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It's just not worth it to constantly be stressing over this and feeling dissatisfied with the way things are after we've been dating for this long. But this phase isn't going to be short.
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Well, for starters, it means always always using plenty of latex-safe lubricant and a latex barrier with anal play -- anal sex of any kind carries STI risks at the level vaginal intercourse does, as well as additional bacterial infection risks, and the anus and rectum don't self-lubricate like the vagina does, so both are vital to safe play with such delicate tissue. Using a condom with anal sex isn't about putting a barrier up because the anus and rectum are gross: That also means a partner or yourself, if you're adding anal stimulus to masturbation , being very slow and very gradual with any kind of anal sex.
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