Im lost on the title of 2 games Ive played years ago

Theres 2 games on my mind I want to see how much has changed, and its been years. I forget the names of them but I remember them vividly. Both games are in the style of games like Corrupted Kingdom and Heroes Harem Guild.

The first game is where you play as a young black haired boy living with a blue haired milf figure and a younger female. You can choose what they are in relation to you (mom, stepmom, babysitter, step sister, best friend, etc.). There are a bunch of other females in the town, one of them is a white haired jogger in the park, theres a girl that falls for you and her mother gets attached later on, a shy girl playing chess in the park, and a female in a club you can pay for services. Thats all I remember for that game

The second one is where you play as a blonde male that goes to school with a ton of females from other anime, and the 3 main girls you can bond with is Android 18, who is your teacher, Tsu from MHA as the swim team captain, and Raven, who you can make sit in the bathroom to be used for money.

Can anyone help me out?