The Intern: Anal Deep DP

Summary: Submissive boss gets her first double penetration.

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 the part three of a four part series.

In part 1, The Intern: An Anal Seduction, a BBW, Judy, who is sexually frustrated from the neglect of her husband of twenty years goes online to explore and ends up being the submissive pet of her much younger sexy intern... beginning the journey to sexual submission and anal exploration.

In part 2, The Intern: An Anal Training, Judy continues to explore anal sex and ultimate submission to her young Mistress and her fat cock Master... all with plans to have her ass trained properly for her husband's nine and a half inch cock... which will happen in this final chapter.

The Intern: Anal Deep DP

THURSDAY MORNING

Judy walked into the office, plug still in her ass, wondering what today would bring.

Unlike the last couple of mornings, Marcy was in the office when she arrived.

"Close and lock the door," Marcy said, sitting at her boss's desk, her strap-on harness already around her waist for the morning ass fucking she planned for her pet... and generously lubed... although she assumed the plug would have her properly gaped for the fucking. She was always the first to pound a virgin ass... always. Of course, it was Ryan who would tear it apart later. Although this time, there was to be a deviation to the plan as she had decided that her pet's husband would get his wife's ass before Ryan.

"Do we have time to play this morning?" Judy asked, knowing there was a big meeting this morning, but hoping they could squeak in some pussy for breakfast.

"I believe we do," Marcy said. "Get in the position for a good morning fucking, my dirty ass slut."

"Yes, Mistress," Judy said, just seeing Marcy, then seeing Marcy stand up with a cock around her waist and then hearing her wicked tongue instantly making her pussy burn... getting fucked as good as eating pussy.

"Can you fathom that a week ago you were a boring prude bitch whose cunt was shriveling up like a raisin in the sun?" Marcy asked, as she walked behind her big bootied boss who bent over like the good submissive she was.

"It's crazy," Judy admitted, thinking how much her life had changed in just a few days based on a spur of the moment decision (well not that spur of the moment since she had been considering going online for a while, but actually doing it was) and then fate intervened as the one person she met online and had a connection with just happened to be her current intern. The odds were astronomical and yet true. "Did you know it was me when we first chatted online?" Judy asked, having wondered that.

"I did not," Marcy said, thinking to herself as she lifted up the dress and pulled her pet's panties down how much a coincidence it was... perhaps Cupid had a twisted sense of humour.

"When did you know?" Judy asked, her body shivering from a cold draft as her panties were pulled down to her ankles.

"When you sent me the pictures," Marcy answered, as she squeezed her pet's big juices ass cheeks. "I recognized your shoes and a couple items on your desk."

"I can't believe I sent them," Judy admitted, that being the most spontaneous thing she had done that wasn't some slut act with Frank, even going online was well thought-out before she did it.

"Yeah, I was stunned, staring at my new pet's obedience in the nylons I instructed her to wear and then her pussy while I waited in Starbucks to get said pet her daily drink," Marcy said, as she pulled the plug slowly out of her pet's ass.

"Ooooooh, that must have been quite the surprise," Judy said, feeling a subtle sensual sensation as the plug was pulled out of her ass. After wearing it in her butt all last night, through a heat sleep and this morning she had gotten used to it in there... and oddly she suddenly felt a little empty.

"Fuck, what a nice gaped asshole," Marcy said, as she admired the beautiful round inviting hole... God, she loved a well gaped hole... especially after Ryan.

"Thanks," Judy said, wondering if she was going to put an even bigger plug in her asshole.

"Yes, such a nasty big gaping hole," Marcy said, as she bent down and rimmed the medium sized hole.

"Ohhhhh, yes, rim my asshole," Judy moaned, recalling that Marcy got a little submissive when eating an ass.

"You like this? You like your intern eating your asshole?" Marcy moaned, as she slid her tongue inside the gaping hole.

"Yes, I should have made this one of the expectations years ago," Judy joked.

"Mmmmmmm," Marcy moaned, eating an asshole always turning her on and making her pussy tingle.

"Yes, tongue fuck my asshole, my intern slut," Judy ordered, as she reached back and held her intern's head buried between her big booty.

"Mmmmmmmmm," Marcy moaned again, as she was a natural switch. With Ryan or other men she was a mindless submissive eager to obey any task to get a dick in one of her three holes.

"Fuck, I love your tongue fucking my asshole," Judy moaned as she really enjoyed the tongue probing her ass... feeling both sensual and nasty at the same time.

