The Intern: An Anal Training

The Intern: An Anal Training

Summary: Submissive boss gets her ass trained to take big cock.

Note 1: Thanks to Breezy who came up with the idea for this fun tale.

Note 2: Thanks to Tex Beethoven for editing this story.

Note 3: This is part two of a trilogy. In part 1, The Intern: An Anal Seduction, a boss, Judy, a well known and widely respected CEO of a large corporation, is sexually frustrated because of the neglect from her husband of twenty years, and that frustration has driven her into becoming a total bitch to everyone at work. She goes online to explore any sexy possibilities she can find, and soon becomes the submissive pet of an anonymous woman along with her fiancé, who the next day turns out to be her very own much younger sexy intern... one of the many people she's been a downright bitch to... but who nevertheless takes her boss in hand... and thus beginning Judy's journey into sexual submission and anal exploration.

The Intern: An Anal Training

MONDAY NIGHT:

Judy struggled to stay focused through the rest of the day.

Her pussy was leaking constantly.

She couldn't stop replaying what she'd allowed to happen in her office.

The good... it was a life altering, body quaking, encounter.

The bad... it had happened in her office, with her intern.

The good... she'd finally achieved the orgasm she'd been dying to have for months... and even though it wasn't a fuck... it was nevertheless very intense.

The bad... she'd cheated on her husband... although she didn't feel a lot of guilt for it, since he'd unknowingly pushed her into it by his total neglect of her, and she hadn't been with another man.

The good... apparently she did have a g-spot: something no man had ever located. (She'd never been with a woman before.) And her g-spot orgasm had been more intense than almost anything she'd ever experienced before.

The bad... she'd opened herself up to possible blackmail and humiliation... even though for some reason she trusted Mistress Marcy's judgement and discretion, and as for the humiliation... at least so far... it wasn't necessarily a bad thing. It was actually rather exciting!

The good... for the second time ever... the first time many years ago had been disastrous... she'd allowed her ass to be penetrated, and this time it hadn't hurt her or killed her mood... it had actually enhanced the experience.

The bad... she'd agreed to experience more sodomy from Marcy's fat-cocked fiancé. And when that happened, it would irrefutably be cheating!

The good... Mistress Marcy had offered to help her in straightening out her sexless marriage. Judy had no idea what that might look like when it happened, but her Mistress had seemed quite sure of herself, and from everything she'd experienced with the girl today at lunchtime, she inspired confidence.

She arrived home, ordered in food, had a bath, and was lounging on her bed wearing thigh high stockings and nothing else as ordered, her laptop open watching some lesbian porn. At two minutes to eight she called Marcy.

"Hi, slut," Marcy moaned, as her man slowly fucked her ass. Judy couldn't see what was happening of course, but she was very aware of the moan.

"Hi, Mistress," Judy greeted.

"When is your husband returning?" Marcy asked, enjoying the slow ass fucking, which would result in her ass being well gaped before the upcoming deep, rough, satisfying ass fucking.

"Friday," Judy answered, watching a needy student place her hands on her teacher's shoulders and guide her to her knees before her... an act Judy found so sexy, so erotic, so pussy leaking.

"Perfect," Marcy moaned. "That gives us a few days to train your asshole."

"Really?" Judy asked.

"Yes, by the time he returns home, you'll be begging for him to pound your tight asshole and thus blow his mind," Marcy assured her, very confident that would indeed be the case.

"I really don't know about that," Judy said, thinking a thumb sneaking into her ass and only going an inch and a bit inside, was a whole lot different than nine and a half inches of cock pounding away in there.

"Oh, but I know," Marcy said. "Your ass was made to be fucked."

"Really?" Judy asked, that prospect seeming a little too much.

"Yes, big girls like we are were born to suck cock, to get our tits fucked, and to be sodomized roughly," Marcy said, all things she did regularly.

"Well, I've done two of those things pretty regularly, or at least we used to," Judy said. Ralph had loved fucking her tits in the past, although like everything else in the past six or seven months, he'd totally lost interest.

"Well, two out of three ain't bad," Marcy drawled, as she began slowly rearing back to meet her man's forward thrusts. "But three out of three is even better."

"I guess so," Judy said, wondering what Marcy was doing... she was either masturbating, using a toy, or being fucked.

"Trust me, my pet," Marcy said, "once you get accustomed to having a cock buried in your asshole, you'll crave it."

