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THE DISCIPLAYGROUND®

THE DISCIPLAYGROUND®
N° 01 guides 16 JUL 2026 WEEKLY DISPATCH

For a lot of people, just hearing the word "anal" makes everything clench up — and honestly, that reaction was handed to us by movies and books. They quietly tied anal to porn, to violence, to pain, to being something only gay men do, and that left most people with a deep misunderstanding of it.

If that's where you are too, it just means you don't actually know much about anal yet.

Before we start, I think it's worth saying what you need for a first try, and whether there's any real danger. Don't go poking around blindly or daring yourself into it — be careful, or you'll hurt yourself back there.

This is my own first-time story, so I'm writing it the way it happened to me.

Can women feel pleasure from anal at all?

We keep coming back to one line: the brain is the biggest sex organ. Going by how nerves work, even ordinary skin can trigger an orgasm — so why not inside the rear? Some women genuinely feel pleasure back there. It just doesn't come from the prostate, the way it can for men.

I'll embarrass myself a little: as a kid who couldn't sleep, I'd nervously slip one finger in back there to explore. At the time it just felt like a curious little game. Once I got a bit older I started feeling ashamed of it — but I never forgot that particular sensation of something going in. These days, when my husband and I have sex, he'll often slip a finger in (about up to the first knuckle), and I really enjoy it.

Once regular vaginal sex is more or less familiar territory, you might start feeling the itch to try the back too. And honestly — for me, the bigger thing is the psychological satisfaction. The moment something enters back there, you feel like your body has been deeply accepted by the other person, like the two of you understand each other one step further. The coordinating you do while you explore raises the sense of being in sync. You enjoy that feeling of being conquered; the whole of you feels somehow complete. And for the partner on the giving side, that urge to conquer gets satisfied too.

Can you orgasm from anal without a prostate?

You might be wondering: women don't have a prostate, so can you even reach orgasm from anal?

First — you don't have to orgasm for it to feel good. Just like regular sex, sometimes you're not in the right headspace, or not wet enough, and the orgasm doesn't land, but the whole thing was still enjoyable. Anal is the same. On top of that, anal doesn't have to be only about the rear — you can pair it with oral or with vaginal sex at the same time, and get pleasure on several fronts at once.

How do I bring it up with my partner?

If you've decided to try it, talk it through first. So — how do you talk about it?

Start by letting him know you're curious. You could send him this article and say something like, "Babe, I want to try having both at once — would you do that for me?" If he hesitates, you can add, "I've heard it's even tighter back there than the front, you might like it even more — want to find out?" That way he feels like you've thought about it from his side too, not just chasing your own pleasure.

Of course, you might still get a no — and that's completely normal. With anal, both people being happy is what matters most. Don't get discouraged over being turned down. Try a few more times; if he really doesn't want to, don't force it. (This article also recommends toys made for the rear — exploring on your own is a great option too.)

If your partner happily agrees to try it with you, then get these things ready.

What do I need to prepare?

1. An enema bulb / nitrile gloves. If you're a bit of a clean freak and feel like the back is dirty, you can fill an enema bulb with warm water and do a simple rinse before you start. Once it's clean, you can put on nitrile gloves to be even more hygienic.

2. Silicone-based lube. When you're only exploring with toys or fingers at first, water-based lube is fine. But later, once a penis comes into play, anal for women really should use silicone-based lube — it doesn't break down condoms, it stays slick longer, and once something thick goes in, it's a lot more comfortable. (One caveat the original doesn't mention: silicone lube degrades silicone toys, so pair it with glass, metal, or coated toys — not silicone ones — and never use oil-based lube with latex condoms, because oil breaks latex down.)

3. A butt plug. If you're worried a penis is too big, you can start with a plug to help open things up — the foreign-object feeling is much smaller, and once you're okay with that sensation, moving to a penis later is no problem.

4. Condoms. You might think there's no pregnancy risk with anal, so a condom is pointless — that's a big mistake. Here, a condom is more about safety: it's dry back there, unlike the vagina which makes its own natural lubrication, and the rectal lining is fragile. If friction during the action accidentally causes a little bleeding, the risk of passing on infection shoots up. So not only do you use a condom, you use one with plenty of lubrication. And one reminder: if you want to do both the front and the back in one session, you absolutely have to change to a fresh condom — don't get lazy about it. Especially if you explore the rear first and then move to the vagina, the E. coli from the rear will contaminate the vagina directly.

What should I watch out for while exploring?

1. Trim your nails. Same as anal play for men — for a first try you can use a finger. Long nails can accidentally break the skin around the opening, cause bleeding, and raise the risk of infection.

2. Find a position that works for you two. A woman lying face-down with the man entering from behind, and the spooning position (both lying on your sides, him entering directly from behind) are both well suited to a first attempt — even just with a finger. Positions are really only a reference, though; there's no absolute standard. Finding the one that's yours is what matters.

3. Relax, deeply. More important than position is relaxation. Both your mind and the ring of muscle back there need to be relaxed. If regular sex needs foreplay, then the drier rear needs it even more. Give yourself 10 to 15 minutes of foreplay. You can have your partner massage your perineum — the area between the anus and the vaginal opening. You can also do it yourself: massage while breathing deeply, letting the anus fully open and relax. If you're too tense on a first try, you can use a relaxing spray made for the rear to help let go.

What does the process actually look like?

Rinse with an enema, and wipe the perineum from vagina to anus clean with a disinfecting wipe.

Put some lube on a bullet capsule, then slide it in back there. During the 15 minutes you wait, your partner can stroke and kiss your body, or you can watch something together to get in the mood. Don't watch the clock too closely; when it feels about right, take some water-based lube and have your partner massage your perineum and the rim, slowly pressing around the opening, working a finger in along with the lube.

