Helping Diane

You arrive at Diane's office to find her lying face down on the couch, her fat ass sticking up in the air. The moment she notices you enter, she sloppily climbs up from her position and kneels on the floor in the usual waiting position.

"Good morning sir." She says with a smile.

"Good morning Bitch. What have you managed to lose up there today?" You ask.

"A big one." She says with a nervous grin.

Even as you look at her kneeling before you, you can tell that her belly looks a little distended. She isn't lying about it being a big toy in there.

"Well, bend over, let me take a look." You say.

Diane shifts forward onto all fours on the floor, her ass sticking high up in the air. You can already see her hole is a little gaped, suggesting she's been playing with some heavy duty stuff. You waste no time in getting your hands dirty to take a look. You slide three fingers in with each hand and spread her ass as much as you can. Her back door is seriously loose and spreads with ease, giving you a wide view into her rectum. Thank goodness you had her daughters teach her how to tighten her anal sphincter on command.

"Oooooh, you're so rough with my hole sir." Diane moans, sparing no effort to hide her enjoyment.

You notice Meg whince a little as she watches you spread Diane's nasty hole with ease. To your dismay, there's no sign of any toy, even with such a clear view. This job would require some deeper digging. You remove your fingers from her ass causing it to satisfyingly close back up, before taking a seat on the couch.

"Come sit." You say, indicating for Diane to move up to your lap.

She does as you say and climbs sideways onto your lap so her asshole is easily accessibly for your right hand. You once again get straight to business, inserting your whole fist into her ass. You keep sliding it further and further inside until you're almost elbow deep within her rectum.

"Oh God! I love it when you fist my ass sir." She moans.

To your surprise, there's still no sign of any toy. This thing must be buried seriously deep inside the MILF's well used asshole. You decide to try out another position and have her lie back on her desk, her legs splayed wide in the air to give you easy access. In this position, you can see your own hand through her belly as you rummage around inside desperately trying to find what she's lost up there.

"Mmmmm. Hello there." She says, smiling as she watches your fist move around inside her belly.

"I thought I told you to only use toys with a lead attached." You say, growing slightly frustrated now.

"I did sir, this one had a chain attached, but I lost that too." She says.

In order to get deeper inside, you have her bend over her desk before once again sliding your fist deep inside her, this time reaching your elbow.

With your fist this deep inside, you notice Diane starting to really feel it. She fidgets about as you savagely feel around her insides for any sign of a toy, growing impatient now. Finally, you manage to feel a small, cold metal object deep inside her. However, just as you think you manage to grab a hold of it, she shifts her body and you lose it.

"Damn it! I had it and you made me lose it." You exclaim.

"Sorry sir." Diane says, looking very apologetic.

"It's ok, I'll just have to get Meg to hold you still. Come and give me a hand will you." You say, motioning for Meg to come closer.

She nervously edges closer from her viewing point at the door and you position her so she's holding Diane firmly by her ass cheeks. With Meg keeping her stable, you reinsert your fist deep in your girlfriend's mother's ass and feel around for the chain that you lost. After some struggling from the poor MILF, you manage to grab a hold of it and thanks to Meg keeping her stable, keep a tight grip on it this time. You slide the chain out swiftly, pulling it out along with your fist. As you do so, Diane unleashes a torrent of squirt or piss onto the floor. You can't quite tell which one with her, since it could be piss resulting from you roughly pressing against her bladder or squirt as Diane reaches a perverse orgasm from your anal fisting.

With the chain in hand, you begins lowly pulling. Diane releases a symphony of squeals and moans as the oversized toy makes its way out of her asshole. As you pull your way to the end of the chain, you see a hint of purple pressing against Diane's butthole from within.

"Owww oww oww! Stop sir please!" She exclaims as you try to tug the tow out.

"What's the matter?" You ask.

"It hurts when you pull like that. Let me try pushing it out." She pleads.