Naked on Summer Vacation Sissy Summer SchoolChapter 6
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Buddy and Lewis were eating worms out of Mrs. Hannigan’s flower patch when I came outside in panties and asked them to go inside. They washed off with the garden hose and came inside still dripping wet when I told them their mother wanted to see them.
My Aunt had been collecting her thoughts on how to address my punishment with Buddy and Lewis. I was still getting my head around what was expected of me, and I didn’t expect my simpleton cousins to get it at all.
“This is your cousin Jenny now,” My Aunt pointed to me. “She is a girl,” she explained to Buddy and Lewis.
“I can see her, boobies!” Lewis smirked. He looked like his Mom in the face when he did. Buddy and Lewis both stared at my bare chest like it was something to see.
“Yes, she will be wearing panties around the house and will bathe with you and generally play with you just like Eddie did. You are not to treat her any differently,” My Aunt said sternly.
Buddy cocked his leg and farted. Lewis giggled and asked when dinner was.
“It is right now,” My Aunt clapped her hands like that matter was settled and resolved and got off the couch. My Aunt Sam told Blair to start dinner and said she would join her shortly to help prepare the food. Then she took me by the hand and led me to the bathroom for my first milking.
“I don’t know if you use lotion, but there is hand lotion on the sink. Please remove your panties while you milk yourself. I don’t want you leaving a stain as you did in my corner. Clean it all up with a Kleenex and bring it to me when you are finished,” my Aunt pointed out everything I would need and was prepared to leave me alone in the bathroom.
“How do I do it, Ma’am?” I asked curiously.
“Just as you would normally masturbate. I assume you can finish in time to join us for dinner?” she asked.
“I don’t know how to do it, Ma’am,” I turned red-faced.
“Oh for Pete Sakes, I hardly believe that,” My Aunt put her hands on her hips and glowered at me.
“I’ve no interest in watching you milk yourself if that is what this is about,” my Aunt suspected I was trying to get her to observe me playing with myself. In truth, I thought it was intensely humiliating even to discuss it much less do it. I had been told I would go blind or grow hair on my palms if I did.
My Aunt stepped into the bathroom, shut the door, and sighed. She told me to remove my panties and keep the ribbon around my balls. My Aunt squirted some lotion into my hand and told me to rub it vigorously on my penis like I was putting on suntan lotion. My Aunt observed as I rubbed the lotion all over my cock. It did feel strange in a good way.
“Now, you pull. You can pull fast; you can pull at a medium pace. Everyone has a preference. Nature will take its course, and you will shoot out your milk into a napkin that you will bring to me. It is very simple Jenny and before you ask I am not going to do it for you,” my Aunt put her hands on her hips and stood over me as I held my cock in my hand.
I pulled my cock, and it felt good.
“You’ve been playing with that thing just about any time you could since you arrived. I’ve caught you with your hand on it often enough. Just do what you’ve wanted to do and get it out of your system. You can picture whatever you need to picture if that helps,” she explained.
I didn’t understand.
“If you need to picture a pretty girl or something,” My Aunt looked at me like she believed that I was telling her the truth that I didn’t know what to do. She pulled her robe open and revealed her well-suntanned boobs. They stood straight out like balloons on her chest, and I recall the long dark nubs of her nipples set in the center of her small areola. “There, think about that instead of your Cousin Blair. You have five minutes!” my Aunt turned and left, closing the bathroom door behind her. She told me I could lock the door as she walked away.
There I stood with my fingers wrapped around my dick. The mental image of my Aunt’s tits in my mind. They were real woman’s boobs. I couldn’t help thinking back to Crystal’s flat chest and how the nipples looked almost inverted like the nub went back inside her boobs. I looked at myself in the mirror as I stood in front of the toilet and stroked my cock slowly and then at a medium pace. It felt good, and when I finally released my cum into the kleenex, I released a lot. A lot more than I thought I would.
