Naked on Summer Vacation: Sissy Summer School
Copyright© 2019 by Eddie Davidson
Chapter 11
That morning I woke up to the sound of my Cousin groaning above me. She had a hangover, and although I had no experience with it personally, I knew that my Aunt had them after drinking too.
“Good morning, Ma’am,” I said from the bottom of the bed. I usually waited for my Aunt or her to unbind me to start my morning rituals around the house.
“Don’t be so chipper, Fart face,” she called me. I was used to the names my Cousin liked to call me. Blair was quite creative, but fart face was one of her favorite names to refer to me.
“Sorry, Ma’am,” I said.
“What did mom say when she got home?” Blair asked me in a whimpered haze.
“I don’t know Ma’am, I tied myself to the bedpost and went to sleep after I ate your pussy,” I smiled.
“You did what?” she asked incredulously, and then when I began to repeat what I had done, she told me she heard me the first time. She dropped down from the top bunk. I could see her naked feet from under the bed. She squatted down and crooked her, eyebrow, “How dare you take advantage of me when I was drunk! You are going down for that!” she was livid. She raked her fingernails across my chest, angrily.
“You told me to come lick your pussy, Ma’am!” I said apologetically as I struggled to defend myself from her cat-like claws while still having one wrist bound to the bedpost.
“Okay, I vaguely remember doing that,” Blair admitted and withdrew her sharp fingernails from my body. She didn’t apologize for getting angry with me. “I hope that was ALL you did?” she asked.
“Yes, Ma’am,” I said as she reached under the bed to untie me.
“Well, that was the first and last time you’ll get to lick my pussy, so I hope you enjoyed it,” she said with a cruel tone.
“Yes, Ma’am, I licked front to back as you showed me,” I said.
“Gross, you licked my booty hole too?” Blair started getting dressed. “You can come out of your hole, rabbit,” she told me. Usually, she told me to wait until she was dressed before I could come out.
I crawled out from under the bed and stretched. My Cousin was still mostly naked and shrugged.
“Listen, I remember doing a lot of things last night, and some of them were out of line. I am sorry about that, Jenny,” she said.
“You called me Eddie, last night Ma’am,” I pouted.
“I know, but you are Jenny until my mom says otherwise. I am trying to apologize, and you aren’t making it any easier,” she said as she stood naked before me. I tried not to get aroused, but I wasn’t having a lot of luck. She smiled when she noticed my red face as I looked at my toes.
“Look, what happens when I babysit will be between us. I’ll make it up to you tonight. We are going to have a little party. You can dress like Jenny, and as long as you are behaved and keep our secret I will let you play spin the bottle and any other dirty little games,” Blair pulled my chin up so that I could look her in her pretty blue eyes. She had the cutest upturned nose and smirk on her face. She also had perfect puffy nipples set against her smallish boobs.
“We are going to be roomies. Mom let you look at Liz’s butt at the beach, didn’t she? You had your curiosity satisfied. Okay, well take a good look,” Blair stood there and let me admire her naked body. Her tits were shaped like water balloons that jutted straight out and what fascinated me was that her nipples were so puffy.
I would much later in life realize that my Aunt had a boob job, and that is why her tits looked like basketballs sewn into her chest. However, my Cousin Blair’s smallish tits were all natural and perky.
What I could see of her pussy was a thick bush of long curly hair that was trimmed on the sides but wild and unkempt in the center. There was a small line that looked like lips on a face only sideways at the bottom of her pussy. Crystal’s pussy was higher on her crotch and was much broader like a Hibiscus blossom that hadn’t fully opened. It was odd to me how different women’s vaginas were from each other.
Blair had a bubble butt, and she let me look, but she didn’t pull her cheeks apart for me.
“Okay, satisfied?” she asked after letting me ogle her.
I wasn’t. I could stare all day, but I said I was.
“Good, thank you for helping clean up. That was unexpected. You could have got me in trouble, so I owe you one,” Blair promised me. “I am going to have to beat you and discipline you. I will still be hard on you, but I am sorry that I got a little carried away. You did make a good puppy, though,” she said.
“I kind of enjoyed it, Ma’am,” I told her and she said I was weird.
I told her how about how we played pony when I was outside and how I was considering using the hairbrush as a tail. I explained that I felt terrible that I couldn’t go naked but that I was afraid they would not understand when they saw the duct tape and realized I wasn’t a real girl.
