I had no idea about a couple of things on this topic until I did a bit of exploring.
Yes, the obvious is easy. A little blue pill can be a life changer. It works for me. It’s like going in knowing your beat up old Volkswagen is gonna run a decent quarter mile with the Porsche you’ve selected to take your money. I like being with women who wouldn’t normally give me a second glance, that can cause issues.
Shave or otherwise get rid of hair on your junk. Yea, it makes it look bigger, whatever. I’m average in that department and I don’t really care how big it looks. Can I make eyes roll back in the head? Occasionally.
Condoms pull at hair, make the fit uncomfortable and are generally a nuisance. I can get the condom on further making a nicer fit with no hair. Just like previous posters have said, there’s no shame in using V or C, try a bigger condom. You might think those are just for the guys on “monsters of cock” but I’ve discovered that they feel pretty nice. Same with the extra thin ones.
Also, try a cock ring. It’s fun and some girls find it’s fun too.
Lastly, have a glass of ice water beside the bed. If you feel yourself getting soft get her to put an ice cold finger up your ass. Works for me, I’m not a medical doctor but it’s sure fun.