Wolf Girl
Initially watched this bc the cover looked absurd. It was very ecchi.
It answers the question of "what would school life look like for a girl that was raised as a wolf" that just happens to have her pussy out sometimes, rather than being an outright porno. The people that have to help her barely even feel like they want to do it, so I'm not entirely sure why this was made.
Not a whole lot to it besides that but is crazy to watch high especially for scenes like this:

There's kinda a lot of stuff from this era that seems to be absurd just because it can be. Maybe a byproduct of attempted innovation from an emerging market?
If for some reason you wanted to watch this u can do so here

Ok you've prolly seen screenshots from this game but never actually played it. Home to iconic lines such as:

The Sex Kitten series started in 2004 and as fas as I can tell is still ongoing. From some of the same devs as EVA4 sim date "kills you with a large brick" rpg, comes over 20 installments of point-n-click trivia hentai fetch-quest gameplay

Most of the games revolve around you and Slutty McSlut getting into some kind of mischief (mostly her) and having to get out of it usually by collecting porn from strangers.

If you wanna get right into some good short examples of the gameplay I'd start with Sex Kitten Prison Break or School Girl Sim 1. If you wanna get the full story I'd start with Sex Kitten Sim-Date. And if you wanna start with (in my personal opinion) the magnum opus of the genre, I'd skip to Sex Kitten RPG2: MindFuck.

RPG2 combines multiple gameplay styles such as first person point-n-click and top down rpg movement sending you on probably the longest fetch-quest of the series. You'll meet many different characters while trying to navigate around the massive 3-world map without dying from answering a trivia question wrong

I've still yet to finish it due to the insane length and lack of saves but there's no way I'm gonna let "Sex Kitten RPG2" get on my started-but-didn't-finish games list.
While I'm here thought I'd mention Kramer Hentai Adventure as well if you're looking for more games like this

While this style was probably still inspired by Megrim Haruyo, I had the idea of a living chandelier with the same purposes of display. Several ideas came to me while drawing it, such as the implanted spikes to keep the hair out of the face appearing like a crown, and the top ring almost resembling a constructed halo. Not terribly pleased with the watercolor but it's been a very long time and it's also the wrong kind of paper lole.

Kite (1998)
This is a strange one. I had only heard of it because I watched the spiritual sucessor which I only found while looking for abnormally well-developed or beautiful hentai from the 80s and 90s. Despite this it seems to have been good enough to inspire things such as Psycho-Pass, Kill Bill, and even getting a live action remake with Samuel L. Jackson.
Off the bat I should say that this is porn, or at least published by a porn studio and has stuff in it that could be considered porn. It's better summed up as a weird action drama amalgamation with insane 90s styling direction and brash adult themes. TLDR there's a lot of factors that take precedence over the pornographic part, even though it's still very present

The protagonist, Sawa, secretly works for a cop, Akai, performing assassinations that Akai later investigates the crime scene of in order to hide eveidence. Sawa's motivated because her parents were murdered when she was very young, and Akai had taken her under his wing while she trains to ultimately get back at the person that killed her parents. It's known that Akai was the one that murdered them all along, and he'd been sexually abusing Sawa as part of the deal.
This is a pretty good premise for what it is, especially only being an hour long. I do need to say that the sexual abuse is fully animated, though all but the last scene of which can prolly be skipped without missing any plot, as long as you know that it's there. And it pays off (spoilers) when she fuckin shoots him directly in the dick near the end.

The action scenes are extremely well animated especially for something published under a hentai studio, was mildly disappointed to see that their lineup is mostly only generic hentai slop otherwise. The quality looks like it mainly comes with the director (Yasuomi Umetsu), and they've done other work with things like robot carnival.
Getting mildly off topic though, Sawa uses a handgun with exploding bullets, which results in some super sick close combat bloody action scenes. Minor spoilers but my favorite one is when they fall out of a building while fighting, and they land on a car, which crashes through a bridge, which crashes to the ground, which crashes through the ground to a subgarage. It was so over the top out of the blue and it literally left my mouth agape.

It probably helps that it's so short but the character design is also really good. Even their targets and side characters have rather unique designs. I also haven't noticed it mentioned anywhere else but one of her outfits seems to've been inspired by evangelion. Also there's a guy who's name is pronounced "Kanye" and he looks like this.
Lastly I do gotta say the art is general is beautiful. I would go as far to say that it's a staple of 90s animation.

While I wouldn't reccomend this to everyone, if any of the above intrigued you I'd highly suggest watching it. I think(?) there's a cut that removes a lot of the sex scenes too

Inspired by Megrim Haruyo. While not rearly as good, it was fun to experiment with an aliased multi-layer pixel technique