argh, bad news mate.
Not sure whether this is the case with your bike, but it's possible.
On later model softails, when the rear pads wear too thin, the actual piston can get jammed in the bore, hence not allowing the brakes to release. Put simply, the piston doesn't run in the bore straight and grabs on it's way bakc after you apply the brake. This is reasonably common in HDs, but only when the pads get really worn and should be replaced any way. The older the caliper gets, the easier it is for the piston to jam. The work around is to make up a kind of a shim to put between the piston and the pad, so as to stop the piston from going out as far. Most of the time this cures the problem.
Of course, if you check and change your pads when needed it shouldn't be an issue. Remember, even when you never use your brake, there is still some wear because the pads sit close to the rotor. I never use my rear, except to hold the bike at lights, but I still have to replace the pads every so often.
Just my $0.02
Mick