First Anal Try? Here’s How to Train for Anal Sex

Last Updated on December 29, 2022 by Chris Thompson

So you want to try anal sex.  You’ve heard stories about it, read about it, and maybe even had secret fantasies about it.  As an anal virgin you are curious, maybe a bit fearful, and wondering what it’s all about.

We are taught as children that the anus is a dirty, secret place and many of us carry those taboos with us into adulthood.  But, the anus is a very sensitive area, and, when given the proper attention, can bring one to a whole new level of ecstasy.

For men, the anus is the gateway to the prostate, a very sensitive area that many men may achieve orgasm from when stimulated.

Anal expert, Tristan Taormino notes that the “anus, anal canal, and rectum are wonderfully erogenous zones, rich in nerve endings and super-sensitive to stimulation and penetration. At the right angle, many women find that you can indirectly stimulate the G-spot through anal penetration.”

Many sex experts recommend that you arouse yourself in the regular ways, until you are good and hot before attempting anal play and to continue stimulation throughout.

The most important thing to consider with trying anal sex with a partner for the first time is that the person being penetrated is the one in charge.  Communication is essential with any type of sex play and even more so for anal play.

It is important to go slow, get fully aroused, use plenty of the best lube for anal (and then some), and to listen to your partner’s needs and body language. Because the anus has a very thin lining it is important to be careful not to tear it and to use condoms for safe sex purposes. Always stop if you experience pain or discomfort.

Better First Time Anal Sex Tips & Techniques

Tip # 1:  Overcoming Stigmas

Many couples find even discussing anal sex to be uncomfortable, never mind their thoughts of how it might feel to actually do. Open communication is imperative to any healthy relationship, however.

Remember that stigmas attached to anal sex come from a simple lack of knowledge; we often fear what we don’t know.

A woman’s biggest fear may be that anal intercourse will be painful. Whereas a man might worry that being penetrated will somehow make him less than masculine. Both these worries are normal, but not necessarily the case.

Anal sex does not have to be painful if done properly. And men’s enjoyment of it not only doesn’t emasculate him, it indicates he is a broadly sexual being, capable of enjoying all sorts of pleasure. In truth, the anus is simply an erogenous zone like any other. By learning more about anal sex you and your partner can educate yourselves and broaden your sexual horizons.

Tip # 2:  Anal Anatomy

The entry to the anus is the puckered circle of skin behind the vaginal opening on women, and behind the scrotum on men. The anal canal itself is only about one inch long and leads to the rectum, which is approximately 8-9 inches long.

The highest concentration of nerve endings is around the anal opening. You can use a finger or tongue to focus on these. For many, this is more than enough stimulation.

However, when an object or penis is inserted beyond the anal opening into the rectum, other pleasurable sensations are experienced. The outer portion of the rectum, like the vagina, has several nerve endings. The inner portion responds mostly to pressure.

Tip # 3:  How To Start

If you have never investigated your own potential for anal pleasure, a good way to start is on your own, rather than with a partner. You may wish to take a warm bath or shower. Clean the area well. Once you have done this, relax and take a moment to touch the area with a finger or two.

Apply different types of pressure to your anus to discover where you feel sensation most. You may wish to insert a finger into your anus a small amount at a time. (Be sure you have proper lubrication to ensure an easy movement; you should never force anything into the anus.)

Pay attention to your body’s instinctive reaction. Your sphincter may “clamp down” and squeeze your finger. This is normal. Simply stop moving and concentrate on relaxing your sphincter. Practicing on your own will allow you to be more comfortable if you choose to try anal sex with your partner.

The best way to try anal sex for the first time is through masturbation. That way you are really in control and can decide how big, how far and how fast on your own.  Self-exploration is important as it allows you to discover what feels best and how your body responds.  You also don’t have the pressure of performing or trying to satisfy your partner’s needs.

Warming Up: The Rosebud of Pleasure

Developed by a massage therapist and sex educator Joseph Kramer, this is a good way to begin exploring anal pleasure.  First, begin with massaging your buttocks to get the blood flowing. Try squeezing your cheeks with your fingers, raking your fingernails over your ass, and even slapping it.

Slowly begin to clench and unclench the asshole. Next, lube your finger very well and rub the pad of your finger around the anal rim, exploring the sensitive rosebud. Lube up the crack and slide your hand up and down.  Finally, when you feel ready, you can insert a finger into the sphincter, gently stretching it and massage the silky skin inside.

It is also recommended to stimulate other areas of your body as you would naturally, to get yourself good and aroused.

Tip # 4:  Safe Anal Sex

Now that you’ve experienced a bit of solo play, it’s time to try out your new found passion with your partner.  Both men and women enjoy the experience of anal sex with a partner, no matter if you are GLBT or straight.  Most important is who is in control.  The partner being penetrated should always be in control of the pace and degree of penetration.

