Naked on Summer Vacation Sissy Summer SchoolChapter 6
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It was the Friday of my first week as Jenny and I had my hair tied in pigtails. I was now able to do my own makeup, although I was still pretty bad at it. I was fond of blue eye shadow and pink bubble-gum lipstick. I am sure I looked trashy like jail-bait. The makeup made me look a little older but mostly like a little girl who was wearing too much of it.
I didn’t get to choose my own outfits. That was fine with me because Blair knew how to make things match. She liked to pick frilly outfits that were way too small for even my skinny frame to wear.
I was wearing a simple powder blue tube top dress. It was perfect for the summer because it was light and airy. I had no bra, but I did have the lacey panties and the pink ribbon attached to my balls. My cock was tucked under me and taped with a small piece of duct tape.
Blair was walking me up and down the street while holding my ribbon. Even though my dick was tucked, the ribbon could still pull my balls, and anytime I didn’t walk as fast as she would like, she would yank it. I found myself looking at flowers and clouds and noticing the outdoors differently than I had as a boy. I was practicing in two-inch heels. I had been used to mary jane slippers with two inches of lift, but now I was clumsily trying to walk in a pair of my cousin’s old beat up white kitten heels.
A kitten heel is your basic curvy heel woman’s shoe. It isn’t as posh as a pair of ankle straps or stilettos. I still couldn’t master those.
Blair was annoyed because she would rather be in the house talking on the phone or watching television although she and my Aunt had a falling out earlier and Aunt Sam told her to take me for a walk to get out of the house. I don’t think Blair was in trouble. I wanted to ask if it was over training me, but I was afraid to talk to Blair unless she spoke first.
Manny and Franklin saw us walking and rode up to us.
“Hey Blair,” they greeted her with big smiles.
“Fuck off, Franklin,” my cousin looked straight and kept walking with me following.
“What ya doing?” Franklin followed along walking his bike with his feet while sitting on the banana seat.
“Walking my dog and talking to two monkeys,” My cousin became more annoyed and looked straight.
“I haven’t seen Buddy, Lewis, and Eddie for a while, where are they?” he asked.
I was shocked they didn’t realize I was Eddie. Had my transformation been that complete or were they playing along like Liz and Ann?
“If they were up your butt you would know it,” Blair answered them.
“Well, we just wanted to play cowboys and Indians, and no one wants to be Indians. The Donaldson want to play. You two could play too! I’ll let you be a cowboy!” Franklin obviously had a crush on my cousin.
“Let me think about it,” Blair put her hand to her mouth as if she were giving it a lot of consideration before saying blithely “It’s still a no from me.”
I chuckled at how funny that was. If I had said something like that before they would have beat the snot out of me.
“What about her?” Franklin asked if I was my cousin if I was interested in playing with them.
“She can speak for herself,” Blair turned to me.
“Let me think,” I put my finger to my chin “That is a no from me as well,” I smirked.
“Gosh, you two don’t have to be such bitches about it,” Franklin and Manny watched us walk away. I wiggled my butt a little extra as I did. I learned that heels naturally make me want to wiggle while I walk.
Blair didn’t say anything to me about what I had said, but the fact she didn’t punish me or make me do something humiliating in front of them made me think she liked what I had done.
When we got back to the house, she told Buddy and Lewis that Franklin and Manny wanted to play Cowboys and Indians and they were excited and asked their mom if they could play.
“Sure, take Jenny with you,” she said as she watched General Hospital. I was shocked she didn’t ask Blair to go. I looked at Blair to implore her to step in.
I had just told basically told those guys to fuck off, but Blair shrugged and told me “Sucks to be you, Jenny,” before trotting off to her room.
“May I change first, Ma’am?” I asked my Aunt.
“You can play in what you have on but put on some sensible shoes,” My Aunt said and let me put wear flats. I was used to only wearing sneakers and socks.
Florida has an abundance of what is known as sandspurs. These are little weeds that grow about ankle high and have tiny balls with thorns on the end that attach to your jeans or shoes and are hard to pull off. They also have red fire ants that bite the dickens out of you. Jeans and sneakers aren’t a lot of protection, but a short skirt and flats are even less.
Lewis and Buddy were eager to join up with Franklin and Manny. The Donaldsons were outside too. Lori had on a tank top, and jean shorts but her sister was wearing a short top and skirt. They both had on flats just like me.
“Indians! Indians!” Buddy and Lewis began to chant “Hi-Yi-Yi!” in anticipation of the game.
“She is playing too? I thought you said you didn’t want to play?” Franklin looked at me. They weren’t angry with me for my rude comments earlier. I felt a little guilty about making them. I was supposed to be learning not to be rude. I apologized for my rudeness and Franklins shrugged like he expected it from girls like me.
“Are you stupid or something? that is Eddie?” Crystal recognized me immediately.
Buddy and Lewis introduced me as Jenny. They regarded me as Jenny now all the time.
