There was wine in both of us and I decided we should try it that night, as if warmth were the same as readiness. Wine is not a yes. We had agreed earlier, dressed, that we were curious, and I still should have waited until the glasses were empty and we were ourselves again. I pushed. It stung. We stopped. Nobody learnt anything except that hurry is a poor teacher.

How to try anal sex without repeating that night turned out, later, to be almost dull. A shower. A small plug. More lube than I wanted to admit I needed. A word that stopped it, used once, without a sulk.

How to try anal sex when you actually want to learn something

People want this for ordinary reasons. Curiosity. A picture they have had for years. A partner who asked. A sense that there is a kind of fullness they have not tried. A wish to be the person who is game. I have been all of those. Game is the dangerous one. Game is how you skip the boring steps and then write a horror story you never tell anyone except a search box.

People do not want it for ordinary reasons too. It sounds messy. It sounds like pain. A previous attempt went badly. The idea does nothing. That is allowed. You do not owe anyone your anus because you have done other things, or because you said maybe in July. A no here is a preference, not a personality test.

I am not a doctor. If something is sharp, new, or it lingers after you have stopped, that is a GP conversation, not a blog. Most first-time sting I have met was hurry, dryness, and pride. Persistent pain is a different sentence.

Talk about it when you are dressed, not when someone is already lined up and hopeful. Say what you want from the attempt: a finger, a plug, maybe more, maybe nothing past that. Say the word that stops it. I like red. I have also used “stop” as itself, because this is not a scene where no is a prop. If you might treat “no” as play on other nights, pick a word that cannot be mistaken. Safe words earn their keep here.

The good night, the one I would repeat, started with a shower that was about being clean enough, not sterile. A towel on the bed. A bottle I could reach without a speech. A small plug I had already tried alone, on a quieter evening, so I knew the first stretch was possible. He was patient in a way that would look boring on a screen.

Fingers and plugs first

Nothing with a wide base of impatience. A finger, one, with more lube than dignity, is how I start with another person in the room. Nails short. Pad, not jab. Outside first: a press, a circle, time for the muscle to stop treating the world as a threat. Then a slow ask, not a shove. If I clench, we wait. Clenching is information. It is not a dare.

I used to treat the first knuckle as a test I had to pass. Passing is how you get a sting and a woman who says she is fine. I am trying to retire her. If it burns, you are not warming up. You are forcing a door. Come out. Add lube. Try later, or try another night.

A plug is useful because it stays. It is not a thrusting argument. Small. A flared base, always. Things that can slip in and keep going are how people end up in A&E, and I am not going to be cute about that. I bought a tiny one and felt faintly ridiculous, and then I was glad, because the ridiculous one was the one I could breathe around.

Try the plug alone first if you can. A locked door, a towel, time. I learnt more from ten unhurried minutes by myself than from any determined evening with an audience. Then, with a partner, you are not discovering the whole map while someone watches your face for a verdict.

If you are the one doing the touching: ask, then go slower than your hope. Watch the shoulders, not just the part you are interested in. Shoulders tell you. A joke that goes thin tells you. “Still good?” is allowed to be unsexy. Unsexy is how you get to the sexy bit without a story you regret.

Pegging is a different night, with a different conversation. Same lube religion. Same right to stop. I mention it so you do not treat “anal” as only one body being entered by one kind of person. My own history is mostly men, and most of what I can tell you first-hand is me receiving. The patience is the same job either way.

Do not skip to a penis or a larger toy because fingers felt “fine.” Fine is the start of warm, not the all-clear for width. Width is a new question. So is length. So is movement. One change at a time. I have ruined a promising start by adding thrust because I thought we should be getting on with it. Getting on with it is how the wine night happened, minus the wine.

Lube like you mean it

Dry anal is how horror stories get written. The rectum does not do the same helpful wetness a vagina sometimes does. You bring the slip. You keep bringing it.

I used to add a polite amount, as if the bottle were a confession. That is how you get friction and a brave face. Put down more than you think, and then more when it starts to drag. Drag is the warning before sting.

The best lube for sex in general is the one you will actually reach for. For anal, I reach for silicone more often than I do on an ordinary night. It stays. Water-based disappears and then you are grinding on a dry patch out of optimism. Water-based is fine if you treat topping up as part of the act, not as an interruption. I have used both. I have been happier, for this, with the one that does not vanish.

Oil is where people get romantic. Coconut oil feels nice. Oil and latex condoms are not friends. Oil weakens latex. If you need a condom, do not use oil. That is not a vibe. That is a breakage risk. If you are using condoms, stick to water-based or silicone, and check the packet if you are the sort who buys whatever is on offer.

