His Sister Wants Him to Switch Ch. 01

[This story involves discipline and bodily functions as well as transvestite transition. All characters are 18 or older. ]

Frederika came home from her junior year in college and realized how far she had come temperamentally since she had been living at home and attending high school. She watched her kid brother Larry, now all of 18, as he was finishing his senior year in high school, the same school where Freddie had been a star. She was still a star. This time she was making a name for herself at the university.

Their parents were overseas and probably wouldn't return from their project for at least another year. Freddie, of course, was at college, and Larry was 18, so they decided that he could stay on there on his own until he left for college next year. Larry had always been a responsible boy and they felt confident that with Freddie within reach if needed, everything would be fine.

Freddie looked at Larry and remembered how she had always wanted a little sister. She was now 21. She remembered that Larry had always worshipped her. She even fixed him up with the younger girls in his class who also were in awe of her. He also was proud of her but just a tad jealous sometimes because she had been a top athlete--a lacrosse player, always on attack, and a track middle-distance runner. Also, he remembered that Freddie never worried about having a date because the boys lined up for her. She had glistening auburn hair in a sleek ponytail and a lovely curvy frame with nice-sized but hardly huge tits.

She started thinking again about having a younger sister. And her thoughts focused on Larry. She had always sensed that he was girlish. He paid attention to what he wore and liked to try on his clothes, paying a great deal of attention to his body, always putting on deodorant and aftershave. Once when he had not gone through the clean laundry down in the basement, Freddie saw he was frantic and asked him what the problem was. When he told her that all his underwear was in the laundry, she grinned and told him she'd lend him a pair of hers.

Instead of reacting with horror to putting on girls' panties, he seemed to think it was a reasonable solution. Freddie dug into her lingerie drawer and pulled out a nice pair of pale blue hicut briefs that she knew had enough room in the crotch for his equipment. He didn't shrink from taking the panties from her and Freddie told him, as they were in her room, to let his trousers down and put the panties on.

Larry still was hesitant and Freddie smiled as she looked lovingly at him as she would a younger sister and told him it was all right for him to wear her panties. For his part, it got through to him that this was something he'd wanted to do but had never before summoned up enough nerve--without her assistance now.

So, this was not some sudden decision. Larry had been wracked with indecision every time he began letting his mind wander to consider what it'd be like were he a girl instead of an ordinary boy. He liked the fact that no one expected girls to have to take charge of situations and that they tended to be the ones to decide if it was time to get into intimate stuff with boys, or girls for that matter. He was surprised about how much time he was thinking about this.

All these thoughts were rocking around in his head as he pulled Freddie's panties up his legs. They did feel so smooth and silky, even though they were not special undies, just ones she wore for a day. What would it be like to wear panties like these every day? He couldn't do that unless he really was a girl. Did he want to be one? Did he want surgery, or at least could he start dressing and behaving like a girl?

He found his fresh panties getting wet, dripping precum or whatever from his penis. Gosh, he was already responding like a girl getting excited and wet! But he liked what was happening. Maybe it meant that he really was a girl underneath his male exterior. He knew that everyone had some male and female characteristics. Perhaps he had more female ones than most men or boys did. What did that mean for him?

He began to think about what else was involved in dressing as a woman. He'd have to wear a bra even though he certainly had no tits that needed one. He even remembered when he was little and his sister got her first training bra. Freddie had always been the stronger one and he didn't dare tease her but he did see one of her bras in the bathroom one day and he couldn't resist trying it on. It was tight and he wondered how women managed being encased in them all day. Then he remembered that they had breasts that needed support. He was already contemplating what kind of inserts he'd need to make his bra look like he needed it. After all, he wouldn't get any dates if he were a flat-chested girl.

Larry was embarrassed that just hearing Freddie's mentioning his wearing her panties had aroused him mightily. This led him to pull them up quickly as he put them on. Freddie liked seeing the size of his cock and balls. She watched as he pulled up the panties, for they fit perfectly. Yes, there was that telltale bulge, but they still looked fine.