Anal sex is not supposed to hurt and if it does you are perhaps not ready or doing it wrong.  To avoid hurting your partner, make sure that you both communicate with each other.  “Mmmm, that feels good,” “More…”, “Back up a bit,” whatever works for you.

There are a few very important rules to follow to keep all anal play safe and healthy. First: be sure both you and your partner have cleaned thoroughly. This includes not only our bodies themselves but any toys that may be incorporated into the anal sex experience.

Always use enough lubrication to ensure easy entry into the anus. A general rule is that larger the object being inserted, the more lube you’ll need.

Never under any circumstances place your penis or any toy that has been in an anus directly into a mouth, vagina, or anus. You must wash thoroughly to avoid any bacteria from traveling to these areas. A generally safe bet is to use a condom during anal sex. This makes for easier clean-up and, of course, decreases the chance of spreading STDs.

Tip # 5:  Oral-Anal Sex

Popularly called “rimming,” oral-anal sex involves orally stimulating the anus with the mouth and/or tongue. This can be highly pleasurable, particularly for those who are only comfortable with outer stimulation of this area.

Because the tongue is softer than a finger, your partner may better enjoy the sensations of this kind of stimulation.

Be sure, as always, that the area is clean before you begin. Oral-anal sex is most often practiced as part of oral sex. Couples can actually perform this kind of stimulation on each other in the “69” position as well. This is another way to share pleasure as well as a bonding experience between mates.

Tip #6: Sex Toys for Anal Play

There are a large variety of sex toys available for anal play.  These include butt plugs, anal beads, anal vibrators, prostate stimulators, and anal dildos.  They all have different purposes and will give your body different types of pleasure.

Butt plugs have a narrow head and flared base. They are generally used for anal training, starting from small and slim, to allow you to get used to having something in your anus. These are inserted and then stay in place for as long as you want to keep them there. Tantus makes a whole line of excellent butt plugs called Flirts in various sizes all made of medical grade silicone.

Anal vibrators and dildos are more for stroking penetration, similar to regular penile sex play with a partner.  They can often be used on a harness for lesbian penetrative sex and bend-over-boyfriends.

The Rude-Boy prostate stimulator is a great toy for men who want to try a bit of buzz, while the Vivid Red Hots Briana Vibe is a good choice for women.

Prostate stimulators like the Aneros are used to put pressure against the male prostate and are used in a rocking motion rather than in and out.

The male prostate is an area of immense pleasure and will often lead to intense orgasms when stimulated.  Anal beads, like the Bendybeads by Fun Factory, are one of the most non-threatening ways to begin anal adventures for anal virgins and can be used simultaneously with vaginal penetration or clitoral stimulation.  They are inserted one by one and then gently pulled out.

Any anal toy should have a wide base or a retrieval ring so the toy is easily removed.  When first exploring anal play it is important to start small and work your way up to larger sizes.  The most important “toy” for anal play is lubricant!  This cannot be stressed enough.  If you want to have a healthy, happy experience with anal play use lots of lube.  Good ones to try are Moist Anal Lube and Adam and Eve Anal Lube.

Tip #7: First Time Anal Insertion

Like the vagina, the anus can also receive enormous pleasure from the insertion of fingers or toys. Start small, using a fingertip after you have stimulated the rosebud for a while, making sure to use lots of lubrication.

If your fingertip feels good you may want to insert the entire length of the finger, or even try two.  After a while, your anus will get more used to the feeling of fullness and you can try larger toys like slim butt plugs, anal beads, and anal dildos.

At first, anal play will feel strange and you will most likely want to push what is entering back out.  This is, after all, a natural reaction.  If you relax into it, however, anal insertion can be a wonderful experience that can intensify sexual play and orgasm.

Many people worry about the mess during or after anal play.  Be sure to empty your bowels before anal play.  You can also choose to flush yourself out with an anal douche about an hour before play.

I found it much easier to enjoy anal play in the bathtub with toys designed for underwater fun.  It allows you to focus more on the pleasure and sensation, instead of worrying about messy accidents.  Also, a warm bath will help you relax, which is essential for anal play.

First Time Anal Sex Do’s and Don’ts

Anal Do’s

•    Clean yourself and your toys.
•    Use a condom or latex gloves.
•    Trim nails of rough edges.
•    Relax, breath & take it slow.
•    Use lots of lube. I mean lots.
•    Stop if there is pain.
•    Only use toys with a flared base designed for anal play.

Anal Don’ts

•    Insert toys in the anus then the vagina as it may cause infection.
•    Insert sharp or foreign objects or anything too big.
•    Do it if you really don’t want it.
•    Hurry or force it.
•    Pressure your partner into it if they are not ready.