Well in this day in age having sex with out a condom is a very serious event. I perosnally don't have sex any other way. Condoms are the only way to go as far as I am concerend. Between STD's, AIDS and pregnancy condoms are cheap insurance.

There are several thing he should do.

1. Try several differnet condoms. Many online stores will sell sampler packs.
2. If he is larger either in length or girth or both try larger condoms, basically Tojan Magnums or MagnumXL. The XL are pretty much the largest you can buy.
3. Condomania.com has more custom sized condoms. You have to measure yourself with their measuring system to select the proper size.
4. Never have sex with out one, at least as far as STD's are concerned. If he is in a long term relationship and they have figured out the brthcontrol issue, otherwise get used to condoms!