Otto no chinpo ga hairanai - Season 1

Kumiko is a shy and nervous college freshman. She moves into run-down student accommodation having shaking off the constant browbeating from her overbearing mother. There she quickly meets sophomore student Kenichi when he strolls into her room and makes himself at home. They go on a date of sorts, and when it comes to clothes off time they find that, physically at least, they aren't connecting. It's not for lack of trying, but it just won't go in.