Joshiochi! 2-kai kara Onnanoko ga... Futtekita!?

An accidental incident leads to relationships with two women 

A Ménage à trois kind of relationship that includes 1 guy to 2 girls, where anything can go a usual romance of a threesome togetherness or to a break up where nobody gain anything, but in Joshiochi it was more like something that one would expect a harem guy to to to his harem .  

Short hentai episodes. Plot is dumb as hell but not too annoying to pay attention (who needs plot in hentai tho) Some catastrophic events force characters to live together thus making them develop closer relations 

Two girls with similar personalities and looks fight for MC by making hot stuff (Shorthair persistent Ui/Sunao vs Longhair shy Rin/Yuki). While Joshiochi is hentai, Okusama is balancing on ecchi borderline. 

The same plot where guy gets to bang 2 girls, though one has the 3rd girl who come around, both guys did a virgin.  

Both are slice-of-life comedy animes that focus on a group of girls. In Joshiochi, the girls play games with dares in order to win money, while in Asobi Asobase, the girls try to teach a foreign girl about Japanese culture and end up playing various traditional games. If you liked the dynamic between the characters in one anime, then you will most likely enjoy it in the other as well. 

1 guy to 2 girls ratio and with lots of fun among them. Except of course one has something oral involved while the other was just the usual.  

Both involve 1 lucky guy ending up in perverted situations and giving into temptation 

Both explore the relationship between the MC, who is a tenant, and the relationship he has with his landlady. Love polygons play a role in both series that help add to the plot and form a huge portion of the plot relative to the length of the series. 

Short hentai TV anime which are a mystery why they are being made in the first place and why MAL doesn't tag them as hentai. 

Both involve a lucky male protagonist experiencing incredibly unlikely sexual accidents around women.