Silly Sissy Chrissy

“Wakey wakey sunshine!” Tori and Charlotte were standing at the door way. “Another day, another swimsuit and outfit! You’ll love what were saved for you tonight! It’s sooooo cute and totally you!” I slowly arose from the bed, still vaguely remembering what exactly the girls were talking about.

“Oh, okay. I just need to hop in the shower and I’ll be ready.” I headed into the bathroom and started running the shower. In the mirror, my blonde hair looked a bit more luscious than usually. The tanlines from the bikini stood out a bit more too.

I got into the shower and cleaned myself of using Tori’s shower soaps and shampoos and came out smelling like flowers and vanilla. As soon as the shower was off, the girls came in to start working on my look for the day. Charlotte applied some lipgloss and waterproof mascara while Tori worked on adding layers into my shoulder length hair. On the bed was a white one piece swimsuit that had an open slit in the middle, leaving my stomach exposed. After the girls were finished, I grabbed the swimsuit and put it on in the bathroom.

“This really can’t be me, I don’t even have a resemblance of a boy.” I ran my hands through my hair and felt the swimsuit tight on my body. I turned around to check out my booty. Without thinking, I bent my hips and started shaking it. Feeling the suit go right in between my cheeks felt like something I had never felt before. I felt like a baddie.

I came out of the bathroom to cheers and whistles from Tori and Charlotte. I gave them a spin and put on my flip flops to head to the beach. It was more of the same as yesterday, just laying around tanning and chatting. There were a group of guys throwing around a football that caught Charlotte’s attention. “I bet they’ll “accidentally” throw the ball in our direction so one of them can come over and talk to us. Chrissy, maybe one of them will come talk you up.” She said in a joking manner.

“Oh yeah, and I’ll flaunt over him and giggle at all of his jokes and twirl my hair.”

”See you already get the assignment!” Tori joked. We all laughed and laid back on our towels. At the end of the day, we packed up our stuff and headed back into the hotel, walking straight past the group of guys, who were sitting around drinking. Instinctively, I started swaying my hips a bit more, showing off my butt in the swimsuit. Walking by, I turned and saw one of the guys taking a peak at my booty and I couldn’t help but blush.

We got ready for dinner, the girls set out a dress of a beachy skyline with a firey orange-red purse and platform flip flops. We ate a cute beachside restaurant, sipping fruity cocktails and soaking in the view. When we finished dinner, we headed down to the beach to get some pics. Tori pointed a head, “Ooo let’s do pics at this staircase up here!” Charlotte and I followed Tori to the staircase. “Ok Chrissy, you first!” Tori gave me her sunglasses and Charlotte helped me pose, looking away from the camera, holding my purse over my legs, fixing my hair. “Perfect, stay right there! You look so hot!”

While Tori was snapping pics, I couldn’t help but notice the group of guys sitting at dinner on the patio of a restaurant a few buildings down. I quickly spotted out the guy who was staring a me when we walked past, wearing a white shirt that showed off his arms. “Earth to Chrissy,” I had completed spaced out looking at the guys, “save some golden our for us girl.”

*Hey babes! Gonna start making some more longer sissy stories along with normal captions! Let me know if you like them and any ideas! Ok, onto the story ❤️❤️ - Chrissy*

“I can’t believe the trip finally made it out of the group chat! This is going to be awesome!” We got our bags off of the carousel and headed towards a taxi to take us to our hotel. I dragged my navy blue suitcase behind me as Tori and Charlotte got matching pink suitcases for the trip.

“For real! When we get to the hotel let’s just drop our bags off and go to the beach real quick before dinner” Tori said as the driver loaded our bags into the taxi. “And we can get some pics of the sunset! Why else would Chris be here?”

“Hey, this trip was my idea! One last thing with the three of us before we go our separate ways for work. I mean this’ll be the first time we’re more than a street away ever.” The three of us aren’t related by blood but we were the only kids in our neighborhood so we essentially grew up together. They always helped me pick up girls and the returned the favor when they wanted to find out more about potential guys. We even went to the same college together. But next week, Tori is going to Paris for Art School, Charlotte is going to New York for her finance job and I’ll… well I’m still waiting to hear back from jobs.

The driver pulled up to our beachside hotel. I went in to check us in as the girls and driver gave our bags to the bellhop. I got our room keys and headed back out to the girls, who had just paid the taxi driver. “Ready to head to the beach?” We headed down the path which opened onto a white sand beach. We stood on the beach in silence for about 5 minutes, just admiring the tranquility of the turquoise water smoothly landing on the white sand.

“Ok, everyone get in!” Charlotte whipped out her phone for a selfie, “I’ll send this to our parents! Everyone say “Beach Trip!”

