You have used your friendly fingers and explored all of the fun things that anal toys have to offer.  You have become well acquainted with anal play.  You stocked up on the lube and through lots of communication you have both decided that the big day has arrived: you are going to have anal sex.  (Did you miss Part 1 and Part 2?)

First things first: Cleanliness.  It is a good idea to “take care of your business” when you know that anal pleasures are in store.  Shower and be thorough about it.  Special surprises may make you both feel a little uncomfortable.  Some people prefer to use enemas.  Do not use an enema right before you engage in anal play or intercourse.  Give yourself plenty of time for the enema to work its magic.  As a side note, if “special surprises” do occur, try to remain calm.  No one likes to feel embarrassed, especially during play time!   

You don’t just start off with full on anal intercourse.  This is a special occasion so go ahead and set the mood.  Make sure your house or apartment is at a comfortable temperature.  It is hard to get in the mood for any type of play when you are covered in goose bumps or dripping with perspiration.  I am a firm believer in creating the atmosphere that suites your personality and turns you on.  If you enjoy soft music and candles, then by all means light em’ up and get your Yani on.  However, that may not tickle your fancy.  If punk rock and bright lights get you going, then turn them up! 

Foreplay is always important.  Do the things you do that get each other all hot and bothered.  Make out, undress each other, massage each other or dress up in giant bunny costumes.  You get the point.  Since the penultimate act of anal sex is in store, use the lessons you learned in Part 1 and 2 to get you there.  Use a lot of lube, tickle her back door, get your fingers involved and spend some time with her favorite butt plug or anal dildo.  This will get her in the mood and ensure that she is warmed up.

Condoms!  Do I really have to say more?  Play it safe and wrap it up!

There are other safety precautions you must take here as well.  Never ever go from the anus to the vagina during anal sex or any other type of anal play.  This can cause infections and irritations!  Wash and change condoms before switching playgrounds.  This is true for any type of anal play.

While you may imagine the skies opening up, angles singing and flurries of iridescent glitter falling from the sky as you engage in mad passionate anal sex, that isn’t quite the case.  Take it is easy and go slow.  Make sure she is in a comfortable position that will allow her to relax.  This may take experimentation at first.  Some women prefer to be on top in the cowgirl position so they can control the level of penetration.  Others prefer to lie flat on their stomachs.  Perhaps it is not the most romantic of all positions, but may be a good start. 

Remember to breathe!  Holding your breath will only tighten your sphincter muscles and makes insertion painful.  Breathing is your friend – with that whole oxygen thing going on and whatnot.  It is a good idea to continue with vaginal stimulation when you are diving into anal sex.  Women may stimulate themselves with a vibrator or their hands, or they may enjoy their partner doing it for them.  The extra stimulation can produce ultra-orgasmic results!  Enjoy your anal sex session and continue to experiment.  This is only the beginning of what so many consider taboo.  Many people are curious about it and love it.  Follow the right path and it can be yours to behold!

If it is painful, then she’s just not ready.  Don’t push her; move on to other fun play time activities.  You can always try again when you are both ready.  It will only get better with time.

Would you like to receive your anal education through DVD?  Check out Tristan Taormino’s Expert Guide To Anal Sex.  While you’re at it, check out the awesome butt plug that she designed! 

So, your fingers have had their fun with the discovery of the anal treasures; booty, if you will.  You still are not quite ready for full on anal sex, but you are ready for the next step: toys.  Butt plugs, anal beads and dildos oh my!  Sex toys are fun all by themselves, but are great for continuing your journey towards butt sex.

Now don’t go all willy nilly and grab the first dildo you see as you head straight for the back door.  As always, safety first and don’t forget what you learned in Part 1. (Click here to move on to Part 3)

Anal Sex Toy Safety

As you read in Part 1, have plenty of lube on hand and use lots of it.  Waterbased personal lubricant is a good choice because it plays nicely with all materials.  Look for one that is formulated for anal sex for a more lube-a-riffic time.  Silicone lube eats through silicone toys, plain and simple.

