Does Anal Sex Hurt?

For those curious about exploring anal penetration for the first time, one big hurdle is the fear of discomfort. It’s a sensitive area, and it can be daunting trying to figure out where to begin for beginners. 

When it comes to anal sex, you may be wondering: 

  • Will it be messy?
  • Will it hurt?
  • Will it feel good?
  • How can I bring it up with my partner?
  • Is anal penetration only for gay men?

While anal sex can be uncomfortable, painful, or messy in some circumstances, it doesn’t have to be. Pain tolerance isn’t a necessary rite of passage when exploring your behind. Also, the belief that anal penetration is reserved for gay men is an all-too-common misconception. 

All humans with an anus can enjoy penetration, and those assigned male at birth have the added delight of prostate stimulation. People of all genders and sexual orientations alike can appreciate the sensations anal play offers. 

Anal sex can come with a variety of benefits, including:

  • Prostate stimulation (for those assigned male at birth)
  • No risk of pregnancy (for those assigned female at birth)
  • Intense orgasms
  • A new power dynamic with your partner

Let’s learn more with GIDDI! Here’s an extensive breakdown of the ins and outs of anal penetration. 

Talk It Over

Does Anal Sex Hurt?

If you’re diving in with a partner, communication is key. Like in other aspects of your relationship, it’s best to be candid and lay out your expectations, desires, and fears about the experience. It can be daunting to be so open, but it’s also gratifying.

Open communication will bring you closer and make you feel crucially supported. Anal penetration is a vulnerable and intimate act, and you want your partner in crime to be someone you trust. Let your partner know what you want and what you’re afraid of, and ask them to share these things, too.

Remember, talking about it doesn’t just happen once. Make sure to verbally check in with your partner before, during, and after a sexy session.

If you’re not sure how to start the conversation, here are some examples:

  • What turns you on about this experience?
  • What are you nervous about?
  • How does that feel?
  • Can I do anything differently?
  • Here’s something I really want to try…

Stay open-minded and take feedback from your partner with grace. This may be a learning experience for both of you!

Don’t Stress About The Mess

First and foremost, before engaging in anal play, it’s best to get as clean as possible. Showering with your partner is a great way to get in the mood while getting clean. 

Washing the anus thoroughly can also help decrease health risks from being unsanitary. 

You may have heard of anal douching, the practice of rinsing out your rectal cavity with water. While it’s an option, douching is not mandatory when engaging in anal play, and a thorough scrub in the shower is enough. Condoms can also be an easy way to keep the booty clean (and safe!). 

Grab the Lube

Does Anal Sex Hurt?

The anus does not naturally produce moisture as you’re getting in the mood. Lube is a necessary friend in the adventure of exploring anal play. And when it comes to using lube, the more, the merrier. 

Be more than generous when you whip out that bottle. Keeping the anal area (and the penetrating penis, toy, or prostate massager) well-lubricated can help ease discomfort during penetration by reducing potentially painful friction. 

Make sure you and your partner know that oil-based lubes (including vaseline and coconut oil) can dissolve condoms. While water-based lube is safe to use with condoms, it does dry up quickly and should be reapplied with generosity throughout the time you spend getting frisky.

Use a high-quality water-based lubricant, like our Wicked Jelle Water Based Anal Lube

Don’t just save lube for the main event (which could be the penetrating penis or strap-on in question). Use it from the time you begin exploring with any penetration. Remember: A lubed finger is far more pleasant than a dry one!

Warm Up the Bum

In life, it’s always best to build up to something before going all in. Your anus is no different. It needs some love before being full-on penetrated. 


Oral stimulation, also known as rimming, is a great way to warm up that area and get used to the sensation of anal penetration. The giver can begin by gently licking the area or circling it with their tongue. In contrast, the receiver can focus on relaxing and enjoying a sensation that might be entirely new for them. 

Once you’ve explored oral stimulation to your satisfaction, have the giving partner insert a (well-lubed) finger inside. Remember to go slowly and continue to check in with each other. This act will get the receiving partner used to the feeling of penetration and stimulate the prostate

You can find the prostate by performing the “come-hither” gesture. Once the fingers are in, think about moving the finger toward the belly button. You can also try circling your finger or pressing on the anus. Make sure the receiving partner is comfortable with the penetration of a finger before moving on to the next step.

