Manual sex feels fine, so why does intercourse hurt so much?

I am a virgin, but my boyfriend has had sex before. I am positive that I am ready to have sex with him and we have attempted to do so three times already. The problem is that is causes me excruciating pain. I understand for most girls it causes some pain, but this pain is unbearable and I haven't been able to go through with it. When he fingers me he can fit 3 fingers in so I don't see what the problem is. We take our time and don't just skip right to sex. What should I do?
Heather Corinna replies:

Sometimes, when we perceive pain before it happens, we feel pain because (primarily) of that perception. It's called a perceived pain event when that happens.

Suffice it to say, that happens a LOT to a lot of women with first intercourse because of all the stories we hear about how terribly painful it can be or is going to be. When we anticipate genital pain, too, the vagina tends to clamp itself shut, so trying to force anything inside at those times is going to hurt. And when it IS painful, we tend to -- logically -- expect it to be painful again and again.

But more times than not, when there is not a hymen issue (which doesn't sound to be the case with you, since manual insertion is no problem) or an infection, and everything else is in place, even with first timers, it really shouldn't be painful. And for those who don't expect it to be, it's less likely to be.

So, let's check the basics first.

Are you:
• Using PLENTY of latex-safe lubricant? Even if you're not using condoms, that's important, especially for women on hormonal methods of birth control, as they can make natural lubrication more scanty. Plus, lube always makes even already-great sex feel better. Really.
• With a partner who is VERY gradual in his entry? In other words, who is going very slowly, as it feels good to you, and only going as deep as feels good to you? Are you communicating well throughout?
• REALLY taking your time with other activities beforehand, even to the point of reaching orgasm BEFORE attempting intercourse?
• ONLY having intercourse when that's something you really want to do? For instance, if for the time being, all this pain just bums you out about it, are you taking some time away from it, and only engaging in the activities you know you enjoy?
• As relaxed and aroused as you can possibly be (and I know, with expecting pain at this point, that isn't likely possible) before intercourse?
• Part of a healthy relationship and dynamic overall? Do you trust your partner, feel safe with him, and feel safe exploring your sexuality with him?

If ANY of those items aren't the deal, time to tend to them. If they all are, then it never hurts to check in with your OB/GYN and make sure nothing is amiss physically.

And if all those items are in place, and your gynecologist doesn't see a reason for the problem, we can pretty safely assume it's likely a psychological issue -- you either really don't want to have intercourse, or can't stop expecting pain. In that case, the best advice I could give you is to suss out what that is, and take a break from attempting intercourse until you work it out.

I've gone over most of this already, but as supporting advice, I'd suggest you take a look at this Yield for Pleasure and this From OW! to WOW! Demystifying Painful Intercourse, and also pass them on to your partner.

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