Anal Sex Tutorial 18 comments

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Anal Sex Tutorial/ How to introduce Anal Sex


**Author’s Note** ~ I have been getting a bit of a backlash about this post from some quarters, so I felt the need to clear some things up.

To those who say the author obviously has never had anal sex. I have both been on the receiving end and the giving end. I’ve had it be painful and a oh hell no experience as well as a love this give me more experience.

To those who are screaming about the use of anti bacterial wipes. I don’t mean cleaning wipes. I am referring to Wet Ones. They are a handy and  effective way to cut down on the bacteria that may be present when doing anal play. .As for the use of gloves, yes, that is an option and yes, a condom is also a must if you are not fluid bonded with your partner and can decrease bacterial spread. We use a condom on our dildos. I prefer to not use gloves. Your experience and wants may differ. Also, an enema ahead of time can really help cut down the risk of mess, but even after one you still might have a bit of poo. It happens. It’s really no big deal.

**Beauty’s Note** ~ We use Scott Naturals Flushable Cleansing Wipes at home and also Wet Ones when we travel.

To those who are fussing about my saying to push past the pain. I always have a bit of pain when first entered as the dildo or in the past, a cock head gets past the sphincter. I am not talking sharp pain, but yes, a burning pain that is quickly gone. It makes no matter how ready my body is. I am not speaking of sharp pain or lasting pain. Then the body isn’t ready and you could do damage. 

Finally to those that fuss about the article having the tone of speaking to men. I write articles about BDSM, many of those who will be the ones giving anal sex are dominant men. The search engine of my blog gets littered with terms seeking anal punishment and forced anal. The tutorial can apply to everyone, but my goal was to talk about how anal sex can be pleasurable if done right. If you force it and hurt your partner you are violating them and will have zero chance of adding anal as a pleasurable activity for both of you in your sex life. I am a lesbian so all your ire about not being sex positive and including all types of pairings and making certain I use pronouns that cover F/F, M/F, M/M does not mean the tutorial can’t be transferred to strap on play, pegging, M/M intercourse, etc. Whether you’re a man or a woman your anus is similar, and I can’t speak of the added issue of the prostate in men because I am not well schooled about them. Rant over. Back to our regularly scheduled program.**

I have decided to add this section on how to safely introduce anal sex into your relationship because the interest in anal sex is the number one topic people search for. I am also somewhat dismayed because people find my blog by putting forced anal sex or anal sex as punishment in domestic discipline in the search engine. If you are a HoH or dominant that thinks forced anal sex is a good way to discipline, please read the section about forced anal sex used as a punishment either in a domestic discipline situation or in a D/s relationship.

In that section on discipline, I say that in no way is it acceptable without complete consent. I will say it again. Forced sex is rape. Please, people, there are plenty of women and men who love anal, and a lot who have never had it done properly that would like it if they had a good experience with it. If you find pleasure in being the fuckee while engaging in anal sex or really want to try it and wish your wife, girlfriend, or boyfriend was open to trying it or allowing you to boink them anally, then proceed properly and introduce them to a pleasurable new sexual act.

Anal is not for everyone, and those who say, ‘No way’ should be respected. If you get consent, then please follow the steps below. Do not think it’s okay to hold your partner down and fuck them anally. That will destroy any hope you ever had of getting them to give consent in the future as well as making them afraid of or resentful of you.

What you need ahead of time:

  • Towels and anti-bacterial wipes – Anal sex can be messy both because of the lube and because mess can happen. I always have issues getting the lube off my hands after I use my fingers to play with and open my partner’s anus to relax them and when I lube up the dildo. Anti-bacterial wipes are good too, but putting a towel down is a good idea as well. Remember your fingers, dildo, or cock will still have bad bacteria on them if they are not washed or you have used anti-bacterial wipes. Wiping your hands off on a towel makes them less messy, but not clean enough for the mouth or vagina.
  • Lube – I like Liquid Silk. Lots of lube will help make the experience good for both of you. Seriously, the stories of guys, or women with strap-ons, shoving their cock in using only spit for lube is a bad idea. I also think that even when wet with your partner’s juices, the anus needs lube before pushing in. You can cause tearing inside the rectum that can lead to a bad infection and serious health conditions. A tear in the rectum plus poo full of bacteria is a disaster waiting to happen. IMO just say no. It’s a bad idea.

