
If you're looking for anime similar to The 26-Year-Old Girl Had Her First Time Taken by Her Playboy Boss, you might like these titles.
Minori, an office worker and her boss Hadano, are constantly arguing with each other. One night, after a company drinking party, Minori and Hatano are having their usual argument, when Minori realizes that she has missed the last train. They decide to spend the night at a nearby capsule hotel, but an incident forces them to share the same unit.
A woman reunites with her first love at a class reunion. She discovers that Kujou has taken over his family's temple as a priest. The woman thought that priests did not have romantic relationships, but a passion ignites between the two. She wonders if what she and the priest do is really right.
Kouya Asumi is a fourth-year college student who works as a housekeeper for the single father Keiichi Naruse, and a relationship develops between the two.
Reserved Shizuka attends a local mixer party but has trouble adjusting to the atmosphere. A beautiful older female college student named Ryou starts talking to her, and the pair hit it off. Shizuka goes to spend the night at Ryou's place. However, Ryou unexpectedly kisses Shizuka and pushes her down. Shizuka thinks the beautiful woman is a lesbian but soon discovers that Ryou is actually a man dressed as a woman.
Hana Natori is an earnest, good-natured 25-year-old woman whose cousin refuses to go to high school. Hana takes her cousin's place and attends the high school. On her first day, though, Hana's ruse is discovered by her former high school classmate Okito Kanie — who happens to be the high school's world history teacher.
Follows Tsumugi, a female college student who carries trauma from an aggressive man in her past. She meets Kaname at a mixer she requested specifically for unaggressive "herbivore"-type men. She and Kaname hit it off, and Kaname resembles Tsumugi's older brother a little bit, so she relaxes her guard around him. Kaname, however, feigns to be a "herbivore"-type man, but is in reality an aggressive "carnivore"-type man, and he can change his demeanor in an instant.
Late-blooming teacher Nana Saigawa goes to a matchmaker appointment only to find herself paired with a problem child student named Souji Kuga.
22-year-old Hazuki lives a boring life in an apartment filled with plants, but secretly he couldn't care less about the vegetation, for the highlight of the young man's day is buying the items from cheery Rokka, a widow who runs the flower shop nearby. So that he can spend more time with her, Hazuki eagerly accepts a job working part-time at the shop, but after months of working with his crush, the man can't seem to muster the courage to confess his feelings. And it's not just his abrasive personality getting in the way of his ideal relationship - the ghost of Rokka's dead husband haunts the shop and is determined to keep all potential suitors away from his wife. Despite this unexpected obstacle, Hazuki continues his attempt to woo the older woman and free her from the ghost of her past.
Mio Sudou is an office lady who has not had a boyfriend in five years and has forgotten what it is like to be in love. Shuji Majima is an overseas insurance consultant who has not had a girlfriend in seven years despite being highly eligible. Mio meets Shuji at a matchmaking party, but finds him revolting as he states, "I'm not into women." However, a provocative comment by Mio takes things in an unexpected direction.