Sex Education: Getting into Anal. For Beginners by Topher Taylor

Ah, the orgasmic and mysterious world of anal play. Anal is something that I hear about and advise on almost every single day of the week. Anal is something I think about every single day of the week. Anal is something I wish I was doing every single day of the week. It’s great. To many, anal is still mysterious and in some cases, it’s actually quite intimidating. I get it. We all grew up with it being seen as painful, the punchline of the joke, unhygienic, and in many cases as an abomination… *waves hello to Roman Catholic childhood*. But it’s not anything like that, really. I mean, sometimes it can be painful, which this guide will address, but people partake in and enjoy anal for a reason – it feels good. Let me help you. 

There are a few reasons that I am writing this guide;

  1. I don’t want people to be scared of anal.
  2. I don’t want people to do it wrong and put themselves off.
  3. There is nothing wrong with enjoying anal sex.
  4. There is no shame in bottoming.
  5. Indulging in anal play doesn’t mean you’re no longer ‘top’.
  6. People are always reaching out to me about this topic.

One of the things that I love the most about my job is that people reach out to me discreetly with their intimate curiosities and problems. It’s flattering. I also enjoy helping people to discover things about themselves and address possible issues surrounding their sexual interests. In fact, a majority of the messages I receive on dating apps and social media sites aren’t actually from people chatting me up – it’s people asking me for sex advice. My sex education work is often under the radar. I come from a discreet customer service background and have been speaking to people for over a decade by email, phone, and face-to-face. It’s always been private. Even beginning to write things down like this feels a little fresh. 

I was most recently inspired by a young guy (aged 19) who asked me about how he should go about having anal sex for the first time. He’d felt pressured by social media and even by some of my posts. This instantly made me feel guilty. His exact words were ‘you make me feel like I’m missing out’. I don’t want anyone to look at my posts or anyone’s posts and feel the need to be sexual. Everyone develops in their own way and in their own time. It’s worth remembering that I’m 30-years-old and have worked in the sex industry for 12 years. I have a bit more experience and have certainly been exposed to more than most. Everyone moves at their own speed, so try not to stress out too much. Your first time should be comfortable and most importantly, it should be on your terms.  

In the style of my 11 commandments, I’m going to list points that I find to be important and some advice that I wish that I’d had back in the day. In this post, I am speaking for myself and from my personal experiences. Ultimately, everyone is different but I’m confident that I can help. This blog is going to be the first of many ‘Getting into…’s covering different areas of sex, preparation and self-exploration.

Each instruction section below ends with a ‘tl:dr’ list, summarising each section, for those of you in a rush.

Keep in mind that I am speaking from my own experiences. This is the advice and steps I take for my body and I am sharing it with you. A lot of this will be universal… but not all of it. 

Anyway, let’s begin.

The shopping list.

If you are a beginner and want to have all avenues from my guide covered, here’s a quick and affordable shopping list to help you transition into anal with confidence.

  1. Lubricant. You should always have some lube handy. Personally, I am a fan of silicone-based lubricant but I’ve learned that after trial-and-error over the years. Everyone’s lube taste is different. Start with a thicker hybrid (mix of silicone and water) lubricant, like this, this or this. Always check that your lube is condom safe.
  2. Douche. Treat yourself to a simple bulb douche. These are easy-to-use, easy to store, and incredibly simple to use. No need to unscrew any shower attachments etc. Check out this, this or this.
  3. Condoms. Protect yourself, always. You can grab condoms from any high street pharmacy, corner shop or sex shop. If you are running low on cash – go to your local GUM clinic. Don’t know where yours is? Click here. No excuses. 
  4. Wet Wipes. Baby wipes or cheap face wipes, whatever your skin is most comfortable with. These help with any spillages, embarrassing liquids, removing condoms, and wiping up any excess liquid. Plus, they help to moisturise the delicate area around the anus. Try and get environmentally friendly ones.
  5. Towel. Get a towel for underneath yourself on the bed. You may need it, you may not. We will get to why. 
  6. Relaxation products. These are not essential but may help. We will get to them later in this guide.


This is the part where you’ll feel like I am patronising you. But hear me out. 

