Hello Kelly.
It took me an incredible amount of time before I was able to freely let my emotions take over. It can be really hard to let go. The first time that I really cried was almost 4 years ago and it was during a time of extreme family stress, nothing to do with TS issues.
For myself I only cry during extreme emotional issues. Tears will well up in my eyes during weepy films, or during happy times etc., but by and large it's still takes a lot to get the tears to flow. Personally I wouldn't fret, some folks cry at the drop of a dime, for others it takes extreme emotional turmoil to bring on the tears. I think that when the time and conditions are right the tears will come.
The important thing to remember is that each of us deals with emotional issues differently. If you watch you can see this at weddings and funerals. I guess it's true that men tend to hide their emotions or have difficulty showing them, but there are women who do that too, don't let the fact that you can't get the tears to flow be an indicator of male or femaleness, cause it's not.
Steph