The Intern: An Anal Seduction

"Please, we can make this work," Judy pleaded.

"Oh, I plan to make it work," Marcy said. "Last night I promised to help you become the slut you want to be."

"That was just talk," Judy said, trying to find a way to wriggle out of this.

"To tell you the truth, I'm glad it's you," Marcy said, as she flipped her stocking-clad feet onto the desk as if she owned the place.

"And why is that?" Judy asked, a little surprised this girl wasn't humiliating her like she had started to do, a little relieved that she wasn't, but also oddly a little disappointed. These mixed messages inside herself had her a muddled mess.

"First, I must say the nylons I instructed you to wear look really good on you," Marcy said, reminding her boss of last night.

"Uh, yeah, thanks," Judy said. "I can't believe I actually bought them."

"But you did, and that's because you're a submissive," Marcy reminded her.

"Look, that was just a moment of weakness," Judy pointed out, even though she knew that wasn't at all what it was. Discovering the online Mistress was her intern was wild, and although she knew she had to find a way to end this right here and now, her professional career could depend on it, she couldn't deny she found Marcy very attractive.

"Come here and massage my feet, my pet," Marcy ordered gently.

"Marcy, last night was a mistake," Judy said.

"We'll see; I don't intend to argue with you. But we do need to talk about what last night was, what today is, and what the future holds for us," Marcy said. "But we can do that while you massage my feet. Now get over here and do as you're told. You did promise last night to obey me mindlessly."

"But I never thought I'd actually meet you," Judy protested.

"Oh, deep down you did," Marcy said, knowing from experience that once she hooked a MILF, especially a married one, it always resulted in the older woman visiting their home to eat pussy and get her asshole sodomized.

Judy wasn't certain anymore what she knew and what she didn't, as she reluctantly walked over to this girl around half her age, and took a nylon-clad foot in her hand, surprised by how soft the nylon was.

Marcy considered stringing her along and really berating the bitchy boss, in some ways she deserved it for all the harsh treatment she'd given her and the other employees, but as her mother once told her, you can catch more flies with honey than with vinegar.

So instead she returned to their earlier conversation, "You know, my pet, I've always admired you."

"You admired me?" Judy asked, fully aware she'd been nothing but a cold bitch to her and now regretting it, not just because the girl now held her career in her hands, but for some reason now that she had the power, she wasn't retaliating for Judy previously treating her like shit.

"Yes," Marcy said, "and now it all makes sense."

"What makes sense?" Judy asked, as she massaged the silky sheer foot.

"Do each toe individually," Marcy instructed.

"Okay," Judy said.

"With your mouth," Marcy added, always loving the feel of a pair of soft lips sucking on her nylon-clad toes. First, it felt so nice. Second, it was a sexy image to watch. Third, it reinforced the hierarchy.

"But I...." Judy began.

"Complete obedience, my pet boss, complete obedience," Marcy reminded her, her tone, soft up until now, hardening just a little.

Judy sighed, "Are you sure we can't work something out?"

"We're working on that right now," Marcy said. "Now suck my toes, my submissive plaything."

Judy hated this treatment; she also loved this treatment.

The humiliation excited her; the humiliation also humiliated her. Which in turn excited her too.

Yet regardless of her mixed emotions, her pussy was leaking a little, and she was wearing no panties to catch the wetness, having obeyed her online Mistress, and thus also having inadvertently obeyed her extremely low ranking employee.

Yet not certain whether she was doing this because of her agreed-to obedience, or from the fear of blackmail, she bent down and took a pinkie toe in her mouth.

"Mmmmmmm, good girl," Marcy moaned, her feet being one of her many erogenous zones. She pulled out her phone and snapped a couple of photos.

"Please, don't," Judy pleaded, leaning away from the foot.

"These are just for me and Master," Marcy said. "I have a dozen MILF pets like yourself, and none of them have ever been outed by me. A couple of them have chosen to out themselves, but that's a different story. Now resume your task."

Judy again sighed, knowing she was helpless to do anything but obey, since Marcy held all the cards, and as strange was it was to admit, she found this mindless obedience, although it wasn't overly mindless since she kept protesting, felt oddly natural and soothing.

"Now I know why the woman I'd once respected has changed," Marcy said, having idolized Judy when she was younger, as a top CEO and spokesperson for women everywhere. She was thrilled when she landed this internship... well... until she met her face to face, and immediately learned what a bitch she'd become.

