Naked on Summer Vacation: Sissy Summer School
Copyright© 2019 by Eddie Davidson
Chapter 8
That night I dreamt of being a girl for real. I dreamt of having a Malibu Barbie car and driving to the beach. I dreamt of getting married to a husband. I awoke to feel strangely guilty because technically that made me “gay” and yet at the same time because I had been a girl in my dream I was not gay since I was a woman.
It is strange how sometimes you have a dream so real you want to go back to sleep and see how it turns out.
I awoke with a raging erection, and I asked Blair if I could milk myself.
“Gross, Eddie! Let me sleep!” she groaned.
“It is Jenny, now Ma’am,” I said seriously.
“You keep telling yourself that,” my Cousin was not a morning person. I can tell you that. She definitely looked like a boy when she didn’t have her make up on in the morning. She also had stinky breath, just like Buddy and Lewis. Sleeping in her room was teaching me that girls farted too. I heard her all night.
“Yes, Ma’am, I’ll go ask Aunt Sam,” I said.
“Good luck with that,” she said.
I knocked on her door, and when she didn’t answer, I opened the door.
My Aunt was naked with a man in her bed that I didn’t recognize. He rolled over and saw me and then said, “Your daughter is in here,” he pulled the covers over their bodies.
“That’s not my daughter, that is Eddie,” my Aunt said before correcting herself and saying I was her niece.
“Well, hello Eddie, you should probably put on some clothes,” he said.
“She is only allowed to wear panties because she is on restriction,” my Aunt explained and snuggled into her pillow.
“What did you do Eddie?” He asked me. He had a deep country accent like the Donaldsons.
“I peeped on my cousin and sniffed her panties, Sir” I admitted.
“You are one weird girl,” the man sat up in bed and looked at me.
“Are you a boy?” he asked. I had put my hair in pigtails and still had on some of the makeup from before, but he may have noticed the flat chest and the little bulge in my nearly see-through panties.
“No, she isn’t a boy, come back to bed. Jenny, go get breakfast ready for your cousins, and I’ll be out in a minute,” she said.
“I thought you said her name was Eddie?” I heard the man say as I shut the door.
I was hoping to milk myself because I really didn’t want to get in trouble for an erection, but I had been told to prepare breakfast.
I poured orange juice for everyone and set the table for my Aunt, her guest, and my three cousins. I set up cereal and put out the milk and started Coffee. I had seen my mom do it, and the coffee pot looked similar. I was putting silverware on the table when my Aunt came walking out of her bedroom, yawning. She didn’t cover her mouth.
“I read in the etiquette book you gave me that you are supposed to cover your mouth when you yawn, Ma’am,” I reminded her politely.
“You were doing so well last night, and now you sound like a little know it all. I suppose we’ll have to strap you after all,” she shook her head at me. I was sad I had disappointed her.
“Never correct your elders like that or speak out of turn, Jenny. Now, what you saw in that bedroom was none of your business either. If I don’t answer my door, then do not come in unless the house is on fire?” my Aunt instructed me sternly.
It was shortly after that she noticed I had set the table and put the Coffee on and her face brightened. “You did this by yourself?”
“Yes Ma’am,” I thought it was a reasonably simple spread, but I laid out the forks, knives, and spoons in order on napkins. My Aunt smiled at me.
The man who was in her bedroom didn’t stay for breakfast. He came out of her room in a cowboy hat, denim jeans, and boots. He doffed his hat to me and didn’t look right at me. I am glad because he may have noticed my erection in my panties.
Once he left, she told me I could milk myself and come to breakfast. “May I ask if it would be alright to see your boobs again, Ma’am?” I asked.
My Aunt was put off at first but a little flattered. She opened her robe and flashed them to me again and winked “Don’t make a habit of spanking it to your Aunt, Jenny!” she grinned as I walked away with the image of her freckled, firm, well-rounded tits firmly burned in my head.
I jerked off and showed her the napkin.
“In future, you may come out of the bathroom naked with the assumption you will receive a strapping right after unless told otherwise, Jenny” my Aunt had her Coffee and was sitting in her wobbly kitchen chair like the Queen of Narnia talking down to a quaking Mr. Tumnus the goat boy.
“Yes, Ma’am,” I removed my panties and went to the living room to wait for my spanking.
My Aunt continued to sit at the table and drink Coffee while I stood there quietly in the living room, waiting for her to come to spank me.
I cleared my throat in case she had forgotten me.
“It is rather rude,” my Aunt said after a pause “to clear your throat to get my attention, don’t you think? You may stand like that until breakfast is finished. Then I will apply you your morning discipline, and you may put your panties back on and clear the table and eat your own breakfast, Jenny.”
