The Intern: An Anal Training

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"Are you touching yourself?" Ralph asked.

"I'm actually about to fuck myself with a dildo," Judy said, just before she deep throated Ryan's cock for a moment.

"You brought a dildo to work?" Ralph asked, his wife continuing to astonish him.

"That's what not getting fucked for several months can do to a woman," Judy moaned, as Marcy bucked her hips deep into her... then Judy quickly deep throated Ryan's cock again.

"I'm so sorry," Ralph said, feeling so guilty, although his cock was now hard and gripped in his hand.

"If you're looking to make amends, you'd better be ready to fuck me good and hard when you get home on Friday," Judy warned, as Marcy began fucking her faster.

"I promise," he said, stroking his cock.

"I've heard that story before," Judy moaned, trying to focus on the conversation while getting her pussy banged, her ass passively plugged, and a very fat cock assaulting her mouth every few seconds.

"I mean it this time," he said.

"Why wouldn't you ever fuck me before?" Judy asked.

"It's complicated," he said.

"Are you jerking off?" she asked.

"I am," he said.

"Are you imagining yourself fucking me?" Judy demanded, as Marcy fucked her pussy, and now began pulling the plug out and pushing it back in.

"I am," he admitted, although truth be told, it was her ass he was imagining himself balls deep in.

"You're pounding me from behind with your big cock?" she asked, the double fucking really driving her wild, as were the brief air tight moments when she had Ryan's cock in her mouth and was surfing atop the euphoria of doing all this while she was on the phone with her oblivious husband.

"Fuck yeah," he moaned, stroking his cock, imagining her on all fours as he drilled her from behind.

"You're in my ass, aren't you?" she accused wickedly, her orgasm close and wanting to shock him.

"W-w-what?" he stammered.

"You never fuck my cunt anymore, because you want to fuck my ass, right?" Judy asked, as both plastic cocks went deep into her at once and then back out... making her feel so fucking full.

"Judy..." he said, but then had no thoughts to continue a sentence with, shocked by the accusation... even though it was true.

"Am I wrong?" Judy asked.

"No, dear," he admitted, feeling like a complete asshole.

"So what you'd really like to do is fuck my ass and tear it apart with your huge fucking cock?" Judy demanded, her orgasm imminent.

"And that visual is turning you on?" he asked, astonished yet again.

"Yeah, baby, I'd love to feel you tearing my asshole apart with your huge fucking cock," Judy moaned, before pausing to bob on Ryan's cock with a few hungry bobs.

"Oh, God," Ralph groaned, his balls about to erupt.

"Fuck me, fuck my ass," Judy moaned, as Marcy kept pumping both cocks in and out of both holes.

"Oh, fuck," Ralph grunted, spewing a massive load straight up in the air.

"Yessssss, fill meeeeeee," Judy screamed, as she came mere seconds after her husband did.

Ryan then hung up on Ralph and said, "Now get sucking seriously, slut."

"Yes, Master," Judy obeyed, as she devoured his fat cock and bobbed like a complete cock slut... as Marcy pushed the plug back into her asshole and left it there, while she kept fucking her pet's pussy.

Ralph called back.

"Don't answer that, slut," Ryan ordered, and Judy didn't slow down while taking all seven inches with each deep bob.

"The slut is airtight," Marcy said, as she kept fucking her pet, deciding to give her multiple orgasms.

"Next time it'll be my cock in one of those holes," Ryan moaned, as the slut really worked his cock over.

Judy did ignore the phone, since she really wanted Ryan's load.

"As you wish," Marcy said to her fiancé, having already decided that tomorrow she'd be the first person ever to fuck Judy's big booty.

"Don't stop, slut," Ryan said, as she continued deep throating his cock with smooth desire.

Judy sucked.

Judy got fucked.

Judy then swallowed when Ryan grunted, and unloaded his load into the MILF's vacuuming mouth.

"Mmmmmm," Judy moaned, loving the feeling of the big load gliding down her throat.

"He loves coming in your mouth," Marcy said fondly, sweating heavily from the workout of deep drilling her pet.

Once Judy had swallowed the entire load, she sat up and begged, "More, fuck me more."

"Not the most articulate begging," Marcy laughed, although she did indeed fuck her more.

"Just give me that cock," Judy demanded, a second orgasm already rising, even as the first was still fading away.

"That's better," Marcy said, as she pounded her pet's pussy as deep as she could... as hard as she could.

"Bang the bitch, baby," Ryan said, always finding that watching his wife fuck another woman with a strap-on was really fucking hot. He'd be banging her ass deeply just as soon as they arrived home.