Once it's in, wait a moment. The other hand strokes or holds you, breathing and relaxing with you. He asks if he can go a little deeper, and only after you say yes does he ease in slowly. He can touch around in four directions, asking whether any one spot feels especially good. Then he keeps stimulating the way that feels good to you — but not too fast, not too hard, everything following your lead.

When your breathing starts to quicken and you're fully relaxed, he can ask if he can switch to a plug or a penis. Same steps, going in. The end goal you can reach: a penis in the vagina and a plug in the rear at the same time. If you're in a rear-entry position and add some lingerie — a fox or rabbit tail — it makes for a visual feast you've never had before.

What does the first time feel like?

At first, it's a bit like the feeling of needing to poop.

A bit of pain, a stretched-full ache, a stinging sensation — all of that is normal. As long as you've got enough lube and you stay relaxed, you don't need to worry; the more tense you are, the more likely it fails. And of course, if you try it and decide anal just isn't comfortable and you don't want a next time, you don't have to push yourself. Some people get pleasure from stimulation back there; some women love being kissed there but won't let anything in. So explore with your partner and see which one fits you.

First-time tips and things to keep in mind

1. Clean up before sex. Whichever opening you're after, cleanliness is a must, and the back even more so. If a woman feels the urge to go before you start, my advice is to absolutely not attempt anal — do your business first. And clean up as well as you can; this is also consideration for how your partner feels, and it cuts your own anxiety, so you relax more.

2. Give it proper foreplay. Anal needs foreplay too, even though the back doesn't make much wetness of its own. During foreplay, the man can use his mouth and tongue on the rear too — a nimble tongue is hard to resist. At the same time, he can use a finger to gently stroke the clit out front to build arousal. He can even start by slowly, tentatively pressing a pinky in, letting it get used to the feeling of something going in and out.

3. Relaxation and lube — both crucial. The back is more nervous-tense than the front, so why did I find anal felt even better? Partly because we were fully relaxed through it, and I wasn't as nervous as I was my first time having sex. Maybe my brain released a lot of endorphins then, which dulled the pain effectively. The other part is that lube does a lot of work. For anal you can use ordinary water-based lube, or anal-specific silicone lube — the upside of silicone is that it evaporates less easily than water-based and stays slicker longer.

4. Protection really is necessary. Anal needs a condom too, and very much so. The area around the privates carries plenty of bacteria, and it's easy to get an infection if you're careless about hygiene. Especially when a man finishes with the rear and wants to keep going in the vagina — please note, you absolutely have to change to a fresh condom. Change the condom. Change the condom. Don't cause big trouble to save a condom. Or, if after anal you want oral, the man should go clean himself off first — that's a show of love for the woman too.

5. It might not work on the first try. Just like first-time vaginal sex, anal won't necessarily succeed the first time — there may even be more obstacles. You need to let the back gradually get used to it. You can start slowly with toys or fingers; it takes patience. Especially the first time, go slowly, don't rush, and if it doesn't work, don't be disappointed — enjoy the process of exploring rather than fixating on the result. If you feel sharp pain, you have to stop — just like vaginal sex, it shouldn't be painful. So practice. The early stretching might take several sessions of exploring, even weeks or months, until one day, you'll truly get to enjoy the pleasure of anal.

6. You really won't hit stool. A lot of people's first reaction to anal is: that's disgusting, won't you hit poop? If anal hit poop that easily every time, how would gay men have sex at all? The fact is, stool is a long, long way from the opening — unless you've had diarrhea recently or haven't fully emptied your bowels. As long as you usually eat healthily and are regular, the area is actually quite clean. If you really don't believe it, try a toy first and see whether anything's on it when you pull it out.

7. Don't put limits on yourself. I've noticed that we women always restrict ourselves too much when it comes to sex — too embarrassed to speak about it, too scared to try anal, afraid that saying it out loud will make people think we're perverts. But our bodies should be ours to decide on. For partners to explore different positions together is a perfectly reasonable thing. Why let other people lock invisible chains on us — and worse, why do we lock those invisible chains on ourselves? I'm grateful my husband kept gently asking whether I'd be willing to try, instead of giving up on the idea after I turned him down again and again. And I'm grateful to myself for being willing to loosen the restraints I'd put on me, for trying it on a whim, and opening a brand-new door for myself.

8. Doing it is the only real way to know. Like a job — there are a lot of things you simply can't know you're suited for until you try. If we only ever understand something from the internet, from other people's reviews, our judgment of it is nowhere near the real thing. Take anal: afterward I went online to search, and most of what I found told me anal would hurt, would bleed, could cause severe outcomes (like bowel perforation — if I'd seen that word beforehand I would absolutely never have tried it). But my own experience told me that as long as the process is gentle and handled well, it feels good, even better than vaginal, and it isn't nearly as scary as imagined. Of course, some people may really dislike anal. Different strokes for different folks. But don't pass judgment on something just because "other people say…" — after all, only by experiencing it yourself can you understand what it's really like.

---

That's my little share about my first time with anal. I'm putting it here because I think a lot of women have agonized over whether or not to try it, and some want to try but don't dare. What I want to say is: whether something is right for you, only you can know — and if you never try, how would you? If you do go for it, the two things you genuinely can't skip are taking it slow and using enough lube. When you're ready to take more control of pace and depth, a dildo is the gentlest place to start; a sex machine is the last step, never the first.

— end of dispatch —
DANA REYES writes for THE DISCIPLAYGROUND.
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