I fell to my knees for a moment and lost my breath. It was as if every dirty thought had been plucked from my mind and replaced with a math problem or a story from a cartoon instead. My cock shriveled into nothing, and I worried for a moment that I might have broken my dick in the process of milking it. I worried that it might never get hard again.
“Jenny! your five minutes is up!” My Aunt shouted and sent Blair to come to get me. I unlocked the door just as she did.
Blair’s eyes got wide at the size of the wad of cum in the tissue in my hand, and she laughed.
“What is so funny?” Buddy laughed with Blair when we came into the kitchen as he ate his food.
“Jenny sneezed a lot,” Blair pointed to my tissue, and my Aunt looked impressed.
“Good job, Jenny. Do you feel better now that you have blown your nose?” she asked me.
“Yes, Ma’am,” I curtsied clumsily.
“Good, put your panties on and sit at the table,” My Aunt had a microwave dinner for me in the microwave. I wasn’t used to “Lean Cuisine,” but it was considered a delicacy at my Aunt’s house.
Blair showed me how to eat with my fork and hold out a pinky at the table. She told me to cross my legs and sit like a lady.
After we finished eating, I helped put away the mess and clean up.
“Go put makeup on your Cousin and find some of your old outfits for her to wear. We need to teach her to walk before we go to the store,” My Aunt explained to Blair while she did the dishes.
I followed Blair into her bedroom. Her room was an explosion of pastels and female energy, and it kind of overwhelmed my curiosity.
“Keep your sticky fingers out of my shit,” Blair growled at me once she closed her door and slapped my fingers away from a notebook of her doodles.
“Yes, Ma’am,” I curtsied.
“You got lucky! I wanted you to be a puppy!” Blair informed me she had suggested I be trained as a puppy instead. I wasn’t sure how that would have worked at all. “Now come here and let me put makeup on you,” Blair instructed.
Blair really seemed to enjoy treating me like a doll she could play dress up with. She used a curling iron to style my hair and taught me the differences between eyeliner and eye shadow. She taught me how to apply makeup and told me I would need to learn to do this for myself. It seemed extremely complicated.
“They say less is more but with a face with as many freckles as yours I would go with MORE makeup,” Blair showed me what she was doing.
I looked prettier than Crystal. My features were softened, and my freckles were covered up. I had cherry bubble gum lipstick and blue eye shadow that gave me a very trashy sort of country-girl sexy look. At the time, I considered it very fancy, though.
“Let’s go show mom, and then I’ll get you dressed,” Blair was happy with her handiwork, and I think as she used me as a makeup subject, she started to grow a little fonder of me. Fond may not be the right word. It felt like she was becoming possessive of me. She yanked the ribbon around my penis and walked me into the living room behind her to show her mother what I looked like as Jenny.
“That is absolutely fantastic, Blair! You are lovely, Jenny!” my Aunt was ecstatic at the outcome, and Blair naturally felt quite proud of herself for the work she had done transforming me from boy to girl.
I curtsied, and when Blair jerked my ribbon, I followed her back to her room.
Blair opened her closet and began going through her old clothes. She took much more time than she had selecting the Strawberry Shortcake nightshirt. It seemed she actually cared what I wore.
She chose a blueberry colored bra for me that no longer fit her. She showed me how to stuff it with tissue to make it appear I had actual tits. Blair gave me a modest blouse top that wasn’t very revealing. It looked like something any normal girl my age would wear to a store. She chose a pink skirt that would have fit her when she was Lewis’s age for me. The skirt barely covered my butt, but it did. I was told that I should behave like a lady but that I would have prissy skimpy/girly clothes chosen for me. My Aunt said that I was free to hold my skirt down if the wind blows it up, and I would start to appreciate what girls have to go through when men stare.
I never once got hard while I got dressed, and I only had a few dirty thoughts as I looked at my Cousin’s lacey undergarments. I think the milking process worked because I expected opening the world of female secrets to me should have excited me into arousal! Blair noticed me looking at all her stuff while she picked out my new clothes and called me a panty sniffer.
