Guide To Anal Sex For Beginners Without Pain

anal sex for beginners

Congratulations! You are on the way to mind-blowing orgasms. This guide to anal sex for beginners is here to help you out starting this magical journey without any pain.

Everyone is having anal sex!  Well maybe not your mom, but statistics show that at least 37 percent of all U.S. women and men are reported either lifetime anal sex practices or had recent anal adventure within the last year. More than a third of the entire population is impressive! So what are you waiting for? Read this guide to anal sex for beginners and start exploring new dimensions of sex.

Credit the social acceptance to more TV and movies talking about it, magazine articles, and of course, the millennial generation who has no qualms about eating ass.  Anal is not such a taboo subject anymore, especially since so much information has been spread about how to make it safe, pleasurable, and hygienic.  You can experiment with anal as a couple or even by yourself, to intensify your so-so masturbation sessions.

But it’s important to remember that there’s an entire process to having anal sex for the first time and it’s not as “simple” as you might think.

In this 10 Step Guide To Anal Sex For Beginners, we’re going to show you not only how to have anal sex for the first time but also how to do it without pain.

First of all, never just shove anything up your anus, regardless of whether you’re a man or a woman.  There is an entire process you must follow to experience the maximum benefit of an anal orgasm.

Let’s start with the basics and review how to approach your first anal experience in a way that’s pleasing and doesn’t wind up being a pain in the ass!

  1. Stay clean!

anal cleansing

Nervous feelings about anal being dirty will end up ruining the experience for you. Anal sex feels dirty if you don’t prepare!  Preparing involves:

  • Using the bathroom
  • Showering and scrubbing (get rid of any icky fecal matter)
  • Cleaning all toys after use – never reuse toys or go from ass to vagina, because of a risk of infection
  • You don’t need an enema but for the first time, if you’re paranoid about cleanliness it might help
  • Putting a towel down so you don’t have to worry about a mess
  • Wearing a condom is not required but it is a good idea, to avoid infection
  1. Relax (this step is really important for all beginners into anal sex)

The next step is to focus on relaxation.  You never want to start with “bigger”, or go for hard and fast.  The anus is simply not built for it.  In fact, relaxing before anal stimulation is crucial because tenseness equals TIGHTNESS.  And while that might be nice for a partner, that can hurt like hell for you if it’s your first time.

Relaxing involves DEEP BREATHING (taking a deep inhale, holding your breath, and then exhaling), relaxing your whole body, meditating, and concentrating on relaxing feelings.  It will require you clear your schedule for the next few hours so that you’re not distracted.

Even when you are entirely relaxed, focus on releasing the tension in your anal sphincter.  This means you “let go” of the tension, the opposite of contracting.  Like the feeling you get when you’re about to poop.

  1. Slowly progress into anal foreplay before any penetration.

If you’re with a partner, it’s usually better to focus on breast, buttcheek, or genital foreplay for several minutes before starting with anal foreplay.  This not only relaxes you, it helps prepare your body for a new kind of erotic sensation.  Going into anal “cold” without warm-up will only keep you in a tense state.

Once your partner is ready, they can try these anal foreplay activities:

  • Butt massage
  • Kissing the crack of the butt, teasing just around the anus
  • Kissing or licking the anus without penetrating
  • Tonguing the anus, just barely penetrating

You can do these foreplay activities with a partner or on your own:

  • Lightly rubbing a lubed finger over the anus
  • Or up and down the crack and perineum
  • Just barely grazing or softly penetrating the anus with a lubed finger

fingers for anal sex

  1. Insert a well-lubed finger first.

Before trying a penis or a toy, go with a finger.  Make sure the fingernail is trimmed and filed.  Make sure your finger(s) are extremely lubricated since the anus doesn’t get wet like a vagina.  Even if you think you’re using too much lube, you’re definitely not. Lubricant is your friend when preparing for anal exploration.

Start inserting by half inches, or even centimeters, not all at once.  Get used to the feeling and go slow to avoid damaging the sensitive tissue inside.

  1. Learn to communicate with your partner.

If you’re experimenting with a partner it is vital to communicate with him or her during anal foreplay and later penetration.  The “receiver” needs to communicate what feels good and what is discomforting.  The giver has to be attentive.  The more the giver assumes that the receiver likes it, the more painful it might be.

Some sex therapists have even suggested that both partners should experience anal penetration so they will understand what feels good and what doesn’t.

When it comes to finger penetration, experimentation is everything.  Either the giving partner (or if you’re going at it solo) will experiment with different pressures, rubbing different shapes, touching the walls, and discovering a combination that feels good.  Usually, it’s NOT just a few strokes.  You have to figure out the right series of movements to bring about an orgasm.

(Men can orgasm from prostate massage alone; some women can orgasm from anal, or enhance their clitoral/G-spot orgasm with anal play)

If finger penetration hurts, stop immediately.  You might need to add more lube.  Anal stimulation might feel weird or intimidating at first.  Some people describe it as an urge to pee, or the feeling of passing poop, or just a strong internal pressure.  As long as it doesn’t HURT, just let it happen.  Focus on relaxing and calming your muscles.

If it ever hurts, it’s because the pressure is too intense or the area is too tight.  This causes anal fissures, which are tiny tears in the surrounding tissue.  This is why it’s important to not only start with small, very thin penetration (like a finger or a very small anal toy) but also that you “stretch” your anus so that you can COMFORTABLY fit a larger object over time.

