You should be using a connector that's suitable for the full current of both motors; if the ESC wire is 20 gauge then two wires add up to a wire area that falls between 18 and 16 gauge. So as long as the connector is hefty enough to work with 16 gauge wire then you should be just fine. If it isn't, then I would question whether it has the current-carrying capacity for your motor combination.
The way I'd do this would be to strip both black wires a bit longer than the usual amount for connecting one wire to a battery terminal. Then I'd comb the strands out straight, put the wires together, and twist. I always pre-tin stranded wire, so I'd do that next. Then I'd shrink a small (maybe 1/4" long) collar of tubing around both wires to hold the mess together when the solder melts, string on a slightly extra-long tube, solder, and shrink. Then I'd repeat for the red wire.
If the mass of wire is too much for the connector, then it's a good sign that your connector is just too small.