NSFW: This article contains nude pics. Everyone here is 18+. I have permission to upload these photos. Happy to remove pics/stories – contact me.
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Cover image credit: Felix Uresti.
Update Feb 2021: Here’s a YouTube video I did covering this topic in more detail:
One question I get quite a lot is: “Andy you devilishly-handsome motherfucker, I’ve never done anal – how do I go about it?”
Ahh, so you want to slide inside her chocolate starfish, take the dirt road home, give her a rear injection, put your bike in the trunk, go colon-bowlin’? Alright, I’ve got you covered.
Anal is fun as hell for many reasons – it’s something kinky, you see it in porn all the time, it’s a different hole to stick your dick in (guys love sticking our dicks in random things, amirite?). All great reasons to stab her in the brown eye.
But I like doing it most is for the feeling of ownership – showing a girl you own all her holes. Girls fantasise about it and absolutely fucking love it – some have told me they feel like anal is the ultimate form of domination. They also love the feeling of “fullness” – especially if you also stick something in her pussy at the same time (eg your fingers, or a dildo).
There are quite a few girls I’ve done anal with who tell me they like it more than normal sex – it feels kinkier for them, the physical sensations are different, and they get off on the “degredation” aspect of having me fuck their ass. The one caveat is – I always put in the effort to make sure it’s enjoyable for her and never painful.
One question some guys have is: Will it be messy? Well, there’ll be plenty of mess with lube (because you need to use as much lube as possible) – you can just lay down a towel. But in terms of “mess”… as in, “Am I going to have my bed covered in brown?” – no. As long as she doesn’t need to take a dump, there won’t be any mess. If you follow this guide we’ll be using a condom anyway, and you can even do it in the shower like I did the first few times I tried it.
If you do decide to try anal in the shower, just be careful that the water doesn’t wash away the lube (water-based lube just disolves in water) – turn the shower head away from your bodies. More on that below.
Quick checklist of things you’ll need before we start:
- Anal Lube (or water-based lube from the supermarket)
- (Optional, but highly recommended) Buttplug training kit
- (Totally optional) Anal Douche
Most of this guide assumes she hasn’t done anal before, in which case,she might have a few concerns. She might be worried about:
- Will it hurt?
(Not if you use lube and go slow, and stop if it’s uncomfortable. I’ve had anal sex with a bunch of girls who’d never done it before – none of them said it hurt, because I went really slow).
- Will there be a mess?
(No. Only lube.)
- Will it feel good for me?
(Yes – most girls I do it with say it feels as good or better than dick-in-vagina.)
- Will it feel good for you?
(Yes – if you use plenty of lube, it pretty much just feels like regular sex.)
- If it’s uncomfortable, will you stop?
(Yes – of course you fucking will. You want her to have fun; anal’s not much fun if she’s not into it.)
If she’s nervous, just reassure her. Hell, share this guide with her – it’ll make her feel a lot better knowing you have a plan that involves her pleasure. Make it especially clear that at no point will it hurt, as long as you both go really slow and use a tonne of lube. Anal is supposed to feel good for her – if you take your time, she’ll enjoy it even more than you.
On that note, her ass isn’t something you can just dive right into straight away; if you just roughly shove your cock in, you’ll likely hurt her and make her never want to do it again. I’ve lost count of the number of girls who’ve told me they’ve only had anal sex once. I ask why only once, and they always say, “Because it hurt”.
Every single time I ask her to tell me about it, she says it’s because the previous guy literally just shoved his cock in her ass with no warming up, no foreplay, very little (or no) lube, no getting her used to fingers & toys first. The guys didn’t give a shit about whether or not she felt good. So these selfish idiots are out there just jamming their unlubed dicks into poor defenseless asses. They’re ruining anal sex for all the rest of us (and for the poor girls themselves).
So make it clear to her that this is not supposed to hurt at any point. If you follow this guide and above all else go slow, then it’ll feel really fucking good for her – which is what you want, right? It’s hot as hell having your dick in a girl’s ass while she’s moaning and telling you how mind-blowingly good it feels. (Much hotter than her wincing in pain and hoping it’ll be over soon…)
Your goal is to do it in a way that she absolutely enjoys – you want her to get off on this. Then she’ll want to do it again, and often. The girls I have anal sex beg me to fuck them in the ass sometimes, especially if we haven’t done anal in a while.
When you make it your goal for her to enjoy anal, you also have to accept it might take a couple of tries before she’s ready to accept your cock. The first time you explore, you may only be able to get a finger or two in – anything more than that may be too much for her. That’s fine – you can just finger her ass for a while and explore that, and then try for actual anal sex the next time.
