Message: How Should I Prepare for Anal Sex?

secret-submissive-little: What should i do to prepare for anal sex? i can take a large plug but i dont know how to go from there

You may want to experiment with a penis-sized dildo first, but if you can comfortably wear a large plug for at least 15 to 30 minutes, then you’re already better off than many people who want to try anal.

Before you plan to have anal sex, you may want to wear your plug for a while first to have some initial relaxation. Take a hot shower or bath before, and then ideally have an orgasm before as well to further relax you. After removing the plug, have your partner massage lube into you with his fingers, starting first with a single finger and working up to three or so.

Once he’s able to move three fingers in and out at a moderate pace without discomfort to you, lubricate his penis and prepare for penetration. There are three positions commonly recommended for first time anal: doggy, cowgirl, and spooning. Some work better for some people than others, so if something doesn’t work well, try another. Positioning yourself over him and lowering yourself down onto his penis is my personal favorite for first time anal, because it puts you in complete control over the speed and depth and angle of penetration and lets you stop and rest a moment if things become uncomfortable or painful. You can do a similar thing with doggy if he remains still while you push back.

Once he’s as far inside as he can go, pause a moment so you can get used to the feeling, then slowly move. You can build up the speed, but do it slowly and back off if it hurts. As you become comfortable with the sensations, you can change positions and/or give him more control.

Absolutely make sure your partner understands to stop immediately if you tell him to. If it hurts, you don’t want to keep doing it or push through the pain until it goes away, you want to stop what you’re doing and back off slightly and wait a moment until the pain fades, then try again more slowly and build up more gradually. You don’t need to stop altogether, and as long as you’re careful any pain should fade very quickly if you don’t keep pushing through it. It’s worth taking your time and having a more enjoyable experience rather than causing actual injury and preventing further experimentation for a few days to a week while you heal.

If you do experience bleeding, however, it’s either due to too little lube or going too quickly without being warmed up enough. It can occasionally happen as you start out and learn what you can and can’t do, and while it’s usually nothing serious, it’s almost always best to stop as soon as you notice this and take a break for a few days before trying again, just to avoid causing any actual damage.

It can take patience, lube, and trial and error, but the payout can be well worth it. Keep trying and enjoy.

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