I've been on Google for hours now searching for everything within the realms of male crossdressing, victorian era and civil war as well as everything in between it seems and I'm still not getting a very good idea of what I'm looking for
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In the civil war era, hormones, injections and so on would be out. My best guess at what he might try -- if he could find a willing doctor or animal vet, would be a simple castration. Just the removal of the testicles - removal of the penis is risky because if the urethral opening heals incorrectly, he could die. Also, back then, there wouldn't be much in the way of useful anesthesic or antibiotics (or the concept of germ theory, for that matter). Castration is a: relatively minor surgury, in terms of trauma to the body and b: something most everyone in the era would be familar with as a way to make something or someone less male.
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As for permanent changes from the corset, those would be most effective if it was before he finished growing and his bones set. Over time a constantly tightened corset could compress and shift his ribs, and change the curve of the spine. When he stopped growing and his skeleton shifted from the growth plates being active to closing as an adult those skeletal changes would be fairly lifelong modifications. It's like children needing back braces for scoliosis or cultures that do body modifications like neck stretching or other long term bindings during youth.
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He started when he was 16, which I think is still early enough. How would you circumvent the issue of broad shoulders? Not that he has really broad shoulders, but do you know if there's anything he could do to narrow that part of his body?
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There really isn't anything that narrows that body to this day.
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The MC's father works for a man with ties to the military - who was wealthy enough to get his sons out of it, but sent both of them to war regardless - so there was some pressure. And they lived in Savannah at the start of the Civil War so there was also that added pressure.
The background was that his son had run off to enlist, despite being too young (because, yes, that did happen fairly frequently), and for several months he kept his son sequestered in their home. And later re-introduced his "niece" who had come to live with him after her father went to serve the army. The truth in that is that the MC's father does have a brother who was a prominent military man, but his daughter actually went to stay with distant relatives in the North. It was a tricky story, but he didn't expect to have to follow it for long. Then, of course, his son decided he wasn't going to shift back to being male after the war was over either way ( ... )
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http://coilhouse.net/2008/03/mr-pearl-on-corsetry-technology-and-posession/
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and 1860's a "real lady" had to have pale, dainty hands [I remember Scarlett's sisters crying about damaging theirs because of cotton-picking in 'Gone with the Wind'] and since men's hands are usually broader and bigger, maybe he could wear gloves too.
as for shoulders, it seems like shawls were in-style then, so maybe these? capes weren't practical with hoop dresses.
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Pale, check. He's very thin/lean so he has never long/thin fingers as well. But I always work in gloves regardless because I love them. And the shoulder-length shawls that I think you're talking about I've always heard referred to as capes, but that's just a semantic thing so yes! I hadn't thought about the chokers/collars though so thank you for that! :D
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