About to have first time anal sex?
Welcome to brand new sensations, new ways to connect with lovers, and (hopefully) a pretty amazing introduction to the power of the prostate!
We get it though: there are a lot of worries, stereotypes, and anxiety that can surround having anal sex for the first time. As a top, you might be worried about staying hard, the mess, or hurting a partner. As a bottom, you might be worried about being able to take your lover, the mess, or potential pain.
Today, we’re here to help: we’re going to cover all the basics for amazing first time anal sex. Let’s jump in.
How to Prepare for First Time Anal Sex as the Receiver
Having anal sex for the first time as the receiver can be anxiety-inducing! While we’d guess you’ve had some anal experience solo, sharing that intimate space with someone else can be unpredictable and vulnerable.
There are a few tips we’d recommend to help it go as smoothly as possible:
Be comfortable with anal penetration. There’s a lot that goes into pleasurable anal sex, and it can be hard to make it amazing if you’re brand new to all penetration the first time you try to have anal sex. Instead, make sure you’ve spent multiple sessions sliding in your fingers. Ideally, you’d also have experience with a dildo or two to better match your future partner’s proportions. Not only does this make for more pleasurable anal sex when you eventually have it, it also gives you the familiarity to make sure you can speak up for your own needs.
Understand your own anal hygiene needs. An enema clean-out isn’t required to have anal sex, but some bottoms prefer it. If you’re someone who does, make sure you’ve practiced your enema clean-out a few times before you meet up with your top. A poorly done enema can actually make messes worse by dislodging material that wasn’t in the area in the first place. Make sure you’ve gotten familiar with achieving the results you want from your enema.
Speak up for yourself. If your top doesn’t know it’s your first time, they may have expectations that you’re unaware of. For example, some practiced bottoms will arrive at any playdate already warmed up and plugged, ready to go straight to sex when they walk in the door. Letting your top know that you’re new to this – and making sure to advocate for your own pleasure and safety throughout – are important to having a good time.
Stop if it hurts. A temporary, somewhat-uncomfortable stretching sensation is normal for anal sex. Sharp pain is not. If you’re feeling sharp pain, make sure to speak up. You likely need more time to warm up and stretch yourself out before attempting your top’s size. This is especially likely if your top is very well-endowed.
How to Prepare for First Time Anal Sex as the Giver
We’ll give it to you: being on the receiving end of anal sex for the first time is much more nerve-wracking than being the person sliding into someone else.
That being said, there are still some things you can do as the giver to help make a newbie bottom feel more comfortable.
We’d recommend:
Encouraging your bottom to have a warm-up toy. Depending on how new your bottom is, they may not think about doing a warm-up before you show up. Encouraging your newbie to gently open themselves up with a sex toy can make for easier penetration on your end. You can easily turn this into foreplay, requiring “proof” and erotic photos from your bottom for easy flirting.
Picking a position that makes for comfortable patience. While your newbie bottom has probably slid things up there, they may be new to the feeling of a large person pressing up against them. Pick first time anal sex positions (like some mentioned below!) that makes it easier to hold yourself at partial penetration to give your bottom time to get used to your length.
For example, the flatiron position may not be a good fit as it requires you to partially hold a plank during initial penetration. The right sex position also has the benefit of being a position where you can take the time you need to achieve the erection you need to slide inside.
Bringing mess prevention gear…just in case. You or your newbie bottom might be worried about any resulting “mess” – especially if they’re trying to impress you. You can help reassure them by bringing gear that makes for easy mess clean-up. Puppy pads, disposable gloves, and condoms can all reduce how much “mess” a nervous bottom may be exposed to. You can easily swap out, fold up, and toss any barriers that get “mess” on them, reducing the need to touch any messes yourself.
Don’t freak out about a mess. If you’re an anal sex pro, you know that messy anal happens sometimes. It happens even more when you’re new to receiving anal and may be nervous or new to anal clean-out practices. Make your newbie’s first experience smoother by shrugging off any resulting mess. If any mess squicks you out too, consider using condoms, gloves, or other barriers to keep it away from your own skin.
How to Have Anal Sex for the First Time
The steps to pleasurable, orgasmic anal sex are relatively few, but it’s important that you follow each one. We want your first time to be as pain-free and pleasure-FULL as possible!
Our how to have anal sex for the first time steps:
- Be Turned On: The body is so much more relaxed when it’s turned on. Plus, everything feels better! Make sure you’re turned on and literally (and physically!) excited to slide things in. It will make everything else feel better!
- Don’t be in a Hurry. If you know you have to make a meeting in 30 minutes, it’s probably not the time to have anal sex for the first time. Rushing your body (and the process!) will put some mental and physical strain on you, making it harder to relax and have a great time. We want you to have a great time!
- Use Lube. If anything goes up the bum, it needs lube. It needs LOTS of lube. In an absolute pinch, saliva is a bare minimum, but we recommend lube made for sex in (literally) every circumstance. Spit just can’t compare. Lube reduces unpleasant friction, and it drastically reduces the risks of anal tearing. Yes, tearing your butt is possible, and no, we don’t want it to happen. Use lots of lube on anything that goes in there, and when you think you’ve used enough, add more for good measure.
- Warm Up with Smaller Toys. Going from zero to “penis” can be a lot on anyone’s hole, and it’s especially hard if you’re brand new to anal sex. Before your partner slides in, warm up with smaller items. Smaller-than-your-lover dildos are the best choice as they can warm you up for both depth and width, but fingers can also work if you don’t have any sex toys around. Spend a while warming up the area, gently stretching it (while simultaneously getting some great foreplay). Once your body feels like it wants more and you find yourself pushing back into the warm-up toys, you might be ready to move on.