Your mission isn’t necessarily to have anal sex the very first time; you need to understand if it’s her first time, she might not be ready for the size of your dick. You’ll have plenty of time to try again another day, so just take your time, be patient, and make her having fun your goal, not anal sex itself.
Shower or Anal Douche
Before you guys get started, offer her a shower if she wants to make sure she’s extra clean and nice for you. Most girls will say no, but some will really appreciate it.
If she’s especially worried about “being unclean” (some girls worry about this), you can get her to use an anal douche. It’s just a device you use to clean yourself out a bit before anal play.
You absolutely do not need to use one – and you’ll find 90% of girls are fine with just having a shower. But some girls will take you up on the anal douche offer, and will really appreciate you offering it.
Again, I’ll make it clear – a douche isn’t mandatory. Most girls won’t want to bother, but some will. There’s no mess either way (again – as long as she doesn’t feel like she’s just about to take a dump). Ask your girl what she’s comfortable with – it’s entirely up to her.
If she does want to use it, show her the following part of the guide (or go through it with her). Anal douches are all pretty similar – they have a container you fill with water, and a “rod” that fits on the end.
Read these steps out loud to her:
- Fill the container up with lukewarm water (NOT hot, and NOT too cold).
- Put the rod on.
- Insert the rod into your anus gently.
- Gently squeeze the container to fill yourself up with some water.
- Slide the rod out.
- “Let go” – as if you’re having a bowel movement (it’ll feel the same).
- You can do it just once, or repeat it a couple of times – whatever you’re most comfortable with.
Some girls like to do this in the shower (obviously alone – not with you there), so they can wash everything away. Other girls like to fill it in the bathroom sink, then do it over the toilet – so it’s like they’re just going to the toilet like normal.
Again, an anal douche isn’t mandatory. But you’ll find the girls who do want to use it are very grateful you’ve given them the chance to feel clean.
Whether she has a shower or uses the douche, she’ll enjoy anal much more and be able to relax more if she feels nice and clean and pretty.
So she’s either used the anal douche to clean her Hershey highway, or she’s had a shower. Now’s the time to decide – do you want to have your anal fun in the shower, or on a bed? I recommend a bed – it’ll be 100 times easier. (If you’re worried about lube getting on your bed, you can lay a towel down and have her lie on top of it.) I like to have a box of tissues next to the bed – at some points, you’ll want to wipe some of the lube off your hand so it’s not getting everywhere.
I also like to dim the lights so it’s pretty dark. Most girls feel more comfortable with “mood lighting”, vs bright white lights (which feel a bit clinical, like a hospital).
If you’d prefer to do all this in the shower, then go for it – I’ll go through how to do that as well. I like to have the lights down low (or off) in the shower too – it makes her feel more comfortable.
The next step is to get liberal with lots of lube.
Lube is absolutely mandatory with anal sex – if you don’t have any lube, don’t continue until you’ve gotten some. No, you can’t use lotion, no you can’t use olive oil, no you can’t use butter, no you can’t use massage oil, and you definitely can’t use your spit. None of those will last long enough (they all get absorbed by her skin and she’ll go dry, which will be painful). Buy some proper lube.
This is basically the same lube I use. It’s specifically called anal lube – make sure it’s water-based. Anal lube is thicker than regular lube. When you apply it, it goes on thicker (less runny), so it won’t drip everywhere and make a big mess. It’s much easier to apply to your fingers/toys/your cock, compared to regular lube.
You can also buy lube from your supermarket/pharmacy. If they have anal lube buy that; otherwise regular water-based lube will do (but it’ll be more runny than anal lube, so it’ll make more of a mess).
If you’re doing this on your bed (laid down your towel already?) get her to lie down. I’ve always found it much easier with her on her back (butt facing down) the first time – it’ll allow her to relax easier. However, you may want to try with her lying on her stomach (butt facing up) – you might find that easier because you’ll be able to see what you’re doing. Do whichever works better for you both.
Whichever position she lays in, now’s the time to put on a tonne of lube. Just squirt some around her anus – put on much more than you think you’ll need. Go crazy with it. It’ll drip down her legs a bit – this is why I said to get her to lie on a towel.
If you’re doing this in the shower, get her to turn around (so her ass is facing you. Put on a tonne of lube in the same way. Just make sure the showerhead isn’t pointing towards her body. The water will wash away the lube, making her dry (which will make anal play painful). If you’re doing anal stuff in the shower, water is your enemy.
Alright, so you’ve got plenty of lube all over her back door. We’re going to start nice and slow – just 1 finger.
