A woman's perspective

That's it, you'll make him start being more conscious of women's fashion, since he's now buys women's clothes he should accept it. You'll make him want to learn more about how to cross-dress and that should lead him to sissy's all by it's self, but just in case it would be best to also make him enjoy how he looks in them, make him proud of how his arse looks in tight jeans and happy about his flat stomach. You need to make him think that since he's wearing women's clothes that having a womanly, or at least androgynous, body is a good thing. Lastly you'll make him start to unconsciously compare him self to other women instead of men. Hopefully that'll also affect him while watching porn and shift his sexual orientation without him noticing so he doesn't reject the hypnosis.

You go and find your brother and, "sleepy time", put him to sleep so you can get to work putting the changes in place. "From now on you'll not only like women's clothes because they fit you better, you'll also enjoy how they look, you'll want to make sure what your wearing looks good on you and you'll become more interested in learning what's in fashion to make sure that happens. You will also start enjoying the changes that are happening to your body because they help you look better in your new clothes which you now love. You'll be happy about how the form fitting clothes make your butt look and want to push more during your gym sessions to further enhance the changes, after all you can't have a mans body while you're wearing girls clothes so it's normal for you to try and fit your new wardrobe better. Finally you'll start to associate more with women, when you look at them instead of thinking how good they look in their clothes you will think about if those clothes would suit you too. When you look at their body's you'll not be thinking about how sexy they look, instead you'll compare your self to them and think about how you can become more like them. You'll compare your self to them and feel jealous when they look better than you and proud when you look better than them. No matter where or when you'll always consider things from a woman's perspective instead of from a mans without noticing that you're doing it." that should be enough to set him down the 'right' path. Before you wake him up again though there's something you want to search on his computer. You open up YouTube and type in a bunch of different make-up and fashion channels to make them show up in his recommended. You also go to google and search for some sissy/tg caption blogs that you found just for this so that when your brother starts getting curious they will hopefully appear in the auto fill. It's not a guarantee he looks at them yet but you do it just in case, at worst it'll help when you do the next, more **** changes once he accepts and get's used to these ones. With that you wake him up and quickly leave to let him explore his new found interests.

Brothers POV

You were just spending the morning lounging around but it seemed to fly by, one moment you're getting out the shower and the next it's already time for you to go to the gym. Once you get there you change into your now normal exercise gear which consists of a pair of women's shorts which is a new one you bough during your shopping trip and a tee-shirt you also bought, you were already wearing one of your sports bra's since you knew you were coming to the gym. You thought that you would feel more self conscious about wearing this gear for the first time but for some reason it all felt natural, after all it all just fit you so much better so why wouldn't you wear what's better for your body? Who cares if it's not 'men's' clothes, these are what feel comfortable so you'll just have to wear them until your body is fixed, so there is no need to feel embarrassed about it. You head out towards the gym equipment and notice a woman stretching on the yoga mats you always warm up with as your heading over. You can't help but think about how pretty she looks, 'I wonder if my butt looks as good as hers in these shorts', you don't know where the thought came from but you stat comparing your self to her. You sneak a look into one of the mirrors coving the gym walls to check out your arse, it's defiantly fuller than the start of summer but you're a little disappointed that the woman over there has a fuller bum than you do. Wait why do you want to have a womanly ass? you're only going to be wearing this stuff temporarily so why does it matter if you look good in these shorts, I guess it's better to look good in them than bad, right?. You shake these thoughts from your mind and try to forget about them but for the rest of your warm up you can't help looking back to the mirrors and at your ass. You decide to go all out for the rest of your session.

You get home completely exhausted from your work out, you don't really know why but you were like a man possessed during this session and kept pushing past when you would normally stop. As you walk into the kitchen you can see your sister has already made lunch and it's waiting for you on the bench. You wolf it all down and head straight to your room to rest and watch some Netflix or YouTube. You open up YouTube and click on something from one of the channels your subscribed to but you don't really pay much attention and instead just enjoy sitting down for a moment and relax. While you stare absentmindedly at the screen you look through the recommended video's to see if anything catches your eye when you notice something you wouldn't normally see. The title is 'how to put together an outfit 101' and you can tell from the thumbnail that it's about women's outfits not men's, you almost keep scrolling and ignore the video but then you think to your self about how all your clothes are girl's clothes right now so wouldn't it be better to learn how to match them? After all you don't want to walk around wearing something weird so it'd probably be best to learn at least a little about how to pick out an outfit from your new clothes. Surprisingly you found the video really interesting, you followed the whole thing paying close attention to all the tips it gave, even though some of the outfits involved skirts and dresses which you wouldn't be wearing you still found it fun to learn about how to match them with a whole outfit. You never knew it could be so fun to learn about fashion but couldn't stop from watching more. After about 40 minutes or so of watching fashion videos you notice a makeup tutorial in the recommended, you shrug and think why not? after all the fashion videos were more fun that you expected. Again you become enthralled with learning all you can about how to apply makeup and how to pick out what to use and when, you only watch videos about some of the basics but it's already so much new things you having to take in. It's only half way through the second makeup tutorial when you think to your self that maybe it's weird for a guy to be watching all this after all you're not a crossdresser you're just stuck wearing women's clothes for a while. But just as you think that you find your self typing 'crossdressing tips' into YouTube's search bar, for some reason the word crossdresser made you really curious to find out how they do it and what differences there is from the videos you just watched. You end up spending another hour going between all 3 types of videos learning all you can, completely entranced with all the videos.

You decide to stop for now although you subscribe to a few of the channels for later to learn more despite feeling a bit embarrassed about how obsessed you've become now that you think about it. The best way you can think to clear your mind and help you calm down from the fashion frenzy is obviously to masturbate so you instead load up porn hub and search for something to watch, "maybe I should keep up the theme and watch some crossdresser porn" you joke to you self but just out on something from your favourite category, red head. The video starts up with the classic intro then with a beautiful red headed woman sitting on a couch in a pair of daisy dukes and a tank top. 'That's a cute outfit' you think to your self 'and that makeup really suits her' you can't help looking at the woman and using all that you've learned to asses what she's wearing. Finally you start to play with your hair, you haven't got it cut in about 2 months now so it's getting pretty long, 'I wonder what I should do with it', you briefly imagine your self with the same hair style and colour as the actress in the porno but push that thought to the back of your mind and try to pretend you didn't enjoy how it looked. All this time the woman has been playing with her self but you haven't been able to get into it at all, the video you chose turned out to be a solo play video so you think about looking for something else to try. You give it a bit longer and try to watch without thinking about her clothes and makeup and imagine being there and playing with the woman your self, touching her breasts, kissing her and of course fucking her but still nothing. Then slowly, without you even realising it, you move one hand to your chest and start copying how the porn star is playing with hers. A spark runs through your whole body and a slight moan escapes your lips. You start rubbing the tip of your dick like she's rubbing her clit, you keep copying the woman on screen and you get closer and closer to cumming. Then she starts to finger her self, just like her your hand starts to drift lower looking for a hole that isn't there, so it keeps going down until it touches your ass. You almost jolt upright as you realise what you were about to do and stare at your fingers covered in your own precum from rubbing the tip of your penis just inches away from your but hole. You think about stopping altogether at this point thinking you've killed the mood but you're still incredibly turned on. Looking back to the video you watch the woman moan in ecstasy as she fingers her self and can't help but wonder if it'd feel that good to finger your self as well. After all you know that men had a g-spot in their ass from the prostate. You tentatively circle a finger around your hole while still playing with your breasts and start to moan and sigh in pleasure again. Maybe just a little wont hurt?