- Go Slow with Initial Penetration. When your lover goes to slide in, make sure they go slow. The first couple of inches are probably going to be the biggest stretch, and depending on how thorough your warm-up was, it might take 5 minutes (or longer!) for your body to adjust to your lover’s shaft size. Make sure you both are in a position where your top can maintain that shallow, partial penetration until your body goes from feeling “uncomfortably stretched” to “pleasurably full”.
- Don’t Be Afraid to Tap Out. The reality is: your body may not be ready to have anal sex today. Even if you do all the “right” things, you might need more weeks of warm-up, you might be too stressed to relax, or your top might just be really well-endowed. If you’re finding pain no matter how you try to do things, don’t be afraid to tap out. Having anal sex for the first time is supposed to be enjoyable – not painful!
- Speak Up for Yourself. When all of these sensations are new, it can be hard to suss out what’s great and what is just lukewarm. As hard as it is, try to speak up for yourself. If you think a different pace would feel better, suggest that. If it makes you feel better, frame it as an erotic request like “Oh fuck, can you try doing X? I think it’s going to drive me insane.” Most of us want our lovers to feel fantastic, and you’ll find most tops are happy to oblige.
- Have Fun! Having anal sex for the first time is supposed to be fun! While following the “rules” for safety and pleasure, don’t forget to have fun. Sex is about pleasure, connection, and ridiculously amazing orgasms. Don’t lose track of that by setting goals (such as “I have to have first time anal sex before the end of this year”).
Best Position for First Time Anal Sex
We’re looking for a few things when we look for the best position for first time anal sex. Namely, any position you choose should be:
- Easy to hold during initial penetration. Whether the newbie is a top or bottom, pick a position that makes it easy to be patient during the first couple of inches. The top may have performance anxiety, and they might need a bit of solo hand time before being able to slide in. The bottom may feel the stretch more than they expected and need some long pauses as those first inches go in. Choosing a sex position that helps support both of those makes it easier for everyone.
- Avoid straining either partner too much. Whether it’s the top or bottom’s first time having anal sex, acrobatic sex positions can add a lot of complexity to the challenge. That’s not necessarily a good thing. Pick a position that allows the newbie to focus on having anal for the first time.
- You might also want to choose a position where you can see the first timer’s face, but that’s entirely a personal preference. We think it’s hot AF to see those levels of ecstasy as they experience butt play for the first time, but you don’t have to agree with us there. 😉
For us, personally, we think some of the best position for first time anal sex are:
Doggy Style
We know, we know: it’s so basic. But it’s great for first time anal sex for a big reason: it’s really comfortable for everybody to maintain. The top can slide in by millimeters without needing to hold a plank. The bottom can pull away (or push into the top!) as needed to help control the depth and showcase when they’re ready for more. If there’s any resulting mess, the bottom doesn’t necessarily need to know about it. Best of all, if the bottom wants that reach-around, it’s easy for either partner to add it in. We even have an entire doggystyle guide about it!
The only downside: it may not hit the bottom’s prostate as reliably as some other anal sex positions.
Eiffel Tower Position
If your heights match up and you can find a piece of furniture for the bottom to rest their upper body on, the Eiffel Tower position is your “adventurous” best position for first time anal sex. It’s just a bit like a standing doggy style. You both get the “vibe” of having gotta-have-it-now standing sex while maintaining all of those amazing benefits from doggy style.
The only downside: if anyone isn’t used to having an orgasm while standing, it might be hard to get off like this. To maintain the “hot” while still making for easier orgasm, consider transitioning to a regular ol’ doggy style when it’s time to cum.
Cowboy or Cowgirl Sex Position
This one gets mentioned often as a great first time anal sex position, and it’s for good reasons: the bottom controls the depth and pace, you get hot AF eye contact, and it isn’t too complicated.
The biggest downside: this can be really hard on the bottom’s knees and quads. If you have a sex swing, wall, or couch that the bottom can use to help support their upper body weight, that can really help here. If you’re the athletic type, a set of olympian rings can be perfect for this.
Grand Slam Sex Position
If the bottom’s really craving that vulnerable feeling of being “ridden”, the Grand Slam sex position makes it easy for the bottom to lie down and just enjoy the ride. A comfortable straddling position means the top can slowly slide in without quaking muscles while the bottom doesn’t need to see any resulting mess (if it happens!).
This position can also be great if the top is the one who is having first time anal sex: with the bottom facing away, the top can take the time they need to give themselves a “helping hand” without the bottom partner necessarily watching.
The biggest downside: the top REALLY needs to behave themselves. This position makes it really tempting to really “ride” the bottom, and this can only work as a best position for first time anal sex if the top is willing to go at the pace the bottom needs.
The Bottom Line on First Time Anal Sex
If there’s one “secret” to first time anal sex, it’s this: your body sets the pace, not your ego. Prep helps, lube helps more, and patience helps the most — and when you treat the whole thing like a slow, hot build instead of a performance, it usually clicks. Keep communication sexy (“slower,” “stay right there,” “more lube”), take breaks when you need them, and remember that tapping out is still a win if you learned what feels good. The goal isn’t to “complete” anal sex, it’s to have a good time, feel safe, and leave the experience wanting more.