Not sure if it's intended, but I've found a way to start pilot simulation with Linessa completely naked.
With L.O.V.E. 35 or higher, go to the Cantina or Common Area and initiate the interactions in the respective areas, after choosing to keep going in either one, Linessa is completely naked. If you go directly to the Holo-Dick and start pilot simulation she remains naked, allowing crewmembers to fuck her immediately.
I've also started the cellmate event with her completely naked, but I haven't found a way to do it consistently.