Marcy ate the asshole for a couple more minutes, loving the nasty act and dirty taste, before she pulled herself up and said, "Now, time to fuck this asshole and take your anal virginity."

Judy wasn't expecting to be ass fucked as her eyes went wide and she suddenly had a cock deep in her asshole. "Ooooooooh, God!" Judy gasped and moaned in shock and pleasure.

"Yes, this asshole is mine, say it, slut," Marcy said, smoothly shifting from submissive ass eager to dominant ass fucker.

"Yes, my asshole is yours," Judy agreed, in awe of the sensation of a dick in her ass and Marcy's body resting against her... even as she processed she had a dick in her ass.

"Do you want me to fuck your big booty?" Marcy asked, giving three quick strokes.

"Oh, you mother fucker," Judy moaned, stunned at the pleasure she was experiencing at the moment mixed with just the slightest pain as the cock went deeper than either previous butt plug.

"I do love fucking, especially ass fucking, big ass mother sluts," Marcy said. Giving five quick, deep tougher strokes.

"Jesus Christ," Judy moaned, a cock in her ass a completely different sensation than in her pussy.

"What do you want, slut?" Marcy asked, slowly pulling out and slamming back in just once.

"For you to fuck me," Judy said, this slow teasing driving her wild with lust and frustration.

"Fuck what?" Marcy questioned, pulling all the way out to tease her and admire once more the beautiful perfectly round gaping hole.

Judy turned back to look at her sexy Mistress, "My asshole, Mistress, take my anal virginity, turn me into a three-hole bimbo whore and prepare my ass for my husband's big cock and your man's fat prick."

"Fuck, I love hearing you talk so nasty," Marcy said, nothing turning her on more than a nasty verbal slut and anal play.

"Well, I'm your three-hole fuck toy, cunt licker, cock sucker, ass taking slave," Judy declared, willing to say anything to have that cock back up her asshole... each self-verbal assault enhancing her excitement.

"More," Marcy ordered, as she slid her cock back in her pet and began fucking her ass.

"Oooooh, I'm your slut... fuck... your ass slut... your mindless whore," Judy babbled, trying to think of new ways to say the same thing, but the cock in her ass was distracting her greatly.

"Yeah, tomorrow Frank is going to fuck this ass good," Marcy said, imagining nine plus inches slamming into this backside as well as her own asshole.

"And will Master be fucking my ass?" Judy asked, the idea of that fat fucking dick tearing her asshole wide a major turn on at the moment.

"Oh, he is dying for a shot at your big ass," Marcy said, as she fucked her pet good. "But I told him your ass was off limits until after Frank got to fuck it."

"Mmmmmmmm," Judy moaned, her pussy on fire as her asshole got reamed and she imagined her husband's stunned face when she offered up her asshole tomorrow.

"You love getting this ass fucked, don't you?" Marcy asked, listening to her pet's moans.

"I fucking love you reaming my asshole," Judy said, as her orgasm was rising.

"Are you going to come without having your pussy touched?" Marcy asked, a couple dozen strokes later as her pet's moaned increased... as she loved when she had an anal only orgasm and also loved seeing another woman have one from her strap-on fucking or Ryan's ass stretching drilling.

"I think so," Judy replied, feeling like she could burst at any moment.

"Come for me, my ass slut," Marcy said, as she reached up, grabbed her pet's hair and pulled.

"Oh yes, fuck my ass, fuck me, fuck my asshole, pull my hair," Judy babbled, her head going light as her orgasm approached.

"Come, you ass taking, cunt licking, whore," Marcy said, getting quite the work out from the rough fucking she was giving her boss.

"Don't stop, don't stop, oh fuck," Judy moaned, her orgasm so close, yet not erupting like it would have if this dick was in her pussy.

"Now, slut, come now," Marcy demanded, really railing her boss's ass while pulling in her hair.

"So, fucking close," Judy said, beginning to get frustrated she hadn't come yet.

"It takes longer in the ass, but you are about to have an anal orgasm that will shake you to your core," Marcy said, knowing from experience that anal orgasms took longer, often felt like they were never going to come but when they did they would send fireworks through the very core of your being.

"So close, don't stop, fuck my ass, fuck, harder, oh fuck, damn it, fuck, so close," Judy babbled like a bimbo bitch in heat for another minute and just when she thought the damn was not going to break sit suddenly did and she covered her mouth just in time as she screamed, "Fuuuuuuuuuuck."

