Brothers and Sisters: Part 1

Brothers and Sisters: Part 1
by RogerGirl

  Hey, how's it going?  My name is Gabriel Collins, although I go by Gabe for short, and I'm about to tell you the story of how I entered a competition for new drag performers.  In case you're wondering, I'm straight and married with two young kids.  Before that night I'd never dressed in drag before, but I decided to do it for my little brother Jay.  Well, I should probably say younger brother since he's bigger than I am now.  Jay is five years younger than me, but we've always been very close.  Growing up we would play sports together and I would help him meet girls.  When he turned sixteen, he confided in me that he was gay.  I told him I would keep it a secret until he was ready to come out, and remained by his side when he finally felt ready to tell our parents and the rest of his friends and family.  Our parents were angry and confused at first, so I let him stay with me at my apartment for a while.  Eventually our parents came to accept his being gay and they have even gotten to know his current boyfriend pretty well.

  Now, I suppose you are wondering how I came to enter the competition.  When Jay turned twenty, he came to me one day at my house while my wife was out and told me that he had been practicing makeup and dressing in drag for a while and wanted to enter a competition at a club nearby.  While everyone back home knew he was gay, he hadn't told anyone at his college and didn't have any gay friends.  It would also be a couple years before he'd find his first boyfriend.  

"Good luck," I said to him after he told me, "I'm sure you'll do well."

"Actually," he said, "I'm kind of nervous about this.  I've only dressed in drag at home.  What if someone I know recognizes me?"

"Don't worry," I told him, "If they're at the club, they're probably just there to perform or see the show."

"Um," he said nervously, "I feel kind of strange asking you this, but could you come with me?"

"Sure," I replied, "I'd be happy to watch you."

"Oh," he continued, "I meant could you enter with me?  You won't be the only straight guy there.  A few of the other performers are straight."

"I don't know" I said, "I'd like to come with you for support, but I've never dressed up before.  I'd be awkward walking around in heels."

"Don't worry," he responded, "we have some time before the competition.  I will help you get ready."

"Get ready for what?" my wife Debbie said as she came in the door with a bag of groceries.

"Hi Debbie," Jay said, "I want to enter a drag competition on Halloween, but I'm kind of nervous about it.  I was asking Gabe if he'd enter with me for support."

"I told him I'd do it," I said, "but that I'd never dressed up before."

"Oh, that's sweet," Debbie said as she kissed me, "You're a really good brother.  Don't worry, I'll also help you get ready.  It might be kind of fun dressing you up as a girl."

"Yes," Jay said, "With you're build and softer features, I'm a little jealous that you'll look prettier than me.  What kind of look do you want for the competition?"

"What do you mean?" I asked.

"Well," he replied, "I typically go for a more over the top look, but with your features I think you might look better with a natural girl style."

"I'll let you decide," I said.

  With that, my wife and brother began making plans for my drag debut.  I wondered to myself what I was getting into, but I knew this was important to Jay so I decided to try to have fun with it.