“Yes Ma’am, thank you” I stood there in awe of her. She always had a ready answer and a plan for me. I should have been deeply humiliated or offended, but I was excited, although my dick was not hard. I was excited to get on with the day and see if I could improve my behavior. I was no longer even concerned if my parents knew about this. I assumed they would find out for sure and I had no reason to believe this form of discipline was really altogether any more unusual than I did little boys showering naked at the beach after a hot day. Everything was all new to me, and I accepted it for what it was as it was presented.
The others woke up slowly, and Buddy and Lewis laughed at me, standing in the living room like a statue in the nude. Blair was the last to get up, and she sat at the table and ate.
When they finished eating Blair offered to clear the table, but her mother said I would be doing that from now on. “Jenny will set the table and clear it. She will eat afterward,” her mother said sternly. I was also provided two teaspoons of my Salt Peter.
I received my morning discipline of twenty swats from my Aunt, and I ate quietly after I cleaned up the table and the kitchen. I don’t want you to think this was a Cinderella story where the wicked cousins and Aunt has fun, and I am left to do the chores.
I also don’t want you to think that I was this perfect sweet angel. I didn’t want to clean up, and the strapping hurt a lot worse the next day because a lot of it was across my dick instead of the natural padding of my bubble butt.
As an example, once we were all cleaned up, we got in the car to go to the beach. I had to ride in just panties in the hump seat.
Once we got to Wendy’s where my Aunt liked to park at the beach, it was a lot busier than it had been on Monday. She told me to get out of the car, strip, and put on the one piece french-cut girl’s swimsuit.
I turned beet red in the face at the idea of getting out of the car naked in a busy Wendy’s.
“Jenny! Do I need to get Tyrone?” my Aunt insisted.
“No, Ma’am, sorry!” I stepped out of the car. The ground of the parking lot was scorching from the Florida sun. My cousins were used to walking on it, but I wasn’t.
“FU-UH-UCK!!!!!!!!!!” I shouted as if I had stepped into molten lava.
My Aunt grabbed my ribbon and pulled me into the Wendy’s. She took me straight into the women’s bathroom. There was no soap bar to stick in my mouth, so she pumped three squirts of soap in her hand and made me lick it off her hands. It was disgusting.
She marched me through the Wendy’s in panties, and people looked up with amused expressions on their faces. Parents who were thankful their children weren’t such brats seemed happy I was being dealt with.
Now, instead of just the possibility of someone nearby noticing a bare butt wiggling out of the backseat of the car to put on a bathing suit the entire parking lot could see the whining, bratty girl being led back to the car where my Aunt insisted I undress.
I still had to walk on the super hot pavement, and I wasn’t happy about it. My Aunt spanked my bare bottom with her hands and insisted I put on my swimsuit. I tucked my penis under me and quickly put it on but not before a white van pulled up alongside us.
The man in the passenger seat whistled and called me a “Pretty little thing.”
“Stop being such a perv, Jerry! You couldn’t handle a real woman, so you look at little girls!” My Aunt flipped him off. We were in a small town, and there was a good chance almost everybody knew everybody.
Jerry didn’t respond. The van drove away. Blair flipped him off as he went, but my Aunt glared at Blair. “It is okay for me to do it but not you,” she said.
Blair looked sullen, and she jerked my ribbon. It was still on my balls even though my penis was tucked in between my butt crack like a little tail.
“Carry the stuff to the beach, turd” Blair instructed me to pick up the towels, cooler and chairs and carry them.
“We’ll all carry them,” my Aunt had everyone help. Even Buddy and Lewis brought their beach balls and pail and shovel to the beach.
That afternoon I played on the beach like I was a girl and no one batted an eye or questioned it. I had very minimal makeup on my cheeks and pigtails so for anyone who didn’t know me I was a girl.
Blair was told to rub lotion on my shoulders and body. The best part was I got to rub lotion on Blair. I got an erection half way through but because it was tucked into my butt other than discomfort nobody knew.
I was tempted to tell my Aunt I was aroused. I was supposed too. I knew I should want to change and volunteer for discipline. I was also having fun on the beach, and I didn’t want to get in trouble, so I didn’t say anything.
Towards the end of our trip to the beach, Liz and Ann showed up. They were walking together and talking. They smiled at my Aunt and started talking to her. My Aunt was laying out in a revealing two-piece bikini and enjoying a cocktail when they walked up to her.
“Jenny, come here,” she shouted for me to stop playing and come see them. I turned a little red-faced because they knew me as Eddie. I wondered how they would react.
