffled crying I thought I heard later.
Mother drove me to school. I would usually take the bus but she needed to drop me off to talk to the Principal for my first day. She was unusually quiet and withdrawn. I looked down at one of the sparkly tiaras on my dress. I hated tiaras.
-
For a while one summer we had a babysitter named Annabelle. Mom and Dad were sick of leaving us unsupervised only to come home and find Kelly crying because, “My stupid big brother is dressing in my clothes again!” so they would drop us off at Annabelle's house every day.
Annabelle was a nineteen year old beautiful redhead who was home for the summer from college and had quite a temper. We disliked each other right from the start and I did everything I could to stay out of her way. My sister, of course, took an instant liking to her.
The most fun I had the first few days was swimming in the large pool they had in their backyard. I stayed out there for hours. Annabelle and Kelly had the same idea though, and the constant laughter and teasing finally ruined the fun for me.
From then on I started to stay inside and read instead, but the more I heard the giggling and laughter from outside the more I knew it was most likely targeted in my direction. If I knew Kelly, she was telling our babysitter everything about my least favorite game, or at least some of the details.
A week later, my fears proved prescient. I was sitting inside reading as usual when Annabelle walked up and snatched the book from me. She was wet from the pool and wearing a black bikini that would normally make a boy drool but I had other things to worry about.
“Hey, give it back!” I demanded but she held it out of my reach.
“You spend too much time indoors, come outside and go swimming with us again. It's beautiful out there!” she told me.
“I didn't bring my swimsuit,” I replied, falling directly into the trap that had been set for me.
Annabelle grinned, “Oh, don't worry, I'm sure we can find a spare.”
She took my hand and started leading my up the stairs. “She means one from her father,” I thought. “She means one her boyfriend left here,” I thought. “She doesn't mean that. Please, she doesn't mean something like that,” I thought as she opened the door in front of me.
Annabelle shoved me into the room. I saw pink walls and a pink bed and dolls and flowers and princess posters and knew I was doomed. Annabelle had a little sister too. She was away at summer camp.
I screamed as I felt a sudden shove and collapsed onto the floor. A familiar high pitched jovial voice rang out, “Let's play the Sissy-Girly Game!”
Kelly had been hiding in the room waiting for us. I tried to turn and get up. I couldn't let her do this to me in front of a hot older girl. It would be infuriating and humiliating, but I was too slow. Before I could find my feet Kelly pounced on me, pinned me, and started pulling hard on my hair. I screamed.
“Stop it! Stop it!” I begged. “Annabelle, get her off me! Kelly, what are you doing?” I screamed, trying to act as if this was not a regular occurrence for me.
I could hear Annabelle laughing at the sight of a fully clothed boy being beat up by a little girl in a bathing suit. Clearly our babysitter was not going to be my salvation. I redoubled my efforts to fight but Kelly slapped my hands away and resumed yanking at my hair.
Kelly kept me pinned down as I struggled and addressed Annabelle as if I couldn't hear her, “It always takes him a few minutes to give up. It's part of the fun for him! You know how boys like to fight. Once he's got that silliness out of his system we can get down to the part he REALLY likes!”
“I don't like any of it!” I screamed.
Kelly laughed and stopped pulling my hair. I looked up and sneered at her. I hated her so much.
“Sometimes he just needs to be reminded he's really a prissy little girl at heart before he gives up. Like if I spit on a boy...that would never make him say it.” She cleared her throat and started to lean over my face. This had gotten me to break before. I grimaced and shut my eyes. She could see that I was determined to take it this time.
“Or....” she continued.
I opened my eyes. She jammed a finger up her nose and retrieved a disgusting green booger. She started to reach towards my face. I forgot about Annabelle watching. I forgot about everything but how much I hated my stupid sister and didn't want her stupid booger touching me and almost involuntarily I shouted in a practiced, high pitched girly voice, “I'm a prissy little sissy-girly and I want everyone to know it!”
Kelly smiled in satisfaction and flicked the booger away. Annabelle laughed until she was crying, “He said it! I can't believe he really said it! You are the meanest little sister in the world, Kelly!”
Kelly smiled at what was, between the two of them, a compliment. I stood up and rubbed my head as Kelly replied to Annabelle, “So, that's how it's done. You wanna take your turn?”
“Of course!” Annabelle replied. “Let's play the Sissy-Girly Game!” Annabelle ran towards me as my eyes opened in shock. If I couldn't fight off my little sister there was no way I was going to be able to fight off my babysitter. I turned around to run, but of course there was nowhere for me to go. Annabelle grabbed my left wrist and bent it back. I screamed in pain. My other hand shot out to my side and I held it limply while I stood on my toes. Kelly had grabbed my wrist this way when she was training me to walk like a girl in heels and my reaction was involuntarily.
