His Sister Wants Him to Switch Ch. 01

"I guess so," Kim conceded. "I wish you were going to be here for more than a few weeks. Won't you stay a little longer?"

"I don't like to hear you whining, Kimmy," Freddie said rather sternly. "I don't want to have to discipline you, but I will if you don't act like this is something you want and feel confident about."

"You have no reason not to approach this in a very positive spirit, Kim," she continued. "I'm giving you a lot of support--in fact, I'll go with you to buy you some things and you have free reign on all my clothing that I haven't taken to school. So, there are skirts and dresses and blouses and socks, and yes, bras and panties and hose. But if you're going to act like a sniveling little girlie, you're going to get it on your little tushee."

"Please don't punish me, Fred," Kim pleaded. "I'll be good, and I'll do what you say." She was suddenly remembering when--two years ago--their mother became angry when Larry responded to a maternal request with a four-letter word. The shocker came when his mom called on Freddie to spank him. He knew he deserved it but that didn't make it any easier to take; Freddie hadn't teased him or anything like that--she just spanked him thoroughly.

"I don't like pleading," Freddie observed. "I like women who want to succeed. I'm sorry but I'm going to have to spank you, sweetie. Take down those pants and then your panties, and get across my lap, NOW!"

Kim was surprised although she later realized she shouldn't have been. She had great respect for Freddie, but she worried that she couldn't live up to her model sister. In fact, she wondered deep down if Freddie really wanted at some level to be a boy.

She unbuckled her belt and lowered her slacks. Then she put her thumbs in the waistband of the panties Freddie had lent her and pulled them down just a little below her bottom. She then positioned herself across her sister's lap, as Freddie was pointing to the place where she wanted her.

Kim, as Larry, hadn't been spanked much in recent years. Her parents did still spank him when he had misbehaved seriously. And while they were gone, Freddie had spanked him when he came in later than had been allowed. Now, Freddie, who was now thinking of him as a girl and a her, wanted her to obey so that she wouldn't have to get her out of trouble.

Freddie lay her hand on Kim's bottom. She thought that it already looked girlish with the panties bunched down below her bottom. Freddie started spanking, fairly hard at first and then very hard. Soon, Kim was crying out.

"Get up," Freddie snapped. Kim hoped this meant the punishment was completed. But Freddie ordered her to bend over the bed.

"Oh God," Kim thought, "she's going to use the cane! Ayyyy!"

Freddie took the cane from her closet. It was wood-colored but made from rattan and very thin and whippy. She lay it on Kim's already red bottom. Then she drew it back, and expertly flicked her wrist when she aimed the cane right at the middle of Kim's bottom.

"I'm going to get all the naughtiness out of you," Freddie announced. "You are going to be the best-behaved girl in your school. I want you respected, by both girls and boys. And if you do what I tell you, Kimmy, you will be."

Then she drew the cane back and fired a stinging stroke at the base of Kim's boyish bottom.

Wow, that hurt, Kim thought. She is one tough woman, the way she brandishes that cane. Then the cane struck again, and Kim cried out as the stroke hit her above the middle but carefully placed so as not to hit too high.

"I'm going to let you off today with three," Freddie told Kim. "But I'm also going to have you wear these tight little girly panties that will remind you how you will feel if you wear tight panties like thongs. These will make you feel juvvie, but that's something you need to experience as a girl. You're going to feel the tight panties more because of your special equipment," she smiled. "But back when I was just 'developing', it was awful when Mom made me wear those little girly panties because they were so uncomfortable and made me feel so childish."

"Oh, please, Fred, please let me wear these panties I have on," Kim asked, making sure not to whine or plead. "I want to please you and learn so much from you."

Freddie decided that she shouldn't come down too hard now and that she would let Larry go ahead just with becoming Kimmy. On the whole, she thought it would work but that Kim wouldn't have the presence that she, Frederika, had. She probably wouldn't end up dating one of the top guys. But Freddie was determined to make sure she wouldn't be a total loser.

"I want to see you get into this," Freddie told her. "You'll have a lot of nice clothes and I want them kept clean and neat. If you wear them, make sure you do laundry or take them to be cleaned when they need to be. You're going to be here alone, so I don't want you jerking off like you did when you were a boy. You have to focus on acting like a girl."

"I'll be here for a couple of weeks," she stated. "We're going to work on stuff like learning to wear heels and making sure you have a training bra with inserts that all fit you. By the time I take off you will know what it's like to be a girl for real."

Freddie was as good as her word. She took Kim shopping and picked out a wig that accentuated Kim's features. Then she shopped with her for a training bra and charmed the salesgirl, so she helped them find just the right size, as well as the right inserts.