Put a tonne more lube all over your index finger – make it nice and slippery. If you’re on the bed and she’s on her back (butt facing down), reach underneath her and gently rub around the entrance to her anus with your lubed finger – just tease her gently, nice and slowly, making slow circles around the outside of it.
If you’re doing this in the shower, just do the same thing – tease the entrance to her ass. Again, make sure there’s no water anywhere near her ass, or it’ll wash the lube away.
Don’t push your finger into her ass just yet; the goal is to tease her like crazy and make her horny and desperate for it. Remember I said the goal was for her to enjoy it? The biggest part of enjoyment for girls is the foreplay and teasing – so we’re going to delay this as long as possible until she’s begging for it.
You can use your free hand to rub her clit or play with her nipples, at the same time as you’re making gentle circles around the outside of her anus. Just make sure you don’t switch hands – the hand that you’re using to play with her ass, make that your “anal hand”. For the rest of the session, only use that hand to play with her ass; if you go from ass to pussy, there’s a tiny chance she could get an infection. I always like to be safe.
Keep teasing her ass with one hand, and playing with her clit with the other. You can move up to her ear and whisper, “Do you want this finger in your ass? Ask nicely.” Tell her you want her to beg. Whisper, “I need to know you really really want this – tell me how badly you need it.”
You might want to put some more lube on your finger (you can never have too much lube, especially the first time). When she’s horny enough and begging, very gently slide your finger inside her ass – but only a little. Only go up to the first finger joint – our aim is to tease her and drive her crazy, remember. Start very slowly moving your finger in circles inside her ass, and ask her how it feels.
At this point, most girls are just getting used to the sensation and enjoying it – if she’s never done any anal play before, this will feel very new and amazing to her. Most girls love this bit and really want to explore it, so take your time – there’s no rush. Slide your finger in a little more and ask her how it feels – ask her if she wants you to slide your finger all the way in. (Of course, she’s only allowed to have your whole finger if she begs for it 😉 )
This is the part where you can both really experiment. Try anything and everything you can think of – try sliding your finger in and out really slowly, teasing her. Try going a little faster (make sure it’s still slippery – apply more lube if you need).
Try having your finger in her ass, and then use your other hand to gently finger her pussy at the same time. I like to push both in at the same time (one finger going into her ass at the same time as another finger going into her pussy). Then try alternating – slide a finger into her ass, then gently start pulling it out as you slide another finger into her pussy. Then as you slide the finger out of her pussy, slide the first finger back into her ass, alternating these strokes. (Remember not to use the same finger in her pussy and ass).
Next, you can try 2 fingers, or your thumb. Just remember to apply a hell of a lot more lube to the new finger/thumb, and go slow. Some girls can comfortable take 1 finger but struggle with 2 – remember your goal is for her to have fun and not feel any pain at any point.
After this point, I like to move on to my buttplug training kit. They’re just a set of buttplugs that range from small (about the width of your finger) to very large (probably wider than your dick).
Grab this one – it’s similar to the kit I own. It’s pretty damn cheap and makes anal sex a lot easier for newbie girls. (You could also try an “inflatable buttplug” – they come with a handpump to make them expand once you’ve inserted it. I haven’t owned one myself, but feel free to experiment and let me know if you like it better than the training kit I use.)
You don’t have to use buttplugs; but they make things a billion times easier. If you absolutely don’t want to buy the kit, you can use fingers and work your way up to her being able to take 2, then 3 fingers in her ass. Use lots of lube, go slow, and be patient. Once she can take 2 or 3 fingers, then next stage will be your cock.
(Note: These buttplugs aren’t designed to stay in all day – they’re just a training kit which means you use it to open her up every time you want to have anal sex. You can buy buttplugs which are designed to be worn and stay in for as long as you want; more on those at the end of the article.)
If you managed to get two fingers (or your thumb) inside her ass, then you can jump straight to the medium buttplug. It’s slightly wider than the width of two fingers.
If you could only get 1 finger inside her, then use the smallest buttplug first and let her get used to it. Her ass is obviously tight, so we’ll need to work up to the medium buttplug – don’t be disappointed if she struggles to take it today. If she can’t, you can just try again next time.
Lube lube lube – absolutely drench that buttplug in lube so it’s super slippery.
If you’re on the bed, and she’s lying on her back, just slide the buttplug under her and gently push just the tip of it inside her. (You might need to tell her to lift her butt up a bit, or lift her legs in the air). If she’s on her stomach (butt facing up), you should be able to slide it in a bit easier. If you’re in the shower, it’s usually easiest for her to face away from you and bend over a tiny bit (with her arms against the wall) so you can slide the buttplug into her from behind. (Again, make sure you avoid water).