Annabelle laughed hysterically, “He's a natural fairy! Isn't he?”
Kelly nodded at her with a smile. Annabelle tossed me on the bed and pinned me and started to playfully slap at my cheeks. “Don't make me hurt you...Samantha,” Annabelle warned with a giggle.
But something else besides the game was now occupying my mind. I was pinned to the bed by a beautiful wet older girl dressed only in a bikini. Her breasts bounced in front of me as her warm hands kept touching my face.
“Just say it, Samantha. Say it for me like you did your little sister!” she teased as she continued to straddle me.
She shook me by the shoulders and repeated, “Do it! Do it!” I stared up into her beautiful eyes and a hint of a smile came to my lips. The world closed in around us and my brain shut down, some drool escaped my lips. I stopped fighting and as I went limp one part of me stayed hard. Annabelle looked down and saw what was happening and her eyes went wide.
“I'm a prissy little sissy-girly and I want everyone to know it!” I shouted.
She moved to get off me but the inevitable had already occurred. My body convulsed and my face twitched. The room spun around me and I felt just the most wonderful sensation of my life.
Annabelle covered her mouth in shock, “Oh my God, he really does like this game!”
Kelly looked over at me, “He sure does, but usually not that much.”
Annabelle helped me to my feet and told me to go to the bathroom and strip. Still in a haze I obeyed, my hatred for my babysitter now mixed with some other strange feelings I could not quite explain. I tossed my clothes out of the room on command and the bathing suit I was to borrow came in exchange. I shuddered when I saw it.
In a few moments I was standing before them in the most humiliating bathing suit imaginable. With my brief moment of exhilaration over I just felt degraded and pathetic while they laughed at me. I was wearing a purple one piece Disney Store swimsuit with screen and glitter art of Rapunzel from Tangled surrounded by embroidered pink flowers. There were dark purple ruffle fabric rosettes across chest, double shoulder straps, and a skirt with a gathered light pink ruffle hem.
“Oh my God, Samantha! You're so cute! Now put these on!” Annabelle gushed as she handed me a pair of purple flip flops that matched the suit. They featured Rapunzel screen art and had gel straps that sparkled with sequins and glitter. There was a large floral applique with a sparkly jewel in the center of the straps.
To complete the set there was a light purple hooded coverup to wear over the suit on the way to and from the pool. There was an embroidered Rapunzel of course and there were ruffle trims around the hood opening and the sleeves. It buttoned up with three heart shaped buttons above a delicate bow.
“Makeup time!” Kelly squealed.
“But Kelly,” I whined, “We're just going to the pool.”
Annabelle laughed, “It's okay, Samantha, we're just playing.”
“But I HATE this game.” I stamped my foot and shook my limp wristed arms at my side and pouted and they both laughed at me. I sounded and looked exactly like the type of prissy little princess who would wear the matching Disney swimming outfit I had on. Kelly had made sure feminine behavior was totally natural to me when we were playing the game and a lot of the time I didn't even know I was doing it.
Annabelle dragged me over to the mirror and I sat down in a practiced, feminine, demure manner to more giggles from Annabelle. “I've trained him so well!” Kelly bragged.
My face turned red in shame and anger. I hated when she said stuff like that and she knew it, but there was nothing I could do to stop her. They started to work together to make me up. They made me up so heavily I looked like I would be going to a ballet recital rather than just out to the pool. I had girly pink lips and pink eye shadow and pink blushing cheeks. When they were done they topped everything off by putting a glittery tiara on my head and letting me soak in my appearance in the mirror.
I was a perfect prissy pool princess. I hated how the tight girl's bathing suit felt like it was shaping my body into that of a little girl and when I looked in the mirror I could see my appearance matched the feeling. I started to breathe heavily and panic. All of my masculinity was gone and my sister and babysitter had replaced it with a femininity that was impossible to deny.
While I stood in front of the mirror the girls put on jeans and t-shirts over their bathing suits and then led me downstairs and out the front door. “Wait...where are we going? The pool is out back,” I complained.
Annabelle laughed, “You're too pretty to hide in the back yard, Samantha. We're going to the public pool!”
“Nooo!” I shouted but Annabelle swatted me on my behind and herded me into the car while Kelly laughed.
“I can't go out in public like this!” I continued to complain, “Someone will recognize me!”
Kelly taunted me, “Don't be silly, little sis, you're the one who said you wanted everyone to know what a prissy little sissy-girly you are! You even said it twice! Now everyone will know! It's a dream come true!”
