Here’s the best video I’ve ever seen on different ways of putting on a condom for guys who are uncircumcised.They show a method we never see here in the States for men whose foreskins are long or don’t retract. It’s from an HIV prevention site in New Zealand and it was made for gay men who are having anal sex. Hopefully, you won’t have a problem with that if you’re straight.
If you’d like to try out different condoms to find the ones that are best for you, see my page full of condom sampler packs.
This site from New Zealand also has the best how-to videos you’ll find on how to have anal sex, which are just as helpful for straight couples as gay couples HOWEVER, they have now put these videos on Pornhub–so beware, these links will take you to Porhhub: How To Have Anal Sex for Tops and How To Have Anal Sex for Bottoms.