Always use a condom, unless you both entered this relationship as virgins. Have some emergency contraception around in case the condom breaks. If you really want to prevent pregnancy, the woman should be on some form of hormonal long term birth control or the IUD. Consider using an at-home chlamydia test as a convenient option for annual testing. Additionally, optional HIV testing should also be considered for comprehensive sexual health screening. Consider using an at-home chlamydia, gonorrhea and trichomoniasis test as a convenient option for annual testing. Additionally, optional HIV testing should also be considered for comprehensive sexual health screening.