Ok, name change for this post only.
I guess the first time I remember getting an insight into what it might 'feel like' to be a woman was when, aged 10+, it became my job to 'help' my mum with the weekly house clean. It was my job to hoover the whole house from top to bottom - my brothers would often be sitting on the sofa watching TV, and as I got close to them, they'd lift their legs up so I could hoover the carpet thoroughly underneath where they were sat.
A few years later, I got more clues when I was targeted for sexual abuse by a (male) family member - I don't recall him checking first whether I 'felt' like a girl/young woman, he just somehow knew that I was the appropriate child to target out of 4 siblings, the other 3 of whom were born male.
In my 20s, I used to get my haircut regularly at my local barbers, never wore dresses, make-up or heels, and yet somehow I was still clocked as sufficiently 'woman' to be subjected to a brutal stranger rape - I'm pretty sure I was 'feeling like a woman' when I had my legs in stirrups after that, as I was fitted with an emergency coil in a bid to ensure I didn't have to deal with a pregnancy. I felt even more like a woman when I was grilled on the stand in court about every intimate aspect of my life by a (male) barrister in a gruelling effort to discredit me & my testimony. It worked as well - the jury exonerated him, following which my (male) rapist was told by the (male) judge that he could leave the court with his head held high.
Within my marriage, I strove to try & create a partnership of equals, without realising for many years that my then husband's many 'mistakes' that somehow left me more or less constantly 1-down, and him very much 1-up, formed a very distinct pattern; I was helped to understand that pattern when I was referred by my Health Visitor to the Freedom Programme, where I sat weekly with a group of people - all also biological women - who'd all had strikingly similar experiences. I'm quite certain that our commonality wasn't due to us 'feeling like women', but because of our biological reality as women, because of the socialisation we'd been subjected to on account of that biological reality.
I could go on - I could talk about the (male) gynacologist who never once looked at my face as he talked at me while performing a painful internal examination - although he did have sufficient decency to look at my then husband when he spoke to him, funnily enough.
Rather conversely, when I trained as a carpenter at a women-only training centre, I don't think I felt like a woman or a man - my experience was that I was just trying to live my best life as me. But when I went to do my site-work placement, despite the fact that I had the same level of skills as the male trainees also on placement from the local college, I was definitely singled out for abuse as a woman - the daily barrage of crude comments about my body, the jokes made about me as a carpenter showing that I was automatically devalued by almost everyone else (all male) just because of my biologically embodied reality, rather than anything to do with my skills or ability. The daily abuse was too much to take & I left, meaning I never actually got the qualification I had, until that point, worked so hard to achieve.
So to me, I really can't get a grip on any idea of what 'feeling like' a woman is that's in any way independent of, or separable from, my experiences of having actually been socialised & treated 'as a woman' for a little over 5 decades. I've never found any commonality I share with other women based on feelings, but I have, over the years, found an enormous degree of commonality based on shared experiences of the embodied biological reality of having been born, raised, socialised and treated by others as 'woman'...