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A Sister's Bet, Part One - Lessons free porn video
My sister, Jessica, and I have always been competitive. She’s twenty-one, a year older than me, but I’ve been told we bear a strong resemblance to each other.
I picked on her a lot, although she would get me back. Sometimes I would ask her, “What’s so special about being a girl? Jeez, I would think being female would be such a hassle. Wouldn’t it be easier if you had been born a guy?”
She retorted, “Why on earth would I want to be a guy? I love being female.”
I shook my head. “I don’t get it.”
“You probably never will, either. What an idiot, acting so macho, but I bet it’s all a front. You could never handle being a girl.”
“Why would I want to?”
“Maybe you’d finally see how the other half lives. But it doesn’t matter. You would never hack it.”
“If I became a girl somehow, all it would do is to show us both that I’ve been right all along. But that won’t happen.”
“Really? Would you like to bet on that?”
“Oh, right. What are you going to do, Jess, wave a magic wand?”
“If I had a magic wand, I would have used it on you long before now. But there’s a lot I can do. So, I’ll make you a bet. Live as a girl while Mom and Dad are away. My guess is you won’t handle it. You'll look for excuses to get out of it before a day or two has passed. So how about it, Mr. Macho? Are you macho enough to be a girl for two weeks, or is this all just an act?”
She knew how to push my buttons.
“Why would you make a bet that you know you’ll lose?”
“Because I’m right, so I won’t lose. You don’t understand what it’s like to be a girl. I think you should find out for yourself. So here’s my bet. After Mom and Dad leave for their vacation, dress as a girl while they’re gone. You may not wear any guys’ clothing at all. Instead, every day you will wear everything I would wear. That means panties, bras, dresses, and makeup, even pantyhose. Oh, and you’ll learn how to walk in heels, too. I’ll loan you some of my dresses. I think you’re probably close to my size. Before the end of two weeks, you will pass as a girl and do things a real girl would do.”
“This can just stay between us,” she continued. “I wouldn’t embarrass you in front of your friends.”
“What if I last two weeks?”
“In the unlikely event of that happening, I’ll do anything you ask, as long as it just stays between us.”
“And if I lose?”
“Then, I will get to make you into a girl any time I want for the rest of the summer. I told you I wouldn’t embarrass you or tell Mom and Dad. But you have to get dressed up when I say so. You’ll be my pretty sister.”
“What a stupid bet.”
“See? I knew you couldn't handle it! So much for the tough-guy act."
“Oh yeah? I’ll take your bet, then. I can think of lots of interesting things you could do for me when I last two weeks.”
“OK, Mom and Dad leave tomorrow. We’ll start you in on everything after they’re gone. Enjoy your last night of being a guy!”
The next day, Mom and Dad were up early to finish packing the car. They ate a quick breakfast and said their goodbyes.
“Take care of your brother while we’re gone. Make sure he stays out of trouble. We’ll see you in two weeks,” said Mom.
“Oh, don't worry, he’s in good hands,” Jessica said. I could imagine what was going through her head.
They drove off, and we went back inside.
“Let’s get started,” Jessica said. “I have a lot of work to do to transform you into a girl.”
I had a long two weeks ahead of me. What had I gotten myself into?
We went back inside.
She walked into the bathroom and turned on the water in the tub. Suds formed.
“Go get undressed, bro. We’re starting you off with a nice, girly bubble bath. Oh, and here’s a razor. Make sure you shave all the hair off your body. You can leave your pubes and head alone, other than your face, but I want the rest of it gone. Don’t forget under your arms, too.”
I knew she was relishing this, but I wouldn’t let her win, even if it meant enduring two weeks of being a girl.
After I had finished my bubble bath, she took me back to her bedroom. A bra and panties waited for me on the bed.
“Put them on.”
I grudgingly complied.
“You know, I think you need something to fill out those cups.”
She opened a drawer and took out a package. I saw the lettering on it. “Breast Forms.” Why would she need breast forms? She wasn’t flat. Then I realized I walked right into her trap.
“You had this planned all along.”
“Good guess, brother. But it’s too late for you to back out now.”
Damn, she was right.
“We need to get you looking more feminine.” She started plucking my eyebrows, eventually reaching the point where they would look OK on a guy or a girl.
She took some cosmetics and applied them to my face. Slowly, I could see myself transforming into a female.
“I hope you are a quick learner. You’ll be doing this every day.”
Mascara and lip gloss added to my appearance, plus a dab of perfume here and there. She also handed me a package of pantyhose.
“I bought these for you, so you won't get runs in mine." Then I was instructed in the correct way to put on hosiery.
Shortly afterward, I had on a pretty floral sundress.
Wait a minute. ‘Pretty?’ Why would I even notice that it was pretty? Was I already adapting to my new role? This confused me.
She gave me a pair of pumps to complete the look.
“You’d better start practicing, so you can walk in those.”
I struggled to keep my balance in the shoes.
“Here, watch me. Pay attention to what my feet are doing.”
She walked back and forth.
“Now, you do it.”
I barely avoided falling.
“Just keep trying. You’ll get the hang of it. There are videos on YouTube for this, too.”
She looked me over. “Overall, I think you make a convincing girl. Once you learn to walk in heels and adjust to your new self, then it will be almost impossible to tell that you are not female. Oh, I know. We need to get you some earrings to go with your outfit. Good thing for you I do this at the kiosk in the mall.”
Before too long, I had newly pierced ears. Studs were placed in them until they healed.
“Now, one more thing to complete the picture.” She gave me a wig to don. “You do look like a girl. Twirl around for me.”
She took a video of me with her phone. “Don’t worry, I won’t show it to anybody. I think I’ll do some more over the next two weeks, so I can see how you have progressed. Now, walk around some more. You need to get used to those heels.”
For the next few days, she gave me more advice on how to carry myself as a girl. Of course, she took advantage of my plight to tease me. “Are you ready to concede?”
I had no intention of letting her see me cave in and lose this bet. But a weird thought struck me. I was getting used to looking like this every day, and actually enjoying it. But I could never tell that to my sister
(End of Part One)
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