I met a girl when I was 21. One day we were talking about past sex experiences and she told me an ex boyfriend tried to assfuck her once, but went in dry and ended up hurting her. She told me that she would never let anyone try again…
So I replied that was too bad, cause assfucking was my biggest sexual fantasie. She thought a few minutes and said that, in that case, she needed to change her mind.
And we did have anal sex. More even, she wanted it. In her mind. The idea could make her really horny and she seemed open to it. Untill we effectively tried shoving my cock up her ass. Fingers worked fine, but cock was unsuccesfull like 8/10 times. So every now and then there would be a good assfuck, but she would urge me to cum and pull out straight away.
So the assfucking part of the relationship slowly faded away, cause there’s no fun in assfucki g a woman who isn’t enjoying it.
Back then I read a lot of literature about anal sex and one thing kept surfacing: “if the heart says no, the ass says no”
Anal sex is something she must really want, in order for her to be really open to the experience. And my ex, well I think she simply didn’t feel it.
I divorced her after 23 years of marriage, she xasn’t happy anymore, and I met a new woman. This woman had been single for 5 years and I doubt she fucked a man in those 5 years. After 4 weeks she herself asked me if I wanted to use her other hole. Of cause I said it was a big fantasy of mine and we did out first assfuck the next night. I had to buy lube first. That first assfuck was while spooning and she told me she felt shivers running up her spine while I was assfucking her.
Finally a woman who loved it.
A least that was what she made me believe at the beginning of the relationship. Cause later on her tone changed. She never really liked it, I’d hurt her (while she never twitched) and I was a hidden gay guy. So I was back at square one and somewhat dissapointed.
In my single year after her, I thought it just is ine big lie. The “wolen can love anal” notion porn wants to plant in out minds. In that year I decided to let go of the anal fantasy and just take a woman as she comes, stick to mouth and pussy and shut up.
Then I met my current girlfriend. Beautiful mum of four, just out of a long, unsatisfying, marriage. The first night together we had sex. After that first sex the looked me straight in the eyes and said “you can do all you want with me” and first thing in my mind was anal. But I kept silent because I was sure I was hoping for something she wasn’t reffering to.
Then she said she enjoyed anal with her ex. That she only orgasmed while her ass was fucked and I was blown away. She exists !!!

Bottomline what I am going for here is: if it doesn’t work, it’s because deep down she doesn’t want it to work.
And if deep down she’s into anal, she will do anything to make it work.
I believe you can’t force anyone to enjoy something up their asshole if they are not eager to feel it.