Leisure Suit Larry was the first game I played as a kid that felt “adult” and “naughty”. Somehow that made it irresistible to my younger self. This brings back some great memories. Thanks for sharing!
https://www.youtube.com/watch?v=G1om9GlBhn8&t=3m17s
Oh yeah! Ladies and gentlemen, Al Lowe!
There was a casino that let you bet negative amounts at the blackjack table, then lose on purpose to make lots of money!
https://en.wikipedia.org/wiki/Softporn_Adventure
Then there was "Interlude: The Ultimate Experience". It came with a paperback book full of naughty stuff, which my pirate friend gave me a xeroxed copy of to go with the floppy disk.
https://boingboing.net/2012/08/10/sexy-video-game-from-the-a...
You'd load the game on the computer, run it, answer some questions, and it would tell you and your (probably imaginary) partner: "For a good time, turn to page 74 for Interlude No. 82 - Caveman Caper!"
Looks like this PDF has the table of contents, but it's missing all the "good" parts:
http://www.brutaldeluxe.fr/projects/cassettes/syntonic/k7_sy...
And I'll never forget the HyperCard Smut Stack! ("ping!")
Sounds a bit like one of the early bugs on Amazon.com:
Ah, good times.