Jester wins

The Duplicate twirled the strap of a pink dildo strap-on between her fingers, a mocking, mischievous smile on her face. Both of them glided toward Caleb with a predatory air, while the real Jester clumsily fastened the strap-on around her waist.

To revive Caleb’s cock, they began caressing his thighs, calling him by affectionate nicknames, and kissing his flaccid penis until it began to stir and throb with arousal.

Their tongues teased the tip, forcing out spurts of semen left over from his previous orgasm, making his entire body tremble.

They used their tongues to tease and lubricate his little ass, even though there wasn’t much need.

To give me one last reason to wake up and keep fighting, Jester duplicate grabbed him by his hair and forced the weak wizard to eat her out, while the original blue-skin cleric kept herself busy donning the strap-on and kissing her clone, as she loved the way it felt.

When Caleb was finally hard and ready again, Jester dismissed the Duplicate and grabbed his legs, positioning herself between them and aiming the strap-on at the entrance to his ass.

“I hope losing and getting fucked feels good, little Caleb. It’s been a lot of fun!”

And the tiefling thrust forward, beginning to fuck the young wizard with her strap-on.

“Oh, you’re so loose. Don’t tell me… Apparently you’re Essek’s sissy, aren’t you?”

Caleb moaned. The sensation of humiliation and pleasure was intense, almost painless, and thinking of Essek fucking him at that moment only made his cock throb even harder, without needing to be touched.

After that, Jester began to fuck him harder, grabbing his ass and squeezing it with pleasure, forcing him to arch his back upward.

“Hey Caleb, look!” Jester took on the appearance of Essek, a dark elf with short white hair and a piercing gaze, but still with the tiefling’s wild smile.

Caleb knew it was just an illusion, a trick of the eyes, and that this wasn’t Essek. But Jester was so skilled and convincing—she could even change her voice and make her strap-on feel like a real, throbbing cock.

Caleb couldn’t resist and began thrusting upward in spasms, cumming into the air and all over himself, his eyes rolling back as he lost consciousness from the intense pleasure of this anal orgasm.

“I don't think there's anything else to add! The winner and an absolute hottie, Jester Lavorre!” At Kingsley's words, the audience erupted into deafening cheers, while Jester left the strap-on inside Caleb and stood up, intoxicated by the applause and whistles, performing pirouettes and theatrical bows.

She finished by posing with one foot on Caleb’s limp cock, which lay sprawled across his cum-soaked groin, pressing down and squeezing out the remaining spurts of semen, all while triumphantly flexing her surprisingly sculpted biceps.