Prepare your partner ahead of time. They will want to make sure they are cleaned out. Enemas work well for this. You don’t need the whole enema bag kit unless you both are into that. A Fleet Enema kit works fine. Please be respectful and allow your partner privacy if they wish it. Things having to do with the butt can be embarrassing. Yes, I know that humiliation can be a kink, but make sure it’s consensual. Give your partner sometime after the enema so they aren’t feeling like they still have to go. If this is your partner’s first time they need to know that despite every effort to be clean inside, mess can happen. Putting a condom on your penis or dildo is a good idea.

Once your partner is clean, lay them on the bed on their stomach on a mound of pillows, bent over on the spanking bench, or over your lap so they are feeling comfortable. Remember this experience is to be enjoyable so they will be open to doing it again. Make sure towels and anti-bacterial wipes as well as lube are close by. Use your fingers to tease their anus, rub your lubed finger over it and round and round, getting them relaxed. Don’t just go and shove your finger in. The key is subtle play: tease, circle, rub until your partner is noticeably relaxed and even moving with your finger or indicating they want more. Fingernails must be trimmed or cut short and clean. Remember, you don’t want to tear the inner walls.

Start slow, just the fingertip in with very gentle in and out movement. Make sure your finger is well lubed. Get more if needed. There really is no such thing as too much. Well, the whole bottle is too much, but use your head here. Push in up to the first knuckle and swirl the tip around, gently stretching. This takes time, try to get pleasurable sounds from your partner, watch their body language, and slowly go deeper. Talk to your partner. Tell them not to worry if they feel like they have to go to the bathroom. This is almost always because they now have something in their ass. It feels weird the first time something is going in and not out!

Give this finger play a lot of time, gently open them, one finger deep, swirling around slowly, gently in and out, then add another but just play with the tips in. Start over with what you did with one finger. If you get your partner moving with your hand, pushing back and moaning, great! Tell them to take deep breaths and push back. They may be holding their breath and not really thinking about it. Our body tends to tense up at new sensations.

You may be tempted to rub your partner’s clit to help her relax and get turned on, but remember, the hand that is going in your partner’s ass should not get in or close to the vagina. Use your other hand or if you are not that dexterous, stay away from the vagina and clit until after the anal prep so you can either break telling them to stay put or use the anti-bacterial wipes. Use them thoroughly. You can always use a condom on your fingers for easier clean up and to help make sure there is no ass to vagina contact.

So now your partner is stretched and ready. You have slowly helped the sphincter (ring of muscle inside the anus, towards the end of the rectum) relax. It is this ring of muscle that will offer the most resistance when you use your cock or dildo. Position them comfortably. This does not have to be doggy style but that position works well. You can have your partner on their back with pillows under their hips and legs up. This allows for eye contact, access to breasts and nipples, kissing, and watching your partner’s face. Lube up your cock or dildo, use lots of lube!!!!

Hold your partner’s cheeks apart and don’t do this in the dark the first time. You need to see. Aim well and push just the head in sloooooowly. Use very gentle in and out motions going in just a bit. Push deeper and as you feel the resistance of the sphincter, push past it. This is what will cause the most pain or discomfort. Be gentle; remind them to breathe and to push down or back. Go slow with gentle pushing, talk to your partner. Be encouraging. Telling them they are a dirty whore who loves being fucked in the ass can wait unless your partner is really feeling into it. Your partner is going to be worried about making a mess and all the new sensations, but mostly about the mess factor.