Do you want to have sex because you think that you SHOULD or because you actually WANT to? This may seem a bit of a strange place to start, but it’s very important to know this. In fact, it’s vital. We are surrounded by sex and sexuality at every turn. Movies, music, social media, magazines, the lot! Sex and promiscuity are everywhere. We live in a digital age where people can present a life that may not be entirely true or maybe excruciatingly honest. It’s easy to feel the pressure! I’m a cold aging bish and even I still feel it. You need to really have an open discussion with yourself about why you want to have sex. You don’t need to psychoanalyse yourself but it’s really worth thinking about whether you want someone’s body all over you and inside of you. 

Sex isn’t essential in life but it’s a fucking fabulous addition if you’re doing it properly with the right person. Or people. Listen to your body and try and learn to trust your gut. A good way of knowing if you really want to have sex with someone is masturbating whilst thinking about them and seeing if you feel committed to the idea just after you’ve cum. You’re never going to feel 100% up for sex the moment after orgasm, but it’s the perfect moment to gauge how you really feel about someone in particular.

“Sex isn’t essential in life but it’s a fucking fabulous addition if you’re doing it properly with the right person.”

Your first sexual experiences can shape your future interest in sex and your own sexual trajectory, whether you realise it or not. A study by Matthew Shaffer, a doctoral psychology student in Tennessee at UT, and C. Veronica Smith, an assistant psychology professor at the University of Mississippi found that from 331 people, first-time sexual experiences were predictive of future physical and emotional satisfaction.

Do you hear that? So, try and choose a little wisely. This leads me to…


There’s nothing wrong with being submissive sexually. But when it comes to consent, you are always in charge. Even as a submissive bottom (if you are or wish to be) you should always communicate your boundaries and say no when you want to say no. There’s never a need to feel anything other than comfortable saying no. Never, ever forget that. You don’t owe anyone sex. You don’t even owe your ego sex. Anyone that questions you saying NO to any type of sex has got to go. I don’t care how hot they are, how long you’ve waited, or how apologetic they may be in the aftermath. Goodbye. Next

There are a lot of predators out there who are actively on the lookout for naive people who aren’t experienced in protecting themselves against dickheads. Often, they know you’re too new-to-this to be recognising the warning signs. These people have a tendency to know the right things to say and the correct buttons to push to get your legs behind your head. These people may even be so used to behaving this way that they don’t even realise that they’re doing it. If something feels ‘off’ or you feel at all pressured, let it go, let THEM go, and wait for the next. Yes, this is frustrating and I’m sure you’re feeling impatient but this is a little thing I like to call ‘self-care and this should always come first. Self-care comes before you cum.

“If something feels ‘off’ or you feel at all pressured, let it go, let THEM go, and wait for the next”

If you feel intimidated by someone’s language, body language or persistence, my advice would be to avoid them. As a young person, new onto the scene, I had experiences with predatory men who would try and manipulate me into having sex or being intimate with them. I thought this was a natural part of ‘courting’, I thought they were being ‘lads’. I  didn’t realise that I was in a position to tell them to get lost (or in my case “fuck off”). If you’ve grown up without any sexual interest, as you’re the only ‘gay in the village’, it’s easy to not want to reject people for bad behaviour as you’re FINALLY getting ‘your kind’ of sexual/romantic attention. If someone places a hand on you and you don’t want it there – let them know, clearly and concisely. You don’t have to be rude – just clear. Keep a special eye out for ‘straight’ men who tell you that you’re turning them. You aren’t. Please, please, learn from my mistakes and don’t go down the ‘straight boy’ route. It does not and will not lead you anywhere good. 

If you’re meeting someone from a dating app, make sure you have made your boundaries clear before the meeting. If this for your first time, don’t meet them for sex right away, go for a (non-alcoholic) drink, and get to know the person as a physical being rather than a few shared images on a digital platform. If they aren’t up for this, then find someone who is. Also, tell a friend or colleague where you’re going, who you’re meeting, and what the plan is. You don’t have to give them the nitty-gritty details but give them a heads-up. Arrange to send this nominated person a text message (or some sort of signal) before you meet, as you meet, and after your meet. If you want a ‘safe space’ to meet someone from an app, you are welcome to use a Clonezone store as your meet-up point. 