  1. Carefully choose a sex toy that’s designed for anal

silicone anal trainer kit

All anal toys have a flared base so they won’t get “sucked in” to the anus after repeated penetration. Unlike the vagina, toys without a flared base are easily lost inside and you would literally have to go get the toy removed in an Emergency Room.  Yikes!

safe butt plugs

T-bar shape allows for long-term and more comfortable wear while also protecting against going in too deep without a flared base.

It will actually take a few different toys to properly stretch your anus for full penis or large toy insertion.  And the “stretching” process will take months, not days or hours.

For the best results, start with a butt plug toy that’s almost-finger size in diameter, about 1 inch or 1.25 inches. Use the toy as you might use your finger, experimenting with how it feels and only stretching your hole a tiny bit at a time.  Remember to always use lots of lube!

If you’re ready to “expand” go up by 1 inch or even a half-inch in circumference at a time, which is .25 to 0.30 in diameter.  Use butt plugs at first, since they’re designed to be beginner’s toys.  Dildos are more realistically shaped and feel bigger, so if you advance to a dildo, make sure they’re slightly smaller than a butt plug so you can get used to feeling one deep inside you.

  1. All anal sex beginners need to expand or stretch anus over time so penetration won’t be painful.

You have the option of expanding your anus over time rather than just during sex – which is why butt plugs are designed to stay inside the anus and rectum for hours at a time.  Wearing smaller plugs for a longer period of time will allow you to more easily transition over to a larger toy – eventually a dildo, and eventually a partner’s penis.

In general, women usually need the lengthening process more than men, since the man’s prostate gland is only 2-3 inches in and upwards, whereas a woman’s erogenous zones, with indirect contact against the rectal wall) are farther back.

There’s not necessarily a need to stretch or wear a butt-plug if you don’t want to.  But it will help make penetration more comfortable in the long-run.  Remember increasing the duration of your butt plug use is important as you will gradually making it able to insert thicker plug or dildo.


  1. Stretch your rectum AND your sphincter

astretching anus

Not everyone realizes how important it is to gradually stretch one’s sphincters, as well as the rectum if you’re really going to explore deeper anal.  All anal sex beginners should stretch their rectum and sphincter really slow! This way, penetration is much easier.  The sphincters are tighter than the rest of the rectum, and tight means the opposite of relaxed and usually painful.

What did we learn about tightness?  That’s more likely to cause pain!  This is why there is a special need to “trade up” to wider toys over time and not simply stick to slimmer toys or even large bulb toys that still have slim tails.  Relaxing your ass and stretching it without pain is the priority.

  1. Start with the tip of the penis

After becoming experienced with wider toys and dildos, you will be ready for a partner’s penis or a strap-on if you prefer.  Use even more lubricant than normal for penetration, since thrusting will use up small squirts of lube quickly.

The head of the penis is the widest part so this is why stretching is important.  Once you can comfortably and SLOWLY take a penis, you will notice that the shaft is slimmer and won’t feel as large.

Even if you’ve done those stretches it’s still important to relax and learn how to “bear down” (as in taking a poop) so that you’re relaxing your sphincter muscles.  This allows his penis or strap on to penetrate with less tightness and less pain.

Just as you experimented with the toy and finger, have your partner experiment with different strokes and slow thrusting.  It should be a long while before you can take it fast and firmer.  If and when that ever happens!  You have to prepare for it and gradually work your way up to that, if you want to avoid pain.

While you experiment with anal, don’t neglect other erogenous zones of the body, like clitoral, vaginal, G-spot and breast stimulation.  It’s actually more difficult for women to orgasm anally than men.

Men can directly stimulate their prostate gland, but women can only orgasm anally because of indirect contact – against the G-spot, or the deeper A-spot, or the adjacent O-spot, that are close to the front and back walls that divide the vagina and rectum.

  1. Experiment freely and find the position that suits you

Different positions might provide different anal experiences.  You can change the way it feels by:

  • Lying on your stomach
  • Going doggy-style
  • Missionary
  • Side by side
  • Your partner straddling you
  • Your partner on top, or on top and reverse

As all anal sex beginners, you need to choose a position where you or your partner can easily control the speed and pressure of penetration. If the giver slips, it’s too much penetration too soon and could be painful.

There is no requirement to orgasm, or even for your male partner to orgasm.  Get used to the sensation before you start playing too rough.  It might take a few sessions to reach that point of comfort.

Last but not least, don’t worry yourself too much about “queefs”.  They are not farts, but actually the natural sounds of air escaping a somewhat tight and wet orifice.  It’s completely natural and not at all a buzz kill.  It should sexy, funny and awesome if it happens.

In conclusion, anal sex can be very enjoyable and will give you new and improved orgasms, a brand new sexual experience that’s worth the time and effort.

Just make sure you and your partner understand:

  • Get clean and focus on relaxing
  • Be slow and gentle in the beginning, mixing regular stimulation with light anal foreplay
  • Always use lots of lube
  • Gradually stretch your anus over time using very conservative butt plug toys – then gradually increase them in diameter
  • Take anal penetration very slow and very wet, always communicating with your partner as you both find the “combination” that leads to anal

Anal sex is very enjoyable if you are prepared to try it and invest some time learning the full process.  You might not get it the first time or the second time.  But if you make it a full journey, with a view towards discovery and patience, you won’t be disappointed.