Myscra
The unstructured exploration with little direction is probably what makes it seem most old-school. The second biggest thing would be the style of grinding, though it kind of ties in with the former in some ways.
There are several ways to overcome either of these problems, let's look at some of the different methods developers have reevaluated exploration in modern games.
It has its own problems, but
Flirty F tackles arbitrary exploratory events by just letting the player skip the guesswork. The player
can still explore the game world and try to chance their way across the right events at right time; but the game also gives the option for every character's sequence where the player can jump to the next location required to progress with that character.
The most common way of protecting the player from their own urge to explore the entire world and waste time doing nothing is by gating off areas that only contain events the player doesn't qualify for. This is mostly used in RPGM games examples of which escape me at this exact moment.
Another method is reigning back in scope the number of locations available to the player. You see some of this in games like
SexNote (unsure if still the case, played a very old build),
Devilish Business, and one that does it particularly dramatically is
Last Hope.
There are other avenues for the exploration, but let's take a look at the grinding aspect. For this we're going to take a trip to a genre adjacent to this one: trainer games.
There are a couple types of progression in trainer games. This is a little bit of a stretch to apply to strictly text games as the reason it's done is to make more content out of limited art assets, but significant variant events in progressive order are a great resource.
If you look at games like
Witch Trainer, you have progression in the same category of event. If you get a blowjob, the next time you get a blowjob in that same circumstance you can choose Blowjob 1, or you can progress by choosing Blowjob 2.
More discrete (not discreet) curated increments of progress have become more prevalent in recent years. You see that type of discrete event based progress in modern games like
Harem Hotel,
Mythic Manor, as well as older games like
Sengoku Rance.
In purely text based games this makes a little less sense from a fiscal standpoint, but as a progressive mechanic it still seems viable. I think working it as a bespoke mechanical player choice is better than subtle alterations to the event text for a couple reasons. First, it clearly communicates to the player scene expectations. They know they're getting another blowjob, and it will probably be similar but more intense than the previous event. Secondarily, it allows players to experience past event variations if they would've otherwise missed them.
In conclusion: the amount of freedom offered to the player actually traps them into wasting time and feeling like their actions lack impact. In theory you would think you want players to be as free as possible, but in most cases you need to put devices in place to keep people from tricking themselves out of fun.
I wrote this a bit low on sleep, so if anything is unclear, requires further elaboration, or there's something you'd like a more detailed look at let me know. There are other ways to handle grinding I didn't touch on, but this is probably enough for one post.
Normally I think it's considered a little rude to link other games in an author's thread, but it was explicitly requested so please excuse my behavior there.