Then, when you feel cool, calm, and ready to start exploring anal play, you or your partner can use a finger or sex toy to massage the outside of your anus. This can help you get familiar with the sensation before any kind of penetration happens. Once you’re beginning to enjoy yourself, Dr. Chinn says you can experiment with sticking a finger or sex toy in your anus bit by bit based on what feels good, using plenty of lube, of course.
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Your man also needs to be someone who will actually follow your instructions too. If he thinks he is going to be in control and calling the shots, then you are going to have to bring him down to earth and let him know that this won’t be the case. Doing this isn’t so that you can “dominate” your man, it’s so that you get to experience the pleasures of anal sex AND NOT THE PAIN.

For some women out there, anal sex is the cherry on top of a sexual sundae: a little extra treat that elevates something that was already delicious on its own (duh, talking about sex here). But for others, it's more like pâté: intriguing enough, worth a try, but absolutely not up their alleys (as in, a penis will probably not be going up that alley ever again).
Very naughty buttfucking videos featuring smoking hot babes from the porn industry. Lovely coeds who experiment with anal sex for the first time and end up begging for more. Enjoy big breasted MILFs and matures putting their asses on the line to seduce younger studs in a heartbeat. Curious maids snooping around employers' bedrooms to get their big round asses destroyed without mercy.
16. That being said, you can totally clean things up. The key to anal play is comfort, so do whatever you need to help with any lingering anxiety. "Using an anal douche is not harmful if only done once in awhile and might help you relax your concerns about your bowels," advises Pierce. You can use something as simple as warm water for a quick cleanse too.

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.
13. You can vary up positions. No, not all butt stuff needs to be done doggie-style. It's true it might be a little harder to get some solid eye contact going on when face-to-anus things are happening. But! There are a variety of positions to try, like lying on your back with your hips elevated or sitting on his face in reverse-cowgirl. Move around until you find one that makes you feel most at ease.
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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