Slowly insert the finger up to the end and make circular motions with the whole wrist, without moving the finger in and out. When I asked him about it he told me that he didn't like it, that it felt too planned, too much worrying about the clean-up , mostly because he can't come from anal, so we usually have vaginal sex after that but he has to clean his penis before we can do that. To find out more, including how to control cookies, see here: We've tried starting off with vaginal but then he can't get hard enough for what is essentially round two of anal. The anus contains many nerves as well, which can also react in a pleasurable manner when excited. This is an example of the kind of ignorance out there.
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Again, judge her reaction to decide whether or not you should proceed. Just try again the next time and hope for a more positive reaction. I feel like I just said anal a million times, but I'm not sure how to handle this situation and mostly I feel really alone. However, anal sex needs to be discussed well in advance, as unless you have an ant penis, he anus will need to be relaxed. Just run it right over the anus slowly and see how she responds. I've always been a huge fan of butt play -- dildos, fingers, vibrators. Excellent advice and very well written.