I’m not just talking about condoms. That goes without saying. You can read my opinions on condoms here. What I am talking about is your body, your anus, and its limits. You’ve possibly seen that guy on Twitter, or on a porn upload site having really mad anal and he took it like a pro, didn’t he? No complaints. And you know why he took it like a pro? He -IS- a pro, mate. Do things at your own speed.

If you’re reading this guide with genuine curiosity, then you probably aren’t a pro just yet. You may just slip right into complete comfort and surprise yourself with what you can handle – but don’t assume that you will. Your hole is sensitive, so treat it with respect. Your butthole is full of sensitive blood vessels, nerve endings, and muscles. Irritating yourself by not adequately lubricating, being too rough, or forcing things inside can cause some really uncomfortable and embarrassing issues. Do you know what an anal fissure is? I’m not trying to scare you here or put you off, remember that this guide is about learning to love anal. But I am encouraging you to treat your body with respect. Your batty needs love, too! And remember, if it feels like your body is saying STOP! Then you should perhaps listen to it. Nothing should ever be excessively painful.

“Begin by just stroking yourself gently after a hot bath or shower with a generous amount of lubricant until you feel your hole is becoming slightly more receptive.”

And how can you protect yourself? By getting to know your body first and getting to know your limits before diving into anal with a partner. Using your fingers is a great way to start. Treat yourself to a nice lubricant (you can find a good lube for around a tenner, I would recommend this, this, or this, as good lubes to use for fingering). You can treat yourself to a small butt plug (Like this one, for example) but I’d say begin with your fingers. Make sure your fingernails are trimmed and buffered or simply put a condom over them. Begin by just stroking yourself gently after a hot bath or shower with a generous amount of lubricant until you feel your hole is becoming slightly more receptive.

Start with one finger and don’t force it inside. Take it slow. But when it does come to insertion, add some extra lube to your finger(s) as well as your hole. Even if it feels like you don’t need extra, just do it. Run your fingers around the hole and you’ll feel its plushness with the ring shape within this, don’t force, just gently guide your finger within this ring. As you push inside, use your anal muscles to push ‘out’ (like you’re going to the toilet), as this will allow entry much easier and help to relax the area as well as your sphincter muscles. You’ll feel it accepting the finger as you push these out. When you’re inside, rest for a moment and then gradually feel around and see what feels nice. Sometimes the simple motion of pushing in and out is enough to feel delicious. Don’t go hunting for your prostate just yet. Just take it slow, take lots of deep breaths, and if it helps – watch yourself playing in the mirror or on your phone’s selfie camera. It’s quite exciting seeing this for the first time. You might feel a bit like you need to pee or like you suddenly need to make another type of bathroom visit… but just wait it out and gently feel around. Repeat this a few nights a week.

If you’re using the small plug, try sitting up with it inside. A good position is the ‘prayer’ position, so your bum is resting on your feet. Try and angle it so the base of the plug is being held inside by your feet. If you’re feeling confident, gently roll your hips around and feel the sensations it’s delivers. Don’t be paranoid if you aren’t feeling anything too intense, as not all insertions feel intense. Sometimes it feels like there’s nothing really happening. This doesn’t mean that you’re ‘loose’ – it means that you’re comfortable. You’re doing it right. 

When taking your fingers or a small toy out of your anus, take it slow and push those muscles out again (like you’re going to the toilet). As it comes out, you may feel a bit of a burning sensation but that’s nothing to worry about. Don’t be put off if the experience felt unpleasant, as this is a baby step. It may not be clean also, but don’t panic. We will get to douching next.

Congrats! You’ve had something in your butt. 

The tl;dr:

  1. Don’t compare yourself to porn.
  2. Begin with rubbing and then fingering yourself gently. Lots of lube. 
  3. Buffer your nails or place a condom over your finger(s).
  4. ‘Push’ your muscles out like going to the toilet, to accept incoming traffic. 
  5. Do this a few times a week to get used to something being inside.


There are many ways to get your body ready for anal sex but the most common preparation is douching. Personally – douching can be the bane of my life but it’s part of my sexual routine that not only cleans me out, but it gives me more confidence in my sexual performance as I’m not worried about accidents. If you aren’t aware of what douching is, it’s the practice of cleaning all of the ‘mess’ out of your butthole and lower bowels to avoid said mess appearing during anal. You do this by using either a bulb douche, shower attachment, or enema kit to stream water inside of your butthole, release, and repeat it until it runs clear. As a beginner, I advise going for a bulb douche.