“You may look like a girl, but you are still a dirty boy, Jenny!” she teased my hair with her finger and sprayed me with some strawberry scented cheap perfume before painting my nails and toenails and then giving me a pair of yellow shoes to wear.
They were slightly elevated slippers, and it seemed like it should have been no problem to walk in them. They hurt my feet, though.
Blair pulled my ribbon out of the skirt so that she could still lead me around the house and walked me into the living room where I could model the outfit for her mother’s approval.
“Clomp, clomp, clomp,” my Aunt took a sip of her drink and imitated the sound of my stomping walk as I tried to keep myself from falling down while I walked in the awkward and uncomfortable shoes I was provided.
“You must learn to glide. Watch me,” my Aunt stood up. She was dressed in a blousy sundress and ready to leave. She had on a pair of four-inch heels, and she danced around the room effortlessly. I noticed that she didn’t shuffle or march. She seemed to sweep with a grace that I had never noticed women had when they walked in these kinds of shoes.
Needless to say, it would take quite a bit more practice before I could master that. They were satisfied when I could pass for a clumsy girl.
We left the house, and as we did, Mrs. Hannigan met my Aunt at the door and asked her for the rent.
“I told you it isn’t quite the first yet, Mrs. Hannigan,” Aunt Sam smiled at her, but there was a cattiness to her voice.
“You can provide me with a check, and I can cash it on the first,” Mrs. Hannigan said. It was a discussion they had previously. She noticed me out of the corner of her eye.
“You have another border staying with you?” Mrs. Hannigan clearly didn’t recognize me as Eddie.
“Hello Ma’am,” I said, and I curtsied as I had practiced by lifting my skirt slightly at the sides.
“This is my niece, Jenny. Eddie had to be picked up and taken home for misbehavior,” My Aunt lied.
“He was a delinquent and a deviant if I ever saw one. Your niece seems amiable enough,” Mrs. Hannigan seemed disappointed she had nothing to complain about and then reminded my Aunt that the rent would be due promptly on the first before leaving us to get in the car.
I should mention that I bear a strong natural resemblance on my mother’s side of the family to my cousins and Aunt. We are all gingers with freckles and red hair, and it really shouldn’t have surprised me that Mrs. Hannigan thought I was someone else. We all have that same kind of smirky smile, and our faces look quite similar.
My Aunt chuckled as she opened the door and let me in. I was told to get in the hump seat and remove all of my clothes except for my panties.
“But I just got dressed, Ma’am?” I asked as I sat in the middle of the backseat. It was more of a statement and I knew I had been told not to question my orders but I did it anyway. I had JUST put on all these fancy clothes, and it seemed to make no sense to me to take them off now that I had them on.
“Jenny, what did I tell you about backtalk and questioning instructions from your betters?” My Aunt asked, grimly from the front seat. Blair turned around in the passenger seat of the front and glared at me.
“You told me not to do it, Ma’am. I am sorry, I am still learning. Where shall I place my folded clothes so that they don’t get wrinkled?” I asked politely.
I think it was the fact that I had concern for the care of the clothes that saved my bacon.
My Aunt smiled and told me to fold them and hand them to Blair. “You have a lot to learn Jenny. You can learn it the hard way, or you can learn it by listening and doing what you are told. When we get to the shopping center, everyone will have ice cream except for you. When you have learned to stop questioning my orders that will change,” she said.
I was thankful not to be given another strapping out in the parking lot. I saw Franklin and his brother on their bikes as we drove through the neighborhood. They watched us drive past, and I wondered if they could see me in the backseat sitting there shirtless in a pair of panties next to my cousins.
“How come Jenny has a pee-pee, Mommy?” Buddy asked.
Buddy was stupid, but I felt he had to know I was actually his Cousin Eddie.
