I said it as a joke by the bathroom cabinet and then had to mean it. He was putting the lid back on a pot of moisturiser. I heard myself do the laugh people use when they want a door left open. Then the laugh sat in the room and needed a real sentence. The first time we tried, it was slow, over-lubed, and better than the joke. We could have stopped. We said that out loud.

If you came here for how to try pegging, that is the shape: a conversation that is not a mockery, more lube than pride suggests, a small start, and a stop that is easy.

How to try pegging when the joke has to become a plan

Pegging, in the way I mean it, is one person wearing a strap-on (or using a toy by hand) to have anal sex with a partner who has a prostate, or who wants that kind of fullness. I have done this with a man. The reader may have a different pairing. The useful facts travel. The prostate sits a short way inside, towards the belly, and can feel like a lot when you are not rushing.

People want this for reasons that are not a personality transplant. Curiosity about a part of the body that was given a joke instead of a map. Wanting to switch who is doing the entering. A fantasy that has been sitting in the drawer with the optimistic toys. I wanted to see his face when he was the one being careful. That is not a manifesto. It is a night.

Who it is for: two adults who have both said they are willing, even if one of them is nervous. Nervous is allowed. Mocked is not.

Who it is not for: a surprise, a dare after a bottle, a "it will be funny" that removes someone's choice. I have been in rooms where a joke was used as a trap. I will not help you build one.

Whether you need a harness on night one: not always. A small, smooth toy and a hand can teach you more than a costume. A harness helps later if you want your hands free and a more familiar rhythm. I started with a slim toy I could hold. The harness came when we already knew the speed.

The conversation, without mockery

Say it in clothes, in a room that is not already mid-sex. The cabinet joke worked as a door. It did not work as a plan. The plan was later, on the sofa, when I said: I would like to try this, slowly, and I need you to want it or say no. Not maybe-for-my-sake.

He asked if I thought he was less of something. I said I thought he was a person with a body that might like a new pressure. The masculinity speech can arrive. Let it arrive. Do not win it. If he needs a week, he can have a week. If he needs a never, he can have a never. Asking again every fortnight is a drip.

Telling a partner a fantasy is a smaller job than a speech. One picture. Their face. A way out that does not make them a coward for using it. If you are the nervous one, you get to name the fear without being talked out of it in the same breath. I have been talked out of a no. It made me polite in bed, which is a terrible kind of yes.

What to agree, in ordinary English:

Who is wearing, who is receiving. You can swap another month. You do not have to swap to make it fair. Fair is both people wanting the night they are in.

How you stop. Stop is enough. If you are the sort of pair who says stop as play, pick a word that is not play. We used red, because we already had it from nights that were only wrists. You can borrow a word from a different scene. You cannot borrow a mood of "we will push through."

What is off. For me: rushing, a size we have not met, anything that treats a wince as comedy. For him: being filmed, being narrated as a punchline to a future dinner. Name the off list before anyone is undressed.

If this sits next to a wider curiosity about power and a word, not a kit, you still start with the smallest true sentence. I want to try a small toy. I want you to tell me if it is too much. I want to be able to stop and still like you.

Do not research him in front of him as if he is a project. I did that with a phone on the arm of the sofa. It felt like homework. He went quiet. I put the phone away and asked what he was afraid of. He said pain, and looking foolish. Both were reasonable. We planned for both.

Harness, size, lube

Size: smaller than you think. Slim, smooth, not a novelty shape. A slight curve towards the belly can help you find the prostate without hunting. Length that will not surprise anyone. I once believed bigger was a gift. It was not. The first useful toy was almost shy.

If you use a harness, try it on before the night so you are not doing DIY with an erection in the room, or with someone waiting on all fours trying to be a good sport. Adjust the straps. Walk to the kettle. See if it stays. A harness that rides up will make you think about the harness, which is the opposite of useful.

Material: body-safe silicone, something you can wash. If you are sharing toys, condoms on the toy are an easy extra. If anyone has a barrier they already use, keep using it. If something burns, you stop.

Lube is not a garnish. Anal does not make its own the way a vagina often can. You want a thick water-based or hybrid lube you can reach without a speech, and then more of it than looks dignified. Silicone lube lasts, and it can wreck some silicone toys, so read the pairing. I keep water-based by the bed and I reapply like a person who has learnt.

Fingernails: short, or a glove. A scratch inside is a night that ends and a week of being careful on the loo. I have been the person who forgot and then spent the evening apologising to a wince.

Shower if you like. A bit of ordinary washing. You do not need a medical production. You do not need to narrate the washing as comedy. He already knows he has a body. Let him have it.

