I find that it's easier when any (or all) of these points apply. (Note: If these seem "obvious" to you, get over yourself. I'm trying to provide a rounded picture.)

1. Practice. The various suggestions above are good. I find that, if I'm not getting laid, I need to use a dildo or buttplug on myself at least once a week - usually more - just to keep my super-tight hole ready for my luck to change.

2. Smooth hole. When I let my hole get hairy, the hairs will drag uncomfortably on whatever is invading. Carefully shave the area.

3. A thorough enema-type cleanout. There are many reasons to do this; one reason is that the activity itself helps to expand the hole and prepare it for the invasion to come. But be careful to expel ALL the enema water that got into you, before meeting the top.

4. The top's cock being very hard. It's just easier to work it in (patiently, gently with repeated attempts). This is where Viagra and/or young tops have a real edge.

5. Lube. If you're going bareback, you can use a mineral oil product, which is
usually awesome. With condoms, use only lube that was designed for condoms - water-based. The main point is that the bottom can pre-lube his pussy, which is helpful if he doesn't know the top (or exact situation) in advance. But be careful; don't pre-lube so much that you start oozing or expelling it.

6. Bareback. When latex is going in: at least for me, it drags on the surrounding flesh in a way that is unnatural and uncomfortable. When it's bare, I can take a big cock more easily as it feels more natural, more arousing, more intimate.

Naturally, I do NOT recommend bareback unless both parties are on PrEP medication or, if poz, meds for "undetectable" status.

Even poz guys are better off avoiding re-infection with different strains of HIV. Good meds, taken daily, serve poz guys as a kind of PrEP/PEP against re-infection.

So, if you and your partner are not BOTH on PrEP/meds, skip the bareback. Use condoms. Just be sure to practice on dildos, keep a smooth/shaved hole, do internal cleanout, find a top who gets really hard (or uses V), and pre-lube.

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