From Behind – Once you are comfortable with your man having more control and doing all the thrusting, then you may want to try out some doggystyle type positions, where your man is fucking you from behind. I’ve put together an entirely separate guide on the 19 best anal sex positions here where you are in the doggystyle position or a variation of it.
For comfort in entering anally, it works to be really turned on before anal entry. Deep kissing, squeezing nipples, rubbing the vulva and having vaginal sex for a few minutes first really helps to relax the anal muscles. Using lots of lubricant, the penis can push slowly, and if there is any tightness at all, withdraw and wait until the woman feels ready to do it again. The second time again entering slowly will be more relaxed and ready. If the woman rubs her vulva hard as entry happens it will more likely be pleasurable . If not, withdraw and try again when ready. Certainly it helps to have a caring partner who you can trust to be gentle. Once you are warmed up you can go pretty hard and it’s likely to give you a really great orgasm, more than you get vaginally.

Contrary to popular belief, guys aren’t the only ones who are ass-obsessed. Look, like we said before: there are a lot of nerve endings back there. It feels good; that’s just biology. Sure, your anus is tighter than your vagina, which is going to blow your man’s mind. But anal sex is also an extremely intimate act that can actually bring you and your partner closer together. You’re not going to let just anyone go there, and he knows it. That’s hot.

Fortunately, sex educators have met this rising demand with a wealth of how-to guides and things to keep in mind for those exploring anal. Unfortunately, many people dive right in without doing much research. That means, what little anal education many first timers have often comes from porn, where anal is often portrayed as easy: just shove an unlubricated toy or peen up an asshole, with no preparation, and pump hard for, like, an hour.
Some infections can cause problems during pregnancy, such as Giardia (giardiasis) and Group B Streptococcus (GBS), among others. Giardia can cause chronic diarrhea which may lead to dehydration and malnutrition, both of which can be dangerous during pregnancy both for the mother and fetus. GBS may be transmitted to the baby during delivery and can lead to an infection in the infant. Both Giardia and GBS often colonize the rectum and can be spread to the vaginal tract if vaginal or oral sex follows anal sex, or if there is any touching (hands or genitals) after anal sex.
7. “It’s tighter around the actual butthole itself then less so deeper in. I’ve tried it with my partner a few times, but have never managed to cum from it because it doesn’t stimulate the more sensitive parts on the end of my penis enough. You might find that you enjoy it less then PiV, but you may also find that the hotness of it does it for you.”
“The truth is that our minds have this incredible way of making things less enjoyable for us, if it’s something that we’re not totally into,” Levkoff says. “If we’re nervous or uncomfortable our body shows it — our muscles tighten, we start to clench, we feel anxious, we’re not relaxed and ready anymore, and that means we’re less likely to feel pleasure.”
"The key to good anal—yes, that's a thing—is having a partner you trust completely and who will do it right. That means lots of lube, start small with a pinky finger just like in Fifty Shades, then work your way up to small toys or butt plugs. After that, anal can be amazing! It is super intense, and your lover has to be extremely delicate and careful and be a good listener and super patient—and you as the receiver have to have a lot of trust in that.

3. If it hurts, stop! Some, well, let's call them new sensations are to be expected—a lot of women say it feels like they need to poop, or like a primal, pressure feeling. But like any other sex act, if things start to hurt in a way that's no longer fun, you should stop. Injuries from anal sex are possible, but super rare. Pain most commonly comes from anal fissures, or little tears in the tissue around the anus, which is very thin and delicate. A good way to remedy that is using lots of lube and smarting with smaller objects, rather than big ones. 
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