The Intern: An Anal Training

"I hope you don't mind, but I think Ryan wants to fuck that wet pussy of yours again right away," Marcy said.

"You both own my pussy, Mistress," Judy responded, deciding that from now on, she'd allow Marcy to make all of her sexual decisions for her.

"Good answer," Marcy said, just as Ryan slid his fat cock into Judy's wet pussy.

"Ooooooooooh," Judy moaned, as her pussy was stretched again by the fattest fucking cock ever.

"Yes, Ralph is going to fuck your ass so good on Friday," Marcy said, as her man began fucking her pet vaginally.

"Oh God," Judy moaned, trying to focus on licking the pussy above her face, while also feeling the pleasure inside herself rising quickly.

"We can even set up a live feed so we can watch you," Marcy suggested.

"Yeah, I really want to see that," Ryan added, as he began fucking the MILF's tight pussy.

"Oh, God," Judy moaned, unsure how that could come to fruition, yet not worrying about the future, since she was so completely consumed by the present. Delicious pussy above her, amazingly fat cock inside her... orgasm rising quickly. Heavenly!

"Or maybe we could just have a free for all foursome fuck fest," Marcy speculated, as she enjoyed the eager, although reckless and random tongue licking from her pet.

"Yeah, I'd love to see you taking nine inches in that ass of yours," Ryan enthused.

"Nine and a half," Judy corrected between her licks and moans... her orgasm already about to erupt... after only a minute of cunt-stretching fucking.

"Yeah, I'd love to feel that much cock up my asshole," Marcy moaned, imagining such a long cock stuck deep up her ass.

"Oh fuck," Judy said, the visual of her man fucking Marcy really turning her on. She couldn't explain it, in the past she'd always been extremely jealous of any woman who even glanced at her husband that way, and had refused any sort of threesome when a couple of possibilities had presented themselves in their younger, wilder days, and yet now she considered the idea delicious.

"Do you want to watch Ralph hammering my asshole?" Marcy asked.

"Yesssssssss," Judy mindlessly agreed, her orgasm imminent, willing to agree to anything Marcy suggested, no matter how crazy, and this was fucking crazy!

"While I hammer yours on the same bed... this one," Ryan embellished, while really fucking her hard and deep.

"Oh yeeeeees!" Judy screamed, sounding like she was agreeing to the fat cock sodomy, but actually she was screaming from the orgasm that was hitting her like a ton of bricks!

"I think she likes it, and she'll be up for absolutely anything we propose," Marcy mused. "Now let's show her what your cock buried in an asshole looks like."

Judy's eyes went wide, but she quickly realized it wasn't her ass about to get fucked, as Ryan pulled out, left the room for a moment, Judy assumed to lube up his cock, returned and got onto the bed, straddled her Mistress, and slid his cock all the way into her ass with no hesitation whatsoever!

"Oh yes, stretch my asshole with your fat cock," Marcy screamed, the initial penetration always a mixture of pleasure and pain, both of which she loved, since his cock was just so... fucking... fat!

Judy licked the pussy above her as she tried to peer around her to see the cock in Marcy's ass.

"Oh yes, fuck my ass, fuck it hard," Marcy moaned, as she began talking nasty, like she always did when she had a cock in her ass.

"Do you like this, slut?" Ryan asked.

"Yes," both Judy and Marcy replied in unison.

Ryan laughed, as he slammed his entire cock into his hot fiancée, "Priceless!"

"Just keep drilling my asshole and show our slut how good an ass fucking stud you are," Marcy said, her orgasm rising from Judy's erratic licking and the deep ass drilling.

Judy licked and looked, not ever catching a decent glimpse of the cock in the ass, just Ryan's body moving up and down, and his big balls appearing, disappearing and reappearing very close to her chin.

"Yes, harder, fuck my ass, pound it, pound it good," Marcy rambled, by now bouncing back to take her man's cock as deeply as she possibly could.

Judy gave up on trying to lick such a moving target, and just watched as best she could as Marcy got her ass drilled.

"Oh yes, oh fuck, oh God, fuck, fuck, fuuuuuuuck!" Marcy moaned and then screamed, although those words took over thirty seconds to utter accompanied by another dozen deep drillings until her orgasm hit, and she sprayed her cunt cum all over Judy's face and her sexy new lingerie. And Judy noticed she certainly wasn't apologetic about squirting! Maybe all the best sluts did it!

Judy lapped up the juice as best she could while Ryan kept drilling Marcy throughout her orgasm, and she then collapsed forward, giving Judy a much better visual.

