Julie and I had become closer than we had ever dreamed, but we were still siblings and were prone to poke fun at each other and take advantage of certain situations. She and I had made a bet a few months back and I lost. As a result I had to do something I didn’t expect I would have to do ever.
“Look Drew has been begging me talk you into letting him take you to prom,” Julie said, “Besides, you lost the bet so you have to go with him.”
“Look it is one thing when we are alone in private, but now we are talking about going out in public where I will be seen by a bunch of people.” I said.
“It’s not like you haven’t been out before and you and Drew aren’t exactly strangers.” Julie replied.
“That’s not the point, Julie.” I said.
“Look I will help you.” she replied, “Remember you did agree to the bet.”
“I know…” I replied, “Okay but you are going to help me and I am not going to stay long. An hour at best.”
“Fair enough.” she said.
So we started by looking at Julie’s prom dress she wore the year before for her prom. The teal blue color really didn’t fit me and neither did the top portion of the dress. Julie was a little more developed in the chest than I was. So we decided to do a little shopping, but I couldn’t go trying on dresses as Brendan, so I decided to dress as Brenda and we went to a dress shop at the outlet mall just outside of town. Going in the middle of the week turned out to be the best thing since the place was empty and we had it all to ourselves.
We walked in and were immediately met by the only sales person there. Another plus.
“We need to find a prom dress for my sister.” Julie said.
“Sure, we can do that,” the sales lady said, “She looks like a size 6, so let me get a few for you to try on and get a dressing room started for you.”
I looked at Julie and asked, “How the hell did she know my size?”
“It’s her job to know.” Julie replied.
We walked towards the back of the small shop and waited for the lady to return. She came back with about 5 or 6 dresses hanging on a rolling rack. She started to pull them one by one and immediately eliminated 3 of them.
“Yeah I don’t think this color is you. So we will stay away from the cream and yellow colors.” she said.
She pulled a gorgeous red dress that I fell in love with.
“So are you ready?” she asked.
“Lead the way.” I said.
She walked me to the dressing room and closed the door behind her while I got undressed. I slid on the red dress and after adjusting the fake boobs, I started to move around to see if it fit comfortably.
“Hey, what’s taking so long in there.” Julie said.
“I am trying it on, wait a minute.” I said.
“Well get out here so I can see it.” she said.
I got it on and walked out to the mirrors where Julie was waiting.
“Wow that looks great, but I don’t think the color is right.” Julie said.
“What are you talking about?” I said, “The color looks great.”
“I think maybe a little darker… maybe deep lavender.” the sales lady added.
“Lavender?” I asked.
“Purple stupid.” Julie said.
“I know what lavender is you bitch.” I replied.
While we continue to playfully banter back and forth, the sales lady came back with a similar dress in PURPLE. I went back to the dressing room and changed and this one was even better. The only issue was it was strapless and my chest was not going to be able to hold it up. So we tried one more dress, an antique rose colored dress that was short in the skirt and had a very simple top with a bow in the back. It was very slimming and putting it on was very easy. I stepped out and when Julie saw me in it she was amazed.
“Wow, that’s the one.” Julie said.
“You think so?” I asked.
“Oh yeah, Drew is going to love it.” she said.
The nice thing was we didn’t have to alter it much so we put the dress on order and also ordered the shoes so they could be dyed to match the dress.
“Did you want to look at any lingerie while you are here?” the sales lady said, “We have a special today, that if you order a dress and shoes, the lingerie is 50% off.”
Well Julie and I looked at each other and we just couldn’t pass that up. So we went back search for the rest of the outfit – bra, panties and tights. After we were done at the dress shop we stopped at a couple more shops to pick out some cheap costume jewelry and some makeup.
We made the long drive home and Julie, couldn’t help but ask me the question she continued to ask me since she found out about me.
“Do you think you will ever tell Mom?” she asked.
“I don’t know, I mean… you said she already knew.” I said.
“Yeah, but I think you should eventually tell her.” she said.
“I know, I just don’t know when the right time is to tell her.” I replied, “Me telling her doesn’t really change anything, but I just feel bad.”
“Why?” she asked.
“I don’t know, I don’t want her to think it’s her fault that I turned out this way.” I replied.
“Is it?” she asked.
“Of course not.” I said.
“Maybe it is a little bit.” she explained, “Think about it. You are the only male in the family and you grew up around just the two of us. It had to rub off a little.”
“Maybe, but I don’t think you made me gay or bi or whatever the hell I am.” I replied.
The conversation quickly died down and we continued home. A few weeks later it was prom week. I wasn’t as much excited, as I was scared out of my mind. Julie didn’t help by reminding me constantly as the day approached. Drew was really excited about his date. He kept telling me how he was looking forward to showing me off to a few of his friends. I tried to explain to him I wasn’t happy about any of this, and he knew this was part of a bet I lost to Julie, but he didn’t really care. He apparently had been talking about his “girlfriend” to his buddies and wanted them to see her just once.
Prom night was now here and Julie took the day off from work to make sure I looked my best. She started by giving me a manicure and home facial. Then after a long hot bath, I started getting ready. I started with the new bra and panty set. Beautiful black lace that covered all the right areas and was snug around my waist, followed by the tan pantyhose, but I was far from ready, I slipped on a silk robe that belonged to Julie and sat in her room while she fixed my hair and makeup. Making sure I was transformed properly. After a couple of hours, it was now time for the important parts. I put on the dress and slipped on the shoes, both of which fit perfectly. I then got up and stood in front of the full length mirror admiring the look.