Ann the blonde was wearing the same skimpy wet bikini she had on the last time I saw her.
Liz, the brunette, was wearing a thong bikini. It was the first time I had ever seen a thong bikini. The top was normal, and it covered her boobs and tied in the back. The front was a simple V that covered her female parts well enough. However, the back was just a string that revealed both of her butt cheeks completely.
It was very distracting, and I wanted desperately to stand behind her so that I could look at her butt. However, she insisted on looking down at me. Liz and Ann were trying to contain the mirth on their faces.
“Hello Jenny, it is nice to meet you,” Ann pretended she didn’t know it was really me.
“Hello Ma’am,” I curtsied and held up invisible skirts as I had been taught. I wiggled a little as I pivoted smartly on my left foot for them.
Liz and Ann couldn’t contain their giggles.
“How do you like your new swimsuit?” Liz asked. She knew it was really me in pigtails and was just playing along.
“I like it very much, Ma’am, thank you for inquiring,” I said.
“Ooh, I do hope you move down here when the Summer is over. I’d love to get you in my English class! You could bring up our testing scores!” Liz liked my choice of fancy words.
“Thank you, Ma’am, but I’ll go back to being Eddie when the Summer is over, and I think my parents will be picking me up soon,” I said. I remembered my Aunt said she would call them as soon as they arrived at the hotel.
“Would you like to go back to being Eddie?” Liz asked me. She was a little more serious this time.
“No, Ma’am, not until I’ve learned what it is like to be a girl,” I admitted. I knew it wouldn’t do any good to pretend I was someone else with her.
“Well, you should probably let him stay then,” Liz turned to advocate for me to my Aunt.
“I don’t see any him? Who are you talking about? My niece, Jenny?” My Aunt smirked playfully. “I will tell your mother about your punishment but in my own good time, Jenny. I feel comfortable you will be dealt with appropriately when you misbehave and are learning a valuable lesson here,” she said.
Liz and Ann both smiled at me, and I smiled back.
“Speaking of which can you explain why you keep angling yourself so that you are standing behind Mrs. Sonneborne?” My Aunt asked me sternly about why I had been trying to angle myself behind Liz to get a better look at her butt.
I instantly denied what I was doing, and all three women chuckled.
“You told me you would be honest with me, Jenny. You even told me you understood what lies of omission are and yet here you are lying to my face in front of my friends,” My Aunt was smirking but disappointed.
“Yes, Ma’am, I am sorry, Mrs. Sonneborne, I was trying to look at what you had in the back. It didn’t look like you had on anything at all,” I said.
“Were you curious, or do you like oggling older women, Jenny?” My Aunt asked somberly.
“Hey, watch who you are calling older women,” Liz joked.
I was expecting a punishment, and I braced myself for what would be an embarrassing lashing and a humiliating end to my day at the beach.
“Well, come around here and get a good look, Jenny. Liz, you don’t mind, do you?” My Aunt surprised me by suggesting I just walk behind her and have myself a good, long look to get it out of my system.
Liz did look like she minded until Ann reminded her that she chose the outfit and just about every eligible bachelor and some married men in Sebastian County (where we were) had already seen it.
I was reluctant, but after a little coaxing, I walked behind Liz and had a good look at the two mounds of tanned flesh that I had been trying to get a good look at since I walked over to them.
Liz’s ass wasn’t perfect. Her ass was a little flabby with a tiny bit of cellulite around the bottom. You could see a few veins and even a bruise on her ass when you looked closely. I could see a couple of long black hairs sticking out of the crack of her ass on either side of the black string that ran between both cheeks. I could also see the very outline within her crack of what I assumed was a butthole. This was the ultimate taboo to me. The place that girls fart and poop from. I knew I wasn’t supposed to be looking at it, but look I did and memorized every inch of those buttocks.
“You’ve already had two punishments today, Jenny plus your normal discipline. The only thing that is going to satisfy your curiosity is to get a good long look. I think you’ve had that look, now thank Liz and put your eyeballs back in your skull,” My Aunt said.
I thanked Liz, but I continued to stare longingly at those butt cheeks. I wondered as her butt toasted in the sun what was inside her ass. Did she have dried poop inside of her butt waiting for the next time she had to use the toilet? I wanted to pull her butt cheeks apart and sniff and see what was inside the crevice. I know that sounds creepy, but that is where my curiosity about the female anatomy took me that afternoon.
“I don’t teach Sex Ed, so I am not going to hold them apart for you, Eddie,” Liz giggled.
“Jenny, remember?” Ann chuckled and reminded Liz that I was Jenny. Then Ann placed a reassuring hand on my shoulder.
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