“Some girls have innies, and some girls have outies,” My Aunt smirked in her witty sort of way. I didn’t know if that was true, but I would come to learn later that some girls did have pretty huge clitorises that could pass for a tiny penis.
“Is Jenny really, Eddie, Mommy?” Lewis asked his Mom.
“Yes, but until Eddie learns to behave, he can’t play anymore. He has to be Jenny,” My Aunt explained. It seemed as though it wasn’t as simple as just telling them I was Jenny now and leaving it that after all.
“How come his pee-pee isn’t sticking straight up, Mommy?” Buddy asked.
“That is one of the lessons Jenny is learning, and Jenny is going to be a she for a while not a He,” My Aunt explained.
“Can I be a girl, too, Mommy?” Buddy asked enthusiastically.
“Maybe,” my Aunt smiled.
Lewis volunteered as well.
It didn’t make me feel so bad about my situation, after all. I should have been horrified, but I was kind of enjoying it.
“Does this mean we can’t fart on Jenny or play rough because she is a girl? Buddy asked after a little while.
Blair told them to blast way, but my Aunt corrected her and said that they should treat me as they would any girl.
“I’ve never farted on a girl before,” Buddy admitted, and he looked at me as if seeking permission.
I shook my head no to answer Buddy’s silent question, and he looked at his feet and accepted that he couldn’t fart on me any longer. I took that as a small victory.
I remember we were on US One driving on a long stretch of highway. The town was called Wabasso if you could call it a town. There was a small strip mall with a McDonalds, a TG&Y, and a few other stores that they called the “mall.”
We parked, and my Aunt told Blair to give me back my clothes and let me change in the parking lot. No one seemed to notice or care that a little girl was getting dressed in the parking lot. A few people stared, but most people looked away. I noticed that when they thought I was a boy, no one ever felt the need to look elsewhere.
I started to feel a kind of power with being dressed as a girl. My cousins were nicer to me and didn’t try to mess up my hair or punch me. People seemed more polite to me, and they appeared willing even to look the other way when I changed.
I wondered if I would ever have the kind of power that Blair did. She could be rude and insult Jack, and he would laugh it off. Blair tried to make Jack jealous by showing attention to his friend Bruce, and he tolerated that too. She had a kind of power about her that she could get away with things I don’t think a guy her age could have gotten away with.
I knew I wouldn’t be a girl forever. My Aunt had made it very clear I was keeping the biological parts I had been born with and that this was all temporary until I came to learn the lessons she was teaching me. I didn’t even know what all the lessons she intended to teach me were yet.
I knew I was supposed to learn to obey and be polite and considerate to my elders. I knew I was supposed to gain the perspective of girls and appreciate what they go through. I still didn’t really understand the need for pain and humiliation in the process. I was actually enjoying dressing like a girl even though I didn’t want to admit it.
We walked right into TG&Y as if it were perfectly normal - which it seemed like to any outside observer. I was simply a flat-chested girl who talked and walked like a clumsy girl. I held Blair’s hand, but she had the pink ribbon in her hand as she pulled me along behind her. Only someone who observed closely would notice the ribbon went to my skirt and even then they would think it was just something that used to hold a balloon that I had tied to the hem of my outfit.
A TG&Y if you have never been in one was kind of like the original Wal-Mart. It sold appliances, clothes, toys, and was considered at the time to be something like a five and dime store on steroids. Thinking back now to how rinky-dink they were, I don’t think anyone envisioned a 24 hour super wal-mart back then.
Buddy and Lewis made a bee-line for the toy aisle where they started bouncing balls and playing with the toys. The aisle was always a mess, and it was kind of expected kids would come through like a tornado and tear it up.
I wanted to check out the balsa wood airplanes. You attach a rubber band to the propeller after carefully constructing a model of a German Messerschmitt or a Japanese Zero and then let them dog fight in the air.
My Aunt pointed to the pink section of the toy area and told me I could play with dolls until she finished her shopping.
