So you're thinking about trying anal sex. Awesome. Presumably you've already discussed it to a degree with your partner (or you could be wanting to experiment alone- that's legit) and now you're wondering how to get started. Obviously everybody is different and you'll work at different paces with different finish lines but for the most part here is a handy little guide to get you going. And no, watching porn has not prepared you for the reality of anal sex, so please don't start where they do.
First of all you're going to need to communicate. You already established that it would be hot? Yeah, communicate more. The reality is that there are certain issues to be navigated with anal penetration that you don't necessarily have to deal with when having oral or vaginal sex. The first is some prejudice- no anal sex doesn't make you cheap, no it isn't necessarily better than other forms of sex, no it isn't any "further" than other forms of sex, no it's not gay if you're a guy and want to experiment with it (unless you're a gay man, but my point is using that hole doesn't indicate sexuality). Then there's poop. Now, if you're prepared there shouldn't be any poop, but you still need to communicate in case there is. Talk about it and figure out somewhat of a game plan. If you'd be most comfortable laying down a towel then do that, if you'd like to use condoms just in case (if not already using them for protection) then do that, if you'd like to keep wet wipes by the bed then that's also a good idea, but the most important part is that you have a conversation about it so that, if the worst does happen, at least you know this person shouldn't have a full blown meltdown and you can probably trust them to be mature about it. You want someone who can laugh with you in the shower about it rather than hyperventilating.
Next is lube and toys- if you want to use toys then you'll need to talk about what everyone is comfortable with, and you're going to NEED lube so you should probably talk about the logistics of getting some if you don't already have it (and if you don't own lube then please invest in lube, I'll write another post all about it but just please own lube).
So you've spoken some more and established some boundaries, you're both comfortable, and you know what you need to get started. Or, if you don't quite know, here are some good toys for beginners:
Butt Plugs: These can come in a variety of sizes, I'd recommend starting small and working towards larger ones, and are great for getting used to the sensation of fullness. They can provide a lot of sensation if they're of the vibrating variety or being manually moved, as well as when worn during regular sex. I'd recommend a starter kit like this one
Anal Beads: Similar in terms of the impact of a Butt Plug, Anal Beads are great for a slow start getting used to insertion (perfect for getting the hang of relaxing) and can be extremely filling and intense when moved. Some people also love the sensation of them being pulled out at the point of climax. I'd recommend something simple like these
Dildos/Strap-ons: If you're looking more towards pegging or using dildos I'd recommend starting with a smaller option than you'd probably see in porn, and there are dildos made specifically for your butt. These are often smaller, smoother, and generally less intimidating, and most harnesses you'd be able to switch to a bigger toy with, so it's pretty win-win. I'd recommend something like this
I'd also say that a good starting point is using your fingers and remember PLENTY of lube.
You've had your talks, you've got your setup, you've stocked up on lube and whatever toys you fancy, and now it's time to get to business, here are some tips to help you on your way:
Poop a couple hours before you plan on doing anything- this should clear your system and, unless you're going a lot, you shouldn't have anything hanging around to mess up your fun (no pun intended)
Start with foreplay as usual- you're always more relaxed when you're turned on so don't go straight for your butt, whether you're alone or with a partner make sure you get yourself in the mood
Start slow and small- you're not going to be able to fit a penis or any sizeable toys in your booty from the offset so this is a good time to play with any smaller toys you have or use your fingers. if starting with toys start with the smallest and work up, if using fingers start with one and add more at a pace that is comfortable. Remember to use plenty of lube (obvs).
Don't rush the warmup- the reason they don't show you all of this in porn is because it can take a while. I mean it shouldn't take hours, but it can take a little while, you're waiting for your body to relax and the longer you spend building up the better it will feel.
Take deep breaths- the more anxious you are the less your butt is going to relax and let things happen so just try your best (as impossible as that sounds) to just ease into it, remain calm and enjoy the sensations.
Find a good starting position- I'd recommend on your side with one leg down straight and the one on top at a right angle in front of you (kind of like when you wrap a leg around your duvet or a pillow) as you're probably going to be holding very little tension in your body like this and you're still facing your partner enough that you can see each other to communicate better. Try to find a position that works for you but in my experience this seems to work best for most people I know.
Keep communicating- Just because it feels good for your partner doesn't mean you have to be uncomfortable. This should be enjoyable for everyone and if things stop feeling good say something so you can dial it back. If something hurts and you don't address it you'll just tense up more, it'll hurt more, and you could do yourself some damage.
Stay clean- If you're going to switch it up and go for oral or vaginal sex please don't just go from one hole to the other. It may look clean but there could still be bacteria so it's always best to wash things up first unless you want the worst UTI of your life.
Aftercare- if you've gone about things the right way there shouldn't really be any pain afterwards, definitely no blood, and things will bounce right back. Make sure you have a debrief with your partner, go over how it was for both of you and be honest- communication doesn't end when the act does.
And that's about it! Remember, just because you did it once it doesn't mean you have to commit to doing it again unless you want to, but if you do want to do it again then I'd recommend the same steps- still start slow, still use ALL the lube, and still communicate throughout.