The Intern: An Anal Training

Pressing her against the wall, Ryan bucked his hips and really fucked the MILF.

Judy was lost in lust as she babbled, the pleasure consuming her in ways she'd never felt, "Fuck yeah, ohhh fuck, yeah. Oh, fucking God! You're so deep in my cunt, and stretching me so fucking good!" (She continued babbling on and on rather endlessly, but you get the picture.)

"Isn't he amazing?" Marcy asked, as she listened to her boss making the moans and talking the slut talk like all the MILFs did once Ryan began fucking them.

Ryan loved looking into a woman's eyes as he fucked her... so lustful... so vulnerable... it was the ultimate look of beauty.

"Oh yes, fuck yes, best fucking dick EVER!" Judy answered, while her orgasm rose and he kept fucking her.

"Come, my nasty slut, come on Master's big fucking cock," Marcy ordered, as her own orgasm was about to erupt.

"Yes, oh fuck, yes, yes, fuuuuuuck," Marcy screamed, as her orgasm erupted and she squirted everywhere... soaking an astonished Ryan as he lowered her to the floor.

"Shit, she's squirting all over the place," he exclaimed, stroking his cock.

Judy was so embarrassed by how much she squirted, and was so ashamed she'd just cheated on her husband, that tears began to form, even while the most intense pleasure she'd ever experienced continued to cascade through her body.

"So hot," Marcy moaned, as she flooded her other pet's face.

"I'm going to come," Ryan said, as he slid his cock into her mouth again, close to coming himself, as he roughly face fucked her.

Judy focused on the cock in her mouth and the load in his balls, forcing her guilt away, and wanting to get this man off, to get his load.

"Come all over our pet's face, baby. And boss slut, beg for Master to come on you," Marcy ordered.

Judy didn't hesitate, as Ryan pulled his cock out of her mouth and beat it furiously. "Please, Master, come all over your slut's face; give me that load, I want it so bad!"

"Oh fuck," Ryan grunted, loving to hear a woman begging for his cock or his cum, and he erupted his load all over her face.

Judy moaned as she felt the warm cum splatter all over her face, and also onto her black dress.

As Judy rested against the wall, her cum still leaking out of her pussy, his cum dripping down her face, she began to weep.

"She's crying," Ryan cried out, concerned and suddenly helpless.

"Really?" Marcy said, this turn of events totally unexpected.

"Yeah," Ryan said, this not a reaction he was accustomed to; he had no idea how to deal with a weeping woman. To this day, the only time he'd ever seen his fiancée cry was the moment she'd heard the judge sentence him to prison. It had broken his heart.

"I'm so sorry," Judy wept, completely overwhelmed not only by her decisions, but especially by her squirting.

"I'm on my way," Marcy declared, rolling the office chair back and standing up. She disconnected her phone and said, "Thanks, slut."

"Thank you, Mistress," the older black woman responded, as she crawled out from under her own desk... a task that had given her intense shame the first time she did it, but now it was just a natural act that she craved on a regular basis.

Marcy dashed downstairs to the basement and found Ryan looking helpless and Judy collapsed on the floor.

"Go," she waved him off, and hurried over to her sobbing, cum-coated boss. "What's wrong, sweetheart? Didn't you like it? It certainly sounded like you did!"

"It was amazing, the best I've ever had," Judy wailed as if heartbroken, wiping tears, snot and cum from her face.

"And that's bad how?" Marcy asked, totally perplexed.

"It's just Ralph hates it when I squirt all over him, and then I caught the look on Master's face just now, and I felt so ashamed!"

"Oh, my darling, squirting is natural, I know Ryan didn't mind, he was just surprised," Marcy said, wrapping her arms around the weeping woman.

"And I feel terrible for cheating on my husband," Judy added.

"Oh, honey," Marcy crooned, leaning in and kissing her. Tenderly. Ongoingly.

After the raw fucking, the intense orgasm and the explosive facial, this was an experience completely different for Judy. Raw. Intimate. Body warming.

After a couple of minutes Marcy asked, breaking the kiss, "Do you understand how much you needed this?"

"Yes, but...."

"No buts," Marcy interrupted, putting her fingers caringly to Judy's lips. "You're a beautiful woman. You're a dirty slut, and I mean that in the best possible way, because so am I. You're a woman with needs. Your husband totally abandoned his manly responsibilities for months on end, and that's what led to this necessity."

Judy knew that was all true... although she really appreciated hearing it.