Once you have slowly pushed in, hold it for a little bit, talk to your partner, when you pull out is the feeling slick and easy? If not, apply more lube to the shaft. Once you feel your partner relax then things are good. They may say it feels weird, feels like they have to go to the bathroom, or that it hurts. Remind them they can use a safeword. Do not ignore the ‘please stop’, but ask them to relax, to give it a minute to allow their body to get used to the feeling. Rub their clit (clean hand please) to aid in relaxation, pull out so only the tip is in, then if they give you an okay proceed gently and slowly. Do not jump into wham bam, hard fucking like in the porno flicks. A good slow fuck is going to feel good to your cock because the ass is so tight. Go slow and use lots of clitoral stimulation. Anal orgasms are possible but you can save that goal for another time. Use clitoral stimulation to both relax your partner and so she gets pleasure. Remember you want her to like this so she will agree to do it again.

If you are a bit messy when you pull out, just shut up about it. You have towels and wipes there, use them. She will probably ask if she is messy and it will feel like she is, your dick just came out of her ass. Just say no, it’s just lube and cum and wipe your partner clean.


  • Use lots of lube.
  • Prep with your partner with your fingers.
  • Wait for your partner to show signs of relaxation or pleasure.
  • Keep towels at hand and anti-bacterial wipes.
  • No ass to vagina or mouth. This spreads bad bacteria. It just isn’t safe.
  • Talk to your partner.
  • Go slow, I mean really slow.
  • Shut up about any clean up that is needed. “No baby, it’s just lube, no mess.”

Now if you have passed go and collected a green light for anal and you both want the fantasy or forced anal, have your partner wear a plug to get their muscles relaxed. They can push it in and out, toy with it, wear it for an hour or so and use it to stretch themselves out. Have them lube themselves up before hand. This does not mean you don’t need lube on your cock or dildo. It just means your partner took care of anal foreplay and has already made themselves slick and ready. You can role play this with little imagination. Tone of voice, harshness of pushing in (WITH LUBE!) using derogatory dirty talk, holding them down, etc. THIS IS ROLEPLAY a consensual act of sex.

If you wish for your partner to be focused on a punishment spanking and add another aspect by using anal while spanking then please still use lube and use your finger (note the use of singular finger) or a small plug. It doesn’t take much to get a big sensation inside the ass. I do not feel the anal penetration should be the focus. The spanking which is heightened by the scolding and the use of a finger or small plug is okay IF your partner does not have anal on their hard limit list.

It is my hope that those searching for forced anal, anal rape, and anal punishment will take the time to read this. People, you want them to LIKE it. You will get much more anal sex if your partner likes it too. The use of anal during a punishment is okay if it is not on the hard limit list. Forced anal sex is rape. If you care for your sub, partner, spouse, don’t do that to them. Really, just don’t.

About JolynnRaymond

Writer of historical paranormal romance, kinky historical romance, and BDSM Mistress and Sex Blogger. I hold the position of being one of Kinkly's Top 100 Sex Bloggers. Two of my books, Taken in Hand A Guide to Domestic Discipline and His Lordship's Wayward Wife, have been nominated as best BDSM Non Fiction and Best BDSM Historical books of the year. The awards ceremony will take place at the BDSM Writers Con in New York City this August.

18 thoughts on “Anal Sex Tutorial

  • Jolynn Raymond

    I’m really sorry that happened to you. A relationship which uses discipline in any sort of dynamic should never use anal sex as punishment unless it is 100% agreed to by both parties under no duress.

    • JolynnRaymond Post author

      Thank you. I suppose my goal is to help couples everywhere have great anal sex. seriously though, safe and mutually satisfactory is what’s important.

  • annapurna1951


    Thank you for your kind words.

    I posted because I felt safe to do so.

    Personally, submission with some dignity is not an issue for me, but anal punishment would always be. For others like me, violating our rectums is unkind and hurtful. We are people with feelings and needs; we’re not looking for abuse. Some of us will tolerate it because we need to be loved.

