There are really no rules here. The best thing to do is just relax, enjoy and experiment. If trying it for the first time, simply squeeze a little lubricant onto your fingertips and gently apply to your intimate areas. Lubricant can be used with or without a condom, either when it is already on or before. Take care not to use too much before you put the condom on, otherwise it may slip off during sex. You can always apply more if you need it.