Dear Em and Lo,
I was married for 20 years and now I am not. I’m not crying in my soup (is that the term?). I’ve learned a lot about what makes for a crappy relationship and bad sex. And, thanks in large part to your articles and website, I have gained a sense of humor, sexual confidence and a pretty good idea about what makes for great sex and good relationships. I’m ready to give it all a go. I’ve dated a couple of guys since becoming single six months ago (the relationship was over long before it was over, so the grieving has been done). Recently, I met a guy that I have come to REALLY like. We’ve both expressed to each other in many ways, including some pretty suggestive and fun flirting, that we are really into getting to know each other even better.
So here’s the question: How great should the sex be the first time if I want this guy to stick around? Do I pull out all the stops? Should I plan on maybe just one of the little ideas we’ve flirted around? What about role-playing and/or dress-up the first time? I kind of wonder if I should steer things in the direction of just pure romance the first time, or is jumping right into what is fun for me — and apparently him too — a good idea? I feel pretty comfortable with my decision to not introduce any toys or gadgets the first time. But what if he suggests or comes up with one? Should I say that I’d prefer au natural at first and promise we’ll get to the toys on another occasion? Or, should I let him show me how creative he is and what he likes to do?
I might not have these questions if our circumstances were different but here’s the deal: His wife died, after a long illness, ten months ago. He was happy with her. He has dated a little but I’m pretty sure no or not much sex. I’m desperate for some great sex and a great connection. He’s really hot for me but has mentioned he wants to take things slowly, which, even though I’m itchin’, I think is a good idea. Still, I don’t want him to be disappointed once we finally do get around to it. I’d love to know what you think about this.
— (Almost) Back in the Saddle
Okay, let’s get one thing straight before we go any further: This man is not going to be disappointed! You’re full of sexual confidence and excited to have fun in bed, you guys have great chemistry, and he probably hasn’t had sex in a loooooong time. Just plain old vanilla sex is going to melt him like butta! Chances are, in fact, he’s more nervous than you are (especially if he hasn’t had some good online friends regularly encouraging him like you have). So take a deep breath and just try to enjoy the fact that you’re about to have sex with your new crush. It’s been a loooooong time since you had sex with someone new, and half the fun of this is the anticipation!
As to what you should do in bed the first time, there are no hard and fast rules, it really all depends on what you’re both comfortable with. You don’t want to act like someone you’re not in bed, just to please or impress your partner. If what really gets you off is whips and chains, you don’t want to keep that a secret from your partner for an entire year — just in case that’s not their cup of tea at all. If, on the other hand, you enjoy role-playing about as much as a root canal, there’s no point in pretending you love it in the beginning, just to be agreeable — because then you’re setting yourself up for a lifetime of sweaty latex nurse outfits. It’s better to find out if you’re sexually compatible before getting in too deep.
That said, being willing to try some new things earlier rather than later can set the right tone for a relationship: it establishes the fact that you’re always going to be willing to experiment, at least a little. If you wait until you’re in a rut to break out the blindfold and switch positions, it’s likely to feel a lot more awkward and out of place. So we’re thrilled to hear that the two of you have already talked about role-playing and dress-up! We see great things for the two of you in bed.
But there’s a difference between first-time sex and early-relationship sex. We tend to think that first-time sex — assuming it’s the beginning of a beautiful relationship and not a one-night stand — doesn’t really need any accessorizing. (Except for lube, which is always welcome.) First-time sex with a new partner is serious sensory-overload. For example, this is probably be your first view of each other’s O-faces! You don’t need to bend over backwards in some Kama Sutra position because the basics still feel brand new and exciting. Plus, you’ll probably both be nervous, which isn’t really conducive to pulling off complicated bondage knots or the wheelbarrow position or nurturing your inner saucy librarian/naughty farmhand. There’s also something to be said for having at least a little experience in bed with each other before making sex technical or theatrical. The better you know each other, the more likely you are to know when it’s the right time to whip out the spanking paddle.
That all said, we don’t think you should necessarily rule out anything. Go with the flow and if something feels right and good and sexy in the moment, then do it! If he suggests a toy (though we doubt he will, given that he’s nervous and wants to take things slowly) and you think that sounds like a fantastic idea, then buzz away (just make sure you put a condom on that too if it’s not fresh out of the box!). But even if you don’t break out any toys, your new-found sexual confidence will still come into play whenever you have sex. It takes a lot of confidence just to ask for what you want in bed — and that might be being led around like a pony, or it might just be a certain manual technique that really does it for you.
On a final note, we know we said that the anticipation is half the fun of first-time sex, but we also want to caution you not to go in with overly high expectations. While sex with a brand new partner is rarely dull or boring, it can sometimes feel awkward or clumsy — and for a woman, it’s not always particularly orgasmic. Sometimes it takes a guy a while to find his way around a new partner’s body, or it takes her a while to become comfortable and relaxed enough with him to climax. (Or it takes her a while to become comfortable and relaxed enough with him to explain how exactly he can get her to climax.) In other words, don’t sweat it if the Earth doesn’t move the first time around. It doesn’t mean you’re destined to have bad sex together and it definitely doesn’t mean you’re not meant to be together. Just think of it as having something to look forward to.
Have fun storming the castle!
Em & Lo