"Listening to you go ballistic while Ryan fucked you was so hot," Marcy said, as she cupped her boss's big tits and noted the spattering of white spots of cum on her dress.

"He was amazing," Judy said. She'd stopped crying now, and the soft look on her face was totally vulnerable.

"Yeah, he can really fuck," Marcy said tenderly. "He can also shoot up to ten loads in a single day."

"Fuck," Judy said, trying to imagine that cock pounding her through multiple orgasms and delivering multiple loads to her.

"Oh yeah," Marcy said. "The guy is a fucking machine."

"You're a lucky girl," Judy said earnestly.

"Oh, but you're a lucky woman as well, since he'll be pounding your three holes regularly," Marcy assured her.

"I can't imagine that fat dick inside my ass, or in any ass, for that matter," Judy said.

"It will take training before you'll be ready for it," Marcy said. "And we'll begin that training before you leave for the day. But you need to clean up now. You have a Zoom meeting in fifteen minutes, and you have a lot of cum stains on your dress."

"He came buckets," Judy said, looking down to see the white spots.

"He always does," Marcy agreed. "And you also have his cum all over your face."

"Right," Judy laughed.

Marcy helped her pet to her feet and said, still in her tenderest mode, pulling her pet close, "I'm always here for you, my pet. Yes, I will frequently use your face. Yes, I will fuck that pussy and ass so good and hard you'll come like the slut you are. Yes, I'll train your asshole to take Ryan's fat cock and your husband's long one. But I'll also guide you along your journey. You'll always be able to tell me anything you're feeling, anything that's troubling you, and I'll always listen. But be warned: I'll then always take action to address the issue, and you may not appreciate it, at least not at first."

"Everything you've told me so far is still so surreal," Judy said, as she went over to the large, dirty sink.

"All awakenings are exactly that," Marcy said.

Judy cleaned the cum off her face, and once she was back in her office, she changed outfits... she always had two or three extra dresses on hand in case of emergencies. She'd spilled coffee on herself on more than one occasion, or sometimes she needed a change of attire for a special client she was meeting with... and now she'd always need to be prepared for unexpected cum stains.

Tuesday late afternoon:

It was 4:30 when Marcy strode into Judy's office and said, "Let's get this training started."

Judy had taken some time to think about her multiple transgressions, especially sucking and fucking another man, and had gone back and forth between excessive guilt and lustful hunger.

Yes, she'd cheated on her husband.

But yes, she'd just had the fuck of her life, and had discovered girth is even more important than length.

And yes, her cheating had been a totally justifiable response to the horrible treatment from her husband, even if he didn't realize he'd pushed her into doing it. Yet. The jury was still out on what she was going to tell him, if anything.

And yes, she also realized these were just excuses to defend her actions, but yes, they were working. And well should they!

"Yes, Mistress," Judy obeyed, almost leaping out of her chair behind her desk, and hastening over to her young intern.

"Bend over your desk, my pet," Marcy said, having been a little worried that even after her pep talk, which Judy had seemed to take to heart, she could revert to being a mental mess after having sufficient time to reconsider her actions earlier today, but her instant and enthusiastic obedience happily informed her otherwise.

"Yes, Mistress," Judy unquestioningly obeyed, her pussy now constantly wet.

"Still horny?" Marcy asked, lifting up the dress.

"Twenty-four seven, dear Mistress," Judy replied.

Marcy pulled apart her boss's ass cheeks and admired the puckered virgin hole. Fuck, it was going to look so hot after it was gaped by her strap-on, and then by Ryan's ass destroyer. She asked, "Ever had your ass eaten?"

"No, I can't say I have," Judy said, just before she felt Marcy's tongue begin licking her smallest hole. In the stories she'd read, Mistresses usually didn't eat pussy, and she couldn't recall hearing of any who'd deigned to eat an asshole. Yet somehow she'd lucked into finding the perfect Mistress... one who gave as much as she received... and possibly even more. Who could be horrifically (and thus wonderfully) dominant at times, and yet who could also be utterly tender, like she'd demonstrated this morning. A Mistress who seemed to understand her needs and desires even better than she herself did. But for the moment, "That feels really nice," was all she breathed. And all she needed to say.

"Once you get past the initial prejudice that an asshole is inevitably a dirty hole, you're able to discover how it houses a plethora of sexual zones, and it can deliver intense pleasure to you," Marcy said, loving to have her own asshole eaten, and loving to dine on a sweaty, tangy asshole... and Judy's currently had both of those qualities.

