The bridge isn't producing true DC, rather a rectified sine wave with peaks at 1.414*110V ie 154V, like so:
You have several issues here. First, your multimeter when in DC position will "interpret" this waveform as it sees fit. If it's a good multimeter, it should average the DC value which is what you expect, then you would get around 98V ; 104V isn't too far. If it's a junk multimeter, it will display "something".
Now this gets more subtle. You drew a pretty large rectifier, and these big diodes have capacitance and non-zero leakage currents. The multimeter however has a very high input impedance. When measuring the output of a rectifier with only the multimeter as a load, diode capacitance and leakage (which are not matched between diodes) will change the value.
Solution is to add a dummy load, since the output is supposed to be 110V you can use a resistor of suitable value and voltage rating, or an incandescent lightbulb. But your 104V measurement looks OK.
Anyway. I think this also explains why you get 194 volts in the second measurement. Since you only connected one wire to the bridge, the brake will have a parasitic capacitance to whatever it's connected with (probably a large piece of machinery which is earthed). The transformer also has interwinding capacitance. To the high impedance input of the multimeter, a tiny current coupled through these parasitic capacitances appears like a legitimate measurement. Adding a load to the output of the bridge will fix this measurement problem.
Or you can simply connect the brake: if the bridge has 110VAC on the input, it isn't going to increase the voltage on the output...