Pure Pure Pero Pero Princess

At 42 years old, Toshio Kaname just got laid off after twenty years at the same company. No prospects, no direction, just wandering the streets feeling sorry for himself. Then a mysterious woman named Iris shows up and asks him to help save her kingdom. Normally that kind of thing sounds like a scam, but when you've got nothing left to lose, why not follow the beautiful stranger to a magical realm? Toshio gets transported to the Kingdom of Perahim, where a prophecy about the next ruler somehow involves him recovering two sacred relics. The setup is classic isekai, but the middle-aged protagonist angle gives it a different flavor — this isn't some overpowered teenager, it's a guy dealing with a midlife crisis who stumbles into a fantasy quest alongside Princess Iris. The OVA is based on a visual novel and produced by Ryuu M's, and it leans into its hentai genre without pretending otherwise, so know what you're getting into. The world-building around Perahim is more fleshed out than you'd expect, and the dynamic between a jaded salaryman and fantasy royalty has genuine charm to it. If you liked the isekai fish-out-of-water energy from something like Petite Princess Yucie's fantasy setting or the tonal whiplash of Magical Witch Punie-chan, this hits a similar vein but with decidedly more adult content. Worth a look if the premise clicks for you.