Judy still couldn't see the asshole, but now she could clearly see that fat cock furiously pistoning in and out of it.

"Come in my ass, baby, give me that load," Marcy begged, still enjoying her orgasm, and also looking forward to her pet eating the cum out of her ass.

"Oh fuck, take it, slut," Ryan grunted, as he spewed a big load into his woman's asshole.

"Oh yessss," Marcy moaned, loving the sensations of cum filling any of her three holes... but in the ass it really soothed her after an intense orgasm.

Once he was spent, Ryan pulled out, and Marcy immediately ordered, lifting a leg to allow Judy to slide out from underneath her, "Now get in there and eat Master's cum out of my asshole, slut."

Judy rolled over, sat up, and got behind her Mistress as Ryan backed away, and she gasped when she saw the huge gaping hole... how could the tiny hole she'd been examining and licking this afternoon even get that big? And now that it had, how could it ever recover? It looked completely and permanently destroyed!

"No sightseeing this time, just suck the cum out, Judy," Marcy ordered.

"Yes, Mistress," Judy said, this new instruction not seeming at all disgusting after she'd already eaten Marcy's asshole this afternoon. She leaned forward and slid her tongue inside the huge gaping hole, and swirled it around.

"Oh yes, rim it just like that," Marcy said, wishing she could watch.

Judy obeyed, and did reach for and extract a little cum, but not much.

"Lie down," Marcy said after about a minute.

"Yes, Mistress," Judy obeyed, those two words the ones she now seemed to use far more than any others.

Judy lay down, Marcy quickly straddled her face, and now the cum oozed out of her ass and dripped onto her pet. The cum first hit her chin, so she shoulder-walked slightly down to catch the cum from the ass directly in her mouth... the act so submissive, so nasty, and thus so delicious.

After a few seconds, Judy lifted up her head and sucked, attempting to retrieve more of the salty seed from the sweaty asshole.

"Such a hungry ass eating cum slut," Marcy moaned, as she savoured the slutty action.

"We need to get going," Ryan urged her.

"Yeah, yeah," Marcy sighed, as she reluctantly climbed down off her pet to stand on the floor.

Judy lay there, exhausted, but she managed to lift herself onto one arm, "That was totally wild!"

"And we're just getting started," Marcy smiled, as she went to her purse.

"That idea both excites and scares me," Judy said, in a playful way.

"Oh, just you wait," Marcy said ominously, returning with a small butt plug and a fingerful of lube. She lubed up the plug and said, "This will remain in your asshole at all times except when you need to, you know, until I exchange it for a larger one sometime tomorrow."

"Okay," Judy said, this project somehow not seeming all that strange anymore.

"So," Marcy began, as she brought the small plug to her pet's ass, "you'll need to wear panties tomorrow."

"I have permission to wear panties?" Judy asked.

"You do, my pet," Marcy said, "probably until Friday evening," as she slid the plug into her pet's ass.

"Ooooooh," Judy moaned, a little pain coursing through her, but it was more of a discomfort.

"Tomorrow you'll get a bigger one," Marcy said, kissing her pet's pussy lips, making her quake.

"You're sure you have to leave?" Judy asked, not wanting this wild encounter to be over.

"Sorry, but we do," Marcy said, as she got off the bed.

Judy slowly got off the bed, the thingy in her ass feeling very weird. "I'll walk you out." Then as she attempted to walk, the toy moving inside her, she joked, "Or perhaps I'll have to waddle you out."

"It takes a little time to get used to," Marcy said, "but very like a thong, eventually it feels as natural as breathing."

"I'll have take your word for it for now," Judy said, it not feeling anywhere near as natural as breathing.

Judy followed Master and Mistress out of her own master bedroom, and to the front door.

"Tomorrow your training really begins," Marcy smiled.

"So let me see: today I was fucked by your man, twice before taking a huge facial, then later on I ate your ass... twice... including swallowing down an anal cream pie, and now I'm waddling around totally awkwardly with a butt plug shoved up my ass. And all of that doesn't qualify as a beginning?" Judy smiled wickedly.

"Okay, okay," Marcy laughed, "your training continues tomorrow."

"That sounds more accurate," Judy allowed.

Marcy leaned in and kissed her pet, just lightly this time, and then sauntered out with her man.

Judy closed the door and rested, leaning against it.

Holy fuck... things had officially gotten out of hand!

She went to bed, and was so exhausted she immediately fell asleep[A1], totally forgetting she'd promised to call Ralph.

.....