Judy, as she sucked on Marcy's toes, the task so menial and embarrassing, yet the salty, sweaty, silky taste surprisingly pleasant... and the scent subtly exotic, asked, "Changed? How did I change?"

Marcy explained, as she watched the powerful woman work her way from toe to toe, "Before I came to work here, I idolized you and thought you were a total badass. I admired how you'd worked your way up from being an intern like I am now, to running the entire show. And when I spoke with some of the longstanding employees, they all agreed you used to be a lot cooler. In fact, they used to love working for you. That was until you started throwing your weight around and becoming the biggest bitch ever. But after our little chat last night, I now understand why you behave as if you have the world's biggest stick up your ass."

Judy felt defensive about that appraisal at first. Yes, she had become bitchier in the past few years, but staying on top was exhausting. Yet she recalled she'd used to enjoy her job. Now it was just the means to an end. She was already beginning to realize this intern's summation of her was spot on. She'd used to be cool. She'd used to be well liked. She'd used to love her job. She'd used to train her interns, who would invariably leave to work for other companies and soon rise to the top. She asked, trying to act oblivious, "And why is that?"

As she wiggled her other foot and watched the CEO move to her other nylon clad set of toes, she pointed out, "I think you know the answer. It's because you're sexually frustrated."

"I don't think that's any of your business," Judy said, trying to hold on to a shred of dignity in this humiliating turn of events.

Marcy sighed, "First, it became my business when you willingly, and remember it was completely willingly, agreed to be my pet. Which means, although you may not realize it yet, your welfare is now my responsibility instead of yours, a corollary of which is you're not allowed to keep any secrets from me. Second, as I've already said, I'm not trying to blackmail you or humiliate you, although I suppose there will be some inevitable humiliation."

"Like sucking your toes while you sit at my desk," Judy mentioned sarcastically, resenting her predicament, yet also secretly enjoying it.

"Stop pretending you're not enjoying this," Marcy said. "Your words say one thing, but your actions, eyes and body are doing all your real speaking... and still... I'd like to help you."

"And how do you think you can help me?" Judy asked, for even if she did submit and get the fucking she craved, and explored the taste of pussy like she was curious about, it didn't address her marriage falling apart.

Marcy asked, "Are you admitting you need help?"

Judy didn't know what she wanted anymore. Yes, she needed to get fucked. Yes, she was undeniably sexually frustrated. Yes, she was secretly enjoying this humiliation. Yes, her pussy was on fire. Yet she wasn't confident she could really do this... online roleplay was one thing, but whatever this was becoming, was something entirely different. Added to the fact the first person she'd seriously explored with online turned out to be her intern was a twisted irony of fate. She said, saying how she was feeling, "I'm not sure whether I do or not, but I do know I'm not comfortable discussing my sex life with my intern."

"You told me lots yesterday," Marcy pointed out. "And at the time, as far as either of us knew, I was a complete stranger."

"But yesterday I didn't know it was you," Judy pointed out, as she sucked the middle toe between her lips.

"Does that matter?"

"Yes. Yesterday I was sharing with a complete stranger I'd never meet with no risk, but today I learned you're my intern."

"You gave me your real cell number," Marcy pointed out. "That was very risky. With it, anyone could discover your true identity. You're lucky it was me, and not some unscrupulous snake who'd decide to destroy your career."

"Yes, that was very careless," Judy agreed, realizing how that one moment of weakness could have led to just such a disaster.

"And you then obeyed all my orders, I see," Marcy pointed out. "According to the pictures you willingly, and I imagine eagerly sent me, you aren't wearing any panties."

"I'm not," Judy admitted, as she moved to the second to last toe... oddly beginning to feel more comfortable in this situation. She was naturally submissive, so her sexual obedience came naturally, it was such a polar opposite of the persona she portrayed at work or in public.

"And you obviously did some serious shopping," Marcy continued, glancing pointedly at the four shopping bags in the office.

"Yes, I figured you were right, and I should update my wardrobe," Judy explained.

"I didn't even tell you to put them on while you were still at work."

"Yes, but you did tell me to send you pics wearing them," Judy pointed out.

"True," Marcy agreed. "Although I assumed you'd do that once you got home."

"Oh," Judy said, moving to the last pinkie toe.