If you want a plug first, a small one, for a short stretch, that can teach the "full" feeling without a rhythm. We did that on a different night, under a film, and it made the later night less of a cliff. It is optional. Some people want the cliff. I wanted the slope.

A first time that can stop

Start with hands. A lot of kissing. Arousal is not a side dish. A tense hole is a hole that will say no even if the mouth said yes. I used my mouth on him first, the way I already knew, until he was actually in the room.

Then a fingertip, wet, waiting. Not a poke. An ask. If the muscle tightens, you wait. You do not argue with a muscle. When it lets you in a little, you stay. One knuckle is information. Two is later.

The toy next, or the same night if the finger was easy and everyone still wants it. More lube. Line it up. Let him push back rather than you pushing in. That one shift (he is doing the taking) is how you keep this from feeling like something done to him.

Slow. Smaller than porn. Porn is a different sport. I moved like I was stirring something I did not want to bruise. He said wait, twice. We waited, twice. The third time he said okay, and the mood went from giggle to quiet. That quiet was the point. I could feel him thinking with a new part of himself.

You can stop at any of those stages and call it a success. A finger and a lot of looking after is a first time. A toy that goes in an inch and comes out again is a first time. All the way, if it happens, is not a grade.

If it hurts in a sharp way, you stop. Burn, sting, a "wrong" that is not pressure: out, water, shirt, kindness. Dull pressure that eases can be the body learning. Sharp is the body asking you to leave. I am not a doctor. Blood that is more than a smear, pain that stays, fever: GP, not a blog.

Positions that have been kind to us: him on his back, knees up, so I can see his face. Him on his side, my chest to his back, so it stays shallow. On all fours only if he likes it and you can still hear him. I like the face. The face tells you more than a hip.

You do not owe anyone an orgasm from this. He might come. He might go soft and still want the fullness. I have had both. I did not take the soft as a verdict on me. I took it as a nervous system doing a new thing.

The bit I got wrong was treating his pleasure as a test I could pass if I found the right angle. I hunted. He went polite. Polite is how you miss the prostate and the person. When I asked him to put a hand over mine and show me the depth, the night improved in about ten seconds.

We could have stopped. We said that out loud, more than once, until it was boring. Boring consent is the good kind.

Aftercare for both of you

He may want to be held. He may want the loo and a minute with the door shut. He may feel oddly shy, or oddly fond, or drop in a way that surprises him. The receiving end of a new intensity can leave a person thin for an hour. I have seen it. I have also been the one who needed the landing, because I had been concentrating and then suddenly I was just a woman with a harness and a lot of feeling.

What I do now:

Get the toy out of the plot. Wash it later if you must, but get it off the bed so nobody is staring at the evidence like a crime.

Water. A shirt. Ordinary sentences. Was that all right. Do you want to be near me. Do you want eggs.

If he liked it more than he expected, let him have that without a joke. The joke is how shame gets back in. If I liked it more than I expected (I did, the quiet, the look of him), I said so. Not as a victory. As weather.

The next day, a small message if you are not in the same flat. I keep thinking about last night. I am glad we went slowly. I would do it again, or I would change the size. Silence is how people invent a story in which they were too much, or not enough of a man, or too much of a woman who wanted something.

If one of you is sore, you rest that part. You do not book a sequel to prove the first night was fine. I have booked a sequel too soon. It was pride. Pride is a poor lubricant.

FAQ

How do you start pegging?

You start with a sentence in clothes, a small toy or a finger, more lube than looks sensible, and a stop you have already practised with your mouths. You do not start with a large purchase and a film. You start with the smallest version that still counts as the thing, and you let it be enough.

Does pegging hurt?

It can, if you rush, go dry, or pick a size that is showing off. Pressure is common. A stretch that eases can be all right. Sharp pain is a stop. I have had a night that was only a fingertip and a lot of looking after, and a night that went further and felt like a deep, specific ache that he asked to keep. Hurt as damage is not the aim. If you are both treating hurt as a score, you are in the wrong sport.

What toy should we use first?

A slim, smooth, body-safe silicone toy with a flared base, smaller than your bravery. A slight curve helps. A harness is optional on night one. If you already own something that fits that description, wash it and use that. The fancy kit can wait until a night has asked for it.

What if he likes it more than I expected?

Then he likes it. That is information, not a crisis. You do not have to make it his whole personality, and he does not have to make it yours. If you feel odd about the shift (who is entering, who is being careful), say the oddness. I felt tender and a bit powerful and then I wanted a sandwich. All of that was allowed. If you liked it less than he did, you still get a vote on the next night. His pleasure is not a contract.

I still check, even now, that the stop is boring and the lube is ridiculous. The night I trust is the one that can end in the middle and still be a night we would both choose again.