"I can't imagine," Judy said.

"Then here's a helpful order from your wise and... admittedly young... but nonetheless experienced... Mistress. Until you allow Ralph to fuck your asshole, you're only permitted to have an orgasm by fingering your asshole or fucking your back door with a toy," Marcy dictated. In practice she knew there'd be exceptions to that rule, but she'd always be present and the one calling the shots.

"Oh, Mistress, my pussy has been burning all day! You've made me into a perpetually cunt leaking slut," Judy cried out in exaggerated despair, hoping a touch of desperation and talking dirty would change her Mistress's mind.

"Glad to hear it! And if you want to come again, it's pretty simple: you may either finger bang your ass, or grab a toy and fuck your sexy ass," Marcy said. "At the moment, my ass is filled with seven inches of dick."

"Lucky girl," Judy said, meaning at least she was getting fucked, but realizing it likely sounded otherwise.

"Oh, you'll be lucky too, very soon," Marcy moaned, as she began bouncing back on Ryan's fat cock, knowing part of Judy's training was the inspirational seven inches of dick plowing her own ass. "I'm going now. I need my man to really ream my asshole."

"Okay, bye, Mistress," Judy said, having hoped for a longer encounter.

"Bye, ass slut," Marcy moaned, and she hung up just as Ryan began really destroying her ass.

Judy sighed.

On her laptop, the teacher was now eating the student's pussy, and Judy instantly wanted more pussy. She watched porn for almost an hour, her pussy on fire, and needing to come, she stuck her finger into her pussy and got it good and wet before she brought her wet finger to her ass and slowly pushed it inside. It was awkward to finger fuck her ass compared to finger banging her pussy, which she began doing with her other hand.

There was a little discomfort in her ass, but intense fire in her pussy as she double penetrated herself... something she'd never done before, which made her wonder what it would feel like to have cocks in both her pussy and her ass.

While on her screen a cheerleader wearing a strap-on was really drilling another cheerleader, Judy fucked herself to an orgasm by fingering both of her holes.

As she washed her hands once her orgasm was done, she wondered what the next few days would be like.

Although she was a little nervous... she was far more excited.

.....

TUESDAY MORNING AND EARLY AFTERNOON

At work, all morning Judy was excited yet frustrated.

She hadn't seen Marcy all morning, and her pussy was wet with anticipation. She led two meetings, the entire time wanting them to be over, so she could continue her wild sexual exploration.

It was just after lunch when Marcy walked in and asked point blank, "Did you come last night?"

"Yes, Mistress," Judy said, a chill of adrenaline coursing through her, the moment she saw her intern.

"Did you finger your ass?"

"Yes, Mistress," Judy said, "as well as my pussy."

As Marcy hopped onto the desk, she said, "So you double banged yourself... hot."

"It was weird," Judy said.

"Ready for your new version of Starbucks?"

"Yes, Mistress," Judy said, getting eagerly out of her chair and hurrying to her intern.

Marcy spread her legs to reveal her black thigh high stockings and ordered, "Hurry up. I need to meet with Mr. White in ten minutes."

"Yes, Mistress," Judy replied, as she hurried to the invitingly spread legs and dove right in... having craved this pussy ever since she'd finished dining on it yesterday. And that had been her first taste of pussy ever!

"Oh yes," Marcy moaned, "I can tell you like your new afternoon drink."

"Love it," Judy said mindlessly, as she licked hungrily... usually she needed her afternoon Starbucks for the caffeine rush to get through the afternoon, but this pussy was proving to be her new adrenaline afternoon pick me up.

"And it's a lot cheaper than a Starbucks drink," Marcy said.

"And tastier," Judy added, now choosing pussy over coffee in a heartbeat.

"And healthier," Marcy added.

"Mmmmmmm," Judy moaned, as just like sucking dick made her pussy wet, she'd always gotten turned on from pleasing others, and eating pussy also made her pussy wet... very fucking wet.

"You want my cunt cum, slut?" Marcy asked, her orgasm close.

"Yes, Mistress, come all over your boss's face," Judy replied lustfully.

"Suck on my clit and finger bang me," Marcy ordered.

"Yes, Mistress," Judy obeyed, doing both, as two fingers easily slid inside her Mistress's wet box, and her body began twitching as the pet sucked on the swollen clit.

"Oh fuck, you cunt licker, ass taking slut, cum bucket," Marcy rattled off, just before she flooded her pet's face with cum.