"Don't worry, I'm impressed by your eagerness to obey me, and your eagerness to please me."

"I wasn't doing it to please you."

"No?"

"Well, maybe I was," Judy admitted. "Although I didn't know it was you."

"Regardless, your natural submissive persona came through, and you wanted your anonymous online Mistress to be proud of you."

"I guess," Judy said, unsure why she'd sent the pictures she did.

"Plus, a pussy pic," Marcy added. "That was a very pleasant surprise."

"I don't know why I did that."

"Because you wanted to impress your Mistress. You wanted her approval," Marcy said, having seen this characteristic with more than one MILF she'd seduced and liberated from the chains of housewife suburbia.

"Maybe, I really don't know," Judy said, thinking there was definitely some truth to what Marcy said, yet she'd just done it on a spur of the moment impulse... no real thought put into it.

"So tell me my pet, have you been fantasizing about submitting to your new mistress, about eating her pussy and sucking your new master's fat cock?" Marcy asked wickedly.

"Yes, I have," Judy admitted, figuring there was no denying the obvious, "But things are very different now."

"How so?"

"You're my employee," Judy pointed out the obvious.

"That's only serendipity, fate, or destiny," Marcy listed, as she took her feet off the desk. "It just makes things way more convenient, and it can expedite your submission."

"On the contrary, it means we can't do this at all," Judy insisted, her words a complete mismatch with the lust in her eyes as her intern stood up, lifted her skirt, and displayed her nylon-clad legs, the stockings held up by a garter-belt.

Marcy asked wickedly, seeing the daze and lust in her boss's eyes... which she'd seen many times before in older women desperate to break free from their marital boredom, "Are you quite certain we can't, my pet?"

Then Marcy hopped up onto Judy's desk, spread her nylon-clad legs and raised her skirt to her waist! Knowing her pretty pussy was kryptonite for any woman on the fence... recalling her history teacher in high school diving in after school inside her own classroom at her desk, or the airline stewardess who upgraded her into the otherwise empty first class cabin for the privilege of eating her pussy, or the mother of a bride who was late for her daughter's wedding because she was in the church bathroom eating Marcy's pussy. She asked, "Case in point: isn't this the cunt you've been dying to lick?"

Judy stared at the pussy she'd obsessed over for such a long time last night... which was glistening ever so lightly... and looked so inviting....

Judy bit her lip, speechless at the sight of the pretty pink pussy on display right before her eyes in her office.

"Well, my pet," Marcy pushed. "If you can't answer the question, there's a colleague of yours who will happily dive in on your behalf."

"What? Someone else here at work? Who?" Judy asked, partly curious, but more jealous.

"I don't seduce older women and awaken the slut within them and tell," Marcy said, as she brought her fingers to her pussy and parted her lips. "So I'll ask you just one more time. Do you wish to eat my cunt?" Marcy always used the word 'cunt', since it was nastier, and thus more powerful in a seduction.

Judy couldn't resist anymore, being so tantalized by the ripe young pussy directly in front of her, and she whispered, "Yes."

"Yes, what?" Marcy asked. "My pets are proud of who they are and of what they want. And look into my eyes while you answer me."

"Yes Marcy, I want to lick your pussy," Judy finally admitted unequivocally, her cheeks burning red with equal amounts of shame and lust, as she looked into the girl's eyes.

"The word is 'cunt'. Say it, my pet," Marcy corrected, loving to hear women who looked all prim and proper uttering that nasty word.

Judy didn't actually hate the word cunt, she'd used it freely back when her husband used to fuck her, so she reworded her response as instructed, "Yes, Marcy. I want to lick your pretty cunt."

"Good pet," Marcy approved, as she corrected, "but my pets never call me Marcy when we're alone together. It's either Mistress or Mistress Marcy. Is that understood?"

"Yes, Mistress," Judy agreed mindlessly, her gaze returning to the inviting pussy... sorry, cunt... she was craving.

"Kneel."

Judy obeyed, now on her knees, in her own office, her face now just inches away from her intern's cunt.

Marcy slid her ass forward and patted her boss's head like a puppy's, "Good girl."

Shame, lust, humiliation and excitement tore through her at the condescending words and gesture, yet she replied, wanting to lick that pussy so bad, her own pussy leaking out on her, "Yes, Mistress Marcy." Just using that honorific excited her.

