I find that caress gains slow down considerably when you get up around 50 so I usually stop at 44 or 49 and just buy it up the rest of the way. 44 is good enough to make reasonable progress with girls who are at 20 respect and like you. It's nowhere near enough for a brand new capture with zero respect who hates you.
Ironically, I actually find that the success rate is higher to just request sex without doing seduction first to boost their happiness and affection a bit. Seems kind of odd that it would be easier to just tell them to suck your dick or let you fuck them than to butter them up a bit first with some kissing/massaging/caressing/etc. But that's the way it seems to work.
Take a bath first even if you have to do it alone. There's a significant penalty if you're filthy, which makes sense.
My strategy is to line up as many positives as possible, including avoiding negatives for poor hygiene or whatever, and persevere in trying to raise affection/happiness even if you've only a 20% chance, as you'll make progress with time. Improving the House as early in the game as you can manage makes for a higher baseline and soon enough you'll get their happiness up, a few hours at the Springs can do wonders for raising several girls' Happiness quickly. Get that Respect up, use whatever gifts, treats or whatever to raise Affection, and it really doesn't take all that long in my way of thinking to win a girl over to the point you can fondle them at least, and soon enough stuff them senseless.
He might have changed it some since I did that part of my Rise to the Ashes run but I didn't notice any more difficulty getting Charm for Caressing as it rose.
I try to start my Seduction attempts with her already aroused, as in from a Bondage session or taking a bath. Nowadays you can get some from Applicants too sometimes.