Charlie works as a waiter at the retro-style diner at the corner of Green Street and Winter Road. He never thought much of it.
Charlie was a daring 16-year-old boy, too. He took on any dare his friends threw at him when losing a bet-which happened...
Oops! This image does not follow our content guidelines. To continue publishing, please remove it or upload a different image.
All night Taylor, Lily, and I went over how to act femininely when eating, how the to speak femininely, and anything on how to convince my date I was a girl and not really a boy. Then later, Lily let me try on some heels and a cute, white miniskirt so I could learn how to walk in heels without exposing myself, since I didn't know how to do that at the diner.
When we finally settled down and began to fall asleep, we gossiped about Daniel, and they kept bombarding me with questions about if I really liked hm, and if I was gay, and I had to keep telling them I really didn't know, I had only seen him once.
After hours, we finally fell asleep, around half past midnight.
***
I was woken up by Taylor the next morning, her shaking me and Lily standing at her closet with her finger to her chin, deciding what she thought I should wear. I sat up, my stomach filled with excitement. Today was my date with Daniel! Taylor helped me up and began rambling away about how she and Lily had trouble deciding what to have me wear, since they didn't know what Daniel was like. They asked me what I wanted to wear.
"Umm..." I blushed a bit, knowing that anything I picked would be embarrassing, since I'm a boy, not a girl! Yet still, I had this feeling that I couldn't describe, excitement at the thought of wearing female clothes again, and going out with possibly the hottest boy in town. I brushed my hands along the clothes, a tingling feeling running through my body. Finally, I stopped, the bright color of one dress catching my eye. I pulled it out, the dress slipping off the hanger.
It was a bright, blueish-teal color, and it had a scrunched-up textured top with strings tied in bows for straps. The skirt part was ruffle at the waist, hem, and in the middle of the skirt. I smiled as I felt the soft material of the skirt, sending a warm feeling through me.
"I think... this one." I mumbled, not meeting Taylor's and Lily's eyes.
"Okay!" Taylor chirped, and I turned around, holding the bright fabric, while I watched Lily go to her dresser. She dug through some drawers, and came back, taking the dress from my arms. She handed me two more clothing articles: a white, lacy bra with thin straps, and an equally as lacy, hot pink pair of panties. I took them delicately, and again avoided the girls' eyes as they instructed me to go put them on in the bathroom.
I slipped the underwear up and it fit snugly around my waist, a very satisfying feeling. I struggled, but eventually figured out how to put on the bra, slipping the straps over my shoulders with a sly smile. I then wrapped a towel around my waist for coverage before I stepped outside, noticing once again how thin and lithe I was, my body shape resembling so much like a girl's now that I thought about it. That might be another reason why I could pull off being a girl so convincingly to Daniel and his family.
Taylor slipped the teal dress onto me, and I pulled the ribbon-like straps up over my shoulders. The skirt fell over my towel, and Taylor started zipping up the back of the dress, and I dropped the towel to the floor once the whole dress was firmly secured on my body. I looked in the full length mirror, smiling, but still feeling unsatisfied. I twirled once, seeing the skirt fly beautifully, but as I looked at myself, all I saw was a boy foolishly messing around and wearing a dress. It was a bit embarrassing, and I thought over my decision to go through with this again, but then I turned to see Taylor's and Lily's excited faces, and thought of Daniel's piercing hazel eyes, and I smiled and knew this was something I wanted.
***
After what seemed like a half-hour of preparation, I stood in the mirror with Taylor and Lily once again, finally ready to go. We had paired my dress of choice with some strappy, silver, stiletto, two-and-a-half-inch heels that brought my height to a whopping five foot seven. I wasn't too worried about my height because I was pretty short and Daniel was hella tall. My makeup was a naturally-dewy look, with bright highlight on my nose and the inner corner of my eyes, but long eyelashes. We decided to pull my short, blonde hair into a messy low bun, with some pieces in the front pulled out and dangling in an elegant manner. Finally, the long strap of a white, leather purse from hung from my left shoulder and fell at my left side, with my phone, wallet, and keys in it.
"Wow..." I was speechless looking at my girl self, once again.
"Damn. You look better than me. Daniel would totally want to fuck you, hottie." Lily joked. My face turned bright red as I tugged at my skirt, suddenly uncomfortable.
"Shut up, dumbass!" Taylor playfully punched her in the shoulder and walked up beside me, gently resting a hand on my shoulder. "Hey," She softly whispered, and handed me something. It was a gold chain with a circular pendant—Taylor's iconic compass necklace she constantly wore. "Just want you to have this for your date to know I'm always there for you and supporting you." I looked to her, and our eyes were at the same level, and she smiled warmly as she helped me put on the necklace.
"Thanks, Tay." I whispered and hugged her tightly. "You're the best friend I could ask for." I could feel her smile into my shoulder before she pulled away.
"Alright. Now go get your man!" She squealed and we all laughed.
*** "Okay, so what are you gonna say when you meet him?" Lily quizzed.
"I'll tell him he looks nice and that it's a great spot for a date." I replied quickly. I sat in the passenger's seat of her jeep, and they were giving me a pep talk where we were parked right outside of our picnic spot where Daniel promised to meet me.
"Okay, and what's your move on him gonna be?" Taylor then asked.
"Brush up against him and hold hands, and if he wants to kiss me to go with the flow." I said, freezing. Kiss me. I just said I wanted another boy to kiss me. Holy shit, I am gay.
Taylor must have noticed my nervousness, because she softened her gaze and rubbed her thumb over the back of my hand. "It'll be okay. You look stunning, he already thinks you're adorable, he's going to love you. And you're going to have an awesome time." She reassured me. I smiled, then opened the door, standing up. In my best feminine voice and posture, I said.
"Thank you guys, so much, for the ride! You're the best." With a thankful glance at both of them. As I shut the door, we waved bye to each other as Lily drove away. Then I took a big breath, and turned to look at the gazebo where we are supposed to meet.
