Anal beginner

First-Time Anal Too Painful for Your Partner? Here’s How to Help Them Enjoy It Next Time

Published: JANUARY 11, 2019 | Updated: NOVEMBER 13, 2021
Learning the art of giving great anal can help heal a past painful experience for a partner.

For a lot of people receiving anal sex for the first time, the experience is so painful they think, "Noooooo thank you! Not my cup of tea!" Not a bad instinct to follow, considering the health risks anal may entail.


I can relate, too. Anal was always uncomfortable for me until I tried it with an ex-porn star who knew his shit better than anyone I'd ever fucked. The pain-free result was one of the top five experiences of my sex life. I came so hard I broke straight through to the 10th dimension!

If your partner wants to take it in the butt and their first time was unpleasant, give these handy steps a try to create a smoother experience in the future.

Of course, full and enthusiastic consent is always essential. So make sure your partner is totally on-board with trying anal again. If a past experience has traumatized them to the point that anal is no-go, find other hot things to try together.


Read: 3 Porn Stars Share Their Best Advice for Anal Sex

Make Sure You Have Plenty of Time

You'll have to warm your partner up considerably for their muscles to relax and stretch enough to comfortably accommodate anal penetration. This may take longer than you'd expect. I'm talking two to three hours minimum!

The process will be no fun for either of you if you try to rush it. Take the phone off the hook and make anal the main focus of your evening.


Take the Plunge Into Enema Play

Because the anus and rectum are extremely sensitive areas, even tiny bits of fecal matter can make your partner's experience less pleasant. If y'all have never done enema play, this is a great time to start. Cleaning out your partner will help you clear an unimpeded path for penetration.

Here are a few tips for ensuring a fun enema play session:

  • Make the activity kinky and/or erotic. The first time I received an enema, I was freaked out and embarrassed. I ended up loving it due to the intimacy involved and the way my play partner fit it into our D/s dynamic. Your attitude toward the activity will make all the difference for your partner.
  • Heat the water to around 100 degrees. If it's too hot, you'll burn your partner's colon. If it's too cold, however, they may experience cramping.
  • Help your partner find a comfortable position to receive the enema. You have a number of great options to choose from, so find one that they can enjoy. Try to choose one that facilitates the process of gravity pulling the liquid of the enema into your partner's body, as well as one that doesn't put pressure on the stomach area.
  • Repeat the process until your partner's rectum is completely clean and free of bits of poop. (They'll be able to tell by checking out the liquid they release.) This could take 2-3 rounds of filling and emptying their insides, but it's well worth it. (And a good time, if you're into this sort of thing!)

Read: Because You Wanna Know: How to Do an Enema Before Anal Play


Help Your Partner Physically Relax

Muscle tension will prevent your partner from smoothly accepting anal penetration. You'll both have an easier time if you take steps to help relax their body from head to toe.

My porny ex-play partner would run me a warm bath, slowly wash my hair, and help me get clean before diving into the next preparatory steps. This would not only allay any fears I had about sanitation, but also put me into an extremely zoned out state of bliss. I highly recommend taking this route and following up by giving your partner a post-bath full-body massage. You'll have them drooling and begging for more (if they manage to stay awake).

Use Tons of Lube Throughout the Process

The anus doesn't self-lubricate during times of arousal like vaginas do. Using copious amounts of lube during anal play is an absolute must if you want your partner to have a good time. Cover their asshole, your dick, and/or any toys you plan to put inside them with enough lube to ensure a silky, slick feeling.


Also, be sure to pick up a silicone or oil-based lube so you won't have to pause to reapply too often. Water-based lubes tend to dry out more quickly, making them less ideal for anal sex.

Stretch Your Partner With Fingers and/or Toys

Have your partner lie on their side or stomach and drench one of your fingers in lube. Then, slowly and gently press it into your partner's ass, giving them time to adjust to the feeling of being penetrated in a place that's not specifically designed for it. (And don't forget to clip your nails first!)

