Earn Your Freedom is a horror story.
Don't get me wrong, it's also solid porn, and it does very well in what it's supposed to do: be sexy, interesting and not boring to play through. But to me, Earn Your Freedom's most shining accomplishment is the sheer horror of the plotline when it's assessed logically and removed from a sexual context. A barely 18-year-old boy loses his father and is forced into a repeated onslaught of sexual slavery, has his body modified (experimentally and illegally) against his will, is threatened with sexual torture and repeatedly is gaslit/brainwashed by Erica in "hypnosis" sessions. This system is protected by the police and even the characters he trusts (such as Craig) are in on it, and it's implied at least some branches of government are too. Horror is everywhere in Earn Your Freedom to the point where I found it impossible to overlook, but it hasn't made the player.
Yep, bear with me, I know this is a weird review. And I haven't seen anyone else mention the horror aspects of the game, so this interpretation seems to be specific to you. It's meant to be (and is often perceived as) a regular, non-scary porn game, but I can't stop looking at it through this lens and feel the need to share it here.
Okay. Phew. Now that f95zone user fakeplastictrees's weird opinion is out of the way, let's talk about gameplay mechanics. The art style is very good, the cast of characters is varied (in body type, age and sexual fetishes), and the scenes are often exciting and fun. As others pointed out, the game is a little "grindy" at times, but honestly, there's a skip function to avoid replaying the same scenes over and over. If you're looking for an interesting take on sissy porn, I definitely recommend playing this - who knows, maybe you'll learn something about yourself