Tips for Your First Time Having Anal Sex

By Dr. Josh Sex Tips

It is often said that you never forget your first time having sex, but that rarely refers to your first time having anal sex.  Perhaps that is because for far too long, anal sex has been considered taboo, something to be ashamed of, or at least to stay quiet about.  Losing your anal virginity should be just as important as the first time you popped your proverbial cherry.

Anal sex is starting to go mainstream.  It’s not just a “gay thing” anymore, but something that people from all walks of life, all sexual orientations, and all gender identities are starting to explore more commonly.  For example, a 2015 study found that 36.3% of heterosexual US women engaged in anal intercourse at some point in their lifetime (Benson).  So, join the club, and let me take you on a journey into how to best explore your backside during sex.

Now if you’re new to this anal game, it can seem intimidating.  Apprehension is common, but rest assured that anal sex can be absolutely fantastic and orgasmic when done right.  A lot of this has to do with our anatomy.  The internal and external anal sphincters are rich in nerve endings.  Many of these nerve endings are most abundant around the anal opening, but the outermost part of the rectum also has them.  In individuals with a prostate, the pleasure from anal penetration can be especially powerful as this arousable gland is readily excited through the rectal wall.  In folks with a vagina, anal penetration can put pressure on the wall between the anus and the vagina, which can stimulate the G-spot and clitoris.  For those penetrating their partners, the sensation on the penis by the anus can be noticeably more intense than the vagina.  The anus is less elastic and provides a tighter feeling, which can provide greater stimulation than penovaginal intercourse.  So anal sex is basically a win-win for everyone!

Now it’s time to put that anatomy to work.  What follows is a step-by-step guide on how to maximize your first anal experience.

Step 1: Practice

Unlike, say, learning how to swim, I would not recommend simply jumping into anal sex.  Figuring out what feels good on your own is an important step in taking the anal plunge with your partner.  Start slow.  Try touching, rubbing, and even lightly penetrating your anus with a finger or a small sex toy, and work your way up from there.  Breathe.  If you relax and breathe, you can increase the pleasurable sensations from anal exploration.  Most of the time our sphincter muscles are clenched.  To prepare for anal sex we have to train them to relax, so don’t rush the process.  Butt plugs and other toys come in various sizes and many adult toy companies offer anal training sets.  Take advantage of these and start to explore your backside.  Trust me, it will make anal play with your partner that much more orgasmic.


Step 2: Communicate

If you’re interested in exploring anal sex, either as a giver or receiver, be upfront with your partner.  Don’t beat around the bush!  For some, this conversation may sound awkward, but it’s important to make sure you and your partner are on the same page.  Broach the topic with your partner as a way for you to enhance sexual pleasure together.  This is a new adventure for both of you.  Use the conversation to discuss concerns, anxieties, or past anal experiences that may or may not have worked.  When you involve your partner, the possibilities are endless and will make for a much more satisfying experience.

Communication during the anal act is equally important.  Give your partner feedback on what you want.  Go slower.  Go faster.  That feels great.  Gimme a second.  These are all helpful and cue your partner into what feels good and what doesn’t.  Some couples even come up with a “safe word” that helps facilitate communication without ruining the moment.


Step 3: Play safe

Like with other types of intercourse, you should definitely consider using a condom before engaging in anal sex to reduce your risk of sexually transmitted infections (STI) and HIV. Peno-anal penetration without a condom is considered one of the riskiest forms of sexual activity.

Also look out for potential injuries.  Bleeding during anal sex, while not uncommon, is not normal.  Mild discomfort, especially when you’re first starting out, is also common but persistent pain with anal sex is not normal either.  If bleeding or pain occurs regularly, it may indicate a bigger problem. But don’t freak out! Try over-the-counter remedies like stool softeners, suppositories, or creams like Preparation H.  Abstain from additional anal sex until the problem stops.  If these issues don’t resolve, seek out medical advice.

Another way to play safe is to make sure you regularly clean your anal toys between use. Vaginal infections, like urinary transmitted and yeast infections can result from vigorous anal play, especially if toys are involved.  You should make sure to never have vaginal sex after anal sex to prevent contamination of the vagina with anorectal bacteria.  Regular toy cleaning is important if using between partners as well.  There are a variety of toy cleaners out there that can help keep everything fresh and clean.


