I will be visiting Chicago soon and am eager to have my first shemale experience. Looking for a very feminine bottom who is still functional.

Me too!  June 24-27 only. I hope to find sexy, classy TS pre-op and fully functional.

My top two:
1. Brasil - expensive but worth it
2. Sissi - a close second
Both would be a good choice.

Check the TER reviews of Sissi (now goes by the name Nashali), Brasil, and Melinda (used to be named Zindy and Melissa).  Alexa is versatile.  See if their reviews met your requirements.