Anal Sex Tutorial

On one of my Facebook groups, the topic of anal sex came up, questions about how to initiate and actually do it brought great responses from others and since I have a LOT of experience with anal sex, I thought I would share, too. It got to be wayyyyy too long as a FB post, so decided a blog post was a better idea.

Therefore, here is a pretty stream-of-conscious explanation about having anal sex for the first time (in particular), but even those of us with a lot of experience can always learn more, right? If you see something I’ve forgotten, please don’t hesitate to let me know so I can amend this tutorial.

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How I Learned

When I was 17-21 years old, I lived with a steady stream of gay men, up to 8 at one time, often in one room… no bedrooms. I recall watching beds-full and then rooms-full of men having all sorts of gay sex. Resting on my side, head on my hand, elbow on my bed against the wall, I studied what the guys were doing. I did eventually ask for instructions and they graciously taught me, step-by-step, how to give oral sex and receive anal sex. I’ve had the opportunity to practice both skills many, many times over the decades and from what I have heard, I’ve been a very good student. Now, I share with you!

Inclusivity/Intersectionality

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While I am very fat, white, have physical disabilities, am a multiply neurodivergent Latinx, polyamorously kinky, sometimes-dyke, it’s important to me to be as inclusive in my language and purpose as possible. When I say “cock,” I mean penis, dildo, fingers… whatever you consider a dick. As I write, I “see” all genders & sexualities, as well as an endless variety of bodies… -abled and differently so, with and without specific genitalia, very very thin to super-gorgeously fat (like me!). Even so, I will make mistakes and take missteps… I apologize in advance. I’d love to know where I went sideways if you have a moment to leave a comment.

A plea to artists & photographers

It took me way too freakin’ long to find appropriate drawings and photos of different races, abilities and sizes… never mind not finding any trans drawings at all. I found one drawing of a woman of size. That’s just wrong! If you are an artist or photographer, I beg of you, when you create sex pieces, to please draw & photograph people, not just the standard-sized white man and woman… and fuck that woman-is-always-receptive crap, too.

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A multi-racial, male-as-receptive-partner (“Pegging“) illustration. A fantastic image!

Words & Euphemisms

Being in the Adult Industry, I know and use a wide variety of sexually-charged words. As I embark on this Anal Sex Tutorial, I know verbiage can be welcoming or, if not heard positively, show someone to the exit. However, I cannot possibly know if your proper word for anus is butt hole, asshole, rosebud, pucker, hole, rear door, bunghole or any number of other euphemisms that exist in English or the other languages you might speak. If I use a word that makes you wince, please replace that word with your own personal favorite and do that throughout the piece.

Taboo

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We all surely know that talking about anything dealing with the anus, including defecating, is pretty much not allowed in our culture. When we talk about it in a sexual context, people and religions nearly lose their minds. Anal sex even has its own legal term: Sodomy. (“Sodomy” includes anal and oral sex.) Sodomy laws weren’t abolished completely in the United States until 2003. TWO-THOUSAND-THREE! 

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Lawrence V. Texas (2003)

So, if just saying the words surrounding anal sex is frowned upon (understatement), actually touching and penetrating the anus can cause intense reactions of disgust and revulsion. Please know this is so normal! But, sexually-exploring folks with the same societal pressures as you, have crossed into eroticizing anal sex and, with some re-training and re-focusing your mental habits, you can, too!

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Onward, Ho!

Lubricant: The first, last and middle word with anal sex is: LUBE! You can never use too much lube when doing anal sex. Butt holes don’t self-lubricate like a vagina or mouth, so we need to lube the back end like mad. There are a variety of types, so if you are using gloves, condoms or toys, be sure to choose the correct lube for your needs.

(At the end, I will explain the “cleaning out”/enema process. Assume at the moment, your prep has already been done.)

Gloves (Condoms in a moment): Many, many people use gloves… for the obvious cleanliness reason and to cover fingernails that might scrape the colon. Remember to note if you or your partner are latex-sensitive so you can buy non-latex gloves. If you do not use gloves, please make sure your nails are short and do not have hangnails that can scratch your partner’s insides.

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Non-Latex glove… using one on each hand? Not a bad idea.

Safe Words: For everyone, a “Safe Word” is really good, but especially if you are remotely nervous about playing with your arse. The most common Safe Words I have seen are Green for “keep going,” Yellow for “please slow down” and Red for “stop right now.” Be sure to clarify that Red means “stop moving,” and not “PULL OUT FAST.” Sometimes we just need to breathe for a moment before continuing when we call Red. Red might very well signal the end of the session, so the person inside the anus needs to pull out very slowly. Never hesitate to use your Safe Words and there should never be shame for calling an end to the session.