You don’t have to douche. It’s a personal choice. Some think that going to the bathroom and then rubbing a finger around the inside is enough to clean it out. Others don’t care/enjoy the idea of things getting messy. It’s one of those things that should be a decision made for you, but also keeping your partner in mind. Sex is all about communication, anyway. Personally, I am a clean freak, hate bad smells, have no toilet humour at all (I hate even the discussion of poop), and will not play unless I am prepared. 

A bit of advice: DO NOT wait until the first time you’re about to have sex before douching for the first time. Do some practice runs, even if you don’t have anything lined up sex-wise. 

There are ways to make douching easier (and quicker) for yourself, and that comes down to your diet. Try to avoid: caffeinated drinks, drinks with artificial sweeteners, spicy foods, oily foods, and excessive dairy products on the day of, or evening before anal. Up your fiber intake for a day or so before to firm up your stool and stay hydrated. Try to avoid anal whilst hungover, too, as you’re dehydrated and therefore more likely to have ‘loose’ stools – which are much more unpredictable and harder to clear out. Even after a thorough douche. 

“You don’t have to douche. It’s a personal choice. Some think that rubbing a finger around inside is enough to clean it out.”

There are lots of fashionable pills out there which are advertised to make douching easier. These work by firming your stool using Psyllium Husk. If your body isn’t used to this, don’t jump right into using them. I had a friend who took them for a few days and ended up giving himself chronic-constipation for 3.5 months. You don’t even know if you need them yet. And don’t get into a routine of taking Imodium (or similar brands) to help. Your stomach is very sensitive and it really doesn’t take much to irritate the regularity of your bowel movements, especially if you’re combining anti-diarrhea meds with douching.

A simple guide to douching:

  • Fill the bulb with water (to the brim or you’ll push air inside)
  • Lubricate the nozzle and your hole
  • Slowly insert nozzle and relax for a few seconds
  • Squeeze bulb to release as much water inside as possible
  • Hold the water until your body wants to release
  • Release without pushing too hard and check the waters clarity
  • Repeat until the water is clear or your comfy with its clarity
  • Make sure you re-lubricate yourself during douching

It’s not uncommon for some water to stay inside and surprise you during sex, sometimes it’s clean… sometimes’s its not. I usually give myself a 15-30 minute window before doing anything to encourage any excess water to come out. If you want to speed this up, lay on your bed on your side and gently massage your tummy – this will often get it out much quicker.

Click here to read my detailed Douching Guide.

The tl;dr:

  1. Begin by using a simple bulb douche.
  2. Do some practise runs before your first time. 
  3. Pay attention to what you are eating. Up your fiber intake.
  4. Avoid anal the day after drinking alcohol heavily.
  5. Give yourself 15-30 mins for all excess water to come out after you’ve finished douching.
  6. Stay adequately lubricated throughout douching. Top it up. 


Rimming is an ideal way to relax your hole before sex, as well as waking up some of those sensitive nerve-endings which deliver pleasure during reciprocal anal. Plus, rimming feels really fucking good. Psychologically, I find there is something so sexy about seeing and feeling the face of someone you fancy buried between your butt cheeks. I don’t know about you, but when I fancy someone I just want to know that I’ve sat on their face at least once. And I usually do. *finger snap*

So if they’re into it, serve it on a platter and make them eat it. And I don’t mean a few meal flicks of the tongue. The best thing they can do to relax you is really diving in there. You want their tongue to be lapping, dipping, and stroking your hole’s entrance. You want your hole to be left feeling wet, spongy, and warm once they’ve finished. The best position to be rimmed for relaxation is laying on your front, with a pillow under your hips and crotch to lift your butt up in the air. Or laying on your back, with the pillow (or two) under your lower back and bum to raise you into the air. Doggy also feels great, but I’d stick to the two positions above at first.

Not only is rimming a great way to relax your hole, it feels amazing and is so arousing. Your anus has a high concentration of nerve endings, therefore it is considered an erogenous zone. This is why it feels so nice. SCIENCE.

