No, you make her forfeit.

You keep fucking Ms. Devine, spanking her ass hard as you do.

With thirty seconds left, she's ****. That's when you make your move.

"Oh, btw, if she cums before you do, 'Teach, then I'm going to fuck her in the ass."

The MILF Teacher freezes up, while you smile at Kristi. She likes your ploy.

Being ever the nice woman, she can't risk her Student being fucked in the ass by you, so she slows down and barely touches the girl's pussy.

Time's up.

"You lose, Teacher. Kind of rude of you not to make her cum. How many times did I make you cum already?"
"Twice."
"Twice, what?"
"Twice..., Master."
"That's good. Now here is your punishment. First..."

You move her in front of Jenni, who you 'make' turn around and shove her ass in the Teacher's face. You tell her to lick both holes- now!

Nearby, you move Donna to the floor in front of Kristi and 'make' her eat out the girl's pussy until she cums. You 'neglect' to tell her to stop at once, so you wonder when she will actually stop.

Back with Ava, you shove your freshly-lubed cock into her asshole, finding it loose enough for entry. You recall watching her let another Gardener fuck her there at least twice, so that's no shock.

You fuck her asshole for several minutes.

Jenni cums twice.
Kristi cums three times.
Donna cums once (playing with herself).
Ava cums three times!

She came more from the anal sex than you fucking her pussy- interesting.

You grab her hair and pull her head up, taking it away from Jenni's tight ass.

"Are you an anal whore?"
"Yes, Master."
"Do you make guys fuck your asshole?"
"Yes, Master!"
"Tell me that you're my anal whore," you command.
"I'm your anal whore, Master," Ava screams proudly.
"Tell me that you belong to me."
"I'm yours. You are my Master. Please keep fucking my ass forever!"
"You'll get five more minutes. You'll earn more for every new **** you help me catch. Agreed?"