Not worth it. Fecal matter isn't exactly bacteria free. He risks bacterial infection and a urinary tract infection. You risk bacterial infection in and around your anus. You also risk a bacterial infection in your vagina as well as possibly a urinary tract infection. UTI's are usually more dangerous for women than men. However if he gets one then if you have regular sex, you can get one.
Try the condom again or try different brands to see what works. Use plenty of lube.
You or he don't really want to be having anal sex without a condom. It's just not a safe thing to do.



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but scary at the same time. 



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