If you want to be more direct with him, you can ask him, "Where do you think we're headed? Some relationship discussions are okay to have while you are out in public, but a discussion about something as personal as your first time together should be had in private and just between the two of you. Having someone to talk to and confide in is one of the beautiful perks of being in a relationship. An email or handwritten note may be a perfect solution if you are having a hard time verbalizing the way that you feel. In fact, it can be advantageous to keep him in the dark about certain things, like these. Whether you have been with other guys or not, your first time with someone should be special. You should also have a conversation with your boyfriend about contraceptive options, so that you are both taking responsibility for your sexual health. Just relax and make a plan to discuss your feelings with him. If you think that he will say yes and want to have sex right away, prepare your surroundings. Your Cheating History iStock Fessing up to this bombshell can have crazy-serious repercussions. Light a couple of candles and invite him over to watch a movie, listen to music, or play a game. Of course, what you decide to do is totally up to you, but experts say not fessing up isn't a deal breaker. You can strike up the conversation by saying: You shouldn't keep full-blown, past relationships from your partner, but leaving out a lip lock here and there won't hurt. Not every detail has to be shared. Or you can try something more suggestive, tell him what you're wearing or go with the classic "What are you wearing?