"Yes, bang the evil bitch, Mistress," Judy played along, as she moved her hands onto Ryan's legs.

"Fuck, this is a real workout," Marcy said, sweat dripping down her forehead.

"Oh God, Mistress," Judy moaned, her second orgasm rising.

"Come, slut," Ryan ordered.

"Names, please more names," Judy begged, loving the name calling.

"Come, our bimbo three-hole MILF fuck toy," Ryan verbally assaulted her.

"Come, our cunt licking, cock sucking, ass taking slut," Marcy added.

"Oh fuck, I love being your fucking bimbo fuck sluuuuuuuuut!" Judy screamed, as her second orgasm in just a few minutes hit her.

"Such a filthy slut," Ryan said, as Judy came and squirted all over her legs as well as the floor.

"Such a good girl," Marcy purred, as she slowed down and began caressing her pet's back.

"So good," Judy whimpered weakly.

Marcy pulled out and watched more cum leaking out of her pet.

"We need to get going," Ryan said, getting off the desk, just as Judy's phone rang again.

"Keep the plug in that shit hole of yours until I remove it tomorrow," Marcy added.

"Yes, Mistress," Judy agreed, as her phone rang yet again.

"You may answer that now," Marcy said, giving her a quick kiss.

"Thank you," Judy said, feeling her cum still leaking out of her while she reached for her phone. "Hi, honey."

"Hey," Ralph said, unsure what to say now that she'd answered.

"Still horny?" Judy asked, somehow still horny even after her two intense orgasms.

"Not really," he said. "Are you?"

"Maybe," she said coyly, as she sat down on her chair and yelped, forgetting she had the plug in her ass.

"You okay?" he asked.

"Yeah, I just sat down awkwardly," she explained, which was kind of true.

"Why didn't you answer the phone?"

"Marcy showed up."

"Marcy?"

"My intern."

"Oh. Did she?"

"I think she suspected I was doing something."

"Oops."

"Yeah, oops."

"So that was some really crazy roleplaying."

"I figured it would get you off," Judy said, wondering if she could really get stretched out enough to take his nine and half inches in her ass by Friday... and she pondered how these crazy past three days hadn't only brought her sexual relief and anal awakening, but could perhaps result in rekindling her sex life with her husband, and saving their marriage.

"It was totally unexpected," he said. "Your attitude about our doing some anal play has always been 'Absolutely not'."

"Yeah, but recently I've been doing some reading about it."

"You have?"

"Yeah," Judy said, as she stood up and headed out of her office, but remained on the phone.

"And?"

"And you'll just have to wait until you come home on Friday to learn any more, because nothing's for certain yet."

"That's an eternity away," he complained, even though it was under forty-eight hours.

"I will tell you I have a plug in my ass right now," she revealed wickedly.

"No!" he gasped.

"Yeah, but it's nowhere near as big as your fucking cock," Judy pointed out.

"I'd be gentle," he said.

"Yeah, you're really known around our house for your gentle fucking," she teased.

"Butt... I've never heard you ask me for any gentle fucking," he teased right back.

"I've never heard you complain."

"True," he said, as there was a knock at his hotel room door. "Ah, shit."

"What?"

"Dave is here to pick me up."

"Where are you two off to?"

"Drinks."

"So strippers too, then," Judy accused. Not that she minded.

"There may be some strippers there," he chuckled, laughing at how well she knew him.

"Well, have fun."

"Love you."

"Love you too," Judy said by rote, although she actually meant it, before she hung up. As she got into her car, she couldn't believe how quickly her life had changed, and how those changes weren't yet finished.

End of Chapter 2

The final chapter The Intern: Anally Yours will be coming soon.

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4chuckssite4chuckssite11 months ago

557. Interesting story with lots of mistakes in word selection as are most of your stories. But this had a plethora of errors which makes me wonder about the proofreading. There is a good storyline, but I can’t really get too interested in the general topic of ass training and fucking.

AnonymousAnonymousover 1 year ago

so so...

AnonymousAnonymousover 1 year ago

so so...

AnonymousAnonymousover 1 year ago

I must not have read the same story as those who commented how well written it is. There were many, and I mean many, wrong words, often caused by missing letters, amongst other things. It came across as being rushed and quite sloppy. Very much unlike your normal product. Somewhat ruined an otherwise fun tale.

AnonymousAnonymousabout 2 years ago

Well, what I love about this story is that I think Marcy does care about not exposing Judy's sex life. Often blackmail soon rears its ugly head and lives are destroyed. I don't think that is going to happen and it would be very good to see blackmail not figure into this story.

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