“You could just say you have your period, but that won’t last long,” she shrugged.
I didn’t know what a period even was.
“I have the perfect thing,” Blair smiled smartly and showed me her cheerleader stuff. She said that she used to be interested in all that “Rah-rah sis’s boom bah, stuff” but that she had other interests now. Blair handed me one of her pom-poms. There were colorful blue and white streamers attached to a handle. She had two sets of them.
“What should I do with this Ma’am?” I asked.
“Stick it up to your butt,” she said.
Ordinarily, I would assume she meant that figuratively and not literally like I should basically fuck off. She meant it literally.
She spit on the handle and rubbed her hand around it like she was milking it twisting and turning until she coated it. She told me that I could cum all over it, use lotion or anything as long as I didn’t wear it dry. “Although you may like it, I don’t know,” she told me to get in the thermometer position.
I did as instructed with a curtsy, and just like a colossal thermometer, she slid the rounded tip of the handle into my asshole right to the base. The end result was a gorgeous, shiny, ponytail that I could shake.
Blair noticed the marker on my face and how my nipples were red from where she drew on me. “I have a few other things you can use,” she said.
She gave me some cheap clip-on silver hoop earrings that were very popular at the time. She clipped them to my nipples, and they stung but in a good way. Blair gave me some leather belts and the leather collar I had worn the night before. She showed me how I could put black leather the belt in my mouth and then bite down in the center like a bit. Then she grabbed both ends on either side and turned my head back and forth like they were reins.
“You’ll have to give me some time to come up with a saddle or some shoes, but this should get you started,” she giggled as I shook my tush for her.
I thanked my Cousin profusely and forgave her for treating me roughly the day before.
“You are a tough little bastard; I’ll give you that. I thought you would cry when I stepped on your balls. I thought you might bite me when I put my ass on your face. You know I farted silently, didn’t you?” she said.
I hadn’t, but now I did. If that was what girl farts smelled like I was okay with it.
“The only part I really didn’t like was when you made me eat off the floor and calling me Eddie, Ma’am” I admitted.
“What about when I made you eat your own cum with a spoon?” Blair seemed particularly proud of that.
“I hate to admit that I liked the taste. I milked myself after I ate your pussy and then licked it all off my hand afterward. I know I should be punished because I didn’t put it in a tissue, Ma’am,” I admitted.
“I was in charge of you, and you used your best judgment. I will let you eat your cum when you milk yourself while I babysit,” she smiled at me playfully. I was astonished about how nice my Cousin was acting. I wondered if it was an act - Blair seemed so sincere.
“Yes, Ma’am but Aunt Sam said that a lie of omission is still a lie. If I don’t tell her that I do things differently then I am intentionally deceiving her,” I said.
“Then, you blame me. If my mom asks you if you eat cum when I babysit, then you say that I told you that you could, and I will handle it. I am the elder, and it is my responsibility,” Blair said. That did seem reasonable.
“What if your mom asks if boys come over, Ma’am?” I asked.
“That would be different. That is my lie of omission, not yours. If she comes to you and specifically asks you about these particular boys, then she already knows, and I am in deep shit. However, don’t volunteer anything to her. If you can do that, then I can be a very good roommate. If you cannot then I will find things to stick up your ass that even a freak like you won’t enjoy. Deal?” she asked.
I hesitantly accepted the deal. She told me to go milk myself but cum in a napkin, and then I could get breakfast ready and stand in the living room for my beating. I removed the pony things she had loaned me and put them in a box. Blair told me to make sure always to clean whatever had been in my ass with soap. I obeyed her cheerfully.
I was strangely happy for a return to the regular structure, and I was over the moon that my Cousin was now an ally and not an enemy. She got dressed and went to wake up her mother.
I had a relaxing spank in the bathroom while I flicked through the many mental images I had collected over the last few days of naked women. I continued to mostly think back to Crystal’s slick pussy and whether it would taste like Blair’s juicy pussy if I licked it or not. It didn’t take long for me to spunk into the tissue. I didn’t even need lotion at this point. It seemed a shame to waste the cum, so I did dab a little on my finger and rub it on my asshole. It felt good. I brushed and did my hair in pigtails and applied a fresh coat of makeup as well.
