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you do have to have an interest in clothes tho

STOP BEING A COWARD AND JUST DO IT
MAKE YOUR DREAMS COME TRUE
PUT ON A SKIRT AND THIGH HIGHS AND TAKE PICTURES OF IT TO SEND TO ALL YOUR FRIENDS WHILE ASKING THEM
"d-does it look good on me?" DESPITE KNOWING THAT YOU KNOW IT DOES
BAITING FOR COMPLIMENTS IS CUTE

STOP BEING A COWARD AND JUST DO IT
MAKE YOUR DREAMS COME TRUE

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you sound like those motivation coaches

@Tristan__ Yes, I agree, but if you have no interest in clothes then attempting to look at clothes will essentially be worthless
That's why I always say to look at some kind of specific outfit they like the look of on someone else, figure out what the pieces of the outfit are and buy it themselves

If you buy girl clothes for yourself and you've never done it before, it's going to look different and that's not a bad thing, it's just a learning experience on what to buy to suit your body. If you continue to buy the same kind of clothes and complain that it doesn't look good on you I'm going to hit you with a soap bar stuffed into a sock

THAT'S HOW IT IS FOR EVERYONE, NOT JUST YOU

FIGURE OUT WHAT CLOTHES THAT LOOK GOOD ON YOU, NOT THE DUMB MODEL YOU'RE LOOKING AT

YES LOOKING ATTRACTIVE WILL MAKE ANY OUTFIT LOOK GOOD
IT DOESN'T MEAN THAT IT'S A LOST CAUSE IF YOU DON'T LOOK LIKE A SUPER MODEL
THERE'S ALWAYS CLOTHES THAT EXIST THAT LOOK GOOD ON YOU

FIGURE OUT WHAT CLOTHES THAT LOOK GOOD ON YOU, NOT THE DUMB MODEL

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I worry for the person who does that and I hope they get themselves a mirror

it also makes me feel like a gigantic piece of shit for not being more into dressing up like a girl myself
I get so little enjoyment from the act itself that the only thing that the only part of crossdressing I'm interested is helping out people who are starting off themselves

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🤔 what if sono bisque doll, but instead of cosplay the mc helps people with crossdressing

isn't that basically the plot of that one manga that got localized into English and instead of being a crossdresser they made them trans and there was big drama because the localizers said they did tons of research and the author and publisher told them they were wrong

although, you know, I don't like the manga for other reasons

it's so unsatisfying when characters end up looking like cosplay-tier crossdressers the very first time they try and have to put literally no effort into doing it

WHERE'S MY PROGRESSION ARC

one of my favorite plot lines related to crossdressing is when have a pair of childhood friends, with one being generally bigger or stronger than the other and over all of the protective interactions, the smaller one falls for the bigger one

and because the bigger one has only ever shown an interest in other girls, the smaller one thinks that they have to crossdress to appeal to them instead

even better if their crossdressing "hobby" is found out and the bigger one is supportive while at the same time trying to deal with their own newfound but not quite obvious feelings about how their friend looks

all while the smaller one gets mentally annihilated by any compliments they receive which fuels them to go even deeper down the crossdressing rabbit hole to appeal to their friend

that extreme frustration towards being born the same sex as the person you like but finding a way to make it work out is imo a very relatable concept, and trying to navigate a solution to make things work even in such extreme circumstances is something that gives people hope

I scanlated something that sort of conveys that
https://mangadex.org/title/30c87132-1962-45e9-b367-a243164efb82

There are pretty rare instances where the taller person in a relationship ends up being the crossdresser, it's hard to think of many instances off the top of my head. The only two I can think of are:

https://mangadex.org/title/bf24e900-128f-4c9e-bb4f-de00530f431d
https://mangadex.org/title/003b5f82-1f80-4775-bef2-d5c5bc81f3c9

Nise x Koi Boyfriend is bit of a shorter story, but it sold me on the idea of having a stereotypical, cool, tall male character being fully capable of crossdressing as an extremely over the top lolita gf. Lolita clothing not being as form-fitting as other styles of fashion lends itself quite well to crossdressing where you try not to accentuate your masculine features that much.

"My Ex's Younger Brother" actually has three volumes out at this point and is at the top of my "white whale" list of series I'm waiting on a translation for. The art style is a bit of a turn off for most groups unfortunately. The series does a great job at developing character motivation and their expression of emotions in different situations. The fact that the taller one is the crossdresser is just a cherry on top.

when i cant sleep i went to read ply post and then dream about being straight while being cute. i guess a one piece dress is a good starter. ill try to look around.

Fr

I don't just want to read crossdressing stories that are about magically looking extremely feminine either. I enjoy when characters look relatively the same before and after. It's not like dressing up and being complimented will really fix any self-confidence issues either. Take this chapter from Crossdressing Boys of the Otaku Circle for example. It's really common to find yourself cute in the moment of things but to still later on think that you don't really look that good at all.