You can also start with sex toys that aren't too wide in diameter, like small butt plugs and/or dildos. I specifically recommend:


  • Anal plug training kits that come with a variety of different sizes. You can start your partner off with the smallest size and work your way to the bigger ones once they're feeling comfortable.
  • A vibrating dildo or anal plug to help massage your partner's opening and provide amazing stimulation.
  • An inflatable butt plug, which you can gradually pump with air and expand while it's inside your partner, meaning you won't have to keep inserting and taking things out of their anus while warming them up. This can make for a more relaxing experience.

Read: 10 Kick-Ass Butt Plugs for Anal Play Beginners

Provide Excellent Foreplay

Of course, slowly teasing open your partner is foreplay in itself, but there are other steps you can simultaneously take to add eroticism to your pre-anal sex ministrations. Start to stroke their clit or cock, kiss their skin, blindfold them, or do whatever else they might find enjoyable but not overwhelming. If they're properly aroused, it'll feel much better (and hopefully AMAZING) when you finally insert your actual penis or a strap-on inside them.

Enter Your Partner SLOWLY

The two scariest points of anal for receivers are usually the moments of penetration and removal. You can help your partner relax by taking these moments at a snail's pace and using lots of lube.

Don't continue pushing during initial penetration until your partner can accept your size without discomfort. If your partner feels pain, they're at risk of injury.

Once the head of your penis or toy comfortably makes it past the ring of muscle that makes up the external sphincter, you should be good to continue.

Help Ease Any Worries They Have

As a receiver, I always used to get way too caught up in worries about poop to enjoy myself. My porny play partner of times past helped me chill out by talking me through this.

"I feel like I have to shit."

"Yeah, but you don't actually have to. We cleaned you out completely. There's nothing inside you."

"... Still feels like it."

"Right, but you couldn't possibly poop anyway while I'm pushing my dick inside you. Don't worry about that."

These were good points that helped me push past the initial mental freakout of the sensation and begin to enjoy myself. If your partner is having similar worries, help talk them through it as well as you can.

Try Different Positions to Find What Works for Your Partner

Our bodies are all shaped differently. What works best with one partner during anal may feel horrible to another. You can try having them lie on their side, or on their back with their knees pulled against their chest, or whatever else feels good. The point is to let them decide on the position before you get serious about thrusting.

Don't Forget the Dirty Talk

Soooo... I have a "daddy fetish," and my play partner used to take full advantage of it by talking to me during sex in a low, relaxing, hypnotizing voice.

"Babygirl... you like feeling dirty, don't you?"

Why yes, I like it a lot! Thank you!

Mindfuck your partner with dirty talk by focusing on their fetishes so you can get them into the horniest head space possible. For a lot of people interested in anal, its "dirty" or taboo nature is a big part of the appeal. Get creative!

Get. Your. Partner. Off. (If Possible!)

If anal by itself isn't enough to bring your partner to completion, you can either stimulate their genitals with your hands or have them touch themselves.

Either way, having an orgasm during anal sex can be a deeply exhilarating and memorable experience. Help them achieve it!

Of course, if they don't or feel like they can, it's no big deal. There's always more fun to be had next time!

Read: Don't Have Anal Sex If ...

Try Not to Get Too Carried Away While You're Trying to Come

It's unwise to thrust at full force during anal sex, especially if it's new for your partner. Doing so can cause tearing and other damage to their anus. No good!

Your partner may very well be begging for you to go harder and faster in the heat of passion, (I was!) but until you've got more experience successfully enjoying anal together, I recommend holding back and saving rough sex for other occasions.

Back Out Slowly

Once your orgasm has finally subsided, don't try to make a hasty escape like you just robbed a damn bank. This can be uncomfortable for receivers. Take your time when removing yourself from your partner's body.

Clean Up Before Moving on to Other Sexy Activities

You don't want to risk any nasty bacterial infections, so be sure to wash any part of yourself that was inside your partner's butt before continuing play.

And that's it!

Honestly, these days when I hear friends say they don't do anal because it was too painful on the first try, I always think it's a crying shame. There's so much potential for intense pleasure and bonding through anal sex. You just have to approach it like the delicate art that it is.

Molly Lazarus

Molly Lazarus is a kink and sexuality writer based in the Bay Area. She dreams of a world where consent-loving hedonists can explore the depths of their depravity without fear of persecution or sexual abuse.

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