I would advise avoiding flavoured lubricants as (personally) I hate them and find they get really sticky. You don’t want your first time experimenting with anal to be sticky and smelling of artificial fruits. This is completely up to you, by the way. 

Please note that spit does not work as a replacement for lube. Possibly in the future, but not for beginners. OK?

The tl;dr:

  1. Rimming is a perfect way to relax your hole.
  2. It feels fucking great.
  3. Lay on your front with a pillow underneath you, or on your back with pillows underneath your bum. 
  4. Don’t use the spit as a substitue for lube just yet. Baby steps. 


It’s worth taking your partner’s cock size, or the size of toy you’re wanting to use into consideration. If it’s is particularly long or thick, you’ll need to prepare your hole a little bit more than usual. You can do this by using your fingers or a butt plug before anal (as discussed above), possibly using a relaxing product, and douching with warm water. Having a long warm bath or shower before sex will also help relax those tense muscles. If you have time and are particularly anxious about their size, spend some time with a small butt plug inside before sex. It’ll help relax those muscles which aren’t used to incoming traffic. 

Make sure you have a talk with your partner about how they penetrate you. If they are thick, they must take it slow on the first insertion, and if they are particularly long then it’s worth discussing NOT going ‘balls deep’ at first. Lots of men want to slide all the way in on the first insertion, as that’s when they’ll feel most sensitive. You’re really going to benefit from requesting that they DON’T do that. You can prevent this by getting them to control their thrusts and also with your own positioning. We’ll get to that.

“But when it comes to anal pleasure, and eventually prostate orgasm, 4 inches is really all that you need.”

And for the record: It’s not all about a big dick. Yes, they are fun to play with, and most of the porn we see online features people who are particularly well-endowed. But when it comes to anal pleasure, and eventually prostate orgasm, 4 inches is really all you need. If he’s large, that’s great but try and ignore the misconception that size is everything. Size is a preferential thing, but as a beginner, I wouldn’t worry about having this on your radar just yet.

Also, making a negative comment to someone about their penis size is cruel and damaging. Don’t do that, it’s not sassy, it’s cruel. And a dickhead move. Sexual satisfaction comes in all shapes and sizes.

The tl;dr:

  1. Prepare for the size you’re working with. If they are particularly large, you may want to relax your hole before with fingers and/or a small toy.
  2. As a beginner, don’t focus on hunting for big cocks. Size really isn’t everything. Trust me. 
  3. Communicate with your partner about how they penetrate you, focusing on the position, speed and rhythm.
  4. You only need around 4 inches to find your P-Spot (Prostate). 


At first, anal can be unpleasant. Let’s be honest. A large majority of people I know thought that after trying anal for the first time that it wasn’t for them and they’d never do it again. One of my friends vomited as they got themselves so anxious about it. They’d absolutely never enjoy it. Bollocks. The first time is always strange and sometimes painful, so give your asshole a break. The discomfort can be a real shock to your system and sometimes it can feel like every cell in your body is telling you to “GET THAT THING OUT!” – This, alongside the sensation of needing to go to the toilet can make the first few times unpleasant. But trust me, you’ll most probably learn to love it. Don’t let this scare you too much and try not to let it put you off. Remember that you’re putting something with length, girth, and which is solid into a part of your body that has been used to ‘one-way traffic up until now. It’s bound to be a shock to the system, and it’s going to be hard to relax your muscles when you’re trying something new. I found that suddenly everything felt nice after a few times because I’d learned to get used to the sensations. It was like someone had flicked a switch.

“Remember that you’re putting something with length, girth, and which is solid into a part of your body which has been used to ‘one-way-traffic’ up until now. It’s bound to be a shock to the system.”

And as we discussed above, get some practice in penetrating yourself first. That’s going to be the best way to understand HOW it’s going to feel and how to minimise discomfort.  A great way to get yourself ready for anal is to wear a butt plug before having sex, as this helps to relax your hole. There are other readily available products from sex shops and pharmacies that you can use to reduce pain and discomfort, and these typically come in the form of numbing or ‘relaxing’ sprays, creams, or lubricants with different relaxation agents within them. Don’t use too much and do a test run a couple of days before the fact. Treat it like dying your hair and give your butthole a ‘patch test’. Your intimate areas can be extremely sensitive, so never assume. Sometimes these numbing agents have a menthol-like sensation that burns a tiny bit as you apply it – this will quickly turn into a numbness so don’t panic. It’s all good. They also sometimes smell really weird.

