Brothers and Sisters: Part 4

Brothers and Sisters: Part 4
by RogerGirl

  As I came downstairs, I noticed my brother sitting on the couch with Debbie.  Surprisingly, he was still dressed in his regular male clothes.  Since they were facing the TV, they did not see me until I entered the room.

"How do I look?" I asked in my female voice.

"Oh my god!" Debbie yelled excitedly, "You look so hot as a woman.  I'm a little jealous of how much better you look as a woman than I do."

"Well," I said as a I posed, "it took a lot of work to look like this and it isn't very comfortable.  If I'm going to dress as a woman though, I want to look as good as I can."

"You're going to be a hit at the club," Jay said, "I hope you win the competition."

"What do you mean?" I asked confusedly, "I'm just going for support.  You're the one that's going to win.  Do you want to go upstairs and change?"

"No," he replied nervously, "I don't think I'm going to enter.  I don't think I'm ready to go out in drag just yet."

"Come with me," I said as I walked to the den.

  Jay followed me and sat on the couch.  I sat down next to him and crossed my legs.  I had seen this fear in Jay before.  As kids and teenagers, I had to step in and build up his confidence before football games, basketball games, school plays, and even had to arrange some double dates so he wouldn't be alone.  While I was feeling nervous about going out dressed as a woman, I knew I had to step up again and build up his confidence.

"What's going on?" I asked in my regular male voice, "You were so excited to do this before."

"I just don't know if I'm ready to let people see me in drag," he answered, "When I dress up you can tell I'm really a guy underneath.  If someone I know sees me, they'll know it's me under the wig and makeup."

"Well," I said, "I'm dressed as a woman and I'm planning to go out and have fun tonight."

"Yeah," he said, "but you look like a real woman.  You don't look anything like Gabe dressed the way you are now.  If I didn't know it was you under there I would think you were just one of Debbie's friends."

"OK," I said, "you don't have to dress up, but you have to come with us to the club tonight and tell Reggie yourself that you've decided not to enter."

"OK," he said shyly.

  We got in the car and drove to the club.  There was a pretty big crowd, but Derrick recognized us and waved us in.  We walked over to the bar and I saw Regina mixing some drinks.  She wasn't performing that night, but she wanted to get into character before she hosted on Halloween.  She was wearing a miniskirt and halter top and a pair of knee high boots.  When she saw us she looked shocked.

"You look amazing," she said in a female voice, "Are you sure this is your first time?"

"Yes," I said in my female voice as I laughed, "I did spend some time practicing though."

"Well, you look good," she replied, "Why isn't your brother dressed?"

"He's having second thoughts about entering," I said.

"Well, Jay," she said as she turned to him, "if you still have doubts at the end of the night, then I will take your name off the list.  Until then, however, I want you to go have some fun and meet some of the people here."

"OK," he responded shyly.

  We made our way over a table where some of the other contestants were sitting.  Most of them were gay, but there was a straight guy sitting with his girlfriend who had only entered that day.  He told us his name was Shannon and that he had dressed as a woman before, but this would be his first time performing.  I spoke with several of the gay contestants and they were all touched by what I was willing to do for my brother.  

"I wish I had a brother like you," one guy who was sitting with his boyfriend said, "My brother hasn't spoken to me since I came out."

"Yeah," I responded, "I would never do that to Jay.  Do you guys think you could help me convince him not to drop out of the contest?"

"Of course," the guy's boyfriend who was dressed in drag replied, "We'll try, but ultimately it's up to Jay."

  There was a DJ and a dance floor where people were dancing before the show.  A few of us girls including Debbie, Shannon, and myself, took Jay by the hand and led him to the dance floor.  I have to admit I was pretty terrified at first since this was my first time out as a woman.  I knew I had to put my fear aside though to calm Jay down and show him it would be OK.  As the night went on, several others came and joined us.  Soon, I found myself dancing with Debbie and Jay was dancing with a man he had found in the crowd.  Jay and this man, whose name is Phil, would later start dating and now live together.  At one point, Debbie and I got separated and when I turned to kiss her, I ended up kissing Shannon instead.  We were both embarrassed, but Shannon made a pretty attractive woman and I have to admit was a pretty good kisser.  We laughed it off and continued dancing.  Soon the show started and most of the crowd moved to the performance area to see the performers.  After the show, many of the performers came out and talked with us and by the end of the night Jay was feeling more comfortable.

"Do you still want to drop out?" Regina asked as we were about to leave.

"No," Jay said more confidently as he glanced at Phil, who was standing next to him, "I think I'm going to do it."