Just a little longer

"Fine, let's show Emma one more toy." You respond.

"Thank you so much sir." Diane says.

"That's ok. Now let me get that out of there before it gets lost inside. You've had enough visits to the emergency department for lost toys this year." You say.

It was true. Your girlfriend's mother had a habit of losing toys up her loose ass, resulting in a rather embarrassing visit to the hospital to have a doctor reach their arm up inside of her and pull the toy out. **** to avoid another such visit, you get down on your knees behind her and slide two fists effortlessy inside of her ass. She moans like a whore as you start rummaging around within her rectum, feeling for the familiar hard silicone of the dildo. After not too long, you're able to grab a hold of the base and start sliding it out inch-by-inch. A process accompanied by the wet sloshing sound of Diane's ass coupled with depraved moaning from her other end. As you pull the whole thing out, you lie it against her back, showing just how impossibly deep it was inside of her, measuring almost the entire length of her torso.

"I can't believe that whole thing was inside of you." Emma says, her cheeks flushed red, perhaps embarrassed about complaining about her little plug earlier.

"Hmmm, let's try something a bit girthier this time." You say, reaching inside the bag of toys and producing a ridiculous pink buttplug.

The toy is practically the size of Diane's head. Emma stares at it wide-eyed, completely speechless, as you pull it out of the bag. Diane looks at it with a slightly shocked expression too, seemingly remembering the last time she came face to face with this particular toy. On that occasion, she had landed herself bent over a wheelie chair in the middle of a crowded office bullpen. Around her was a circle of summer interns, scrawny young men all looking to land a permanent position at your company. Their objective to secure their position, be the one to shove the ridiculously sized dildo into Diane's rear end. Behind them the whole office was watching, taking bets on who would be the one to finally get it in. Each time, you would spin Diane on her chair and whoever her ass was pointed at had a chance to shove the oversized anal toy into her ass. It took dozens of attempts before one of them finally managed to **** it in, at the end of which Diane was a sweaty mess from the repeat attempts at getting such a large toy into her ass. She had wound up in such a predicament as punishment for showing up several hours late to work because she lost track of time at her local gloryhole. It had become a real addiction for her.

Many nights, when she had the energy left after work, she had found herself wandering over to the local sex shop with the gloryhole booths out the back. They knew her as a regular there, greeting her by name and sending her to her usual booth. She would always tell herself that she would just suck a few cocks and then leave.

And then almost every time without fail she would find herself playing with her pussy whilst she sloberred all over those thick pieces of man meat.

From there it didn't take long until she was sliding her skirt and panties down (if she was wearing any), so she could back her ass up against the wall and slide a cock inside.

On this particular occasion, she enjoyed herself a little too much. Couple that with it being a particularly busy night in the store (word often spread fast when this particular whore was working one of the booths), and she found herself servicing cock after cock after cock...

By the time she finally emerged, covered in sweat and cum, she was already several hours late for work. She had raced into the office, still exhausted from a sleepless night of pleasuring herself with whatever man-meat poked through the holes in her three walls, but it wasn't enough to save her from her fate. It was a harsh punishment, that she clearly remembered well given her reaction to the enormous plug in your hands.

"You're... going to use that one again are you sir?" She asks hesitantly.

"That's right. Don't worry, I'm sure it'll slip in much easier than last time." You say with a chuckle.

As you step up to her ass, you notice Diane tense up, bracing herself for what's to come. Emma remains speechless as she stares at the biggest buttplug she's ever seen in her life. You push the tip against Diane's well lubed ass. The plug gest about three quarters of the way to the base with ease before coming to a halt as it meets resistance from the MILF's ass.

"Mmmph. Oh fuck!" Diane moans as you continue shoving the plug against her ass.