If you’re using the smallest buttplug, you should be able to very gently push it until it’s all the way in. When it’s in, just let her get used to the sensation – play with her clit with your “clean hand”, kiss her and make out with her for a while. After a few minutes you can slide it out and move on to the medium buttplug.
If you’re using the medium buttplug (remember to only use it if she could take 2 fingers or your thumb, or after you’ve used the small buttplug), then it might be a little harder to slide in. Go slow, and ask her every few seconds, “How does that feel? Tell me if it’s uncomfortable.”
She’ll usually feel a gentle “stretching” feeling. Mention it to her – tell her it’s normal that it’ll feel slightly “weird”, like she’s being stretched a bit. But make it clear it should never hurt, at all – tell her if it hurts, she needs to tell you immediately and you’ll stop pushing.
If she does ask you to stop (or she seems to be wincing in pain) just stop pushing and hold it still. Often if you wait 30 seconds or so, you can then start (gently!) pushing again. Other times you’ll need to pull the buttplug out, put more lube on it (put a lot more lube on) and try slowly inserting it again. With some girls, it may take a couple of tries, so be very patient.
If at any point she wants to stop, just stop – you can try again the next time you see her, and you’ll likely get a little further. Remember, your goal is for her to never be in pain; she’s supposed to enjoy this. If you make sure it never hurts, then she’ll be happy to keep trying with you until it works. But if you push it too far at any point and you hurt her, she’ll be much less likely to give it another go with you.
As long as she relaxes (tell her to close her eyes and relax), and as long as you go very slow, you should be able to slide it all the way in eventually. (It sometimes takes me 2-3 minutes for very tight/nervous girls).
I like to leave the medium one in for a while, so she can really get used to the size. At this point you can have some real fun (you’ve been so patient, I think you deserve it). Clean your hand with the tissues you had nearby (or if you’re in the shower, just wash your hand off). Put on a condom, and while the buttplug is still in her ass, slide your cock into her pussy very gently. Go really really slow.
If you’re on the bed, sex will be easy. If you’re in the shower, it’s easiest doggystyle – you might have to get her to bend a little further down. If you can’t get it to work (shower sex isn’t always easy), you can always hop out of the shower and continue on the bed with a towel laid down.
Once you do get your dick in her pussy while the buttplug is in her ass, it’ll blow both your minds. For her, it’ll be the most “full” she’s ever felt in her life. It’ll feel like fucking bliss – she might not even be able to talk. And for you, it’ll feel insanely tight – you’ll also be able to feel the buttplug pressing against your cock through the layer of her skin. Move really really slowly (don’t go too fast – let her get used to it) and both of you just enjoy the sensation.
I like to really take my time here and go a slow as I possibly can, both of us getting lost in how good it feels. Go so excruciatingly slow it barely feels like you’re moving in and out at all, until she’s a quivering mess who can’t help but beg for more of your cock.
You can finish here if you want to – as in, fuck her until you cum. Then you can just take out the buttplug, have a cuddle, and explore more anal stuff next time (you can have anal sex next time). Or you can stop fucking her now and continue going forward with the anal stuff.
If you’ve worked your way up to the medium buttplug, she’s usually ready to try your cock now. I don’t usually bother with the large buttplug – though you can if you want to. (Again, lots of lube, go slow). If you’re a larger gentleman when it comes to penile girth, then definitely do the large buttplug first.
Note I said try your cock now; there’s a chance your dick might be a bit big for her. If that’s the case, don’t force it – we don’t want this to hurt at any stage, remember. We’ll just try again the next time.
So, let’s dive in to her back door. Take out the buttplug, squirt some more lube onto her ass. Put on a condom, and absolutely cover your dick in lube – go nuts with it.
Getting your dick inside her fudge-hole works best if you have a full erection; it really won’t work if you’re not fully hard. If you’re not completely hard or you struggle with performance anxiety/ED, read my guide on fixing it.
If you’re in the shower – do this next part doggystyle.
If you’re on the bed and she’s on her stomach (so her butt is facing up in the air), it’ll be fairly easy to access her ass doggystyle.
If she’s on her back, you might have to hold her legs up in the air so the angle is better. Like this:
I prefer this last position the best, because she’ll be the most comfortable – it’ll be the easiest position for her to relax. But if you can’t get this position to work, get her to flip over so she’s doggystyle.
Ok, so she’s lubed up, your dick is wrapped up and lubed up, and you’re hard. Ask her if she’s ready (some girls will be nervous and quiet at this point – just make sure she’s still having fun) and remind her you’ll go slow.