Step 4: Stay ready

One of the most common misconceptions about anal sex is that it is inherently dirty.  This is primarily related to our sociocultural obsession with cleanliness when it comes to sex.  But sex of any kind can be messy.  And the truth is: the anus and rectum have very little fecal matter in them.  The body stores most of the dirty stuff in the colon with the rectum acting mostly as a quick exit passthrough.  That said, there is still a lot that can be done to make sure you’re ready to go come game time.

Preparation for the big event should start well before the bedroom and it’s all about diet.  Consuming a high amount of fiber or taking fiber supplements can make all the difference.  Some examples of high-fiber foods include legumes, vegetables (especially broccoli), leafy greens, berries and other fruits, avocado, whole grains, and unprocessed bran.  Our modern Western dietary habits can make consuming a healthy amount of fiber daily difficult.  Supplementing fiber can be as easy as taking an over-the-counter capsule or mixing fiber-rich powder with your favorite drink.  A diet high in fiber helps ensure complete evacuation of stool during bowel movements so there’s less mess to worry about when it comes time for anal play.  When you deliberately make fiber part of your daily regimen, cleaning before anal sex can involve simply using the bathroom and quickly rinsing off.

Some anal players prefer an extra deep clean beyond what fiber has to offer.  Many assume that anal douching is necessary before anal sex, but the anus has natural bacteria that fight infection and things stay relatively clean assuming regular hygienic practices.  Anal douching is a matter of preference, but one should consider a few facts before doing so regularly.  Douching too often can lead to irritation, mucosal injury, and disruption of the bacterial gut microbiome.  These detrimental effects from douching can lead to higher rates of STI and micro-traumas like anal tears (fissures) and hemorrhoids.  So douche at your own risk.

It’s not just your anus and rectum that should be clean.  Consider prepping your anal sex space also.  Grab a towel or a comfortable pillow.  A towel can help protect your bedding from the stains caused by the lubrication you will definitely need (see Step 5).  Placing a pillow under your lower back can also keep anal play more comfortable and give your partner better anal access.



Step 5: Lubricate

If there’s one thing you learn from this discussion it’s that there is no such thing as too much lube.  Unfortunately, the anus and rectum are not built to provide the same degree of lubrication as the vagina.  But that doesn’t mean you can’t add your own to keep things friction-free and enjoyable.

Steer clear of warming or cooling lubricants as they can be irritating to the anus and rectum.  If you’re considering warming up with a butt plug or sex toy, consider grabbing a toy-friendly lube, which can make all the difference.  And whichever lube you decide is best for you, never hesitate to reapply.  Adding lube throughout your anal adventure will ensure a more pleasurable experience.

Step 6: Switch positions

Not all sex positions are created equal.  And anal sex does not necessarily always mean penetration.  Some anal stimulation doesn’t involve penetration at all.  Rimming, or anilingus, which involves performing oral stimulation on your partner’s anus, can be especially arousing.  When you’re ready for penetration, find a position that gives you as much control as possible—like sitting on top of your partner.  Having your partner penetrate from behind can sometimes allow for easier insertion.  And starting off lying on your side and being spooned by your partner as they penetrate you is a good way to start if you’re new to the anal game.  Remember that when it comes to anal sex, think outside the box and do what feels good.

Before this anal guide comes to an end, I will leave you with a few points to remember:

  • Communication and preparation will set you up for success and give you the best shot at making the most of popping your anal cherry.
  • Anal play can be exciting and novel, but it’s not something you have to do. If you don’t like it after trying, that’s ok.  Or if you’re not interested in checking the anal box on your bucket list at all, that’s also ok.  Never feel pressured into engaging in anal.
  • While you’re engaging in anal play, don’t ignore your other erogenous zones. Anal sex can be even hotter when combined with clitoral stimulation, nipple play, or masturbation.  So incorporate your whole anatomy, not just your backside, into your anal exploration.

Benson LS, Martins SL, Whitaker AK. Correlates of Heterosexual Anal Intercourse among Women in the 2006-2010 National Survey of Family Growth. J Sex Med. 2015 Aug;12(8):1746-52. doi: 10.1111/jsm.12961. PMID: 26289541.