My sister, Rebecca, was always a pain. She's in her mid-twenties, older than me by several years. Because of our age difference, she considered that a license to boss me around. With her, it was a love-hate relationship. Rebecca is my only immediate family member. But she acted like I should be subservient to her wishes. Her attitude got tiring. Unfortunately, I couldn't afford to live on my own. So, I was stuck with her.
To complicate matters, I am a cross-dresser. I don't know why I started, but I enjoy it. When I dress that way, I fantasize about what it would be like to be a woman. Sucking a cock and having a man fuck me when I look like that was one of my dreams. It is a pleasant distraction from my everyday life. I never shared this secret with my sister. There would be no telling how she would react. But I was about to find out. Because of this, I now show my sister the respect and deference she demands and deserves.
Our parents died in an auto accident. We share the house we inherited from them. Rebecca was old enough, so she accepted responsibility for me. She works a lot and isn't home much. There's also a club for women that she attends on Thursday evenings. So, when I am alone, I often use the chance to dress up.
One day, she told me she would be away for the weekend. It didn't show, but I was ecstatic. I could spend time dressing as a female.
“I should be back on Sunday evening,” she said. “The chores better be finished before I get back. Don't be so lazy.”
“Yeah, whatever. I’ll see what I can do.”
“You'd better do them! Remember, I'm in charge of you. Find a place of your own if you don't like it.”
Then she paused. “It's too bad you weren't born a girl. You would be so much better off. I wouldn't have to put up with as much as I do with you.”
“Well, I'm not a girl,” I retorted. She walked away, muttering.
Rebecca brought her suitcases to her car, then drove off. Although I was anxious to start my transformation, I chose to wait a little longer. She may have overlooked something and would need to return. I had a couple of days to enjoy my feminine side before she came home. There was no hurry.
Nature blessed me with a similar build to my sister. A closet full of her clothes was mine to explore. Also, I had a couple of outfits hidden away. They were on my list to wear at some point during the weekend. Glamour was my agenda.
After an hour, I felt it was safe to get dolled up. That night and all the next day, I indulged myself. I loved these occasions, as they didn't happen that often. Sunday arrived, but Rebecca wasn't due until the evening. Since it was the last day of vacation from my sister, I decided to go all out.
From Rebecca's closet, I chose a sexy sequined strapless party dress. I took extra care with my makeup. A pretty necklace, earrings, and a bracelet added to my look. Bright red gloss covered my lips. A wig and a pair of heels completed things.
I'd often admired myself in a mirror when dressed like this. This time, I felt like I had done an excellent job on myself. It was hard to tell I was a guy. But my fantasies were in my head, expected to remain that way. Instead, I could only masturbate to videos on the internet.
My morning was spent with this dream. I kept an eye on the clock, but there was plenty of time before I had to change back.
I was lost in my fantasies when the door to my bedroom suddenly opened. Rebecca was back much sooner than she said she would.
“Why didn't you do anything?” Then she stopped. “What the...?” she said. “You little shit. I came back from my weekend to find nothing's been done. Not only that, but it seems my brother wants to be my sister. You're wearing my fucking dress!”
I could tell she was pretty pissed. She rarely swore. Now those words were coming out of her mouth right and left.
“Stand up, asshole.”
Meekly, I obeyed.
“Wow, you do look like a girl. You didn't do anything around the house. But at least you finally did something right, even if it was to turn yourself into Barbie.”
By now, I was flushed from embarrassment. There was no other explanation for why I looked that way. She caught me.
“Oh, poor thing. You're turning red.” She laughed. “It matches the blush on your cheeks.”
“I'll take this off, Rebecca,” I said.
“Oh, no, leave your makeup on. But put on a different dress. I don't want you to ruin that one. For now, you can take a more casual one from my closet. You probably know what fits. Then come back here. I need a moment to think.”
As she said to do, I found another dress to wear. I returned and presented myself to her. By now, she had cooled down some.
“Well, little brother, I said you should have been born a girl. It appears you took my comments to heart. This isn't your first time playing dress-up, from the looks of it. So, here's how things will be from now on. Since you want to be a girl, you'll get your wish. When you're home, I want you in female clothes. That means dresses, makeup, and heels. All your chores around the house will be done this way. Wear women's shorts, sneakers, and a feminine top for yard work. Only wear guys' clothes when you go to work. When I come home in the evening, dinner should be ready. Again, I want you to look immaculately feminine.”
“Also, you will address me as 'ma'am' or 'Miss Rebecca.' Not 'Rebecca,' 'Becky,' or 'Sis.' Only 'ma'am' or 'Miss Rebecca' will be acceptable. If you disobey me, you'll be out on the street. Remember, we have webcams to keep an eye on the house when no one is home. I'll be checking on you with them.”
“Now, get out of that stuff. Then grab your wallet and credit card. We are going clothes shopping. Your wardrobe should reflect your new situation. I expect you to regularly add things to it, too. Pink will become a predominant color in your closet.”