"Mmmmmm," Judy moaned, loving the name calling and nasty talk, as well as the delicious cum that flooded out of Marcy's pussy and into her own mouth.

Once she was spent, Marcy said, as she got off the desk, "I expect you to be in the basement, room two, at 2:30. Is that clear?"

"Really? I've never been in the basement," Judy said.

"Just be there," Marcy ordered. "We need to get that ass ready for nine plus inches of cock."

"Yes, Mistress," Judy said.

....

LATER TUESDAY AFTERNOON

Judy took the elevator to the basement and began finding her way to room two, surprised at how many rooms were down here, and learning this was where all those files ended up after she approved them. As she proceeded, she wondered why Marcy wanted to meet here, since they'd already enjoyed two sexual encounters in her office... there didn't seem to be a need for a secluded discreet location... and since Marcy was expected to be in her office often, there was no reason for anyone to suspect anything.

As she reached room two, horny as hell, she was surprised to see room two was a storage room. She walked in and saw the janitor standing there... the one Marcy frequently chatted with. It was then that she put two and two together.

The janitor was Marcy's fiancé.

The janitor was Master!

"Close and lock the door," Ryan said, as he texted Marcy: Slut's here.

Marcy closed and locked the door, processing her newfound revelation, when her phone rang.

"Put your phone on speaker, slut," Marcy ordered.

"Yes, Mistress," Judy obeyed, while she tried to rationalize what was already happening, and what was about to happen.

"Place your phone on the table, pet cock sucker," Marcy ordered, sounding a little more dominant with Ryan in the picture. Marcy had perfected the dual rules of being a Mistress. The first was being seductive, sensual, understanding and compassionate as she seduced the woman. The second, once the seduction was in place and the new pet was meeting Master for the first time, she shifted verbally into a more traditionally dominant Mistress. She knew from experience that almost all MILFs she seduced succumbed to her and submitted to sexual servitude out of need, curiosity and a perverse belief that having sexual encounters with someone of the same sex wasn't really cheating. On the other hand, taking another man's dick was definitely considered cheating, so a stronger, heavier-handed approach was more effective.

Marcy again obeyed, "Yes, Mistress," as she set the phone down on the wooden table.

"Now pull out Master's cock," Marcy ordered, while within her own office upstairs, Mrs. Alden, the black Personnel Manager, slowly licked her Mistress's pussy under her desk.

Mrs. Alden was dying to know who the couple's latest conquest was. Marcy had reawakened her dying sex drive, and she now ate the pussies of five different younger employees, and was provided with cock to suck and to ride through a glory hole downstairs in room one.

"Yes, Mistress," Judy obeyed, as she approached the muscular and tattooed man she'd never really paid any attention to. She knew what she was doing was wrong, knew this was definitely cheating, and yet was well aware of the fact she'd agreed to mindless obedience. She was also aware... this was the line that if she crossed it, there was no going back.

Judy walked the few steps to the man, not once making eye contact but downcast instead, and she felt such humiliation as she, the CEO of the whole damned place, dropped to her knees before a janitor... a person she'd ignored for years as far below her and had treated like crap whenever she'd had reason to pay any attention to him at all. (She hadn't hired him, of course... that would have been Mrs. Alden.)

Her hands trembled as she undid Master's belt, tugged at his jeans button and unzipped him. She was both dying to see the fat cock up close and personal, the picture of it having tantalized her and made her mouth water (she'd gazed upon it at least a hundred times), and yet she was trembling with the reality of what she was about to do.

She pulled down his jeans and boxers, and a semi-erect fat cock was suddenly poised before her... her first new one in over two decades. Although her husband had an amazing cock that filled her completely, and she couldn't fathom being able to take any more in length, this cock put Ralph's to shame in girth.

"What do you think of my man's cock?" Marcy asked.

Mrs. Alden remembered the first time she'd seen that fat cock, and how she'd sucked it and taken his load in the back alley behind the break room, begging him to come in her unprotected pussy (although he elected to come on her face), then took it in her pussy the next day in her office, when he did indeed unload into her fertile womb, and had gotten her asshole stretched in ways she hadn't imagined possible in her home, while her husband watched and was glad to receive a hand job from Mistress Marcy.

"It's so fat," Judy said, in awe of the fat cock dangling before her.

"I know," Marcy said. "Is it hard yet?"

