The Waitress

{The Dare}

Charlie's POV
"Hey!" I yelped in pain as Johnathan slammed my fist down on the table with a loud thump, beating me in the arm wrestle. Ugh, why was I so weak?

"I win!" He laughed in triumph, and I laughed along. I knew he was going to dare me to do something next, like all my friends do when I lose a bet. They crowded around, curious to see what crazy dare I would tackle next.

My name is Charlie, and I'm a sixteen year old boy. I live in the  small town of Mintville, North Carolina, and have been working as a waiter at a retro-style diner called "Cherry on Top Diner" for a few months now. Our specialty is milkshakes, hence the "cherry on top." I am going into my junior year at South Mintville High. My best friends, Jonathan, Lily, and Taylor are all in my grade at my school. We've been friends since the sixth grade.

My group of friends and I loved to mess around and bet. Just like any other best friends. But I was the worst person out of the four of us to bet with, I always lose. But I like it that way. I always took on the worst dares nobody else would. It was pretty fun. I showed them how much tougher I was than them. Especially now, during summer break, while we had more time to do dares and other things without hours of school and homework.

Now, all my friends grouped together and whispered with Jonathan as they decided which dare to throw at me now. I heard Jonathan chuckle quietly, ruffling his hair, while Lily and Taylor giggled a bit louder than him. I grinned slyly, knowing I could do whatever it was they were planning. I watched for a few moments in silence, kicking me feet up on the table of the sports bar we were at, and placing my hands behind my head in a relaxed stance. Finally, they all turned around. Jonathan grinned evilly, his deep brown eyes sparkling with playful malice.

"The committee has decided." Taylor joked in an English accent, tossing her medium-length, thick blonde hair behind her head with a swift flick of her head. I grinned with a small laugh, sitting up normally again. "Drumroll please," She insisted. Lily and Jonathan joined her in banging their hands on the black, polished, wooden table, before Taylor cut them off.

"Charlie, your dare is to become a girl for a full twenty-four hours." Jonathan stated.

"You guys can hang out at my place today and I can show you the stuff I have!" Lily exclaimed.

"Oh my god yes!" Taylor squealed. "Lil has waaaayyy more makeup than me, together we can transform you to look exactly like a girl."

"Pleeeease, Charlie? Nobody will even know you're a boy!" Lily pleaded, and the two girls squeezed their hands together. I laughed.

"You guys think this is hard? I told you, any dare. I accept the challenge." I said smugly. Lily and Taylor got up and squealed quietly, they were obviously very excited. Jonathan and I laughed at them.

"Alright let's go! We can work out a plan and stuff for you." Lily said, and we left the sports bar after paying, and we all got into my car. I was the only one in the group that could drive already, so I was always taking us places.

My car was a nice, deep shimmery blue pickup truck. It wasn't too big, but perfect for me.
Lily climbed into the passenger's side as Jonathan and Taylor hopped into the back. Taylor squeezed Jonathan's hand excitedly, and gave him a peck on the cheek. Oh, did I mention the two of them
were dating? Yeah, they make a super cute couple. Lily and I dated for two months a while back, mostly because Taylor and Jonathan are dating. We decided it wasn't working out, and we were better off as best friends. But it's not awkward being around her at all.

Lily and Taylor talked to each other excitedly about what they were planning to do to make me look like a girl. I wasn't listening to a word they were saying though, I was too engrossed in my favorite song which was playing on the radio as I drove us to Lily's house.

I pulled into the driveway, and turned off the car. We all got out, and went inside.

Lily's parents were both doctors, so they could afford lots of stuff. They had a two story house, huge rooms, a pool and jacuzzi outback, and still had a huge backyard.

The four of us ran upstairs after Lily said hi to her parents and little brother, Tommy, quickly. We went into Lily's room, while the girls immediately ran for her bathroom. Jonathan and I followed. Lily opened up a small-ish cabinet above her sink to reveal rows of make-up. "Ta-da!" Taylor said in a sing-song voice.

Taylor was definitely right before. Lily does have a lot of makeup. I would for sure be unrecognizable except to people I were closest to. Nobody would even know I'm a boy.

For some reason, as I stared at all her makeup, I felt a jolt of excitement at the thought of wearing it and being a girl. I shook the thought away though, telling myself it was only the excitement of the dare, and proving to my friends I could do anything.

We went over the plan in detail for a while: The four of us would meet at Lily's tomorrow morning, then Jonathan, Taylor, and Lily got to pick out my outfit for the day. I had no say in whether or not I was comfortable wearing it. The girls would help me dress, then they would do my heavy makeup and disguise me as female. The girls chattered about jewelry they planned to force me to wear for a bit, and I chuckled.

Then, we'd spend the day going out in public and doing activities together, like bowling, going out to lunch, then take a walk around the park—we joked around and said I should start flirting with boys at the park, and I just laughed, thinking I probably would just do it to please them. Then we would come back to Lily's, while Jonathan went home, to get me and the girls ready for a nice, fancy dinner. Jonathan would get dressed up, too.

I felt excited and happy about the day to come. I didn't know why, but I felt like this would be my most fun dare yet.