Yes, but of course, this was late Victorian/early Edwardian era, when many children were dressed fairly feminely but I have read that she went a little over the top. She was a bit of a weird one - talented opera singer but too afraid of the lights to go on stage. She was also very "pure" and "proper" and expected her children to be as well. Oak Park, the town he grew up in was a fairly prudish religious town - but it was a different world in 1899 when Hemingway was born.
Doubt it, it is said he greatly resented it and that was one of the primary things that rove him away. Hemingway definitely had a reputation for getting into women's knickers later in life, but not in the way you mean.
There is this persistent rumour that he developed a taste for the J. Edgar Hoover lifestyle though. Probably just scandalmongering from those who thought he was an overrated hack.