One of the things that bothers men who didn't enjoy experimenting in their 20s is that when women start showing interest in them in their 30s, they often expect that those men are past the period of experimentation in sex and relationships, they know what they like and dislike and are ready to move on to the more serious part of the relationship, starting a family and the like.

But trying to ignore that those men didn't have the phase of experimenting and discovering what actually pleases them in sex and what doesn't, can easily cause resentment among men. Especially when all kinds of wild things from the women's past that she's tried in sex with others but refused to try with him start to surface.

Just imagine that man spent years and years putting his energy and imagination into various sexual desires while he was single and looking forward to finally trying them out. If he learns that he will never experience most of them in an LTR, he won't try them even once in his life, it will be psychologically difficult for him not to feel bitter.

How can a woman help men overcome this bitterness?

By being willing to enthusiastically experiment and rediscover everything possible in sex, so that her new partner can at least partially catch up on lost experiences. That she would be willing to experience different firsts with him again.

After all, that's one of the things that older, more experienced men appreciate about inexperienced partners, that they can go through their experimentation with them again, their first time in everything.

If a woman does this, she will also reduce a man's insecurities and thus his need to criticize her for her richer sexual past. On the contrary, her experience can suddenly be a certain advantage, as she can try the same things again and better.

EDIT: Frequent and recurring objections

I shouldn't have used "should". A valid objection, thank you. I guess I should have used could if she wants or can if she wants.

These men should seek professional help and not get into relationships. I agree that many people would benefit from professional help, these men included. But I also think, that in practice they do get into relationships and very few seek or receive quality professional help because of insecurity or bitterness from their own sexual inexperience or years of not having access to sex in romantic relationships, although they desired it. Not only mentally mature and self-confident people without any damage from the past enter into relationships. I'm not suggesting that these men start entering into relationships with women, I'm dealing with what can be done when a woman already chooses them for a relationship.

Women don't owe men anything. Also true. On the other hand: There are men who only start to gather more experience with sex and relationships in their 30s. Because only then they start to be attractive to women, women start to change their dating priorities and stuff like that. Many suffer from some inner insecurity because of this and may feel bitter. In the event that a more experienced woman chooses an inexperienced man for a relationship who wishes to experiment, this is my advice or suggestion on how she herself can help him and thus, as a result, their relationship and themselves, if of course she herself wants it and is willing and if it does not exceed any of hers boundaries and many more ifs.

I don't want an inexperienced man. A legitimate choice. Here I deal with a situation where a woman wishes to enter into a relationship with him. And not all inexperienced men have to have such baggage. I'm not describing everyone's situation, just a trend that I personally believe exists among men in this group.