Chapter 2

“Definitely catching.”

There was another moment of comfortable silence as we passed the joint back and forth.

“You said you wanted to help me and give me a birthday present. Would you still be willing to do something for me?”

“Well, if you fantasize about catching, I don’t think I’m physically equipped to be of much help to you,” I said, teasing him again.

He gave me a very serious look. I could tell that whatever was on his mind was important to him and I immediately felt bad about my earlier quip.

“Jesse, of course I’ll help you with whatever you want.”

“Would you help me dress as a woman?” he said in a voice barely above a whisper.

I quickly tried to get the shocked expression off my face. Jesse being gay was pretty easy to accept. Jesse wanting my help to dress in drag, that came out of left field. In the end, though, it didn’t matter; he was still my best friend.

“Of course I will,” I said, trying to focus and mentally formulate something that resembled a plan.

“What should I do first, then?” he asked.

I thought for a moment while studying him from head to toe. “You need to shave all the hair off your body from the neck down, and by the time you get back from the shower I will have figured out what to do next.”

He instantly jumped up and tore out of my dorm room. I could tell he was excited about this and I don’t think I had ever seen him move so fast. Well, maybe except a time or two when he was being chased by a couple of bullies in high school.

About a half hour later I heard a knock on the door. I opened it and Jesse walked back into my room, freshly showered and shaved and wearing shorts and a tank top. I had everything set up and ready to go for his transformation.

“Sit here,” I said as I pointed at the chair I had placed in the middle of the room.

Once he sat down, I immediately went to work. I could tell he had washed his face and shaved his very sparse facial hair. I put on a light coat of moisturizer while admiring his beautiful skin; it was something I’d never really noticed before. After the moisturizer, it was time for the concealer, and luckily I had foundation that I thought would match his skin tone perfectly.

I used my brush to apply a very light coat of setting powder. If we’re going to do this, we might as well do it right, I thought. The next step was highlighter. I brushed it around the corners of his eyes, beneath his eyelids, and finished on his high cheekbones, which gave his face a nice depth of color. I continued to work on his eyes using a powder that was a couple of shades darker than his natural skin tone. I dug around in my makeup case for a few seconds until I found the blush. Meticulously, I applied a small amount on his cheeks to help accentuate his high cheekbones.