Very gently place your cock at the entrance to her ass and push in slowly – very slowly. Your cock is likely thicker than the buttplug you just used, so you’ll have to go through all the same steps you just went through – being patient, going slow, asking her if it feels ok, taking a break and waiting 30 seconds if need be.
Some girls will take your cock pretty easily, and you’ll be surprised that it just seems to slide in. Other girls will take a few minutes of patience before it gets most of the way in. And some girls won’t be able to take it at all. In that case, you know the drill – try a couple of times (as long as it’s not hurting her), but if you can’t get it to work today, you can just try again next time.
Once you’re most of the way in, just pause for a second, and let her enjoy the feelings. Leave your cock inside her and play with her clit, or her tits, teasing her. Whisper in her ear, “How does it feel having my cock in your little ass?”
Start slowly sliding in and out of her ass, making sure she’s enjoying it (if you’ve put lots of lube on, she should be having the time of her life at this point). If she’s still a tiny bit uncomfortable, just go very slow (or don’t move at all – just remain still and play with the rest of her body). If she’s quite comfortable, you can fuck her a little harder – just build up to it gradually.
Some girls will be really fucking horny at this point and might even beg you to fuck them hard. Gradually work up to it – if she’s a trooper, she’ll be able to take you fucking her pretty hard. There’s nothing hotter than fucking a girl hard in the ass while she moans and screams in pleasure, begging you for more. God damn.
You can also slide a finger or two inside her pussy (using your “clean hand”), and gently finger her while you fuck her ass. If you aim your finger towards where her cock is, you’ll be able to gently press on the layer of skin between your finger and your cock. If you kind of “stroke” gently, it feels like you’re stroking your own cock through her pussy; like you’re giving yourself a one-finger-handjob. Tell her, “I’m softly giving myself a handjob” and watch her crack up.
Once she’s used to the size and she’s really starting to enjoy it, try a few different positions and play around. Doggystyle is the obvious one – girls love the way it feels to be fucked in the ass doggystyle; it’s very dominating. Missionary works too if you lift her ass up. You can try spooning. Her on top (tell her to lower herself very gently and go slow).
The main thing is: enjoy it and explore together. Banging her fartbox is a hell of a lot of fun.
If you want to switch to fucking her pussy, remember not to go straight from ass to pussy. Best to be safe and minimise the chance of giving her pussy an infection. Take off the condom, put another one on, and go for it. (Going from pussy to ass is fine though).
If She’s too Tight/It’s a Little Painful
If at any point she’s in pain, stop. Anal sex is something you have to work up to in many cases; it’s not a matter of just shoving your cock in her ass. Remember, you want her to enjoy this so she’ll want to be your anal whore in future, right? Then take your time.
If you can’t get your cock in without it hurting, or you can’t even get to the buttplug stage, then give her homework to practice herself. Tell her to go into the shower when she’s at home, and play with her fingers and a toy if she has one. Tell her to use lots of lube (buy her a bottle or get her to grab some from the local supermarket). Just tell her to make sure it’s water based lube.
She can go at her own pace, and will be able to explore anal on her own, getting used to how it feels, learning how to do it. This will make it a lot easier for you to bang her ass next time you try it with her.
Make it fun by telling her to send you a nude photo every day. Make it a fun game: “I need to check and make sure you’re doing your homework young lady, so make sure you take a photo and send it to me each day you do it.” (Even if she’s older than you, still call her “young lady” – most older women love being called that even more than younger chicks do.
Once she’s gotten a bit of practice at home by herself, she should be ready to try again with the buttplugs and your cock.
Cleaning Everything Afterwards
Afterwards, I always jump into the shower with her (if you were already playing in the shower, props for being so efficient) so we can both wash all the lube off and wind down after our buttfucking sesh. Bring the buttplugs + anal douche into the shower with you too, and wash them down with plenty of hot water and soap.
I go further with my cleaning – I also use 70% isopropyl alcohol and this exact toy cleaning spray.
70% Isopropyl Alcohol: Buy a big bulk container of it from ebay/Amazon, as it’ll be much cheaper. Then buy an empty spray bottle for a couple of bucks.
Toy Cleaning Spray: Use any toy cleaning spray that has good reviews. I use this one.
Just spray the alcohol and leave it for a couple minutes. Then spray the toy cleaner and leave it for a couple minutes. Then rinse them off.
Hop out of the shower, hangout for a bit and have a cuddle, and give her a highfive for doing a good job.
Awesome – you successfully navigated her chocolate passage! If you were patient and went slow, and made sure she had a good time, she’ll be begging you to go for round 2 (and 3 and 4 and 5…)
Storytime: My Most Recent Anal Adventure
A while ago I met a new girl from Tinder who’d never done any anal play – she hadn’t even had a finger in her ass. She was nervous but very curious to try – her main concern (as with most girls) was, “I’m scared this will hurt.”
