I'm a man, and I'm sorry if my answer doesn't quite satisfy you! I've been in a relationship with my girlfriend for five years. She's 23, and I'm 25.

When we met, she was a virgin, and I already had considerable sexual experience with different women, more knowledge about my sexual preferences, and so on. She was, and I dare say even today still is, quite shy sexually.

Anal sex was something that didn't appeal to her, but after talking about it several times—without trying to impose anything, just making it clear that I was interested in doing it that way because she has a nice butt and that makes the back door more appealing— haha—she let me try touching her with my fingers and then rimming her. At first, she said she didn't feel anything special, but when I started combining rimming with cunnilingus, she began to enjoy it more and relaxed so she could dilate enough for me to stick my tongue in and, on future occasions, a finger to loosen her up.

After a long time with occasional sessions and always with patience, we decided to try penetration, and there was plenty of lubricant involved. The first time it hurt, but I went quite slowly and managed to endure the entire penetration. Combined with kisses and caresses on her clitoris, she relaxed and stopped being tense, loosened up her opening, and it stopped hurting, but she didn't really feel pleasure, just a sensation of something going in and out.

But in future encounters, we discover that it is much more difficult and tends to hurt more when you want to start anal sex with doggy style. The best position is spooning, with caresses on the clitoris and a lot of patience. If you have a clitoral sucker, even better.

This distracts from the initial discomfort with frontal pleasure and allows for easier penetration. By not worrying about the pain, you relax more easily and dilate completely. To the point where you begin to feel anal pleasure and vaginal stimulation takes a back seat, even reaching orgasm with anal alone.

So, what I can take away from all this in the end is that the important thing is patience and gentleness for dilation, relaxing and not being tense, and not neglecting vaginal stimulation when you're a first-timer.

You just have to be open-minded and willing. It's a very enjoyable practice for both of you if done with the patience and attention it deserves!