WEDNESDAY MORNING

Before leaving for work, Judy practiced walking around the house with the plug in her ass. She also practiced sitting down with the plug in her ass.

At work, she had meetings all morning, which didn't require any walking at all since they were all held in her office, and it wasn't until lunchtime she was summoned to the basement.

Ryan was the only one there, and he asked, "Hungry?"

"Starving," Judy said, walking immediately to the stud, dropping before him, and taking out his cock.

"You're already very well trained," he observed, as she began stroking his cock.

"And your cock has already become my fucking addiction," Judy replied, and without needing any prompting, she took it into her mouth and began sucking.

"I still can't figure out why your husband doesn't fuck you at least once every day," Ryan added.

He had no idea how attractive that simple statement made Judy feel. It was the ultimate compliment. It was exactly what she needed to hear, especially from a man.

"I'm serious," Ryan said, as he watched the hot older woman bobbing on his cock. "You're beautiful, you're a great cock sucker, and best of all, you're a nasty slut."

"I bet you say that to all the girls[A2]," Judy replied coyly, allowing the heavenly cock to slip out of her mouth for a brief moment. She had no idea which movie or television show that quote, or some version of that quote came from.

"No, you're something unique," he said, as he slid his cock back between her great cock sucking lips and began to face fuck her. He really loved fucking a mouth, almost as much as he loved fucking a big booty's back door.

Judy focused on breathing through her nose, having long since become able to take all of her husband's nine and a half inch cock into her throat without gagging, so this seven inch one, even though it was a lot fatter, wasn't much of a challenge. But it was very satisfying!

He pumped his cock in her mouth for three or four minutes, impressed by how easily she was taking his entire cock, before he grunted and deposited his load down her throat... Marcy had given him crap for getting so much cum on the slut's dress yesterday.

Judy swallowed the load, always loving the smooth sensation of cum gliding down her throat and filling her belly.

He pulled out and said, "You really are a hot nasty bitch."

"Aww shucks! You know just how to woo a slut," Judy retorted playfully, licking his cock head where a drip of cum still remained.

Two hours later Judy was responding to emails when Marcy marched in and ordered, "Get up and bend over, sexy."

Judy got up and walked around her desk, the position she went to when shifting gears from boss to submissive.

"How is your ass feeling?" Marcy asked, as she walked over and squeezed the big cheeks.

"Good," Judy answered. "It took a while to get used to it, but I got there."

Marcy pulled the small plug out and admired the small gaped hole. "Well, now your asshole looks just so fuckable."

"Sweet words I never imagined an intern saying to me," Judy laughed, as she felt Marcy's tongue swirling around her butt hole, and even going slightly inside.

"Such a delicious little asshole," Marcy continued, worshipping the hole... a gaping ass her kryptonite. She was here to install the second and larger plug in her pet's asshole, but she couldn't resist doing a little dirty dining first.

"Eat my asshole, Mistress," Jane moaned.

"You're giving me orders now?" Marcy asked archly, in between tonguing the small hole.

"I'm so sorry, Mistress, I thought you'd enjoy my nasty demand," Judy hastened to apologize.

"I'm just kidding," Marcy said with a giggle. "One of the very first things I mentioned in that very first message I sent you was that I'm a switch. And now that we both know I have your complete loyalty, whenever my face is buried in your asshole, you may order me to do anything you want. I think we'll both get off on it."

"Mmmmmm," Judy moaned, enjoying the tongue in her ass, and this opportunity to be a little bossy. "Then, my sweet slut of a switch Mistress, get that tongue as deep in my asshole as you can, and tongue fuck it."

"You nasty bitch," Marcy said playfully, as she obeyed her pet's order.

"Yes, lick my hole, fuck it," Judy said, enjoying the physical pleasure and this moment of role reversal.

"I could eat this asshole all day," Marcy said, as she reluctantly stood up, once again admiring the small gaping hole, "But alas, I have a meeting in five minutes, and you have a second plug to start wearing."

"Aren't I in the meeting too?" Judy asked, as she turned back to see Marcy pull a much larger plug from her purse... easily double the size of the first one in all dimensions.

"Yes, you are," Marcy said.

"That isn't going to fit," Judy said.

"Trust me, it will," Marcy reassured her as she lubed the plug generously.

"But I can't wear that into the meeting and be able to pull off pretending to be normal," Judy said, even if it did somehow fit, but how the fuck could it possibly fit?

"You can and you will," Marcy said, as she positioned the plug at the slightly gaped hole.

