How To Convince A Girl To Try Anal Sex?

Girl with an great ass on the beach.

Sex week, part three! I know of many guys that aren’t into anal but I also know that some would want to try it but they don’t know how. Do what you like to do, sex should be fun. From my experience it’s not only great but many girls love it as well.


50% Of Girls Are Into Anal Sex

Like I suggested in the post about sexhalf of the girls are into anal. According to my notes from last few years 40% of the girls I’ve slept with did anal sex. Because I had some one night stands where I didn’t try it (and had no chance to follow up) I estimate that as much as 50% of women might like that idea.

There was a girl with whom I had anal during our first night in bed. I even put a butt plug inside her. The following morning I came into her mouth and she later confessed “you know it was first time someone did that to me” – referencing the blowjob finish, not the anal.

I introduced many girls to anal sex. You can always tell when it’s their first time – apart from the wide opened eyes they get very excited about it and they’ll usually tell you afterwards that they have never done that before. When they aren’t in their early 20s anymore they tend to make a really big deal out of it.

None of the girls that did anal with me ever complained or did it only once so I guess I’m doing it the right way. Most of them welcomed it in our sex lives and enjoyed it from time to time. There were also girls who asked directly for it almost every time. Some had big orgasms during anal. I’ll never believe that women don’t like anal.

Yes, half of the girls won’t even think about trying it and you won’t persuade them (nor should you try to). But(t) for the rest it’s really something incredibly pleasurable.


Is Anal Messy?

Don’t worry, there won’t be any graphic details. While some might have completely wrong idea of how it looks like or even think that you need to convince a girl to take an enema (or five) to do it – it couldn’t be farther from the truth.

Unless she really has to go to the toilet then her rear end is clean and empty. There is simply nothing there and there are neither bad smells nor anything gross. If she’s not comfortable with you going through the back door then she will stop you really quick. It’s the same when she doesn’t want to try it at all – you won’t have a chance to experience anything bad.

I’ve been in plenty of situations where I had anal sex with a girl without special preparations and even without lube at hand and it’s perfectly doable. She can derive a lot of pleasure from it if you do it right.


How To Convince A Girl To Try Anal Sex?

Let’s start with basics. You don’t “convince” her nor you ask her for it. But that doesn’t mean you don’t need her consent. Think of it as of any other stage of seduction. You assume she wants it then test that hypothesis by trying a little thing and then gauging her reaction. If you suspect she might not be into it – don’t force it.

You don’t ask a girl to have regular sex with you, you just lead her to that. If she doesn’t want to – she simply won’t follow you all the way. She will stop you or voice her concerns. It’s exactly like that with anal. Remember: you don’t push her, you merely let her follow. Be civil.

A simple escalation ladder seems to work every time if the girl you’re dealing with ever considered having anal. If she is against it – it will fail at the first step and she’ll stop you. That first step is simply massaging her anus with your well-lubed finger while you’re having regular sex (any position).

Now you want a lot of lube or a bucket of spit. There’s no lubrication there so everything that’s wet and slippery helps, including condoms with extra lube but those will come of handy later. For now make sure your finger is wet and you’re not pushing inside but simply making circles around and through it applying very little pressure.

That’s the moment when she’ll push back your hand if she doesn’t like it. If she didn’t do that – anal just appeared on the menu.

Girl with an great ass on the beach.

But butt…


How To Have Anal Sex

Now you can safely suspect she might be into that but you still don’t want to go all in. If you go in too fast it will be painful and she won’t enjoy it (and won’t ever try it again with you). Don’t rush it, it’s a slow process. Keep fucking her and from time to time continue with the massage.

Next step will be getting tip of one finger inside her butt and that’s best done while you’re behind her (doggy style) or while you’re licking her pussy (good old “two in the pink, one in the stink”). Both approaches work well, it just depends on what you’re doing at the moment. If you have to stop yourself from finishing too fast then cunnilingus might be the better option.

One way or the other you’ll end up with just the tip of your finger inside her ass. Don’t wiggle it, don’t push inside, let it sit there. She has to relax and become comfortable with something in her butt. Continue fucking/licking her and take it out after a long time, relube and insert back again. You’re almost there.

Just kidding. It’s a long process. If you weren’t in that position before – switch to doggy style. Remember about tons of lube (or spit if there isn’t any around). Really. It’s no fun without it and it should be fun and exciting for both of you.


Call Me The King Of Anal

Now you might want to try something she will definitely enjoy – fucking her from behind with your thumb in her butt. Because thumb it’s thicker than other fingers remember to lube it pretty well and don’t move it after you put it in. Let the girl relax and get accustomed to the feeling. You’ll feel her anus relaxing after a while. You can even stop fucking her until that happens.

That’s when you might start to wiggle it and move it inside while still having vaginal sex. She should love it at this point so if there’s any discomfort or pain – you either rushed it too fast or didn’t lube it enough. If she really gasps and screams (in a good way) you might want to try to have anal sex.

It still isn’t the time for your dick. First – stop with the sex and focus on her anus. Go back to massaging it and putting a finger inside her. If you feel any tension – cease any movement. When she relaxes – go back to fingering her asshole. The goal is for your finger to move in and out without any friction. You guessed it – you need a lot of lube.

