Part Two - Training

By the end of the first week, I had almost mastered walking in heels and had gotten more adept at doing my makeup.

Jessica continued to tease me. “How about it, bro? Do you want to give up yet? You could end this by admitting that being a girl is better.”

“Hell no, I won’t give you that satisfaction.”

“OK, but remember, you have another week of this to go.”

“That’s difficult to forget.”

“You know, I bet you secretly like this.”

“Yeah, right.” I already realized that, but I wouldn’t tell her.

“Well, we need to take your training to the next level. Come on, we’re going shopping for dresses.”

“No way, Jessica. People will know I’m not a girl.”

“They won’t. No one will notice.”

I wasn’t happy but went along with her. We went through several stores. She bought me a dress she said would look good on me. I purchased one I secretly liked, at my sister’s urging. A stop by Victoria’s Secret resulted in some lacy lingerie for me.

Since the bet finished at the end of the week, I asked her why we would do this. She responded that the clothes would fit her, too. She’d keep them for herself and pay me back. Then she added, “Maybe you’ll want to hold on to them.”

Was she reading my mind?

When we came home, Jessica had me model the purchases for her.

“Wow, that dress looks good on you, bro. Any guy would do a double-take when he saw you. You’re one gorgeous chick! We should go out dancing tonight.”

“Oh, come on. The mall was one thing, but going out to a club?”

“It’ll be fun. I’ll tell people you're my cousin. Maybe we’ll meet some cute guys. They’ll certainly be checking you out.”

Despite my misgivings, we went to a club and danced with a couple of the guys there. I introduced myself as Jessica’s cousin, Brenda. By the end of the evening, we had agreed to go out with them on a double-date that coming Friday night. On the way home, the reality of the situation hit me.

Jessica asked if I had a good time.

“All I can say is that two weeks ago, I never imagined that I would wear a slinky dress and heels, plus dance with some guy who was unaware I was not what I appeared. No one even noticed when I went to the ladies’ room.”

“See? I said you looked good. I meant it, too. Now we can plan for Friday night. There are still a few things for you to learn, and real-life experience is the best way to do it.”

“Like what?”

“For starters, you’ll see how nice it is when a guy treats you like a lady. You had a taste of that at the club.”

“And?”

“I’ll tell you the rest on Friday night. In the meantime, keep practicing your girlish moves. That night will be a kind of final exam for you.”

Part Three - Final Exam and Graduation

When Friday evening arrived, I asked Jessica what further tests she had planned.

She explained, “Remember, you’ll be on a date with a guy who thinks you’re a good-looking chick. He’ll probably try to kiss you at some point. Let him do that and kiss him back. By the end of the night, I want your lips wrapped around his cock.“

“Wait a minute, Jess. That isn’t part of the deal.”

“Oh yes, it is; I told you had to do things a girl would do, which includes giving your date a blowjob as Brenda.“

I grumbled at the thought.

“Quit whining; he's a nice guy. You'll enjoy it. I think he liked meeting Brenda. It seemed she was enjoying his company, too. So, before tonight is over, his cock will be in your mouth. Then swallow it all once he cums. Do that, and you'll win our bet.”

That night, the guys took Jessica and me to dinner, followed by a movie. In the darkened theater, Jack, my date, held my hand. I didn’t shy away. Instead, I leaned over and gave him a quick kiss. I could almost see him smile in the dark.

Later on, the four of us went back to Jack’s place and made out. Inside, I was still amazed. Dressed as a girl, I kissed a guy and liked it. What had this transition of the last two weeks done to me?

My hands rubbed Jack’s crotch. He was getting hard.

Jessica saw me and grinned.

“Go ahead, Brenda. Do it!”

She announced to the guys, “Brenda’s never sucked a cock before. But she told me she wanted to try it with you, Jack.”

I guess I was at the point of no return. It would have been difficult to back out before. Now, I had no choice but to move forward.

I told Jack, “I wish she hadn't said that, but yes, I’ve been thinking about it since the other night.”

That wasn’t exactly true, since I didn't find out it would happen until shortly before Jessica and I left to meet the guys. But I was going through with it anyway, so that was a moot point.

Jack immediately stood up and began taking off his pants and underwear. Finally, free of restraint, his cock stood straight out.

