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ORIGINAL: windchymes

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ORIGINAL: Galacia

It's like a Doctor's appointment for a shot - the harder and faster he shoves, the quicker the whole thing is over.

Awesome. You first. That's right baby, hands and knees and spread 'em. I'll shove this thing in as fast and hard as I can, no problem.

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ORIGINAL: FieryOpal

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ORIGINAL: shiftyw

I second the advice about positions. It hurts like a mofo if I'm on my back, even with pillows under me, it hurts like crazy. For a really stupid long time this is all we did because it was said this was easier on the s type by someone. Eventually I suggested we try it doggy style and it made a world of difference....

Wherever did you hear this? Some positions just aren't conducive to this act until you have gotten accustomed to it. Which takes time.
The side-by-side spooning position that Hillwilliam mentions is more intimate and cuddly.
With some people, nothing but doggie-style works for them. This is what I would recommend for both females and males.
If you (not you shifty!) are on your back, it's best to have vaginal penetration first.
Later on, you can even do this while sitting cowgirl. Reverse cowgirl, not as comfortable. (All right, guys, let's hear the sit-on-it-and-rotate jokes. )