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Bib Fortuna would have taken every opportunity that came his way to thoroughly enjoy some exploit of Jabba's newest slave, as we see him all too quickly press his hand in against her neck after she reluctantly assumed the slave's embrace on the sail barge.
Just imagine a few possible situations that would've put Bib into very close proximity to Slave Leia:
Immediately after she was first captured - perhaps when she was stripped of her weapons and armor (and possibly more), Bib might've eagerly volunteered to assist?
Escorting Leia to and from the harem, but careful to not do anything that would get him in trouble with his (and soon, her) Master.
Presenting Slave Leia to Jabba for the first time (likely taking place of the guard that shoved her into the slave's embrace the first time, only now being the one to hold the newly half-naked Princess as she gets shoved into Jabba's waiting arms).
What do you think of these and other scenarios that come to mind in which Bib got away with sneakily enjoying the company of Jabba's new slave girl Leia?
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More Bib x Leia is definitely needed