Slowly replace his clothes (Sisters POV)

It's been one week since you got your brother to replace all his underwear and got to enjoy the best show yet as you watched him panic over getting lost in the store and almost faint as the shop assistant went over to help him. After that you've just been having fun watching him act all skittish and nervous as he goes everywhere wearing panties. Every so often you'll hear him trying to think of a way to get new underwear when he's in his room alone but because of the hypnosis he can ever come up with anything. You decided that you would need to wait a little while before doing anything else as he seemed a little suspicious after the shopping trip but now your starting to see the effects of the hormones you've been feeding him when you go to the gym. It's nothing big yet but you can tell the hormones and workout have been filling out his butt and any day now his nipples will probably start getting sensitive and swell up as his breasts start to grow. You can't wait to see all the changes progress but to prepare for that it's time you start swapping his clothes out for women's clothing. You plan on doing it a few pieces at a time so he wont catch on until he has a bunch of girls clothes in his closet, you still aren't sure how you going to handle things then, if you'll keep acting like it has nothing to do with your hypnosis or not, but you can decide on that later.

First you head over to your brothers room and tell him that the laundry is done then "Sleepy time". "Now when you go down and get your clothes from the laundry room you wont notice that two pieces of your clothes have been replaced by a pair of women's jeans and a woman's tee shirt, you'll put them away in you closet like normal after that you'll be able to notice them if you see them and pay enough attention when looking in your closet. This will happen every time you pick you your laundry from now until I say otherwise". Just as you think your done for now you remember how he was talking about needing a hair cut recently so add on "also you'll no longer want to cut your hair and will instead want to try and see what it's like growing it long, and you wont be as adverse to the idea of wearing women's clothes, you wont like wearing them but you wont be as uncomfortable with it either". Satisfied you wake him up and leave so that he can get to work on following your new command. The clothes you're having him pick up don't look like women's at first glance, just a standard pair of women's cut jeans so they'll have a different fitting around the waist and butt and the tee shirts is just a plain blue shirt that again will just fit differently since it is women's cut.

A few minutes later you go check on your brother and your dream situation is happening, he's sat there wearing the new jeans you had him pick up and one of his tops completely unaware that they are made for women. You can't believe that he's really wearing them without wondering where they came from, did he really not notice that they aren't actually his.

Brothers POV

In the morning you sister came to let you know that your laundry is ready so you went and picked them up and got dressed. You didn't pay much attention to what you put on and just grabbed a pair of pants and a shirt out your closet but where pleasantly surprised. For the past few day's you've noticed that you pants haven't been fitting as well and they feel tight on your arse, probably from your workout sessions but your last girl friend was saying how she wished you had a better arse since yours was so flat so its a change your happy about. However this meant that you were thinking about buying some new pants that fit better, but today the jeans you pulled out fit perfectly, it was great, they are a little tighter fitting around your legs than most of your jeans but they feel so much softer against your hairless legs and they have a bit of stretch to them as well. That was another problem you found, now that you've started keeping your body clean shaven your clothes feel much rougher against your skin, you still aren't sure why but you keep shaving yourself in the shower, not that it's a big deal though. Either way you are really glad you had a pair of jeans like these hidden in your closet, if only you could find a top that fit better as well, you assume that the workout is making your peck bigger as well because along with your pants not fitting right you've started having your tops chafe your nipples all the time making them sore. You looked online for some solutions and they suggest wearing band-aids on your nipples but that was mainly for runners, you really want to find a solution you can use everyday without needing to put on new band-aids when you wake up. You also saw suggestions for wearing a training bra or a camisole but those were for young girls going through puberty so definitely didn't apply to you.

A few days later and you found it, you pulled a blue tee shirt out your closet and when you put it on, for the first time in almost a week, your nipples didn't feel like they were getting rubber off. The top didn't fit very well and was quite tight around the arms and waist but that was irrelevant compared to how much better the soft material of the top felt. The sensitivity of your nipples has only been getting worse as days go on and your thinking you may need to go to the doctors about it but for now at least you know this top helps. You decide to first go and ask your sister for help, it's an embarrassing topic but you don't really like going to doctors so you'll try anything first. "Hmm, don't take this the wrong way but it kinda looks like your growing boobs" you sister say's it like it's no big deal but you immediately panic "What do you mean I'm growing boobs!" you yell. "Relax I don't mean real boobs, some times when you change your lifestyle choices it can effect your bodies hormones, since you changed diet and exercise so suddenly that's probably what's happening" she explains although you don't know how she knew all this off the top of her head. "Well then I'm stopping both of them" you say but your sister advises against that "if you stop now you're just going to confuse your body even more and probably make things worse, if you just give it time to adapt toy your new lifestyle it should fix itself soon enough". You find that hard to believe and give you sister a sceptical look "are you sure?" you ask, "almost positive, I was watching a nutritional science documentary on tv and they talked about how it could effect the body like this, you just have a hormonal imbalance right now which is giving you man boobs it'll go away, although I'd suggest wearing a camisole to help until then and if they get too big maybe a bra to stop them sagging and giving you stretch marks, the stretch marks wont disappear even if the boobs do". That matched up with the advice you saw when you looked yourself online so maybe your sister was right. You decide to go buy some more tops that are like the one you are wearing and some pants like the ones from earlier this week along with some camisoles to help you get by until your body calms down.