These products are designed to RELAX you, so you should not use them to NUMB you. You want to feel if something is sensitive or painful. 

These products will help to relax those sensitive parts at the entry of your anus which typically are the bits that ‘sting’ as you are being penetrated. This doesn’t happen all of the time, so don’t worry if you aren’t feeling that. Even the most experienced anal players have days where it stings and days where they’re completely relaxed.

It’s important to remember sometimes that what you’re actually feeling is discomfort and isn’t always necessarily pain. Give your body time to adjust to and relax during sex so you can figure out if what you’re feeling is actually pain OR discomfort caused by you being a little tight, under lubricated or if you haven’t relaxed your muscles yet. 

Also: stay lubricated. Top it up a few times during play.

The tl;dr:

  1. Your body will feel shocked as you fuck the first few times. 
  2. Pay attention to what’s painful and what feels uncomfortable, as there is a difference. 
  3. If anything feels excessively painful, stop it immediately. Try again next time. 
  4. Consider relaxation products to take the edge off. Not to numb you.


Fucking in the wrong position for the first time can deliver a negative first-time experience which may put you off being fucked in the butt forever. I might be over-exaggerating a little here, but you get my point. A position can change the way you enjoy sex completely. In the beginning, unfortunately, I recommend being a bit ‘boring’ and playing it safe with your positions. Sorry love, but you aren’t a porn star just yet and this is about introducing your body to a new type of pleasure.

Begin by laying a towel underneath you. Remember, you aren’t completely used to douching or anal just yet – so excess water may come out alongside the possibility of other things. Don’t stress about it but do protect your bedsheets.

“…don’t completely arch your lower back until you’re ready. The more your arch your back, the deeper he will be able to get – so don’t rush into that. “

For your first time being fucked (or made love to, however you want to refer to it) I recommend laying on your side and getting him to lay behind you. Use pillows to prop your head and neck up, and don’t completely arch your lower back until you’re ready. The more your arch your back, the deeper he will be able to get – so don’t rush into that. Make sure your arm is free so you can stimulate yourself with your free hand as it goes.  In this position, your butt cheeks work as a buffer between your home and them getting ‘balls deep’, so in the beginning, keep your legs together and don’t raise it. This position is freeing as you’re front is open but you also have the intimacy of having someone’s body scooped in behind you. Having someone’s face right behind your neck then hearing them breathe and grunt as they fuck can be rather… well… hot.

Don’t start with doggy style or getting on top (riding). You’ll get there eventually but these two positions allow the dick to slide in-and-out BALLS DEEP without restriction, and I want you to take it slow so you can get used to this. Plus, riding is an art form in itself. I’ll teach you one day. Practice makes perfect.

The tl;dr:

  1. Lay a towel underneath your crotch and behind area.
  2. Lay on your side and have them fuck you from behind the first time. Use pillows to support your body.
  3. Don’t arch your back as a beginner. Yes, I know it looks better but it also allows him to get balls deep. You may not be ready for that. 
  4. Do not begin with doggy or riding. 


One of the first things that all of us think about (when we are new to sex) is “What do I do?” or “How can I be good at it?“. These are weighted questions as everyone’s tastes are different AND we all enjoy things for different reasons. I refer back to my earlier point of taking things at your own pace and not forcing yourself to do things that you haven’t got the skills to do just yet. You will get there. Slow down. Personally, I found that the idea of just laying there and being used as a replacement for someone’s wanking hand never appealed to me. I was always quite a bossy and aggressive sexual partner, but this came to me naturally and people seem to like it. I wanted passion and I wanted to make sure that both of us were satisfied with each other. You’ll find your sex personality as you begin to have sex. Get to know this side of yourself and don’t apologise for it. One of the most exciting and liberating experiences I’ve ever had as a human was getting to know myself sexually. 

As their penis or toy enters you, push your muscles out again like you’re going to the toilet. This will make the entry much smoother, alongside an adequate amount of lube. It’s not always necessary to focus enough to do this in the beginning, but give it a try. 