I started to cry. I was hopelessly trapped. Kelly glared at me and ordered me not to ruin my makeup. We finished the short drive to the public pool and Kelly dragged me out of the car. Annabelle lifted the frilly purple coverup over my head leaving me exposed in nothing but my skirted one piece Disney princess bathing suit and flip flops and sparkly tiara. My heart thumped in my chest and my head started to spin. My life was about to be over. I could never live down showing up at the public pool dressed like a little girl. There had to be some way out.
Annabelle giggled as she revealed a purple and pink set of water wings and I numbly stood as she slipped them on my arms. They made my appearance even more juvenile. Annabelle and Kelly went to the trunk of the car to get their towels and with their backs turned I saw my only chance at salvation. I cringed at what I saw, but it was the only way and I had only an instant to act. I sprinted away. Someone had left a bike unattended and unlocked on the bike rack.
I was peddling away before they even knew what happened. It was a bright pink Barbie themed bike with a white basket lined with pink flowers and pink and white streamers on the handlebars. You can bet it didn't make me feel like any less of an effeminate little sissy to be peddling away on it in my pink and purple Rapunzel bathing suit but at least it was better than going to the public pool and almost certainly being seen by my classmates.
I started to make my way back to Annabelle's house, staying off the main roads. I couldn't go back to my house until I got my clothes back. I kept looking behind me in frantic fear that they might be chasing me down in the car but they were nowhere to be seen. About a block away I got off the embarrassing pink bike and was about to ditch it when a police car drove up and stopped next to me. The officer looked at me intently before getting out of his car to confront me.
I stood there shaking in numb fear. Annabelle must have called the police to find me. Or someone saw the little girl's bike being stolen and called them. Either way, I was dead. As I shook the officer spoke, “Little girl, if you're going to ride your bike you have to wear a helmet. It's the law. Those water wings may help you swim but they won't help if you fall off your bike!” he lectured.
A helmet. He was just worried about a helmet. Instinctively my hand went to my head and I felt the tiara perched there. “I know you want to look pretty, but it's for your own good! Tiraras are for dress-up at home, not for bike riding! Now run along home, and don't let me see you riding without a helmet again, missy!”
“Y...yes officer,” I squeaked, “I'm sorry!” I walked the rest of the way to Annabelle's house leading the bike beside me. I left it propped up by a mailbox so it would be easy to find if the police did start looking for it. I approached Annabelle's house but all the doors were locked. I screamed in frustration. I went around back and ripped off the water wings and sat down in a lounge chair by the pool to wait for my tormenters to come back and put an end to this stupid game. After a little while, exhausted by my ordeal and my frantic bike trip, I fell asleep.
I awoke to the sound of a woman and a little girl talking. I jumped out of the chair and saw them. There was a red haired older woman and a red haired little girl. They both looked shocked upon seeing me.
“Mommy! Who is that?! Why is she wearing my bathing suit and my tiara?” the little girl whined.
The mother replied, “Annabelle was babysitting while you were at camp, remember? This girl must have forgotten her suit and...”
Suddenly the door to the house popped open and Annabelle and Kelly came out to the yard. They must have come home while I was sleeping and left me out there.
“Jimmy! What are you wearing?!” Kelly shouted in feigned shock.
Annabelle joined in, “I know your Mother said you love to play dress-up but I only left you alone for a few minutes and now I find you out here dressed in my little sister's bathing suit? It's very rude to do that without asking! You should know better.”
Annabelle's little sister started to cry, “Ewwwww, it's a boy! He ruined it! I can't wear it anymore!”
Annabelle's mother was predictably furious, “You perverted, nasty little brat! Your parents are going to hear about this! You are not welcome in this house ever again!”
“No,” I whined, “Please don't tell my parents, please! I'll get in so much trouble!”
“You deserve to!” she screamed back.
The frilly purple cover-up was dropped back over my head and Kelly and I were driven home. Kelly was angry and blamed me for making it so Annabelle couldn't babysit us anymore. As if it was my fault she had to play her stupid game.
So that's how I ended up presented to my parents dressed as a pretty little pool princess in a glittery tiara. I was stripped out of the suit and given a wicked spanking. The feminine tan lines were apparent for weeks. They threw out the suit and the cover-up and the flip flops but Kelly managed to sneak away the tiara. I wore it almost every time we played the game from then on. I really hate tiaras.
-
I was extremely conscious that all the other girls, even the first and second graders, were not dressed as girly-girl prissy as I was. They mostly wore jeans or capris and t-shirts and sneakers and wore their hair straight while I was in a dress and tights and Mary Janes with french braided hair and pretty jewelry.
