I enjoyed my service time during the 70's, but had to lie about being a cd'er when I first enlisted. I think the question was "do you wear womens cloths" or something to that effect. I think the consensus is that the military is not as uniform as we always think it is and that you may never be found out or you may be found out and the local command may not care or you may be found out and they will care, worse case senario.
With all your best laid plans, it's still going to be a risk. If you get a secret clearance, the FBI will be around asking some of your family and friends about you. They may or may not ask about cd'ing specificly, but who knows what your friends may volunteer. The odds are you will be OK, but it's up to you to take that risk.
I think if I were to do it over again, I might would serve as a DoD civilian employee instead. That way you can still serve your country without all the rigamoroles of military life, get better pay and still enjoy the benifits of seeing the world on the governments dime.