Basically, what's "too far" for me isn't "too far" for him. I don't think he fully registers his behavior as problematic. Though I haven't staged a big discussion about consent, I am still clear in the moment, every time, what's okay and not okay to do, and he still flirts with the line (at best) and tries to convince me to start or keep going, and definitely keeps up the emotional and physical pressure to consent. Basically, he resists taking "No, I'm hurt" or "No, I don't want to do that" as an answer.
I've incurred some vaginal tears from (mutually agreeable) rough sex. But later that day or the next day, when he's ready for more sex and I'm still hurting and clearly say so and express a desire to do other sexual things and avoid penetration, he will attempt to penetrate me, penetrate me, or grouse about my unsportsmanlike behavior like a spoiled child. He still jokes about consent. When we resort to other methods (fellatio) and he still gets off, he will still lodge a complaint or two about not getting PIV sex. Often I will say we can try penetration but if it hurts, he must pull out, and he'll penetrate me and clearly relish it, not reading the obvious signs of pain on my face, gasps of pain, or comments about pain. If he were in pain, I can't imagine getting off on his pain... the one time he got mildly mildly momentarily injured during sex, I was full of concern for him, so how can he pressure me into sex when he knows it will hurt me, or penetrate me when I'm in obvious pain? He does seem rather indifferent to my pain generally. While he's emotionally very supportive, he disregards any pain that I mention (severe cramps, illness, etc.) and I am a pretty tough cookie, not someone who gripes or complains about pain--if I'm in pain that's affecting me seriously, I'll mention it once if he asks, which is hardly an excessive play for sympathy.
Sometimes, he just doesn't read me at all during sex--mostly when it would be inconvenient for him to comply. He also continues to joke/make light of consent, which I always say, "I'm not comfortable with that" or "that's not funny." When he's trying to penetrate me/pushing his cock against my vagina repeatedly when I either don't want sex or want him to wear a condom, I say, "Is this fun for you?" or "This isn't going to work for you unless you're willing to hurt me! Are you?" He keeps pressuring me to try something new in bed that I've said I'm not interested in at this point, but he repeatedly tries to initiate and makes me feel guilty for denying him. Frankly, I would be more likely to try it if I didn't feel so pressured, but the act has become incredibly unappealing because of pressure from him.
To put it bluntly (which is weirdly hard to do), we've had less-than-strictly-consensual sex a few times, which is to say, sex after I say "no" or sex under conditions I've said no to (no condom) but where I eventually stop resisting verbally and physically. It feels like consenting in a way, but consenting just out of tiredness or because I don't want to see how it would unfold. I'm not suggesting that it would end in clear-cut assault, but I don't want to see how much of a response it would take from me to get him to stop. I don't really want to know that I might have to yell at him, for example, or knee him in the groin, to get him to stop. There comes a point when I just decide to negotiate.
These kinds of behaviors are starting to leech into my feelings about him and our relationship. I love him very much and can't imagine having a better connection or better chemistry with anyone else, but I'm not sure how to integrate his behaviors and comments that trouble me into my picture of him as a whole person.
I am not sure what I'm asking. For your experiences, I suppose, as far as you want to share.