Top up the lube as you go. Lubricate, lubricate, lubricate. Not only to keep things sliding nicely, but it also reduces the risk of the condom breaking.

“You’ll find your sex personality as you begin to have sex. Get to know this side of yourself and don’t apologise for it.”

A simple way to ‘spice things up’ rather than just laying there and adjusting to these new sensations is using your hands to play with their body, talking dirty to them (but try and avoid putting on a voice or fake personality, just yet), pleasuring yourself (I’ll get to his in my next point down) or clenching-and-releasing your anal muscles as they slide in-and-out. Try and not rush into the clenching one on your first go but definitely add it to the list of things to impress your ‘top’ with in the future.

If you’re genuinely really into the idea of making sure that you please the guy who is fucking you, then ASK him what he enjoys and use this information if you’re happy to. Sex really is, at the end of the day, all about communication.

The tl;dr:

  1. Push your muscles out, like you’re going to the toilet, to help with entry.
  2. Make sure you’re adequately lubricated at all times.
  3. Touch each other and talk dirty if you want. Get into the moment and enjoy it. 
  4. Communicate with your partner. Tell them what you like and ask them what they like. 


When you’re being fucked, the sensitive points on your body have a tendency to feel a lot more sensitive. I’m talking about your penis, your perineum (the area between your balls-and-butthole), your nipples, and your anus itself. Sometimes it’s physical and sometimes psychological – but either way… enjoy them! I refer to mine as ‘the pink bits’ and I almost always play with them myself or get my partner to do it. I advise getting to know these a bit better when you’re being fucked, as it will give you a sneak-peak into why people love anal sex so much and the way it can affect the way your body feels. Not everyone’s nipples are sensitive, but mine are. Especially my left one hint hint. If this is sucked or played with during anal it sends my upper body tingling and it leads me to prostate orgasm much easier. You will soon learn about your own ‘hot spots’.

I find that I can be extremely psychological with sex. I’m digressing here but I am saying that by stimulating the ‘pink bits’, I allow my body to experience heightened pleasure which comes from the fact I am enjoying the sensation of anal sex. So, give it a go. Play around with these parts whilst being penetrated and see how they feel. It might not be for you… but it might drive you wild. There’s only one way to find out.

“I’m talking about your penis, your perineum, your nipples and your anus itself”

If you’re in the early stages of anal play, a great way to ‘distract’ yourself is to masturbate as you’re being fucked. Don’t think that you’re going to have to distract yourself forever, as you won’t. But for the first few times, this really does help. Also, when that dick (or toy, finger, etc.) is tapping your prostate on the inside, at the same time as you stimulating your penis on the outside = it. feels. good. Really good. We will get to prostate play in another blog soon. Trust me, your prostate is your friend.

Also, enjoy the fact that this partner you have chosen is inside of you and is getting pleasure from your body. Sex is incredibly intimate and there’s something irresistibly sexy about knowing you’re delivering sensations to someone and experiencing this intimate ‘transaction’ together. Sex really is wonderful. 

The tl;dr:

  1. Take advantage of your bodies sensitive points as you are being fucked (nipples, perineum etc.)
  2. Masturbate as they are inside of you, not only does this take the edge off any discomfort – it feels enhanced.
  3. Get into your head and enjoy the psychological side of it. This person you fancy is FUCKING YOU. ENJOY IT.



  1. the ability to sustain prolonged physical or mental effort.”

Contrary to popular belief and many porn movies: Sex doesn’t have to last for a long time to be amazing. Some of my best sexual experiences have lasted for just 5-minutes. There is a lot of pressure to be in bed for ages and being thrown around the room, all whilst looking perfect during the whole process. That’s just now how it always works out, guys. Sex can be really quite ugly, you pull weird faces, it can create weird smells, your body can make weird sounds and some people ejaculate very quickly alongside losing their erections.

“Try not to hold yourself to a standard that you don’t have any experience with yet.”

Anal can become painful if it goes on for too long, especially as a beginner. It’s always worth making sure that you’re adequately lubricated and that the position is working for you. If your top is taking longer than you were expecting, then communicate with him that you’re ready to stop now or perhaps would like to change positions. You can always finish him off with your mouth, hands, or other body parts if you want to. Sometimes our bodies are just feeling less tense than other days.

