First anal sex (bottom), should I prepare or not?

[Diogenes]

I am planning on finally having anal sex with someone, but should I practice with dildos and/or plugs before going into the real thing? I know a lot of people here don't really plan for this, but my life never allowed me to be spontaneous. I heard that it would be more painful and less enjoyable if you are completely inexperienced, which makes people not ever want to bottom again. I want my first anal sex to be enjoyable and for it to spark something. Any thoughts on what I should do? What are your experiences with this?

[jtgirl2022]

I am in a similar position to you, and think you should definitely prepare and practice first if you want an enjoyable experience. I started with a 6" dildo and then increased to 8" length, about 5" girth. When you start you will need loads of lube and relaxation, much more than you expect, to get anything in.

You need to practice to allow yourself to relax, otherwise you will likely tense up and have a painful/frustrating experience both for you and your top. I am at the point where I can sit on my 8" dildo with a small amount of lube, just rock up and down a bit, and it slips in comfortably without any pain. Hopefully that will be enough for the real thing 🥰

[TommyTheVirgin]

The only thing I used before anal sex was the douche tube when I flushed myself out.

I probably should have used dildos but I wanted my friend to have the ultimate feeling inside me.

And use lots of lube.

Just remember this rule for lube:

Too much lube is never enough.When you think you've applied enough apply more.

And it will hurt.

 

[Iker80]

Getting fucked is about mind over everything else. When you're in the headspace your guy will go in easily because you're relaxed. It's not you're trying to take him, it's you feel empty of him before he even goes in. This isn't something that easily happens first time though, and that's ok. You don't need to get everything perfectly first time for it to be good.

Dildos may or may not help. They're not essential. Many guys, I'm one of them, just went for it first time with another guy. For me, dildos and dicks are totally different. Dildos don't make me horny or excited to be inside me like a guy does, they're just a hard bit of not sexy plastic being shoved in to a very personal space. Zero pleasure, even when I'm the one driving, just lots of not sexy grunting and pain. So you maybe can or maybe can't take a dildo, depends what headspace they put you in. And that's really it, does the guy you want to try with make you want it? If he does, you'll get there. If a dildo sound fun, chances are they could work for you too, but if not they may be unhelpful.

[plisken]

I tend to agree with “Iker80” its much about your mind, you want him in you, need him - and some lube

[norefusal]

On 6/9/2025 at 1:35 AM, Diogenes said:

I am planning on finally having anal sex with someone, but should I practice with dildos and/or plugs before going into the real thing? I know a lot of people here don't really plan for this, but my life never allowed me to be spontaneous. I heard that it would be more painful and less enjoyable if you are completely inexperienced, which makes people not ever want to bottom again. I want my first anal sex to be enjoyable and for it to spark something. Any thoughts on what I should do? What are your experiences with this?

i don't know what ur history is but this is my experience: 

i started out fucking women, not random hook up but GFs. sex always included a lot of foreplay, making out, mutual oral etc so by the time i was penetrating they were all wet n ready. 

my ass is far more like a cunt than i realized. my first top was a lovely, hot guy and by the time he stuck his big d up my virgin ass we'd been talking/flirting and fooling around  for a while so it just slid right in as i wanted it bad by that point. 

in my experience, it only hurts if a guy walks in and just goes right at fucking 0 to 60 with not even a hello first. so no amount of lubed dildo play is gonna do it if your cherry-busting plan is to host door open ass up for anon. 

i can do it now, but that's after decades of being a shameless whore 😜

[Lilyjameson]

Dont douche , keep your gut bacteria, all you doing is flushing out the bacteria that is useful. I prefer this method, not eating too much, just keep yourself hydrated during the day, just dont skip breakfast. Let the guy use condom first, then after a couple of minutes fucking, if he sees that is is perfectly cleaned out by fucking in and out of the ass, then go bare.

[verbalBTTM]

If you tell the guy you're going to hook up with it's your first time 99.9% of the time he will be kind and patient. I've broken in many boys and I spent the time working them open. There's nothing more exciting than giving a guy his first, it's almost like reliving your first time except this time it'll be better. Clean out your butt to the best of your abilities and decide you want this. Set out any limits you might have such as condoms upfront. This will help to put your mind at ease

 

I'd also recommend taking some magnesium since it is a natural muscle relaxer and will help you relax during the initial penetration and continuing thrusts. Also poppers would be good to have on hand, but let him feed them to you. He will know when you'll need them. The biggest issue you'll have is your own head, trust your partner to want to give you a pleasurable experience. 

 

Communication is key, let him know if you have any discomfort, sometimes more lube will need to be applied. Perhaps he's entering you at the wrong angle, things happen especially since you have no experience. 

 

Let go of your fears, trust in your partner and let go of your inhibitions. Please report back with how things turned out.