The Pro
My first response is... eek! But I’m supposed to be the “pro” here, so let’s move on.
I’m wondering why this is so important to him. Is this some sort of “ideal” he has, that you must know everything there is to know about each other? Could it be that it turns him on to hear the details of your past sex life? (There are men who like that sort of thing. They get to imagine their woman in a sexual situation with another man without the risks and agony of actually having to witness it. It’s all in the past, so it’s not so loaded with jealousy.)
But even if that were the case, it seems to make you uncomfortable, and you shouldn’t have to do anything you’re not comfortable with. Besides, it’s my opinion that this is a dangerous road to take. I don’t see what good can come of it. It’s the classic scenario where the guy gets you to tell him how many lovers you’ve had before him. After he’s convinced you that the number really won’t matter to him, and you foolishly tell him, he’s outraged, feeling emasculated, and calling you a slut! Or he’s acting dejected and needing reassurance that he truly is the best, the most fabulous, the most virile—oh, and let’s not forget... the BIGGEST!—lover you’ve ever had.
I remember a boyfriend of mine who made the silly mistake of asking me while in the throes of a romantic tête-à-tête on the beach whether it was the first time I’d done something like that. I hesitated when I probably should have just told a little white lie on the spot for the sake of his ego, and he was crestfallen... not to mention embarrassed for even asking. Talk about killing the moment!
The past is the past, and you don’t have to tell him everything.
It’s unhealthy and unreasonable to expect a new lover to reveal everything about their past, and it will set a bad precedent if you give in to his demand. What’s next? Will he be asking you to confess to him every time you so much as glance at another man as you go about your day? Will he want to know when and how often you like to pleasure yourself when he’s not around? Beware of those who need to know everything about anything that really doesn’t concern them. It speaks of a controlling and potentially obsessive personality, and relationships with people who have such tendencies ultimately become difficult and sometimes even dangerous. You are wise to question his demand for complete disclosure about your sexual history. It’s none of his business, and if he can’t live with that, you may find that you won’t be able to live with him.
The Joe
Shortly after deciding they had a better chance of survival if they moved in together, a caveman turned to his cavewoman and grunted something along the lines of, “So how many other men’s backs have you eaten fleas off? You mated with our cousin Urg, didn’t you? Didn’t you?!”
Evolution may have led to opposable thumbs and, in turn, MarioKart for the Nintendo Wii, but we’re still waiting for the mutation that prevents guys from thinking it’ll somehow be beneficial to know their partner’s sexual history. You’d think that after a few thousand years of the conversation ending badly, we would know better than to initiate it. But it still happens. If there was ever a convincing argument against Darwin’s theory, I’d say this would be it.
All tenuously appropriate (at best) evolutionary metaphors aside, what I’m trying to say is that your boyfriend’s an idiot and you should know better. How does he not think this will lead to an argument? And telling him “EVERYTHING?” Seriously? Despite what parents tell their children, honesty is not always the best policy.
“I won’t get mad, honey. I just wanna know. I thought we could share everything.”
“I had sex with Carrot Top.”
“Uh... yeah. I don’t think I can be with someone that slept with a prop comic.”*
It goes without saying that maintaining some semblance of a healthy relationship requires a great deal of work. Open communication, the ability to compromise, keeping your naughty bits out of other people, blah blah blah... all that’s a given. What’s a little less clear to many women is this: Occasionally, lying is perfectly acceptable. In fact, it’s necessary if you’re in it for the long haul. Men have known and understood this for years. I wish I could say things like, “Your mom’s an awful human being,” or “Your friends Mary and Hayden are hyper bitches,” or “Yeah, you could stand to lose a few,” but I like the thought of having sex before I need Viagra to do so.
So the next time your boyfriend asks, you’re left with a decision to make. You can omit a few of the more carnal details, or you can tell your boyfriend the truth that he mistakenly thinks he wants to hear. One will lead to continued relationship bliss. The other will not.
Whatever you choose, just know this: You are dating a douchebag. As long as you’re both tested and clean, this isn’t any of his business.
*True story. A friend of mind got dumped after coming clean about getting dirty with the Ginger-haired performer.