Freddie had Kim try on a lot of Freddie's dresses and skirts and blouses. But she took her shopping for lingerie, especially panties. She made sure Kim had a good supply of plain white cotton panties and then some nice patterned, striped, and pastel ones that would make her feel especially girly.

She had this time off from college and decided to use the time to teach Kim how to behave in a feminine manner. This meant watching Kimmy walk in both flats and heels. She also taught her how to dress, apply makeup, and learn about the entire world of cosmetics, jewelry, and accessories.

It became clear to Freddie that Kim was going to be a different kind of girl from what Freddie was like, and this was not just because Kimmy had a penis. Yes, she needed to use depilatories of various kinds, and wear modesty devices to avoid major bulges in her panties.

But she saw that Kimmy was not assertive, would take what came to her but might not struggle to be recognized for her attractive qualities. Freddie could fairly be described as a success, both when she was in high school and already in college. She was a natural leader, even a commander at times.

Kimmy had been a shy boy and now she would be a retiring girl. Freddie would have to train her to make herself enticing to both men and women. She might want to get it on with both and with trans people like herself. She was decent at sports, and this made Freddie's task easier. But Freddie forced herself to remember that Kim was not likely to be a standout as Freddie was on the field.

Freddie knew that Kimmy would sulk, just as she had when she was Larry. Whenever she noticed that kind of attitude manifesting itself, Freddie jumped on it. She trained Kimmy to lift her skirt and take down her own panties. Then Freddie would tell her whether she would be spanked or caned. Freddie also had a leather strap and a belt she might use but preferred her hand and the cane as needed.

Kimmy became very afraid of Freddie's cane and Freddie played on that. She would get Kim to act more assertively by telling her that she had a caning in her future if she didn't try harder. Canings became more frequent.

Freddie helped Kim get dressed the day they were going to shop for her own lingerie and some other clothes. To avoid any confrontations in their neighborhood or nearby, Freddie drove them to a mall some distance away. She dressed very nicely and put together a flattering outfit for Kimmy. The wig selection she had picked up was working well. Also, Larry didn't have huge feet and Freddie's were large for a woman: some of her shoes did fit Kim.

They arrived at a department store and Freddie led them to the intimate apparel area. A thirtyish saleswoman appeared and asked if she could help. Freddie put on her most friendly but competent air and said she was helping her sister pick out some things for when she went away to school.

The saleswoman, who introduced herself as Grace, took them to the juniors area, and Freddie started checking out panties. She had had Kim try on one of her sports bras, so she had a size and asked Grace to show them some nice bralettes and sports bras in that size.

"No, we're not going to try them on here," she said peremptorily to Grace. "This is a new experience for her, if you get my drift." She raised her eyebrows as she glanced first at Kim and then at Grace.

Grace smiled and said, "Yes, I do, Miss. We've been getting more and more customers like your...sister."

"You see, Kim," Freddie said privately to Kim, "people have been adjusting to this now."

Grace encouraged Kim to look through the panties and the bras to see what she liked. Then the saleswoman took Freddie aside and said quietly to her, "I'm happy to come into the fitting room with you both if you think it will help her see what's right on her. I was serious that I'm seeing a lot of 'special girls' like her these days."

Freddie smiled at Grace and after introducing herself properly and encouraging Grace to call her Freddie, agreed that Grace's presence in the room would be very helpful and she thanked her for bringing up the idea. She mentioned to Grace that she wanted to get Kim her first garter belt and asked if Grace could bring one in when they went to try some things on.

"Of course," Grace responded, "and I'll also get some hose. We have a few lines now that girls like Kim seem to find easier to put on. I assume you want ones for the belt as well as some full pantyhose?"

Freddie confirmed that she would find that very useful. Grace went to find the garter belt and hose while Freddie joined Kim and approved her selections of panties and sports bras. Freddie walked with her over to select a bralette or two.

Then she told Kim they would go into the fitting room to try on some of the things.

"Don't worry when the saleswoman joins us," Freddie said quietly. "She knows about you, and she told me she's had quite a few customers in your position. So, I hope you'll keep cool when she comes in. She's older than I am so she's seen plenty of people with your...equipment.

They got to the fitting rooms and the woman at the desk gave Freddie a key with a number on it corresponding to the fitting room. They went into it and Freddie found it was larger than usual, perhaps because the woman saw that they were two and Freddie had told her that Grace would be joining them.