"And now just one more item we need to address," Marcy said, knowing making her wait enhanced the woman's full submission even more, "would you like me to help you with your sexless marriage?"

Judy didn't hesitate as she answered, "Really? You could do that? Yes please, Mistress."

"Fuck, I still can't believe it's you."

"Ditto."

"Ditto?" Marcy asked.

"Sorry, it means the same as what you just said. And I loved the way they used it in the movie 'Ghost'."

"Aaaah, you look so hot on your knees between my legs," Marcy said, admiring this tableau.

"Thank you, Mistress," Judy said, looking up at Marcy, and then back down to her pretty pussy.

"Now usually at this point I'd invite you to dive in and sample the treat you've earned by being such a good pet," Marcy said. "But I have a better idea. Now be a good girl and place your hands on your desk, and spread your legs."

Judy was a little disappointed by not being allowed to lick that pussy, but she obeyed and said, "Yes, Mistress."

Marcy hopped off the desk, went behind her boss and admired her curvy figure... she really had a thing for larger women... both her man and she preferred BBW's or even better thick women... which Judy was a hundred percent the perfect thick bodies woman). Marcy pulled the woman's dress up to get a full view of that fine ass, placed her hands on Judy's wide hips and asked, "So tell me, my pet. When was the last time your husband fucked you?"

Judy had no idea of the exact date... it had been an eternity ago... "I'm not sure... six... maybe seven months ago?"

"Oh my God! Are you fucking serious? Six or seven months ago is inexcusable! I never go more than a day without getting my man's dick. But wait! Didn't you have an anniversary a couple of weeks ago?"

Judy felt her intern's hands on her ass squeezing her big booty as she answered, tears beginning to form as she replied, "We-we did, but he came home late and went right to sleep. I think I repulse him these days."

Marcy ran her fingers down the small of Judy's back, and down the middle of her juicy ass crack, then down her deliciously nylon-clad legs and said, disgusted by a man neglecting his responsibilities, "How could any man not want to fuck you? Or even any woman? Hell, I myself can't wait to fuck you with one of my strap-ons. Would you like that?"

Even as her eyes welled up, Judy answered, so excited to be touched by another person, "Yes please, Mistress."

"And would you like to suck my fiancé's big cock?" Marcy asked, as her finger moved between the lips of her boss's very wet pussy.

"Ryan's? Sorry, Master Ryan's? Yes please, Mistress," Judy moaned and trembled at her touch... the first intimate touch from another person in months, and the first one from a person outside her marriage in two decades.

As Marcy wiggled her finger between the wet pussy lips and struggled to comprehend what sorry excuse for a man would ignore the beauty and strength of such a woman, she said, "Such a good and wet girl! Now tell me more about your husband."

"What would you like to know?" Judy moaned, not even sure where to begin.

Marcy said, as she traced the pussy lips, teasing her pet relentlessly, "I want to know everything. Was he ever a good lover to you, is his dick big or small, was there ever any foreplay, did he ever make you come? I want to know when and where things went wrong."

Judy, as she was slowly teased by her young Mistress, retold how great their sex life had used to be. That her husband Ralph had a magnificent nine and a half inch horse cock, how he'd used to love dirty talk and was very aggressive in the bedroom. But in the months leading up to their last time, everything had started to change. He seemed to be repulsed by her constant squirting. Something he'd used to love.

Marcy listened intently, slowly but constantly teasing her pet's pussy, before she asked, "Would you say you've exhausted all options when it comes to spicing up your sex life?"

Judy agreed, feeling she really had run out of straws to grasp, "Yes...I think so."

"You only think so?" Marcy probed.

"Yes... yes I do," Judy responded confidently, thinking indeed she had.

As Marcy began fingering her pet a little faster, she asked, "So you allowed... even encouraged him to fuck you in public places, gave him head while he drove, and let him cum all over your pretty face?"

Judy moaned loudly, the slow fingering driving her wild, "Yes, yes, and yes."

Marcy continued her sexual interrogation. "Okay, then what about anal? Please tell me he's fucked this juicy ass with his horse cock."

After admitting to lots of things she had done, all of which had seemed to impress her young new Mistress, this time she couldn't answer in the affirmative. "Um, no. That's where I've always drawn the line, even though he begged me for it since before I walked down the aisle."