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The “Red” Safeword for my play right now: Rochambeau!

Triggers: You and your partner can discuss private/personal boundaries as well. Anyone with a sexual abuse history might be triggered with anal play… and not always just the first time, either. Be aware of what you are feeling and use your Safe Words if you feel weird mentally/emotionally at any time. There is NEVER any shame for stopping sex… at any time… for any reason.

Aftercare: If the receptive partner calls their Safe Word for pain’s sake or because they were triggered, Aftercare is incredibly important. Aftercare is different for each person. Some need to be held, whereas others need to not be touched at all. Learning each person’s Aftercare needs is typically trial and error. Honor the process and the triggered person’s needs… not your own until they are taken care of. But yes, both may surely need processing after the session.

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Anal Toys & Training

F is for FLANGE: For many, the first line of anal training is using toys. An enormous variety exists, from very small/thin to incredibly oh-my-fucking-god huge. Just like the main word in anal play is “Lube,” the code word for putting any toy in your butt is FLANGE. Emergency Rooms don’t even bat an eye when someone comes in with a dildo/vegetable/fruit/dog toy/space ranger stuck inside, but it can be really embarrassing for you. Please, please use toys designed for anal play and leave the MacGyver toys to others.

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The Flange

Good Vibrations: I do not work for Good Vibes nor make one cent from recommending them. I just adore that they are so people-oriented, including education for the wide variety of bodies and sexualities. Their customer service is amazing. You can call them and they are glad to help you figure out your needs and then allowing you to decide on your own without the upselling crap a lot of other places are wont to do. Their toys can be fairly expensive, but they last for years, even with lots of play. Take a peek at their Anal Toys & Lube and see what they have to offer.

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Strap-ons are awesome for all genders.

Anal Beads: are a place many folks start (most aren’t like bead beads), then move to gradually larger toys. The toys can be fairly thin, can be graduated in size, can vibrate and some are made just for men. Look around and see which ones resonate for you. Good Vibes has beginner kits that offer some guidance.

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Anal Beads

Butt Plugs: are meant to be put in and left in, either during sex or as prep for the night’s fun. Some people put it in when they come home from work… and some put one in when they are heading in to work. They can be worn for no longer than 8 hours (like tampons) at a time. It is kinky as all get out to walk around at work or sit on your office chair squirming all day.

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Butt Plugs

Plugs have even gotten fashionable with jewels and everything.

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The jewel is the flange!

Anal Dildos: are yummy!

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Anal Dildos

Especially when they vibrate!

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Vibrating Anal Dildo (the black bullet vibe is inserted into the bottom)

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Setting Up

Protect Your Area! Keeping your play area protected helps with clean-up, especially since you’re using 10-gobs of lubricant. Lay down disposable underpads, beach towels, a tarp/shower curtain… whatever you think will be a great lube-catcher. Anal sex is not something to do without floor, carpet or especially, mattress protection. If you strive for a small landfill impact, you might choose wet washcloths and hand towels to wipe your hands with during the sex session. I, on the other hand, am horribly wasteful and choose to use baby wipes and paper towels… not real ecological, but much easier to clean-up.

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Condoms: In my experience, most folks choose to use condoms when having anal sex. Even with dildos. There’s the safety factor (STIs etc.), but they are also for cleanliness and ease of clean up if you have a cismale orgasm inside your rectum. Condoms can also be a concrete reminder to not put the penis or dildo into the vagina after leaving the anus. Instead, pull the condom off, wash your hands and toys in soapy water, rinsing, then you are welcome to continue with vaginal play. If you use condoms with oral or vaginal sex, change your condom after anal play.

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Un-Sexy Health Note!

It really is crucial to never go from the anus to the vagina.  As I said above, body parts and toys once in the anus canNOT go into the vagina or mouth without a thorough soap and water cleansing. I cannot stress that enough. If you rim the anus (analingus), do not lick from bottom up to the vagina. If rimming is going to be done, start “high”… the mouth, the clit, the vagina, the perineum, then the rectum. Never the other way around. Also, you should consider having dedicated anal play toys. Even cleaned really well, there’s always a chance of harboring some bacteria the butt hides inside.

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From top to bottom.

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Touching

S L O W: Start slow. Penetrating the bunghole is rarely the first item on the menu. Lots of touching, kissing, nipple & genital play helps relax all involved. For some folks, having at least one orgasm before attempting anal sex makes things easier as well.

