Your rectum is not a vaginal canal, nor is it a mouth and throat, so don't expect your anus to work like other orifices. Anal play should be pain-free, so take it slow and pile on the lube (or spit). Switching from anal to vaginal sex without replacing the condom or thoroughly washing the penis or dildo can lead to a vaginal or urinary tract infection. If you're fluid-bonded with your partner - meaning you've chosen to stop using barrier methods, a choice that should be based on the results of comprehensive STI testing - it's still important to avoid transferring bacteria from the rectum to other parts of the body, for example the vagina. If you're not using condoms, utilize other methods to reduce the risk of transferring bacteria. (Of course, even if you are using a condom, many common STIs, including syphilis and herpes, can still be transmitted by skin-to-skin contact.) 2. You should also utilize dental dams during anal rimming, and nitrile gloves during manual penetration. To minimize risk, you can use a latex condom (like this one from Sustain) or polyisoprene condom (which is free of allergens, like the Skyn condom from Lyfestyles) during anal sex with a penis or dildo, unless you can completely sterilize the dildo.