The Complete Living Together

A new roommate brings Brandon's hobby of playing with Taylor's underwear when she's at work to a screeching halt. Now, she's got big plans for him and Brandon soon finds himself at the mercy of his two beautiful roommates. Morgan wants to punish him for violating their privacy and Taylor wants to help her friend man up and do something with his life. Unfortunately for Brandon, both women have decided that feminization is the perfect way to achieve these goals. 

That's the basic elevator pitch.  Living Together is a series that can be cruel and humiliating at times, but in the end there is a sense that people do care about each other and the series has a sort of sweetness to it. If you like your feminization both humiliating and with a happy ending, I think it's one you'll want to check out.