Switching Up Positions

You can try several comfortable positions when exploring anal penetration, both with a partner or on your own. 

  • Face down: This position gives you better control of your sphincter. Lay down on your stomach and spread your legs. The downside is that you can’t see all the action. A great position to try when you’re more used to penetration. 
  • Legs-up: A classic position popular among beginners and veterans alike. Lay on your back and hug your thighs, exposing your anus. This gives you a good view of either yourself or your penetrating partner. 
  • Fetal position: An easy alternative to legs-up and a great position for focused prostate stimulation. Hug your knees to your chest, exposing your anus. 
  • Doggy style: This one is great with a trusty penetrating partner. But since you can’t see your partner or what’s going on, don’t forget to verbally check in with each other every step of the way!

What Is a Prostate?

Does Anal Sex Hurt?

A prostate is a walnut-sized gland that produces prostate fluid, one of the main ingredients of semen. Prostate muscles contract during orgasm to forcefully expel that fluid for ejaculation.

The prostate is present in those assigned male at birth (located below the bladder, in front of the rectum) and is full of nerve endings that respond to stimulation. When exploring your prostate solo via anal penetration, a prostate massager can help. 

Prostate massagers are sex toys meant to be inserted into the anus and (you guessed it) massage the prostate. They come in many shapes and sizes. Some vibrate, while others simulate a partner by thrusting. 

GIDDI has several options to get you started:

If you’re looking for something girthy with a variety of settings, check out the Thor Rotating Prostate Massager. It has three rotation speeds and 16 vibration modes, and has been awarded Best-in-Class by Gadget Review among the top prostate massagers.

If you want to include your penis in action, GIDDI’s Vulcan Vibrating Prostate Plug has two flexible rings: one to fit around the penis while the other wraps around the scrotum. These can help support erections for longer and delay climax. 

The anal plug included also vibrates and targets your prostate with direct stimulation while also giving the feeling of fullness. The Vulcan Prostate Plug can be used alone or with a partner. 

The ever-popular “come hither” motion is one sure to reach your prostate. GIDDI has something that can do just that.

The Tomo II Come Hither Prostate Massager is perfectly contoured to fit snugly inside you, giving the sensation of fullness. The motion strokes your prostate with pressure while the external head massages your perineum (the sensitive area between your anus and scrotum). 

This massager has nine powerful modes of vibration and is shaped for easy insertion. Great for first-timers, as well as the more experienced. 

Take Your Time

The potentially most important reminder to keep in you and your partner's mind throughout (or even while exploring alone) is this: take your time

When someone is eager to become comfortable with anal, or if they’re used to viewing porn in which initial penetration takes seconds, it can be easy to rush to the finish line. But this is never a good idea, especially for first-timers. 

Go slow, and continue to check in with your partner and yourself. Feel free to take breaks as needed. There is simply no rush, and the sensation of anal penetration can be a lot to get used to for someone new to the game. 

Going too fast and furious can result in discomfort, muscle tears, or tightening due to stress. You’ll have the most success when you take your time and prioritize your relaxation (which can also loosen the anus). Slow and steady wins the race!

But Still, Keep Going…

The most reliable way to get comfortable with anal penetration is repetition. If you enjoyed your first exploration (or even if you didn’t but haven’t lost hope), try, try again!

Like all sex acts, it can take a few (sometimes many) tries before you feel confident and in control. With a partner you trust, figuring out what works for you throughout several sessions together can be a great adventure.

Exploring can help you learn to trust and get to know yourself even better if you're alone. Have fun with it, and never push your body to do something that doesn’t feel right. Some days it might work out, and on others, your body might not be up for it.

Go with the flow, and don’t forget to go slow.

Get Ready for Booty Play

At the end of the day, you know your body best, and you’ll know what feels most comfortable at the moment. Now it’s time for you to go forth and explore! Take it slow, whether alone or with a partner, and simply enjoy getting to know your body and all its sensations!

To be sure that the lube stays on long and is thick enough for anal play, head to GIDDI and check out our shop. Be kind to your behind, friends!



Lube Dos and Don'ts | Healthy Horn U Texas 

Prostate Gland | PCF

50 Shades of Trust | Psychology Today

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