She told Kim once they were in the room to carefully take off her blouse and skirt, and then her bra and panties, as well as her hose and shoes. Kim still was skittish, but Freddie kept assuring her that this was normal. She didn't mention that they usually weren't purchasing any entire wardrobe. Freddie also knew that once Kim tried on the lingerie, it was regarded as sold. So she made sure Kim liked everything and that the fit would be right.

Grace knocked and Freddie told her to come in. She helped Kim put on the bralette and then the sports bra. Both Grace and Freddie agreed that Kim needed a slightly larger bralette so Grace said she would get it for them once Kim tried on the other items.

Kim found the garter belt strange, but it fit, and Freddie helped her roll up some nice hose that Grace had brought and then attach the garter clips. Freddie looked at Kim in a sports bra and the belt and hose. She felt she was actually getting a younger sister now.

Grace confirmed that everything else fit and left to get another bra. When she returned, she also had the right inserts and Kim tried it on and said it did feel comfortable. Then Grace took a pink plastic device out of a box and Freddie nodded her assent.

"Kim, this may surprise you, but I'll explain what it is," Grace said softly. "Sometimes you want to minimize your bulge down there," she said, pointing to Kim's equipment. "You can put this on, and it will point your shaft down so that when you snap it on, you will have a nice flat femmy front."

"Yes," Freddie said quickly. "You don't need that all that much these days, but sometimes you may not want to broadcast who you are, if you get my drift."

Kim looked surprised and a bit wary. Freddie took the device and carefully helped Kim place it around her cock. Kim looked like she might shed a tear, so Freddie hugged her and kissed her lightly.

"Don't worry, dear," Freddie said warmly, "I want you to have everything you might need, and Grace is right that this might come in handy sometime."

Then she motioned to Grace to take the device off and Grace did just that, placing it back in its box.

She gathered all the lingerie and told Freddie and Kim that she would meet them at the register out on the floor.

After she left, Kim looked at Freddie, "That was sort of a shock, Fred. I didn't know they had those kinds of things."

"It's a hangover from the days where you had to be very careful," Freddie advised her. "You may or may not need it, but when you want to make an impression..."

"I think the trans people are making it possible to phase out that kind of stuff," Kim commented.

"You may be right," Freddie said, "but thank you for not making a fuss about it." She wanted to finish up here while Kim was still in a cooperative frame of mind.

They took the packages from Grace after Freddie had paid with one of her credit cards. Freddie went out of her way to thank Grace in front of the other employees for helping them so well. Kim realized it would be nice if she did that, so she added her thanks and smiled at Grace.

They went on to have Kim try on some separates and nice blouses, skirts, and blazers. Freddie wanted to see what kind of taste Kim might already have and was pleased enough with her selections that she went ahead and bought them for her.

"Now this is where ladies lunch, so you may as well get accustomed to how it feels."

All proceeded nicely and after they had had coffee, Kim told her sister that she did need to use the rest room.

"It's always the ladies in places like this," Freddie said with a grin. "Let me go with you this first time."

"Thanks," Kimmy said sweetly. "That will be really nice of you. I'm still a little shaky about this."

They walked to the ladies' room and fortunately, it was almost empty. Freddie took Kim to a rear stall and after they got inside the tight quarters, she watched as Kim lifted her skirt above her waist and pulled her panties down below her bottom. Then she sat on the toilet and reached down to make sure she pointed her cock down and held it, so she peed directly down into the bowl. That done, she let go and Freddie heard the characteristic sound of a girl's pee stream hitting the water.

After the stream fell off and stopped, Kim looked up sheepishly at Freddie and said, "I'm sorry, Fred. I have to, you know, make a doody."

"Cute word," Freddie thought to herself. Then she just had a straight face on and told Kim, "Sure, go ahead and make it. We're the same that way as boys, as you know."

After a little wait, Freddie heard a plop and then another. Kim looked up and said, "I'll wipe now." She took some tissue and wiped the tip of her cock and then pushed the tissue under her scrotum and through her anal area. She brought it up and there was some brown on the paper. She took some more tissue and ran it through the same area again. When she looked at it, it was clean.

Then Kim went on and flushed the toilet.

"It's better," Freddie said calmly, "to put yourself back together and then flush." She watched as Kim pulled up her panties and let her skirt down, once she was clear of the toilet.

"Very good," Freddie said. "Now let's go and have you wash your hands and check your makeup in the mirror."

When they were back in the car, Kim thanked Freddie for both taking her to shop and buying all the nice clothes for her.

Freddie said that it was the least she could do and that she loved Kim and wanted this to work. "I want you to be confident as a girl, sweetie," she said warmly.