"Feels good... weird... but good," Judy said, letting out the softest of moans. She couldn't explain how, but this experience was actually turning her on... her Mistress's warm breath enhancing the other, stranger sensations.

"Eating ass is normally considered taboo as fuck, and it actually is a little nasty too, so very few people ever take the chance to learn that an asshole tastes fucking good," Marcy said, swirling her tongue around the puckered soon-to-be fuck hole.

"I've never thought about it at all," Judy said, "I've always been stuck on that horrible experience all those years ago, and just left it at that," which was true, nor could she still imagine it tasting good, but she couldn't deny how much she was enjoying the lavish licking she was receiving right now.

"Oh, we'll be exploring everything together, my pet," Marcy assured her, and she stood up, bent over the desk next to her pet and ordered, "Now it's your turn."

Just stood up, looked down at Marcy's amazing big ass, not nearly as large as her own, but still delectable, leaned down and spread Marcy's cheeks, and stared at the asshole.

"Isn't it pretty?" Marcy asked, looking back and seeing her pet staring at her asshole.

"I've never really examined an asshole before," Judy said, as she stared at the small rosebud, wondering how Ryan's fat cock could possibly fit into it.

"Yes, it's a largely ignored bodily organ ," Marcy said. "It's almost impossible to see our own of course, except perhaps by using cameras. And unlike dogs, we're not usually in the habit of examining each other's. Which is a pity, really."

"I also can't fathom how you could ever take Master's cock into this tiny hole, even though I know you have."

"The anus has amazing muscles that can loosen or tighten to extremes most people have no idea about," Marcy said, loving to share her well-researched knowledge about the ass with anyone who'd listen.

"And yet I've never even thought about it until now," Judy said, still staring at the hole.

"Well, enough drooling, pet," Marcy said, "time to eat my asshole."

"Yes, Mistress," Judy replied, leaning down with a mixture of feelings washing through her, as she moved in close and could smell the salty scent, which didn't smell at all like feces, but nevertheless smelt a little like ass... as nonsensical as that sounds. She cautiously extended her tongue and licked.

"Good pet," Marcy moaned, loving the feel of a tongue on her asshole... plus the hot breath... the wetness... the naughty taboo of it...

Judy licked slowly, unsure of how to do it, surprised by the salty sweaty taste, which wasn't at all unpleasant.

"Start by licking in circles," Marcy instructed.

Judy obeyed, swirling her tongue around in a circular motion.

As the pleasure increased, like it always did for Marcy when she was getting her ass eaten, she ordered, "Now shove two fingers into my cunt while you continue eating my asshole. You can alternate between kissing it and licking it."

"Yes, Mistress," Judy replied, and she slipped two fingers inside Marcy's cunt while simultaneously kissing and licking her butt hole.

"Yes, yes, eat my asshole, slut, eat it good," Marcy moaned, as her orgasm rose.

Judy focused on trying to smoothly do both at once... until Marcy let out a load moan and came.

When Marcy had finished her orgasm, Judy pulled her fingers out of her Mistress's pussy and sucked the wetness from them.

"You love the taste of my cunt, don't you?" Marcy asked as she turned around.

"Is that bad?" Judy smiled.

"It's very bad, you nasty bisexual cum slut," Marcy smiled, before kissing her tenderly.

Marcy said, as she headed out, "Ryan and I will be stopping by your house around seven to run through our plans for the rest of the week. Be wearing something sexy... something you'd never consider wearing in public."

"Yes, Mistress," Judy said, deciding to stop at a lingerie shop on the way home to find something unbelievably fucking sexy.

.....

TUESDAY NIGHT

Judy picked out a sexy all-red corset outfit that showcased her large tits behind translucent netting and had garter clasps for the matching red stockings. In the past, something like this would have been all she'd have to wear to get Ralph hard and pounding her like crazy. But that was in the past. However, if Marcy's plan was successful, maybe in the near future as well?

She slipped into five-inch matching red pumps she hadn't worn in years, and practiced walking a little... feeling horny and sexy as fuck.

She was startled when her phone rang. It was Ralph. She answered, as she admired her looks in the full-length mirror, "Hi."

"Hey, honey," Ralph greeted, having felt like a complete shit ever since standing her up on their anniversary, especially because he'd promised to be home. After a night of drinking while watching strippers, and listening to the other married men bitch about how their wives never gave them head anymore, and how they treated the rare fuck they agreed to as if they were making a major sacrifice, he realized just how lucky he was. "What are you doing tonight?"

