Anal Sex 101: 10 Tips No One Ever Told You

This is your no-shame, no-BS guide to anal sex.

In this quick solo episode of The Law of Cassidy, we’re breaking down one of the most Googled — and least properly talked about — topics in intimacy.

No awkwardness. No misinformation. Just real, practical advice.

💋 Why communication BEFORE matters more than anything
💋 The #1 mistake people make (and why it ruins everything)
💋 How to actually make it comfortable (and enjoyable)
💋 Lube, warmup, and why rushing = disaster
💋 What “going slow” really means
💋 How to avoid pain (and when to stop immediately)
💋 Hygiene tips that remove the anxiety
💋 Why control should be in the receiving partner’s hands
💋 What to do after (yes, aftercare matters)
💋 Real DM questions answered (fear, awkward moments, and more)

Anal is one of the most misunderstood experiences in intimacy — and because no one talks about it properly, people either have bad experiences… or never try something they might actually enjoy.

This episode fixes that.

No shame. No pressure. Just education.

If this helped you — send it to your partner (or a friend 👀).

Transcript

SPEAKER_00 0:00

Hey guys, welcome back to the Law of Cassidy. Today's a quickie. You know how these go. Quick, short, straight to the point, starring me. Party of one. And I wanted to do the huge. We're gonna do the confessions and the DMs. We're gonna do some covet this, share some good products, and um, we're also gonna do um, I'm gonna talk about something new that I'm doing. I am starting a live shopping dynamic. We'll talk about that in a minute. But the main part of this episode, we're gonna talk about anal sex. Dun dun dun. I know some of you just looked around to see if anyone who's watching you listen to this. Put on your headphones, make sure there's no one under the age of 18 in your vehicle if you're driving. Um, and listen up because nobody can hear in your headphones. So, you know, we're gonna respect your privacy, but I am going to go over anal 101, everything you'd like to know about butt sex. Here's the thing. Animal sex is one of the most Googled, most whispered about, and least properly discussed topics in intimacy. And in almost two decades, the space in this actual space, I have answered every version of this question. So today we're gonna do it properly. We're gonna go over 10 tips with zero shame, real talk, buckle up. We're talking about butt stuff. So it's a quickie, just me. Let's go. And like usual, welcome to the Law of Cassidy, where we talk intimacy, business, power, healing, and conversations most people are too uncomfortable to have, which today's conversation would be that butt stuff. Okay. Um, I'm Cassidy, entrepreneur with wife, mom, and someone who spent nearly two decades in the intimacy space. If you, if someone sent you to this podcast, you're in the right place. This one's for the vain ones. You guys know why I call you that because it's just all part of the whole aura of the law of Cassidy. So before we get into the tips, I want to say something. Okay. So anal sex is more common than people admit. It is also more misunderstood than almost anything else in this intimacy space. And because nobody talks about it properly, it's not like you learn about it in school. You're definitely not getting info on it from your parents when you're getting the talk. Um, you don't love to go into the creepy store and ask the weird dude. Okay. You're just not getting the proper information until you find me. And so I'm so glad you're here. Um we're gonna talk about it without shame, without jokes, at someone's expense, without making it weird. People either go complete go in completely unprepared, or they never try something they might actually enjoy. Yes. Trust me when I say this. If you do it right, it is quite enjoyable. So both outcomes are avoidable. So consider this your no nonsense, no judgment, actually useful guide from someone who has been in this space long enough to have heard every single question. I've heard every single question, every horror story, and every really good outcome. So 10 tips. Let's get into it. You didn't know we were gonna talk about stuff today, but that's what we're talking about today. So, number one is have the conversation before the situation. This is so important. We're going back to the communication thing, guys. Tip one, you have to talk it out, okay? Nothing kills a vibe faster than a surprise plot twist. So, yeah, gentlemen, I'm talking to you. No more of the oops wrong hole moments, okay? We're discussing this. This is not a we'll just see what happens activity, okay? This is a, we talked about it over wine first. We made a plan, we're all on the same page, okay? I cannot stress this enough. Consent, curiosity, and communication have to happen outside of the moment, okay? Not in it. Not a spontaneous suggestion, not a subtle redirect, a real conversation before, okay? If you're gonna be bumping uglies and you're gonna be putting things in someone's butt, you need to be able to have a conversation, okay? What are you both curious about? What are your boundaries? What is a safe word? What does yes mean and what does stop mean? Have the conversation, then have the experience in that order, always. Okay? Perfect. On to tip number two. Lube is your VIP guest and is not optional. Okay. Not a suggestion, again, not something you reach for halfway through. Lube is the guest of freaking honor who arrives first and stays last. This is not the time to be