What I didn’t realize was that Mom was standing there too watching me. I turned and almost pee’d myself. She just stood there for a moment with a smile on her face.
“You look beautiful.” she said.
“I figured you wouldn’t let me show you off to her, so I just asked her to watch.” Julie said.
“I’m sorry Mom.” I said.
“For what?” she said as she walked to me, “I just want you to be happy.”
She adjusted my dress and bra straps and then gave me a gentle hug.
“I want to explain.” I said.
“Explain later.” she said, “Tonight I just want you to enjoy yourself. We can talk afterward.”
She then walked out and I sat back down with a huge relief. Now that one brick was off my shoulders, it was now just the bricks of the evening. So I waited for Drew who was running late. Strange how it is usually the woman who is running late. I then heard the doorbell and stood up. Julie ran into the room and shut the door.
“What are you doing?” I asked.
“You have to make him wait.” she said, “You need to make an entrance.”
So she did a quick touch up of my makeup and hit me with some of her best perfume while Mom talked with Drew.
“Okay, are you ready?” Julie asked.
With a deep breath, I said, “Ready as I’ll ever be.”
She opened the door and I walked out to meet Drew. Julie walked behind me and we both watched Drew’s mouth fall open.
“You look beautiful.” he said.
“You look great too.” I said.
I looked over at Mom who was already crying and Julie grabbed the camera so she could have pictures of the two of us before we left. Julie kept snapping pictures while Drew pinned the corsage on me and stood next to me with his hand on my lower back – slowly moving it downward. I walked out to find Drew rented a limo for the evening. After hugging Mom and Julie we got in the car and left for the hall. The entire ride was quiet right up until we arrived.
“Remember, I don’t really want to stay too long.” I said, “I know you really want this and part of me does too, but if I start to feel uncomfortable, I hope you understand if I walk out.”
“Listen, I don’t like these anymore than you do.” he said, “Let’s go in take our picture and meet up with my buddies then we can go, is that okay?”
“I’m sorry about all this.” I said, “I wish I wasn’t so paranoid.”
“It’s okay. I am just glad I get to go to prom with the most beautiful woman I have ever seen.” he said as he look deep into my eyes.
We stepped out of the limo and stood in line to go in. While in line, we ran into one of his buddies and it was a very quick introduction. The rest would come inside. After checking in, we made it to the photographer who took our official prom picture. We then went into the hall and found the table with all of his buddies.
“He guys,” Drew said.
The group of about 5 boys all said together, “DDDRRREEEWWWW.”
“Guys, this is Brenda.” Drew said.
I gave them all a very shy wave, but really didn’t say anything. I started to feel uncomfortable as I looked at their dates who were looking at me almost angrily. Drew showed me to my seat right next to the girls and he spent the next few minutes talking with “his boys” while I sat there quietly.
“So you graduated early?” one of the girls said.
“Yeah, in December.” I replied softly.
“That’s cool. You must be really smart.” one of the other girls said.
“Well maybe not that smart, look at her date.” a third girl said jokingly.
I just smiled and looked over at Drew who never ventured too far and kept his eyes on me in case I wanted to go. About an hour later, the band began playing a slow ballad and everyone got up to dance. Drew walked over to me and sat down.
“Don’t worry.” he said.
“Come on,” I said, “It is your prom, you can’t just sit here.”
I took him by the hand and we walked to the dance floor where we danced to the next two songs. Afterwards we returned to the table and the girls were heading to the bathroom and decided to take me with them. We walked in and the girls continued to gab as the hairspray continued to fly and everyone was checking their makeup. When we returned, I looked at Drew and it was time to go. As we said goodbye, a few of the girls gave me their phone number as did a couple of Drew’s friends. We then headed out. Once outside, Drew signaled for the limo and I stood outside with Drew enjoying the night air.
We got in the car and planned to go to dinner at a little restaurant not far from the house. After dinner we decided to drive around for a little while and enjoy the rest of the evening. I could tell Drew was tired and I was equally exhausted, but I was able to pull it off. No one recognized me – even at the restaurant where I had been several times before as Brendan.
As we drove around, Drew laid his head in my lap and I simply stared out the window as I rubbed his hair. I could tell he was getting turned on as his pants began to tent. I was also getting pretty excited, since I hadn’t had sex since the first time he and I met. I asked him to sit up and I found the button that closed the partition so the driver could not see us. I then began to rub my hands down Drew’s chest and onto his rock hard cock.
“What are you doing?” he asked as I started to unzip his pants.
“Do you want me to stop?” I asked as I reached up and kissed him.
Drew never said another word, he just left everything to me. After unzipping his pants and detaching his cumber bun, I exposed his thick cock which I was no longer afraid of. I dove right in and began to wet it as I stroked him vigorously. As I went down on him I could feel his hand slide up my back and onto my head gently pushing me back down on him.
I continued to suck his cock until I could feel him shake.
He whispered excitedly, “Oh yeah, I’m gonna cum.”
“It’s okay baby, I want it all.” I said.
I immediately went back down and began to stroke him faster and faster moving my head up and down with my tongue pressed firmly against his cock, until he exploded in my mouth. Another first for me, but I didn’t want him ruining my dress and I wanted to experience what that was like. The thrill was fantastic as he spewed so hard, his cum shot to the back of my throat. I kept my oral grip on him until he stopped shaking and I then swallowed all he gave me and slowly and gently sucked him until he was empty an nice and clean. When we were done, I sat up and he zipped up quickly as I took out my compact and fixed my makeup and lipstick. He then dropped back into my lap and fell right to sleep… just like a typical man.