ONLY use anal toys that have a FLARED BASE or a RETRIEVAL CHORD!  There are no exceptions to this rule.  Unless you want a really embarrassing trip to the ER, you’re going to want to follow this one.  Rebel elsewhere.

The flared base ensures that the butt plug or dildo will not enter further into the anus than desired.  By this I mean it won’t disappear inside your butt.  The sphincter muscle is semi-involuntary.  With one random flex, a toy without a flared base can get sucked up and lost inside of your colon.  Yikes!

As with all sex toys, it is best to use nonporous, hypoallergenic, phthalate free toys.  Materials like silicone, aluminum, glass and even wood are safe to use on the body and can be cleaned easily.  Porous materials like jelly hold on to bacteria which can cause problems the next time you use the toy.  If you have a toy you absolutely love that is made out of porous materials, put a condom over it when using!

As with fingernails, smooth or file down and rough seems or edges on the toy.  Even the tiniest bit of sharpness can feel like a razor during anal play.  The lining of the rectum is quite delicate.

Again, never ever ever ever use a toy in, on or around the vagina that was just used for anal play unless you have seriously cleaned it FIRST!  Who likes infections?  Same goes for anal sex!  If you want to travel back and forth between the vagina and anus, put multiple condoms over the toy and remove one before switching to the other play ground.

Lube? Yep. Flared base? Got it.  The right materials?  Yes.  No switching between playgrounds without proper precautions! Okay!

Silicone butt plug: great for anal beginners!

Butt Plugs

Butt Plugs are great for moving beyond the fingers while on your journey towards anal sex.  You stick them in and they stay there.  They stretch the anus and give a nice filled feeling.  They can be worn during ply time, intercourse or just while you are washing the dishes or lounging around the house.  They can intensify your orgasm as the muscles tighten around the butt plug and send you straight to the moon.  In addition to a flared base, they generally have a smaller slender “neck” for the anus to hold on to, a wider shaft and then they taper again.  Shapes vary a bit, but the sizes vary a great deal.  Start small and slowly work your way up in size.

Anal Dildos

“Anal Dildos are designed specifically for anal play, using flared bases and retrieval mechanisms to facilitate safe anal play.”  You may be asking, “What is the difference between a regular old dildo and an anal dildo?”  Well, some dildos are designed with the shape of the rectum in mind and follow the contours of the back entry way.  Sizes and shapes vary greatly.  However, you can use most dildos anally as long as the flared base is present.  These toys are great for introducing and getting used to the thrusting motion that comes with anal sex, opposed to the butt plug which stays in place.  Start with a dildo that is less than 1 inch in width.  Don’t thrust too deep at first.  Take it easy or you won’t enjoy it and you will never get to the pot of anal gold!  By the way, a set of balls on the dildo does count as a flared base.

Anal Vibrators

Anal vibrators are often anal dildos, probes or butt plugs with a motor.  They may come with a removable bullet so you can choose whether or not you want buzz in your booty.  This also makes cleaning easier.  You don’t have to worry about ruining the vibration mechanism by submersing in water and you can sterilize all of the nooks and crannies.  Vibration can feel wondrous inside of the rear end.  Some like to tease the little back door opening with the vibration before inserting.  The sensation may also transfer to the genitals which many find to be incredibly thrilling.

Anal Beads

Adorable Anal Beads

While anal beads may not be considered essential when preparing for anal sex, they are certainly worth the discussion when it comes to anal play.  Anal beads are a set of beads connected by a string, often nylon, or a “stick” made of the same material as the beads themselves.  The beads may graduate in size, or they may all be the same size.  Bead sizes and cord lengths vary.  They are often made from, but not limited to, hard plastic, jelly or silicone.  Beads connected by the stick, especially silicone, are easier to clean and sterilize.  Unwanted bacteria and substances may hold on to a soft cord or porous bead material.  One downfall of the plastic beads is that each bead is usually comprised of two halves stuck together, which in turn gives you a seam: a rough, mean and painful seam!  Avoid them, or file them down.

