Her ass finally gives way

The thing simply won't budge despite significant ****, to the point of having to use one hand to hold the poor MILF in place. Then, all of a sudden Diane jolts as it slams its way inside of her, only stopping thanks to the flared base.

"FUCK!" She squeals out as the plug finally goes the whole way inside of her.

"Oh my God!" Emma says, even getting startled herself just from watching the gigantic thing go inside another Whore.

You let out a sigh of relief, finally relaxing after spending some time exerting yourself to get the thing inside of her. Diane on the other hand is breathing deeply, catching her breath after having the wind knocked out of her by the plug.

"I think... you broke... my ass." She lets out, her voice strained by her tender asshole.

"I think we did that a long time ago." You say with a chuckle.

"I can't believe you got that thing inside of her." Emma says, still in disbelief.

"I know, not even her daughters have been able to handle this beast yet, have they?" You ask, already knowing the answer.

"No sir, they haven't." Diane responds, a perverted sense of pride in her voice.

"I guess Diane here has a few years extra experience taking it up the ass, don't you?" You say, making Diane look a little more embarrassed than proud now.

"Well I don't think I'll ever be able to take something that size up my ass. I feel like I can barely move my legs with this one inside me." Emma says, still staring incredulously at the enormous plug wedged up Diane's ass.

"Hmmph, I guess we'll just have to wait and see. You're right though, Diane has impressed us with her talents here today. I think you deserve a reward." You say, bending down to her.

"Thank you sir." She responds, a perverted smile growing on her face.

You reward the obedient MILF by reaching down between her legs and starting to rub her pussy with one hand. The silence of the room is filled with the wet sloshing sound of her pussy as you rub it in circles, demonstrating the pleasure she finds amongst the pain of having such an oversized object rammed up her ass.

"Mmm! Oh! Thank you sir!" She moans in a high pitched voice, closing her eyes to focus on the pleasure she receives at your touch.

You knew your girlfriend's mother's body well now, rubbing in all the right places to bring her the most enjoyment. It isn't long before you can predict her next words.

"Oh! Sir! Please may I cum!" Diane begs.

"Go ahead, you've earned it bitch." You respond.

"Mm! Ahhhhhhhhh." She moans as her pussy starts gushing on your office floor.

Her orgasm doesn't last too long, granted it's purely from you rubbing her pussy with your hand. The whole while Emma is watching the perverted display from her chair, slowly growing accustomed to the way of life that an Office Whore leads here at Innovate.

When Diane's pussy is done squirting, she instinctively crawls backwards until her face is just above the puddle she made. Emma stares as she immediately starts picking up her mess off the floor, just the way a good Office Whore should. You step forward and continue rubbing Diane's pussy as she does so, rewarding her for setting such a good example for the newcomer. Once she's done, you decide to put on a new demonstration.

"Diane, why don't you show us just how comfortable you are with that plug inside of you." You suggest.

"Yes sir." She responds.

She hesitantly uses her hands to boost herself up into a standing position. She's a little unsteady on her feet at first, perhaps a result of her stripper heels, or maybe the giant plug in her ass, or more likely because she's so used to moving around on her hands and knees in the office.

Whe she's stood you can see just how large the base of the plug is, spreading her ass cheeks apart just to make room for itself. To your amazement, Diane's next move is to perform a squat for the two of you, albeit with some difficulty.

"Oooft. Oh. Mmmm." She groans as she squats down before standing back up again.

"Hah! Very impressive bitch. I think that's enough for now. Now do you see what a true Office Whore is capable of Emma?" You ask.

"Yes sir." She nods, astounded at the 'talents' of Diane.

"Good, now for the hard part then. Let's get that plug out of you bitch. Come lie down on this chair." You say, guiding Diane to lie back on a chair in your office.

She does as she's told, spreading her legs and raising them in the air to give you the best access to the plug in her ass. You pull her thong aside and grab with two hands around the narrow part of the plug, getting a firm grip before starting to pull with all your strength.

"Ohh! Oh fuck!" Diane moans, pushing the plug out with all her strength.

*POP*

Her ass suddenly gives way at the plug comes out with a satisfying noise.

"Oh my God!" Emma exclaims, looking at the MILFs ruined asshole.

Her backdoor appears a total mess. The sphincter is all puckered and thanks to her good going gape, you can see her bright pink rectum hiding away inside. Her ass is still trenmbling, almost like it's winking at you.

"Yeah, it doesn't take much to make her ass look like that these days. Go on Diane, why don't you show us that nasty gape of yours." You say.

"Yes... sir." Diane says, grabbing her cheeks with either hand and spreading whilst straining to produce a filthy looking prolapse.

Her rectum comes out in a bright pink rosebud, affording quite the shocked expression from Emma. The leftover lube from the toys oozes out of her prolapsed asshole.

"God you're such a filthy whore." You say.

"Thank you sir." Diane says with a smile, knowing it's a compliment.