Dear Jane: My Partner Doesn’t like Anal Sex / Oral Sex… But I Love it.

Dear Jane,

I started dating a girl who said ‘Nothing in the butt, ever.  It’s gross.’  How can I change her mind/trick her?


I love eating pussy.  But my girlfriend said ‘no’.  Summat about a bad experience with another guy and she doesn’t wanna talk about it.  Any idea why she’s being such a bitch?

Are very related, you are basically asking for something you partner is set against for their own personal reasons, and both can be had with time and patience on your side.

Anal sex is mind over matter, she feels it is gross.  Some people NEVER get over this mindset, others get curious enough to give it a try.  You need to hope she is the later of the two.  Oral sex could be the same way, in fact, many sexual acts are the same way.  Without a “want” to do something, people create reasons NOT to do something.  It is the classic trying to get kids to eat their vegetables situation.

With bad experiences, and dead set against mindsets you need to create a positive association to trick their brains (what, did you think I was going to say “roofie them”?).

How?  Be hungry for your partner, have sex with them like if you don’t, you’ll die.  Hold them to you, grab their ass while you’re fucking their brains out.  Kiss them like they’ve never been kissed before… and when their eyes are rolling back in their heads, their hair is a mess, and you think they’ll agree to do just about anything… let your hands stray to your desired area of conquest.  If you know your partner’s body like you should, and made them cum hard a few times, you’ll be surprised what they’ll let you get away with.


So you’re fucking her like there is no tomorrow, and you’re grabbing her ass and pulling her into you, holding her still, letting her feel your manly arms around her, sweating pure testosterone and doing EVERYTHING that turns her on (right?)… and she is a mess of streaked make-up, and girl cum going on her 3rd orgasm (I hope). You’re going to cup/grab her ass with your fingers dangerously close to her asshole. Try the Lotus position.  Don’t enter the danger zone, but be firm and let her cum in that position.  A few sessions like this, weeks may go by, but you’re  going to one day let a wet finger TOUCH the outside of her asshole (though, if you’re doing your job her juices should be flowing- haha).  Don’t apply pressure, don’t wiggle it, but hold onto her -kiss her neck, kiss her gooood- and let her cum hard juuust like that while you’re fucking.

Let her be comfortable with the idea that you are “there” but not “THERE”… and build up how hot, sexy, and how blissfully orgasmic she is.  Talk about how hot the sex was, and how hard she came, and how beautiful she is.  Ask her if there is anything else you can do to please her… then ask if she has been loving what you’ve been doing to her lately.  Sneak in that she came the hardest with your fingers touching her ass like you did.

If she blushes, and playfully slaps you… keep it up.  She may be too embarrassed to admit she likes it.  Pay attention to her oohs and aaahs, and eventually you’ll get your finger in there.  One day she’ll ask you to do it while her face is mashed in a pillow.  I can’t give you a time line, but it’ll happen.  She might think it is gross now, but when she realizes touching the area isn’t so bad, she’ll get curious to try more.  If not, better luck with your next girlfriend.


She has had a bad experience? She finds it gross? She swears it’ll never happen again?

She sounds like the “no no, no anal, nope never” girl from above.

For you though, it is a little bit more difficult to get your head down there than to sneak a hand.  For you, my trick is “the wetter, the better”.  Use your hands, toys, a silicone basting brush… anything you possibly can to make her cum while her  vulva is really wet to stimulate a mouth.  Try using warming lubricants, and create the same positive associations.  Let her know how beautiful she is, and how sexy her pussy is, and how badly you want to taste her.  Talking sexy while you’re skillfully manipulating her to orgasm goes a long, long way.

On the flip side, and this has to be said – you should respect your partner’s boundaries.  “No” does mean “no”, and it may be time for you to reconsider your relationship.  Breaking up because your partner wont let you stick your finger in her butt sounds immature. Especially if everything else in the relationship is golden… but it is also the beginning to a long road of fapping to anal/oral internet porn while she isn’t around.  Such desire, unfulfilled feelings and pressure, could lead to cheating.  Either work on the bedroom and any other relationship issues you have, or break up.  Everyone deserves to be happy.

Don’t kid yourself, have fun while you can and try doing different things together out of the bedroom to help one another see that “hey, paint balling – sky diving – playing video games – eating new foods – together is fun, maybe I should try oral sex again.”

Share your thoughts

  • MyVAG

    Jane this sounds dangerously like a surprise finger up the butt type of scenario…but I dig it. Patience is key, but we all know the saying "Give 'em an inch, they'll take a yard"…ouch!

    • @SexpertJaneBlow

      ah, you see, the difference is there is no surprise rushing into it… this is cunning and calculating – note the stress on communication and taking baby steps to prep what is to come :)

  • Sausage Mahoney

    So is it a bad idea to yell 'Surprise!' and jam a dildo up there?

  • Bigger Than Blogging

    I think that most girls tend to really lose their inhibition with anal when you slide down from eating her pussy and delicately tickle her ass. Generally, do this when you know she's clean or fresh from shower or you and her will both be uncomfortable (last place you wanna be in bedroom). But… some girls it just takes time. Maybe alcohol and a pain killer. But I think if you try and push the right buttons aside from the anxiety most girls would LOVE to skip the first few tries and just be able to be that bad girl ass fucker.

  • DF

    I am a straight guy who loves to have his ass licked or probed by my wife and she IS DEAD AGAINST IT! She likes to give head but i cant cum from a blow job i need the anal play. Is there an Item out there that i can use while she is sucking me off that she wont be able to tell i have it in me? please help…