Marcy kept hammering away knowing the waves of an anal orgasm were more intense if the ride continued.

Judy actually slammed her hand on her desk five times as the pleasure cascaded through her and her cum sprayed out of her all over her desk, her legs and the floor.

"Let it flow through you," Marcy said, slowing down but not stopping.

"So good," Judy said, in a euphoric haze.

"I know," Marcy said, knowing they were running out of time before the meeting.

"Fuck," Judy said with no purpose as she felt completely spent.

Marcy pulled out and said, "Hate to take your anal virginity and leave, but the meeting starts in a few minutes."

"Your killing me," Judy said, still bent over her desk, still feeling the aftershocks of an anal orgasm and still processing the reality she had just been sodomized.

"What a way to die," Marcy joked, as she slipped out of her harness.

"Agreed," Judy said, as she slowly stood up straight and felt more wetness leak out of her.

"I'll see you in a few minutes," she said putting her strap-on away and knowing she had to clean it.

"Yeah," Judy said, not really remotely ready to lead a meeting.

"Don't worry, you have some pussy to eat later, some cock to suck and maybe if you're a good girl some dp action," Marcy said, grabbing the plug off the desk, bending her boss back over the table, and easily sliding it back in her pet's ass.

"You really are going to kill me," Judy said, the plug not stretching her at all anymore. "You've given me orgasms this week than Frank the past two years."

"Making up for lost time," Marcy said, as she walked out of the office.

"Fucking crazy," Judy said, standing up just as her secretary walked into the office.

"Mr. Baker on line five," her secretary said, noticing her boss's cheeks very, very flushed.

.....

THURSDAY LUNCH

Judy had ordered lunch in for her and Marcy as they needed to go through the working plan for a presentation this afternoon.

They actually worked through lunch until they were both content with the visuals that went along with the presentation.

Marcy then asked, as she sat on her boss's desk and spread her legs, "Want some dessert?"

"I do," Judy said, having always liked dessert and really liked and craved Marcy's fresh pie... which had replaced her afternoon Starbucks addiction. She moved to her young intern, lowered herself before the spread legs and dove in.

"Take your time, my pet," Marcy asked, "we have no other engagements for at least half an hour."

"Yes, Mistress Marcy," Judy obeyed, as she explored every nook and cranny of this beautiful, delicious pussy.

After a few minutes of slow teasing exploration, Marcy ordered, "Don't forget about Mistress's asshole."

"How could I neglect that?" Judy said, as she slithered her to way down between the small spot from the delicious pussy to the tart ass.

As her boss licked her rosebud, Marcy moaned, "That's it, my pet, lick my asshole nice and good. Master tore it apart last night."

"Mmmmmmm, I would have liked to see that," Judy moaned, recalling Ryan's huge cock buried in this sexy butt yesterday, but from her position eating pussy she didn't get a really good look.

"Want to come over tonight and see it up close and personal," Marcy asked.

"Yes, please," Judy replied, perhaps a little too eagerly.

"Eager to watch me be ass fucked?" Marcy asked.

"Yes, Mistress," Judy said. "I didn't get a really good view last time."

"I'll make sure you get a really close look tonight," Marcy promised, as she put her hand on the back of her boss's head and pulled her up from her ass and back to her wetness wordlessly implying it was time to stop talking and really get licking.

Judy attacked the clit with her tongue and lips wanting to get her intern off and taste the full flood of her cum.

"That's it, my pet boss, suck on my clit, finger bang me," Marcy moaned.

Judy slid two fingers in her Mistress's pussy and furiously pumped her fingers in and out as Marcy moaned louder. "Oh yes, you nasty cunt licking slut. Finger fuck your Mistress."

Judy did as instructed and double attacked the pussy with her lips and fingers wanting to get her young mistress off and taste her creamy cum.

"Oh yes, you nasty cunt hungry bimbo slut," Marcy said, as she pulled her pet boss deep into her oasis of wetness as she was about to burst.

Judy was overwhelmed with the scent of heaven as her face was pressed against the wet pussy. She kept licking, flicking the clit; she kept fingering the pussy. A moment later she felt her face get drenched with sweet, sweet cum which she drank directly from the source.

Marcy enjoyed her orgasm as her boss kept licking away.

Judy licked up the pussy cum until Marcy pushed her away. "God, you are a natural cunt muncher."

"At least your cunt," Judy smiled looking up at Marcy with her face glistening with natural wetness.

