be times when circumstances don't offer a condom so you will always be playing the odds. Finally, here is this situation from an older, male perspective: He wants sex without a condom. You want sex with a condom. You have the say. If he wants sex without a condom,tell him he can have sex with himself. He already knows how. If he has the choice of sex with a condom or no sex, he'll choose sex with a condom. Other Answers (11) You can test him first as see what his reaction is if you tell him NO. Watch carefully as many guys will come on sweet and seem to be so kind Untill they hear the word NO. Ask yourself: Does this man really care about ME or just trying to make it with a virgin and add another number on his list of conquest? I wish you would marry first if you really are happy with this person and trust him. I know this is the year 2012 so many will think marriage first too old for advice yet I will try and advise so. Have him tested and he should still wear a condom as since he had sex before any hiv may not show if he has it for like around 8 years!!! Source(s): Life experience and am married and have three daughters one 34, one 26,and newest just turned 2 April 3rd. Even if you're a virgin, it's fine to get tested. You already know