5 Ways To Get Your Partner To Try Anal

Man and woman smiling in bed together

Anal sex is considerably more mainstream than it has ever been, but yet, many women (and men) still shy away from it. Why is that? Why is anal sex such a “no-no” subject? The most common misconception about anal sex is that it “hurts.” Truth be told, anal sex should NOT hurt if you are doing it correctly, and it should be a pleasing experience.

For heterosexual men the big turn off is that “anal sex means I am gay.” Guys, let me tell you, there are a whole host of men out there fully enjoying the benefits of anal sex within their heterosexual relationships. So, how can you get your partner – whether male or female or non-binary  – to experience the joys of anal? Read on and I will give you some suggestions. Here is a nice progression of activities to get your lover ready to take the anal plunge!

1. Talking, Asking & Entertaining 

Of course the most important aspect of any relationship is communication and honesty. If you cannot talk openly and honestly with your partner about your fantasies, desires, likes and dislikes, your relationship will never grow to its full potential! Furthermore, if you cannot feel free to refuse certain activities, then your relationship is also not as strong as you would like and you should NEVER feel forced to do anything, especially sexual, even if you are in a loving relationship.

So, if anal sex is something you would like to try with your partner, tell them why you would like to try it, what it would do for your sexual relationship and why they would enjoy it too! Anal sex is an equal opportunity pleasure experience. Both men and women have the same nerve endings in their rectal canal and men have the added bonus of the prostate spot as well, which can be much like a G-Spot for men. The first step in getting your partner on board with anal is to explain how it would be a PLEASURABLE experience for you both. Describe how much excitement you would get from performing anal stimulation on your partner and how pleasing it will be for them as well. Explain that this is for mutual pleasure, not for control or pain or even because it is a “taboo” experience.

2. Rimming

Sometimes it is much easier to get into anal play through some light “rimming” of the anal opening first. This can be done via tongue (licking around the anus) or finger. Just remember, if you are doing this to a woman, never go from ass to vagina without washing or gargling first. Otherwise you'll be brining bad bacteria to her vagina that could potentially cause a UTI or yeast infection.

Many men and women find a light anal stroking to be extremely pleasurable during oral sex. So, if you are on the road to experiencing anal, the first stop is always rimming. Remember to never insert your finger without consent of your partner. Slow, slow and slower wins this race.

3. Fingers First

For many people – both male and female – the idea of something as large as a penis (or even a butt plug) going up an “exit only” orifice is scary. Truth be told, it is never wise to just “jam it in” there, but instead, to work up to it. So, if your partner is wary about trying anal penetration, start slowly with one finger and then work your way up to multiple fingers.

Use a well-lubed (and I mean WELL LUBED) finger and gently circle around the anal opening. This is great to do in conjunction with oral sex because when someone is going down on you, your attention is focused on that pleasure. As your partner heats up, gently and slowly push the tip of a finger in. Always go slow, allow the rectum to close around the finger as you push slowly in. Once your partner feels how good just a finger feels, you will be ready to move on to larger objects.

4. Anal Toys

One of the absolute best ways to work up to full-on anal penetration is through the use of anal toys. TooTimid has a full range of anal plugs, anal beads, anal dildos and even special prostate stimulating toys that can bring anal play to a whole, new level!

Once your partner has consented, begin with a smaller anal toy and play around with the level of penetration that they enjoy. These toys are specially made to be smooth to ensure minimum discomfort. At this stage the goal is most definitely to show your partner how enjoyable anal penetration feels and to relax them with the idea of full-on penetration. Check out our best selling anal training kit below:

Recommended Product: The Rump Rockers Silicone Anal Kit
Image of 3 purple anal plugs

5. Pushing Penetration

If, at this point, your lover is open to further penetration then it is officially time to try penile penetration (or larger dildo/strap on dildo/prostate toys). The absolute most important part is: LUBE! Your anal canal does not lubricate, so lube is your friend. Lube up your penis or toy and always go slowly. Push a little at a time. Encourage your partner to relax and breathe. Pushing OUT during insertion helps the muscles to extend and allow the object inside. Never, EVER continue to push if your partner says it hurts or is too uncomfortable. You need to go slowly, a little at a time, and wait until your partner has indicated that it is OK to push in further or faster. Once the anal canal has been stretched and the lube has coated the insides, the experience becomes very enjoyable and the penis or toy will slide easily in and out. Just remember, listen and respect your partner’s cues here!

Pro Tip: Never, ever push your partner into anal sex if they say they do not want to or are not ready. Just like regular sex, this is a consenting activity. You should never push your partner to do this activity. If you do, you may just lose them in the relationship, and no sex act is worth destroying a relationship.

Have You Ever Had Anal Sex? Let Us Know Below With An Anonymous Comment!


  • Charles

    When we were younger we enjoyed anal sex once every 3-4 months. My wife said she had some of her most powerful orgasms through anal sex. The first time we tried it it was a disaster. e didn’t realize the need for lots of lube and foreplay. After a few months and some research we tried again. This time we had regular vaginal sex first. I always made sure she came before I entered her. After we relaxed a bit she got on knees and elbows I put some KY on her butt and some on a finger and slowly pushed in. I used slow gentle circular strokes after a while I added a second finger. She said it hurt a bit so I stopped until she said to continue. I did the same thing with a 3rd finger.. Feeling she was stretched out enough. I put a loot of KY on my penis.As soon as I pulled my fingers out I put a big glob of KY on her and quickjly entered her with just the head of my penis. When she said it was ok to continue I used long slow strokes. I reached around her and rubbed her clit. Unfortunately I could not hold back and came before her. But she came shortly after me with a very powerful orgasm. We didn’t do it very often. Only once every three or four months but the results were always the same.

  • Pucker Hole

    Anal sex and pegging are different beasts. I love them both! My first anal sex experience was a long time ago with a friend that loved to suck me off. I decided one day that it wasn’t fair that I was getting an orgasm and he wasn’t. I enjoy sucking his dick but can not handle his squirt…. Makes me about puke… so I decided to give him my butt hole. The first time was a very slow process of him inserting his hard cock inside me as my hole stretched, but it felt amazing! We had that relation for many wonderful years, he loved to suck on me and I loved him to fuck me. Later in life and I was married, I talked the wife into pegging me. Back to feeling amazing! After divorce, I have had several girlfriends that have enjoyed pegging me too. I often fantasize about my first times of anal sex and my first prostate orgasm. I keep looking for more.

  • Dragonfly

    I havent tried it before but I’m looking forward to doing it soon. We both are.

  • bigD

    Yes. I had multiple experiences.
    first was unsuccessful because I was too anxious and no lube.
    second time was with a different partner who never did, we were in love. Teasing her anally and vaginally, it made it pleasurable for the both of us, she was so wet it was perfect lube. First Success and it was mind blowing, Tip first then pulled out please then a little bit more then pulled out then all the way.
    third time different partner her first time, she totally allowed me to explore her body because yes we were in love. Spit has been great lube mixed with her fluid. Wet wet is a must must.

  • Michelle

    Lube is key here! After the 1-2inch entry point- there is no pain from stretching. It can be a wonderful blissful orgasm for women. I think every woman/man should experience it. It’s a full on body orgasm when you let it happen.

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