"It's fine to have anal sex, as long as you aren't in high school."
An Introduction To Anal
This won't be anal 101. I'm not going to describe what it is to you. If you are reading this, you already know exactly what it is...and are looking for tips. First, let's look at why anal can be so much fun.
There are a shitload (no pun intended) of nerve ending in the anus. This is part of the reason anal can be so damn fun...or positively horrid. Men can often get pleasure out of the feelings of pressure on the prostate, through the wall of the rectum (for more on this, check out my article here: Male Anal Stimulation Is Not Gay: An Inspection of the Stereotype. The prostate can be immensely pleasurable when stimulated. Women can draw an amazing amount of pleasure from the combined feeling of the anal nerve endings being stimulated along with the stimulation presented by the "shared" nerves leading to the clitoris. Some women even claim (I am obviously male, so I can't speak in certainties here) that the g-spot can be hit with the right anal angle.
What you are actually here for: MrWilly's Wild And Wonderful Guide To Anal Adventure!
Everyone has their own tips. I will only be providing what has worked for me, and what I have been told works for others.
Step One: Realize that you don't HAVE to do anal for anyone. If you want to, then by all means, continue on. Never think that you have to do something for someone else though.
Step Two: Do as much reading and research as you need to feel ready. Look up different lubes, different toys, different positions for your first time. I personally recommend Maximus for anal play, but you should always check the ingredients to make sure it's something you won't have a reaction to.
Step Three: Find some privacy, turn on some calming music, and have a drink (hot tea, a glass of wine, whatever...just not too much. You want to feel your body's reactions.) and just relax.
Step Four: Consider playing with yourself in other ways to get in the mood. Ladies, if it takes some smoldering literature and your favorite vibe to get you in the mood, then by all means go for it. Men, if you want to watch your favorite scene (or if literature is your thing too...I'm not one to judge) do what you need to do to get aroused.
Step Five: Lube. Use more than you think you need, but don't go overboard.
Step Six: If you are starting with a finger (trim those nails, or wear a glove with cotton balls over the nails), then lube it up some too. If you are starting out with a toy (or going straight for a real cock), lube it up some too.
Step Seven: Take your time rubbing and pressing lightly against your asshole. Stay calm. Stay relaxed.
Step Eight: When you are ready, push your "stimulator" in slowly. Stop if it hurts, and go back to step 7. If you can get it all the way in without pain, continue to step 9.
Step Nine: Start playing as you wish, but slowly. There's no rush, and you certainly wouldn't want to hurt yourself. Pay attention to how your body responds. If you are with a partner, let them know how it feels. Tell them what you need. If at any time you need to stop, say so. Partners: If you enjoy getting to play with their ass, respect their wishes when they say to stop.
Step Ten: Enjoy yourself. What you do sexually is only the business of you and those you choose to share your sexuality with. If you want to experiment with different things, by all means, do so...but be safe.
Remember:Sex isn't nasty, and neither is anal play. If you really want to have anal sex or enjoy the pleasure it is capable of providing, then take your time and get familiar with your body.