conservative, okay? I want you to be generous. More lube is better. Backdoor does not produce natural lubrication, okay? You need it to be abundant, you need it to be slippery, you need to feel like, oh my gosh, this is an enormous amount of lube. You are probably just right at that point. So, unlike the vagina, which self-lubricates, the anus does not, which means you are entirely responsible for creating the right environment because it's not going to be created anywhere else. And the right environment requires a shit ton of lube, okay? A lot of it. More than you think, and then add just like a little more. So for anal specifically, silicone-based lubricant is your best friend. It lasts longer than water-based, it doesn't absorb as quickly, and it means fewer interruptions. Just know, silicone lube is not compatible with silicone toys. So if you're using a toy, check the material first. You'll thank me later for that. But in general, lube. Generously, every single time, no exceptions. So, gentlemen, no, you cannot just slip it in the wrong hole. Okay. We should turn that into a drinking game. How many times am I going to say this during this um podcast? You need lube. Okay, tip three. Warm-up is not optional. It's four plays over achieving cousin. Okay. Start externally, build comfort, ease into it. Lots and lots of manual stipulation, stimulation before anything else. I talk about this in my videos, but they're so short-winded because they have to be on social media. I part of enjoying anal sex is being fully relaxed and trusting to let go. If you are not relaxed, everything's going to be tight, tense, and uncomfortable. The best way to become fully relaxed is to actually orgasm other ways. So stimulate your clitoris, get there. Like maybe you're having that penis and vaginal penetration first, because you never want to go front door to back door and back to front door. Once you go to backdoor game over, it's backdoor, okay? No swipping, just trust me on that one, okay? So um lots and lots of foreplay, lots of fun before. You want to be loose, you want to be relaxed, you want the endorphins like flowing, everything's good. Because if you're tight, tense, scared, uncomfortable, it's not gonna go well. So the muscles back there need to be invited, not ambushed, okay? External massage first is great. When the body's relaxed and receptive, you work inward, slowly, gradually, with full consent at every step. Listen, gentlemen, you have to like it, like has to adjust to you or the toy. So you cannot be going in and then just pound it in, okay? I I call it the inch by inch, and then you get all of it. So a little bit, breathe through it, see how we're feeling, a little bit more, breathe through it, see how you're and then you'll get to the point that you can actually be doing the normal motion, but you've got to almost like let your body adjust to it. So, gentlemen, this, do not do this, okay? We're easing in slowly, and then you can get more movement, okay? So if you're new to this, begin all beginner anal training kits or slim plugs are genuinely the move. Um, it just kind of gets the area used to it. They allow your body to adjust gradually. It's on its own time without pressure. The Love Ends app controlled toys are a great option here. I talk about this, I I use the word comment starfish because this is an app controlled one. It is very thin. Um, so it's not too much. It's great because you can have her wear out on date night. So we're stimulating the area, we're getting the area ready. Okay. They're designed specifically for this. They're body safe, and the app control means the receiving partner stays completely in charge of the intensity. More on that in tip six. We'll get there. Okay. Bottom line, pun, absolutely intended. Warm-up is not skippable, okay? You don't go run a marathon without stretching. You need to have foreplay and stimulation before you go pound town in the back door. Okay. It is the difference between a good experience and a never again experience. And I know many of you are listening and you're like, oh, I've had a never-again experience. Yeah. Okay. We just need to do the warm-up, okay? Four, relaxation is everything. So clenched equals nope. Relaxed equals, oh, okay. I'm I'm here for this, okay? The single bet biggest barrier to a good experience is tension, as it is with anything, okay? And the single biggest cause of tension is not being prepared. So mentally or physically, I always say your brain is like the biggest sex organ. So you need to have this like wavelength of I know what's happening, I know I'm prepared, I know I'm using the proper tools to ease into this. Okay. So deep breathing, I also recommend a warm bath beforehand. Creating a genuinely relaxed environment before anything starts is definitely essential and very helpful. Okay. So, and if you want a glass of wine and that helps you relax, maybe a couple shots of tequila, I don't care. Um, fine, one glass, maybe two. Um, a glass is not two bottles because two bottles is a recipe for what I can describe as a situation. Literally, you guys, nobody wants poop involved and nobody wants that. Okay. So just no, okay. Relaxation is not just physical, it's mental. So you need to feel safe, comfortable, and genuinely into it. If any of those things are missing, your body will tell you and you need to listen to it. And both the receiving, the giver, and the receiver, we all need to be on that same wavelength of communication, of consent. Gentlemen, if she taps out and