The Study

Chapter 23: Wingman

The next morning, I woke up to Jessica's smile as she said, "Ever since the day of the sleepover, when we kissed for the first time, I've always felt a connection with you."

I felt my heart race as I stared back at her. I had never thought of her in that way before, but now that she had mentioned it, I couldn't help but feel the same way.

After we had a shower and got dressed, we went down for breakfast. Marie greeted us with a smile and asked, "Good morning, girls. Did you have fun last night?"

"Oh, last night was really fun," Jessica replied, grinning at me. We both giggled as we stared at each other.

After breakfast, Jessica had to leave. "Bye, Heather. Thanks for last night," she said.

"Oh, you too," I replied, shutting the door behind her.

As I walked back to my room, I couldn't help but contemplate what had happened between us. I knew that I wanted to put it behind us and go on to be friends, but at the same time, I couldn't shake the feeling of curiosity.

Just as I was lost in thought, fantasising about what could have been, I heard a knock on my door.

"Hey, Heather, it's Darryl," he said, opening the door.

"Yeah, come in," I replied.

He walked in and said, "Hey, Bryan, you've been a girl for a while now, right? So, I kinda need your help."

"Sure, what's up?" I asked, curious.

"So, there's this girl, Kira, who works at a café that I go to often, and I've been trying to get her attention, but I don't think I'm making much progress," he explained. "Could you be my wingman and help me out?"

"Of course, I can help you out," I replied, happy to help. As Darryl and I walked towards the café, he told me more about Kira and what he liked about her. "She's smart, funny, and always has a smile on her face," he said.

When we arrived at the café, Darryl greeted Kira and ordered his usual coffee. I could tell that he was nervous, so I tried to put him at ease by making small talk with Kira while he waited for his drink.

As we chatted, I could see why Darryl was attracted to her. Kira was friendly, charming, and had a great sense of humour. I also noticed that she seemed to be interested in Darryl, but was maybe a bit shy.

I could see that Darryl was still too nervous to make a move, so I decided to give him a little push. "You know, Kira, Darryl has a thing for you too," I said, winking at her.

Kira's eyes widened, "No way! Are you serious?"

I nodded and handed her a pen and a napkin, "Yep, I am. Why don't you give him your number, and maybe you guys can go out sometime?"

Kira blushed as she quickly scribbled down her number, "Sure, here you go. Tell him to give me a call."

As we left the café, Darryl was practically jumping with excitement. "Bryan, you're a genius! I can't believe it worked!"

I grinned, "Hey, I just gave you a little push. You did the rest."

"I owe you big time, man," Darryl said, giving me a grateful hug.

As Christmas eve approached, my mother informed us that we would be spending the holidays at my grandparents' place. The thought of going there as Heather made me nervous, as they had only been told about my transition but never actually seen me as a girl before.

The journey to their house took a few hours, and I spent most of the time lost in thought, wondering how they would react to seeing me as Heather. As we finally reached their house, Mee Maw and Pop Pop were outside waiting for us to arrive.

Darryl got out of the car first and opened the trunk to grab our bags, while Mum and Dad went to greet my grandparents. "Oh, and where is our little angel?" Mee Maw joked. I took a deep breath and stepped out of the car, hoping for the best.

"Oh, Bryan, there you are!" Mee Maw said, looking at me in disbelief. "Is that really you?" she added, still trying to wrap her head around the fact that her grandson was now her granddaughter.

Pop Pop hugged me and said, "You make a pretty woman." I smiled.

They invited us inside, and the smell of the dinner wafting through the house was amazing. We said our prayers and started dinner, as we sat at the dinner table, my grandparents couldn't help but make a few lighthearted jokes. "I never thought I'd see my grandson in a dress," Pop Pop chuckled, causing everyone to burst into laughter.

Mee Maw joined in, "Well, it looks like you make a prettier girl than any of us ever could!" I blushed, feeling a bit embarrassed

After dinner, Mee Maw showed Darryl and me to the room where we would be staying. "I hope you like it, sweetie," she said to me, giving me a warm smile.