1. Monday, March 17th I had unprotected oral sex with what I now know to be a transexual CSW. I am in a committed heterosexual relationship so I asked before the instance when the CSW had been tested and she said 2 months prior but that she gets tested every 3 months. I also asked her after the fact if she had experienced any open sores as from reading your other answers that is about the only way I would contract Syphilis from this exposure. As for Gonorrhea and Chlamydia, I took a urine test Monday, March 24th 7 days post exposure and as of yesterday it was negative and I have no symptoms. From the sound of your other replies this test can be seen as conclusive, am I correct? In regards to my risks for Syphilis based on the details described above and the fact that it was receipt of oral do you think I need to wait 6 weeks before resuming my normal sex life with my normal partner.

2. Last week, March 21st after arriving home from my work trip, I went to a massage parlor and got a handjob, kissed (no french kiss) and sucked on the CSWs breasts. Based on your other answers all three of these are zero risks exposures am I correct in my thinking there as well?

1.  Your questions for your CSW partner establish that she takes precautions and is rather low risk risk.  As you already know, amongst penetrative sexual acts, receipt of oral sex is lowest risk.  Your testing proves that you did not get gonorrhea or chlamydia and your likelihood of syphilis is very low.  In your situation I would not feel the need to wait longer before resuming unprotected sex with my regular partner.  

2.  I agree, kissing, sucking a partner's breasts and receipt of masturbation are no risk activities.

Again, congratulations on your approach to casual sexual encounters.  It will do much to keep you safe.  EWH

1. It was my understanding based on other similar questions that Transexual exposures were higher risks in that they are engaging in anatomically male on male sexual acts. Is the reason my instance was rather low risk even though she regularly engages in unprotected anal intercourse specifically due to the fact that based on my questions she tests regularly and seems on top of her sexual health as a priority? (on top of our agreed upon understanding that receipt of oral is low risk for majority of STIs)

2. As a general clarification, in the case that a person engaged in sexual exposure with someone with Syphilis. From my understanding the only way to get it is based on direct genital to sore contact with an active lesion? Or are there possibilities that even with no lesions the infected person could still transmit? 

Thank you!

1.  Correct.  Most transexual women do not have HIV but many do not do a very good job of testing and otherwise caring for themselves.  Your partner was doing a good job of testing and is taking good care of herself.

2.  Correct.  Acquistion of syphilis required direct contact with an infected site.  

EWH