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I am considering trying anal for the first time. So, for starters, to figure out if you even have any interest in this yourself, and enjoy this at all, rather than starting with something so much larger -- and in some ways, less easy to control -- instead, if you emphasis on YOU want to experiment with anal play, the way to start is with something much smaller and more gradual, like his or your own gloved, lubed pinky finger. Not as a "if you do this awful thing to me, you're getting it, too, " but because sometimes men are interested in anal sex because they enjoy their OWN anuses, and because they are ashamed or afraid to ask for THAT play, receptively, for themselves. 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. Also, because it usually IS very enjoyable for most people with penises, and because it's always a plus with any sexual activity when partners have the same bits to learn about, and when any given person can be and want to be both giver and receiver, it makes for a pretty great learning curve. That said, here's the lowdown on your other questions here. We are not considering anal as an alternative to vaginal intercourse. Starting anal play with penis -to- anus intercourse full-stop isn't the best idea, anyway, on both those counts and more. We're still planning on using a condom with anal though But to toss some mythos aside, because -- again -- the anus and rectum aren't the bowel, anal sex can't and doesn't cause bowel problems. I think it's sage to listen to yourself when you say that maybe you don't want to get into something you're both not sure about and are not sure you'll like. For some, there's also an element of power or even social status in it, as in, my girlfriend LET me do this thing to her sometimes -- but not always -- with the affixed notion that she let them do something she doesn't even like. Using a condom with anal sex isn't about putting a barrier up because the anus and rectum are gross.
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