A guy who I've been seeing for a few weeks has never really bottomed or enjoyed bottoming in the past. Oddly enough he does enjoy it when I do it to him until he cums (with me still in). However, when he cums he becomes ridiculously tight and it is painful for him to expel me or for me to pull out...
I've tried triggering diversions (e.g. biting his neck hard to distract him, or pulling out while he's cumming), but they do not seem to help. Has anyone else experienced this before or know of tips to help?
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Just so I understand: Is it painful for you, or for him, or both?
Orgasm triggers muscle contractions for a lot of people, and, as you likely know, the sphincters (rings of muscle) at the opening of the anus are very strong. This is likely why the contractions and accompanying pain are still present even when you pull out during his orgasm.
With any kind of sexual activity, it's really important for partners to talk, both about the good things and the problems. Have you talked to this guy about this and what he thinks might work for the two of you? It's especially important to do lots of talking because this is a relatively new sexual activity for him.
Here are a few articles to read that explain the anal anatomy more and might give you some more ideas to consider:
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