Nata Summers gave the executive summary.  
 
I know, it's bizarre: in Canada it's legal to sell sexual services but not buy them, since December 2014. Prior to that the law was equally weird, everything about the biz was illegal except the actual exchange of money for sexual services, i.e; it couldn't be a pre-meditated act. In those days it allowed for the possibility a gentleman may give a lady a sign of his appreciation after the deed is done.  
 
I am unaware of any significant enforcement of the new law anywhere in the country. The greatest danger to you in Canada - which we all contend with - would likely be a scam, not LE. You can still negotiate an arrangement with an escort safely, particularly if she is established, which sounds like the case with the lady you have your eye on. If she has reviews and has been around for awhile all should go well. If she has no reviews on TER you should check out the local board for Toronto, it has high traffic.

Hi there,

You're correct that due to the advocacy of some the amazing women in our community, the criminalization of sex work was overturned by the Supreme Court. But then the legislature just replaced the laws with new laws that are different but still essentially maintain the illegality of sex work. There is some talk of an informal non-enforcement policy amongst Toronto police but nothing on the books saying that Toronto police won't make arrests for sex work. They're still making arrests in massage parlors and agencies for "trafficking".  

I think the best advice is keep things discreet and find reputable playmates that will be careful in protecting both of you from law enforcement. I know I always have the most fun when fantasy is kept secret! Would love to meet you.

xo

~Ash

It's ambiguously legal. Legal enough that you don't have to worry about police stings. Just play it a bit safe and contact reputable women and you should be fine.