First, let us clear up some myths:

Anal penetration will stretch you out (permanently) - This stubborn myth says if you engage in anal sex/penetration you will cause your anus to permanently become "loose" or lack control.  The real situation is that the anus and surrounding muscles are quite stretchy and resilient.  After opening after a bowel movement, penis, or plug, the anus will return right back to its normal position and condition.  Done right, no harm will come to your anus and it will serve you the same way as it always has.

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Anal sex is supposed to hurt - Because of the lack of good information out there, people engage in anal sex/penetration without proper prep.  This usually will result in a lot of discomfort or pain initially or during the entirety of the session.  The fact is that anal sex can and should be pleasurable for both parties, the giver AND the receiver.  That is the whole point of sex... pleasure.  With proper preparation, anal sex/penetration is just that.  Lastly, pain is the body's way of saying stop, damage is imminent or occurring.   Listen to it to avoid temporary or lasting discomfort or damage.

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Only gay men engage in anal sex or play - This myth is fading a bit, but still persists (particularly with the straight male population).  While it is true that a good percentage of the gay male population engages in anal sex, every one else has butt as well.  Anal play is pleasurable to anyone with an anus, not just an anus owned by a gay man.  Deriving pleasure from giving or receiving does in no way indicate what one's orientation is.   It just makes you human.   So, enjoy your booty, or the booty of your partner, for the simple fact it is feels good and not that it affects who you are.

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Is just wrong - Whether it is social, cultural, religions, or any combination of the three factors, there is still taboo surrounding anal play/sex.  It could be that "normal" people don't do that, or sinners, something reserved for deviants or "perverts".   Again, anal play is just yet another way to enjoy your or your partner's body.   The day is coming that people begin to accept anal as just another part of sex just like oral.  

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What about poop!?:

A very common concern is will there be poop?  Let's be honest, sh*t happens.  Engaging in anal penetration is involving a part of the body whose main job is waste elimination.  Yes, poop travels through your rectum and anus.  Yes, some residual can be present at any given time.  However, feces are stored only temporarily in the rectum prior to a bowel movement.  If you do not feel the urge to use the toilet, you may experience very little to no residual.  This is certainly no guarantee.  Just understand that if you are participating in some backdoor play, you run a risk of having poo make its way out or onto the toy or penis.  If everyone involved understands this, then relax, have fun, and happily accept the outcome. 

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Planning ahead:    Want to keep things as tidy as possible?  For some of us it is no big deal to hop up afterwards and head to the bathroom for rinse.  Others may want to take steps beforehand.  The first step that anyone can and should do is be sure you have emptied your bowels.  Don't need to go?  Then you should be as good as you can be.  If you want a clean exterior, a quick shower, bath, or wet wipe down are easy methods.  If you want to clean up the interior, then an anal douche is the best tool for the job.  A basic anal douche has a nozzle attached to a squeeze bottle/bulb.  Fill the bulb with warm water only, gently insert (lube helps), squeeze the water into the rectum, and evacuate it into the toilet.  Repeat perhaps once more, but do not overdo and strip away the protective mucous layer.  ​​​

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When you are ready to get to the fun part, it can help to have a few accessories ready.  Laying down a sheet, towel, or blanket to catch any fluids is recommended to keep the underlying surface tidy.  Waterproof blankets specially designed for sex (like the Liberator Fascinator) are excellent choices for this.  A separate cloth might come in handy to for any clean up desired during or after.  Anal penetration requires plenty of lube and it is easy to get it everywhere when things are hot and heavy.  Speaking of lube, this is a requirement for any anal sex session (see below).