Oh yeah, not getting a "happy ending" your first time is something that happens to a lot of guys. It's nerves that turns into anxiety over something being wrong, and once that sets in, it becomes difficult to stay focused and in the mood. It made sense to me to go that way for Connor's first time considering how panicked he was earlier in the day and how quickly the hookups happened.
There are a couple of scenarios where he can finish, and those share in common that he's much more comfortable with where he's at during those times. There are two of those in the current version, if you haven't found them yet.
If you skip the hookups in this section and have a first time later on in the game, he won't have the same problem because in those scenarios he'll be much more at ease. But those scenes are yet to come. No pun intended 😉
Anyway, thank you again for the kind words! At the end of the day this game is basically about building your own fantasy, whether that be hookups or romances or both. But I wanted to add layers of reality to ground things. Like having a young writer panic about the quality of their writing, haha