A Sister’s Bet, Parts Two and Three

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Part Two – TrainingBy 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 isvecbahis 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 isveçbahis giriş 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 GraduationWhen 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 isveçbahis yeni giriş 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.

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