OK, non-shippy generalizations first. I don't think either of them is a virgin: Rock I'd imagine has had at least a few relationships, but maybe nothing long-term enough to get truly serious, and possibly not even much in the way of more short-term casual things since his college days -- when he joins the Lagoon there's no angst about leaving behind a girlfriend or even an unrequited crush, and his talk about the empty routine of his salaryman life makes it sound like he didn't really have a lot of time or energy to be dating much in recent years.
Everything about his old life, trying so hard to play by the rules and do everything the right way, makes me think he was probably doing the same thing in relationships -- dating because everyone else was and you're supposed to find a nice girl and get married eventually, going for all the most conventional romantic gestures on a date or following a mental checklist of what the advice columns say you're supposed to do in bed -- so worried about giving the right impression and doing all the right things that he's never really entirely relaxing and being himself. All the little bits where he seems to want to be more of a hero, even when the story and circumstances all work against it, makes me think he's probably got more than a bit of a romantic streak, too -- he wants to be something bigger and more dramatic than the drab little emotionally empty paint-by-numbers life he was living, and throwing his entire old life away to follow a scary violent gunslinger girl into the underworld or mouthing off about his ideas with a gun trained on his head shows the potential he has for making big, crazy gestures in chasing that more dramatic sort of life.
Revy, with all the hints of her horrible childhood, I'm guessing quite likely was sexually active from a younger age, and quite possibly not under the best circumstances; it wouldn't surprise me if she's had at least some unhappy runins with non-con/dub-con situations, especially before she picked up her gun skills, and we know that she's done sex work; the way she looks, and the places she's lived and worked, encounters with skeezy guys would be inevitable, and judging by how blase she was around Chaka, or the strip-club boss, she's experienced enough of that sort to be pretty blase about dealing with them.
I'm not sure if I can see her involved in actual prostitution rather than just the live BDSM shows that have been mentioned in canon, but her will to survive at any cost is strong enough that I wouldn't totally discount the possibility; if she were in a place where it was her only option, she'd definitely do it. I'm not getting any real sense that she's been in love before: emotional intimacy is I think something she'd be vastly warier of than physical closeness. I don't think she has a lot of body-image issues in general, she clearly has no problem running about in very skimpy gear or even being seen in her underwear; any insecurities there I'm thinking would be most likely to crop up only in the context where she's starting to develop an emotional attachment, and it would be more of an outgrowth of general insecurity about her self-worth and shady background -- like with those hints of jealousy around Yukio, I'd see potential issues there being less that Yukio was younger and conventionally pretty, and more that her lack of physical scars, conventionally feminine appearance and mannerisms, etc., all reflect a sort of good-girl innocence that Revy has never had -- so it'd be less "crap, she's so pretty and I'm not" and more "if this is the sort of sweet-and-innocent milquetoast girl he likes, I don't stand a chance".
Because writing meta for these two is so much easier than plotting porn...
Everything about his old life, trying so hard to play by the rules and do everything the right way, makes me think he was probably doing the same thing in relationships -- dating because everyone else was and you're supposed to find a nice girl and get married eventually, going for all the most conventional romantic gestures on a date or following a mental checklist of what the advice columns say you're supposed to do in bed -- so worried about giving the right impression and doing all the right things that he's never really entirely relaxing and being himself. All the little bits where he seems to want to be more of a hero, even when the story and circumstances all work against it, makes me think he's probably got more than a bit of a romantic streak, too -- he wants to be something bigger and more dramatic than the drab little emotionally empty paint-by-numbers life he was living, and throwing his entire old life away to follow a scary violent gunslinger girl into the underworld or mouthing off about his ideas with a gun trained on his head shows the potential he has for making big, crazy gestures in chasing that more dramatic sort of life.
Revy, with all the hints of her horrible childhood, I'm guessing quite likely was sexually active from a younger age, and quite possibly not under the best circumstances; it wouldn't surprise me if she's had at least some unhappy runins with non-con/dub-con situations, especially before she picked up her gun skills, and we know that she's done sex work; the way she looks, and the places she's lived and worked, encounters with skeezy guys would be inevitable, and judging by how blase she was around Chaka, or the strip-club boss, she's experienced enough of that sort to be pretty blase about dealing with them.
I'm not sure if I can see her involved in actual prostitution rather than just the live BDSM shows that have been mentioned in canon, but her will to survive at any cost is strong enough that I wouldn't totally discount the possibility; if she were in a place where it was her only option, she'd definitely do it. I'm not getting any real sense that she's been in love before: emotional intimacy is I think something she'd be vastly warier of than physical closeness. I don't think she has a lot of body-image issues in general, she clearly has no problem running about in very skimpy gear or even being seen in her underwear; any insecurities there I'm thinking would be most likely to crop up only in the context where she's starting to develop an emotional attachment, and it would be more of an outgrowth of general insecurity about her self-worth and shady background -- like with those hints of jealousy around Yukio, I'd see potential issues there being less that Yukio was younger and conventionally pretty, and more that her lack of physical scars, conventionally feminine appearance and mannerisms, etc., all reflect a sort of good-girl innocence that Revy has never had -- so it'd be less "crap, she's so pretty and I'm not" and more "if this is the sort of sweet-and-innocent milquetoast girl he likes, I don't stand a chance".