Let’s start with the number nobody mentions at dinner. A study published in the Journal of Sexual Medicine in 2016 found that around 24% of straight men had received anal penetration from a partner at least once. One in four. And that was a decade ago, before the strap-on market ballooned into something worth hundreds of millions globally, before pegging crept into the top search categories on every major porn platform. The data suggests that a lot of couples are either doing this or thinking about doing this. The conversation in actual bedrooms, though, still tends to collapse before it starts. So let me save you the spiral.
I will be honest: I came to this with more ignorance than I would like to admit. My first serious conversation about pegging happened at a pub in Hackney, not with a partner, but with my friend Jess, who had just bought a harness and was describing the various attachments. I sat there nodding like I knew what an O-ring was. I did not know what an O-ring was. That was three years ago. I know now.
The first thing is the conversation, and it genuinely has to happen outside the bedroom. Not mid-session, not whispered at a moment when somebody is already mostly undressed. That is an ambush, and ambushes make people feel defensive rather than curious. Find a relaxed moment, one that has nothing to do with sex, and just say something like: I have been thinking about trying this, would you be open to talking about it? That sentence does more work than any amount of circling around the subject. If the answer is no, that is a complete answer and you respect it. If the answer is maybe, you are having a conversation. Give it room. Do not negotiate, do not make a case, do not send a link to a Reddit thread at eleven at night. Just let it breathe.
For the person receiving, the preparation is genuinely straightforward, and the anxiety around it is almost always worse than the reality. A lighter diet the day before, using the bathroom an hour or two beforehand, a warm shower. That is it. Most of the catastrophising men do before trying this is based on nothing. Start small: one finger, then a small plug, before anything strap-on-shaped is introduced. Go at whatever pace keeps the receiving partner comfortable. Lube is not optional. It is not a nice addition. It is non-negotiable. One specific thing worth knowing: silicone-based lube will degrade a silicone toy, so use water-based unless your toy is glass, metal, or another non-silicone material. The prostate sits roughly 5 to 7 centimetres inside, angled toward the belly button. Curved or angled toys reach it more reliably than straight ones, which is why that particular shelf in the sex shop looks the way it does.
For the person giving, a harness that actually fits is not a luxury, it is the whole point. A loose harness means poor control and mounting frustration for everyone involved. Budget somewhere between £40 and £80 for a decent adjustable one. Sportsheets and Spare Parts both make solid entry-level kit. The dildo attaches through an O-ring, and this is where Jess’s flatpack energy becomes relevant: check the O-ring diameter matches the base of the dildo before you buy them separately. Many people skip this step and end up on a Sunday afternoon holding two incompatible pieces of equipment, which is funny in retrospect and annoying in the moment. Checking in during is as important as the conversation before. Go slow. Let the receiving partner set the pace. This is not a performance.
Positions to start with are the ones that hand control to whoever is receiving. Them on top, facing away, means they dictate depth and angle entirely, which is both practical and psychologically useful the first time. Doggy style is popular but gives the giver more control, which means more active communication is required to compensate. Missionary with a pillow under the hips is worth trying for couples who want to stay in sync and actually see each other’s faces.
The bit about psychology gets dragged out as though it is a problem to be solved, and I want to be straightforward: a man enjoying anal stimulation tells you nothing whatsoever about his sexuality. The prostate has no opinions about who you are attracted to. Some men are interested in this for the physical sensation, some for the role reversal, and both of those things are completely unremarkable. The couples I know who have folded this into their sex lives without drama are, without exception, the ones who were already decent at talking about sex before they tried it. If that communication is not there yet, building it will do more for you than any equipment.
One thing that somehow never gets said plainly: the first time is rarely the transcendent experience either partner built up in their head. It is usually a bit awkward, requires adjustment, possibly involves some laughing, and ends with both of you thinking that you would do it differently next time. That is completely normal. The people who end up actually enjoying this are the ones who treat it as something to learn rather than a verdict to deliver after one go. Most good sex is like that, honestly. The first attempt is just data.