"I'm feeling really nervooooooous," Judy started to say, as she felt her ass unnaturally widened as the plug slid inside her.

"See? It fits," Marcy said jubilantly, since the medium sized plug was now lodged in her boss's asshole.

"Holy fuck," Judy said, this time feeling a lot more discomfort than yesterday morning's brief fingering and yesterday evening's first plug,

"This one will take some time to get used to," Marcy said, as she pulled Judy's panties up for her pet.

"That's quite an understatement," Judy said, slowly standing up straight... her ass really burning.

"Don't worry," Marcy said. "Be a good butt slut, and I'll have a special treat for you later on today."

"What is it?" Judy asked, as she began walking around with the plug in her ass... this one moving around more as she did... inflicting some very noticeable pain, and just a little bit of pleasure.

"Well, it's eight inches in length, and I strap it around my waist."

"Mmmmmm," Judy said, as she continued walking around, continued trying to get used to the oversized object in her ass.

"Yes, you could consider it an alternate version of a double penetration," Marcy said.

"Really? That's on my bucket list!"

"In time, I hope to help you check off everything on your fuck-it list," Marcy said, enjoying the sight of her pet duck-walking around with the plug in her ass.

"Fuck-it list?" Judy laughed. "I love that."

"Okay, it's time to go," Marcy said.

"I'm still not sure I can pull this off," Judy said, not at all comfortable with the larger plug in her ass.

"I have faith in you, my nasty ass slut," Marcy said, kissing her quickly and slapping her ass.

"Ooooooooh," Judy yelped, as the plug slammed deeper into her ass for a moment.

"Sorry for not being sorry," Marcy winked, and sauntered out.

"Fuck," Judy whispered to herself as she walked back and forth for another minute before heading off to a meeting she was supposed to lead. And she was supposed to do it coherently.

.....

WEDNESDAY AFTER WORK:

Judy was waiting in her office for Marcy to arrive. She tried to do some work, but all she could think about was getting fucked by Marcy with her strap-on like she'd promised.

As she was waiting, Ralph called.

"You forgot about me last night," he said.

Shit! She had. Judy replied, "Sorry, it was a long night, and I was exhausted, so I crashed without even thinking."

"I see," Ralph said, just as Marcy and Ryan walked into her office. "I hope it was a good night."

"Yeah, it really was," Judy said, as she mouthed, 'It's Ralph.'

Marcy grinned evilly as she locked the door, pulled her strap-on from her large bag, snapped her fingers and pointed to the desk.

Ryan took the snapped finger as being for him, so he briskly pulled his pants down, pulled out his dick, and hopped onto the desk just as Judy stood up.

"Well, what I'm really calling about, is I need to apologize," Ralph said.

"Apologize?" Judy asked, and she walked around her desk as she watched Marcy strip off her dress and fasten the strap-on around her waist. Judy took note of Ryan's hard fat cock saluting his women. "What for?"

"Put it on speakerphone," Marcy whispered.

Although nervous, she obeyed. "Honey, I'm going to put you on speakerphone, since I'm working on an analysis to satisfy a big client with some issues."

"You're still at work?" Ralph asked.

"Yeah, since you're out of town, I figured I might as well stay late and get some extra work done," Judy said, as she stroked Ryan's cock... feeling guilty... but also wicked.

"Well don't work yourself too hard," Ralph said.

"Oh, I'll try not to," she said, as she felt Marcy's hands lifting up her dress. "So, you were about to apologize for something."

Ralph responded, unaware that his wife was licking a fat phallus, "Well, I want to start out by saying not coming home to make love with you on our anniversary was a really shitty thing for me to do."

"You mean when you didn't come home and fuck me?" Judy asked, as she felt Marcy pulling her panties down... she wasn't sure whether she was getting her pussy or her ass fucked... forgetting briefly how Marcy had already hinted it would be her pussy... in some kind of unique double penetration.

"Yes, I failed to fuck you with my big fuck stick," Ralph said, knowing his wife loved his huge cock, dirty talk, and alliteration, all three.

"Exactly," Judy said, as she felt the strap-on poking at her pussy. "You haven't fucked me in a very long time, you know."

"I know," he sighed, just as Marcy slid her cock into her pet's pussy.

"Ooooooh," Judy moaned, unable to remain silent.

"Are you okay? Ralph asked.

"Yes, but your dirty talk is getting me horny," Judy said.

"At work?" Ralph said, this surprising him.

"Yes, my pussy is all wet for you," Judy said, as Marcy began slowly fucking her pussy and Judy stroked Ryan's cock.