"Semi-hard," Judy said, wanting nothing more than to see this cock fully erect, already having forgotten about Ralph, or the wedding ring on her same hand that was slowly stroking the majestic cock.

"Well, suck that cock and get it hard, it ain't gonna get hard by itself," Marcy said, although that obviously wasn't true. That cock got hard all the time all by itself... it was almost constantly erect, bless its heart.

For Judy that made sense, and she opened her mouth to take the fat cock in, not really thinking about anything but that cock. She wanted to feel it in her mouth. She wanted to feel it hardening between her lips. She wanted to feel it stretch her mouth wide open. She wanted to see and feel it while it was rock hard.

"That's it, slut," Ryan finally spoke for the first time. "Get my fat cock nice and hard."

"Does she look hot with your cock in her mouth, baby?" Marcy asked, thinking she should have been down there to watch this... but she'd wanted to see if Judy would obey mindlessly without her being there.

"Yeah, it's the best she's ever looked," Ryan said, "not bitchy at all right now," as Judy slowly sucked his cock... her cheeks going red at the casually disrespectful way this janitor who was now her Master was talking about her... yet she loved feeling his fat cock hardening between her lips.

"She looked pretty hot between my legs, too," Marcy moaned.

"Yeah, she did," Ryan agreed, having seen the pictures and watched the video.

Judy felt her mouth really stretching as Ryan's cock hardened completely. She knew she shouldn't be doing this, she knew she was cheating. Yet her pussy was on fire, her submissive nature was leading the way, and besides, If her husband had been fucking her like she'd needed, she wouldn't be in this situation at all!

"That's it, slut, get my cock ready for that pussy of yours," Ryan said, impressed by this older woman's mouth. She was using her tongue while she sucked, creating some extra wetness that enhanced his pleasure. Although Marcy was a great fuck, both her pussy and ass completely heavenly, and she sucked dick really good... nobody sucked better than older bitches... that was a fact.

Judy had kind of assumed she'd be sucking his cock and either swallowing the load or taking a facial... a blow job not as extreme a cheating activity as allowing another man into her pussy.

"My pet, are ready to receive the fucking you've been craving for months?" Marcy asked.

Ryan pulled his dick out, pulled the overwhelmed MILF up, spun her around, and bent her over the table, the phone now directly in front of her as she wailed, "Oh, Mistress, I really shouldn't be doing thiiiiiiis!"

Ryan knew timing was everything when an older woman was cheating on her husband for the first time, so he lifted up her dress and slid his cock inside her already very wet pussy before she had time to think or finish her protest.

Judy was stunned by how quickly she'd progressed from a cock in her mouth to the cock in her pussy... a stopwatch would have timed it at just shy of three seconds.

"Such a wet slut," Ryan said, as he began slamming into the bent over CEO.

"Oh God!" Judy cried out, both because she was getting fucked by another man, and because the instantaneous pleasure from the thick cock was driving her wild!

"Is he stretching your pussy, my pet?" Marcy asked, wishing she was there to watch it, although she knew it was being filmed, as were all the encounters in that room. They had a very sophisticated setup down there where a motion sensor controlled not only whether the camera was filming, but where it was pointing. Complete with sound, of course.

"So good," Judy moaned, not really answering the question, but overwhelmed by how well her pussy was being filled. Somehow this seven inches seemed larger than Ralph's nine and a half, since it was filling her in a much different, yet still extremely pleasurable way.

"I'll take that as a yes," Marcy laughed, as she tapped her nearby pet's head, which instructed the black beauty to shift from slow leisurely licking to more aggressive action.

"So big," Judy moaned, the cock indeed feeling so big, stretching her so good, and bringing her intense pleasure.

"Yeah, he's a great mother fucking stud," Marcy said with great confidence, since every woman she brought to Ryan went ape shit for his cock.

"Harder, fuck me harder," Judy heard herself begging, her inner slut taking over.

"Do the wall bang," Marcy ordered.

"The what?" Judy asked, as Ryan pulled out of her.

Ryan spun her around, lifted her into the air by her knees, somehow managed to drop her square onto his erect cock, and walked her to the nearest wall.

"Oh, my fucking God!" Judy moaned, as she was dropped onto a cock and filled in a way she'd never even imagined being filled, hitting erogenous zones she hadn't imagined existed. Now, this was a real man! Picking up her big body, along with her big booty, as if she were an autumn leaf!