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Ask MISSter Simms – I’m Jealous of My Boyfriend’s Sexual Past

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Can sex still be special if your boyfriend is a kinky dude who’s had multiple past partners?

Dear MISSter Simms,

I’ve been dating my boyfriend long distance for the past 9 months.  He is far more experienced than me when it comes to sex.  I am a virgin, while he has had 16 other partners.  This, and the fact that he’s into kinky stuff like video taping, kind of bothers me.  I feel like nothing will be special between us because he’s probably already done it all, while I have done nothing.  I told him I don’t want to do anything that he’s already done with some other girl because I don’t think it’ll mean anything to him, but he says that it will because of the feelings that he has for me.

I feel like my jealousy is something that will get in the way more as time goes by.  Is it wrong for me to feel this way?

Jealous Lover

Dear JL,

First, let’s get this out of the way.  Sex is not “special”.  Don’t believe what you’ve seen in some random TV show or in the movies…unless those movies happen to be porn.  If you indeed are a virgin, your first time having sex especially will not be “special”.  It will be awkward, messy, and probably even painful.  You’ll look back on the experience like, “Man, that kinda sucked…”  After that, however, it’ll probably become much more enjoyable, exciting, intimate…but not “special” in the way that you’re thinking.  This ain’t like the 40 Year Old Virgin where birds start chirping and the sun shines down on you after you’ve done the deed.  No need to put so much pressure on it.

That said, it doesn’t matter whether your boyfriend has banged 16 people or 1600 people.  If and when you two get to doing the horizontal mambo, it can still be “special” in that it’ll mean something to you both.  Like your boyfriend said, it’s all about the feelings you two have for each other.  You’ll both be more comfortable communicating what you like and don’t like, and you won’t be so self conscious like people can become when banging strangers.   And because of your boyfriend’s experience, he’ll probably be able to do a lot of things to make your first time the best it can be.  Trust me.  There’s few things more awkward than two virgins trying to get it on.

Whatever you do, though, don’t videotape anything.  Unless you’re Kim Kardashian, those things have a way of haunting people in their future.


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