She liked the way he worshipped her because it meant he would do just what she told him to do, and she was intent on making him into a girl, a girl who would be at her beck and call. He had a nice slight build and Freddie could see him outfitted with the right bra, probably one of her sports bras or one of the now fashionable bralettes.

She had been thinking about what he would be like as a girl for ages. It was weird, she thought now, that she had never visualized him in an incestuous way. Probably it was that she had boyfriends insofar as sex was concerned. Freddie never had had any problem getting a date. Boys flocked to her as both friends and prospective partners. She had given her virginity to a high school friend with whom she was close enough so that she didn't feel she had been suckered into it or had demeaned herself.

And she had not looked back since that event, which was rapidly receding in her memory. There had been plenty of boys with whom she had gone out or been seen with. And she smiled as she remembered that she had only fucked a few of them. That was because she did have a strong sense of self. She didn't care about acquiring the wrong kind of reputation, but it still didn't seem right for her to spread her legs for every cock she saw. In fact, she was proud of the guys she had been in bed with. And yes, she meant bed, not the back seat of some car or in a drunken stupor at a fraternity party. Her focus returned to the present.

She then started to have some doubts as she forced herself to think deeply about what she was proceeding to plan. Was it right for her to assist her brother to change his sex? Just because lots of people were doing this didn't mean it was right for him. Was she just indulging a whim and was it purely for her enjoyment?

Frederika was mature for her age and was used to thinking seriously about decisions. Sure, it wasn't that he was having surgery and the switch would be irreversible. But she didn't even like to think about what it would be for him and for her if it turned out he didn't like being a girl. He might think he wasn't pretty enough, or that no one would want to be in love with him once they found what they didn't expect between his legs.

She was very secure in her identity. It had been mostly great growing up as a girl, and as the elder of the siblings. Even in junior high, when girls go nuts because they have to deal with their breasts popping out and needing a bra, or their not popping out and being the last girl to get a training bra or falsies or both, she had been right in the middle of the group of girls she hung with. She wasn't the first to get her period, but when she did have it, it wasn't such a big deal anymore and she was pleased about that.

She was putting a lot on Larry and she started thinking about how her parents would react. They left her in charge and they come back to find their son turned into a daughter. Would she be able to handle the inevitable inquisition they would subject her to? If Larry didn't like it, and demanded to go back to being a boy, how would she deal with that? It would be hard to force him. He could go see a counselor at school or at church and convince them that he had been led into making a big mistake. Sure, it would be embarrassing but that would pass. She returned to focusing on finding out if he were really game.

"Larry," she began, "you look just perfect in those panties, I hope you realize it as much as I do. I have something very special in mind that I'd like you to give some real thought. I've always wanted a little sister. I've realized just now that you could fill that role."

"Fred," Larry said shakily, "that's pretty weird. Do you mean you would help me dress like a girl? Or do you mean going further--turning me into one?"

"You've wanted to be a girl for a long time, haven't you?" Freddie asked pointedly. "Well, now that's become much more possible than it ever has been, Sure, some people, some kids at school, will make fun of you, but they're not the majority anymore. And you are good enough at sports to be athletic, like I am."

"Will I be regarded as a freak?" Larry pressed her. "I can't see any guys I know asking me for a date." He found it weird to be waiting for some boy to ask him for a date. How would he feel about going out with boys? Would he just attract boys who liked boys? Ugh.

"You'll be surprised," Freddie responded. "Guys you know may have a gay side they have suppressed. They will feel it's OK to hook up with you, because after all, you're coming on now as a girl."

"That's crazy," Larry now erupted. "I'm not queer. But hell, I guess you're right, Fred, because I won't really be sure whether I will want to be close with girls or boys until I try this out. But gosh, if I don't like being a girl, it'll be hard to go back without everyone thinking I'm a total jerk."

"And it's going to be difficult," Larry went on. "Using the bathroom is a big deal."

They're now having unisex bathrooms--so you don't have to use either the men's or the women's," Freddie answered. "Yes, you probably will want to use a stall and sit down on the toilet. But look, you won't even have to deal with periods."