If she’s not relaxed completely you can try to use two fingers. If you can slide your finger inside her without any resistance you might want to try your dick. Stay doggy style, lube the hell out of everything and while spreading her buttocks with one hand – go in. You might not succeed the first time as it’s not easy, you need some force. If you can’t get in – go back to fingering.

If you did get inside her – STOP! That’s the most crucial moment and that’s where it’s way too easy to mess this up. Don’t even flinch, let her relax. You can whisper into her ear “I’m not going to move, relax”. It can take ages but after some time she will loosen. That’s when you might try to move a little bit. Nothing big, a mere suggestion of a movement is enough. Wait until she’s comfortable. Playing with her clit will help and it will make everything even more pleasurable.

Then, after a very long moment without any movement, while still taking care of her clit, you can try to slowly move back and forth. If she likes it and doesn’t stop you or push you back – great, you’re there. Be super considerate for a while. Then you can increase the speed and depth and have even rough, wild sex.


Anal Toys

I’m sure more girls like toys than anal so you might want to exploit that. Recently I’ve experimented with using a small butt plug instead of my finger. Girls go crazy for that one. I usually introduce it somewhere after I’ve managed to put a tip of my finger inside her when I’m sure she’ll like it.

Don’t shove anything inside her. It always follows the same scheme – massage, some pressure, more massage and then going in. Always with a ton of lube.

Sexy girl in a robe holding a pineapple.

“Easy girl, let’s start with something smaller.”

The advantage of a butt plug is that it’s designed to go inside her, it helps her relax and it stays there while you can pick any position you want and fuck her with the butt plug in. She’ll get a lot of pleasure from just that and it will prepare her for your dick.

When you decide it’s time for you simply take the butt plug out, relube and put it back few times to make her accustomed to the feeling. Then proceed as described above.


Enjoy Anal

Anal is what I really like so I try it no later than during the second sexual encounter with the girl. If you introduce something early on, it will be considered normal. If you wait as if it’s something weird – you’ll only make it weird yourself.

Don’t make a big deal out of it. If a girl thinks it’s bizarre or gross then treat it as any other shit test. Own it, say that this is what you like and if she tried it and didn’t like it – you won’t try to convince her. If she says that she never actually did it before then you’re halfway there. You planted the idea in her head, now wait until you see each other next time and just try the steps above.

You’ll definitely enjoy it and there is very high chance that she’ll be ecstatic.


Male-female relationships commentator. Also a traveler, adrenaline junkie and, believe it or not, introvert. Still obsessed with working out, coaching daygame and living life to the full.

Click Here to Leave a Comment Below 13 comments
Aleksandr - 2017-06-19


Aleksandr - 2017-06-19

Why “Convince A Girl To Try Anal Sex”

    tddaygame - 2017-06-19

    Have you read the article?

    1. “You don’t “convince” her”
    2. “From my experience it’s not only great but many girls love it as well.”

    Aleksandr - 2017-06-19

    1. Have you read the title of your own blog-post [this ain’t not article, amigo] or do you have a ghost-writer?

    2. So you do it to serve the bitches. Gotcha.

    tddaygame - 2017-06-19

    If you want to misinterpret everything that is being said to you then find another blog. Next nonsense comment is going to be deleted.

    Aleksandr - 2017-06-19

    Maybe you should simply rework the title into “how to prod a woman along towards anal sex?”

    tddaygame - 2017-06-19

    It’s obvious that the title is for “marketing” purposes. It’s searchable/sharable. I think it is clear in the text that you don’t actually ‘convince’ her. It’s done intentionally.

    Aleksandr - 2017-06-19

    Gotcha – I’m extremely new to internet marketing/SEO and these are the very first posts under my real name. Ever

    Apologies if I rubbed you the wrong way

    tddaygame - 2017-06-19

    No problem. It helps when you’re asking the full question instead of “Why?”

Aleksandr - 2017-06-19

That’s a feature – not a bug 😉

P.S. It would also help you ENORMOUSLY if you focused on marketing and not “marketing”

Lucas - 2017-10-25

Fvcking great post! It explains a lot. Gonna try it for sure.

A similar post about BJs and generally about stuff you want a girl do to you would be great as well. How to hint her to do it, is it OK to lick her pvssy and don’t ever get a BJ because she doesn’t like to do it, if she have to like it and if she doesn’t what you can do, why she don’t want to give you a BJ or sth else, but she did it for other guy ect. I have never found any good arcticle about that and I’m sure you can elaborate on that very very well 🙂

    tddaygame - 2017-10-25

    Thanks for the comment!

    That’s even simpler matter: if she doesn’t want to give you a BJ but she did for the other guys then you’re simply not that attractive to her. And not just sexually – in general. If she doesn’t like that or doesn’t want to try – it’s very often hopeless (or at least I’ve never stick around long enough).

    As for the “techniques” to get her into that the easiest way is to give your dick to her while you’re fingering her (while kneeling besides her). 69 is also a great idea.

    Yeah, maybe there is a post somewhere in there…


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