I know there are many cis people who struggles with fitting into the stereo-typically gender roles too, but I feel it's a bit difference in some ways when you're transgender. It's not only about fitting into the society, but also about passing. Have you ever done things difference than what you wanted to because of passing, transgender stereotypes, fitting etc or didn't you care about what the society thought about you? I'm just curious.

There are many transgender stereotypes, but the gender role thing is one of them, something that's boring... -_-
It's like some people in the society expect trans men to be masculine and trans women to be feminine since they were young. Not only the playing with toys, pink vs blue choice etc, but also about hair and clothes. I dislikes when we can get labeled as "Not trans enough" etc. when we doesn't follow the gender stereotypes.

Cis people doesn't necessary being seen as lesser cis if they breaks the gender roles (Talking from my own experiences), but transgender people can be seen as not trans enough. I'm not super feminine or super masculine, but I've some feminine sides. It can be both interests and mannerism. I hasn't tried to get rid of them and I'm not out yet. But I thinks it's sad with these stereotypes including this can affect the passing. I cut my hair short because I wanted to try it and I likes having short hair. But I finds long hair awesome too, it looks nice. But it's harder to pass with long hair, so I've been a bit unsure if I should go for it or wait to T.

I hope I can hear some of your problems related to gender roles, stereotypes and passing.

I can't speak about your question on trying to conform to the gender I've transitioned to, because I haven't yet begun any transition process.

The gender role thing is something that caused me to begin questioning my gender in the first place.  As an AMAB, I've more recently realized that the male behavioral and appearance expectations are just too restrictive for me.  I've spent my whole life trying to fit in, not always quite successfully.  I even remember my dad asking me, on more than one occasion, if I was gay.  I always knew I liked girls, so my response was always that I was certain I was not gay.  And since I didn't know that there was this whole other gender spectrum in addition to the sexuality thing, I left it at that, and slowly learned that I ought to act more "male" or face others' disapprobations.

As far as appearances go, I've found out, thanks to slumber party events at my dorm, that I rather enjoy having painted fingernails.  I haven't yet had the privacy to try much more than this, as far as clothing and makeup are concerned, but I've enjoyed the yoga pants I purchased online.

Unfortunately for me, I'm quite self-conscious about what others think of me, and as such I have not the necessary boldness and nerve to wear anything other than stereotypically male garb (and occasionally some stuff that is a bit more androgynous, such as skinnier jeans).

However, my interests are quite heavy on the stereotypically male side of things: physics, computer science, video games, sports.

I'm guessing the cis people who break stereotypical gender roles are often classified by passersby as gay/lesbian, but I'm not sure about that.  I would also guess that one reason that cis people expect trans people to pass is because they're not yet comfortable seeing what appears to be a man dressed like a woman or a woman dressed like a man.

I hope that answers a bit of what you asked; I feel like I rambled and bounced around a bit

I agree with Popa. It is society that "wants" us to be in a certain gender classification. Since man first stood up it has been all about maintaining the family unit. This is reinforced in societies of every nationality. To society that means a man and a woman who raise kids to continue the human race. You can see it perpetuated in religion, country laws the tax code and by the parents. A reward and punishment system is set up to maintain things. Strict gender roles are also a part of this system. Anyone outside of the norm is also put in a strict category - gay. To cis people it is that simple. They don't really care about self expression, as it relates to sexuality, and to them no other gender category is needed. That is why people can be viewed as not cis enough or not gay enough. A transgender person that can pass as the gender they choose (we don't choose to be transgendered but cis people think we do), still appears to fit into the system as they appear to be one sex or the other. It is a real problem for this system when someone does not pass so they are ridiculed or looked at as "strange". Part of being transgendered is to "throw off" all the crap that has been drilled into us by the system (another brick in the wall!) since we were infants and just be ourselves. In fact to be truly happy that is what we have to do. Just my view and hope it helps.

Yeah slightly. I'd love to have long hair but i don't think it'll suit me plus I like how 'tough' and masculine my short hair looks. I guess I use the appearance to act as a shield; so in case I act 'too fem' or someone suspects I'm trans (ridiculous i know) then hopefully me looking macho will deter them. I want to wear fem clothes but there's always that fear of what others will think because if you like a man doing that again you're going to be ridiculed or thought of as weak. Which makes no sense because women are tough as hell to have to go through all the misogynistic and biased stuff they'll face in life. I don't follow the pages on the internet anymore on 'how to pass'. Yes some of the information can make you feel more confident but most of it just makes you feel worse because you can't get the clothes you feel you need to be seen as you are; even if you may not like that particular clothing choice. It's ridiculous; I try to say to every ftm on here who posts asking for tips on passing that's it's much more important to look how you want to look. I feel constrained by the binary even though I'm not a part of it and restrained by how others see me. I may look like a guy but that doesn't make me one. I don't have to be the stereotypical thin androgyny to be considered as a 'real' nb person.

Sebby, you wrote a very lucid post and I totally agree with you.

If my experience can help, I am socially out to friends and teammates and have a masculine wardrobe (mostly man clothes, the items from the F department are extremely masculine from that point of view and fits me better size-wise).

I too have some "deemed feminine" interests, as you can probably see in my avatar I have a personality that includes a lot of refined interests, and I like to have a bit of a cute-in-a-serious-way side too. It might sounds a lot, but to give you a fantasy reference point I would like to be a cross between a Native American warrior and a Japanese Heian noblemen, or a cross between a Chinese administrator and a Xianbei warrior. Maybe an oxymoron, but that's me.

So, long hair are definitely a thing. I'm coping with mourning mine by showering it with an algae conditioner and focusing my thoughts on their growth. I love my silky dark ash blonde hair and my singing voice, discerning tea varieties, and I totally adore refined textiles like the Edo Komon and I'm interested in weaving and dye techniques. And I'm a dancer.
That said, I'm also a martial artist, a lacrosse player, and one of the most sober, minimalist and trekking-in-the-woods type of people around. I'm just me. I also believe that my mind and my body are one and the same and I read myself as a men with a little different biological starting point. For your reference, the SAGE gender test gave me an FtM result with male socialisation and the other areas androgynes.

I like to think that worrying about passing is having very normal masculinity issues and I shrug it off, not always easy but my identity don't revolve around people clapping their hands in recognition of me, and I feel better this way.

I also know for a fact that this strict binary is a very recent and Western thing, it has never been this way or this way everywhere, so I know I'm doing something more natural and more human than what the enforcers of rigid binary does.

I have thought about long hair just to "pass"... but decided against it. Like short hair better at the moment (even for most girls*), and what's the point in replacing stereotypes you don't like with other stereotypes you don't like