Here is where the magic happens: Gently insert each bead into the anus at the beginning or midway through your adult play time.  Just before or at the exact moment of orgasm hold on to the end of the string and pull the beads out.  Some prefer a slow gradual pull; others prefer to feel a rapid succession of beads as they exit.  This gives brain melting, leg cramping, tear jerking orgasms to women and men.  Try it.  You will probably love it.

Get your anal play on and explore all of these toys.  You can try them out by yourself and find fun new ways to masturbate.  You can call it solo play time if it makes you feel better about it.   You can also try them with a partner and find new ways to stimulate each other.  Let these adult products work you up to hot anal sex fun, or just enjoy them for what they are.  Anal toys may not be for you, but like mom always said, “How will you know until you try?”

Click for Part 2 and Part 3!

Are you anally interested?  Ready to open your back door for business?  Does anal sex excite you and frighten you all at the same time?  Well, I am here to help.

You can’t go “all in” right away.  Warm up is important.  It is a good idea to start with anal play involving lots of lube, fingers and toys.  Calm your eager partner, and remind them this should be and can be enjoyed by the both of you.  Have them read this with you.  Not only will these suggestions get you ready to take the anal plunge, they will add to your adult play time repertoire of activities.

Lube it or lose it.

Awesome waterbased anal lube!

Make sure you have a full supply of lube.  Unlike the vagina, the anus does not naturally produce moisture.  If you don’t use a lubricant, you could cause serious damage to your rear end.  You don’t want the word “tear” to be associated with anything that has to do with anal sex.  Ouch!  Waterbased personal lubricant is always a good choice.  It is safe to use with condoms and sex toys (it won’t eat through them).  It does absorb into the skin quickly, so keep it close by so you can reapply with ease.  Some lubes are specially formulated for anal sex and may give you a little more slip.  You can find lots of lube here.

Relax.

Get in a comfortable position that doesn’t require your muscles to do too much work.  Don’t clinch your butt cheeks; this is not the time to get your kegal exercises in.  Breathe continuously and allow your body to let go of any tension.  Tight rectal muscles will only make anal play and anal sex difficult and painful.

Friendly fingers.

Ask any anal aficionado and they will tell you that using a finger is the best way to get acquainted with anal sex.  First of all, the finger-er should wash their hands and the finger-ee should wash their bum.  Be sure to trim your finger nails and file any rough edges.  A sharp nail can easily tear the thin lining of the rectum, even through protective covering. Again, ouch!  To keep things hygienic, you can use a finger cot (finger condom) or a latex glove.  Many ladies out there have latex allergies, therefore latex free nitrile gloves are a great alternative.  Just apply the personal lubricant to the glove or finger condom and you will have a nice satisfying slippery finger to work with. 

Start slow! 

Massage: intimate and relaxing.

Tickle the outside of the anus by gently sliding your finger up and down over the little pucker.  It feels great and helps the rectal muscles to relax.  Since these muscles are semi-involuntary, the opening to the tunnel of mystery and splendor will begin to wink at you.  Eventually, it is time for the finger to gently slide in, still relaxing.  Pay attention to the receiver’s body language.  You will be able to tell if she loves it or if it is uncomfortable.  If not, just ask.  If she isn’t enjoying the use of your finger, she probably won’t enjoy anal sex.  Communicate and ask what could make this anal endeavor better.  If she is loving it, keep up the good work.  Vaginal oral sex in addition to anal play just might make her lose her mind!  Just a suggestion.

If the receiver absolutely does not like it they should absolutely stand their ground and the giver should absolutely not push it!      

Never ever ever ever go from the anus to the vagina without washing your hands, toy or penis first!  Even if you washed your hands before play time, wash them again before moving on to the vagina.  Not doing so can and will likely cause infection and irritation.  You have been warned!

Now you are off to a good start.  Lube up, trim up, wash up and enjoy your first anal journey.  Come back next week and we shall discuss fun toys like butt plugs and anal dildos.  Anal sex shall be yours to behold!