Numbing creams are a plot I do not trust. If you cannot feel the warning, you cannot use the warning. Pain is information. I want it. I do not want it muffled so someone can continue a project.

Keep the bottle where a hand can find it. I have watched a man lose the moment hunting in a drawer. I keep it on the towel. The towel is also how you stay kind to the washing later. This is not glamorous. The good night was not glamorous.

If it stings and you have already drowned it in lube, stop. Sting that survives slip is your body saying not this, not now. I have argued with that sentence. The sentence won. It always wins, eventually. Better that it wins while you still like each other.

Positions with control

Control means the person being entered can change depth, angle, and whether anything is happening at all. Porn likes from behind because it looks like a decision. From behind is often the least control I have, especially if I am already a bit braced. I do not start there any more.

What has worked:

Me on top, facing him, my knees on the bed, my hand on his hip so I am the one who lowers. That is a decision, not a performance. I can stop at the first stretch and stay there. I can come up. I can laugh. I can decide the night is fingers after all.

On our sides, spooned, his hand where I put it. Shallow. Slow. A lot of kissing that is a way to keep me in the room.

From behind, later, if I ask for it, with my hand back to keep him shallow. If he treats my hand as a criticism, we stop and I say it is a steering wheel, not a review.

Toys follow the same rule: smaller than pride, flared if it stays in, no thrusting argument until the staying has been easy. I do not get used to things that hurt. I leave them.

If you have a vagina as well, a hand there at the same time can be lovely and can also be too much for a first attempt. I add it when the anal bit is already boringly fine.

If it hurts you stop

This is the whole rule. If it hurts, you stop. Not “hurt a bit, that is normal, push through.” A stretch can feel intense, full, odd, even a dull pressure you can breathe around. Sharp, sting, burn, a pain that makes you go polite: that is stop. Come out. Add nothing. Be kind.

I have said “I am fine” while I was not fine, because I did not want to be a fuss and I had already used the evening’s bravery. He believed me. Of course he did. I had used a reassuring voice. Now I say the true word even if it makes me feel ungame. Ungame is how I still like him in the morning.

After a stop: water, a laugh if there is one, no inquest in the first minute. Aftercare is the rest of that minute, not a separate hobby. You can talk later about what the sting was. In the minute, you get out, you get held or not held as you wish, and you do not treat the stop as a wasted evening. The stop is the attempt working.

If pain persists after you have stopped, or if there is bleeding that is more than a trace you can explain, or if you feel unwell: GP. I have been too proud to ring. Pride is a poor clinician.

How we stay clean enough

Clean enough is a shower and a bit of sense, not an operating theatre. I wash. I keep nails short. I do not go from anus to vagina with the same finger or the same toy without soap in between. That last one is a UTI I do not need.

You do not need a ritual enema unless you want one, and even then, gently. Too much rinsing can irritate. A shower, a trip to the loo earlier, a towel: that has been enough for me. A bit of mess is ordinary. You wash.

Condoms make the washing simpler. They also make the oil rule matter. If you switch from anal to vaginal sex, change the condom. People forget when they are hopeful.

The bit I got wrong was treating preparation as unsexy. The later night looked like a slightly earnest spa: shower, towel, plug, conversation. I came out of it liking him more.

FAQ

How do you start anal sex?

Talk first, dressed. Agree what “start” means: a finger, a plug, nothing else required. Shower. Lube like you mean it. Outside, then one slow finger, then wait. A small flared plug if fingers have been easy. Positions where the person being entered can stand up and leave. A word that stops it. If you get nowhere past the outside, you still started. You started honestly.

Does anal always hurt?

No. Intense is not the same as hurt. A first stretch can feel like a lot. Sharp pain is a stop, not a rite of passage. The nights that hurt for me were the hurried ones, or the dry ones, or the ones where I was trying to be game. The nights that worked felt odd and full and then, sometimes, good. If it always hurts, even with time and slip, that is a GP, not a dare to try a larger toy.

What lube is best for anal?

Silicone, often, because it stays. Water-based if you will actually keep adding it. Not oil if you are using a latex condom. Not a numbing cream so you can ignore a warning. I wrote more about types in best lube for sex. The useful version is: more than pride, on the towel, before anyone is hopeful.

How do we stay clean enough?

A shower, short nails, a towel, and soap if you switch from anus to vagina or change toys. Condoms help. You do not need a medical production. Bodies do what bodies do. You wash. If you want more ritual than that, keep it gentle and optional. Shame is optional too. I vote no.

If we get nowhere tonight, we still practised the stop. That is not a failed attempt. That is the attempt I trust.