Yes, but she needs some preparation

There's a part of you that feels sorry for Doe, especially given the prospect of having her humiliated further. While there's never been something between the two of you, you were good buddies before the night of the bet. But you never imagined things going this far and they have gotten quite far after Tori stepped in. And you liked Doe for a long time and promised her that you would keep her safe. But, you tell yourself, she is not unsafe with you. And the promise was just about her not losing her job, which she is in no danger to. And she's always been hot as fuck. And the prospect of her being broken to become your sex **** incites your imagination. Sure, you have to share her with Anna and Tori, but for some reason that seems to excite you even more.

You nod. Tori, the good alpha submissive that she is, has read your intentions correctly. "You read my mind, Tori. I want to fuck Doe's cute little ass." And the redhead's cheeks flush slightly.

There's not much resistance from Doe as Tori unties her legs and wrangles her out of the closet, making her stand up on shaky feet. She's been bound for at least a couple of hours, and her legs are stiff and weak. The **** orgasms have sapped her energy, so Doe leans against Tori while the redhead drags her to her desk, and makes her bend over it with her legs parted. It's the second time in the day when she has to suffer this."Let me help, Sir."

You step back for a moment as Tori crouches between Doe's legs, burying her face between her cheeks. Tori's pink playful tongue starts circling Doe's anus, while she grunts loudly and bucks, but Tori is there to keep her in line. As much as she doesn't admit it, Doe likes it and the helpless look on her face is truly adorable. You can't resist the temptation to peel the tape off her mouth. "Oh god ...John... I can't..." She barely gets to say a couple of words before you pull out your cock and stuff it in her mouth. And after a moment of hesitation, Doe begins to suck it. She has really started to give in.

Meanwhile, Tori has been licking her anus, helping her gradually relax. She holds a bottle of lube in her hand (where did Tori get that from? the woman is, if anything, extremely resourceful). She squirts a little on her finger before she begins to probe Doe's anus, teasing it slowly. Doe moans and arches her back, but Tori grabs her hair and spanks her ass. "Don't move. Relax". Tori's finger keeps pressing gradually firmer, while Doe grunts loudly and bucks, until her sphincter opens up.

"She's very tight, Sir, but I'll have her ready in a couple of minutes." With her finger, and after a while with two of her fingers, Tori works what looks to be a generous quantity of lube inside Doe, who seems to gradually adjust, while her muscles learn to stretch for the first time. Her breath becomes steadier and heavier, and she starts to suck harder at your cock. "I'll have her wear a plug from now on, Sir." Doe widens her eyes, without taking her mouth off your cock and grunts loudly again, but Tori spanks her again into submission, then looks back to you apologetically. "I'm sorry, Sir. I should have asked if that's what you wanted for her." You nod.

"I'll keep that in mind." The picture of Doe wearing a plug at the office every day is surely appealing. But right now, you have something else on your mind.

You grab Doe's hair, yanking her head up and pull your cock out of her mouth. "Is she ready?" "She's all yours, Sir!"