Let's talk about the way Dennis views his encounter with Ms. Klinsky.
His line that sticks out to me the most is "I was willing." Despite the fact that Dennis was 14 years old and therefore could not consent to this, he views it, in retrospect, as a mutual encounter – in his brain, Dennis' place in this situation was voluntary and his decision, he was in control. He is so deeply opposed to the idea that it had been rape because that would mean that Dennis was not only vulnerable, but also taken advantage of, and further that he had never noticed it. It's also worth noting that he refers to himself as willing, not wanting – he was okay with it, not intrinsically desiring it.
To defend himself, he says, "I bedded an older woman, that's cool," meaning a number of things. Firstly, that he thinks of this as something he did because he wanted it, which is directly contradicted if he were to start thinking of it as a situation where he was raped, not willing; that it was him being tricked into submitting to her will, it takes away his perceived dignity, his autonomy, his control. On the other hand, Dennis thinks this is an inherently positive experience because it is "cool", regardless of his own personal interest.
Now let's talk about what this says about how Dennis views sex, in general.
To him, as established, it is good as long as it is cool – this implies that Dennis seeks out sexual experiences for the opportunity to, after the fact, flaunt his broad repertoire of diverse encounters. This thought process, sparked by his original first brush with sex, led Dennis into an urge to prove that he can pull things off, just like he believed he had "pulled off" sleeping with someone who knew better. This gave him something to brag about, something to make him look good – something profoundly poisonous to Dennis, breeding an obsession with his image and what he can do to make himself look better; less weak, less vulnerable. To make him feel in control.
This need to reclaim control feeds his obsession, his subconscious driving him to, as Charlie points out, do similar things to girls (typically young girls for further similarity, but Dennis is very careful that they are of age, unlike he was) in order to replicate the situation and rewire his brain into a scenario where he is in control. Dennis doesn't inherently want to do these things with these women, his brain craves it, demands it.
So why, exactly, does he submit to this urge, even if/when he doesn't want it?
Let's circle back to another thing he says about Ms. Klinsky: "a woman can't rape a guy." Dennis is so caught up in forcing himself into physically engaging whenever possible to maintain a sense of control that the concept of a man turning down a woman (a potential conquest, a power marker and a display of desirability and dominance over his peers) is essentially entirely foreign to him.
In fact, I'd go so far as to say that Dennis has a very uneasy relationship with saying no. This is an amalgamation of influence from various parties: to himself, it's just plain wrong; he's in a scenario where he's attracted to this girl, she wants him, he'd have to be insane to turn her down, there would have to be something wrong with him. From the girl's perspective (in his mind), he is showing vulnerability, taking them out of the heat and passion and bearing his own feelings, his own thoughts and opinions to her in turning her down, which risks losing control of the situation, of handing dictation over the interaction to her (something, something, the implication, blah, blah, blah...), rather than pushing through and keeping direction. To his peers, it makes him look like a coward, makes him look undesirable, like he wasn't able to pursue the girl, like he failed. All of these things strip him of control, leading him to be, in an external sense, "willing".
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