Larry smiled for the first time. "This is getting pretty crazy, that's all I can say, Fred." He mused to himself for a few moments. Finally, he smiled at the sister he had always had such strong feelings for. Then he declared, "But I like it."

"And the locker room will be tricky at first," she went on, not wanting to make a big deal about his assenting. "You'll want to keep to yourself a bit there at first. Some girls will be afraid of you. A few will be very aggressive and taunt you and even try to disrobe you totally. Eventually, they'll get used to your being there. This shouldn't dissuade you, but you and I have always tried to be real with each other, haven't we?"

"Yes," Larry answered immediately. Freddie had been a good big sister. She had explained to him how to behave with girls. She had even brought him along to some parties where he wasn't the only younger boy there and he had met some girls his own age.

"Good," Frederika smiled. "You've always liked my clothes, haven't you? Well, now I might let you wear some of them, the way sisters do. Would you like that?"

Larry sighed but finally let out a deep breath.

"You've understood that I've always thought about this a lot and have wanted to be a girl for a long time, haven't you, Freddie?" he answered.

"Yes, and now you're going to be Kimberly, or Kim, or Kimmy, from now on," Frederika told him. "It's your name so you should get comfortable with it. It will be on all your ID and your school forms. And you'll get a yellow (girl's) report card now that you're a girl. No more blue ones."

Larry forced himself to chuckle at that. "That will be the least of what I'll have to deal with, Sis," he remarked. "If I hadn't thought and dreamed about this for such a long time, the mess that will result for me wouldn't be worth the pain. But yes, I've always wanted this."

"We'll start out by dressing you," Freddie answered with authority. "Lots of my stuff would fit you and I'll spring for whatever girls' clothing, like your own lingerie, that you'll need and want. Any physical change--like surgery--should wait until you see how it works and how you react. Nothing that major until you're really sure."

"I've been accepted for college," Larry replied, "I really don't want to endanger that. They might think I'm too weird to enroll."

"Not at all," Freddie snapped. "I'm glad that you're going to be at a coed school which has always been coed. These days, they're even looking for smart and acceptable trans people. And nobody except the religious crazies gives trans people a hard time any more. You'll even have a support group there. I know, I know, you don't want to be a crusader. Fine. You'll have plenty of people who will help you, though, if you ever need it. Besides me," she grinned at him.

"Will I be regarded as something strange?" Larry asked plaintively. "You know that I'd love being a girl. But how can it happen with school and everything?"

"Today, it's much easier," Freddie assured him. "I've been reading up on it. All we have to do is take you down to the Vital Stats office at City Hall and you can file a change of identity form. From then on, your official status will be female. I'll go with you to school and sign off--remember that Mom was wise enough to make me your guardian in case some signature for anything like this would be required--so that you can be registered as a female there."

Larry still looked worried about the kids who knew him well at school and elsewhere.

"Larry," Freddie continued, "this is happening all over today. I'm telling you; I know all kinds of trans people at college. I'm going to take you shopping for nice clothes tomorrow. You may or may not ever want surgery. Unfortunately, I don't think it's yet always worth it in terms of what it adds."

"I'm definitely not ready for surgery," Larry responded quickly. "But you've put this in a very attractive manner, Freddie. I really want to thank you because you perceived that I'm really a girl at heart. Mom and Dad never would. How do you think they'll be when they find it, and when they come back?"

"You're right," she continued, "the first day will be tough. People don't react well to change. And a lot of them may want to do it, become the sex they aren't, but they're too afraid to try it."

"And as for Mom and Dad," she went on, "this will have happened by the time they get back. That puts it in a whole different posture."

"This is starting to sound better," Larry said with a more cheerful air. "I guess you figured me out, Fred. It's true: I've always wanted to be a girl and it'll be fun to be your sister."

Freddie grinned. "Come with me into the bathroom," she said, with only a slight imperative tone in her voice. "I'm going to show you how to go like a girl."

