The condom should roll down smoothly, whether you prefer lots of little strokes of your lubey fingers, or one slow sliding motion.
If it does not roll down smoothly then your condom may be inside out OR it may be a bit tight. You can do the inside-out test right there are his penis to find out. Inside-out? If you haven’t rolled it down or struggled with it at all, you can go to step 3 to fix it. Otherwise, get a fresh condom that you haven’t wrestled with yet. Too tight? If it’s only a little too tight you can roll it down more firmly, perhaps with the lights on. If it is uncomfortably tight then call your super-cool roommate and ask them to pretty please run to the store for XL condoms. The good (grown-up) boy/girl scout will have both sizes in their bedside table already!
Hey, check that out! That condom is on, with a stimulating drop of lube inside for him, and some more outside for you. You didn’t even need to turn on the lights or pull off your blindfold! Oh my goodness, I’m so proud of you.