kinda depends on who's getting fucked (you/her/both)
shemalecanada has listings, so check that out.
i really can't recommend any of the "girls" that currently live in the city, most are just crossdressers.
your best bet is waiting for a traveling girl, but availability sucks
sometimes it can be a few months before a decent one comes to visit or sometimes there's perods where there seems like there's a different qualtiy girl visiting every week
im submissive and i bottom so you might be lookng for something else but anyways here are the last 2 shemales i've seen and know that should be returning here:
Sunshine comes to winnipeg a few times a year and you totally can not go wrong with her. beautiful, classy, great service, just wow! really luvs to make sure you have a good time. my top reccomendation..... but I don't thnk she'll be back here until summer though ;_;
Lavinia Brazil is another i just saw a couple months ago. really hot, great dirty talker(which is great since most trannies i'm with are pretty quiet), big boobs and HUGE dick. she told me she's coming back to winnipeg in march.