I got down on my knees and kissed his erection. My tongue and lips explored his testicles. Then I grasped his shaft., my mouth enveloping it. Trying to remember what I’d seen in movies, I followed those recollections.

My hand pumped while I sucked gently on the head of his penis and swirled my tongue around it. Once my sister saw I was doing fine, she got down to business with her date.

My attention returned to the erection in front of my tongue, I licked the length. Then I swirled it around the head. I bobbed up and down on Jack. To my surprise, I took him completely into my mouth. I kissed the head again and licked it some more. Then I went back to face-fucking him.

Neither guy said a word, but both sighed as we two girls continued to suck their cocks.

Jessica said I’d enjoy this, and once again, she was right. I continued pumping and sucking until I felt Jack tense up. Then he ejaculated into my waiting mouth. I swallowed as much as possible, then licked his cock clean from the leftovers.

Jessica had finished her guy, too.

Jack said, “Wow, Brenda, I can’t believe you never did this before.”

“Yes, this was my first time, Jack, but it was fun.”

Then I whispered in his ear, “Let's do this again one of these days.”

Out of the corner of my eye, I saw Jessica smiling.

The evening ended, we kissed our dates goodnight and drove home. In the car, Jessica remarked, “It looked like you enjoyed yourself with Jack.”

“Jessica, I hate to admit this, but you have won our bet. I never thought I’d say this, but the last two weeks have been fun. I enjoyed being a girl and want to keep on doing this.”

“This is what you get when you argue with your sister. She is always right. But the truth is, bro, you won. You didn’t back out of our bet.“

“Perhaps we both won. I said that you would have to do anything I asked if I won. But all I want from you is to help me continue being a girl any time an opportunity arises. We probably shouldn’t tell Mom and Dad. I doubt they’d approve or even understand why their son suddenly wants to be their other daughter. They’d give you grief for letting this happen.”

“You got it, bro. I’m happy to help you. But let me tell you something else. Early on, I realized you were enjoying this. I let you believe it was your secret. When I planned this, I guessed you might last two weeks if only to spite me. But it was worthwhile just to make you endure it. I didn’t expect you’d embrace being a girl, but I’m glad you did. Now you realize what I have been telling you for so long; being a girl is fun.”

“I will hate returning to my old self once Mom and Dad get home,” I said. “But I’m sure we can figure out some way for Brenda to return, especially for the next time we go out with the guys. Brenda and I can’t wait!”

“We have another day before this ends. How would you like to spend it?”

“Oh, I don't know, Jess. Being like this is nice, in itself.”

“Hey, let’s go shopping again. I remember seeing this cute, strapless dress that would look great on you. You’ll need a strapless bra to go with it. A girl should have one or two for her collection. When we’re done with that, we’ll go to the cosmetics counter in the store. You can have a professional makeover. I don’t think they’ll charge anything, but if they do, it’s on me.”

“Wow, thanks, Jess!”

“Don’t worry, bro, I’ll make you pay in other ways.” She laughed. “It’s my duty as your sister.”

I was able to see Jack again as Brenda. She happily got another mouthful of his cock, sharing the details afterward with her sister. Amused, Jessica said, “I’ve created a monster.”

But one barrier remained. Jack would doubtlessly want to take Brenda to bed. What would he do when he found out I wasn’t a biological woman?

Jessica said, “I don’t know. He’ll find out, eventually. You’ll just have to think about it. Maybe he won’t mind. He could still screw your butt.”

“What the hell,” I said. “I’ve already sucked him off twice and loved every minute of it. Why not let him do my ass, too? Damn, Sis, you really have changed me.”

Jessica smiled and said, “My project with you has far exceeded my expectations. You’re in an advanced class, now. Getting Jack to screw your butt is your next assignment. Managing the project is up to you, but I expect regular status reports.”

After much thought, I mustered the nerve to tell Jack about my real self. To my surprise, he said he’d already guessed that but didn’t care. As far as he was concerned, I was the hottest chick he’d ever met. I kissed him, relieved that my fears of rejection didn't come true. Now, this hot chick regularly enjoys his cock in her mouth and butt.

My sister and I moved out of the house into different apartments. I get to be Brenda much more often than when I lived at home. Jessica and often get together, but mostly as girlfriends, rather than sister and brother. Mom and Dad still know nothing about my alter-ego.

Who would think that making a ridiculous bet with my sister would change my life?

I’d say I graduated with honors.