Hardness

[Gt1956]

That’s what I’m trying to figure out is it better to be very hard for 15 or softer for 30?

I think pehaps you're looking at it a bit wrong. It is my understanding its more of a pain vs time thing. In other words, if you can stand longer than 30 minutes then there is a chance that you're not pumped enough. If pain causes you to release before 30 minutes then you're pumped too much.
Using pain meds to mask the pain probably isn't a good idea. You're not trying to stretch it all in one month. It takes time. As in months, maybe over a year in some cases to get to the end of stretching. You'll see many members use the word patience. There is a good reason for saying that. Its like the tortoise vs the hare. Steady, regular patience in pumping gets you there.

[Confusedjourney]

I guess I’m also trying to figure out how much to pump where I won’t be in pain during sex

[AST2123]

That’s what I’m trying to figure out is it better to be very hard for 15 or softer for 30?

I would go for very hard for 15 minutes rather than softer for 30 minutes (when cycling). This is how you will stretch over time. If you inflate for 30 minutes soft, you will reach the hardness you want at all. You have to be tolerate the pain. Today it is painful at 15 minutes. One week later it will be 20 minutes, and so on, till you reach 1 hour or more.

[Gt1956]

That’s what I’m trying to figure out is it better to be very hard for 15 or softer for 30?

I would go for very hard for 15 minutes rather than softer for 30 minutes (when cycling). This is how you will stretch over time. If you inflate for 30 minutes soft, you will reach the hardness you want at all. You have to be tolerate the pain. Today it is painful at 15 minutes. One week later it will be 20 minutes, and so on, till you reach 1 hour or more.

I agree, out of the two options. Not hard enough for longer doesn't provide as much, if any, stretch.
At least timing out because of pain, you've forced it to stretch. Just for less time.

[AST2123]

Adding this post: Similar case. Now he can go for an hour without pain.
viewtopic.php?f=6&t=18165&p=165506#p165506

It is pretty normal at early weeks to have pain, and differ from one to another.