“Jenny, catch!” Buddy threw a ball at my face.
I pushed it away instinctively. I wasn’t sure if that was an Eddie thing or a Jenny thing at that point.
“He is a girl; you can’t throw balls at him!” Lewis told his brother.
“SHE is a girl!” Buddy corrected him and threw a ball at Lewis. They continued to play and knock over stuff while I looked at the dolls.
It was a new experience for me. I had never looked at doll houses or Barbie dolls. It wasn’t something my parents ever bought for us because my brother and I were both boys, and I simply had no interest in them.
However, the doll furniture did look fascinating. There were these plastic Playmobil faerie playsets and a Unicorn horse on one shelf. It was like I was getting to see all the new toys that I had never heard of before.
I had seen Legos, I had seen erector sets, I had seen Lincoln logs, I had seen GI Joe, I had seen Micronauts, I had seen Star Wars action figures, and yes I loved all of those toys.
However, now I had a glimpse into toys that I had never taken the time to appreciate before.
A girl was sitting Indian style inside of a plastic mushroom house at the end of the aisle. This is an expensive playset with a door, a window and a little plastic sink inside.
“Come have tea with me,” she asked.
“Me?” I asked.
“Yes, silly,” the little girl smiled at me. I could see she was missing her front teeth. She had her hair in pigtails.
I walked over and got in the small play house with her. She had an imaginary tea set and poured me an imaginary cup of tea with it. I drank it with my pinky up, and that pleased her.
“My name is Lady Princess Ginger Wondermoney; how do you do?” she asked.
I was so nervous that I muttered: “I am Jenny.”
She giggled and shook her head no. “You can be anyone you wish to be in here. You don’t have to be your regular self. You can be someone else,” she laughed.
She thought I was REALLY Jenny and was giving me permission to be anyone else I wanted to be.
“I am still trying to learn to be Jenny, Ma’am,” I said.
“Oh wonderful, well my real name is Lydia, but while we are having our tea, I shall ask that you refer to be my imaginary name, of Lady Princess Ginger Wondermoney, would that be alright with you, Jenny?” she said in a very fancy sort of funny voice.
“Indeed,” I smiled.
Lydia giggled, and we had a fun time pretending to drink tea until my Aunt came to get me.
“Having fun, Jenny?” she asked.
“Yes, Ma’am,” I answered from inside the mushroom house.
“You see it is not all bad,” my Aunt told me to get out and say goodbye to my friend.
Lydia got out with me, and I told her “Goodbye Ma’am,” and curtsied. Lydia returned the curtsy much more deeply than I did and seemed pleased to have met me.
As we walked away, my Aunt told me I did not have to call her Ma’am since she was not older than me.
“It just felt natural, Ma’am,” I said.
“Good, you will call all women Ma’am from now on, I am proud of you, Jenny,” she said.
Once the shopping was complete, Buddy and Lewis announced quite loudly they had to go to the bathroom. I, too, had to pee, but I was afraid to say anything. I began to do the pee-pee dance like my cousins as I tried to hold it.
“Do you need to use the bathroom, Jenny?” my Aunt asked.
“Yes, Ma’am,” I answered.
“In future, you will be supervised at all times except during your milking in the bathroom by one of us. You are not to milk yourself without permission,” My Aunt spoke loudly enough that anyone passing by might hear her, but I doubt they would have understood what she was talking about. The words still gave me nervous butterflies of embarrassment because she was speaking so casually about masturbating myself to control my erections. The fact she didn’t seem to care who knew only increased my humiliation ten fold.
“Blair, take Jenny to the bathroom and hold the stall door open. She has five minutes, and Blair make sure she wipes her bottom,” my Aunt said.
Blair sighed and made a clicking sound with her lips like this was unfair.
“Blair, you volunteered to help, now you can either watch your brothers, or you can watch Jenny, the choice is yours?” she said.
Mei
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