Grasp the outside of the tip with your fingers (from the side, to avoid getting it with your nails), squishing the lube. Hold it pinched shut while you put another dab of lube on the fingers of your other hand. We shall call the first hand (the one pinching the tip) the “condom hand” and the other hand the “lubey fingers” hand for step #4.
4. Roll it on like a pro: With your condom hand tightly pinching the tip, set the condom on your partner’s cock. Keep pinching that tip with your condom hand, because it needs to be empty of air and NOT rolled tight against his penis.
Got your lubey fingers ready? Those slick fingers are going to make it easier to roll the condom down. Rest the sides of your lubey pointy finger and thumb just above the rolled rim, one on each side. You’re using the sides so that your nails (even if they are short) don’t snag and rip the precious condom. Press in firmly, but not roughly, with the sides of your lubey finger and thumb (still pinching with your condom hand) and stroke your fingers down.
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.