She told me a horror story from one of her friends – a girl who’d tried anal at the insistence of her boyfriend. He’d only used a bit of his spit as lube, and hadn’t done any foreplay or warming up. No fingers, no toys, no buttplugs – just his big hard cock and her tiny impuissant sphincter. Needless to say, the friend found it incredibly painful, and warned my girl against trying it herself. I reassured her of course – “Your friend and her boyfriend are fucking idiots. Anal isn’t supposed to hurt”.
The second time we met, I told her I was going to teach her how to take my cock in her ass; again, making it clear to her I’d make sure it didn’t hurt. We made out for a bit on the couch, I picked her up and carried her into the bedroom, where I had the lights down very low so she’d feel more comfortable. I had a towel down on the bed and I got her to lie down on it, then I blindfolded her. I tied her to the bed, with her arms and legs outstretched, completely unable to move.
I spent quite a bit of time teasing her – playing with her nipples, gently teasing her clit, going down on her for a bit, and whispering dirty shit in her ear. We had sex for a minute or two, with me intentionally moving my dick in and out of her pussy very slowly (almost too slowly – she was going crazy). When she was at the point where she was horny as hell, I got the lube, the buttplugs and the tissues and put them next to the bed.
I started off doing exactly what I told you to do above – I got plenty of lube on my index finger and just making slow circles around the entrance to her ass, teasing her. She’s a pretty quiet girl; she tends not to say much during sex, so I asked her a couple of times how it felt… and didn’t get much of a response, other than a gentle nodding of her head. I slowly slid my finger inside and she moaned, her mouth wide open now, very clearly enjoying the new sensations.
When my finger was all the way in, I kept it inside her ass and used my free hand to guide my cock into her pussy too (she was lying on her back – missionary position). I went as gentle as possible, my cock deep in her ass, not moving it at all, letting her get used to it. At the same time I slowly fucked her pussy, really gently – barely moving at all. A girl’s first anal experience is always more exciting if you go as slow as humanly possible and draw it out for as long as possible – that’ll definitely make her want to come back for more.
I asked her plenty of times if she enjoyed it, and she kept nodding her head, gently moaning. After a few minutes I pulled my dick out of her pussy, pulled my finger out of her ass and wiped the lube off on some tissues. It was time for the smallest buttplug.
She’s a very tiny girl (she’s like 5ft2 and weighs 40kg/88lbs), so my goal was to go very slow and gentle – I wasn’t 100% sure she’d actually be able to take my cock today. I was prepared to have to try a few times, over a couple of different days. You should prepare for the same thing when you’re with a girl who’s never done it before – go in with the expectation you may have to try a few times over a few different sessions.
I lubed the small buttplug up with a ridiculous amount of lube (always go heavy on the lube) and slowly, very slowly, slid the tip into her ass. I barely put any pressure on it, letting it gently slide in. Again, I fucked her pussy with my cock a bit, this time moving the buttplug slowly in and out of her ass at the same time, driving her wild.
I gave her plenty of compliments, reassuring her – “You’re doing such a good job, your pussy feels so fucking good.” At this point she was moaning nonstop and lost in her own world – she later told me she completely forgot where she was, and couldn’t think about anything other than how good her ass and pussy felt. (The blindfold and being tied up definitely helped.)
After a few more minutes, I pulled my cock out, took out the buttplug and ask her if she wanted to try the medium-sized buttplug. She let out a quiet, “Ok”. I grabbed it, covered it in even more lube, and again gently pushed in just the tip.
The medium buttplug is quite a bit bigger than the small one, so I told her to just relax and take some deep breaths. I reassured her, “Just tell me if it’s uncomfortable at any point, and I’ll stop pushing and we’ll take a break.” She nodded.
I kept some gently pressure on it (the buttplugs have a nice big base that makes it easy to push on), and it very slowly slid in. It took about 1 minute of gentle pressure and her relaxing, the whole time me checking her expression to make sure she wasn’t wincing. She definitely wasn’t – she seemed to be enjoying it. (Some girls will put up with pain and not tell you – so you might have to remind them a couple of times, “Remember to tell me if it’s uncomfortable.”)
Once it was all the way in, she moaned loudly, and let out a soft, “Oh that feels amazing.” Her little body was arched up, resisting the ropes around her wrists and ankles, her mouth open – jesus christ she looked hot. My cock was throbbing so I put on another condom and slid inside her pussy all the way, the buttplug in her ass making her pussy feel super tight around my dick.