"Mmmmm," Marcy smiled, as she hopped off the desk. "Bend over the desk. Time for plug three."

"Mmmmm, "Judy responded, as she stood up, bent over her desk and eagerly waited.

Marcy went to her bag, grabbed the large plug, lubed it generously, and sauntered back to the big bootied boss. She admired it briefly before pulling the medium sized plug out. "This isn't doing anything anymore."

"Not after you fucked the living shit out of me," Judy joked, feeling briefly empty and expecting to soon feel very full.

"True enough," Marcy laughed, thinking that this mistress-submissive relationship was more than just sex. It was friendship. "This one will really stretch your asshole."

"Okay," Judy said, ready for the pain she was sure was going to course through her as the biggest plug yet filled her well gaped asshole.

Marcy slowly positioned the large plug at her pet's asshole and slowly slid it inside the gaping hole.

"Ooooooh," Judy moaned as the plug slid inside her... the pain delayed... as the gaping allowed the smaller end to move inside with ease before it finally began to stretch her ass.

"Remember to breathe," Marcy reminded her boss.

"Yes," Judy responded, a sudden searing pain coursing through her as the plug reached new depths inside her... stretching her ass wider than it ever had been stretched and deeper than she thought possible.

Marcy watched, always in awe of seeing a large plug disappear into such a small hole.

"Oh my," Judy said, through gritted teeth, the pain intense... yet somehow subdued by the thrill of the sexual submission.

"Your ass can swallow anything," Marcy said, as the entire club disappeared into Judy's big booty.

"So full," Judy whimpered,

"Got to get this asshole ready to easily take big cock," Marcy pointed out.

"Oh, I think I'll be able to take some Congo dick when your done with me," Judy joked, trying to ease her pain with humour.

"Congo dick?"

"Yeah, I read somewhere the biggest dicks in the world came from there," Judy said.

"Well, we may have to go on a company retreat there," Marcy joked, as she pulled Judy's panties back up to hold the large plug in her pet boss's ass.

"I'm supposed to work with this is me?" Judy said, not yet ready to stand up... still getting used to such a huge toy in her asshole.

"Yes, slut," Marcy said. "And you better spend some time getting accustomed to the plug as the meeting is pretty big."

"Like the plug," Judy joked again, as she slowly stood erect... feeling the toy shift inside her creating a new pain.

"Exactly," Marcy said, slapping her pet's ass making her pet scream.

"Aaaaaaaah," Judy yelped, as the toy somehow went deeper in her ass when it was spanked.

"Oops," Marcy smiled.

"Yeah, oops," Judy said, shaking her head as she started walking slowly....

"See you soon," Marcy said.

"Yeah," Judy said, this plug much bigger than the previous two.

Judy spent twenty minutes walking around getting used to the plug, even sitting down a few times, which shifted the plug differently.

The rest of the afternoon was a little excruciating, literally: a plug in her ass, a meeting that went way too long and didn't end with a sealed deal (although it did look likely) and she was surprisingly horny... looking forward to going to Marcy's tonight.

Marcy texted her to show up at eight....

Which she did....

"Hey, slut," Marcy greeted, in all red lingerie, her tits barely held in her attire.

"Hi, Mistress," Judy greeted, having changed into some sexy lingerie herself, all black.

"Come in," Marcy offered.

"Thank you, Mistress," Judy said, walking in as Marcy closed the door.

As soon as the door was closed, Marcy ordered, "Knees, slut."

"Yes, Mistress," Judy obeyed, loving just obeying mindlessly and anticipating a great night.

"Follow me, pet" Marcy said, wearing four-inch red pumps.

"Yes, Mistress," Judy repeated her favourite phrase... also enjoying perversely the submissive act of crawling like an actual pet.

Marcy walked into her living room and Judy followed like the pet she was... a little surprised to see another woman, quite large, on her knees, between Master's legs.

"Pet Judy this is Bimbo Belinda," Judy introduced, as Judy saw tat Belinda was sucking Master's cock.

Belinda waved without stopping to slowly suck Master's cock. She had been caught in his and many other compromising acts by strangers, her husband, both her kids and even her mother over the past three years. Belinda was their next door neighbor, married, with two college age kids who succumbed to Marcy's charm within two weeks of them moving beside her... rekindling a dormant sex drive to heights she never had even in her slutty three hole college days (where she learned being large meant doing the things skinny girls didn't do... swallow and take it in the ass for example). Alas, once she had kids her drive diminished until Marcy.