My Aunt came walking out of her bedroom in just her white robe. The robe material was made of a netted mesh that allowed you to see her skin, but you couldn’t actually see her nipples or pussy through the tiny holes. It was still very sexy that she wore it so frequently around the house.
“Ah, coffee, thank you, Jenny,” my Aunt went to the coffee maker I had started and poured herself a cup. She looked hungover as well. Her hair was all fucked up, and she had several bruises on her arm. “Thank you for cleaning up around here as well.”
“You are welcome, Ma’am, thank you for the education,” I smiled. I didn’t want to seem like a brown-noser, but on the other hand, I had always been the kind of person that wanted to be the teacher’s pet.
“How do you know I didn’t clean up around here?” Blair asked when she walked in.
“The house has never been cleaner since Jenny started training and I remember what it was like when you babysat before. The entire house was a wreck. I am hesitant to send Jenny back home when Summer is up,” my Aunt smirked at me and tousled my hair.
I showed her my tissue, and she sniffed it and then told me to throw it away. I curtsied and took my semen to the trash as I normally did. Then I started to remove my panties in the living room and wait for my punishment.
“Wait a little while, Jenny,” my Aunt said that I could eat breakfast with the family this morning because we had guests and she didn’t want them to see my punishment.
I had been told I would be punished no matter who was over, but I resisted the urge to back talk and remind her of the rule. I thanked her for her generosity and asked how many more plates should I set.
A man came walking out of my Aunt’s bedroom. He was different than the one who was there Tuesday morning. He was thin and had a beard.
“This is Jerry, he is an old friend,” My Aunt looked a little embarrassed. Jerry was not a very handsome man, and he looked shifty.
“I remember you from the beach, Sir,” I said.
“Oh, the pretty little girl standing in the parking lot with her hoo-hah out,” Jerry took a big interest in looking at me. “I’ve never seen nipples that color!” he said.
“It was just magic marker, Sir” I admitted. My Aunt glared at Blair, but she shrugged.
“Well, maybe sometime I could take you out for ice cream or something,” Jerry smiled at me. He had a creepy smile that put me off.
“I don’t think so Jerry this was probably a one-time thing,” my Aunt told me as she sipped her coffee.
“You said that last time,” Jerry had a cocky swagger to him. Unlike Jack, who seemed to deserve to have that swagger because he was handsome and strong., Jerry just looked like he was pretending. “You know what I think? I think you say you like coffee, but you just like the creamer!” he said. He blew me a kiss and left.
“Gross,” Blair shuddered after he left. “He used to want to take me for Ice Cream too when you dated him,” she said to her mother. My Aunt was about to say something snarky and funny in response when her bedroom door opened again.
Liz walked out of the bedroom. Her hair was also fucked up. She was wearing a man’s shirt and no bottoms, but it was long enough to cover her pussy and ass. She had bruises all over her legs, and she looked hung over.
“Is he gone?” she asked with a wry grin.
“Yeah,” my Aunt offered a cup of coffee to Liz.
“Did he give you the same speech he did to me about wanting coffee but really liking creamer?” she asked.
“Yeah,” my Aunt agreed.
My mind was very electrified with the possible reasons that two women were in the same bed with one man. There were so many sexual scenarios in my mind that I was thankful I had just milked myself.
“Well, hello, Jenny! Your mom tells me you have been cleaning up the house and doing book reports. I wish you lived down here. You’d be a fun student for sure,” she said.
“Yes, Ma’am, I wish I did too,” I really did wish that at the time.
“Good morning, Blair, you’ve really blossomed since you were in my English class,” she said to my Cousin.
Blair was about to say something snarky or funny to that when there was a knock at the door. My Aunt sent Blair to answer it. I was often sent to do things around the house or fetch things, but I was never to answer the door by myself.
Franklin, Manny, and the Donaldsons were in the doorway. I assumed they wanted to see if Buddy and Lewis could play. My Aunt told them they were still asleep and didn’t have their breakfast yet.
“We were actually wondering if Jenny could come out and play,” Franklin said and looked past her at me. I was in nothing but panties sitting at the kitchen table. I waved.
My Aunt looked impressed that kids were requesting to play with me - or at least with Jenny. I was impressed too. I wasn’t very athletic or outgoing as Eddie, and where I lived with my parents, I mostly stayed inside. No kid in my memory had ever come to the house looking to find me to play with them.