I leant down and kissed her passionately, then asked her what it felt like. “I feel like I’m so full… this feels amazing.” I gave her plenty more reassurance and told her she was doing such a good job, and we kept going like that for a while – her body tied up underneath me, unable to move as I filled her pussy and the buttplug filled her ass.
I pulled out and laid next to her for a bit, gently playing with her clit, her eyes still covered by the blindfold, ass still filled with the butt plug. I whispered in her ear, “Would you like to try my cock?” She took a few seconds to answer , “As long as you go really gentle though.”
I pulled the buttplug out and laid it down on some tissues (to avoid a lube mess on my carpet). I still had the condom on so I covered it in heaps of lube – even more than I’d used for the medium-sized buttplug. I tried to line my cock up with her ass but there was no way it was going to work with her tied up, so I undid the ropes, her stretching her limbs to get some blood flowing back into them after being tied up so long.
We tried again, but even with me lifting her legs up in the air, I wasn’t able to line my cock up with the entrance to her ass. (It just doesn’t work with some girls – my girl wasn’t able to relax enough to lift her butt up for me. She was clearly very nervous).
So I flipped her over doggystyle, told her to lie down on her stomach (with her stomach flat against the bed), and I spread her legs nice and wide. I put a bit more lube onto my cock and squirted some on her anus, and very gently pushed the tip of my cock against the entrance to her ass.
She moaned immediately but then tensed up – I hadn’t even started pressing in yet. I told her to relax and she did (you might have to remind your girl a few times to relax – especially if she’s nervous).
Going super slow, barely putting any pressure at all, I let her get used to the pressure, until I felt myself start to slide inside. It felt fucking amazing – it feels like a pussy, but tighter (and maybe slightly warmer, depending on the girl). I was halfway in and she was moaning like crazy. I asked her how it felt and she said it felt “So so so good”.
I slowly pushed in all the way, taking my time – it took me about a full minute or two to get all the way in. Once I was all the way in, I was barely moving – gently sliding out half way, then sliding back in, taking about 10 seconds per stroke. I always go this gentle the first time, because I really want to make sure she enjoys it and has a chance to really take in all the sensations and feel it. Your mindset here really should be, “I want her to have the best time possible” – the more she enjoys it, the more she’ll be begging you to do it again.
We tried other positions too – spooning was her favourite. Since she’s so tiny, it was very easy for me to (gently) fuck her ass while leaning over and sucking on her nipples. I let her grind her hips against my cock, allowing her to do most of the work – I like to let girls do a lot of the moving the first time, she they can figure out what feels good for them.
I gave her plenty more praise as we fucked like that, “You’re doing such a good job, taking my big cock in your tight little ass baby. Fuck it feels so god damn good.” (Girls love plenty of praise; if you want to “talk dirty” with girls, all you really have to do is give them lots of compliments).
After a few more minutes I grabbed my big vibrator, turned it on the lowest setting and held it against her clit while slowly sliding my cock in and out of her ass. She was going absolutely crazy – arching her body and grinding against my cock, while also leaning into the vibrator to get more of those sensations. The whole time I wasn’t moving too fast, just letting her get used to the feeling of anal sex.
After about 15 minutes we took a break and I slid out of her, taking the condom off my dick and giving her a hug. I stood up, took her by the hand, led her into the shower and spent a bit of time gently soaping her up and washing away all the lube. I like giving girls a nice pampering shower after anal sex – it makes them feel all nice and clean and pretty again. Then you can take them back into the bedroom and fuck their pussy some more if you like.
Took her back into the bedroom and we chilled for a bit, as I asked her if she enjoyed her first foray into anal play. She said she absolutely loved it – “I didn’t expect it to feel that amazing my first time. It felt so good. I didn’t know it was supposed to be that good.”
“Well, yeah. I told you your friend and her boyfriend are fucking idiots.”
We fooled around and fucked a bit more (I fucked her pussy this time). I went much harder in her pussy, fucking the shit out of her for a minute before pulling out and cumming all over her face. Nice.
Walked her back to the train station, and texted her later that night:
This is exactly how you want anal sex to be – for her to love it so much she really really really wants to do it again. So what did I do right?
- Started with just finger.
- Lots of lube (use triple the amount you think you’ll need), applying lots more at every stage.
- Went slow at absolutely every stage – barely moving my finger/buttplug/cock, moving very gently.
- Asking her plenty of times if she was enjoying it; making sure it was never painful for her.
- Never thrusting hard or fast, no matter how much I wanted to. (Yes, I was very tempted – it feels really good. But you need to control yourself and not go fast the first time). You can be rougher the second time; the first time should be about letting her get used to how it feels.
