Bakunyuu Oyako

Because Resort Boin is a sequel that changes settings, add new characters, new kinks, between other things, it has less to do with the first scenario of simply a sensei and his hot young students, but there's still some of that there, since the two students are still there and they still call him sensei with passion in the scenes, and that's exactly what Bakunyuu Oyako is about, well there's also the milf, but guess what, one of the new characters in Resort Boin is in the more mature ratio and has a similar type of long hair and colour. 

Both have busty milfs, emphasis on busty, you'll definitely like it if you're into that, Bakunyuu Oyako also has the busty daughter of the milf, while Okusama Wa Moto Yariman is exactly three mothers participating in the action, but no one else, but the busty milf is the part of interest of both of these hentais. 

You like stories where the protagonist gets it with both the hot chick and her mom? Well I've got two examples of that here, except that Hitozuma Life is completely focused on the milf (and some gyaru stuff, I guess), her daughter is there and she's definitely fine, but she doesn't get any scenes, Bakunyuu Oyako covers completely both girls, but both have that interest in the milf aspect and big kaboompos. 

If you love the idea of banging a girl AND her mother, then look no more here's two OVAs perfect for the job, ok Koiito Kinenbi also has little sister, but that just makes it better, plus there's other short stories, which are by no means bad and are still pretty vanilla, besides both have a fixation on boobs (specially Bakunyuu Oyako), so enjoy to your heart's content. 

Only the third episode of Arbeit Shiyo!! Has a similar plot to Bakunyuu Oyako, the one of the hot private teacher doing some more particular teaching with the student, except that the roles are reversed and Bakunyuu Oyako has the student being a hot teenager, besides both have that same style of animation and feel proper from hentai from mid 2000's (and kinda cheap). 

Besides the fact that the roles are inversed, the plot of both involves private teachers and their students getting dirty while doing the lesson, Bakunyuu Oyako has a male teacher with a busty student (plus her equally voluptuous mother) and Kateikyoushi No Oneesan has a variety of sexy oneesans with a lucky guy, both are also hentai from mid 2000's (but Kateikyoushi has better animation and design). 

Both animes about huge chested girls. 

There's the same of plot of a lucky teacher being intimate with his students or just one student in the case of Bakunyuu Oyako, which also features the busty mother of the girl, in Boin there's also a sensei at play, she's not a milf, at least I don't think so, but she's definitely in the more mature part as the busty mom, and finally both are hentai from the same time, mid 2000's where animation for hentai didn't have as much budget as older OVAs, nor had the technology to conceal the lack of frames, so there's the same energy from both.