One thing that you might try is the Sunday evening “Slow speed test” offered by K1USN. This is not a true test, but actually a way for CW hams to contact each other. 

Check out http://www.k1usn.com/sst.html

Then rather than sending out a CQ listen for CQs and respond accordingly. I think that this will get you contacts, improve your confidence and sending skills and overall will be a rewarding experience.

Let me know how it works for you. 

I have other suggestions so if you want I can be reached at K2PHD@....

73, Doc - K2PHD