Mother led me to my classroom and gave me a kiss goodbye on the cheek. I had my designer pink leather bookbag on my shoulder and a shiny red apple in my hand. I entered the classroom with butterflies dancing in my stomach.
In accordance with my orders to be a perfect teacher's pet I went straight up to the teacher's desk and introduced myself, “Hello Mrs. Thomas. I'm Samantha Anne Donovan. Pleased to meet you,” before handing her the apple with a smile and a little curtsy.
“Pleased to meet you too, Samantha, you can put your things down over there,” she gestured to a desk in the front row. Of course Mother had made sure that's where I would be sitting, “...and then I'll introduce you to the class.”
I smiled when I saw who would be sitting next to me. It was my friend Marcie. She was wearing a fancy blue dress that was almost as out of place as mine was. I figured we would be the class girly-girls together. At least I wouldn't be alone.
Marcie smiled back and we hugged, “Hi, Samantha!” She held up an iPhone in a purple case, “Look what I got! We can text all the time now!” she went on, talking a mile a minute, “Why weren't you at the assembly yesterday, did you hear that we're getting a new girl in class who used to be a boy?! Can you believe it? What do you think she'll look like, do you think she'll be weird...”
She trailed off as she saw my face had gone screwed up like I was about to cry, but before she could ask what was wrong Mrs. Thomas led me away to the front of the class.
“Quiet down, everyone!” she instructed and received prompt obedience, “This is the new girl we talked about yesterday. I expect you to treat her like any other girl and make her feel welcome. If I find out that anyone is picking on her just because she's different, there is going to be big trouble!”
My cheeks burned red as I looked at my new classmates. Nobody was pointing and laughing like in the nightmare I had about my old school. They just seemed shocked and awed. They had never known me as a boy, after all, and if they hadn't been told they would have just seen me as any other girl. Now though, they knew I was different. I felt like such a freak.
“Say hello to Samantha Donovan, class.” Mrs. Thomas instructed.
“Hello, Samantha,” they repeated in unison, all but Marcie who was simply starring at me in open mouthed shock.
I couldn't stand it. She hated me now for being such a weirdo.
“H...Hi everyon..” I tried to get out, but before I could finish I burst into tears and ran from the classroom. If I didn't have a friend, I just couldn't do this. I just couldn't do it. I ran towards the office. I was going to make them call Mother to bring me home. Before I got there a hand grabbed my own from behind and stopped me.
I turned around. It was Marcie. She was crying now too, “I'm sorry, I'm sorry! Don't go!” She put her arms around me and held me tightly in a bear hug, “I don't care if you're really a boy, we're still friends!” she insisted.
“We...are?” I asked in surprise. “But why did you...”
Marcie laughed through her tears, “Why didn't you tell me? How can we be best friends when we never talk?”
“From now on,” I replied, “We tell each other everything.”
She handed me a tissue and I dried my tears. We held hands and walked back to the classroom. I had my friend. My best friend. I could do this. From then on we sat together in every class, every day at lunch, every day on the bus, and whenever else we could. When we weren't together we were glued to our phones texting each other and driving our parents crazy. We may still have been two shy girls to everyone else, but not with each other. She never treated me like a freak, even when other kids made fun of me behind my back.
My first day at my new school didn't end up going that badly, aside from one thing. Marcie and I sat together at recess chatting and reading our books. I had just finished “The Secret Garden” and had started “Little Women.” I smiled at the memory of Mr. Craven finding the secret garden in full bloom and full of happy, healthy children. The sounds of recess reminded me of what it must have been like for him.
We saw a girl and two boys hiding behind a shed smoking cigarettes. Marcie identified them as Jenny, Pat, and Kevin. Marcie told me they were the most popular kids in class. I instantly stood up and started looking for an adult.
“What are you doing, Samantha?” Marcie asked.
“Telling on them,” I replied with a blush.
“But you can't, you'll have the whole class mad at you,” she insisted.
“I have to. Mother said so. She said if she hears I knew about anything bad kids are doing in class and don't tell I'll be in as much trouble as if I did it myself,” I told her with concern.
“You don't always have to do what your Mother says, Samantha!” she yelled after me as I ran off.
Jenny peaked out from behind the shed and saw the new “girl” in the prissy purple dress and the expensive jewelry running up to the teacher's aide and pointing in their direction. My reputation as a tattle tale was set in stone from day one. Besides Marcie, I didn't think I would be making many friends in my new class.
Betty Pearl's Sissy Stories 20.1
Topic: The Sissy-Girly Game (Read 34786 times)