“Beach Trip!” *SNAP*

“Ok, now Chris get some of me and Tori.” Having been through this many times, I made sure to get all of the angles and poses.

“Do you three want me to get a picture of all of you?” A girl about our age asked, “I saw you guys getting a selfie from the path.” We agreed that one more picture wouldn’t hurt. The girl introduced herself as Sam and we all introduced ourselves too. The girls made it perfectly clear that I was single and not with them.

We headed off the beach and to dinner. After dinner, we headed up to the room for the first time. I opened the door to see a living room that opened to a balcony with two bedrooms on either side of the living room. “Whoa, this place is so nice!” We all walked into the room on the left where a pink suitcase was neatly set on the side table. “This one must be one of ours,” said Charlotte opening the bag to her clothes falling out, “y’all’s must be in the other room.”

We walked over to find the other room and exact replica of the first, with a singular pink suitcase on the side table. “Ok, where is my suitcase at then?”

Halfway out the door, Tori said, “You two search up here and I’ll go to the front desk and see if there was a mix up with another room.” A few minutes passed and Charlotte and I had searched every room, closet, and drawer to no avail. “The front desk said there wasn’t a mix up but they’ll ask around to see if they find any suitcase anywhere.”

“What am I supposed to do?! All of my clothes were in there! The only thing I have are the clothes on my back!”

“We can go out early tomorrow and see if we can find some tee shirts and swim shorts.”

“Okay yeah, you’re right, we better get some sleep if we’re going to be up early tomorrow.” The girls took one room and I took the other. I could hear the girls talking from across the room as a drifted off the sleep.

The next morning I woke up and headed into the living room, in the same clothes I wore onto the plane. The girls were sitting on the couch in matching blue and purple shorts sets. “Oh good, you’re awake. We might have a solution to your clothing problem.” I sat down on the chair at the table, “what’s your solution?” “Well, we were talking after you went to bed last night, and we each have 3 extra outfits and swimsuits, which would take us to exactly next week when we leave. I know it’s crazy, but we can make you look like a girl, you have the hair for it and we have the makeup skills to do it.”

“That’s the craziest thing I’ve ever heard. There’s absolutely no way that works.” The girls just stared at me, watching me process. After a few minutes, I looked up, “how is this going to work? I’m not in, but I want to hear your plan.”

“Why tell you when we can show you!” The girls stood up, grabbed my arm and whisked me into their room. On the bed was a blue bikini and a white two piece dress with a little tan purse. “So this will be for our beach day…” Charlotte pointed to the bikini, “…and this’ll be for our dinner and photoshoot!” Tori pointed to the dress and purse. “You can get shaved and we can do your hair, makeup, and nails. No one will have any idea you’re actually a guy.”

“Ok fine, we’ll give it a try for today. Hand me the razor.” Tori handed me a green razor and I reluctantly headed into the shower. “Don’t forget to use my shampoo, conditioner, and body wash. We don’t want you smelling like a boy.” I came out smelling like flowers and smoother than I’ve ever felt in my life. It almost felt good, but I’d never tell the girls that. I was wrapped in a towel as Charlotte came in to braid my hair and help apply a bit of makeup. I slid up the blue thong bikini bottoms, which hugged my hips and slipped right in between my cheeks. Tori tied the top as it hugged my chest.

“Ok “girls”, ready to go to the beach and get our tan on!” Charlotte excitedly said. I was nervous walking down to the beach, but no one really looked at all. We were just three girls making our way to the lounge chairs by the beach. When we got to the chairs we sat and talked for a bit, then I fell asleep for a few hours, occasionally rolling from front to back. “Oooo someone has some tan lines from her new bikini!” I blushed and looked in the mirror seeing two pale triangles on my chest.

“Oh I guess so haha” I replied. “Anyway I’m going to shower to get ready for dinner.” I couldn’t help with brush over my tan lines in the shower. They just looked so…girlish. I snapped out of it and showered so one of the girls could help me get ready for dinner. The white two piece dress laying on the bed, along with a pair of white cotton panties.

“You better get those on,” Charlotte was standing in the doorway to my room, “we don’t want to be late to our reservations.” I slipped on the outfit and Charlotte made sure my makeup and hair looked good. She also gave me some fake nails to put on. I put my phone on the purse and we went on our way.

At the restaurant, I had to make sure I used a higher pitched voice when ordering to not give myself away. I successfully made it through dinner and we were sipping on cocktails walking the beach. “Let’s get photos for insta! You too Chrissy!” Tori winked at me as her and Charlotte backed up, leaving me alone on the beach with the sunset in the background. “Smile girl, give us a cute pose!” The girls snapped photos. “Chrissy, you look STUNNING! Look at you!”

I looked at the photos and all I saw was a gorgeous blonde bombshell. “That’s really me? Oh my god!” I was shocked how I looked.