Larry was still enjoying the prospects he saw for himself. "I guess this is OK," he managed to say, "it's still sort of embarrassing."

Freddie took him by the hand. They walked together down the hall. When they reached her bedroom, Freddie told him to unbuckle and let down his slacks, then to take off both the slacks. "I'm going to put you in a dress and a skirt, so you learn how to wear them and how you deal with them when you need to go," she explained.

She then led him into her ensuite bathroom. "Now before you sit yourself on the toilet, lift up your skirt so it's out of the way and then remember to pull your panties down on your thighs, not too far," she reminded him. "Girls just pull their panties far enough, so they don't get in the way. If you pulled them way down, they might touch the floor, which could be wet or have all kinds of crud."

She looked at him with the pale blue panties now down on his thighs.

"Now take your hand and tuck that penis right down so when you pee, it will go straight down," she directed him. "You've peed sitting down before. Now you have to do it that way all the time. There are no urinals in the girls' room."

"This is going to be uncomfortable," Larry complained.

"After a while, you won't even think about it," Freddie answered sharply. "You can still aim your pee, and we girls with female equipment cannot do that as well as you can even when sitting rather than standing."

"Now go ahead and pee," she said. "It's just me so you don't have to be shy."

It took him a while to release because he had been aroused by all this talk and had to ease his hard-on so that he could pee. But finally, the stream emerged and hit the water in the toilet bowl.

"Great!" Freddie exclaimed. "You're having your first pee as a girl, Larry! Now take some toilet paper and wipe yourself off. Girls always wipe after they pee. Front to back. In your case, just wipe the tip."

"We won't bother about the other," Freddie added. "But as a girl, you have to wipe your bottom very thoroughly. Girls don't have residue or dingleberries or anything like that. A girl has to be scrupulous about that. If you stain your panties, you're going to be sorry."

"Now wash your hands and we'll try on some stuff," she went on.

When they were back in her room, Freddie took out a dress and a skirt. The dress was a simple one, but it did have a belt. The skirt had a pretty pattern.

"Dresses often go on over your head, but many that zip up can be put on up from your legs," she told him. "Now try it and you'll see." He went ahead and did what she said. The dress hung nicely from his shoulders."

"You won't need shoulder pads," she giggled. "Now sit in that chair," she said. "You have to learn to cross your legs right. Girls don't let their dresses ride up and show their panties."

"Are you going to go with me to the school office to get things set up?" Larry asked. "I'm worried that they will give me a bad time."

"I'll go with you," Freddie assured him. "I know Miss Stanton well. She's still the principal, right?"

"Yes," Larry said. He was deathly afraid of her. He wondered how Freddie could be so different from him in her confidence. He was starting to realize that he might turn out to be Freddie's weak sister and that didn't sound so good. But he figured that he liked being a girl and that it was better to be shy and even weak as a girl than as a boy.

"Don't worry," Freddie continued to tell him. "We'll work this out for you with them."

"I'll have to do things for myself once you go back to college," Larry said very tentatively.

"Yes, you will, Kim," Freddie used his new name with a wide smile.

"Kims do tend to be sort of weak at the knees," Freddie told him. "I'll love you as my sister, Kimmy, but I'm also going to try to get you to stand up for yourself. You really haven't had to do that as a boy, have you?"

"Fred," Kim answered, "boys get a certain amount of deference. I do know how to fight, and I really don't enjoy it, but I've stood up for myself when anyone gave me a hard time. I hope I won't have to do that in cat fights. Girls aren't supposed to fight like boys, are they?"

"No," Freddie replied, "you have to get beyond that. You're a high school senior. That's too old to get into fist fights or any fights. But you'll need to show some spirit, so boys won't walk all over you when you appear as a girl."

"Freddie, you seem to understand that this is something I've always wanted," Kim said very emotionally. "I'm afraid that I'll screw up and end up being regarded as a jerk or a freak."

"You've actually been well-liked at school and elsewhere," Freddie rejoined. "But I want you to get this anxiety out of your system now. Yes, you are going to have to show some bravery. But I know you have it in you."