- "You have served the Empire well, Commander. Deal with these Jedi traitors in the manner they deserve: Execute Order Sixty-nine."
- ―Darth Vader, to CC-1119
Order 69 was an order carried out by clone troopers during the execution of Order 66 in the Clone Wars, which saw the sexual defilement of female Jedi across the galaxy. The Sith Lord Darth Vader led his 501st Legion in capturing several Jedi on Coruscant and Kessel, and personally saw to the submission of his former apprentice Ahsoka Tano, and his wife Padmé Amidala.
- "A lot of innocent people died in that blast. I don't care about your reasons. I have my orders. This is going to come as a shock to you, but it's all the treatment a traitor to the Republic deserves. A hot, sharp shock."
- ―CC-1010, to Barriss Offee
Carried out during the Clone Wars in 19 BBY, Order 69 was an alternative form of Order 66, the order given to clone troopers to kill Jedi. Instead, Order 69 led to the clones sexually defiling female Jedi instead of only killing them, though some Jedi were killed afterwards. The order was also carried out by the Sith Lord Darth Vader against several individuals including the non-Jedi Padmé Amidala.
- "You are beaten. It's about time Cin Drallig's greatest pupil tasted failure. My clones will ensure this is one sparring session where you won't come out on top."
- ―Darth Vader, to Serra Keto
Order 69 was enacted on numerous planets across the galaxy, and saw clone troopers sexually defiling female Jedi. Aayla Secura was gang-banged in the exotic forest of Felucia by Commander Bly and his men, her arms bound behind her back as she was bent over and anally reamed by Bly while forced to suck off another trooper as a third ejaculated over her. On Saleucami, Stass Allie was made to submit to a skullfucking from Commander Neyo while held down by his men, and Luminara Unduli was tied to a giant tree on Kashyyyk to be forcefully taken by Faie and his Elite Corps, as a means of breaking the Jedi. Depa Billaba was wounded in Order 66 on Kaller, sacrificing herself to ensure her Padawan Caleb Dume escaped, and was gang-banged by Commander Grey and his men as part of Order 69.
Clone troopers captured several Jedi in the Jedi Temple on Coruscant during this time; Shaak Ti was captured before she could escape to be ravaged in her own Jedi Council chair by troopers of the 501st Legion, and Serra Keto was caught in the Jedi Temple data room to be used and defiled on the floor by several of Vader's troopers.
Barriss Offee, who had turned traitor to the Republic and been imprisoned for her crimes, continued to undergo sexual torture at the hands of Commander Fox, and was violated by sadistic electrical devices in her Coruscant prison cell. Although not a Jedi, Padmé Amidala also suffered during the execution of Order 69, being forced to kneel before the Sith Lord Darth Vader on Mustafar and take his cock in her mouth. The Sith made Amidala choke on it as he clutched the tearful woman's head.
Several Jedi made their last stand on Kessel, though were defeated by Vader and the 501st Legion. As a reward, Vader gave Sia-Lan Wezz, Shadday Potkin, and Bultar Swan over to Commander Appo and his men, who ravaged the Jedi women in an orgy. Appo himself fucked Wezz from behind, another trooper jizzing into her mouth, as Potkin lay unconscious and cum-covered on the floor, while Swan was double-penetrated by two clones. Vader himself confronted his former apprentice Ahsoka Tano, defeating her in a duel and forcing her to her knees with her clothing torn. Vader loomed over her with his lightsaber ignited, gazing down at the exposed woman in triumph.
- (First appearance) (First pictured)