"My intern is coming over for some bonding," Judy answered, smiling to herself at her strictly truthful description.

"Really?" Ralph asked, his wife not one to bring her work home. And never one to socialize with her staff.

"Yes, I've realized I've been a bit of a bitch at work, and I'm trying to turn over a new leaf," Judy answered, again telling the truth, just not all of it.

"Well, I hope you have fun," he said, still a little surprised by his wife's plans.

"I imagine I will," Judy said, wondering what exactly Mistress Marcy and Master Ryan had in store for her.

"Will she be there soon?" He asked.

"Yeah, any minute," Judy said.

"Well, give me a call when she leaves," he suggested.

"Okay," Judy said. "If it's not too late."

"Planning a wild night?" Ralph joked.

"Yeah, a real all-nighter," Judy joked back, her husband knowing she wasn't a night owl.

The doorbell rang.

"She's here," Judy said, excited to see her... and also him....

"You'd better scoot, then. Love you," he said.

"Love you too," she replied, and as she hung up, she meant it. She did love him, but she was tired of wondering whether love alone was enough. But again, perhaps that would all change on Friday when he returned home, and if her training with Marcy was successful, she'd be able to astonish the hell out of him!

She went to her door and answered it just as she was dressed, not even considering the scandalous possibility of it not being Marcy and Ryan... but luckily it was.

"Shit, slut, you look good enough to eat, and fuck, and treat like a cheap tramp," Marcy said.

"As do you," Judy said, Marcy wearing an extremely short and lowcut black cocktail dress, black nylons and thigh high black boots.

"You both look fucking hot," Ryan said, slapping his fiancée's ass.

Judy said as formally as she could manage, "Master and Mistress, welcome to my humble abode."

They all walked in and Marcy said, taking a 360 journey around her pet, easily her most voluptuous one ever, "That... is one sexy outfit!"

"Thank you, Mistress," Judy said, enjoying the compliment and the lusty looks she was receiving from both her Mistress and Master.

Marcy squeezed the big booty. "I mean this succulent outfit shows off every fucking juicy curve you have."

"And I have a lot of curves," Judy joked, proud to know she had extra cushioning in all the right places.

"Fuck yes, you do," Marcy agreed, reaching around from behind and cupping her huge tits. "Now sadly, we don't have a lot of time tonight, since I forgot we're meeting some friends for drinks at eight."

"Oh," Judy said, clearly disappointed.

"But don't worry," Marcy said, giving each nipple a pinch.

"Oooooooh," Judy moaned.

"We'll make the time memorable," Marcy assured her, next giving each nipple a little twist.

"Okay," Judy moaned again.

"So let's go to your bedroom right away," Marcy said.

"Okay," Judy agreed, knowing she'd agree to anything that came out of this young woman's mouth.

As Judy led the extramarital couple to her intramarital bed, Marcy explained, "So the plan for the rest of the week is to get your ass accustomed to stretching around cock, so it can happily welcome your man's long cock as soon as he returns, and therefore... blow his fucking mind sky high!"

"That's in only three days," Judy pointed out.

"Yes, it certainly is," Marcy agreed, as they reached the bedroom. "Nice bed. Ryan, I told you we need a king-sized bed."

"Especially for foursomes," Ryan agreed, speaking for the first time since they'd arrived. However, his cock was obviously rock hard from his admiring this thick hot MILF. Apparently he was a man of few words.

"Exactly," Marcy said.

"But it's too big for a couple that doesn't fuck," Judy said, "since unless we make the effort, we don't even touch each other in bed."

"Well, that is what we'll soon be changing," Marcy assured her, as she grabbed Judy's hand, led her to the bed, and pushed her backwards onto it.

"Now," Marcy said, as she straddled Judy's face while facing forward, "we'll begin your anal training with a small plug for tonight."

"Okay," Judy agreed with a slight hesitation, as the pretty wet pussy hovered above her.

"And since you've cheated on your man with my man and we plan on your continuing to do so, I'll make a point of getting your man to cheat on you with me at least once," Marcy promised. "If you don't mind, of course."

As Judy began to lick the sweet pussy, this made a lot of sense to her. "Certainly Mistress, please be my guest," she agreed mindlessly, as she licked some heavenly nectar.

"I'm curious what nine and a half inches will feel like," Marcy said.

"Really fucking full," Judy said, between licks, "I think you're going to love it!" And then she felt her legs being parted as they dangled over the end of the bed.