A few days later:
This time I told her I’d introduce her to my girlfriend, and that my girlfriend and I would be using her ass. I’ll write up the full story some time, but the short version of it is my girlfriend fucked her pussy with a strapon, while I filled this girl’s ass – and I was a lot rougher and harder this time. It’s fucking hot fucking a girl along with your girlfriend, the two of you using both her holes, smiling at each other as you use her.
She absolutely got off on it too – at some point my girlfriend told her, “You want to be our little toy, don’t you?” She was begging and pleading, “Please use my holes, I’ll do anything you both want, just please fill me up and fuck me however you want.”
I also have another story of some anal play with another girl who’d never done any anal before: Andy and His Girlfriend Bang a 6ft1 Giant.
Other Stuff to Try
The buttplug kit we used above isn’t designed to stay in for a long time – they’re pretty slippery and they slide out easily. You can buy fancy metal buttplugs that stay in for longer – they’re designed to stay in for as long as you want (even all day).
Metal buttplugs feel the best for girls because they’re cold to the touch – girls always tell me it feels amazing as it slides in due to the cold sensation.
I like to get girls to put them in when we go outside, so she’ll feel it inside her the whole time as we’re walking around, with other people none the wiser. Girls get so horny knowing nobody else can tell – especially if you “accidentally” push against it from time to time.
I’ve also had a few dates where I’ve gotten her to meet me with a buttplug already inserted, so by the time I get her home, she’s dripping wet. A lot of girls will be so horny they’ll text you all sorts of dirty shit as they’re on the way over. Every step she takes will make the buttplug move in her ass a little, getting her off.
If you have 3somes with girls, you can also buy a strapon, and get one girl to fuck the other girl’s ass while you fuck her pussy (double penetration).
I own two: this one, which is just a normal strapon. I also own a strapless one – one end goes inside one girl’s pussy, and the other end goes inside the other girl’s pussy. Girls prefer this one because then they both get to feel good (a regular strapon doesn’t stimulate the girl who’s wearing it).
Girls go absolutely wild having one girl in her ass, and you in her pussy at the same time (or the other way around).
(If 3somes are something you want to get into yourself, grab my How to Have a 3some (Even If You Don’t Feel Ready Yet) guide).
Any questions about anything here? Ask away and I’ll answer.
Great thorough article, appreciate the detail.
However, I’d appreciate if you could give some advice on approaching the topic of / introducing anal sex with a girl. As a newbie who has only had anal sex once with a girl before (she suggested it), but have never initiated it on my own, I don’t know how to go about doing that.
Should I ask her if she’s done it before / if she likes it / if she wants to try it? If so, at what point? Before, during, after (first time) sex?
Or should I just put my lubed up finger to her asshole (without saying anything) and massage it while I’m fucking her pussy and then escalate it from there like you describe in the article? (as long as she doesn’t stop me, obviously)
If she does stop me, should I ask her what’s wrong, or just pretend like nothing happened and try again later?
On the one hand, the thought of verbalizing the action of anal sex out loud in bed (“I want to fuck your ass / Do you want to try anal?”, etc.) seems “unsexy” to me (as opposed to “just doing it”), but then again, not saying anything also seems weird.
I’m a newbie here, so I have no frame of reference of what’s “normal”. I’d be really grateful to you if you could provide some sort of actionable framework as to how to do the above.
“Should I ask her if she’s done it before / if she likes it / if she wants to try it? If so, at what point? Before, during, after (first time) sex?”
Yeah, definitely ask her. Do what I wrote here:
As in, if you’re too nervous to bring it up out of the blue – bring it up whenever you’re comfortable. Be honest about it as early as you possibly can be. Usually easiest right after sex, when you’re both lying together catching your breath. Just lie together for a bit and then bring it up – “ever tried anal sex? I’ve never done it before, I wanna try it.”
“Or should I just put my lubed up finger to her asshole (without saying anything)”
No, dude – if you’re even asking the question the answer will always be DON’T just do it without asking. Better to bring it up with her first, since you haven’t done it before and don’t know what you’re doing yet.
” or just pretend like nothing happened”
No. Never ever ever ever ever ever ever do this. Ever. With anything. That’s autistic. She’s on your team, remember:
“On the one hand, the thought of verbalizing the action of anal sex out loud in bed (“I want to fuck your ass / Do you want to try anal?”, etc.) seems “unsexy” to me”
How is that unsexy? That’s literally foreplay/dirty talking.
In summary: Take things slow and talk to her about it first. Tell her you haven’t tried it before and want to explore it with her.
Lemme know how it goes mate. Have fun.