It's super funny how trans-coded Sam and Max are in the telltale games. Max is the more obvious one since there's men, women, and max symbols on the toilets in the bathrooms, but Sam as his own that are more subtle but stronger in my opinion.
In no particular order:
He has a stated fear of public bathrooms, in hit and run he goes behind a screen to put on a bungee jumping harness and helmet, he had a voice coach and a therapist, he describes his family reunions as awkward, says he feels jealous of other men's stronger jaw bones, he scolds Max for asking if Bosco was transformed into a girl cow, he's apparently incredibly sweaty with a strong smell, and his clones were described as "Zaftig" which is another way of saying voluptuous or womanly, which Sam didn't like. Also went to stewardess school???
Anyways. To me, this indicates that Sam is taking testosterone, as that causes excess sweating and new smells as second puberty occurs. But I don't think he's very consistent with it, he doesn't get the same results from exercise and his diet as Max does, and while it could just be max is max (and supposedly uses protein powder) low testosterone can cause weight gain and reduce muscle.
Not to mention, the neighbourhood they live in is supposedly 3 to 1 ratio of men to women, which is just meta commentary on their lack of introducing female characters. But including featherly as a rooster who can lay eggs, this indicates, if not new York itself, then their neighbourhood is known for having a lot of ftm transitions, which is funny to me. They accidentally coded the entire neighbourhood as transmasc. Though, considering most the neighbourhood is robots, this shouldn't be too surprising.