Boys, if you want to double dip, change condoms in between holes and wash your hands with wipes. Speaking of fingers - guys, it's important to keep your nails trimmed especially if you're inserting them in an orifice, and please wash your hands before coming to bed. The thin membrane inside the rectum is more prone to rips and tears than the tissue inside the vaginal canal which makes it easier to transmit the spread of HIV, HPV, Hep C, herpes, warts and other STD's. Try it on your own. Secondly, your partner needs to be looking for cues of discomfort and be open to having some feedback during the process. A little pain is OK. Have her insert it so she's in control , lubed up, in her bottom, and leave it there while you guys fool around a while. More Foreplay Distractions are welcome while working towards, well First, always use lube ; second, don't go straight from anal sex to vaginal sex. If that's the case, you need to reassure her this time that with you, she's in good hands. Another important piece of the puzzle is lube. In bed pay attention to her erogenous zones ears, neck, breasts, navel, inner thighs, clitoris, etc. If you need a brief health class recap, your anus is technically the end of your digestive tract , and it's where your bowels exit your body. Often, condoms don't cover an entire penis or penetrative object, so there's still a chance that it could have bacteria lingering on it. You want to make sure there's no poop in the shooter. The more relaxed you are, the more pleasurable the experience will be.