    It’s in our nature to want to please and to be useful, so submitting is an act of service and love. Anal intercourse is one such act. I don’t see it as a burden. The initiator has the pleasure of viewing us from behind and is free to exercise the control she needs and wants.

    For correction, we have scolding and spankings. Even if I’ve done something wrong, I still need aftercare to feel whole.

    • Jolynn Raymond

      I am a huge advocate for submissives because there is such potential for abuse by those who think a D/s relationship is all about the dominant or those who have no idea what they are doing. Anal punishment only has a place in a relationship as something that is okay to use if both parties have agreed well before hand without coercion.

      Anal sex and or anal punishment has a high risk of being a trigger so must be proceeded very carefully. I personally do not use anal as punishment because though my wife would submit, it would have such a negative effect that the lesson to be learned from the punishment would be lost.

      No matter what the punishment aftercare is vital. I have an article in the BDSM archives titled BDSM and Aftercare. I don’t care if it is after play or after a punishment, aftercare is a must. My wife knows that the slate is wiped clean and that I love her very much when a punishment is over. There is lots of cuddling, giving fluids and chocolate if it was a play session, warm blankets and such. if simply left alone after a punishment one would not get the feeling that they are loved or that the wrong has been made right.

      Again thank you for your thought provoking post.

  • Jolynn Raymond

    No apology needed. Thank you for your great post. You bring up an issue I hadn’t really dealt with. The act of being on the receiving is one that causes vulnerability. I think that is why those in D/s or DD relationships see anal sex as a show of submission and that people are always searching for anal punishment which I do not advocate.

    Your input is much appreciated. Glad you stopped by.

  • annapurna1951


    Thank you so very much for your excellent post. You’ve handled the subject with great delicacy and respect.

    I’m on the receiving side.

    It took me a while to develop proper sensate focus to relax into the dildo. I overcame this issue with self-practice, which allowed me to control the action. Nevertheless, when the locus of control shifts to my partner, relaxation is something I can’t take for granted, so it’s important for me to concentrate. During anal intercourse, I do feel vulnerable and exposed. Those controlling the action may need to know that about their partner. Remember that we need to be encouraged.

    I’m bothered by mess and feel degraded by it because I feel responsible for it. I try to take a proactive stance, but it does reduce “spontaneity.” I check beforehand with a finger or dildo to make sure I’m clean. If necessary, I will shower or use an enema. I like to pre-lube with KY Jelly, but it’s expensive.

    I like your Fleet Enema recommendation, by the way.

    Diet is also important. I’ve changed mine so bowel movements have good continuity and adhesion without leaving too much debris. For most people, this will be a trial-and-error process.

    I agree with you whole-heartedly about protecting the vulva and vagina from bacteria. Going from the anus to the vagina can create a real health problem. It’s better to use two separate dildos.

    I apologize in advance for my explicit language.

  • JolynnRaymond Post author

    Thank you Maren. I certainly appreciate your words of support. It made me fume for a bit that people would get into an uproar over this and that, but decided to stay basically non confrontational and just state MY reasons and ways. As you said, their are a multitude of ways people have sex. The right way is what is right for them aside from the basic safety and pleasure tips.

  • Maren Smith

    Good for you for keeping this up as a post-it, despite the complaints. It never fails to amaze me that some people can’t help but nitpick another person’s article half unto death simply because their own experiences have differed. As if their way of having sex is the ONLY way, no deviations allowed. This is a good article. The information you have shared here looks spot on to me, and I thank you for sharing it with us! 🙂

  • Jolynn Raymond

    Hello and thanks for the reply. I didn’t see this until now. I have been in the lifestyle for close to 13 years and I simply write what I have learned over time. I’ve been at kink event classes, practiced things in my home with my partner, and asked those who are skilled in one thing or another to teach me if I don’t know the safe way of doing something. It’s really not creativity, it’s knowledge.

  • 情趣用品

    Your posts continually include a decent amount of really up to date information. Where do you come up with this? Just declaring you are extremely creative. Thanks once more

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