Try not to hold yourself to a standard that you don’t have any experience with yet as that’s ridiculous. Plus, who’s to say your top won’t ejaculate within minutes? And who’s to say that 2 minutes won’t be enough to satisfy you? You live and you learn. 

The tl;dr:

  1. Sex doesn’t have to last for ages. You can have amazing sex in a very short amount of time.
  2. If you are wanting it to end as it’s going on for a bit too long, communicate this clearly with your partner. Don’t be shy and risk hurting yourself. 
  3. Accept that sex can be quick, your body can make weird noises and smells, and some people will experience erectile dysfunction. 
  4. Don’t hold yourself to any standards. You are a beginner.


You’ve done it! (Or maybe you didn’t. Listen, there’s no rush either way).

It’s natural to feel an array of emotions after your first time, whether that be excitement, nerves, sadness, fear or just feeling completely unsure about how you feel. The first time I did it, I remember feeling unsure. I wasn’t sure if I was ecstatically happy that I’d finally done it, or I regretted letting go of my ‘virginity’.

You might find that post-sex that you feel a little sore down there. You also may have bled a tiny bit or find that lots of air has been pushed inside. Don’t be embarrassed about the air situation, this is simply what happens when the cock slides in and out – air comes in and out with it. It happens with vulvas, too. All of this is totally normal and is nothing to be concerned about. It’s also natural to feel the need to go to the toilet quite urgently afterward as well, especially considering the mix of douching alongside the internal stimulation of anal play.

If you’ve had unprotected anal (which I advise against) and his precum and/or cum has unloaded inside, you might find that your hole picks up a fishy smell a few hours after sex. I wouldn’t worry about this, as it’s simply the residues of ejaculant. It can typically be avoided by (gently) douching the cum out of yourself afterward. 

The only things you should worry about post-anal are:

  • Pain that lasts more than a couple of days
  • Discharge
  • Sores
  • Excessive bleeding
  • Excessive diarrhoea 
  • Unusual lumps and bumps

If you have any concerns about how you’re feeling, or finding that stuff isn’t really quite ‘right’ down there – speak to a professional. You can either go and see your GP or visit your local Sexual Health ‘Walk In’ clinic. Click here to find your local GUM (Sexual Health) Clinic.


You might find that after having sex the first time, you’ll want to be more sexually active. THE SEAL IS BROKEN. With this comes responsibility, and not just for yourself! Responsibility for your sexual partner(s). That means having condoms at home, getting tested regularly, and making sure you have the correct type of lubricant to hand.

Aim to test every 3 months at least. If you can’t get to a clinic, then order a kit online. There are many resources for free kits and they’re a quick google away. Personally, I use SHL (Sexual Health London) and BioSure.

There are a few things to keep in mind with ‘doms. As in condoms.

  • Make sure you’re not using an oil based lube (or oil itself of any kind) with latex condoms. They will gradually dissolve/weaken.
  • If you’re using any kind of medicinal anal cream for whatever reason, check that this is condom safe also. Lots of creams contrain oil-based ingredients which, again, can easily disintigrate latex.
  • Make sure you’re adequately lubed up before anal, as a dry hole and excess friction can easily burst condoms. 
  • If you’ve used an oil based lube for any other type of anal play before having protected sex, remember that any residue left inside can still break down the latex of a condom. 
  • If you or your partner are particularly large or small, you’ll need to buy a suitable condom for your fit. There are condoms out there to cater to everyone; smaller, larger and extra-large.
  • If you or your partner are allergic to latex, use a latex-free condom.

So, you’ve reached the end of my beginner’s guide to anal play.

All of the above may seem a bit preachy and possibly even a little overwhelming, but these steps will simply insert into your sexual routine without you even realising it. To me, they’re basics! It’s just about learning them for your own safety and pleasure.

Sex is one of the most fun and fascinating things on this planet, so use the above to help you develop and maintain a healthy relationship with your sex life. You should be enjoying it! 

If you want more clarification on any of the above, or simply want some advice, use the ‘Ask Topher’ page to reach out. I’m happy to help and I’m certainly never going to judge you.