Fingering: As one moves toward the rosebud, lubed fingers can feel delicious when the pad of the finger is slid over the hole, back and forth, gently… then in circles around the hole, not touching it directly… moving inward as a nautilus. Kissing when the finger is nudging closer helps the relaxing tremendously.

Slipping In: As the first finger begins to slide in, it needs to go really slow. A bit, then a bit more… it can take more than 5 minutes to slip a finger in to the first knuckle. Slow is fine. However, if you want more, faster, do not hesitate to state your need and/or desire.

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Enter the Cock: As with the finger, once the dick or toy is set for rear entry, slow and easy, please. Gentle, slow, touching, caressing, sweet words of encouragement (from both parties) all help to create a positive experience. Inching in, bit by bit, then once all the way in… not moving while the receptive partner acclimates to the fullness. At any time, if the receptive person needs to stop and breathe, do not hesitate to tell your play partner.

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Wahhhhh! The first 2-5 times one has anal sex, the first 5-20 minutes is “the worst part” (quote from dozens of folks). It can be really uncomfortable and not orgasmically pleasant during the early part of the session. Breathing helps the process… hurting less and hurting for less time. I promise, the time does eventually arrive that the entry is a fantastic experience.

NOTE, HOWEVER! If it hurts a LOT, stop. Tearing can happen inside and that isn’t so good. As well, if there is any blood, stop immediately. If it continues, get help right away.

No wahhhhh? If you do not have discomfort at all, that is awesome! There’s not one thing wrong with you. Each person’s body is elastic in different places. Yours might be in the anus. Lucky you! No passing any judgment on ones anus size, okay? We critique enough of ourselves.

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Masturbating with your hand or a vibrator can be an awesome relaxation technique when learning to have anal sex with your partner.

Get It ON: This is the part when you two have your anal fun! I will step out for awhile.

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After-Play: If your cismale partner orgasms inside you without a condom, be sure to head to the toilet toot sweet when you are finished, with a towel between your legs, because the semen can soften any stool inside and gooshy wet can drip out. If you’ve done a prep, it won’t be as dramatic.

Washing Up: Be sure everything involved in your play gets washed well with soap and water. Taking a shower, perhaps together, bringing your toys with you is an easy way to get everyone/everything risk-free for play next time. Wash towels and sheets and anything else that got soiled in hot water with bleach if possible. (White linens are good for any sex play, in my opinion, specifically for the clean-up aspects.)

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After-Sex Processing

Como siempre, it is always good and can be really important to touch base with each other about how the experience was for each of you. This can be part of the Aftercare or it can be something you two think about for awhile, then meet back up later to talk about. Even with a wonderful, passionate, uninhibited anal sex session, the re-emergence of the societal constraints of anal taboos is really common. I often encourage folks to email each other if they find speaking aloud is challenging. But try not to just ignore the experience, even if it wasn’t as pleasant for you as for your partner. See if adjustments can be made before scrapping the idea altogether.

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Enema Preparation for Anal Sex

Enemas are your friend when getting ready for anal sex. Planning ahead for anal sex encourages an atmosphere of anticipation, but it also removes the spontaneity some find erotic. You do what works for you.

I encourage using one of the smaller sized enema kits you find in regular pharmacies, twice. Others choose to use a larger bucket, soapsuds enema because it really cleans one’s colon out well. You can buy the bucket enema online or medical supply stores.

Follow the directions that come with the enemas and you’ll be fine.

I have lots of experience giving and having enemas so I offer these 3 pieces of advice.

  1. Lay towels (or, even better, disposable pads) under you while inserting and holding the enema before dashing to the toilet
  2. Turn onto your left side as much as possible
  3. Hold the fluid as long as possible… then a few moments longer

Try to do the enemas about 60 minutes before anal play begins. That gives the body time to expel the liquid. Using baby wipes to clean yourself, or better yet, a nice shower, before sex, will make sure you are fresh as a daisy for your partner.

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Conclusion

Whew! I had no idea I could talk so much about anal sex! I hope you’ve made it down this far with me.

I know there was a lot of technical… and even political… information, but I do want to encourage you to, most of all, have BIG fun while exploring with each other. Anal sex is a wondrous experience of trust and intimacy… even if it is merely for the length of the session.

Again, enjoy yourself!

Thanks for hanging in there and again, do let me know if I need to add or change something to be more inclusive and respectful.

Now, off with you!

And bend over, baby.

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3 thoughts on “Anal Sex Tutorial

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