you were almost all the way down to Browntown, like this is something you gotta ease into and stimulate. So don't get your feelings hurt. Don't throw a man fit, okay? You gotta ease into this, okay? Tip number five, slow is sexy and necessary, which I kind of dabbled into this. So if you think you're going slow, dudes, I need you to go like 30% slower. And I know I've said before, like, if you're doing something right with her and she's like, don't stop, don't stop, don't stop. Men have a major problem with like changing an angle or doing something different in the moments where you just shouldn't stop. Well, this is one of those moments that I need you to stop. Actually, you need to like go very slow. We're talking like you're slow, okay? We are not a fast and furious movie. This is more like a slow jazz playlist situation. You can even put on some music, may make it funner. Um, Miles Davis, not a car chase, okay? So speed is the enemy here, literally. So anything you've seen on a porn video that does not know. That's a hard no, okay. Slow allows those muscles to relax and adjust. Slow gives the receiving partner time to communicate. Slow is actually what makes it enjoyable rather than painful. So if you're rushing, you're doing it wrong. Slow down and then slow down again again. We are like granny slow. We're slowly and then you can increase pace as everyone is comfortable and enjoying it. Okay. Tip six is let the receiving partner be the CEO. This is very important. Okay. Control equals confidence equals a better experience for everyone involved. If someone is going in that direction, they should actually absolutely be in charge. Okay. So this means the receiving partner is gonna set the pace. The receiving partner communicates what feels good and what doesn't. Okay. The receiving partner says more or less stop, different angle, wait, keep going. Okay. It's really important with anal. And I know other way around with penis vaginal penetration, totally different situation. This you have to, I need men, please block out everything you have learned in porn. It is not reality. This is how you have to do it. Okay. So the giving partner's entire job is to follow the lead, literally. Okay. Without rushing, without pushing past what's been communicated. This is not passive experience for the receiver. They're actively in charge. They have to be. This is how it stays safe and comfortable for all parties. And this is the difference between, wow, that was amazing and like a horror story, because I've heard all of them. Okay. And when the power is respected, the experience like transforms for everyone entirely. Okay. Tip number seven: hygiene equals peace of mind, not perfection. Okay. You do not need a full hazmat suit, okay? You just need to feel fresh and comfortable. That's it. A shower beforehand, I like to consider that baseline. If you want extra confidence, gentle cleansing tools or an anal douche are available and completely fine to use, all available on my website. Shameless plug, okay? They're not required. But if the anxiety around hygiene is what is stopping you, there are tools for that. And I'm here to tell you your body doesn't just hold poop there. Okay. When you have to go, it goes to the bathroom. So I know everyone just thinks there's poop there. There's not. There's only poop if you need to go to the bathroom. So also go to the bathroom, okay? Um, toys are actually safer and cleaner than your fingers in this department. Fingers have hangnails, fingers have edges. Save your manicure and use the right tools for the job. I love the bang thrusting plug, also shameless plug, available on my website. And while we're talking hygiene, if you're gonna get waxed for this, please, for the love of everything, wax it all, okay? Not just the front, because if you only wax the front, you will be a proud owner of a genital mullet, okay? So you gotta get if you're gonna do the whole vagina, all the things, you need to actually just get a whole Brazilian. Just get the booty hole too, okay? It's just worth it. Okay. Business in the front, party in the back is not the vibe we're going for. So I need you to wax all of it or none of it. You're welcome. Okay? Tip number eight pain is a red flag, not a challenge, gentlemen. Okay. This is not a push-through it moment. This is not a it'll get better if we keep going situation. Pain needs stop, adjust, communicate, or end the activity entirely. This is a main reason why I do not recommend anything with a numbing agent on the back door. Because if you are numb, one, it can pass on to him and he'll be numb. Or two, you're not gonna feel pleasure and you're not gonna feel pain, which completely defeats the purpose. There are things that help aid with relaxation, which can be used, but we are not let's just keep going when there is pain. We need to feel the pain so we can adjust, okay? This is pleasure, not a crossfit class, okay? Nobody gets points for suffering. You will cause more damage if you just push through, okay? Pain during anal sex usually means one of three things: not enough lube, not enough warm-up, we're going too fast. So back to our previous tips. Use all the lube, make sure to warm up and slow down your roll. Okay. All of these are fixable, but only if you stop and address them, not push through them. Hence communication. Okay. If pain persists, even with proper penetration, that is worth speaking to a doctor about. There are medical reasons that can make this uncomfortable and they deserve