Guys unless you have a big dick and I mean Big.... You are doing it wrong if it hurts. When I say doing it wrong it's not only how you insert it... But how you make her ready. First women like a bit of pain, being dominated and a bit of rough sex. Everyone has different level of what they do like but a little bit is liked by 99% of them.
So first of all you should get her off, make that pussy wet and hot, she must be horny, if she is the type that cum and then get relaxed and wanna sleep just tease her, don't let her cum. When she start asking for it, fuck her a bit and start fingering that ass, first pushing only on the outside then slowly penetrate it
She will like it, let her know you are getting horny as fuck about all this... This will make her happy and equally horny
When it's time you should use so much lube you can't almost hold your dick without it slipping out of your hand. Especially the first few times, it's not about pleasure it's about make her confident that anal sex is not about being hurt. Stick the tip in slowly, while you do, continue to touch her, massage her back, squeeze those nipples, kiss the neck. Whatever works to make her relaxed, and tell
Her to be relaxed, more she is tense more she contract the anal
Muscle and it will hurt.
So you are in maybe one inch, stop it! Don't go further don't go back as well, if she says it hurts a bit, comfort her and don't let her focus on it. But don't fucking take it off, she needs to get accustomed to it and the muscle need to relax and get stretched. So when you feel and she feels ok, push it a bit further.
It will take times and I mean it. 5 mins? 10 mins? Dpends. Told you... First few times it's not about pleasure it's more a lesson for both of you.
So when you have all of it in ( unless you have some long dick, then you put less of it in) start SLOWLY moving it, very slowly.
She will start liking it, you will love It and cum in 15 seconds. Ahahahha
job done
Make it pleasant the first few times she will ask for it the next few
It's all in their mind, of course some women are just... Not open with their own body, they don't know it and don't want to experiment with it. If it's your gf my suggestion is: find another one. If it's your wife already, work and fight for it. Make it happen, slowly, talk with her, make her understand sex is a very important part of a relationship.
Iron situation is very complicated. I had a gf like that, it was hard as fuck to make her enjoy it, she was just not much interested. Perfect women apart from that, but man... Sex for me is number one priority, couldn't stand her being so passive about it.
Anyway what worked for me was being straight and clear with her. I just told her that I loved blowjob and if she was not the one blowing me it would have been another women. I gave her the choice to be the one instead of another and she took it. She started blowing me. Did she loved it? Nope. Did she do it? Yes of course. But if you are to involved with a woman (marriage) you can't ask for everything, you should have made a better choice before, now you have to work with what you have.
Remember this, you saying: I would never cheat on her and bla bla bla, it's lovely but you shouldn't say it out loud especially yo her. Women must be kept in line, give them a too secure environment they fucking relax and get in charge. You need to let her be on the fence here and there... If you complain about sex she shouldn't be: I don't do it, period.
She should think; ummmm if he says it... It's important what if I don't want? What will
He do? Will he go and get it from
Another woman?
Doesn't matter if you don't want to do it and will not do it, she must be worried and a bit scared of it. She have to know that she doesn't own you. Do you get me?
All this is my opinion and just that, in my experience it has always worked well, but hey.... I could be dead wrong plus it's not a one size fit all kind of thing.
