M Madison is really hot and does S/O. Can be a bit clinical but that is her style.
Minax/Eve if she is in town.

What, specifically, are you seeking beyond strap on play? Give us a few details of your ideal lady's style. There's a whole range of amazing ladies in Chicago who love strap on play, including myself, but may or may not fit the bill depending on your other interests or preferred style. Tops, like asses, are not one size fits all.

Happy Hunting!

I've seen Mistress Madison and, although the session was good, I'd have to agree that she has a clinical style (sounds like that's not your thing). I've never seen either if these women I'm suggesting, but I have a feeling that your best bets are 1) Miss Maya Sinstress or 2) Lydia Schiller. Judging by their Eros ads, both are very hot looking and into "dark" role-play. If u were in your shoes that's who I'd look at- good luck.