You go back to your room and take off your top to see what brand it is so you can get more but are shocked to find it's a woman's top. How did this get into your closet, you have no idea, although it does explain why you never saw it before. It also makes sense that if the hormone imbalance is making you grow breasts that women's clothes would fit better but all that doesn't help you understand why they are in your closet to begin with. You find the jeans from the other day and find the same thing, they are women's jeans. Thinking back it was weird that they were bigger around your butt yet still fit your waist like your other jeans, now you realise that's because they are designed for a woman's body type. Nothing seems to make sense, why did you start wearing panties that turned up in your draws, why did you then replace all your underwear with panties, why are woman's clothes turning up in your closet and why does your sister seem to be so calm about all this and know so much about your problem. All of this feel's connected somehow since it all involves you wearing women's clothing but you can't think of what it is that could join these things together. You decide to tackle one problem at a time, whatever it is doing all this doesn't matter right now. What matters is that you need clothes that fit your body until it goes back to normal so you head to the shops to get what you need, you decide that you'll just look for men's alternatives to everything like vests or under shirts for your nipples and bigger pants with belts for your bigger butt.

After getting to the store you notice a problem, you try on lot of different pairs of jeans and other types of pants but they all have the same problems, first of all if they are big enough for your ass they are too big for your waist, but if they fit your waist they are to small for your butt. Second they are all so rough and itchy on your smooth legs, because they are new and not worn down it's even worse than the jeans you currently own. You find similar problems with the vests and undershirts, they don't fix the problem of hurting your sensitive nipples and you can find any shirts that don't hurt either, they all also feel rough against your hairless chest. After about an hour of picking out potential solutions you start to lose hope. As you're walking around the store looking for the next thing to try on you walk past the women's section of the store, you look over at it and remember how the women's jean's and top felt, they were so much softer against your skin and fit so well. You try to tell yourself to forget about it and keep looking in the men's section but a part of you think's why not just try one thing and see if it's better, there's no harm in just trying right?

You sneak over to a rack of camisoles and grab one in your size then almost sprint back to one of the male changing rooms before someone can see you. Once you get there you take off your top then, with shacking hands, you pull the camisole over your head. As soon as its soft cotton touches your nipples you let out a soft sigh, finally something that doesn't feel like sandpaper, there's no way you can go back to trying on more men's clothes after this so you admit defeat and decide to change your plans. You decide to buy more women's jeans along with some camisoles, you figure if you are wearing a camisole under a normal top it can fix your chafing problem and stop you from embarrassing yourself since you'll still be wearing men's tops. You decide it's best to test that first and put you top back on over the camisole, the result wasn't the best, it didn't feel as bad as before but it was still uncomfortable since your top is still to tight around your bust. After letting out another sigh, this time a one of defeat and you decide you might as well go all in and just buy some women's tops to get the best effect.

After that it was like the flood gates opened as you let yourself forget about the embarrassment and focus on the comfort. You spend another hour going through the women's section picking out some things you find the least embarrassing to wear and trying them on to make sure they fit. In the end you have 7 camisoles, enough to wear a new one everyday of the week. You also have 5 pairs of jeans and a pair of linen trousers as well as 2 pairs of joggers and a pair of leggings for lounging around in. You only tried the leggings out of curiosity but they were so comfortable you kept a pair just for wearing at home. You also have 10 top's in a few different styles, some tee-shirts, some are long sleeve and one is a jumper. You even decided it was best to get some new gym gear which was when you saw the sports bra's, you didn't want to wear any bra's but couldn't help trying one on, after trying on all these new clothes you get swept along with the flow and once you tried it you felt stupid for not doing so sooner. It helped so much with your problems so you bought 3 sports bra's for the gym and 2 training bra's, in the end you were too scared of them growing bigger and giving you stretch marks and bought them to stop that. As you were leaving the store with you bag's in hand you can't help but think you went overboard it was like you were possessed once you got started you couldn't stop, is this why women loved shopping so much? No it felt different, all your worries from this morning came back and now you were sure something was wrong. There was no way everything that's happened was a coincidence and you're almost positive your sister must know something about it, you make a mental note to keep a closer eye on her to try and figure out what's going on.

Sisters POV

You can't believe how well everything has gone, all you were going to do is slowly slip some clothes into your brothers closet but now he's just came back with bag's full of women's clothes to replace his own with. The best part is you didn't even have to use hypnosis to make him do it so surely he has no idea that you're the one behind it all. Looking in his bags you are amazed, he's even got some bra's! you think to yourself in shock. This has moved your plan forward massively and you now have to think about how you want to change things to adapt to this. You would really like to add a more feminine twist to his clothes with some skirts and lacy items but that's probably better off happening when his boobs get bigger and he need's new bra's. Instead it's time to start changing him mentally, you can't make any sudden changes or the hypnosis wont work long term if he doesn't accept it so maybe something small like making him walk and talk in a feminine manner and use girly gestures. Or maybe something more impactful like making him interested in sissy porn, you can't make him gay right away but with everything that's happened he will probably accept suddenly becoming curious about sissy porn since he's now willingly buying women's clothes.