why would you accept offers of sexual relationships with such women a few years later

Because you prefer sex with "such women a few years later" (even if they "viewed you as second rate") to no sex?

The prospect of getting into a situation where a sexually experienced woman, er, handles me, feels really gross and unsettling

Okay, maybe not you specifically. Well, it's time for a survey... best taken outside of LessWrong (to get answers from more typical members of population, of course). My guess would be that most men would prefer sex with a woman who refused them ten years ago to no sex.

Speaking for myself, if every woman that refused me in the past would suddenly send me a message "hi Viliam, still interested in sex with me? no strings attached; just call me and you can have it", I would call a few (but not all) of them, and would consider it a very happy outcome. (It would be of course different if the "no strings attached" part would be missing. Then it would be merely a lot of "sorry, that ship has already sailed".)