The tongue on a 101 is designed to turn straight up, hinged at the front of the bed. The trailer remains in conventional position. The portion of the tongue that extends under the trailer body, unbolts at its rear, as the lunette rotates upward, the rear most portion rotates downward and serves as legs. Some folks think the setup is to act as a dump trailer, which it can, sort of. But I think the design was originally to allow a space saving during transit, but still have the trailer fully loaded.
Off the top of my head, I don't recall the length of the 101's bed - maybe 7', so it would be close to being able to haul two in a 6x6 bed, with some hangover. I won't elaborate further on that one.....
Back the first in & tip up the tongue. Tip the tongue up on the 2nd, and run it straight in. I bet they will fit, some way.
Lee in Alaska