A little while later, I returned, looking more like my biological self.
“You better have panties on,” she said.
I pulled down my jeans a little to show her.
“Oh, pink panties and pantyhose, too! That's good. You're learning already. I should have feminized you a long time ago. Instead, you did the job for me. It looks like your new role will suit you well. You'll fit right in.”
“Fit into what?” I asked.
“ ‘Fit into what, ma'am.’ I will recommend you as a regular guest at my Thursday club.”
“I know you go to some meetings on those nights. But you never said what that club was.”
“Because it wasn't your business to know. And let me remind you again to address me as ‘ma'am.’ All I'll say for now is that it's a women's organization. But we often have males as guests. Once I show the girls pictures of you, I'm sure they'll agree to have you join us. When we return from our errands, I want you all dressed up again. You'll model all your new stuff for me. Then I'll share the pictures with the others. Once they see them, I expect the vote to include you in our meetings will be unanimous.”
“Oh, come on, um, ma'am. Can't we leave this between the two of us? I'm already doing what you asked.”
“If you did what I asked, we wouldn't have this conversation. Maybe I never would have discovered your escapades while I was gone. Remember what I said? If you don't like it, then leave. While you live here, you will abide by my rules. Oh, and if you do leave, I will not allow you to take any male clothing with you. It will all be tossed or given to the Goodwill. You can face the world on your own as a dainty princess. Now, let’s get going.”
For the rest of the afternoon, we shopped for everything I'd need to begin my new life as a girl. I was measured for a bra. My sister felt I should wear at least a C cup. The fitter gave her some recommendations. Rebecca agreed and added them to my shopping basket.
“I've helped many men find the right bra,” said the fitter. “It's not my place to judge. My job is to ensure the customer is pleased with their purchases, no matter who they are.” Then she turned to me. “I hope you enjoy what the lady chose for you, sir.”
Along with the bras, Rebecca had me buy several pairs of pantyhose. The cashier looked at me strangely as I paid for everything but said nothing. This amused my sister.
“When you buy yourself any female clothing, don't do it online. Do it in person. I'll want to see the receipts as proof.”
The dress department was our next stop. Rebecca held up a few different ones on me. “These will look good on you,” she said. I also bought some casual clothes for when I couldn't wear a dress. A visit to another store found me purchasing more dresses.
Our final stop was for makeup. Then I had everything I needed to become the girl my sister wanted.
After we returned, I donned my new clothes. Rebecca took many pictures of me. She e-mailed them to the other women in her mysterious club. Over the next few hours, she received enthusiastic responses from the other members.
She turned to me and said, “It's definite. You'll join us Thursday night. Make sure you look your best. I want you to make a good impression on the ladies and our guests.”
I was still puzzled about her plans for me, but I supposed I would find out on Thursday.
Monday morning began my daily routine of dressing up to do things around the house. I felt relieved that I no longer had to hide it from Rebecca. But although I enjoyed looking like that, I didn't have time to surf the web for cross-dresser porn. There was a list from my sister that I needed to complete every day. Of course, I also had to spend time at my job. Putting on guys' clothes again before work was disappointing. But it was a necessary evil. After all, there were bills to pay for my new look.
Thursday found me up early so I could finish my chores sooner. Then I spent my time that afternoon becoming as pretty as I could. Rebecca was taking me to meet her girlfriends, so I had to look acceptable.
I chose a pink off-the-shoulder lace dress with matching heels. It seemed to me that it would make a good impression. When I showed the look to Rebecca, she nodded in approval. But she told me to wear a garter belt and stockings instead of pantyhose. “It will be better,” she said without explaining why. “Oh, and you'll need some perfume, too. Take care of that before we leave.”
I obeyed without question. Then we left the house and drove to her meeting. When we arrived, the person hosting the meeting greeted us. Several women were sitting in the living room.
Rebecca introduced me to them. “Girls, this is my brother. He wants to be like us.”
They laughed. “You'll never be a true female,” one woman said. “It's admirable of you to try because you're very pretty. But tonight, you will learn of ways you can serve us.”
She directed me to a room. In it were other cross-dressers. They all looked passable.
One said, “Oh, you must be the new girl. Have they given you a female name yet?”
“Um, no.”
“You'll receive one soon enough. I am named ‘Shirley.’ It's not one I would choose, but it's unwise to question them. How did you end up here?”
“My sister caught me in one of her dresses. She has been feminizing me since then.”
“Similar things have happened to us.”
“But what's going to happen tonight?” I asked. They looked at each other.
“I'm sorry, but we aren't allowed to tell you. You will find out, though.”
Another person chimed in. “Don't worry, you'll come to look forward to these nights. We all do.”
The others voiced their agreement.
Shortly after that, the door to the room opened. A woman stood there. She pointed at me. “Okay, you're the new one here. You'll go first. We have decided your female name will be ‘Danielle.’ Your sister agrees that it is perfect for a sissy like you. Come along, Danielle. It's time for your introduction to womanhood, or at least as close as you'll get to it.”