attention. Okay. Listen to your body. Also, I am not a doctor, therefore, I do not give medical advice. So try at your own discretion. Okay. But the default position is always pain needs pause, not push. Gentlemen, are you listening? Slow your roll. Okay. Tip number nine protection keeps things simple and safe. So condoms are your friend here for cleanliness, for safety, and for making transitions between activities significantly less of a production. Sexually transmitted infections can be transmitted through anal sex. Condoms significantly reduce that risk. This is not a lecture, it's just an actual fact. Google that shit, okay? Also, and I say this with love, if you're transitioning between anal and anything else, condoms make the hygiene situation dramatically simpler. Um, change the condom, move on with your life. You're welcome. Okay. Simple, safe, easy cleanup. Three reasons, and they're all good ones. So um protection just keeps it simple, safe, clean, and you'll thank me later. Tip number 10. After care is underrated and actually very essential. Okay. Check in, cuddle, laugh, normalize the moment. What did you like? What didn't you like? What felt good? What didn't? Do you like being stimulated with a vibrator while it's happening? These are great, healthy, open conversations. Stop making this situation taboo. You just stuck your dick in her butthole. You need to be able to talk about it. Okay? Yes. Okay. After any intimate experience, especially one that involves a vulnerability and trust like this one, you have to come back to each other. You got to make sure your partner's okay. You ask how they're feeling, you hold them if they want to be held, etc. And if you laugh because something funny happened, our bodies make weird noises, okay? Because sometimes funny things happen and it's normal. And if you can laugh together, okay, you're doing intimacy right. It doesn't all have to be so hush, hush, taboo, like shameful dynamic. Okay, we're wanting to bring more connection. And if you can't laugh together after you're doing intimacy wrong, that's a crow. That's just a quote I just made up, I guess. So write it down. Okay. So I'm gonna give a little shameless plug. You guys know many of you have followed me for years. Many of you have attended parties with me. I love interacting with all of you. The hardest part of what I do is I have been put in this box, and it's anything that has to do with intimacy, sexual pleasure, um, sex, sex toys, like connection. It literally, I get the crap beat out of me on social media. They just hide it from the world. The funny thing is, is if it has to do with men and prostate or erectile dysfunction or um, you know, premature ejaculation, like they can run all the things on that. If it's anything to do with women, they like just totally like hide us from the world. So that's why I came up with this live shopping. We had our first one last week. It went very well. And the best part is is I can say penis, I can say vagina, I can say clitoris, I can say all the words, and I'm not getting in trouble for it. So it's a safe place for you to come. You can actually do shopping, usually lasts anywhere from 40 minutes to an hour, and you get educated, like you're at a party, you're at a live event with me. I can talk more in depth about the products because when I'm doing content or reels on social media, it's so minute bite-sized pieces. So if all this anal stuff has you curious, you're gonna want to actually see the products I'm talking about. Touch them, ask questions, real time, like have a live shopping event coming up. Okay. So we're gonna go deep on all of this, all the anal products, lube, toys, everything with zero judgment. Um, so make sure to register. You can go on my website, castybi.com. You'll see a live shopping event. You can register for the SMS and it'll remind you. You just watch it on your phone. You can just like literally, it's like QVC product pops up, you can tab it, add it to your cart. It's so fun. Okay. So don't miss it. And I'm gonna do these a lot more. We're gonna start making them real. They're gonna be themed. It's gonna be a really good time. Okay. So we're gonna jump into some confessions in the DMs because, like I said, this is a quickie. I don't want to keep you too long. So the first one is Cassie, I've been curious about anal for a while, but honestly, I'm terrified. That's what she said. I literally get this message like all day, every day. Like, what if something goes wrong? What if it hurts? What if it's a disaster? My partner wants to try it, but I keep saying no because I'm scared. How do I get past the fear? So, first, the fact you're curious means something. Congratulations. Okay, the fear is normal and it usually comes from one place and it's not having enough information. So have the conversation with your partner first, outside of the bedroom, like we discussed. Okay. Um, tell them you're curious and nervous, but you want to go at your own pace. Then you want to start with just exploring that area, no pressure, no destination, external massage, a slim plug, your own solo exploration first. The fear shrinks when you feel in control. And like I've said it time and time again, we deal with this so much in the culture in Utah, is it's like there's so much shame about owning your own pleasurability in your own body. It's really important for you to understand your body and what you like. And this is true with anal play too. Okay. So the fear shrinks when you feel more in