Here’s how I would do it…I’d have one person put on the condom and roll it all the way down their shaft. I’d then take the tip of the condom and stretch it out while rolling out out more so there’s about 5 - 6 inches of condom pulled forward. Then cut the tip if the condom off and then pull it on the second person. They’d have to hold it in place, but it should work. Would love to try it with you.