“Oh, it’s like Ronnie and Donnie McDonald, are you and he twins?” Lori asked me. She had to be putting me on. I wondered if Lori was just playing along.
“Yes, Ma’am,” I replied.
“She talks fancy just like Eddie,” Crystal snickered. She wasn’t buying for one second that I was a girl.
“Yeah, because they are twins,” Lori said and pointed out our faces would be the same.
“How can they be twins if Eddie is a boy, and Jenny is a girl?” George didn’t buy it either.
I flipped up my skirt in the front and pulled my panties down to reveal my little mangina before pulling them back up quickly. My cock was tucked behind me and all they could see a flash of some red pubic hair.
George, Franklin, and Manny’s eyes popped out of their heads in shock.
“You boys look like you’ve never seen a clit before,” I said with a satisfied expression on my face and puckered my lips.
That seemed to satisfy even Crystal.
Franklin told them there could be fraternal twins. He was always spouting off some trivia or useless knowledge.
“So where is Eddie?” she asked me.
“He had to go home,” I lied. I felt guilty about lying to Crystal. She was cute, but I was more embarrassed she would think Eddie (which I know is me) was dressed as a girl then I was to pretend I was Jenny.
“Why?” she asked in her sexy country accent.
“He was a little pervert who kept misbehaving, Ma’am,” I answered.
“You don’t have to call me Ma’am, my name is Crystal,” she smiled in a very friendly and inviting way. Crystal seemed to like me a lot more as Jenny then she ever did as Eddie. It may have been because we had similar body types or she just wanted a friend that was a girl about her own age.
“I call all women, Ma’am,” I said flatly.
“Then you should have said I call all women, Ma’am, Ma’am,” Crystal joked as we walked towards Franklin’s house to get the Cowboy and Indian stuff.
“Why don’t you call all men, Sir?” George asked, skeptically.
“I call all adult men, sir,” I explained.
“Why is it different for girls?” George seemed to think that wasn’t fair.
“My Aunt wants me to respect all women but not silly boys,” I answered.
“Y’all bitches want equal rights, but you don’t treat us equal,” George became angry.
“Yeah, we want the right to be equal, but that doesn’t mean we have to call your silly ass, Sir!” Lori defended me. It felt like I was in a sisterhood now because Lori and Crystal both were on my side.
Franklin said that Lori could not be a Cowboy this time despite Lori complaining a number of times that was not fair.
“You flipped us off and betrayed us and freed your sister last time!” Franklin reminded her.
“That was last time. This time it will be different,” Lori was clearly lying, but I think Franklin was buying it. “I want to be a cowboy!” she insisted.
“I think it should be boys are cowboys and girls are always Indians,” George was clearly the misogynist of the group.
Buddy and Lewis were happy to be Indians and didn’t want to be Cowboys.
Franklin said the game could not be played with three cowboys and five Indians.
“What if Crystal and I are ponies?” I asked.
This excited Crystal because she loved horses. I knew that from the last time we played. She had every reason to suspect I was really Eddie because how would Jenny know that? She didn’t care because as soon as she heard ponies, she was in on whatever game it was going to be!
“How would that work?” Franklin was intrigued.
“Crystal and I would be ponies. Whoever catches us can ride us, and we trot around the woods,” I described my vision of how the game would work. I liked watching her be a pony, and I was curious about what it would be like.
“So basically, you are just Indians?” Manny didn’t like the idea because we had to be caught.
“No, silly, we trot around and whinny If you catch us, then we are your loyal steed unless someone steals us,” I promised.
Once I introduced this new idea to the group, there was no way Crystal was not on board. She asked what we would wear enthusiastically.
I looked around Franklin’s room and found some things we could wear. I attached a hairbrush to a belt and made it into a terrible approximation of a ponytail.
Crystal asked what we would use for the pony bridle and bit. I wasn’t sure what ponies actually wore so after she described it as something we put in our mouths and bite down it was a simple matter to find a magic marker and hold it in our mouths longways like a horse’s bit.
Crystal asked if she could draw stars on my face and make me look like a pony while the others got dressed. Franklin thought it was going too far, but I agreed, and she got very close to me and brushed her body up to mine. Crystal drew stars on my forehead and cheek and then asked me to do the same.
“Now we are pretty ponies!” she said as she trotted and whinnied. I was super horny from being so close to her. Crystal smelled like candy strawberries, and her skin was so soft. She noticed my ribbon hanging down from my skirt and asked about it.
“That is my pony lead. You can use it to lead me,” I said and handed it to her.
“Don’t be silly, a pony can’t lead another pony!” she didn’t take it but found a cord she could use as a lead as well. “How do you keep it from falling out?” she asked.
“It’s in my panties, Ma’am,” I said, and when she smirked, I suggested she tie hers around her waist.
We trotted together as the others walked to the woods. If you have ever seen Monty Python’s quest for the holy grail, it was quite a bit like how their knights skip along, and someone runs along behind making the clopping noises except we made those with our mouths.
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