control, you understand your body, and you're always in control. So that's non-negotiable. Okay. So DM number two is my husband keeps asking about trying anal for two years, and I keep shutting it down. Every bro does, okay. It's like it's like they feel like it's always gonna be no, so that's why they want it so bad, is the way that my husband explained it. But I don't always say no, but you know what I'm saying, it's like this taboo thing, and that's why they always want it so much. So if you don't know where to start that conversation without it becoming a whole thing, let's talk about it. So two years is a long time to be like discussing this and not moving forward. So here's how you start outside the bedroom again, not right before or after or during sex. Um, say, I know you've been curious about this, and I want to have an on. Conversation about it because conversations about sex are important, guys. That's what I'm trying to teach all of you. Okay. Um let them share what they're curious about, share what you're curious about. It doesn't have to be this whole thing, and then maybe discuss how you can start exploring together. You might be surprised what comes out of it. Okay. Last DM because this one was funny and I wanted to share it. So something went wrong during our first attempt, and now we can't stop laughing about it. And it's and honestly, we haven't tried again because every time we think about it, we just start giggling. Is it normal to traumatize yourself with laughter? Okay. This is the most wholesome DM I've ever received, and I love everything about it. So this is completely normal. Um, something funny happened. Things get awkward during sex. If you're laughing and giggling about it, that means you are trusting each other and you are in a safe place. Okay. So that's actually a good thing. The giggling means you're comfortable with each other. Use that. Wait until the giggles pass or don't giggle through it. I don't know. Try again. Sometimes the funniest moments become the best stories. And honestly, if you can laugh during sex, you're already winning. It's like the time Josh just spread my booty cheeks and ripped me in half, right? Like we like joke about it now. Like stuff happens, guys. We're like bumping uglies, things are wet and slippery and slidery. Like, have fun with it. It doesn't have to be so serious all the time. Okay. And then we are gonna roll into some covet this. This week, covet this actually is two things because this topic requires both. So, first, a quality silicone-based lubricant. As we covered, lube is non-negotiable. Not it, I believe lube is a non-negotiable all the time, but it really is a non-negotiable with anal sex, okay? Silicone-based lasts longer, it provides better glide, and it makes the whole experience significantly more comfortable. Check my shops for options. I have a ton, okay? Second, if you're a beginner, a slim anal plug or a beginner trainer kit are essential, just so you can start to figure out your body what you like, what you don't like. Um, it's designed to help the body adjust gradually at its own pace without pressure. The Love Ends app controlled options are particularly great because the receiving partner gets to control everything from their phone, pace, intensity, um, stop, all of them. That's that CEO backdoor energy we talked about in tip six, okay? So both are in my shop. And if you want to see all of this in detail, ask questions, get real recommendations in real time, please come to my live shopping event and all the links are in my bio and check out my website for all the live shopping event details or any product questions. And like always, I am always here to answer your questions, um, give you tips and tricks. I wanted to make this a quickie because we were talking about something awkward but important. So, like always, with the love, Cassidy, today was fun, a little chaotic, and I hope at least one tip made you think, oh, I didn't know that. But here's what this episode really is about. And it's shame-free intimacy, it requires information, and information requires someone being willing to say the thing out loud without an apology. And if you listening to this podcast is helping, please share this with your friends, with your partner. Um, it's my mission to get people comfortable talking about this. I mean, I am the sex lady in Utah, right? So let's get everyone talking about it. So, so many people avoid conversations, entire experiences, because nobody has ever gave them a practical, honest, judgment-free version of how it actually, excuse me, works. That's what this show is for, that's what I'm for. Your curiosity is not shameful, your questions are not embarrassing, your desire to understand your own body and your partners is one of the most intimate things you can do to strengthen your relationship and bring you closer together. Ask the questions, have the conversations, try all the things. Laugh when it's funny, stop when it hurts, and always, always, always make sure to make your partner feel safe. That's the law. That's your cookie for today. 10 tips, zero shame. The genital mullet warning you didn't know you needed. So, yeah, if you're one of those people and you're like, oh my gosh, I didn't realize there was hair back there, there is. Take care of it, okay? If this has helped you, share it. Send it to the person who needs it anonymously, if necessary. I won't tell anybody. I'm Cassidy. This is the Law of Cassidy. I'll see you next week, Fein Ones.