RN
Almost everything worth knowing here follows from two pieces of anatomy, and the folklore mostly exists because nobody mentions them.
The first: there are two sphincter muscles, not one. The outer is under voluntary control — you can consciously relax it. The inner is not. It responds to arousal and time and to nothing you can decide, which is precisely why "just relax" is useless as an instruction and why rushing does not work. The waiting is not a courtesy. It is the mechanism.
The second: the tissue produces no lubrication of its own. None. Whatever moisture is present is not a lubricant, and the surface it is protecting is thin and tears easily. This is the entire reason lube is not optional here in the way it can be optional elsewhere.
Hold those two facts and the rest of this is mostly consequences.
Before anything happens
Anal is one of the acts most often requested by someone who is not the one receiving it, which makes the agreement worth more care than usual — a real conversation beforehand rather than an in-the-moment attempt, and an explicit understanding that stopping is allowed at any point without it being a failure.
It also gets treated as a favour, which is a bad frame. It works far better as something the receiving partner is curious about in their own right. For a receptive partner with a prostate, there is a specific and well-understood source of sensation involved. For everyone, there is a dense concentration of nerve endings around the opening itself, which is why external play is worth exploring first and is often where the interest turns out to actually be.
Preparation, in proportion
Cleanliness anxiety is the most common reason people never try, and it is mostly disproportionate. The rectum is not a storage area; under ordinary circumstances it is largely empty.
A shower is enough for most people most of the time. If you want more reassurance than that, a small amount of plain warm water used gently is the outer limit of what is sensible. What is worth avoiding is the escalation: frequent or forceful douching, soapy solutions, and repeated enemas all irritate the lining you are trying to protect and disturb the tissue's normal state, which makes it more fragile rather than cleaner.
Timing helps more than equipment. Going a few hours after a meal, and having been to the toilet beforehand, does most of the work.
Trim your fingernails. That one gets left out of every guide and it matters.
Lube: which kind, and how much
More than you think, then more again, and reapplied — it absorbs and drags return before anyone mentions it.
Water-based is the safe default. It is compatible with condoms and with every toy material, and its only real drawback is that it dries out, which is what reapplication is for.
Silicone-based lasts considerably longer and is a genuine advantage here. It is condom-safe. It will degrade silicone toys, so it is one or the other.
Oil-based products, including household oils and many massage products, break down latex. If a latex condom is involved, they are out.
One category to avoid outright: anything advertised as numbing, desensitising or "relaxing". These work by removing the sensation that tells you something is wrong. Pain in this context is information, and a product whose function is to suppress it is removing the only warning signal available.
The safety items that get skipped
Four things that belong in every version of this article and appear in almost none.
Never go from anal to vaginal without changing condoms or washing thoroughly first. Bacteria that are unremarkable in one place cause infections in the other. This is the single most common practical mistake, and it is entirely avoidable.
Infection risk is genuinely higher for anal sex than for vaginal sex. The lining is thinner and microtears are common, which makes transmission of sexually transmitted infections easier in both directions. Condoms are correspondingly more useful, not less. If this is going to be a regular part of your life, a sexual health clinic is the right place to ask about testing and about what preventive options apply to you — that conversation is routine for them.
Any toy that goes in must have a flared base. The rectum draws inward; unlike a vagina it does not have a closed end. An object without a base can be pulled beyond reach, and the result is an emergency department visit. This is not a cautious recommendation, it is the one hard rule.
Pain means stop, not push through. Discomfort or pressure that eases as you go is ordinary. Sharp pain is not, and continuing through it is how tears happen.
During
Slow, and slower than that. Start externally and stay there longer than seems necessary — fingers or a small toy before anything larger, and the receiving partner controlling the pace and the depth rather than being on the receiving end of someone else's judgement about it.
Breathing out as pressure increases genuinely helps; holding your breath tenses everything, including the muscle you are waiting on. If it is not working, stopping and trying another day is a completely normal outcome, not a failed attempt.
Afterwards
Wash gently with water and unscented soap. Expect some soreness for a day or so if it was a first time.
A little spotting of blood can happen from a small tear and usually settles quickly. Ongoing bleeding, pain that lasts more than a day or two, or any change in bowel control is a reason to see a doctor rather than to wait it out — anal fissures are common, treatable, and much easier dealt with early. It is a routine consultation and you do not need to explain more than you want to.
And if it turns out you don't like it
Then you don't like it, and that is the end of the matter.
The framing of this act as an achievement — a frontier, a level unlocked, something to be conquered — comes almost entirely from how it is sold in porn, where it is a category rather than a preference. Plenty of people try it, find it uninteresting or unpleasant, and never do it again. That is not a failure of technique or of nerve. It is just information about what you like.