“What are you going to play?” my Aunt seemed skeptical for a moment.
“Horsey!” Crystal shouted gleefully, and they all smiled. They told her that Buddy and Lewis could meet us at base camp after they have their breakfast and asked to please let me come out.
“Normally, Jenny has some things she has to do in the morning, but I’ll make an exception if you wait outside,” my Aunt closed the door on them and came over to me.
“Jenny, you’ve really exceeded my expectations. I was going to have a talk with you about last night because you were not home when I left. You are still in discipline, but I think playing will be good for you. Do you want to play?” she asked me.
“Yes, Ma’am, I would love to play,” I smiled.
“You have definitely changed,” she looked at me and told me to stop wasting time and hurry up and get dressed. She sent Blair to pick out my outfit.
Blair asked me what I wanted to wear today. She was very different now as well and told me I could be as late as I wanted because my Aunt would be going out again and she would cover for me. “Just let me know and check in with me,” Blair said.
“It doesn’t really matter what I wear because ponies are naked,” I was planning to play naked. Blair put me in a short skirt and a tank top and gave me the box of pony stuff. She kissed me on the cheek and told me to have fun. This was definitely not the wicked Cousin from last night.
When I came out into the living room, my Aunt was talking to the kids. I was worried they would tell her too much about the game and she may cancel it.
“So, you never go to the beach?” My Aunt asked the Donaldsons.
They told her that since they moved here a year ago their parents haven’t taken them because they are fair skinned and burn easily.
“If you ask your parents I’ll be happy to take you this afternoon, would you like that?” my Aunt smiled at them. Manny and Franklin said they weren’t interested, but the Donaldson wanted to go. That would mean I would be naked in front of them anyway when I changed into my suit or took it off to shower.
“I got a question for you,” George asked in his deep hick accent. “You seem like one of them there women-libbers like Anita Bryant?” he asked her.
“Not really and I don’t think Anita Bryant is a woman’s libber but what is your question?” my Aunt had a trace of a playful smirk on her face like she was expecting a funny question.
“How come Eddie had to go home, but Jenny got to stay?” he asked her.
“Well, Eddie was a handful and a lot of trouble, and we liked Jenny better,” my Aunt smiled at me with a rueful grin because technically she wasn’t lying. They had sent Eddie away, and now I was Jenny.
“Well, then how come if you like Jenny so much you make her call all women Ma’am, but then if you believe in equal rights and all that she doesn’t have to call all men Sir?” he asked.
“Jenny has to call all women Ma’am and all men Sir,” my Aunt said, “because it is respectful.”
“Well, she said she had to call my sister Ma’am, but that I was a silly boy and she only had to call grown men Sir!” George seemed angry that this was not fair from his perspective.
No one else in his friend’s circle seemed to care one way or the other.
“Would you like Jenny to call you Sir?” my Aunt asked him with that smirky-grin like she is thinking of something witty to say.
“Hell Yeah! and tell my danged old sisters to do the same thing!” George demanded.
“I can’t control your sisters, but Jenny, you know that George is older than you. You will refer to your betters as Sir. That includes Franklin, Manny, and George, is that understood?” she asked.
“Yes, Ma’am, I am sorry,” I answered.
“Apologize to them,” my Aunt didn’t want me to apologize.
“I am sorry, Mr. Franklin, Mr. Manny, and Mr. George, I should never have called you silly boys. I will call you Sir from now on! please accept my apology.” I said.
“You will be punished after you get home,” My Aunt didn’t want to spoil the fun by making everyone wait for a spanking, but she made it clear I would be spanked for that. I had assumed she didn’t mean boys near my own age, but she had.
“That means she’s got to do what I say, right?” George asked for clarification on just what being called Sir entitled him too.
“While you are playing then you will listen to the older kids and do as they say unless it is sexual, dangerous or they are telling you to cheat, steal or lie. I assumed that was implied, but obviously, I need to tell you these things, don’t I Jenny?” my Aunt said sternly.
“Yes, Ma’am, I am sorry,” I said as I held the basket of pony toys.
“What is in this basket?” she asked me.
“They are pony toys. Blair let me borrow them,” I said.
My Aunt looked over the items and cocked a curious eyebrow at Blair. “It isn’t like Blair to be so generous,” she smiled and told me to go play with my friends. “We’ll talk about all this later,” she assured me.
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